Every row of the two group corpora, by name: what each pattern matches, and for a protecting group,
what removing it reveals. This page is generated from
chython/reactions/tables/functional.tsv and chython/reactions/tables/protective.tsv, which are
the authority — a name that appears here is a name the shipped table has.
The API is on :doc:`reactions`: :meth:`chython.MoleculeContainer.functional_groups` and
:meth:`chython.MoleculeContainer.protective_groups` report what a molecule carries,
:meth:`chython.MoleculeContainer.deprotect` applies the removals, and both corpora are also reachable
as tables through :func:`chython.functional_rules` and :func:`chython.protective_rules` — the whole
inventory, keyed by the name below, no molecule involved. The SMARTS column is the chython dialect,
documented in :doc:`substructure`; z and x there do not mean what the same letters mean in
another toolkit's dialect.
The reaction corpus and the role table are not listed here: a reaction row is a template rather than a name a molecule carries, and :doc:`reactions` documents it where it is applied.
253 functional groups, alphabetically. The name is the key :meth:`chython.MoleculeContainer.functional_groups` returns and the key :func:`chython.functional_rules` is keyed on; the id is what a consumer stores.
| Name | Id | SMARTS | What it matches |
|---|---|---|---|
1_2_diketone |
functional:75 |
[O;z2;x0:1]=[C;D3;x1:2]-[C;z2;x1;D3:3]=[O:4] |
1,2-diketone |
1_3_diketone |
functional:76 |
[O;z2;x0:1]=[C;D3;x1:2]-[C;z1;D2,D3:3]-[C;z2;x1;D3:4]=[O:5] |
1,3-diketone |
1_4_diketone |
functional:77 |
[O;z2;x0:1]=[C;D3;x1:2]-[C;z1;D2,D3:3]-[C;z1;D2,D3:4]-[C;z2;x1;D3:5]=[O:6] |
1,4-diketone, the Paal-Knorr substrate |
NO_dialkylhydroxylamine |
functional:164 |
[N;D2;z1;x1;h1:1](-[C;z1:2])-[O;D2;z1;x1:3]-[C;z1:4] |
R'-O-NH-R'', the Weinreb amine |
O_alkylhydroxylamine |
functional:163 |
[N;D1;z1;x1:1]-[O;D2;z1;x1:2]-[C:3] |
R-O-NH2 |
acetal |
functional:186 |
[O;D2;z1:1]-[C;z1;x2;h0,h1:2]-[O;D2;z1:3] |
R-O-CH(R)-O-R, the masked carbonyl. h0,h1 admits the ketal and excludes an orthoester |
acrylamide |
functional:195 |
[C;z2;D1:1]=[C;z2:2]-[C;D3;z2;x2:3](=[O;D1;x0:4])-[N:5] |
H2C=CH-CO-N, the covalent-warhead acceptor. D1 on the terminal carbon: a beta-substituted acrylamide is a far weaker acceptor and is not this |
acrylate_ester |
functional:196 |
[C;z2;D1:1]=[C;z2:2]-[C;D3;z2;x2:3](=[O;D1;x0:4])-[O;D2:5] |
H2C=CH-CO-O-R, the polymerizable monomer. D1 as in acrylamide |
activated_isocyanide |
functional:166 |
[C;-;D1:1]#[N;+;D2:2]-[C;z1;h1,h2:3] |
isocyanide with an acidic alpha C-H; what activates it is left unstated |
active_methylene |
functional:167 |
[C;z1;D2,D3;x0:1](-[C;z2,z3;x1,x2:2])-[C;z2,z3;x1,x2:3] |
CH flanked by two EWGs, the Knoevenagel nucleophile |
acyl_azide |
functional:240 |
[N;D1;z2;-:1]=[N;D2;+:2]=[N;D2;z2:3]-[C;D3;z2:4]=[O;D1;x0:5] |
R-CO-N3, the Curtius substrate, as distinct from the alkyl azide |
acyl_bromide |
functional:84 |
[Br;D1]-[C;z2;x2;D3:1]=[O:2] |
R-COBr |
acyl_chloride |
functional:23 |
[Cl;D1][C;z2;x2;D3:1]=[O:2] |
R-COCl |
acyl_fluoride |
functional:85 |
[F;D1]-[C;z2;x2;D3:1]=[O:2] |
R-COF |
aldehyde |
functional:20 |
[O;z2;x0:1]=[C;D2;x1;z2:2] |
R-CHO |
alkene |
functional:2 |
[C;z2;x0;D2,D3:1]=[C;z2;x0;D2,D3:2] |
internal C=C, no heteroatom on either carbon |
alkenyl_boronic_acid |
functional:62 |
[B;D3;z1;x2](-[O;D1])(-[O;D1])-;!@[C;z2;x1:1]=[C:2] |
vinylboronic acid |
alkenyl_boronic_ester |
functional:63 |
[B;D3;z1;x2](-[O;D2;x1])(-[O;D2;x1])-;!@[C;z2;x1:1]=[C:2] |
vinylboronate ester |
alkenyl_bromide |
functional:49 |
[Br;D1][C;z2;x1:1]=[C:2] |
vinylic C-Br |
alkenyl_carboxylic_acid |
functional:81 |
[O;D1;z1;x0]-[C;z2;x2;D3:1](=[O:2])-[C;z2:3]=[C:4] |
alpha,beta-unsaturated acid |
alkenyl_chloride |
functional:48 |
[Cl;D1][C;z2;x1:1]=[C:2] |
vinylic C-Cl, the Heck/Negishi electrophile |
alkenyl_fluoride |
functional:47 |
[F;D1][C;z2;x1:1]=[C:2] |
vinylic C-F |
alkenyl_grignard |
functional:112 |
[Mg;D2](-[F,Cl,Br,I])-[C;z2:1]=[C:2] |
vinyl Grignard |
alkenyl_iodide |
functional:50 |
[I;D1][C;z2;x1:1]=[C:2] |
vinylic C-I |
alkenyl_molander_salt |
functional:68 |
[B;D4;z1;x3;-](-[F])(-[F])(-[F])-;!@[C;z2:1]=[C:2] |
vinyl trifluoroborate |
alkenyl_silane |
functional:123 |
[Si;D4]-;!@[C;z2:1]=[C:2] |
vinylsilane |
alkenyl_stannane |
functional:120 |
[Sn;D4;z1]-;!@[C;z2:1]=[C:2] |
vinylstannane |
alkenyl_zinc |
functional:115 |
[Zn;D2](-[F,Cl,Br,I])-[C;z2:1]=[C:2] |
vinylzinc |
alkoxide |
functional:232 |
[O;D1;z1;x0;-:1]-[C;z1:2] |
RO- |
alkyl_boronic_acid |
functional:14 |
[B;D3;z1;x2](-[O;D1])(-[O;D1])-;!@[C;z1;x1:1] |
RB(OH)2 on sp3 carbon |
alkyl_boronic_ester |
functional:61 |
[B;D3;z1;x2](-[O;D2;x1])(-[O;D2;x1])-;!@[C;z1;x1:1] |
RB(OR')2 on sp3 carbon |
alkyl_bromide |
functional:10 |
[Br;D1][C;z1;x1:1] |
R-Br on sp3 carbon |
alkyl_carboxylic_acid |
functional:79 |
[O;D1;z1;x0]-[C;z2;x2;D3:1](=[O:2])-[C;z1:3] |
R-COOH on sp3 carbon |
alkyl_chloride |
functional:9 |
[Cl;D1][C;z1;x1:1] |
R-Cl on sp3 carbon |
alkyl_fluoride |
functional:46 |
[F;D1][C;z1;x1:1] |
R-F on sp3 carbon; not a leaving group, a metabolic-stability flag |
alkyl_grignard |
functional:110 |
[Mg;D2](-[F,Cl,Br,I])-[C;z1:1] |
RMgX on sp3 carbon |
alkyl_halide |
functional:45 |
[Cl,Br,I;D1][C;z1;x1:1] |
R-X on sp3 carbon, the SN2 electrophile |
alkyl_hydrazine |
functional:139 |
[N;D1;z1;x1:1]-[N;D2;z1;x1:2]-[C;z1:3] |
R-NH-NH2 on sp3 carbon |
alkyl_iodide |
functional:11 |
[I;D1][C;z1;x1:1] |
R-I on sp3 carbon |
alkyl_mesylate |
functional:59 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;z1;x1:1])-[C;D1] |
ROMs |
alkyl_molander_salt |
functional:67 |
[B;D4;z1;x3;-](-[F])(-[F])(-[F])-;!@[C;z1:1] |
RBF3- on sp3 carbon |
alkyl_stannane |
functional:121 |
[Sn;D4;z1]-;!@[C;z1;D2,D3,D4:1] |
RSnR3 on sp3 carbon, terminal methyls excluded |
alkyl_sulfonate |
functional:243 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;z1;x1:1])-[C] |
ROSO2R' on sp3 carbon, any R'. The SN2 leaving group as one class |
alkyl_tosylate |
functional:60 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;z1;x1:1])-[C;a]:1:[C;a;D2]:[C;a;D2]:[C;a](-[C;D1]):[C;a;D2]:[C;a;D2]:1 |
ROTs |
alkyl_triflate |
functional:58 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;z1;x1:1])-[C;D4](-[F])(-[F])-[F] |
ROTf on sp3 carbon, a strong SN2 leaving group |
alkyl_zinc |
functional:113 |
[Zn;D2](-[F,Cl,Br,I])-[C;z1:1] |
RZnX, the Negishi nucleophile |
alkyne |
functional:4 |
[C;z3;x0;D2:1]#[C;x0;D2:2] |
internal C#C |
alkynyl_boronic_acid |
functional:64 |
[B;D3;z1;x2](-[O;D1])(-[O;D1])-;!@[C;z3;x1:1]#[C:2] |
alkynylboronic acid |
alkynyl_boronic_ester |
functional:65 |
[B;D3;z1;x2](-[O;D2;x1])(-[O;D2;x1])-;!@[C;z3;x1:1]#[C:2] |
alkynylboronate ester |
alkynyl_bromide |
functional:53 |
[Br;D1][C;z3;x1:1]#[C:2] |
C(sp)-Br |
alkynyl_carboxylic_acid |
functional:82 |
[O;D1;z1;x0]-[C;z2;x2;D3:1](=[O:2])-[C;z3;x0:3]#[C:4] |
propiolic-type acid |
alkynyl_chloride |
functional:52 |
[Cl;D1][C;z3;x1:1]#[C:2] |
C(sp)-Cl |
alkynyl_fluoride |
functional:51 |
[F;D1][C;z3;x1:1]#[C:2] |
C(sp)-F; z3 is genuine sp here |
alkynyl_iodide |
functional:54 |
[I;D1][C;z3;x1:1]#[C:2] |
C(sp)-I |
alkynyl_molander_salt |
functional:69 |
[B;D4;z1;x3;-](-[F])(-[F])(-[F])-;!@[C;z3;x1:1]#[C:2] |
alkynyl trifluoroborate |
alkynyl_silane |
functional:124 |
[Si;D4]-;!@[C;z3:1]#[C:2] |
TMS-protected alkyne |
allyl_halide |
functional:223 |
[Cl,Br,I;D1:1]-[C;z1;x1:2]-[C;z2:3]=[C;z2:4] |
X-C-C=C, the allylic SN2/SN2' substrate |
alpha_haloester |
functional:74 |
[O;D2;x0:1]-[C;D3;x2;z2:2](=[O:3])-[C;z1;D2,D3;x1:4]-[Cl,Br,I;D1] |
alpha-halo ester |
alpha_haloketone |
functional:73 |
[O;z2;x0:1]=[C;D3;x1:2]-[C;z1;D2,D3;x1:3]-[Cl,Br,I;D1] |
alpha-halo ketone, the Hantzsch thiazole electrophile |
alpha_heteroatom_halide |
functional:225 |
[Cl,Br,I;D1:1]-[C;z1;h1,h2:2]-[N,O,S;z1:3] |
X-C-Het, the MOM-chloride class: an alkylating agent far more reactive than alkyl_halide says |
alpha_ketone |
functional:72 |
[O;z2;x0:1]=[C;D3;x1:2]-[C;z1;D1,D2;x0:3] |
ketone with an enolizable alpha CH2/CH3 |
amidine |
functional:152 |
[N;D1;z1;x0:1]-[C;D3;z2;x2:2]=[N;D1:3] |
RC(=NH)NH2, the pyrimidine partner |
amidoxime |
functional:151 |
[N;D1;z2;x0:1]=[C;D3;x2:2]-[N;D2;z1;x1:3]-[O;D1:4] |
RC(=NH)NHOH, the 1,2,4-oxadiazole precursor |
amino_alcohol |
functional:159 |
[N;D1;z1;x0:1]-[C;z1:2]-[C;z1:3]-[O;D1:4] |
1,2-amino alcohol |
aminopyridine |
functional:158 |
[N;D1;z1;x0:1]-[C;a:2]:[N;a;h0;D2:3] |
2-aminoazine, the GBB partner |
ammonium |
functional:235 |
[N;z1;x0;+;h1,h2,h3:1] |
The protonated amine. h1,h2,h3 is what distinguishes it from a quaternary salt |
anhydride |
functional:96 |
[C;z2;x2;D3:1](=[O:2])-[O;D2;x0]-[C;z2;x2;D3:3]=[O:4] |
R-CO-O-CO-R; also matches ester twice |
aniline_ortho_ch |
functional:168 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a;D2:3] |
Ar-NH2 with a free ortho CH |
anthranilic_acid |
functional:150 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[C;z2;x2;D3:4](=[O:5])-[O;D1] |
2-aminobenzoic acid |
arene_ch |
functional:41 |
[C;a;D2:1] |
an aromatic CH, the electrophilic-substitution site |
aryl_boronic_acid |
functional:12 |
[B;D3;z1;x2](-[O;D1])(-[O;D1])-;!@[C;a:1] |
ArB(OH)2 |
aryl_boronic_ester |
functional:13 |
[B;D3;z1;x2](-[O;D2;x1])(-[O;D2;x1])-;!@[C;a:1] |
ArB(OR)2, pinacol boronate and its kin |
aryl_bromide |
functional:7 |
[Br;D1]-[C;a:1] |
Ar-Br |
aryl_bromide_iodide |
functional:44 |
[Br,I;D1]-[C;a:1] |
Ar-Br or Ar-I, the halides that couple without a specialist ligand |
aryl_carbonate |
functional:89 |
[O;D2:1]-[C;z2;x3;D3:2](=[O:3])-[O;D2;x0]-[C;a] |
aryl carbonate; the aryloxide is the leaving group |
aryl_carboxylic_acid |
functional:80 |
[O;D1;z1;x0]-[C;z2;x2;D3:1](=[O:2])-[C;a:3] |
Ar-COOH |
aryl_chloride |
functional:6 |
[Cl;D1]-[C;a:1] |
Ar-Cl |
aryl_ether |
functional:185 |
[O;D2;z1;x0:1](-[C;a:2])[C;z1,a:3] |
Ar-O-R and Ar-O-Ar. Separate from dialkyl_ether because only this one is an SNAr and Ullmann product and a demethylation substrate |
aryl_fluoride |
functional:5 |
[F;D1]-[C;a:1] |
Ar-F, an SNAr electrophile rather than a cross-coupling one |
aryl_grignard |
functional:111 |
[Mg;D2](-[F,Cl,Br,I])-[C;a:1] |
ArMgX |
aryl_halide |
functional:43 |
[Cl,Br,I;D1]-[C;a:1] |
Ar-X, the cross-coupling electrophile; F excluded, it does SNAr instead |
aryl_hydrazine |
functional:140 |
[N;D1;z1;x1:1]-[N;D2;z1;x1:2]-[C;a:3] |
Ar-NH-NH2, no constraint on the ring beyond the attachment carbon |
aryl_hydrazine_ortho_ch |
functional:141 |
[N;D1;z1;x1:1]-[N;D2;z1;x1:2]-[C;a:3]:[C;a;D2:4] |
Ar-NH-NH2 with a free ortho CH, which an indolization consumes |
aryl_iodide |
functional:8 |
[I;D1]-[C;a:1] |
Ar-I |
aryl_mesylate |
functional:56 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;a:1])-[C;D1] |
ArOMs |
aryl_molander_salt |
functional:66 |
[B;D4;z1;x3;-](-[F])(-[F])(-[F])-;!@[C;a:1] |
ArBF3-, the air-stable trifluoroborate |
aryl_silane |
functional:122 |
[Si;D4]-;!@[C;a:1] |
ArSiR3, the Hiyama nucleophile |
aryl_stannane |
functional:119 |
[Sn;D4;z1]-;!@[C;a:1] |
ArSnR3, the Stille nucleophile |
aryl_sulfonate |
functional:242 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;a:1])-[C] |
ArOSO2R for any R -- triflate, mesylate, tosylate, besylate. The three named rows answer "which pseudohalide"; this one answers "does this couple", which is the question a coupling row asks |
aryl_thiol |
functional:129 |
[S;x0;D1;z1:1]-[C;a:2] |
Ar-SH |
aryl_tosylate |
functional:57 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;a:1])-[C;a]:1:[C;a;D2]:[C;a;D2]:[C;a](-[C;D1]):[C;a;D2]:[C;a;D2]:1 |
ArOTs |
aryl_triflate |
functional:55 |
[S;D4](=[O])(=[O])(-[O;D2]-;!@[C;a:1])-[C;D4](-[F])(-[F])-[F] |
ArOTf, the pseudohalide that couples like an aryl bromide |
aryl_zinc |
functional:114 |
[Zn;D2](-[F,Cl,Br,I])-[C;a:1] |
ArZnX |
azetidine |
functional:238 |
[N;D2;z1;x0;r4;h1:1]([C;z1;r4:2])[C;z1;r4:3] |
The four-membered NH amine |
azide |
functional:102 |
[N;x1;D2:1]=[N;+:2]=[N;-:3] |
R-N3 |
azine_n_oxide |
functional:206 |
[N;a;D3;+:1]-[O;D1;z1;-:2] |
The pyridine N-oxide, an activated ring for C-H functionalization. The oxygen is NUMBERED: a deoxygenation omits it from its own product side, and leaving it unnumbered would delete it from every other template too |
azinone |
functional:132 |
[O;z2;x0:1]=[C;z2;x2;D3;r6:2](-[C,N;z2,z4;r6:3])-[N;z1;D2;r6:4] |
aromatizable cyclic amide; the sp2/aromatic flank excludes a saturated lactam |
aziridine_nh |
functional:94 |
[N;D2;z1;x0;h1;r3:1] |
aziridine N-H, matched alone so a ring opening leaves the ring intact |
azo |
functional:105 |
[N;D2;x1:1]=[N;D2;x1:2] |
R-N=N-R |
benzyl_halide |
functional:222 |
[Cl,Br,I;D1:1]-[C;z1;x1;h1,h2:2]-[C;a:3] |
Ar-CH2-X. alkyl_halide already matches it; this says the SN2 is a benzylic one, which is a different rate and a different selectivity |
benzylic_ch |
functional:42 |
[C;z1;h1,h2;D2,D3:1]-[C;a:2] |
an sp3 carbon bearing hydrogen next to a ring. D2,D3 excludes a TOLUENE METHYL, which is a D1 -- so benzylic_bromination does not reach one |
beta_arylethylamine |
functional:157 |
[N;D1;z1;x0:1]-[C;z1:2]-[C;z1:3]-[C;a:4]:[C;a;D2:5] |
the Pictet-Spengler substrate |
beta_ketoester |
functional:78 |
[O;z2;x0:1]=[C;D3;x1:2]-[C;z1;D2;x0:3]-[C;z2;x2;D3:4](=[O:5])-[O;D2] |
beta-keto ester |
beta_lactam |
functional:239 |
[N;D2,D3;z1;r4:1]-[C;D3;z2;r4:2]=[O;D1;x0:3] |
The four-membered lactam. D2,D3 because a fused penicillin or cephalosporin nitrogen is D3 and D2 alone reaches only the monocyclic model compound |
biaryl_aniline |
functional:95 |
[N;D2;z1;x0:1](-[C;a:2])-[C;a:3] |
Ar-NH-Ar |
boronate_alkyl_bromide |
functional:117 |
[Br;D1]-[C;z1;D2;x2:1]-[B:2] |
B-CH2-Br |
boronate_alkyl_chloride |
functional:116 |
[Cl;D1]-[C;z1;D2;x2:1]-[B:2] |
B-CH2-Cl, the one-carbon SN2 electrophile |
boronate_alkyl_iodide |
functional:118 |
[I;D1]-[C;z1;D2;x2:1]-[B:2] |
B-CH2-I |
bridged_diaryl |
functional:181 |
[C,N;a:1]-;!@[C,O,N,S:2]-;!@[C,N;a:3] |
two rings joined through one bridging atom |
carbamate |
functional:191 |
[N:1]-[C;D3;z2;x3:2](=[O;D1;z2;x0:3])-[O;D2;z1:4]-[C:5] |
N-CO-O-R, the Boc/Cbz/Fmoc backbone. Reported wherever it occurs, unlike protective.tsv, which only names the ones it can cleave |
carbamoyl_chloride |
functional:91 |
[Cl;D1]-[C;z2;x3;D3:1](=[O:2])-[N;D2,D3:3] |
R2N-CO-Cl |
carbamoyl_fluoride |
functional:92 |
[F;D1]-[C;z2;x3;D3:1](=[O:2])-[N;D2,D3:3] |
R2N-CO-F |
carbodiimide |
functional:217 |
[N;D2;z2:1]=[C;D2;z5:2]=[N;D2;z2:3] |
N=C=N, the DCC/EDC coupling reagent. z5 is the cumulated-double centre; chython 2 wrote z3 here and V3's z3 is sp and nothing else |
carbonate |
functional:193 |
[C:1]-[O;D2;z1:2]-[C;D3;z2;x3:3](=[O;D1;z2;x0:4])-[O;D2;z1:5]-[C:6] |
R-O-CO-O-R, both oxygens esterified |
carboxylate |
functional:230 |
[O;D1;z1;x0;-:1]-[C;D3;z2:2]=[O;D1;z2;x0:3] |
The deprotonated acid. carboxylic_acid cannot match it, its own oxygen being neutral by omission, so a registration salt reports no acid at all without this row |
carboxylic_acid |
functional:22 |
[O;D1;z1;x0:3][C;z2;x2;D3:1]=[O:2] |
R-COOH; the hydroxyl is the leaving group |
catechol |
functional:174 |
[O;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[O;D1;z1;x0:4] |
1,2-dihydroxyarene |
chloroazine |
functional:133 |
[Cl;D1]-[C;a:1]:[N;a;D2:2] |
Cl on an aromatic carbon next to a ring N; hydrolyses to the azinone |
chloroformate |
functional:86 |
[Cl;D1]-[C;z2;x3;D3:1](=[O:2])-[O;D2:3] |
RO-CO-Cl, the carbamoylation reagent |
chlorosilane |
functional:229 |
[F,Cl,Br,I;D1:1]-[Si;D4:2] |
Si-X, the silylating agent |
cyclic_carbamate |
functional:192 |
[N;D2,D3;z1;r5,r6:1]-[C;D3;z2;x3;r5,r6:2](=[O;D1;z2:3])-[O;D2;z1;r5,r6:4] |
The oxazolidinone/cyclic-carbamate ring, which is a scaffold rather than a protected amine |
cyclic_carboxylic_acid |
functional:83 |
[O;D1;z1;x0]-[C;z2;x2;D3:1](=[O:2])-[C;z1;r5,r6:3] |
COOH on a saturated 5- or 6-ring |
dialkyl_ether |
functional:184 |
[O;D2;z1;x0:1]([C;z1:2])[C;z1:3] |
R-O-R, both sp3. x0 and both carbons stated: the bare [O;D2;z1] is also every ester O, every anisole and every silyl ether |
diaryl |
functional:180 |
[C,N;a:1]-;!@[C,N;a:2] |
two rings joined by an acyclic single bond |
diazo |
functional:103 |
[C;z2:1]=[N;+;D2:2]=[N;-;D1:3] |
R2C=N2 |
diazonium |
functional:104 |
[C;a:1]-[N;+;D2:2]#[N;D1:3] |
ArN2+ |
difluoromethoxy |
functional:208 |
[F:1][C;D3;z1;x3:2]([F:3])-[O;D2:4] |
OCHF2 |
difluoromethyl |
functional:173 |
[C;D3;z1;x2:1](-[F:2])-[F:3] |
-CHF2 |
disulfide |
functional:130 |
[S;D2;z1:1]-[S;D2;z1:2] |
R-S-S-R |
enal |
functional:71 |
[O;z2;x0:1]=[C;D2;x1;z2:2]-[C;z2;x0:3]=[C;x0:4] |
alpha,beta-unsaturated aldehyde |
enamine |
functional:182 |
[C;z2;D2,D3:1]=[C;z2;D2,D3:2]-[N;z1;D2,D3:3] |
C=C-N, the hydrogenation and Stork substrate |
enol |
functional:188 |
[O;D1;z1;x0;h1:1]-[C;z2:2]=[C;z2:3] |
HO-C=C. z2 on both carbons, so a phenol -- aromatic, not z2 -- is not one |
enol_ether |
functional:183 |
[C;z2;D2,D3:1]=[C;z2;D2,D3:2]-[O;D2:3] |
C=C-O-R |
enone |
functional:194 |
[C;z2:1]=[C;z2:2]-[C;D3;z2;x1:3]=[O;D1;x0:4] |
C=C-C=O, the Michael acceptor. The conjugation is the group: neither ketone nor alkene alone says a molecule is electrophilic at the beta carbon |
epoxide |
functional:39 |
[O;D2;r3:1]1-[C;r3:2]-[C;r3:3]-1 |
oxirane |
ester |
functional:24 |
[O;z2;x0:1]=[C;D3;x2;z2:2]-[O;D2;x0] |
R-CO-OR'; the alkoxy is the leaving group |
fluoroformate |
functional:87 |
[F;D1]-[C;z2;x3;D3:1](=[O:2])-[O;D2:3] |
RO-CO-F |
furan_o |
functional:204 |
[O;a;D2:1] |
The aromatic divalent oxygen of a furan, oxazole or isoxazole |
fused_aromatic |
functional:178 |
[A;a;D3:1](:[A;a:2])(:[A;a:3]):[A;a:4] |
a ring-fusion atom: three aromatic neighbours |
gem_dihalide |
functional:224 |
[Cl,Br,I;D1:1]-[C;z1:2]-[Cl,Br,I;D1:3] |
Two halides on one carbon. Fluorine is excluded because a gem-difluoride is difluoromethyl and not an alkylating agent |
guanidine |
functional:107 |
[N;z1;x0:1]-[C;!R:2](-[N;z1;x0:3])=[N;x0:4] |
acyclic guanidine |
hemiketal |
functional:187 |
[O;D1;z1;x0;h1:1]-[C;z1;x2:2]-[O;D2;z1:3] |
HO-C(-OR), the ring-opened sugar form |
hindered_aryloxyl |
functional:251 |
[O;D1;h0;z1:1]-[C;a:2](:[C;a:3]-[C;D4;z1:4]):[C;a:5]-[C;D4;z1:6] |^1:0| |
Ar-O• with a quaternary carbon at BOTH ortho positions, which is what makes it isolable; the unhindered phenoxyl radical is a decoy |
hydrazide |
functional:161 |
[N;D1;z1;x1:1]-[N;D2;z1;x1:2]-[C;z2;x2:3]=[O:4] |
R-CO-NH-NH2 |
hydrazine |
functional:215 |
[N;z1;x1:1]-[N;z1;x1:2] |
N-N single bond, both sp3. A hydrazide matches this too and hydrazide names it more precisely |
hydrazone |
functional:142 |
[C;z2:1]=[N;D2;z2;x1:2]-[N;D2;z1;x1:3] |
C=N-NH-R |
hydrazyl |
functional:252 |
[N;D2;h0;z1:1](-[C;a:2])-[N;D3;z1:3](-[C;a:4])-[C;a:5] |^1:0| |
Ar2N-N•-Ar, the DPPH class: three aryl rings to delocalise over, and the trialkyl hydrazyl with none of them is a decoy |
hydroxamic_acid |
functional:160 |
[O;D1;z1;x1:1]-[N;D2;z1;x1:2]-[C;z2;x2:3]=[O:4] |
R-CO-NH-OH |
imidazole |
functional:136 |
[N;h1;D2;a;r5:1]:[A:2]:[N;h0;D2;r5:3] |
N-H and N separated by one ring atom |
imidazolyl_carbonate |
functional:90 |
[O;D2:1]-[C;z2;x3;D3:2](=[O:3])-[N;a;D3;r5]1:[C;a]:[N;a]:[C;a]:[C;a]:1 |
CDI adduct of an alcohol; here the azole nitrogen leaves |
imine |
functional:213 |
[N;D2;z2;x0:1]=[C;z2:2] |
R-N=C, the reductive-amination intermediate and the aza-Michael acceptor. x0 excludes the oxime and the hydrazone, which have their own rows |
imine_nh |
functional:214 |
[N;D1;z2;x0;h1:1]=[C;z2:2] |
HN=C, the free imine |
isocyanate |
functional:34 |
[N;z2;x0;D2:1]=[C:2]=[O:3] |
R-N=C=O |
isocyano |
functional:106 |
[N;+;D2;x0:1]#[C;-;D1:2] |
R-NC, charge-separated |
isothiocyanate |
functional:109 |
[N;z2;x0;D2:1]=[C:2]=[S;D1:3] |
R-N=C=S |
isoxazole |
functional:137 |
[O;a;D2;r5:1]:[N;a;D2;r5:2] |
adjacent aromatic O/N pair |
ketone |
functional:21 |
[O;z2;x0:1]=[C;D3;x1;z2:2] |
R2C=O |
lactam_1_halide |
functional:244 |
[F,Cl,Br,I;D1]-[C;z2;r6:1]1=[C,N;z2;M]-[C;D3;z2;M]-[N;D3;M]-[C,N;z2,z4;M]=,:[C,N;z2,z4;M]1 |
Activated C(sp2)-X on an N-substituted six-membered lactam, halide at C4 of a 2-pyridinone. Every ring atom but the reacting carbon is masked, so a reaction row bonds to :1 and restates nothing |
lactam_2_halide |
functional:245 |
[F,Cl,Br,I;D1]-[C;z2;r6:1]=1-[N;D3;M]-[C;D3;z2;M]-[C,N;z2,z4;M]=,:[C,N;z2,z4;M]-[C,N;z2;M]=1 |
Activated C(sp2)-X on an N-substituted six-membered lactam, halide at C6 of a 2-pyridinone, adjacent to the ring nitrogen |
lactam_3_halide |
functional:246 |
[F,Cl,Br,I;D1]-[C;z2;r6:1]=1-[N;D3;M]-[C,N;z2,z4;M]=,:[C,N;z2,z4;M]-[C;D3;z2;M]-[C,N;z2;M]=1 |
Activated C(sp2)-X on an N-substituted six-membered lactam, halide at C2 of a 4-pyridinone, adjacent to the ring nitrogen |
lactam_4_halide |
functional:247 |
[F,Cl,Br,I;D1]-[C;z2;r6:1]=1-[C;D3;z2;M]-[N;D3;M]-[C,N;z2,z4;M]=,:[C,N;z2,z4;M]-[C,N;z2;M]=1 |
Activated C(sp2)-X on an N-substituted six-membered lactam, halide at C3 of a 2-pyridinone, adjacent to the carbonyl |
lactam_5_halide |
functional:248 |
[F,Cl,Br,I;D1]-[C;z2;r6:1]1=[C,N;z2;M]-[N;D3;M]-[C,N;z2,z4;M]=,:[C,N;z2,z4;M]-[C;D3;z2;M]1 |
Activated C(sp2)-X on an N-substituted six-membered lactam, halide at C3 of a 4-pyridinone, adjacent to the carbonyl |
lactam_6_halide |
functional:249 |
[F,Cl,Br,I;D1]-[C;z2;r6:1]1=[C,N;z2;M]-[N;D3;M]-[C;D3;z2;M]-[C,N;z2,z4;M]=,:[C,N;z2,z4;M]1 |
Activated C(sp2)-X on an N-substituted six-membered lactam, halide at C5 of a 2-pyridinone |
maleimide |
functional:177 |
[N;r5:1]1-[C;z2;r5:2](=[O:3])-[C;z2;r5:4]=[C;z2;r5:5]-[C;z2;r5:6]1=[O:7] |
maleimide, the thiol-conjugation warhead |
metalate_carbanion |
functional:241 |
[Mg,Zn,Cu,Li;D1;+:1]-[C:2] |
The ionic spelling of an organometallic, which the neutral alkyl_grignard and alkyl_zinc rows cannot match |
methyl_ester |
functional:170 |
[O;z2;x0:1]=[C;D3;x2;z2:2]-[O;D2;x0:3]-[C;D1] |
R-CO-OMe; distinct saponification and transesterification behaviour |
n_halo_imide |
functional:227 |
[Cl,Br,I;D1:1]-[N;D3:2] |
N-X, the NBS/NCS halogen source |
n_hydroxylamine |
functional:216 |
[O;D1;z1;x1;h1:1]-[N;z1;x1:2]-[C;z1,a:3] |
HO-N with carbon on the nitrogen. The carbon is stated to exclude the hydroxamic acid, whose nitrogen carries a carbonyl |
n_substituted_azole |
functional:205 |
[N;a;D3:1]-[C;z1,a:2] |
The substituted pyrrole-type nitrogen -- an N-alkylated or N-arylated azole, as distinct from the nh_azole that could still be alkylated |
nh_thiourea |
functional:156 |
[N;z1;h1,h2;!R:1]-[C;D3;z2;x3:2](=[S;D1:3])-[N;z1;h1,h2;!R:4] |
the thiourea half of the same |
nh_urea |
functional:155 |
[N;z1;h1,h2;!R:1]-[C;D3;z2;x3:2](=[O:3])-[N;z1;h1,h2;!R:4] |
acyclic urea with an N-H on both nitrogens, the Biginelli subset |
nitrile |
functional:32 |
[N;D1;z3;x0:1]#[C;D2;x1:2] |
R-CN; z3 here is a genuine sp nitrogen |
nitro |
functional:33 |
[N;D3;x2;+:1]([O;-:2])=[O:3] |
R-NO2, charge-separated as chython stores it |
nitroso |
functional:108 |
[N;D2;z2:1]=[O;D1:2] |
R-N=O |
nitroxide |
functional:250 |
[O;D1;h0;z1:1]-[N;D3;z1:2](-[C;z1,z4;D3,D4:3])-[C;z1,z4;D3,D4:4] |^1:0| |
R2N-O•, the radical on oxygen -- TEMPO and its kin. D3,D4 on both alpha carbons is the isolability: a nitroxide with an alpha hydrogen disproportionates, so dimethylnitroxide is a decoy and not a match. The hydroxylamine and the oxoammonium cation are the same skeleton at the other two oxidation states |
o_aminobenzaldehyde |
functional:149 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[C;D2;z2;x1:4]=[O:5] |
2-aminobenzaldehyde, the Friedlander partner |
o_aminophenol |
functional:147 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[O;D1:4] |
2-aminophenol |
o_aminothiophenol |
functional:148 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[S;D1:4] |
2-aminothiophenol |
o_diaminoarene |
functional:146 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[N;D1,D2;z1;x0:4] |
ortho-phenylenediamine |
o_haloaniline |
functional:169 |
[N;D1;z1;x0:1]-[C;a:2]:[C;a:3]-[Cl,Br,I;D1] |
2-haloaniline, the Larock indole substrate |
oxetane |
functional:237 |
[O;D2;z1;r4:1]([C;z1;r4:2])[C;z1;r4:3] |
The four-membered ether, a carbonyl bioisostere and a slow electrophile |
oxime |
functional:162 |
[O;D1;z1;x1:1]-[N;D2;z2;x1:2]=[C:3] |
C=N-OH |
pentafluorosulfanyl |
functional:209 |
[S;D6:1]([F:2])([F:3])([F:4])([F:5])-[C:6] |
SF5, the CF3 replacement |
peroxide |
functional:176 |
[O;D2;z1:1]-[O;D2;z1:2] |
R-O-O-R |
phenol |
functional:18 |
[O;D1;z1;x0:1]-[C;a:2] |
Ar-OH |
phenoxide |
functional:233 |
[O;D1;z1;x0;-:1]-[C;a:2] |
ArO- |
phosphate_ester |
functional:210 |
[C:1]-[O;D2:2]-[P;D4:3](=[O;D1:4])(-[O;D2:5])-[O;D2:6] |
R-O-PO(OR)(OR), three oxygens on phosphorus |
phosphine_oxide |
functional:211 |
[P;D4:1](=[O;D1;x1:2])([C:3])([C:4])[C:5] |
R3P=O, the Wittig and Mitsunobu byproduct. x1 on the oxygen: its only neighbour is phosphorus, which is a heteroatom |
phosphonate |
functional:126 |
[P;D4;x3](=[O])(-[O;D2;x1])(-[O;D2;x1])-[C:1] |
(RO)2P(=O)R, the HWE reagent |
phosphonic_acid |
functional:212 |
[O;D1;z1;h1:1]-[P;D4:2](=[O;D1:3])-[O;D1;z1;h1:4] |
R-PO(OH)2 |
phosphonium_ylide |
functional:125 |
[P;D4;z2;x0]=[C:1] |
R3P=CR2, the Wittig reagent |
phosphorus_halide |
functional:228 |
[F,Cl,Br,I;D1:1]-[P:2] |
P-X |
polyarene |
functional:179 |
[A;a:1]:[A;a;D3:2](:[A;a:3]):[A;a:4]:[A;a;D3:5](:[A;a:6]):[A;a:7] |
two fusion atoms one atom apart, as in a linear triarene |
primary_alcohol |
functional:15 |
[O;D1;z1;x0:1][C;D2;x1;z1:2] |
R-CH2-OH |
primary_amide |
functional:30 |
[N;D1;z1;x0:1][C;z2;x2;D2,D3:2]=[O:3] |
R-CO-NH2. D2,D3 because a FORMAMIDE carbonyl is D2, hydrogens not counting toward D, and D3 alone reported formamide as carrying no group at all |
primary_amidine_amine |
functional:93 |
[N;D1;z1;x0:1]-[C;z2:2]=[N:3] |
NH2 on an sp2 carbon that also carries C=N |
primary_amine |
functional:25 |
[N;D1;z1;x0:1][C;z1:2] |
R-NH2 on sp3 carbon |
primary_aniline |
functional:26 |
[N;D1;z1;x0:1][C;a:2] |
Ar-NH2 |
pyrazole |
functional:135 |
[N;h1;D2;a;r5:1]:[N;h0;D2;r5:2] |
adjacent N-H/N pair |
pyridazine |
functional:138 |
[N;a;D2;r6:1]:[N;a;D2;r6:2] |
adjacent aromatic N pair in a 6-ring |
pyridine_n |
functional:40 |
[N;a;D2;h0:1] |
an aromatic nitrogen with no hydrogen, the N-oxidation substrate |
pyrrole |
functional:134 |
[N;h1;D2;a;r5:1] |
azole N-H; the H stays out of a template for tautomerism |
quaternary_ammonium |
functional:236 |
[N;D4;z1;x0;+;h0:1] |
R4N+, a phase-transfer catalyst rather than a protonation state |
redox_active_ester |
functional:128 |
[C;z1:1]-[C;z2;x2;D3:2](=[O:3])-[O;D2;x1]-[N;D3;x1;r5](-[C;z2;r5]=[O])-[C;z2;r5]=[O] |
NHPI/NHS ester; decarboxylative coupling transfers the alkyl |
secondary_alcohol |
functional:16 |
[O;D1;z1;x0:1][C;D3;x1;z1:2] |
R2CH-OH |
secondary_amide |
functional:31 |
[N;D2;z1;x0:1][C;z2;x2;D2,D3:2]=[O:3] |
R-CO-NH-R', N-methylformamide included -- see primary_amide on D2,D3 |
secondary_amine |
functional:27 |
[N;D2;z1;x0:1]([C;z1:2])[C;z1:3] |
R2NH, both substituents sp3 carbon |
secondary_aniline |
functional:28 |
[N;D2;z1;x0:1]([C;a:2])[C;z1:3] |
Ar-NH-R |
silyl_ether |
functional:189 |
[Si;D4:1]-[O;D2;z1:2]-[C:3] |
R3Si-O-R, a protected alcohol. protective.tsv removes the named ones; this reports any |
succinimidyl_carbonate |
functional:88 |
[O;D2:1]-[C;z2;x3;D3:2](=[O:3])-[O;D2;x1]-[N;D3;x1;r5](-[C;z2;r5]=[O])-[C;z2;r5]=[O] |
NHS/DSC carbonate; numbered like chloroformate so it drops into the same rows |
sulfamate |
functional:199 |
[N:1]-[S;D4;x4:2](=[O;D1:3])(=[O;D1:4])-[O;D2:5]-[C:6] |
N-SO2-O-R |
sulfamide |
functional:198 |
[N:1]-[S;D4;x4:2](=[O;D1:3])(=[O;D1:4])-[N:5] |
N-SO2-N, nitrogen on both sides |
sulfinamide |
functional:201 |
[S;D3;z2:1](=[O;D1:2])(-[N:3])[C:4] |
R-S(=O)-N, the Ellman auxiliary and the sulfoximine precursor |
sulfinate_ester |
functional:202 |
[S;D3;z2:1](=[O;D1:2])(-[O;D2:3]-[C:4])[C:5] |
R-S(=O)-O-R |
sulfo |
functional:97 |
[S;D4;x3:1](=[O:2])(=[O:3])-[O;D1:4] |
R-SO3H, distinct from a sulfonyl halide or a sulfonamide |
sulfonamide |
functional:100 |
[S;D4;x3:1](=[O:2])(=[O:3])-[N;z1:4] |
R-SO2-NR2 |
sulfonate |
functional:231 |
[O;D1;z1;-:1]-[S;D4:2](=[O;D1:3])=[O;D1:4] |
The deprotonated sulfonic acid |
sulfonate_ester |
functional:197 |
[C:1]-[O;D2;z1:2]-[S;D4:3](=[O;D1:4])=[O;D1:5] |
R-O-SO2-R, any sulfonate ester. The named ones each have a row; this catches the rest |
sulfone |
functional:38 |
[S;D4:1](=[O:2])(=[O:3])([C:4])[C:5] |
R-SO2-R' |
sulfonyl_anhydride |
functional:101 |
[S;D4;x3:1](=[O:2])(=[O:3])-[O;D2]-[S;D4;x3](=[O])=[O] |
R-SO2-O-SO2-R |
sulfonyl_chloride |
functional:98 |
[Cl;D1]-[S;D4:1](=[O:2])=[O:3] |
R-SO2Cl |
sulfonyl_fluoride |
functional:99 |
[F;D1]-[S;D4:1](=[O:2])=[O:3] |
R-SO2F |
sulfonylhydrazide |
functional:144 |
[N;D1;z1;x1:1]-[N;D2;z1;x2:2]-[S;D4;x3:3](=[O:4])=[O:5] |
R-SO2-NH-NH2, the reagent that makes the above |
sulfonylhydrazone |
functional:143 |
[C;z2:1]=[N;D2;z2;x1:2]-[N;D2;z1;x2:3]-[S;D4;x3](=[O])=[O] |
tosylhydrazone and kin, the Bamford-Stevens diazo precursor |
sulfoxide |
functional:37 |
[S;D3;z2:1](=[O:2])([C:3])[C:4] |
R-S(=O)-R' |
sulfoximine |
functional:200 |
[S;D4;z5:1](=[O;D1:2])(=[N:3])([C:4])[C:5] |
R2S(=O)=N, the sulfone bioisostere. A stereocentre at sulfur, which is why the substituents are numbered rather than left to a template |
terminal_alkene |
functional:1 |
[C;z2;x0;D1:1]=[C;z2;x0;D2,D3:2] |
monosubstituted C=C |
terminal_alkyne |
functional:3 |
[C;z3;x0;D1:1]#[C;x0;D2:2] |
monosubstituted C#C, the Sonogashira nucleophile |
terminal_epoxide |
functional:171 |
[O;D2;r3:1]1-[C;r3:2]-[C;r3;D2:3]-1 |
epoxide oriented for opening: :3 is the CH2 a nucleophile attacks |
tertiary_alcohol |
functional:17 |
[O;D1;z1;x0:1][C;D4;x1;z1:2] |
R3C-OH |
tertiary_alcohol_with_alpha_h |
functional:70 |
[O;D1;z1;x0:1]-[C;D4;x1;z1:2]-[C;z1;h1,h2:3] |
R3C-OH with an eliminable alpha C-H, the dehydration substrate |
tertiary_amide |
functional:190 |
[N;D3;z1;x0:1]-[C;D2,D3;z2;x2:2]=[O;D1;z2;x0:3] |
R-CO-NR2, the level primary_amide and secondary_amide left out. x0 on the nitrogen because an amide N's three neighbours are all CARBON; x2 on the carbonyl is what excludes a carbamate and a urea, whose carbonyl is x3 |
tertiary_amine |
functional:29 |
[N;D3;z1;x0:1]([C;z1,a:2])([C;z1,a:3])[C;z1,a:4] |
R3N, the N-oxidation substrate. The three substituents are stated because the bare [N;D3;z1;x0] also matched every TERTIARY AMIDE and every carbamate -- an N-Boc amine reported as an amine, and nitrogen_oxidation offered to oxidize DMF. primary_amine and secondary_amine always stated theirs |
thioamide |
functional:145 |
[S;z2;x0;D1:1]=[C;D2,D3;x2:2]-[N;D1:3] |
R-CS-NH2, the Hantzsch thiazole partner. D2,D3 as in primary_amide |
thiocarbamate |
functional:219 |
[N:1]-[C;D3;z2:2](=[S;D1;x0:3])-[O;D2:4] |
N-C(=S)-O-R, the Newman-Kwart substrate |
thiocyanate |
functional:221 |
[N;D1;z3:1]#[C;D2;z3:2]-[S;D2:3] |
R-S-C#N, which is not the isothiocyanate S=C=N-R |
thioester |
functional:131 |
[O;z2;x0:1]=[C;D3;x2;z2:2]-[S;D2;z1;x0] |
R-CO-S-R', the Liebeskind-Srogl electrophile |
thioether |
functional:36 |
[S;D2;z1;x0:1]([C:2])[C:3] |
R-S-R' |
thiol |
functional:35 |
[S;x0;D1;z1:1][C;z1:2] |
R-SH |
thiolate |
functional:234 |
[S;D1;z1;x0;-:1]-[C:2] |
RS- |
thione |
functional:218 |
[S;D1;z2;x0:1]=[C;D3;z2;x1:2] |
C=S with one heteroatom on the carbon, the thioketone |
thiophene_s |
functional:203 |
[S;a;D2:1] |
The aromatic divalent sulfur of a thiophene, thiazole or isothiazole |
thiourea |
functional:154 |
[N;z1:1]-[C;D3;z2;x3:2](=[S;D1:3])-[N;z1:4] |
R2N-CS-NR2 |
tosyl_isocyanide |
functional:165 |
[C;-;D1:1]#[N;+;D2:2]-[C;D2,D3;z1;x2:3]-[S;D4;x2](=[O])=[O] |
TosMIC, the Van Leusen oxazole reagent |
triarylmethyl_radical |
functional:253 |
[C;D3;h0;z1:1](-[C;a:2])(-[C;a:3])-[C;a:4] |^1:0| |
Ar3C•, Gomberg's radical and the trityl spin labels. _radical is in the name because protective.tsv's trityl rows are this skeleton without one |
trifluoromethoxy |
functional:207 |
[F:1][C;D4;z1;x4:2]([F:3])([F:4])-[O;D2:5] |
OCF3. x4 on the carbon: three fluorines and the oxygen all count |
trifluoromethyl |
functional:172 |
[C;D4;z1;x3:1](-[F:2])(-[F:3])-[F:4] |
-CF3 |
trihalomethyl |
functional:226 |
[Cl,Br,I;D1:1]-[C;D4;z1:2](-[Cl,Br,I;D1:3])-[Cl,Br,I;D1:4] |
CX3 for X other than fluorine |
urea |
functional:153 |
[N;z1:1]-[C;D3;z2;x3:2](=[O:3])-[N;z1:4] |
R2N-CO-NR2 |
vicinal_diol |
functional:19 |
[O;D1;z1;x0:1]-[C;z1;x1:2]-[C;z1;x1:3]-[O;D1;z1;x0:4] |
1,2-diol, the dihydroxylation product |
vinyl_sulfone |
functional:175 |
[S;D4:1](=[O:2])(=[O:3])(-[O,N,C:4])-[C;z2:5]=[C:6] |
vinyl sulfone, sulfonamide or sulfonate -- a covalent warhead. chython 2 wrote the third substituent [O,N] and so missed every true sulfone; widened here, which is why the x3 it carried had to go |
weinreb_amide |
functional:127 |
[O:1]=[C;D3;x2:2]-[N;D3;x1](-[C;z1])-[O;D2;x1] |
N-methoxy-N-methyl amide; the extra C on N excludes an N-acyloxy imide |
xanthate |
functional:220 |
[S;D1,D2:1]-[C;D3;z2:2](=[S;D1;x0:3])-[O;D2:4] |
S-C(=S)-O-R, the RAFT agent. D1,D2 because the second sulfur is a free thiol as often as it is substituted |
103 protecting groups, alphabetically. Protects names the functional group the row reveals, which is a row of the table above. :meth:`chython.MoleculeContainer.protective_groups` reports a match and :meth:`chython.MoleculeContainer.deprotect` applies the patch.
Two rows can match one substructure -- a Boc is also a tert-butyl -- and the larger pattern is served first, so a name here is the most specific group that fits, not every group that could.
| Name | Id | Protects | SMARTS | What it removes |
|---|---|---|---|---|
amine_acyl |
protective:84 |
amine |
[N;D2,D3:1]-;!@[C;z2;x2](=O)-[C;D1] |
acetyl, revealing an amine |
amine_alloc |
protective:56 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2;z1;x1][C;D2;x0;z2]=[C;D1] |
allyloxycarbonyl, revealing an amine |
amine_benzhydrylidene |
protective:85 |
amine |
[N;D2:1]=;!@[C;D3;z2;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:2 |
benzhydrylidene (benzophenone imine), revealing an amine |
amine_benzoate |
protective:87 |
amine |
[N;D2,D3:1]-;!@[C;z2;x2](=O)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzoyl, revealing an amine |
amine_benzyl |
protective:75 |
amine |
[N;D2,D3:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzyl, revealing an amine |
amine_bhoc |
protective:79 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D3;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzhydryloxycarbonyl, revealing an amine |
amine_boc |
protective:65 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)-[O;D2;x0]-[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butoxycarbonyl, revealing an amine |
amine_cbz |
protective:60 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)-[O;D2;x0][C;D2;x1;z1][C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzyloxycarbonyl (Cbz/Z), revealing an amine |
amine_chloro_cbz |
protective:61 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)-[O;D2;x0][C;D2;x1;z1][C;a;r6]:1:[C;D3;x1]([Cl;D1]):[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
4-chlorobenzyloxycarbonyl, revealing an amine |
amine_chloro_tritil |
protective:81 |
amine |
[N;D2,D3:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D3;x1]([Cl;D1]):[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
2-chlorotrityl, revealing an amine |
amine_dde_enamine |
protective:70 |
amine |
[N;D2,D3:1]-;!@[C;z2;x1;D3]([C;D1])=[C;D3;r6;x0;z2]1[C;x1;z2;D3](=O)[C;D2][C;D4;x0;z1]([C;D1])([C;D1])[C;D2][C;D3;x1;z2]1=O |
Dde, as the enamine tautomer, revealing an amine |
amine_dde_imine |
protective:71 |
amine |
[N;D2:1]=;!@[C;x1;D3]([C;D1])-[C;D3;r6;x0;z1]1[C;x1;z2;D3](=O)[C;D2][C;D4;x0;z1]([C;D1])([C;D1])[C;D2][C;D3;x1;z2]1=O |
Dde, as the imine tautomer, revealing an amine |
amine_dimethoxybenzyl |
protective:77 |
amine |
[N;D2,D3:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1 |
2,4-dimethoxybenzyl (DMB), revealing an amine |
amine_ethylcarbamate |
protective:55 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0][C;D2;x1;z1][C;D1] |
ethyl carbamate, revealing an amine |
amine_fmoc |
protective:67 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2;x1;z1][C;D3;z1;x0;r5]1[C;a;r6]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D3]:2-[C;a;r6]:3:[C;D2]:[C;D2]:[C;D2]:[C;D2]:C1:3 |
9-fluorenylmethyloxycarbonyl, revealing an amine |
amine_ivdde_enamine |
protective:72 |
amine |
[N;D2,D3:1]-;!@[C;z2;x1;D3]([C;D2;x0;z1][C;D3;x0;z1]([C;D1])[C;D1])=[C;D3;r6;x0;z2]1[C;x1;z2;D3](=O)[C;D2][C;D4;x0;z1]([C;D1])([C;D1])[C;D2][C;D3;x1;z2]1=O |
ivDde, as the enamine tautomer, revealing an amine |
amine_ivdde_imine |
protective:73 |
amine |
[N;D2:1]=;!@[C;x1;D3]([C;D2;x0;z1][C;D3;x0;z1]([C;D1])[C;D1])-[C;D3;r6;x0;z1]1[C;x1;z2;D3](=O)[C;D2][C;D4;x0;z1]([C;D1])([C;D1])[C;D2][C;D3;x1;z2]1=O |
ivDde, as the imine tautomer, revealing an amine |
amine_methoxy_benzyl |
protective:76 |
amine |
[N;D2,D3:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1 |
4-methoxybenzyl (PMB), revealing an amine |
amine_methylcarbamate |
protective:54 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0][C;D1] |
methyl carbamate, revealing an amine |
amine_mtr |
protective:69 |
amine |
[N;D2,D3:1]-;!@[S;D4;x3](=O)(=O)-[C;a;r6]:1:[C;D3;x0]([C;D1]):[C;D3;x0]([C;D1]):[C;D3;x1](-;!@[O;D2;x0][C;D1]):[C;D2]:[C;D3;x0]([C;D1]):1 |
4-methoxy-2,3,6-trimethylbenzenesulfonyl, revealing an amine |
amine_mtt |
protective:78 |
amine |
[N;D2,D3:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x0]([C;D1]):[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
4-methyltrityl (Mtt), revealing an amine |
amine_nosyl |
protective:64 |
amine |
[N;D2,D3:1]-;!@[S;D4;x3](=O)(=O)-[C;a;r6]:1:[C;D3;x1]([N+](=O)[O-]):[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
nitrobenzenesulfonyl (Ns), revealing an amine |
amine_pbf |
protective:68 |
amine |
[N;D2,D3:1]-;!@[S;D4;x3](=O)(=O)-[C;a;r6]:1:[C;D3;x0]([C;D1]):[C;D3;x0]([C;D1]):[C;D3;x1]:2-[O;D2;x0;r5][C;D4;x1]([C;D1])([C;D1])[C;D2;x0;z1][C;D3]:2:[C;D3;x0]([C;D1]):1 |
2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl, revealing an amine |
amine_phenylsulfonyl |
protective:62 |
amine |
[N;D2,D3:1]-;!@[S;D4;x3](=O)(=O)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzenesulfonyl, revealing an amine |
amine_phth |
protective:74 |
amine |
[N;D3:1]1[C;z2;x2;D3](=O)[C;a;r6]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D3]:2[C;z2;x2;D3]1=O |
phthalimide, revealing an amine |
amine_sem |
protective:58 |
amine |
[N;D2,D3:1]-;!@[C;D2;x2;z1][O;D2;x0]-[C;D2;z1;x1][C;D2;x1;z1][Si;D4;z1;x0]([C;D1])([C;D1])[C;D1] |
2-(trimethylsilyl)ethoxymethyl, revealing an amine |
amine_sulfinyl |
protective:83 |
amine |
[N;D2,D3:1]-;!@[S;D3;x2;z2](=O)[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butanesulfinyl, revealing an amine |
amine_tbu |
protective:86 |
amine |
[N;D2,D3:1]-;!@[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butyl, revealing an amine |
amine_teoc |
protective:57 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2;z1;x1][C;D2;x1;z1][Si;D4;z1;x0]([C;D1])([C;D1])[C;D1] |
2-(trimethylsilyl)ethoxycarbonyl, revealing an amine |
amine_tfa |
protective:66 |
amine |
[N;D2,D3:1]-;!@[C;z2;x2](=O)-[C;D4;z1;x3](F)(F)F |
trifluoroacetyl, revealing an amine |
amine_thp |
protective:82 |
amine |
[N;D2,D3:1]-;!@[C;D3;x2;z1;r6]1[O;D2][C;D2][C;D2][C;D2][C;D2]1 |
tetrahydropyranyl, revealing an amine |
amine_tosyl |
protective:63 |
amine |
[N;D2,D3:1]-;!@[S;D4;x3](=O)(=O)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x0]([C;D1]):[C;D2]:[C;D2]:1 |
4-toluenesulfonyl (Ts), revealing an amine |
amine_tritil |
protective:80 |
amine |
[N;D2,D3:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
triphenylmethyl (trityl), revealing an amine |
amine_troc |
protective:59 |
amine |
[N;D2,D3:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2][C;D4;x3]([Cl;D1])([Cl;D1])[Cl;D1] |
2,2,2-trichloroethoxycarbonyl, revealing an amine |
carbonyl_dimethoxy |
protective:52 |
carbonyl |
[C;D3,D4;z1;x2:1](-;!@[O;D2;x0][C;D1])-;!@[O;D2;x0][C;D1] |
dimethyl acetal, revealing a ketone or aldehyde |
carbonyl_dimethylsulfide |
protective:49 |
carbonyl |
[C;D3,D4;z1;x2:1](-;!@[S;D2][C;D1])-;!@[S;D2][C;D1] |
bis(methylthio) acetal, revealing a ketone or aldehyde |
carbonyl_dioxane |
protective:51 |
carbonyl |
[C;D3,D4;z1;x2;r6:1]1[O;D2;x0][C;D2;x1;z1][C;D2;x0;z1][C;D2;x1;z1][O;D2;x0]1 |
1,3-dioxane, revealing a ketone or aldehyde |
carbonyl_dioxolane |
protective:50 |
carbonyl |
[C;D3,D4;z1;x2;r5:1]1[O;D2;x0][C;D2;x1;z1][C;D2;x1;z1][O;D2;x0]1 |
1,3-dioxolane, revealing a ketone or aldehyde |
carbonyl_dithiane |
protective:48 |
carbonyl |
[C;D3,D4;z1;x2;r6:1]1[S;D2;x0;z1][C;D2;x1;z1][C;D2;x0;z1][C;D2;x1;z1][S;D2;x0;z1]1 |
1,3-dithiane, revealing a ketone or aldehyde |
carbonyl_dithiolane |
protective:47 |
carbonyl |
[C;D3,D4;z1;x2;r5:1]1[S;D2;x0;z1][C;D2;x1;z1][C;D2;x1;z1][S;D2;x0;z1]1 |
1,3-dithiolane, revealing a ketone or aldehyde |
carboxyl_trioxabicyclooctane |
protective:53 |
carboxyl |
[C;D4;x3;r6:1]12-;@[O;D2][C;D2;x1;z1][C;D4;x0;z1]([C;D1])([C;D2;x1;z1][O;D2]1)[C;D2;x1;z1][O;D2]2 |
OBO ester (2,6,7-trioxabicyclo[2.2.2]octane), revealing a carboxylic acid |
diol_12_acetone |
protective:34 |
diol |
[O;D2;x0;r5:1]1-;@[C;D4;x2;z1]([C;D1])([C;D1])-[O;D2;x0:2][C:3]-[C:4]1 |
acetonide (isopropylidene acetal), revealing a 1,2-diol |
diol_12_benzylidene |
protective:45 |
diol |
[O;D2;x0;r5:1]1-;@[C;D3;x2;z1]([C;a;r6]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:2)-[O;D2;x0:2][C:3]-[C:4]1 |
benzylidene acetal, revealing a 1,2-diol |
diol_12_cyclohexanone |
protective:41 |
diol |
[O;D2;x0;r5:1]1-;@[C;D4;x2;z1]2([C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1]2)-[O;D2;x0:2][C:3]-[C:4]1 |
cyclohexylidene acetal, revealing a 1,2-diol |
diol_12_cyclopentanone |
protective:39 |
diol |
[O;D2;x0;r5:1]1-;@[C;D4;x2;z1]2([C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1]2)-[O;D2;x0:2][C:3]-[C:4]1 |
cyclopentylidene acetal, revealing a 1,2-diol |
diol_12_diacetal |
protective:43 |
diol |
[O;D2;x0;r6:1]1-;@[C;D4;x2;z1]([O;D2;x0][C;D1])([C;D1])[C;D4;x2;z1]([O;D2;x0][C;D1])([C;D1])-[O;D2;x0:2][C:3]-[C:4]1 |
butane-2,3-diacetal (BDA), revealing a 1,2-diol |
diol_12_formalin |
protective:37 |
diol |
[O;D2;x0;r5:1]1-;@[C;D2;x2;z1]-[O;D2;x0:2][C:3]-[C:4]1 |
methylene acetal, revealing a 1,2-diol |
diol_13_acetone |
protective:35 |
diol |
[O;D2;x0;r6:1]1-;@[C;D4;x2;z1]([C;D1])([C;D1])-[O;D2;x0:2][C:3][C:4]-[C:5]1 |
acetonide (isopropylidene acetal), revealing a 1,3-diol |
diol_13_benzylidene |
protective:46 |
diol |
[O;D2;x0;r6:1]1-;@[C;D3;x2;z1]([C;a;r6]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:2)-[O;D2;x0:2][C:3][C:4]-[C:5]1 |
benzylidene acetal, revealing a 1,3-diol |
diol_13_cyclohexanone |
protective:42 |
diol |
[O;D2;x0;r6:1]1-;@[C;D4;x2;z1]2([C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1]2)-[O;D2;x0:2][C:3][C:4]-[C:5]1 |
cyclohexylidene acetal, revealing a 1,3-diol |
diol_13_cyclopentanone |
protective:40 |
diol |
[O;D2;x0;r6:1]1-;@[C;D4;x2;z1]2([C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1][C;D2;x0;z1]2)-[O;D2;x0:2][C:3][C:4]-[C:5]1 |
cyclopentylidene acetal, revealing a 1,3-diol |
diol_13_diacetal |
protective:44 |
diol |
[O;D2;x0;r7:1]1-;@[C;D4;x2;z1]([O;D2;x0][C;D1])([C;D1])[C;D4;x2;z1]([O;D2;x0][C;D1])([C;D1])-[O;D2;x0:2][C:3][C:4]-[C:5]1 |
butane-2,3-diacetal (BDA), revealing a 1,3-diol |
diol_13_formalin |
protective:38 |
diol |
[O;D2;x0;r6:1]1-;@[C;D2;x2;z1]-[O;D2;x0:2][C:3][C:4]-[C:5]1 |
methylene acetal, revealing a 1,3-diol |
hydroxyl_acyl |
protective:101 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x2](=O)-[C;D1] |
acetyl, revealing an alcohol |
hydroxyl_alloc |
protective:5 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2;z1;x1][C;D2;x0;z2]=[C;D1] |
allyloxycarbonyl, revealing an alcohol |
hydroxyl_allyl |
protective:99 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1][C;D2;x0;z2]=[C;D1] |
allyl, revealing an alcohol |
hydroxyl_amine_acetone |
protective:36 |
hydroxyl, amine |
[O;D2;x0;r5:1]1-;@[C;D4;x2;z1]([C;D1])([C;D1])-[N;z1:2][C:3]-[C:4]1 |
acetonide across the amino alcohol, revealing an amino alcohol |
hydroxyl_benzoate |
protective:18 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x2](=O)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzoyl, revealing an alcohol |
hydroxyl_benzyl |
protective:100 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzyl, revealing an alcohol |
hydroxyl_boc |
protective:97 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butoxycarbonyl, revealing an alcohol |
hydroxyl_bom |
protective:15 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x2;z1][O;D2;x0][C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzyloxymethyl, revealing an alcohol |
hydroxyl_chloro_tritil |
protective:28 |
hydroxyl |
[O;D2:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D3;x1]([Cl;D1]):[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
2-chlorotrityl, revealing an alcohol |
hydroxyl_dimethoxybenzyl |
protective:13 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1 |
2,4-dimethoxybenzyl (DMB), revealing an alcohol |
hydroxyl_dimetoxy_tritil |
protective:27 |
hydroxyl |
[O;D2:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
4,4′-dimethoxytrityl (DMT), revealing an alcohol |
hydroxyl_dmab_enamine |
protective:32 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x1;z1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1](:[C;D2]:[C;D2]:1)-[N;D2;x0;z1]-[C;z2;x1;D3]([C;D2;x0;z1][C;D3;x0;z1]([C;D1])[C;D1])=[C;D3;r6;x0;z2]1[C;x1;z2;D3](=O)[C;D2][C;D4;x0;z1]([C;D1])([C;D1])[C;D2][C;D3;x1;z2]1=O |
Dmab, as the enamine tautomer, revealing an alcohol |
hydroxyl_dmab_imine |
protective:33 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x1;z1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1](:[C;D2]:[C;D2]:1)-[N;D2;x0;z2]=[C;x1;D3]([C;D2;x0;z1][C;D3;x0;z1]([C;D1])[C;D1])-[C;D3;r6;x0;z1]1[C;x1;z2;D3](=O)[C;D2][C;D4;x0;z1]([C;D1])([C;D1])[C;D2][C;D3;x1;z2]1=O |
Dmab, as the imine tautomer, revealing an alcohol |
hydroxyl_ee |
protective:23 |
hydroxyl |
[O;D2:1]-;!@[C;D3;x2;z1]([O;D2;x0][C;D2;x1;z1][C;D1])[C;D1] |
1-ethoxyethyl, revealing an alcohol |
hydroxyl_ethyl |
protective:103 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1]-[C;D1] |
ethyl, revealing an alcohol |
hydroxyl_fmoc |
protective:2 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2;x1;z1][C;D3;z1;x0;r5]1[C;a;r6]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D3]:2-[C;a;r6]:3:[C;D2]:[C;D2]:[C;D2]:[C;D2]:C1:3 |
9-fluorenylmethyloxycarbonyl, revealing an alcohol |
hydroxyl_mem |
protective:21 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x2;z1][O;D2;x0][C;D2;z1;x1][C;D2;z1;x1][O;D2;x0][C;D1] |
2-methoxyethoxymethyl, revealing an alcohol |
hydroxyl_methoxy_benzoate |
protective:17 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x2](=O)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1 |
4-methoxybenzoyl (anisoyl), revealing an alcohol |
hydroxyl_methoxy_benzyl |
protective:12 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1 |
4-methoxybenzyl (PMB), revealing an alcohol |
hydroxyl_methyl |
protective:102 |
hydroxyl |
[O;D2:1]-;!@[C;D1] |
methyl, revealing an alcohol |
hydroxyl_mmt |
protective:29 |
hydroxyl |
[O;D2:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
4-methoxytrityl (MMT), revealing an alcohol |
hydroxyl_mom |
protective:20 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x2;z1][O;D2;x0][C;D1] |
methoxymethyl, revealing an alcohol |
hydroxyl_mop |
protective:24 |
hydroxyl |
[O;D2:1]-;!@[C;D4;x2;z1]([O;D2;x0][C;D1])([C;D1])[C;D1] |
2-methoxyprop-2-yl, revealing an alcohol |
hydroxyl_mpe |
protective:30 |
hydroxyl |
[O;D2:1]-;!@[C;D4;x1;z1]([C;D1])([C;D2;x0;z1][C;D1])[C;D2;x0;z1][C;D1] |
4-methoxyphenylethyl, revealing an alcohol |
hydroxyl_naphthyl |
protective:14 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D3]:2:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D3]:2:[C;D2]:[C;D2]:1 |
2-naphthylmethyl, revealing an alcohol |
hydroxyl_o_nitrobenzyl |
protective:11 |
hydroxyl |
[O;D2:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D3;x1]([N+](=O)[O-]):[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
ortho-nitrobenzyl, revealing an alcohol |
hydroxyl_piv |
protective:16 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x2](=O)-[C;D4;x0;z1]([C;D1])([C;D1])[C;D1] |
pivaloyl, revealing an alcohol |
hydroxyl_sem |
protective:25 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x2;z1][O;D2;x0][C;D2;z1;x1][C;D2;z1;x1][Si;D4;z1;x0]([C;D1])([C;D1])[C;D1] |
2-(trimethylsilyl)ethoxymethyl, revealing an alcohol |
hydroxyl_tbdps |
protective:10 |
hydroxyl |
[O;D2:1]-;!@[Si;D4;z1;x1]([C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)([C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butyldiphenylsilyl, revealing an alcohol |
hydroxyl_tbs |
protective:8 |
hydroxyl |
[O;D2:1]-;!@[Si;D4;z1;x1]([C;D1])([C;D1])[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butyldimethylsilyl, revealing an alcohol |
hydroxyl_tbu |
protective:98 |
hydroxyl |
[O;D2:1]-;!@[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butyl, revealing an alcohol |
hydroxyl_teoc |
protective:4 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2;z1;x1][C;D2;x1;z1][Si;D4;z1;x0]([C;D1])([C;D1])[C;D1] |
2-(trimethylsilyl)ethoxycarbonyl, revealing an alcohol |
hydroxyl_tes |
protective:7 |
hydroxyl |
[O;D2:1]-;!@[Si;D4;z1;x1]([C;D2;x1;z1][C;D1])([C;D2;x1;z1][C;D1])[C;D2;x1;z1][C;D1] |
triethylsilyl, revealing an alcohol |
hydroxyl_tfa |
protective:19 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x2](=O)-[C;D4;z1;x3](F)(F)F |
trifluoroacetyl, revealing an alcohol |
hydroxyl_thiocarbamate |
protective:1 |
hydroxyl |
[O;D2:1]-;!@[C;x3;z2](=[S;D1])[N;D3;x0]([C;D1])[C;D1] |
N,N-dimethylthiocarbamate, revealing an alcohol |
hydroxyl_thp |
protective:22 |
hydroxyl |
[O;D2:1]-;!@[C;D3;x2;z1;r6]1[O;D2][C;D2][C;D2][C;D2][C;D2]1 |
tetrahydropyranyl, revealing an alcohol |
hydroxyl_tips |
protective:9 |
hydroxyl |
[O;D2:1]-;!@[Si;D4;z1;x1]([C;D3;z1;x1]([C;D1])[C;D1])([C;D3;z1;x1]([C;D1])[C;D1])[C;D3;z1;x1]([C;D1])[C;D1] |
triisopropylsilyl, revealing an alcohol |
hydroxyl_tms |
protective:6 |
hydroxyl |
[O;D2:1]-;!@[Si;D4;z1;x1]([C;D1])([C;D1])[C;D1] |
trimethylsilyl, revealing an alcohol |
hydroxyl_trifluoroethyl |
protective:31 |
hydroxyl |
[O;D2:1]-;!@[C;D2;x1;z1][C;D4;x3;z1](F)(F)F |
2,2,2-trifluoroethyl, revealing an alcohol |
hydroxyl_tritil |
protective:26 |
hydroxyl |
[O;D2:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
triphenylmethyl (trityl), revealing an alcohol |
hydroxyl_troc |
protective:3 |
hydroxyl |
[O;D2:1]-;!@[C;z2;x3](=O)[O;D2;x0]-[C;D2][C;D4;x3]([Cl;D1])([Cl;D1])[Cl;D1] |
2,2,2-trichloroethoxycarbonyl, revealing an alcohol |
thiol_amine_dimethoxybenzyl |
protective:96 |
thiol, amine |
[S;D2;r5;x0;z1:1]1[C:3][C:4][N;z1:2]-[C;D3;x2;z1]1-[C;a;r6]:1:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1 |
2,4-dimethoxybenzylidene across the aminothiol, revealing an aminothiol |
thiol_benzyl |
protective:92 |
thiol |
[S;D2;x0;z1:1]-;!@[C;D2;z1;x1]-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
benzyl, revealing a thiol |
thiol_chloro_tritil |
protective:91 |
thiol |
[S;D2;x0;z1:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D3;x1]([Cl;D1]):[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
2-chlorotrityl, revealing a thiol |
thiol_dimetoxy_tritil |
protective:90 |
thiol |
[S;D2;x0;z1:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
4,4′-dimethoxytrityl (DMT), revealing a thiol |
thiol_mmt |
protective:89 |
thiol |
[S;D2;x0;z1:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
4-methoxytrityl (MMT), revealing a thiol |
thiol_stbu |
protective:94 |
thiol |
[S;D2;x1;z1:1]-;!@[S;D2;z1;x1]-[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butyl disulfide, revealing a thiol |
thiol_strimethoxyphenyl |
protective:95 |
thiol |
[S;D2;x1;z1:1]-;!@[S;D2;z1;x1]-[C;a;r6]:1:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D3;x1]([O;D2;x0][C;D1]):[C;D2]:[C;D3;x1]:1[O;D2;x0][C;D1] |
2,4,6-trimethoxyphenyl disulfide, revealing a thiol |
thiol_tbu |
protective:93 |
thiol |
[S;D2;x0;z1:1]-;!@[C;D4;x1;z1]([C;D1])([C;D1])[C;D1] |
tert-butyl, revealing a thiol |
thiol_tritil |
protective:88 |
thiol |
[S;D2;x0;z1:1]-;!@[C;D4;z1;x1](-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)(-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1)-[C;a;r6]:1:[C;D2]:[C;D2]:[C;D2]:[C;D2]:[C;D2]:1 |
triphenylmethyl (trityl), revealing a thiol |