dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32b442668f9d4fb18085508f5ff084c7 | C1C2CC3CC1CC(C2)C3.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C1C2CC3CC(C2)CC1C3.OC12CC3CC(C1)CC(O)(C3)C2.OC12CC3CC(CC(C3)C1)C2 | C12CC3CC(CC(C1)C3)C2.ON1C(N(C(N(C1=O)O)=O)O)=O.O=O>>C12C(C3CC(CC(C1)C3)C2)=O.C12(CC3CC(CC(C1)C3)C2)O.C12(CC3(CC(CC(C1)C3)C2)O)O | [CH2:2]1[CH:3]2[CH2:4][CH:5]3[CH2:11][CH:10]1[CH2:9][CH:29]([CH2:8]2)[CH2:30]3.[O:1]=[O:24].O=[c:6]1n(O)[c:28](=O)n([OH:21])[c:33](=O)n1[OH:12]>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8]2)[CH2:9][CH:10]1[CH2:11]3.[OH:12][C:13]12[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18]1)[CH2:19][C:20]([OH:21])([CH2:22]3)[CH... | C1C2CC3CC1CC(C2)C3.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C1C2CC3CC(C2)CC1C3.OC12CC3CC(C1)CC(O)(C3)C2.OC12CC3CC(CC(C3)C1)C2 | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 3c62ed814a71c593216dbbdb15adad5cf20952451beacce53b5262a4abca1be8 | b9de26c3f25bb3330073f673351172b347bedbff86fcdc39ea3909eb58ebd67f | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3.O=C1C2CC3CC(C2)CC1C3 | O-n1:[c;H0;D3;+0:1](=O):n(-[OH;D1;+0:2]):[c;H0;D3;+0:3](=O):n(-[OH;D1;+0:4]):[c;H0;D3;+0:5]:1=O.[C:6]1-[C:7]2-[CH2;D2;+0:8]-[C:9]3-[C:10]-[CH;D3;+0:11]-1-[CH2;D2;+0:12]-[CH;D3;+0:13](-[CH2;D2;+0:14]-3)-[CH2;D2;+0:15]-2.[O;H0;D1;+0:16]=[O;H0;D1;+0:17]>>[C:18]-[C:19](-[OH;D1;+0:4])(-[C:20])-[C:21]-[C:22](-[OH;D1;+0:2])(-... | null | [] | null | null | null | null | A mixture of 1.00 g of adamantane, 0.026 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (2% by mole relative to adamantane), 9.0 g of acetic acid and 0.003 g of acetylacetonatovanadium(III) was stirred at 85° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 6 hours. The resulting product in the react... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Tertiary alcohol.Tertiary alcohol.Tertiary alcohol | c1ncncn1.C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | null | C(C)(=O)O | null | null | C1C2CC3CC1CC(C2)C3.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)O>O=C1C2CC3CC(C2)CC1C3.OC12CC3CC(C1)CC(O)(C3)C2.OC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-580c97f4c2db48c5b59e2f445311d966 | CC(=O)On1c(=O)n(OC(C)=O)c(=O)n(OC(C)=O)c1=O.O=O>>O=C1C=CC=C2C1=Cc1ccccc12 | O=O.C1=CC=CC=2C3=CC=CC=C3CC12.C(C)(=O)ON1C(N(C(N(C1=O)OC(C)=O)=O)OC(C)=O)=O>>C1(C=CC=C2C3=CC=CC=C3C=C12)=O.C1=CC=CC=2C3=CC=CC=C3CC12 | O=[C:2](On1[c:3](=O)n(O[C:14](=O)[CH3:13])[c:7](=O)n(O[C:11](=O)[CH3:12])[c:6]1=O)[CH3:10].O=[O:1]>>[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]1=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]12 | CC(=O)On1c(=O)n(OC(C)=O)c(=O)n(OC(C)=O)c1=O.O=O | O=C1C=CC=C2C1=Cc1ccccc12 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7cf1898f9da36ac046bc097fa30ad73b76e02a63efd200157b044c4619fc387a | cbcd9fbdedbc03e53fd6c979c34e64e805ba456509030c5a2394f2c260e9bbd5 | O=C1C=CC=C2C1=Cc1ccccc12 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-O-n1:[c;H0;D3;+0:3](=O):n(-O-[C;H0;D3;+0:4](=O)-[CH3;D1;+0:5]):[c;H0;D3;+0:6](=O):n(-O-[C;H0;D3;+0:7](=O)-[CH3;D1;+0:8]):[c;H0;D3;+0:9]:1=O.O=[O;H0;D1;+0:10]>>[O;H0;D1;+0:10]=[C;H0;D3;+0:4]1-[CH;D2;+0:6]=[C:11]-[C:12]=[C;H0;D3;+0:3]2-[C;H0;D3;+0:9]-1=[C:13]-[c:14]1:[cH;D2;+0:5]:[cH;D2;+... | null | [] | null | null | null | null | A mixture of 1.00 g of fluorene, 0.055 g of 1,3,5-triacetoxy-hexahydro-1,3,5-triazine-2,4,6-trione (3% by mole relative to fluorene), 9.0 g of acetic acid, 0.008 g of cobalt(II) acetate.4H2O and 0.007 g of manganese(II) acetate.4H2O was stirred at 120° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 6 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Conjugated diene | c1ncncn1 | C1=CCC2=Cc3ccccc3C2=C1 | C1=CCC2=Cc3ccccc3C2=C1 | HO- | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | CC(=O)On1c(=O)n(OC(C)=O)c(=O)n(OC(C)=O)c1=O.O=O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>O=C1C=CC=C2C1=Cc1ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c02a50b789943babd720d0d605edb00 | C1CCCCC1.CC(=O)O.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)CCCC(=O)O.O=C(O)CCCCC(=O)O.O=C1CCCCC1 | C1CCCCC1.ON1C(N(C(N(C1=O)O)=O)O)=O.C(C)(=O)O.O=O>>C1(CCCCC1)=O.C(CCCCC(=O)O)(=O)O.C(CCCC(=O)O)(=O)O | [CH2:4]1[CH2:5][CH2:6][CH2:23][CH2:24][CH2:25]1.[CH3:16][C:17](=[O:18])[OH:19].[O:9]=[O:10].O=[c:26]1n([OH:12])[c:2](=[O:1])n([OH:20])[c:7](=[O:8])n1[OH:3]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[OH:9].[O:10]=[C:11]([OH:12])[CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[OH:19].[O:20]=[C:21]1[CH2:22][CH2... | C1CCCCC1.CC(=O)O.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)CCCC(=O)O.O=C(O)CCCCC(=O)O.O=C1CCCCC1 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | C-C Coupling | OtherReaction | 64ef3769166611b2d4305e4aa9c6e56cec579ef661ab3bbe882e8528624dfca6 | 6f3195863a8b984d748f35873e471277ccb059d28debc50bc5d9c50d34c46c6f | O=C1CCCCC1 | O=[c;H0;D3;+0:1]1:n(-[OH;D1;+0:2]):[c;H0;D3;+0:3](=[O;D1;H0:4]):n(-[OH;D1;+0:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):n:1-[OH;D1;+0:8].[CH3;D1;+0:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12].[C:13]1-[CH2;D2;+0:14]-[CH2;D2;+0:15]-[C:16]-[CH2;D2;+0:17]-[CH2;D2;+0:18]-1.[O;H0;D1;+0:19]=[O;H0;D1;+0:20]>>[O;D1;H0:4]=[C;H0;D3;+0:3](-[OH;D1... | null | [] | null | null | null | null | A mixture of 1.00 g of cyclohexane, 0.063 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to cyclohexane), 29.0 g of acetic acid, 0.015 g of cobalt(II) acetate.4H2O and 0.015 g of manganese(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 8 hou... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Ketone | C1CCCCC1.c1ncncn1 | C1CCCCC1 | C1CCCCC1 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | null | C1CCCCC1.CC(=O)O.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-]>O=C(O)CCCC(=O)O.O=C(O)CCCCC(=O)O.O=C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ceb42c45e9a4b67a98dfccbbdb747c4 | CC(C)(C#N)N=NC(C)(C)C#N.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>CC(=O)Oc1ccc(C(=O)O)cc1 | CC=1C=CC(=CC1)OC(=O)C.ON1C(N(C(N(C1=O)O)=O)O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C.O=O>>C(C)(=O)OC1=CC=C(C(=O)O)C=C1.CC=1C=CC(=CC1)OC(=O)C | N#[C:9][C:5](N=N[C:2]([CH3:1])([CH3:7])[C:12]#N)([CH3:6])[CH3:13].[O:10]=[O:11].O=c1n(O)c(=[O:3])n([OH:4])[c:8](=O)n1O>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13]1 | CC(C)(C#N)N=NC(C)(C)C#N.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | CC(=O)Oc1ccc(C(=O)O)cc1 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Acylation | OtherReaction | 31c9678aeaf20d90463f4f99a520f1bfc741d2a41f144a5e02f5f816cbc68af1 | 7c5517e31da130486597b9b819317027e9cf850b703953777e392775c0eccf83 | c1ccccc1 | N#[C;H0;D2;+0:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-N=N-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[C;H0;D2;+0:8]#N.O-n1:[c;H0;D3;+0:9](=O):n(-[OH;D1;+0:10]):c(=[O;H0;D1;+0:11]):n(-O):c:1=O.[O;H0;D1;+0:12]=[O;H0;D1;+0:13]>>[C;D1;H3:3]-[C;H0;D3;+0:2](=[O;H0;D1;+0:11])-[O;H0;D2;+0:10]-[c;H0;D3;+0:5]1:[cH;D2... | null | [] | null | null | null | null | A mixture of 0.300 g of p-tolyl acetate, 0.018 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to p-tolyl acetate), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4H2O, 0.001 g of manganese(II) acetate.4H2O and 0.003 g of 2,2′-azobisisobutyronitrile was stirred at 100° C. in an atmos... | 10.6084/m9.figshare.5104873.v1 | null | Diazene.Nitrile.Nitrile | Carboxylic acid.Ester | c1ncncn1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | CC(C)(C#N)N=NC(C)(C)C#N.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>CC(=O)Oc1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26efa417911843ab8037566abfc3abeb | CC(C)(C#N)N=NC(C)(C)C#N.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>CC(=O)Oc1cccc(C(=O)O)c1 | C(C)(=O)OC=1C=C(C=CC1)C.ON1C(N(C(N(C1=O)O)=O)O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C.O=O>>C(C)(=O)OC=1C=C(C(=O)O)C=CC1.C(C)(=O)OC=1C=C(C=CC1)C | N#[C:9][C:2](N=N[C:5]([CH3:6])([C:10]#N)[CH3:13])([CH3:1])[CH3:8].[O:11]=[O:12].O=c1n(O)c(=[O:3])n([OH:4])[c:7](=O)n1O>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13]1 | CC(C)(C#N)N=NC(C)(C)C#N.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | CC(=O)Oc1cccc(C(=O)O)c1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Acylation | OtherReaction | 31c9678aeaf20d90463f4f99a520f1bfc741d2a41f144a5e02f5f816cbc68af1 | 7c5517e31da130486597b9b819317027e9cf850b703953777e392775c0eccf83 | c1ccccc1 | N#[C;H0;D2;+0:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-N=N-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:7])-[C;H0;D2;+0:8]#N.O-n1:[c;H0;D3;+0:9](=O):n(-[OH;D1;+0:10]):c(=[O;H0;D1;+0:11]):n(-O):c:1=O.[O;H0;D1;+0:12]=[O;H0;D1;+0:13]>>[C;D1;H3:6]-[C;H0;D3;+0:5](=[O;H0;D1;+0:11])-[O;H0;D2;+0:10]-[c;H0;D3;+0:2]1:[cH;D2... | null | [] | null | null | null | null | A mixture of 0.300 g of m-tolyl acetate, 0.018 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to m-tolyl acetate), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4H2O and 0.003 g of 2,2′-azobisisobutyronitrile was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) fo... | 10.6084/m9.figshare.5104873.v1 | null | Diazene.Nitrile.Nitrile | Carboxylic acid.Ester | c1ncncn1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | CC(C)(C#N)N=NC(C)(C)C#N.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>CC(=O)Oc1cccc(C(=O)O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7c80ab99e7d4d96b58b64aefcd0955f | Cc1ccc(C#N)cc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>N#Cc1ccc(C(=O)O)cc1.N#Cc1ccc(C=O)cc1 | O=O.C1(=CC=C(C=C1)C#N)C.ON1C(N(C(N(C1=O)O)=O)O)=O>>C(#N)C1=CC=C(C(=O)O)C=C1.C(#N)C1=CC=C(C=O)C=C1 | [N:1]#[C:2][c:3]1[cH:11][cH:10][c:17]([CH3:18])[cH:20][cH:21]1.[O:9]=[O:19].O=[c:4]1n(O)[c:6](=O)n(O)[c:7](=[O:8])[n:12]1O>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][cH:11]1.[N:12]#[C:13][c:14]1[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1 | Cc1ccc(C#N)cc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | N#Cc1ccc(C(=O)O)cc1.N#Cc1ccc(C=O)cc1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Acylation | OtherReaction | e24c087b15d78b33191aef5b55ae5dabd3dcdce6833956baf85cd3388872f913 | 0d2febef5f2b5f6b55c4b581df97ad30ba0af3c0502070bc493d21383c10159a | c1ccccc1.c1ccccc1 | O-[n;H0;D3;+0:1]1:[c;H0;D3;+0:2](=O):n(-O):[c;H0;D3;+0:3](=O):n(-O):[c;H0;D3;+0:4]:1=[O;D1;H0:5].[CH3;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[C:11]#[N;D1;H0:12]):[c:13]:[cH;D2;+0:14]:1.[O;H0;D1;+0:15]=[O;H0;D1;+0:16]>>[N;D1;H0:12]#[C:11]-[c;H0;D3;+0:10]1:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:3](-[C;H0;... | null | [] | null | null | null | null | A mixture of 0.351 g of p-tolunitrile, 0.005 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (1% by mole relative to p-tolunitrile), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 14 hours. The resulting product in the rea... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde.Carboxylic acid.Nitrile | c1ccccc1.c1ncncn1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | Cc1ccc(C#N)cc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>N#Cc1ccc(C(=O)O)cc1.N#Cc1ccc(C=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-776d31db73da43fa94d12812791c84cc | Cc1ccc(C(C)(C)C)cc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>CC(C)(C)c1ccc(C(=O)O)cc1.CC(C)(C)c1ccc(C=O)cc1 | O=O.C(C)(C)(C)C1=CC=C(C=C1)C.ON1C(N(C(N(C1=O)O)=O)O)=O>>C(C)(C)(C)C1=CC=C(C(=O)O)C=C1.C(C)(C)(C)C1=CC=C(C=O)C=C1 | [C:2]([CH3:3])([c:5]1[cH:6][cH:20][c:21]([CH3:22])[cH:12][cH:13]1)([CH3:15])[CH3:25].O=[O:23].O=[c:1]1n(O)[c:4](=O)n([OH:11])[c:9](=[O:10])n1O>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13]1.[CH3:14][C:15]([CH3:16])([CH3:17])[c:18]1[cH:19][cH:20][c:21]([CH:22]=[O:23])[cH:24]... | Cc1ccc(C(C)(C)C)cc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | CC(C)(C)c1ccc(C(=O)O)cc1.CC(C)(C)c1ccc(C=O)cc1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Acylation | OtherReaction | 9241b14d78dab6c8c9b0f6752018a83a983640ceff8a22f292f518338fa6cb58 | c5d8779ec33354a73f2396d2ebdee3f99173dea3b784b8d3e6545ffeaa6b9034 | c1ccccc1.c1ccccc1 | O-n1:[c;H0;D3;+0:1](=O):n(-O):[c;H0;D3;+0:2](=[O;D1;H0:3]):n(-[OH;D1;+0:4]):[c;H0;D3;+0:5]:1=O.O=[O;H0;D1;+0:6].[C;D1;H3:7]-[C;H0;D4;+0:8](-[CH3;D1;+0:9])(-[CH3;D1;+0:10])-[c:11]1:[c:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[CH3;D1;+0:15]):[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[C;D1;H3:18]-[C;H0;D4;+0:9](-[C;D1;H3:19])(-[C;D1;H3:20... | null | [] | null | null | null | null | A mixture of 0.445 g of 4-t-butyltoluene, 0.016 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to 4-t-butyltoluene), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 2 hours. The resulting product in th... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde.Carboxylic acid | c1ccccc1.c1ncncn1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | Cc1ccc(C(C)(C)C)cc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>CC(C)(C)c1ccc(C(=O)O)cc1.CC(C)(C)c1ccc(C=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6a8ba3d36bf4f319c6bd44ce0526ecd | O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)c1ccc(Cl)cc1 | O=O.ClC1=CC=C(C=C1)C.ON1C(N(C(N(C1=O)O)=O)O)=O>>ClC1=CC=C(C(=O)O)C=C1.ClC1=CC=C(C=C1)C | O=[O:11].O=[c:12]1n(O)[c:10](=[O:9])n(O)[c:15](=O)n1O>>[O:9]=[C:10]([OH:11])[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)c1ccc(Cl)cc1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Acylation | OtherReaction | 5e9aa040a7ca985fc02bb7893da77ec63538ab8ea3671d7344cf2e204446b339 | 9275506b736f852eaa62a7ff92284c86fed5ac739e187aa99c675d2b152c37cb | c1ccccc1 | O-n1:[c;H0;D3;+0:1](=[O;D1;H0:2]):n(-O):[c;H0;D3;+0:3](=O):n(-O):[c;H0;D3;+0:4]:1=O.O=[O;H0;D1;+0:5]>>[Cl;D1;H0:6]-[c;H0;D3;+0:3]1:[c:7]:[c:8]:[c;H0;D3;+0:4](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:5]):[c:9]:[c:10]:1 | null | [] | null | null | null | null | A mixture of 0.380 g of 4-chlorotoluene, 0.027 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to 4-chlorotoluene), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 14 hours. The resulting product in the... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Carboxylic acid | c1ncncn1 | c1ccccc1 | c1ccccc1 | Other | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>O=C(O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25be29cbfe4341219e0e5c16fc46daa6 | Cc1ccccc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)c1ccccc1.O=Cc1ccccc1 | O=O.C1(=CC=CC=C1)C.ON1C(N(C(N(C1=O)O)=O)O)=O>>C(C1=CC=CC=C1)(=O)O.C(C1=CC=CC=C1)=O | [CH3:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:3]=[O:10].O=[c:4]1n(O)[c:2](=[O:1])n(O)[c:5](=O)n1O>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[O:10]=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1ccccc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)c1ccccc1.O=Cc1ccccc1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | C(C)(=O)O | Acylation | OtherReaction | 138bb0ed5396ae64f9d1d9a3aee3844fef9e0ef91c230ecf0e7e30212bdab51e | c5d8779ec33354a73f2396d2ebdee3f99173dea3b784b8d3e6545ffeaa6b9034 | c1ccccc1.c1ccccc1 | O-n1:[c;H0;D3;+0:1](=[O;D1;H0:2]):n(-O):[c;H0;D3;+0:3](=O):n(-O):[c;H0;D3;+0:4]:1=O.[CH3;D1;+0:5]-[c:6](:[c:7]):[c:8].[O;H0;D1;+0:9]=[O;H0;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:10])-[c;H0;D3;+0:4]1:[c:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:3]:1.[O;H0;D1;+0:9]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | A mixture of 0.276 g of toluene, 0.005 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (1% by mole relative to toluene), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4H2O was stirred at 60° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 6 hours. The resulting product in the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde.Carboxylic acid | c1ncncn1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O | null | null | Cc1ccccc1.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)O>O=C(O)c1ccccc1.O=Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98cca51794be4ca59ebc9de69d50807e | CC(=O)O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)c1ccccc1[N+](=O)[O-] | C(C)(=O)O.[N+](=O)([O-])C1=C(C=CC=C1)C.ON1C(N(C(N(C1=O)O)=O)O)=O>>[N+](=O)([O-])C1=C(C(=O)O)C=CC=C1.[N+](=O)([O-])C1=C(C=CC=C1)C | [OH:13][C:17]([CH3:18])=[O:21].O=[c:14]1n(O)[c:12](=[O:11])[n:20]([OH:22])[c:19](=O)n1O>>[O:11]=[C:12]([OH:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22] | CC(=O)O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)c1ccccc1[N+](=O)[O-] | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | O | Acylation | OtherReaction | 18bf4161122b1d61e09a4c61abc6a9a5a05b453f59375f3ec0a08be2855a8995 | 5cd90b2ecbb4b4635401de67e125641485f9e8e61580f3a32e8c675fa9681152 | c1ccccc1 | O-n1:[c;H0;D3;+0:1](=[O;D1;H0:2]):[n;H0;D3;+0:3](-[OH;D1;+0:4]):[c;H0;D3;+0:5](=O):n(-O):[c;H0;D3;+0:6]:1=O.[CH3;D1;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[OH;D1;+0:10]>>[O-;H0;D1:4]-[N+;H0;D3:3](=[O;H0;D1;+0:9])-[c;H0;D3;+0:5]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:11]:[c:12]:[c;H0;D3;+0:6]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1... | null | [] | 150 | CELSIUS | 14 | HOUR | In an autoclave, 0.274 g of 2-nitrotoluene, 0.018 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to 2-nitrotoluene), 5 g of acetic acid, 0.003 g of cobalt (II) acetate.4H2O, 0.001 g of manganese(II) acetate.4H2O and 0.018 g of NO2 were placed. The autoclave was charged with 1 MPa of ai... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Carboxylic acid.Nitro group | c1ncncn1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].O | 150 | 14 | CC(=O)O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].O>O=C(O)c1ccccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7323dbcef384483968c17fe3f4b0f01 | CC(=O)O.Cc1ccc([N+](=O)[O-])cc1.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)c1ccc([N+](=O)[O-])cc1.O=Cc1ccc([N+](=O)[O-])cc1 | C(C)(=O)O.[N+](=O)([O-])C1=CC=C(C=C1)C.ON1C(N(C(N(C1=O)O)=O)O)=O>>[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1.[N+](=O)([O-])C1=CC=C(C=O)C=C1 | [OH:3][C:23](=[O:20])[CH3:22].[cH:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:15]([CH3:14])[cH:16]1.O=[c:5]1n(O)[c:17](=O)n([OH:13])[c:2](=[O:1])[n:19]1[OH:21]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1.[O:13]=[CH:14][c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][... | CC(=O)O.Cc1ccc([N+](=O)[O-])cc1.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)c1ccc([N+](=O)[O-])cc1.O=Cc1ccc([N+](=O)[O-])cc1 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | O | Acylation | OtherReaction | 763d93b8ab8332582f4652337e59f69ee189b987cc36565d1a3866e0123dff27 | d4fcd646dcb3785c2f2a16e4704805189bfeda69cf5613b0a5523bc728a83d3b | c1ccccc1.c1ccccc1 | O-n1:[c;H0;D3;+0:1](=O):n(-[OH;D1;+0:2]):[c;H0;D3;+0:3](=[O;D1;H0:4]):[n;H0;D3;+0:5](-[OH;D1;+0:6]):[c;H0;D3;+0:7]:1=O.[#7;+:8]-[c:9]1:[c:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[CH3;D1;+0:13]):[cH;D2;+0:14]:[cH;D2;+0:15]:1.[CH3;D1;+0:16]-[C;H0;D3;+0:17](=[O;H0;D1;+0:18])-[OH;D1;+0:19]>>[#7;+:8]-[c:9]1:[c:10]:[cH;D2;+0:11]:... | null | [] | 130 | CELSIUS | 14 | HOUR | In an autoclave, 0.274 g of 4-nitrotoluene, 0.011 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to 4-nitrotoluene), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4H2O and 0.001 g of manganese(II) acetate.4H2O were placed. The autoclave was charged with 1 MPa of air and placed in a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde.Carboxylic acid.Nitro group | c1ccccc1.c1ncncn1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].O | 130 | 14 | CC(=O)O.Cc1ccc([N+](=O)[O-])cc1.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].O>O=C(O)c1ccc([N+](=O)[O-])cc1.O=Cc1ccc([N+](=O)[O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29c4d4a941814f3893092bbee75bd8b4 | CC(=O)O.Cc1ccc(C)cc1.O=O>>O=C(O)c1ccc(C(=O)O)cc1 | CC=1C=CC(=CC1)C.ON1C(N(C(N(C1=O)O)=O)O)=O.C(C)(=O)O.CC=1C=CC(=CC1)C.O=O>>C(C1=CC=C(C(=O)O)C=C1)(=O)O | [CH3:7][C:8](=[O:9])[OH:10].Cc1[cH:6][cH:5][c:4]([CH3:2])[cH:12][cH:11]1.[O:1]=[O:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1 | CC(=O)O.Cc1ccc(C)cc1.O=O | O=C(O)c1ccc(C(=O)O)cc1 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | Acylation | OtherReaction | b2c6c66c8e37c7be9aa90948967ec718c6f9c011dab19dcd79b9330bc269e1cd | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | C-c1:[cH;D2;+0:1]:[c:2]:[c:3](-[CH3;D1;+0:4]):[c:5]:[cH;D2;+0:6]:1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[O;H0;D1;+0:11]=[O;H0;D1;+0:12]>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[c;H0;D3;+0:7]1:[cH;D2;+0:1]:[c:2]:[c:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:11])-[OH;D1;+0:12]):[c:5]:[cH;D2;+0:6]:1 | 95 | [{"value": 95.0, "product": "C(C1=CC=C(C(=O)O)C=C1)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.212 g of p-xylene, 0.018 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (5% by mole relative to p-xylene), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4H2O and 0.003 g of manganese(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 14 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | null | CC(=O)O.Cc1ccc(C)cc1.O=O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-]>O=C(O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29285ec6745d475093824ce4bb81f136 | CC(=O)O.Cc1ccc(C)cc1.O=O>>O=C(O)c1ccc(C(=O)O)cc1 | ON1C(N(C(N(C1=O)O)=O)O)=O.C(C)(=O)O.CC=1C=CC(=CC1)C.CC=1C=CC(=CC1)C.CC=1C=CC(=CC1)C.O=O>>C(C1=CC=C(C(=O)O)C=C1)(=O)O | [CH3:7][C:8](=[O:9])[OH:10].Cc1[cH:6][cH:5][c:4]([CH3:2])[cH:12][cH:11]1.[O:1]=[O:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1 | CC(=O)O.Cc1ccc(C)cc1.O=O | O=C(O)c1ccc(C(=O)O)cc1 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | Acylation | OtherReaction | b2c6c66c8e37c7be9aa90948967ec718c6f9c011dab19dcd79b9330bc269e1cd | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | C-c1:[cH;D2;+0:1]:[c:2]:[c:3](-[CH3;D1;+0:4]):[c:5]:[cH;D2;+0:6]:1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10].[O;H0;D1;+0:11]=[O;H0;D1;+0:12]>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[c;H0;D3;+0:7]1:[cH;D2;+0:1]:[c:2]:[c:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:11])-[OH;D1;+0:12]):[c:5]:[cH;D2;+0:6]:1 | 97 | [{"value": 97.0, "product": "C(C1=CC=C(C(=O)O)C=C1)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.212 g of p-xylene, 0.011 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to p-xylene), 0.013 g of N,N′-diacetoxypyromellitdiimide (2% by mole relative to p-xylene), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4H2O and 0.003 g of manganese(II) acetate.4H2O was stirre... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | null | CC(=O)O.Cc1ccc(C)cc1.O=O>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-]>O=C(O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6126e02d02c2469fb6ad8fa1a7eee34a | CC(=O)O.Cc1ccc(C)cc1.O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)c1ccc(C(=O)O)cc1 | ON1C(N(C(N(C1=O)O)=O)O)=O.CC=1C=CC(=CC1)C.O.CC=1C=CC(=CC1)C.C(C)(=O)O>>C(C1=CC=C(C(=O)O)C=C1)(=O)O | [CH3:7][C:8](=[O:9])[OH:10].Cc1[cH:6][cH:5][c:4]([CH3:2])[cH:12][cH:11]1.[OH2:3].O=c1n(O)c(=O)n(O)c(=[O:1])n1O>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1 | CC(=O)O.Cc1ccc(C)cc1.O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)c1ccc(C(=O)O)cc1 | null | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-] | null | Acylation | OtherReaction | 752c1101526c70f4ead31cd94e911c454c4cfed9a7ee5a9f1c62ee1cd062f19c | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | C-c1:[cH;D2;+0:1]:[c:2]:[c:3](-[CH3;D1;+0:4]):[c:5]:[cH;D2;+0:6]:1.O-n1:c(=O):n(-O):c(=[O;H0;D1;+0:7]):n(-O):c:1=O.[CH3;D1;+0:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11].[OH2;D0;+0:12]>>[O;D1;H0:10]=[C:9](-[O;D1;H1:11])-[c;H0;D3;+0:8]1:[cH;D2;+0:1]:[c:2]:[c:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:7])-[OH;D1;+0:12]):[c:5]:[cH;D2;+0:6]... | 99 | [{"value": 99.0, "product": "C(C1=CC=C(C(=O)O)C=C1)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 12 | HOUR | In an autoclave, 0.212 g of p-xylene, 0.011 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to p-xylene), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4H2O, 0.003 g of manganese(II) acetate.4H2O and 0.001 g of zirconium oxyacetate were placed. The autoclave was charged with 2 MPa o... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1.c1ncncn1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-] | 150 | 12 | CC(=O)O.Cc1ccc(C)cc1.O.O=c1n(O)c(=O)n(O)c(=O)n1O>C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-]>O=C(O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67de271df21941b8bcbafcfe8311d58a | Brc1n[nH]c(Br)c1Br.O=[N+]([O-])O>>O=[N+]([O-])n1nc(Br)c(Br)c1Br | [N+](=O)(O)[O-].BrC1=NNC(=C1Br)Br.C(C)(=O)OC(C)=O>>[N+](=O)([O-])N1N=C(C(=C1Br)Br)Br | [nH:4]1[n:5][c:6]([Br:7])[c:8]([Br:9])[c:10]1[Br:11].O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[n:4]1[n:5][c:6]([Br:7])[c:8]([Br:9])[c:10]1[Br:11] | Brc1n[nH]c(Br)c1Br.O=[N+]([O-])O | O=[N+]([O-])n1nc(Br)c(Br)c1Br | null | null | C(C)(=O)O | Functional Group Addition | OtherReaction | 327103570d4042e39411d4fe6402e2268c1a2739c0f9a33725ebfed05ec18181 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cn[nH]c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Br;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[Br;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[n;H0;D3;+0:9]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | 15 | CELSIUS | 2 | HOUR | HNO3 (d=1.50 g/ml; 18 ml, 0.429 mol) was added dropwise over 10 minutes to a solution of 3,4,5-tribromopyrazole (1) (50 g, 0.164 mol) in glacial acetic acid (750 ml) while maintaining the temperature at 15° C. Acetic anhydride (250 ml) was added and the reaction mixture was stirred at room temperature for 2 hours. Once... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1 | HO- | C(C)(=O)O | 15 | 2 | Brc1n[nH]c(Br)c1Br.O=[N+]([O-])O>C(C)(=O)O>O=[N+]([O-])n1nc(Br)c(Br)c1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a84430a84bb465c92f452a6b69a439a | O=[N+]([O-])c1c(Br)n[nH]c1Br.OCCBr>>O=[N+]([O-])c1c(Br)nn(CCO)c1Br | CCCCCC.BrCCO.BrC1=NNC(=C1[N+](=O)[O-])Br.[H-].[Na+]>>BrC1=NN(C(=C1[N+](=O)[O-])Br)CCO | [O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[n:7][nH:8][c:12]1[Br:13].Br[CH2:9][CH2:10][OH:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[n:7][n:8]([CH2:9][CH2:10][OH:11])[c:12]1[Br:13] | O=[N+]([O-])c1c(Br)n[nH]c1Br.OCCBr | O=[N+]([O-])c1c(Br)nn(CCO)c1Br | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1cn[nH]c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[Br;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[Br;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[n;H0;D3;+0:9]:1-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3] | 22 | [{"value": 22.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 10 | MINUTE | A solution of 3,5-dibromo-4-nitropyrazole (2) (11.0 g, 41 mmol) in DMF (52 ml) was added dropwise over 20 min to a stirred solution of NaH (1.76 g, 46 mmol; 60% dispersion in oil, prewashed with hexane under an inert atmosphere) in DMF (88 ml). After stirring for 10 minutes, a solution of 2-bromoethanol (6.4 g, 49 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1 | HBr | CN(C)C=O | 80 | 0.166667 | O=[N+]([O-])c1c(Br)n[nH]c1Br.OCCBr>CN(C)C=O>O=[N+]([O-])c1c(Br)nn(CCO)c1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5a8e2f1fbce433a88bae095a983d4fd | O=[N+]([O-])c1c(Br)nn(CCO)c1Br.ON1CCCC1>>O=[N+]([O-])c1c(Br)nn(CCO)c1N1CCC(O)C1 | BrC1=NN(C(=C1[N+](=O)[O-])Br)CCO.N1(CCCC1)O.CCO>>BrC=1C(=C(N(N1)CCO)N1CC(CC1)O)[N+](=O)[O-] | Br[c:12]1[c:4]([N+:2](=[O:1])[O-:3])[c:5]([Br:6])[n:7][n:8]1[CH2:9][CH2:10][OH:11].[N:13]1([OH:17])[CH2:14][CH2:15][CH2:16][CH2:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([Br:6])[n:7][n:8]([CH2:9][CH2:10][OH:11])[c:12]1[N:13]1[CH2:14][CH2:15][CH:16]([OH:17])[CH2:18]1 | O=[N+]([O-])c1c(Br)nn(CCO)c1Br.ON1CCCC1 | O=[N+]([O-])c1c(Br)nn(CCO)c1N1CCC(O)C1 | null | null | null | Functional Group Addition | OtherReaction | bf588dd0fb3fe850aae840143433e46bb64cc32fa1ed522a18260e0a03216c58 | f3e088125d1ecdf022c33b3555ae5c4ac9053b71630afec64207346bfc4ef1e6 | c1cc(N2CCCC2)[nH]n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2](-[C:3]):[#7;a:4]:[c:5](-[Br;D1;H0:6]):[c:7]:1-[#7;+:8].[OH;D1;+0:9]-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[CH2;D2;+0:13]-[C:14]-1>>[#7;+:8]-[c:7]1:[c:5](-[Br;D1;H0:6]):[#7;a:4]:[#7;a:2](-[C:3]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[CH;D3;+0:13](-[OH;D1;+0:9])-[C:14]-1 | 53 | [{"value": 53.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 2-(3,5-dibromo-4-nitropyrazol-1-yl)ethanol (3) (6.5 g, 21 mmol) and pyrrolidinol (3.75 g, 42 mmol) in EtOH (130 ml) was heated at 60° C. for 15 hours. The reaction was stopped after 67% conversion (monitoring by TLC and HPLC) by evaporating off the solvent under reduced pressure at 40° C. (rotary evaporato... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine | Secondary alcohol.Tertiary amine | c1cn[nH]c1.C1CC[NH]C1 | c1cn[nH]c1.C1CC[NH]C1 | c1cn[nH]c1.C1CC[NH]C1 | HBr | null | 60 | null | O=[N+]([O-])c1c(Br)nn(CCO)c1Br.ON1CCCC1>>O=[N+]([O-])c1c(Br)nn(CCO)c1N1CCC(O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d02271841a334ff1815f17c48731c924 | CSc1nccc(Cl)n1.[F-]>>CSc1nccc(F)n1 | ClC1=NC(=NC=C1)SC.[F-].[K+]>>FC1=NC(=NC=C1)SC | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:9]1.[F-:8]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([F:8])[n:9]1 | CSc1nccc(Cl)n1.[F-] | CSc1nccc(F)n1 | null | C1COCCOCCOCCOCCOCCO1 | COCCOCCOCCOCCOC | Functional Group Interconversion | OtherReaction | 0e5e018dae2d5b301dea7fbf3d4d324b1e81c774be63c615b15b41b2296e4e71 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.[F-;H0;D0:8]>>[#16:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:1](-[F;H0;D1;+0:8]):[#7;a:2]:1 | 63.1 | [{"value": 62.0, "product": "FC1=NC(=NC=C1)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "FC1=NC(=NC=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 16 | HOUR | To a solution of 35.7 g (0.22 mol) of 4-chloro-2-methylthiopyrimidine (Aldrich Chemical Co., Milwaukee, Wis., USA) in 135 mL of tetraglyme was added 18-crown-6 (1.33 g) and potassium fluoride (Anhydrous, Aldrich Chemical Co., Milwaukee, Wis., USA, 80 g). The mixture was heated at 150° C.with stirring for 16 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | C1COCCOCCOCCOCCOCCO1.COCCOCCOCCOCCOC | 150 | 16 | CSc1nccc(Cl)n1.[F-]>C1COCCOCCOCCOCCOCCO1.COCCOCCOCCOCCOC>CSc1nccc(F)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-933511404d6d45dc844e54a6435270b8 | O=C(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F>>OC(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F | C(C)(=O)OCC.O1CCC(CC1)NC=1N=CC2=C(N1)SC(=C2)C(C2=C(C=CC=C2)F)=O.[BH4-].[Na+]>>O1CCC(CC1)NC=1N=CC2=C(N1)SC(=C2)C(O)C2=C(C=CC=C2)F | [O:1]=[C:2]([c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]([NH:9][CH:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[n:16][c:17]2[s:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[F:25]>>[OH:1][CH:2]([c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]([NH:9][CH:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[n:16][c:17]2[s:18]1)[c:19]1[cH:20][cH:21][cH:... | O=C(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F | OC(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F | null | null | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2cc3cnc(NC4CCOCC4)nc3s2)cc1 | [#7;a:1]:[c:2]:[#16;a:3]:[c:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7](:[c:8]):[c:9]):[c:10]>>[#7;a:1]:[c:2]:[#16;a:3]:[c:4](-[CH;D3;+0:5](-[OH;D1;+0:6])-[c:7](:[c:8]):[c:9]):[c:10] | 46.4 | [{"value": 46.4, "product": "O1CCC(CC1)NC=1N=CC2=C(N1)SC(=C2)C(O)C2=C(C=CC=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-(tetrahydropyran-4-ylamino)-6-(2-fluorobenzoyl)thieno[2,3-d]pyrimidine (300 mg) in ethanol (30 mL) was added sodium borohydride (0.4 g) at room temperature and stirred overnight. Ethyl acetate (50 mL) was added to the reaction mixture. The organic layer was separated, washed with brine, dried, and ev... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ncc2ccsc2n1.C1CCOCC1.c1ccccc1 | null | C(C)O | null | 8 | O=C(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F>C(C)O>OC(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-812a26b6b0914c49893210dc67586be6 | OC(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F>>Fc1ccccc1Cc1cc2cnc(NC3CCOCC3)nc2s1 | O1CCC(CC1)NC=1N=CC2=C(N1)SC(=C2)C(O)C2=C(C=CC=C2)F.C(C)[SiH](CC)CC.FC(C(=O)O)(F)F>>O1CCC(CC1)NC=1N=CC2=C(N1)SC(=C2)CC2=C(C=CC=C2)F | O[CH:8]([c:7]1[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]1)[c:9]1[cH:10][c:11]2[cH:12][n:13][c:14]([NH:15][CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[n:22][c:23]2[s:24]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][c:9]1[cH:10][c:11]2[cH:12][n:13][c:14]([NH:15][CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[n:22][c... | OC(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F | Fc1ccccc1Cc1cc2cnc(NC3CCOCC3)nc2s1 | null | null | ClCCl | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(Cc2cc3cnc(NC4CCOCC4)nc3s2)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[#16;a:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[#16;a:7]:[c:5](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:6] | null | [] | null | null | null | null | The alcohol (140 mg) obtained in Example 2A was stirred with triethylsilane (1.0 mL) and trifluoroacetic acid (1.5 mL) in dichloromethane (5 mL) for 4 hours. The solvents were removed. The residue was diluted with toluene (5 mL) and then concentrated. This dilution-concentration process was repeated three times. Purifi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ncc2ccsc2n1.C1CCOCC1 | Other | ClCCl | null | null | OC(c1cc2cnc(NC3CCOCC3)nc2s1)c1ccccc1F>ClCCl>Fc1ccccc1Cc1cc2cnc(NC3CCOCC3)nc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-21abd6ffa22b4380b8d9827c5a327a4a | CCOC(=S)c1cnc(C)nc1Cl.CN>>CCOC(=S)c1cnc(C)nc1NC | O.ClC1=NC(=NC=C1C(=S)OCC)C.CN>>CNC1=NC(=NC=C1C(=S)OCC)C | Cl[c:12]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[S:5])[cH:7][n:8][c:9]([CH3:10])[n:11]1.[NH2:13][CH3:14]>>[CH3:1][CH2:2][O:3][C:4](=[S:5])[c:6]1[cH:7][n:8][c:9]([CH3:10])[n:11][c:12]1[NH:13][CH3:14] | CCOC(=S)c1cnc(C)nc1Cl.CN | CCOC(=S)c1cnc(C)nc1NC | null | null | ClCCl.C(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[#8:9])=[S;D1;H0:10].[C;D1;H3:11]-[NH2;D1;+0:12]>>[#8:9]-[C:8](=[S;D1;H0:10])-[c:7]1:[c:6]:[#7;a:5]:[c:3](-[C;D1;H3:4]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C;D1;H3:11] | 97 | [{"value": 97.0, "product": "CNC1=NC(=NC=C1C(=S)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a 0° C. solution of 20 g (86 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (Aldrich Chemical Co., Milwaukee, Wis., USA) in 250 mL of dichloromethane was slowly added 35 mL (281 mmol) of a 33% solution of methylamine in ethanol. After stirring for 30 minutes, 150 mL of water was added and the phases we... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | ClCCl.C(C)O | null | 0.5 | CCOC(=S)c1cnc(C)nc1Cl.CN>ClCCl.C(C)O>CCOC(=S)c1cnc(C)nc1NC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6762f22478744c559d8ab1ec0f6d6574 | C#CCc1ccccc1.CSc1ncc(I)c(O)n1>>CSc1ncc2cc(Cc3ccccc3)oc2n1 | CSC1=NC=C(C(=N1)O)I.C1(=CC=CC=C1)CC#C>>CSC=1N=CC2=C(N1)OC(=C2)CC2=CC=CC=C2 | [CH:7]#[C:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.I[c:6]1[cH:5][n:4][c:3]([S:2][CH3:1])[n:18][c:17]1[OH:16]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[o:16][c:17]2[n:18]1 | C#CCc1ccccc1.CSc1ncc(I)c(O)n1 | CSc1ncc2cc(Cc3ccccc3)oc2n1 | null | [Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | CN1CCCC1=O.C(C)(=O)OCC.C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | 9de3a79c85595e8bcfe33328f812ec77f9c49a4d36f9efc911ccf1b3db1d31ee | 3fc23ffe9cd1961765663720700ca63e807714902c5edeca2044148e10213397 | c1ccc(Cc2cc3cncnc3o2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[OH;D1;+0:7].[CH;D1;+0:8]#[C;H0;D2;+0:9]-[C:10]-[c:11]>>[c:11]-[C:10]-[c;H0;D3;+0:9]1:[cH;D2;+0:8]:[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:2:[o;H0;D2;+0:7]:1 | null | [] | 40 | CELSIUS | 6 | HOUR | A mixture of 2-methylthio-4-hydroxy-5-iodopyrimidine (2.65 g), 3-phenyl-1-propyne (1.49 mL), copper (I) iodide (90 mg) and bis(triphenylphosphine) Palladium (II) dichloride (Fluka, 160 mg) in 20 mL of triethylamine and NMP (7 mL) was stirred at 40° C. for 6 hours. The reaction mixture was diluted with ethyl acetate (10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Alkyne | null | c1cncnc1 | c1ncc2ccoc2n1 | c1ncc2ccoc2n1.c1ccccc1 | HI | [Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CN1CCCC1=O.C(C)(=O)OCC.C(C)N(CC)CC | 40 | 6 | C#CCc1ccccc1.CSc1ncc(I)c(O)n1>[Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CN1CCCC1=O.C(C)(=O)OCC.C(C)N(CC)CC>CSc1ncc2cc(Cc3ccccc3)oc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7df883d201ce4efdbc637fdbcca76a93 | Cn1c(Cc2ccccc2)cc2cnc(S(C)=O)nc21.NC1CCCC1>>Cn1c(Cc2ccccc2)cc2cnc(NC3CCCC3)nc21 | CS(=O)C=1N=CC2=C(N1)N(C(=C2)CC2=CC=CC=C2)C.C1(CCCC1)N>>C1(CCCC1)NC=1N=CC2=C(N1)N(C(=C2)CC2=CC=CC=C2)C | CS(=O)[c:15]1[n:14][cH:13][c:12]2[cH:11][c:3]([CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[n:2]([CH3:1])[c:23]2[n:22]1.[NH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1>>[CH3:1][n:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[cH:13][n:14][c:15]([NH:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)... | Cn1c(Cc2ccccc2)cc2cnc(S(C)=O)nc21.NC1CCCC1 | Cn1c(Cc2ccccc2)cc2cnc(NC3CCCC3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 6c07232c27ab7f469ae14b0c158ac12a26ccf7144756d004fcf2895ec5a2713c | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | c1ccc(Cc2cc3cnc(NC4CCCC4)nc3[nH]2)cc1 | C-S(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9])-[C:13] | null | [] | 100 | CELSIUS | 8 | HOUR | A mixture of the sulfoxide (50 mg) from Step 3 and cyclopentylamine (1 mL) was stirred at 100° C. overnight. Excess cyclopentylamine was removed and the residue was purified by preparative TLC (25% EtOAc/hexanes) to give the desired product (26 mg). MS: 307.3 (M+H).
Conditions: See reaction.notes.procedure_details.
Wor... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1ccccc1.c1ncc2cc[nH]c2n1.C1CCCC1 | Other | null | 100 | 8 | Cn1c(Cc2ccccc2)cc2cnc(S(C)=O)nc21.NC1CCCC1>>Cn1c(Cc2ccccc2)cc2cnc(NC3CCCC3)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3cdbd0870f345c68c419ba11abf5150 | N#CCC(N)=O.OC1CSC(O)CS1>>NC(=O)c1ccsc1N | OC1SCC(SC1)O.C(#N)CC(=O)N.CO>>NC=1SC=CC1C(=O)N | [NH2:1][C:2](=[O:3])[CH2:4][C:8]#[N:9].OC1C[S:7][CH:6](O)[CH2:5]S1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][s:7][c:8]1[NH2:9] | N#CCC(N)=O.OC1CSC(O)CS1 | NC(=O)c1ccsc1N | null | null | O.C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | 3df8c399e98e797fa1e9a1de1ca73c1ac3f04e5e1dfb707b8253d224ee991d58 | 758c97111232493f397ac2e9f0f7a15661102f40aab9b1a59e2507e43024e9af | c1ccsc1 | O-C1-C-[S;H0;D2;+0:1]-[CH;D3;+0:2](-O)-[CH2;D2;+0:3]-S-1.[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[cH;D2;+0:3]:[cH;D2;+0:2]:[s;H0;D2;+0:1]:[c;H0;D3;+0:8]:1-[NH2;D1;+0:9] | 141.7 | [{"value": 141.7, "product": "NC=1SC=CC1C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,5-Dihydroxy-1,4-dithiane (76 g) and cyanoacetamide (84 g) were added to a mixture of methanol (180 mL), water (10 mL) and triethylamine (10 g). The resulting mixture was heated at 35–40° C. for about 30 minutes while stirring, and then heated to 50–60° C. for an additional 30 minutes with stirring. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary alcohol.Secondary alcohol.Monosulfide.Monosulfide | Primary amine | C1CSCCS1 | c1ccsc1 | c1ccsc1 | Other | O.C(C)N(CC)CC | null | null | N#CCC(N)=O.OC1CSC(O)CS1>O.C(C)N(CC)CC>NC(=O)c1ccsc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a87187d185b4d9390fcb9daeac9bc76 | NC(=O)c1ccsc1N>>O=c1[nH]c(=S)[nH]c2sccc12 | NC=1SC=CC1C(=O)N.C(C)OC(=S)[S-].[K+]>>S=C1NC(C2=C(N1)SC=C2)=O | [O:1]=[C:2]([NH2:3])[c:11]1[c:7]([NH2:6])[s:8][cH:9][cH:10]1>>[O:1]=[c:2]1[nH:3][c:4](=[S:5])[nH:6][c:7]2[s:8][cH:9][cH:10][c:11]12 | NC(=O)c1ccsc1N | O=c1[nH]c(=S)[nH]c2sccc12 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 4fa65667f99e8f6c8c87fad6646067d075948393a06c535f8cb0d1d0aac31b37 | d5e82de9c71c7ccff4195e8161f720b7db735255e625d039d6978528795584cd | O=c1[nH]c(=S)[nH]c2sccc12 | [NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#16;a:7]:[c:8]:1-[NH2;D1;+0:9]>>[O;D1;H0:3]=[c;H0;D3;+0:2]1:[nH;D2;+0:1]:[c:10](=[S;D1;H0:11]):[nH;D2;+0:9]:[c:8]2:[#16;a:7]:[c:6]:[c:5]:[c:4]:2:1 | 69.5 | [{"value": 69.5, "product": "S=C1NC(C2=C(N1)SC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 30 | MINUTE | 2-Amino-thiophene-3-carboxlic acid amide (28.4 g, 0.2 mol) and potassium ethylxanthate (96 g, 3 eq) were mixed together and added to DMF (1000 mL). The resulting mixture was heated to 150° C. for about six hours. The solvent (DMF) was removed on the rotovap under high vacuum at 90° C. The residue was diluted with 600 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | Thiocarbonyl | c1ccsc1 | c1ncc2ccsc2n1 | c1ncc2ccsc2n1 | Other | CN(C)C=O | 150 | 0.5 | NC(=O)c1ccsc1N>CN(C)C=O>O=c1[nH]c(=S)[nH]c2sccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-53c7f10c5ffc4baebb47a80de51c29b8 | CI.O=c1[nH]c(=S)[nH]c2sccc12>>CSc1nc2sccc2c(=O)[nH]1 | C(C)(=O)O.S=C1NC(C2=C(N1)SC=C2)=O.CI>>CSC=1NC(C2=C(N1)SC=C2)=O | I[CH3:1].[S:2]=[c:3]1[nH:4][c:5]2[s:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[nH:12]1>>[CH3:1][S:2][c:3]1[n:4][c:5]2[s:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[nH:12]1 | CI.O=c1[nH]c(=S)[nH]c2sccc12 | CSc1nc2sccc2c(=O)[nH]1 | null | null | [OH-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 92c63a44061a147e48eeed50f826b7022ed515fb552ddc867d89e41eb51ba331 | e73b6e23c9de2770653dfe1c031448ae08eae1a1e8b31e289bfc4b4719e52064 | O=c1[nH]cnc2sccc12 | I-[CH3;D1;+0:1].[S;H0;D1;+0:2]=[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](:[#16;a:8]:[c:9]):[nH;D2;+0:10]:1>>[CH3;D1;+0:1]-[S;H0;D2;+0:2]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](:[#16;a:8]:[c:9]):[n;H0;D2;+0:10]:1 | null | [] | 0 | CELSIUS | 2.5 | HOUR | To a solution of 2-thioxo-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one (25.4 g, 0.138 mol) in 1N aqueous NaOH (600 mL) at room temperature was added methyl iodide (10.3 mL, 1.2 eq). The resulting mixture was stirred vigorously for about 2.5 hours. The reaction mixture was cooled to 0° C. and acetic acid was added (about... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Monosulfide | c1ncc2ccsc2n1 | c1ncc2ccsc2n1 | c1ncc2ccsc2n1 | HI | [OH-].[Na+] | 0 | 2.5 | CI.O=c1[nH]c(=S)[nH]c2sccc12>[OH-].[Na+]>CSc1nc2sccc2c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00809d3f7f04470c97fc72d3e2256184 | CSc1nc2sccc2c(=O)[nH]1.O=P(Cl)(Cl)Cl>>CSc1nc(Cl)c2ccsc2n1 | CSC=1NC(C2=C(N1)SC=C2)=O.O=P(Cl)(Cl)Cl>>ClC=1C2=C(N=C(N1)SC)SC=C2 | O=[c:5]1[nH:4][c:3]([S:2][CH3:1])[n:12][c:11]2[c:7]1[cH:8][cH:9][s:10]2.O=P(Cl)(Cl)[Cl:6]>>[CH3:1][S:2][c:3]1[n:4][c:5]([Cl:6])[c:7]2[cH:8][cH:9][s:10][c:11]2[n:12]1 | CSc1nc2sccc2c(=O)[nH]1.O=P(Cl)(Cl)Cl | CSc1nc(Cl)c2ccsc2n1 | null | null | null | Functional Group Interconversion | OtherReaction | 76035a8fd16fbdce464a23041af581d953a67a3385f057ef866c5378af90d00f | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccsc2n1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](-[#16:5]):[#7;a:6]:[c:7]2:[#16;a:8]:[c:9]:[c:10]:[c:11]:2:1>>[#16:5]-[c:4]1:[#7;a:6]:[c:7]2:[#16;a:8]:[c:9]:[c:10]:[c:11]:2:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:3]:1 | null | [] | 0 | CELSIUS | 1 | HOUR | 2-Methylsulfanyl-3H-thieno[2,3-d]pyrimidin-4-one (12 g, 60.5 mmol) was combined with POCl3 (56 mL), and the resulting mixture was heated to reflux for about 1 hour. The reaction mixture was concentrated under reduced pressure at 50° C. The residue was diluted with ethyl acetate (700 mL) at 0° C. Saturated sodium bicarb... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ncc2ccsc2n1 | c1ncc2ccsc2n1 | c1ncc2ccsc2n1 | HCl | null | 0 | 1 | CSc1nc2sccc2c(=O)[nH]1.O=P(Cl)(Cl)Cl>>CSc1nc(Cl)c2ccsc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6907b10c15a8493fa31b5a4f7ebcd27f | CSc1nc(Cl)c2ccsc2n1>>CS(=O)(=O)c1nc(Cl)c2ccsc2n1 | ClC=1C2=C(N=C(N1)SC)SC=C2.OOS(=O)[O-].[K+].O1CCCC1>>ClC=1C2=C(N=C(N1)S(=O)(=O)C)SC=C2 | [CH3:1][S:2][c:5]1[n:6][c:7]([Cl:8])[c:9]2[cH:10][cH:11][s:12][c:13]2[n:14]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][c:7]([Cl:8])[c:9]2[cH:10][cH:11][s:12][c:13]2[n:14]1 | CSc1nc(Cl)c2ccsc2n1 | CS(=O)(=O)c1nc(Cl)c2ccsc2n1 | null | null | O.C(C)(=O)OCC | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ncc2ccsc2n1 | [#16;a:1]:[c:2]:[#7;a:3]:[c:4](-[S;H0;D2;+0:5]-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[#16;a:1]:[c:2]:[#7;a:3]:[c:4](-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:9])=[O;D1;H0:10]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | To a solution of 4-chloro-2-methylsulfanyl-thieno[2,3-d]pyrimidine (10 g, 46.15 mmol) in tetrahydrofuran (350 mL) at 0° C. was added a solution of OXONE (59.6 g, 2.1 eq) in water (300 mL) dropwise with stirring. The resulting mixture was gradually warmed from 0° C. to room temperature overnight. The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ncc2ccsc2n1 | null | O.C(C)(=O)OCC | null | null | CSc1nc(Cl)c2ccsc2n1>O.C(C)(=O)OCC>CS(=O)(=O)c1nc(Cl)c2ccsc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0a73307f5ab435fad1e94b298214dad | CS(=O)(=O)c1ncc2ccsc2n1.NC1CCOCC1>>c1cc2cnc(NC3CCOCC3)nc2s1 | CS(=O)(=O)C=1N=CC2=C(N1)SC=C2.NC1CCOCC1.CN1C(CCC1)=O>>O1CCC(CC1)NC=1N=CC2=C(N1)SC=C2 | CS(=O)(=O)[c:6]1[n:5][cH:4][c:3]2[cH:2][cH:1][s:16][c:15]2[n:14]1.[NH2:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[cH:1]1[cH:2][c:3]2[cH:4][n:5][c:6]([NH:7][CH:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][c:15]2[s:16]1 | CS(=O)(=O)c1ncc2ccsc2n1.NC1CCOCC1 | c1cc2cnc(NC3CCOCC3)nc2s1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | a70e6e589f29fec6adb83308476f64c40c039378468475a574f6f4f2bb3ebfc0 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | c1cc2cnc(NC3CCOCC3)nc2s1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#16;a:4]:[c:5]):[c:6]:[c:7]:[#7;a:8]:1.[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#16;a:4]:[c:5]):[c:6]:[c:7]:[#7;a:8]:1)-[C:12] | 72.9 | [{"value": 72.9, "product": "O1CCC(CC1)NC=1N=CC2=C(N1)SC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 7 | HOUR | A mixture of 2-methanesulfonyl-thieno[2,3-d]pyrimidine (1.58 g, 7.37 mmol), 4-aminotetrahydropyran (2.24 g, 3 eq) and 1-methyl-2-pyrolidinone (2 mL) was heated to 100° C. with stirring for about 7 hours and continued heating at 80° C. overnight. The reaction mixture was cooled to room temperature and diluted with ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1ncc2ccsc2n1 | c1ncc2ccsc2n1 | c1ncc2ccsc2n1.C1CCOCC1 | HO- | O.C(C)(=O)OCC | 100 | 7 | CS(=O)(=O)c1ncc2ccsc2n1.NC1CCOCC1>O.C(C)(=O)OCC>c1cc2cnc(NC3CCOCC3)nc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20bfb9c6c3334504a550ae3aff9a8c0e | NCCN1CCCC1.O=C(O)c1cccc(Br)c1>>O=C(NCCN1CCCC1)c1cccc(Br)c1 | NCCN1CCCC1.P(=O)(OCC)(OCC)C#N.C(C)N(CC)CC.BrC=1C=C(C(=O)O)C=CC1>>BrC=1C=C(C=CC1)C(=O)NCCN1CCCC1 | [NH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][c:15]([Br:16])[cH:17]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([Br:16])[cH:17]1 | NCCN1CCCC1.O=C(O)c1cccc(Br)c1 | O=C(NCCN1CCCC1)c1cccc(Br)c1 | null | null | O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCN1CCCC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 85.4 | [{"value": 85.4, "product": "BrC=1C=C(C=CC1)C(=O)NCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 1-(2-Aminoethyl)pyrrolidine (4.34 g), diethyl cyanophosphate (5.57 ml) and triethylamine (10.4 ml) were added to a solution of 3-bromobenzoic acid (5.00 g) in N,N-dimethylformamide (DMF; 60 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and then extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccccc1 | HO- | O.CN(C=O)C | null | 16 | NCCN1CCCC1.O=C(O)c1cccc(Br)c1>O.CN(C=O)C>O=C(NCCN1CCCC1)c1cccc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ddb5b33eec07485b9546487bd8670561 | O=C(NCCN1CCCC1)c1cccc(Br)c1.O=Cc1cccc(OB(O)O)c1>>O=Cc1cccc(-c2cccc(C(=O)NCCN3CCCC3)c2)c1 | C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C(C=CC1)C(=O)NCCN1CCCC1.C(=O)C=1C=C(C=CC1)OB(O)O>>C(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1 | Br[c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23]1.OB(O)O[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:24]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][... | O=C(NCCN1CCCC1)c1cccc(Br)c1.O=Cc1cccc(OB(O)O)c1 | O=Cc1cccc(-c2cccc(C(=O)NCCN3CCCC3)c2)c1 | null | null | O.C(C)O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | a9eb3e90aaf615cee8625e192b3441918dcd3559ca5a74d6b87bcc8ceab889cf | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=C(NCCN1CCCC1)c1cccc(-c2ccccc2)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8].O-B(-O)-O-[c;H0;D3;+0:9](:[c:10]:[c:11]-[C:12]=[O;D1;H0:13]):[c:14]:[c:15]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]-[C:12]=[O;D1;H0:13]):[c:14]:[c:15]):[c:7]:[c:8] | null | [] | 90 | CELSIUS | 15 | HOUR | Palladium tetrakistriphenyl phosphine (735 mg) and 2 M aqueous sodium carbonate (21.2 ml) were added to a solution of 3-bromo-N-[2-(1-pyrrolidinyl)ethyl]phenylcarboxamide (6.31 g) in toluene (50 ml), and then a solution of 3-formylphenylboric acid (3.49 g) in ethanol (15 ml) was added thereto, and the mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1CC[NH]C1 | HBr.B | O.C(C)O.C1(=CC=CC=C1)C | 90 | 15 | O=C(NCCN1CCCC1)c1cccc(Br)c1.O=Cc1cccc(OB(O)O)c1>O.C(C)O.C1(=CC=CC=C1)C>O=Cc1cccc(-c2cccc(C(=O)NCCN3CCCC3)c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c113ed0e9c5f49ae997f36f353ec3220 | NCCc1ccc(S(N)(=O)=O)cc1.O=Cc1cccc(-c2cccc(C(=O)NCCN3CCCC3)c2)c1>>NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1 | NCCC1=CC=C(C=C1)S(=O)(=O)N.C(=O)C=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1>>NS(=O)(=O)C1=CC=C(C=C1)CCNCC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1 | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH2:11])[cH:35][cH:36]1.O=[CH:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:33]2)[cH:34]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8... | NCCc1ccc(S(N)(=O)=O)cc1.O=Cc1cccc(-c2cccc(C(=O)NCCN3CCCC3)c2)c1 | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1 | null | null | CO.O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NCCN1CCCC1)c1cccc(-c2cccc(CNCCc3ccccc3)c2)c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1.5 | HOUR | 4-(2-Aminoethyl)benzene sulfonamide (2.37 g) and molecular sieves 3A (4.0 g) were added to a solution of 3′-formyl-N-[2-(1-pyrrolidinyl)ethyl][1,1′-biphenyl]-3-carboxamide (3.81 g) in methanol (50 ml), and the mixture was stirred at room temperature for 1.5 hours. After the reaction mixture was diluted with tetrahydrof... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]C1 | Other | CO.O1CCCC1 | null | 1.5 | NCCc1ccc(S(N)(=O)=O)cc1.O=Cc1cccc(-c2cccc(C(=O)NCCN3CCCC3)c2)c1>CO.O1CCCC1>NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b696eafa817c4dfc8a4718f4178b9314 | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1.O=C(O)/C=C/c1ccccc1>>NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 | NS(=O)(=O)C1=CC=C(C=C1)CCNCC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1.C(\C=C\C1=CC=CC=C1)(=O)O.Cl.C(C)N=C=NCCCN(C)C.ON1N=NC2=C1C=CC=C2>>NS(=O)(=O)C1=CC=C(C=C1)CCN(C(\C=C\C1=CC=CC=C1)=O)CC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1 | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[cH:33]3)[cH:34]2)[cH:45][cH:46]1.O[C:35](=[O:36])/[CH:37]=[CH:38]/[c:39]1[cH:40][cH:41]... | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1.O=C(O)/C=C/c1ccccc1 | NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 | null | null | ClCCl.CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCCN1CCCC1)c1cccc(-c2cccc(CN(CCc3ccccc3)C(=O)/C=C/c3ccccc3)c2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5](:[c:6]):[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[c:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C:11]-[c:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5](:[c:6]):[c:7] | null | [] | null | null | 18 | HOUR | 3′-[{2-[4-(Aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl]-[1,1′-biphenyl]-3-carboxamide (506 mg), trans-cinnamic acid (163 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI.HCl; 211 mg) and 1-hydroxybenzotriazole (HOBT; 149 mg) were dissolved in a mixed solvent of dichlorometha... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | ClCCl.CN(C)C=O | null | 18 | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1.O=C(O)/C=C/c1ccccc1>ClCCl.CN(C)C=O>NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-56cbd7e6389349c0b6ca51767f4aee7b | NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1>>NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 | NS(=O)(=O)C1=CC=C(C=C1)CCN(C(\C=C\C1=CC=CC=C1)=O)CC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1.Cl>>Cl.NS(=O)(=O)C1=CC=C(C=C1)CCN(C(\C=C\C1=CC=CC=C1)=O)CC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1 | [NH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([C:24](=[O:25])[NH:26][CH2:27][CH2:28][N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)[cH:34]3)[cH:35]2)[C:36](=[O:37])/[CH:38]=[CH:39]/[c:40]2[cH:41][cH:42][cH:43][cH:44][c... | NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 | NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(NCCN1CCCC1)c1cccc(-c2cccc(CN(CCc3ccccc3)C(=O)/C=C/c3ccccc3)c2)c1 | null | null | [] | null | null | null | null | 3′-{({2-[4-(Aminosulfonyl)phenyl]ethyl}[(E)-3-phenyl-2-propenoyl]amino)methyl}-N-[2-(1-pyrrolidinyl)ethyl][1,1′-biphenyl]-3-carboxamide (200 mg) was treated with 4 N hydrogen chloride in ethyl acetate to give the title compound (198 mg).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | null | C(C)(=O)OCC | null | null | NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1>C(C)(=O)OCC>NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)/C=C/c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4cc21a4adb5481cb9c9581135c634cc | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1.O=C(Cl)COCc1ccccc1>>NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)COCc2ccccc2)cc1 | N1=CC=CC=C1.C(C1=CC=CC=C1)OCC(=O)Cl.NS(=O)(=O)C1=CC=C(C=C1)CCNCC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1>>NS(=O)(=O)C1=CC=C(C=C1)CCN(C(COCC1=CC=CC=C1)=O)CC=1C=C(C=CC1)C1=CC(=CC=C1)C(=O)NCCN1CCCC1 | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][c:22]([C:23](=[O:24])[NH:25][CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[cH:33]3)[cH:34]2)[cH:46][cH:47]1.Cl[C:35](=[O:36])[CH2:37][O:38][CH2:39][c:40]1[cH:41][... | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1.O=C(Cl)COCc1ccccc1 | NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)COCc2ccccc2)cc1 | null | null | O.CN(C)C=O | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(NCCN1CCCC1)c1cccc(-c2cccc(CN(CCc3ccccc3)C(=O)COCc3ccccc3)c2)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[c:9]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[c:9] | null | [] | null | null | 16 | HOUR | Pyridine (0.16 ml) and benzyloxyacetyl chloride (0.16 ml) were added to a solution of 3′-[{2-[4-(aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl]-[1,1′-biphenyl]-3-carboxamide (506 mg) in DMF (10 ml). The reaction mixture was stirred at room temperature for 16 hours, then diluted with water and extra... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | HCl | O.CN(C)C=O | null | 16 | NS(=O)(=O)c1ccc(CCNCc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)cc1.O=C(Cl)COCc1ccccc1>O.CN(C)C=O>NS(=O)(=O)c1ccc(CCN(Cc2cccc(-c3cccc(C(=O)NCCN4CCCC4)c3)c2)C(=O)COCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f99820706bd4c3aa363011fd560dde5 | C=CC(=O)OC.O=Cc1ccccc1>>C=C(C(=O)OC)C(O)c1ccccc1 | N12NCC(CC1)CC2.C(C1=CC=CC=C1)=O.C(C=C)(=O)OC>>OC(C(C(=O)OC)=C)C1=CC=CC=C1 | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH3:6].[CH:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH3:6])[CH:7]([OH:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | C=CC(=O)OC.O=Cc1ccccc1 | C=C(C(=O)OC)C(O)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | c1ccccc1 | [C;D1;H2:1]=[CH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H2:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[CH;D3;+0:8](-[OH;D1;+0:7])-[c:9](:[c:10]):[c:11] | 77 | [{"value": 77.0, "product": "OC(C(C(=O)OC)=C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "OC(C(C(=O)OC)=C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | DAY | Diazabicyclo[2.2.2]octane (5.2 g, 0.046 mol, 0.15 eq) was added to a mixture of benzaldehyde (31.5 mL, 0.309 mol, 1 eq) and methyl acrylate (42 mL, 0.464 mol, 1.5 eq). The reaction mixture was then allowed to stir at room temperature for 7 days. The reaction mixture was purified by column chromatography (eluent: hexane... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1 | null | null | null | 168 | C=CC(=O)OC.O=Cc1ccccc1>>C=C(C(=O)OC)C(O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51582f8a327c4533891b280b894aa847 | C=C(C(=O)OC)[C@@H](O)c1ccccc1>>C=C(C(=O)O)[C@@H](O)c1ccccc1 | [OH-].[K+].O[C@H](C(C(=O)OC)=C)C1=CC=CC=C1>>O[C@H](C(C(=O)O)=C)C1=CC=CC=C1 | C[O:5][C:3]([C:2](=[CH2:1])[C@@H:6]([OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:4]>>[CH2:1]=[C:2]([C:3](=[O:4])[OH:5])[C@@H:6]([OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | C=C(C(=O)OC)[C@@H](O)c1ccccc1 | C=C(C(=O)O)[C@@H](O)c1ccccc1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5])=[C;D1;H2:6]>>[C:5]-[C:4](=[C;D1;H2:6])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of potassium hydroxide (2.27 g, 0.040 mol, 1.3 eq) in water (45 mL) was added drop wise to a solution of 1a (6 g, 0.031 mol, 1 eq) in methanol (15 mL) (see FIG. 4). The mixture was stirred at room temperature for 15 h. The solution was then concentrated under vacuum. The aqueous phase was washed with ether (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO.O | null | 15 | C=C(C(=O)OC)[C@@H](O)c1ccccc1>CO.O>C=C(C(=O)O)[C@@H](O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2591f3d8c244c90ae1d4040f2513ff7 | C=C(C(=O)O)[C@@H](O)c1ccccc1.CCOC(=O)CN>>C=C(C(=O)NCC(=O)OCC)[C@@H](O)c1ccccc1 | C(C)N(CC)CC.Cl.C(C)OC(CN)=O.O[C@H](C(C(=O)O)=C)C1=CC=CC=C1.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)OC(CNC(C([C@H](C1=CC=CC=C1)O)=C)=O)=O | O[C:3]([C:2](=[CH2:1])[C@@H:12]([OH:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[O:4].[NH2:5][CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11]>>[CH2:1]=[C:2]([C:3](=[O:4])[NH:5][CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11])[C@@H:12]([OH:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | C=C(C(=O)O)[C@@H](O)c1ccccc1.CCOC(=O)CN | C=C(C(=O)NCC(=O)OCC)[C@@H](O)c1ccccc1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])=[C;D1;H2:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[NH2;D1;+0:11]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])=[C;D1;H2:5] | 60 | [{"value": 60.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Triethylamine (3.75 mL, 0.027 mol, 1.2 eq) was added to a suspension of glycine ethyl ester hydrochloride (3.44 g, 0.024 mol, 1.1 eq) in anhydrous dichloromethane (60 mL) (see FIG. 4). The mixture was stirred for 15 min at room temperature and then cooled to 0° C. (ice bath). Compound 9a (4 g, 0.022 mol, 1 eq) and dicy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | ClCCl | null | 0.25 | C=C(C(=O)O)[C@@H](O)c1ccccc1.CCOC(=O)CN>ClCCl>C=C(C(=O)NCC(=O)OCC)[C@@H](O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f64186500de404a9bed21e70c5814fb | C=C(C(=O)OC)C(O)c1ccccc1>>C=C(C(=O)O)[C@H](O)c1ccccc1 | [OH-].[K+].OC(C(C(=O)OC)=C)C1=CC=CC=C1>>O[C@@H](C(C(=O)O)=C)C1=CC=CC=C1 | C[O:5][C:3]([C:2](=[CH2:1])[CH:6]([OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:4]>>[CH2:1]=[C:2]([C:3](=[O:4])[OH:5])[C@H:6]([OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | C=C(C(=O)OC)C(O)c1ccccc1 | C=C(C(=O)O)[C@H](O)c1ccccc1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5])=[C;D1;H2:6]>>[C:5]-[C:4](=[C;D1;H2:6])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 97 | [{"value": 97.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of potassium hydroxide (2.65 g, 0.047 mol, 1.3 eq) in water (60 mL) was added drop wise to a solution of 1b (7 g, 0.036 mol, 1 eq) in methanol (20 mL) (see FIG. 5). The mixture was stirred at room temperature for 15 h. The solution was then concentrated under vacuum. The aqueous phase was washed with ether (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO.O | null | 15 | C=C(C(=O)OC)C(O)c1ccccc1>CO.O>C=C(C(=O)O)[C@H](O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbd607b812354346904cf9218fbabf16 | O=C(O)C(Cc1ccccc1)C(=O)O>>C=C(Cc1ccccc1)C(=O)O | Cl.C(C1=CC=CC=C1)C(C(=O)O)C(=O)O.C=O.C(C)NCC>>C=C(C(=O)O)CC1=CC=CC=C1 | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12] | O=C(O)C(Cc1ccccc1)C(=O)O | C=C(Cc1ccccc1)C(=O)O | null | null | O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 05c08187bcfd48bcdefffc418b1b8d1f6998c5bedcb14c599f289704901fa8bf | f72397e2bf1ed63b336420ad8491805dec3139bd28093f1f8ae2a191ad5039cf | c1ccccc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[CH2;D1;+0:1]=[C;H0;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 90 | [{"value": 90.0, "product": "C=C(C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "C=C(C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzylmalonic acid (20.0 g, 0.103 mol, 1 eq) and paraformaldehyde (4.94 g, 0.164 mol, 1.6 eq) in ethyl acetate (150 mL) was cooled (0° C.) and treated with diethylamine (10.65 mL, 0.103 mol, 1 eq) drop wise, keeping the reaction temperature below 20° C. (see FIG. 6). The reaction was then warmed to reflux... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Vinyl | null | null | c1ccccc1 | Other | O.C(C)(=O)OCC | null | null | O=C(O)C(Cc1ccccc1)C(=O)O>O.C(C)(=O)OCC>C=C(Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc1ed22dc80b45699a119d3e840b40f3 | C=C(Cc1ccccc1)C(=O)O.CCOC(=O)CN>>C=C(Cc1ccccc1)C(=O)NCC(=O)OCC | C(C)N(CC)CC.Cl.C(C)OC(CN)=O.C=C(C(=O)O)CC1=CC=CC=C1.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)OC(CNC(C(CC1=CC=CC=C1)=C)=O)=O | O[C:10]([C:2](=[CH2:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)=[O:11].[NH2:12][CH2:13][C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[NH:12][CH2:13][C:14](=[O:15])[O:16][CH2:17][CH3:18] | C=C(Cc1ccccc1)C(=O)O.CCOC(=O)CN | C=C(Cc1ccccc1)C(=O)NCC(=O)OCC | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])=[C;D1;H2:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[NH2;D1;+0:11]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])=[C;D1;H2:5] | 83 | [{"value": 83.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Triethylamine (3.10 mL, 0.022 mol, 1.2 eq) was added to a suspension of glycine ethyl ester hydrochloride (2.84 g, 0.020 mol, 1.1 eq) in anhydrous dichloromethane (100 mL) (see FIG. 6). The mixture was stirred for 15 min at room temperature and then cooled to 0° C. (ice bath). Compound 17 (3 g, 0.018 mol, 1 eq) and dic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | ClCCl | null | 0.25 | C=C(Cc1ccccc1)C(=O)O.CCOC(=O)CN>ClCCl>C=C(Cc1ccccc1)C(=O)NCC(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c2877b65fa545ce942d266c2a7f2895 | CCCCC#CCCO>>CCCC/C=C/CCO | [Li].N.C(CC#CCCCC)O.CC(C)(C)O.N>>C(C\C=C\CCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][OH:9]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]/[CH2:7][CH2:8][OH:9] | CCCCC#CCCO | CCCC/C=C/CCO | null | null | C1CCOC1 | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5]-[C:6]>>[C:1]-[C:2]/[CH;D2;+0:3]=[CH;D2;+0:4]/[C:5]-[C:6] | 95.2 | [{"value": 95.0, "product": "C(C\\C=C\\CCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "C(C\\C=C\\CCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of oct-3-yn-1-ol (2.52 g, 20.0 mmol), t-BuOH (5 g), THF (10 mL) and liquid NH3 was cooled to −36° C. Pieces of Lithium (0.34 g, 50 mmol) were introduced with vigorous stirrng and maintaining the temperature. After 2 h, NH3 was allowed to evaporate overnight. Saturated NH4Cl solution was added and the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | null | null | C1CCOC1 | null | 2 | CCCCC#CCCO>C1CCOC1>CCCC/C=C/CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab1539e727ce4dc0bb73166930e09369 | CCCC/C=C/CCO.O=C1CCC(=O)N1Br>>CCCC/C=C/CCBr | C1CC(=O)N(C1=O)Br.C(C\C=C\CCCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCC\C=C\CCCC | O[CH2:8][CH2:7]/[CH:6]=[CH:5]/[CH2:4][CH2:3][CH2:2][CH3:1].O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]/[CH2:7][CH2:8][Br:9] | CCCC/C=C/CCO.O=C1CCC(=O)N1Br | CCCC/C=C/CCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]/[C:3]=[C:4]/[C:5].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:6]>>[Br;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2]/[C:3]=[C:4]/[C:5] | 73.3 | [{"value": 73.0, "product": "BrCC\\C=C\\CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "BrCC\\C=C\\CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of trans-oct-3-en-1-ol (1.28 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.1 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was di... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CCCC/C=C/CCO.O=C1CCC(=O)N1Br>CN(C)C=O>CCCC/C=C/CCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5252b372b2d4d16afed6358ce3bccce | CCCC/C=C/CCBr.CN1CCC[C@H]1c1cccnc1>>Br.CCCC/C=C/CC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCC\C=C\CCCC>>Br.[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CC\C=C\CCCC | [Br:1][CH2:9][CH2:8]/[CH:7]=[CH:6]/[CH2:5][CH2:4][CH2:3][CH3:2].[n:10]1[cH:11][cH:12][cH:13][c:14]([C@@H:15]2[CH2:16][CH2:17][CH2:18][N:19]2[CH3:20])[cH:21]1>>[BrH:1].[CH3:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][CH2:9][n+:10]1[cH:11][cH:12][cH:13][c:14]([C@@H:15]2[CH2:16][CH2:17][CH2:18][N:19]2[CH3:20])[cH:21]1.[... | CCCC/C=C/CCBr.CN1CCC[C@H]1c1cccnc1 | Br.CCCC/C=C/CC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]/[C:4]=[C:5]/[C:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[BrH;D0;+0:1].[C:6]/[C:5]=[C:4]/[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:8]:[c:7]):[c:10]:[c:11] | 62.5 | [{"value": 62.0, "product": "Br.[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CC\\C=C\\CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.5, "product": "Br.[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CC\\C=C\\CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.46 g, 2.8 mmol) in AcOH (10 ml) was added trans-1-bromo-oct-3-ene (1.37 g, 7.17 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-trans-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-enyl-pyridin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCCC/C=C/CCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CCCC/C=C/CC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3045a0f05464439483f978fcd3de00c1 | CCCCC/C=C/CCC=O>>CCCCC/C=C/CCCO | [BH4-].[Na+].C(CC\C=C\CCCCC)=O.[NH4+].[Cl-]>>C(CC\C=C\CCCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH:10]=[O:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][OH:11] | CCCCC/C=C/CCC=O | CCCCC/C=C/CCCO | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | null | [C:1]=[C:2]/[C:3]-[C:4]-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[C:1]=[C:2]/[C:3]-[C:4]-[CH2;D2;+0:5]-[OH;D1;+0:6] | 97.3 | [{"value": 97.0, "product": "C(CC\\C=C\\CCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "C(CC\\C=C\\CCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium borohydride (0.60 g, 3.8 mmol) was added in portions to a stirred solution of trans-dec-4-enal (1.54 g, 10.0 mmol) in methanol (50 mL). The reaction was stirred at room temperature for 30 min followed by the addition of saturated NH4Cl. Methanol was evaporated and water was added to the residue. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | null | null | CO | null | 0.5 | CCCCC/C=C/CCC=O>CO>CCCCC/C=C/CCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e72ef16052e45c89ba94b6b658974be | CCCCC/C=C/CCCO.O=C1CCC(=O)N1Br>>CCCCC/C=C/CCCBr | C1CC(=O)N(C1=O)Br.C(CC\C=C\CCCCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCC\C=C\CCCCC | O[CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]/[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].O=C1CCC(=O)N1[Br:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][Br:11] | CCCCC/C=C/CCCO.O=C1CCC(=O)N1Br | CCCCC/C=C/CCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:6]>>[Br;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5] | 75 | [{"value": 75.0, "product": "BrCCC\\C=C\\CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "BrCCC\\C=C\\CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of trans-dec-4-en-1-ol (1.52 g, 9.74 mmol) in DMF (25 mL) was added triphenylphosphine (2.81 g, 10.7 mmol). The solution was cooled to 0° C. and NBS (1.85 g, 10.4 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was di... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CCCCC/C=C/CCCO.O=C1CCC(=O)N1Br>CN(C)C=O>CCCCC/C=C/CCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e9bf89dccf542e48fad94bcad548578 | CCCCC/C=C/CCCBr.CN1CCC[C@H]1c1cccnc1>>CCCCC/C=C/CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCC\C=C\CCCCC>>[Br-].C(CC\C=C\CCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][Br:23].[n:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3:21])[cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][n+:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:... | CCCCC/C=C/CCCBr.CN1CCC[C@H]1c1cccnc1 | CCCCC/C=C/CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]/[C:5]=[C:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[Br-;H0;D0:1].[C:6]=[C:5]/[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:8]:[c:7]):[c:10]:[c:11] | 74.1 | [{"value": 74.0, "product": "[Br-].C(CC\\C=C\\CCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "[Br-].C(CC\\C=C\\CCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.47 g, 2.9 mmol) in AcOH (15 ml) was added trans-1-bromo-dec-4-ene (1.55 g, 7.08 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCCCC/C=C/CCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>CCCCC/C=C/CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3dadb7fa34ef4294929d576b1cfc5657 | CCCC/C=C\CCO.O=C1CCC(=O)N1Br>>CCCC/C=C\CCBr | C1CC(=O)N(C1=O)Br.C(C\C=C/CCCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCC\C=C/CCCC | O[CH2:8][CH2:7]/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][CH3:1].O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][Br:9] | CCCC/C=C\CCO.O=C1CCC(=O)N1Br | CCCC/C=C\CCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]/[C:3]=[C:4]\[C:5].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:6]>>[Br;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2]/[C:3]=[C:4]\[C:5] | 91.1 | [{"value": 91.0, "product": "BrCC\\C=C/CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "BrCC\\C=C/CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of cis-oct-3-en-1-ol (1.00 g, 7.81 mmol) in DMF (18 mL) was added triphenylphosphine (2.28 g, 8.69 mmol). The solution was cooled to 0° C. and NBS (1.50 g, 8.43 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was dilu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CCCC/C=C\CCO.O=C1CCC(=O)N1Br>CN(C)C=O>CCCC/C=C\CCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f119762236ac4a1795b51bc76e49884b | CCCC/C=C\CCBr.CN1CCC[C@H]1c1cccnc1>>Br.CCCC/C=C\CC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCC\C=C/CCCC>>Br.[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CC\C=C/CCCC | [Br:1][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH3:2].[n:10]1[cH:11][cH:12][cH:13][c:14]([C@@H:15]2[CH2:16][CH2:17][CH2:18][N:19]2[CH3:20])[cH:21]1>>[BrH:1].[CH3:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][n+:10]1[cH:11][cH:12][cH:13][c:14]([C@@H:15]2[CH2:16][CH2:17][CH2:18][N:19]2[CH3:20])[cH:21]1.[... | CCCC/C=C\CCBr.CN1CCC[C@H]1c1cccnc1 | Br.CCCC/C=C\CC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]/[C:4]=[C:5]\[C:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[BrH;D0;+0:1].[C:6]/[C:5]=[C:4]\[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:8]:[c:7]):[c:10]:[c:11] | 49.2 | [{"value": 49.0, "product": "Br.[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CC\\C=C/CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.2, "product": "Br.[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CC\\C=C/CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.47 g, 2.9 mmol) in AcOH (8 ml) was added cis-1-bromo-oct-3-ene (1.34 g, 7.00 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-cis-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-enyl-pyridinium b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCCC/C=C\CCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CCCC/C=C\CC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-250bb15c7a244c6db29dddc3306f653d | CCCCC/C=C\CCCO.O=C1CCC(=O)N1Br>>CCCCC/C=C\CCCBr | C1CC(=O)N(C1=O)Br.C(CC\C=C/CCCCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCC\C=C/CCCCC | O[CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].O=C1CCC(=O)N1[Br:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][Br:11] | CCCCC/C=C\CCCO.O=C1CCC(=O)N1Br | CCCCC/C=C\CCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:6]>>[Br;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3]/[C:4]=[C:5] | 96 | [{"value": 96.0, "product": "BrCCC\\C=C/CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "BrCCC\\C=C/CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of cis-dec-4-en-1-ol (1.00 g, 6.41 mmol) in DMF (15 mL) was added triphenylphosphine (1.87 g, 7.13 mmol). The solution was cooled to 0° C. and NBS (1.23 g, 6.91 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.6 mL). The solution was di... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CCCCC/C=C\CCCO.O=C1CCC(=O)N1Br>CN(C)C=O>CCCCC/C=C\CCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46186120e63646d3982a402cf138b971 | CCCCC/C=C\CCCBr.CN1CCC[C@H]1c1cccnc1>>Br.CCCCC/C=C\CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCC\C=C/CCCCC>>Br.[Br-].C(CC\C=C/CCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [Br:1][CH2:11][CH2:10][CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][CH2:3][CH3:2].[n:12]1[cH:13][cH:14][cH:15][c:16]([C@@H:17]2[CH2:18][CH2:19][CH2:20][N:21]2[CH3:22])[cH:23]1>>[BrH:1].[CH3:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][n+:12]1[cH:13][cH:14][cH:15][c:16]([C@@H:17]2[CH2:18][CH2:19][C... | CCCCC/C=C\CCCBr.CN1CCC[C@H]1c1cccnc1 | Br.CCCCC/C=C\CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]/[C:5]=[C:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[BrH;D0;+0:1].[C:6]=[C:5]\[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:8]:[c:7]):[c:10]:[c:11] | 54 | [{"value": 54.0, "product": "Br.[Br-].C(CC\\C=C/CCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "Br.[Br-].C(CC\\C=C/CCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.35 g, 2.2 mmol) in AcOH (10 ml) was added cis-1-bromo-dec-4-ene (1.15 g, 5.25 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-cis-1-dec-4-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCCCC/C=C\CCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CCCCC/C=C\CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44caa68fa2d0420e80f2c7acc69a0271 | C=CCCCCCCBr.CN1CCC[C@H]1c1cccnc1>>C=CCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCC=C>>[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCCCCCC=C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:21].[n:9]1[cH:10][cH:11][cH:12][c:13]([C@@H:14]2[CH2:15][CH2:16][CH2:17][N:18]2[CH3:19])[cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][n+:9]1[cH:10][cH:11][cH:12][c:13]([C@@H:14]2[CH2:15][CH2:16][CH2:17][N:18]2[CH3:19])[cH:20]1.[Br-:21] | C=CCCCCCCBr.CN1CCC[C@H]1c1cccnc1 | C=CCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | 77 | [{"value": 77.0, "product": "[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCCCCCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.12 g, 0.71 mmol) in AcOH (2 ml) was added 8-bromo-oct-1-ene (0.34 g, 1.8 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | C=CCCCCCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>C=CCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e3ad5c77d6a4913a7de709d2d308fb0 | C=CCCCCCCCCO.O=C1CCC(=O)N1Br>>C=CCCCCCCCCBr | C1CC(=O)N(C1=O)Br.C(CCCCCCCC=C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCCCC=C | O[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].O=C1CCC(=O)N1[Br:11]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Br:11] | C=CCCCCCCCCO.O=C1CCC(=O)N1Br | C=CCCCCCCCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 81 | [{"value": 81.0, "product": "BrCCCCCCCCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "BrCCCCCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of dec-9-en-1-ol (1.22 g, 7.82 mmol) in DMF (18 mL) was added triphenylphosphine (2.30 g, 8.77 mmol). The solution was cooled to 0° C. and NBS (1.52 g, 8.54 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.8 mL). The solution was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | C=CCCCCCCCCO.O=C1CCC(=O)N1Br>CN(C)C=O>C=CCCCCCCCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66a448c2e461469eb54984eb9da3b1dc | C=CCCCCCCCCBr.CN1CCC[C@H]1c1cccnc1>>C=CCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCCCC=C>>[Br-].C(CCCCCCCC=C)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Br:23].[n:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3:21])[cH:22]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n+:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20... | C=CCCCCCCCCBr.CN1CCC[C@H]1c1cccnc1 | C=CCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | 61 | [{"value": 61.0, "product": "[Br-].C(CCCCCCCC=C)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.6, "product": "[Br-].C(CCCCCCCC=C)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.52 g, 3.2 mmol) in AcOH (10 ml) was added 10-bromo-dec-1-ene (1.66 g, 7.58 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | C=CCCCCCCCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>C=CCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86f52034622e4a4282757f1129537775 | C#CCCCCCCCCCO>>C=CCCCCCCCCCO | C(CCCCCCCCC#C)O.N1=CC=CC2=CC=CC=C12>>C(CCCCCCCCC=C)O | [CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12] | C#CCCCCCCCCCO | C=CCCCCCCCCCO | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | CCO | Reduction | Hydrogenation (triple to double) | 9f52c8974802286f8820d0e5a1138949841bf279f003e6bdb19791e6c7026201 | b33c1ae638dee5a1423c3ff5f0ee5b5756446f824b47de64dde7b069c4ebf43c | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[CH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4] | 101 | [{"value": 100.0, "product": "C(CCCCCCCCC=C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.0, "product": "C(CCCCCCCCC=C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of undec-10-yn-1-ol (0.84 g, 5.0 mmol), quinoline (0.13 ml), Lindlar's catalyst (100 mg, 17% w/w) and EtOH (20 mL) was hydrogenated in a Parr apparatus at 50 psi of H2 for 1 h. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to dryness to give undec-10-en-1-ol (0.86 g, 100%... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Allyl | null | null | null | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].CCO | null | 1 | C#CCCCCCCCCCO>[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].CCO>C=CCCCCCCCCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfcf2e5c697c4214b18cca6e5a6f6fc5 | C=CCCCCCCCCCO.O=C1CCC(=O)N1Br>>C=CCCCCCCCCCBr | C1CC(=O)N(C1=O)Br.C(CCCCCCCCC=C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCCCCC=C | O[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].O=C1CCC(=O)N1[Br:12]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12] | C=CCCCCCCCCCO.O=C1CCC(=O)N1Br | C=CCCCCCCCCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 82.3 | [{"value": 82.0, "product": "BrCCCCCCCCCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "BrCCCCCCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of undec-10-en-1-ol (0.86 g, 5.0 mmol) in DMF (15 mL) was added triphenylphosphine (1.46 g, 5.6 mmol). The solution was cooled to 0° C. and NBS (0.96 g, 5.4 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 mL). The solution was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | C=CCCCCCCCCCO.O=C1CCC(=O)N1Br>CN(C)C=O>C=CCCCCCCCCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce7b95b732fa4825b979290ff90e7f3b | C=CCCCCCCCCCBr.CN1CCC[C@H]1c1cccnc1>>C=CCCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCCCCC=C>>[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCCCCCCCCC=C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:24].[n:12]1[cH:13][cH:14][cH:15][c:16]([C@@H:17]2[CH2:18][CH2:19][CH2:20][N:21]2[CH3:22])[cH:23]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][n+:12]1[cH:13][cH:14][cH:15][c:16]([C@@H:17]2[CH2:18][CH2:... | C=CCCCCCCCCCBr.CN1CCC[C@H]1c1cccnc1 | C=CCCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | 67 | [{"value": 67.0, "product": "[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCCCCCCCCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCCCCCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.14 g, 0.86 mmol) in AcOH (4 ml) was added 11-bromo-undec-1-ene (0.50 g, 2.1 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and drie... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | C=CCCCCCCCCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>C=CCCCCCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aade5df588aa4d7984bc144871052427 | CO.O=C1CCCCCO1>>COC(=O)CCCCCO | C1(CCCCCO1)=O.OS(=O)(=O)O.CO>>COC(CCCCCO)=O | [CH3:1][OH:2].[C:3]1(=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10] | CO.O=C1CCCCCO1 | COC(=O)CCCCCO | null | null | null | Protection | OtherReaction | 86aeab1fe7786bf8c336046b3e04b79e984738abf14e78f0855541a3495f221d | a87b94e4ea3a93e5c94bd0993c5a90f9386746ba066362d4c8f843155ae3cfcd | null | [C;D1;H3:1]-[OH;D1;+0:2].[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[C:8]-[C:9]>>[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:2]-[C;D1;H3:1].[C:9]-[C:8]-[OH;D1;+0:7] | null | [] | null | null | null | null | A solution of ε-caprolactone (11.4 g, 0.100 mol), MeOH (300 mL) and concentrated H2SO4 (5 mL) was refluxed overnight. The resulting mixture was cooled to room temperature and concentrated. Water was added to the residue and the pH was adjusted to 7 with solid NaHCO3. The aqueous layer was extracted with ether. The comb... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Methanol | Ester.Primary alcohol | C1CCCOCC1 | null | null | null | null | null | null | CO.O=C1CCCCCO1>>COC(=O)CCCCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e8fb063cff74ebcb0d4c77b40a93c43 | CC(=O)[O-].CCOCC.[O]=[Cr](=[O])([O-])[Cl]>>COC(=O)CCCCC=O | CCOCC.C(C)(=O)[O-].[Na+].C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl>>COC(CCCCC=O)=O | [O-:2][C:3](=[O:4])[CH3:5].C[CH2:1]O[CH2:7][CH3:6].[O]=[Cr]([O-])([Cl])=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[O:10] | CC(=O)[O-].CCOCC.[O]=[Cr](=[O])([O-])[Cl] | COC(=O)CCCCC=O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a5469d918040993eefcca6d6926f9a1605a15e64525dd40b452c435180ad5f90 | 29ae0449eac60db6bfa35546a3f8e4c32df85fc967152b7c1eb7b7f590729ee2 | null | C-[CH2;D2;+0:1]-O-[CH2;D2;+0:2]-[CH3;D1;+0:3].[CH3;D1;+0:4]-[C:5](-[O-;H0;D1:6])=[O;D1;H0:7].[Cl]-[Cr](-[O-])(=[O;H0;D1;+0:8])=[O]>>[CH3;D1;+0:1]-[O;H0;D2;+0:6]-[C:5](=[O;D1;H0:7])-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[C:9]-[C:10]=[O;H0;D1;+0:8] | 60 | [{"value": 60.0, "product": "COC(CCCCC=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The foregoing crude product was dissolved in CH2Cl2 (300 mL). Sodium acetate (2.6 g, 32 mmol) and PCC (32.7 g, 50 mmol) was added. After being stirred at room temperature for 2 h, ether (2000 mL) was added, the reaction mixture was filtered through Florisil, and the filtrate was concentrated. The residue was distilled ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aldehyde.Ester | null | null | null | HCl | C(Cl)Cl | null | 2 | CC(=O)[O-].CCOCC.[O]=[Cr](=[O])([O-])[Cl]>C(Cl)Cl>COC(=O)CCCCC=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-632b3aefbc274b3face44a650ef151e3 | COC(=O)CCCCC=C1CCC1>>OCCCCCC=C1CCC1 | COC(CCCCC=C1CCC1)=O.CC(C)C[AlH]CC(C)C>>C1(CCC1)=CCCCCCO | CO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11]1 | COC(=O)CCCCC=C1CCC1 | OCCCCCC=C1CCC1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | [CH]=C1CCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 6-cyclobutylidene-hexanoic acid methyl ester (0.60 g, 3.3 mmol) in toluene (30 mL) was added DIBAL-H (8.2 mL, 1 M solution in hexane, 8.2 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (3 mL). Saturated aqueous sodium potassium tartrate (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCC1 | Other | C1(=CC=CC=C1)C | 0 | 0.5 | COC(=O)CCCCC=C1CCC1>C1(=CC=CC=C1)C>OCCCCCC=C1CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09cc941842a840ad9c1eb2fc2d6cd7a5 | O=C1CCC(=O)N1Br.OCCCCCCC1CCC1>>BrCCCCCCC1CCC1 | C1CC(=O)N(C1=O)Br.C1(CCC1)CCCCCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCC1CCC1 | O=C1CCC(=O)N1[Br:1].O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11]1 | O=C1CCC(=O)N1Br.OCCCCCCC1CCC1 | BrCCCCCCC1CCC1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | C1CCC1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 91.3 | [{"value": 91.0, "product": "BrCCCCCCC1CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "BrCCCCCCC1CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 6-cyclobutyl-hexan-1-ol (0.47 g, 3.0 mmol) in DMF (10 mL) was added triphenylphosphine (0.88 g, 3.4 mmol). The solution was cooled to 0° C. and NBS (0.57 g, 3.2 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 mL). The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | C1CCC1 | HO- | CN(C)C=O | 0 | 0.5 | O=C1CCC(=O)N1Br.OCCCCCCC1CCC1>CN(C)C=O>BrCCCCCCC1CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fb54d85d9a24981b7dd3b8ef0fa33e9 | BrCCCCCCC1CCC1.CN1CCC[C@H]1c1cccnc1>>Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCC2)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCC1CCC1>>Br.[Br-].C1(CCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [Br:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22]1.[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][n:12][cH:23]1>>[BrH:1].[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][n+:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[CH2:20]... | BrCCCCCCC1CCC1.CN1CCC[C@H]1c1cccnc1 | Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCC2)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1cc([C@@H]2CCCN2)c[n+](CCCCCCC2CCC2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[BrH;D0;+0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | 61 | [{"value": 61.0, "product": "Br.[Br-].C1(CCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.0, "product": "Br.[Br-].C1(CCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stired solution of (S)-nicotine (0.18 g, 1.1 mmol) in AcOH (4 ml) was added (6-bromo-hexyl)cyclobutane (0.59 g, 2.7 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-1-(6-cyclobutyl-hexyl)-3-(1-methyl-pyrrolidin-2-yl)-pyr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1CC[NH]C1.C1=CC=[NH+]C=C1.C1CCC1 | null | CC(=O)O | null | null | BrCCCCCCC1CCC1.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCC2)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f79367d3b22246648a2444da9ffbe6c6 | COC(=O)CCCCC=O.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CCCC2)cc1>>COC(=O)CCCCC=C1CCCC1 | O.COC(CCCCC=O)=O.[Br-].C1(CCCC1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Li]CCCC>>COC(CCCCC=C1CCCC1)=O | O=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | COC(=O)CCCCC=O.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CCCC2)cc1 | COC(=O)CCCCC=C1CCCC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | f1a9e9142e2fdc18994c8f2e1e4448d16b444db565878e90356478ddba8fbf7d | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | [CH]=C1CCCC1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[CH;D3;+0:8]-1-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[CH;D2;+0:1]=[C;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | 70 | [{"value": 70.0, "product": "COC(CCCCC=C1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "COC(CCCCC=C1CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a stirred suspension of cyclopentyltriphenylphosphonium bromide (10.0 g, 23.8 mmol) in TMF (60 mL) was added dropwise n-BuLi (10.2 mL, 2.5 M solution in hexanes, 23.8 mmol) at 0° C. under N2. The resulting solution was stirred at this temperature for 30 min and cooled to −78 ° C. A solution of 6-oxo-hexanoic acid me... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCC1 | C1CCCC1 | C1CCCC1 | HO- | C1CCOC1 | -78 | 0.5 | COC(=O)CCCCC=O.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CCCC2)cc1>C1CCOC1>COC(=O)CCCCC=C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1031d7c9f29c406cb2da0b969215688a | COC(=O)CCCCC=C1CCCC1>>OCCCCCC=C1CCCC1 | COC(CCCCC=C1CCCC1)=O.CC(C)C[AlH]CC(C)C>>C1(CCCC1)=CCCCCCO | CO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1 | COC(=O)CCCCC=C1CCCC1 | OCCCCCC=C1CCCC1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | [CH]=C1CCCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 104.1 | [{"value": 98.0, "product": "C1(CCCC1)=CCCCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.1, "product": "C1(CCCC1)=CCCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred solution of 6-cyclopentylidene-hexanoic acid methyl ester (2.77 g, 14.1 mmol) in toluene (130 mL) was added DIBAL-H (35.3 mL, 1 M solution in hexane, 35.3 mmol) dropwise at 0° C. under N2. After sting at 0° C. for 30 min, the reaction was quenched by MeOH (10 mL). Saturated aqueous sodium potassium tartrat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCCC1 | Other | C1(=CC=CC=C1)C | null | 0.5 | COC(=O)CCCCC=C1CCCC1>C1(=CC=CC=C1)C>OCCCCCC=C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7527adbc893f41bcbd88fd23ee6e45f9 | OCCCCCC=C1CCCC1>>OCCCCCCC1CCCC1 | C1(CCCC1)=CCCCCCO>>C1(CCCC1)CCCCCCO | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1 | OCCCCCC=C1CCCC1 | OCCCCCCC1CCCC1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 03e999f2f3e48f4d8a386c83154ab376ef372e868106b1956381812f45f9c4ae | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCC1 | [C:1]-[C:2]-[CH;D2;+0:3]=[C;H0;D3;+0:4]1-[C:5]-[C:6]-[C:7]-[C:8]-1>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 111.4 | [{"value": 100.0, "product": "C1(CCCC1)CCCCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 111.4, "product": "C1(CCCC1)CCCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-cyclopentylidene-hexan-1-ol (1.15 g, 6.85 mmol) in MeOH (50 mL) was hydrogenated with Pd—C (0.25 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclopentyl-hexan-1-ol (1.30 g, 100%) as a ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | [Pd].CO | null | null | OCCCCCC=C1CCCC1>[Pd].CO>OCCCCCCC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b709fb830664271a3d5e6c0dd5b37bc | O=C1CCC(=O)N1Br.OCCCCCCC1CCCC1>>BrCCCCCCC1CCCC1 | C1CC(=O)N(C1=O)Br.C1(CCCC1)CCCCCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCC1CCCC1 | O=C1CCC(=O)N1[Br:1].O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1 | O=C1CCC(=O)N1Br.OCCCCCCC1CCCC1 | BrCCCCCCC1CCCC1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | C1CCCC1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 94.1 | [{"value": 94.0, "product": "BrCCCCCCC1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.1, "product": "BrCCCCCCC1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 6-cyclopentyl-hexan-1-ol (1.20 g, 7.06 mmol) in DMF (20 mL) was added triphenylphosphine (2.08 g, 7.93 mmol). The solution was cooled to 0° C. and NBS (1.36 g, 7.64 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | C1CCCC1 | HO- | CN(C)C=O | 0 | 0.5 | O=C1CCC(=O)N1Br.OCCCCCCC1CCCC1>CN(C)C=O>BrCCCCCCC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-763f05fd4e2b412398aed036a2779493 | BrCCCCCCC1CCCC1.CN1CCC[C@H]1c1cccnc1>>Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCCC2)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCC1CCCC1>>Br.[Br-].C1(CCCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [Br:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][n:12][cH:24]1>>[BrH:1].[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][n+:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2... | BrCCCCCCC1CCCC1.CN1CCC[C@H]1c1cccnc1 | Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCCC2)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1cc([C@@H]2CCCN2)c[n+](CCCCCCC2CCCC2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[BrH;D0;+0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | 54.9 | [{"value": 54.0, "product": "Br.[Br-].C1(CCCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "Br.[Br-].C1(CCCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.43 g, 2.6 mmol) in AcOH (10 ml) was added (6-bromo-hexyl)-cyclopentane (1.50 g, 6.44 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-1-(6-cyclopentyl-hexyl)-3-(1-methyl-pyrrolidin-2-y... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1CC[NH]C1.C1=CC=[NH+]C=C1.C1CCCC1 | null | CC(=O)O | null | null | BrCCCCCCC1CCCC1.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCCC2)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9218e557d5c420fa426c304c9a5e1f0 | COC(=O)CCCCC=C1CCCCC1>>OCCCCCC=C1CCCCC1 | COC(CCCCC=C1CCCCC1)=O.CC(C)C[AlH]CC(C)C>>C1(CCCCC1)=CCCCCCO | CO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | COC(=O)CCCCC=C1CCCCC1 | OCCCCCC=C1CCCCC1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | [CH]=C1CCCCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 100.7 | [{"value": 100.0, "product": "C1(CCCCC1)=CCCCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.7, "product": "C1(CCCCC1)=CCCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a stired solution of 6-cyclohexylidene-hexanoic acid methyl ester (1.28 g, 6.10 mmol) in toluene (60 mL) was added DIBAL-H (15.3 mL, 1 M solution in hexane, 15.3 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (5 mL). Saturated aqueous sodium potassium tartrate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCCCC1 | Other | C1(=CC=CC=C1)C | 0 | 0.5 | COC(=O)CCCCC=C1CCCCC1>C1(=CC=CC=C1)C>OCCCCCC=C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ad26e7da6b343a29d1920b184022d66 | OCCCCCC=C1CCCCC1>>OCCCCCCC1CCCCC1 | C1(CCCCC1)=CCCCCCO>>C1(CCCCC1)CCCCCCO | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | OCCCCCC=C1CCCCC1 | OCCCCCCC1CCCCC1 | null | [Pd] | null | Reduction | Hydrogenation (double to single) | da8a9b0fabf153e7390d0529375b4e7b6b9340230ccf509d4c3ece1ac615e7d0 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCCC1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[C:5]-[C:6])-[C:7]-[C:8]>>[C:1]-[C:2]-[CH;D3;+0:3](-[CH2;D2;+0:4]-[C:5]-[C:6])-[C:7]-[C:8] | 96 | [{"value": 96.0, "product": "C1(CCCCC1)CCCCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.9, "product": "C1(CCCCC1)CCCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-cyclohexylidene-hexan-1-ol (1.05 g, 5.77 mmol) in MEOH (40 mL) was hydrogenated with Pd—C (0.23 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclohexyl-hexan-1-ol (1.02 g, 96%) as a col... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | null | [Pd] | null | null | OCCCCCC=C1CCCCC1>[Pd]>OCCCCCCC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fd0f2cc1e714086b7039b48ad25edc3 | O=C1CCC(=O)N1Br.OCCCCCCC1CCCCC1>>BrCCCCCCC1CCCCC1 | C1CC(=O)N(C1=O)Br.C1(CCCCC1)CCCCCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCC1CCCCC1 | O=C1CCC(=O)N1[Br:1].O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | O=C1CCC(=O)N1Br.OCCCCCCC1CCCCC1 | BrCCCCCCC1CCCCC1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | C1CCCCC1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 89 | [{"value": 89.0, "product": "BrCCCCCCC1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "BrCCCCCCC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 6-cyclohexyl-hexan-1-ol (0.98 g, 5.3 mmol) in DMF (15 mL) was added triphenylphosphine (1.56 g, 5.9 mmol). The solution was cooled to 0° C. and NBS (1.02 g, 5.7 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.6 mL). The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | C1CCCCC1 | HO- | CN(C)C=O | 0 | 0.5 | O=C1CCC(=O)N1Br.OCCCCCCC1CCCCC1>CN(C)C=O>BrCCCCCCC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cfc236aa65134edd94b1a22bfd257aac | BrCCCCCCC1CCCCC1.CN1CCC[C@H]1c1cccnc1>>Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCCCC2)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCC1CCCCC1>>Br.[Br-].C1(CCCCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [Br:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][n:12][cH:25]1>>[BrH:1].[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][n+:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]... | BrCCCCCCC1CCCCC1.CN1CCC[C@H]1c1cccnc1 | Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCCCC2)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1cc([C@@H]2CCCN2)c[n+](CCCCCCC2CCCCC2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[BrH;D0;+0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | 63.3 | [{"value": 63.0, "product": "Br.[Br-].C1(CCCCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "Br.[Br-].C1(CCCCC1)CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.31 g, 1.9 mmol) in AcOH (8 ml) was added (6-bromo-hexyl)-cyclohexane (1.15 g, 4.65 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-1-(6-cyclohexyl-hexyl)-3-(1-methyl-pyrrolidin-2-yl)-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1CC[NH]C1.C1=CC=[NH+]C=C1.C1CCCCC1 | null | CC(=O)O | null | null | BrCCCCCCC1CCCCC1.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CN1CCC[C@H]1c1ccc[n+](CCCCCCC2CCCCC2)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d45dd811ad1242be89b10cf1539f2c95 | CCCCC#CCCO.O=C1CCC(=O)N1Br>>CCCCC#CCCBr | C1CC(=O)N(C1=O)Br.C(CC#CCCCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCC#CCCCC | O[CH2:8][CH2:7][C:6]#[C:5][CH2:4][CH2:3][CH2:2][CH3:1].O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][Br:9] | CCCCC#CCCO.O=C1CCC(=O)N1Br | CCCCC#CCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:6]>>[Br;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5] | 71.4 | [{"value": 71.0, "product": "BrCCC#CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "BrCCC#CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of oct-3-yn-1-ol (1.26 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.2 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CCCCC#CCCO.O=C1CCC(=O)N1Br>CN(C)C=O>CCCCC#CCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a2e1c71b4a74113897194ff2892f23d | CCCCC#CCCBr.CN1CCC[C@H]1c1cccnc1>>CCCCC#CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCC#CCCCC>>[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCC#CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][Br:21].[n:9]1[cH:10][cH:11][cH:12][c:13]([C@@H:14]2[CH2:15][CH2:16][CH2:17][N:18]2[CH3:19])[cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][n+:9]1[cH:10][cH:11][cH:12][c:13]([C@@H:14]2[CH2:15][CH2:16][CH2:17][N:18]2[CH3:19])[cH:20]1.[Br-:21] | CCCCC#CCCBr.CN1CCC[C@H]1c1cccnc1 | CCCCC#CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]#[C:5]-[C:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[Br-;H0;D0:1].[C:6]-[C:5]#[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:8]:[c:7]):[c:10]:[c:11] | 56.9 | [{"value": 56.0, "product": "[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCC#CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.9, "product": "[Br-].CN1[C@@H](CCC1)C=1C=[N+](C=CC1)CCC#CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.41 g, 2.5 mmol) in AcOH (10 ml) was added 1-bromo-oct-3-yne (1.16 g, 6.14 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCCCC#CCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>CCCCC#CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f6ffb5c828b48f4b62716112b437464 | CCCCCCC#CCCO.O=C1CCC(=O)N1Br>>CCCCCCC#CCCBr | C1CC(=O)N(C1=O)Br.C(CC#CCCCCCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCC#CCCCCCC | O[CH2:10][CH2:9][C:8]#[C:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].O=C1CCC(=O)N1[Br:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][Br:11] | CCCCCCC#CCCO.O=C1CCC(=O)N1Br | CCCCCCC#CCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:6]>>[Br;H0;D1;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5] | 72.3 | [{"value": 72.0, "product": "BrCCC#CCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "BrCCC#CCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of dec-3-yn-1-ol (1.54 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.2 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CCCCCCC#CCCO.O=C1CCC(=O)N1Br>CN(C)C=O>CCCCCCC#CCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fdcf2a8f87f46b7a88d01e0c4bc8690 | CCCCCCC#CCCBr.CN1CCC[C@H]1c1cccnc1>>CCCCCCC#CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCC#CCCCCCC>>[Br-].C(CC#CCCCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][Br:23].[n:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3:21])[cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][n+:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3... | CCCCCCC#CCCBr.CN1CCC[C@H]1c1cccnc1 | CCCCCCC#CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]#[C:5]-[C:6].[c:7]:[c:8]:[n;H0;D2;+0:9]:[c:10]:[c:11]>>[Br-;H0;D0:1].[C:6]-[C:5]#[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:9](:[c:8]:[c:7]):[c:10]:[c:11] | 51.8 | [{"value": 51.0, "product": "[Br-].C(CC#CCCCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.8, "product": "[Br-].C(CC#CCCCCCC)[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.46 g, 2.8 mmol) in AcOH (15 ml) was added 1-bromo-dec-3-yne (1.50 g, 6.91 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCCCCCC#CCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>CCCCCCC#CCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-884fac516d964a66b91976598c93a77c | CC(C)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)CCCCC=O>>COC(=O)CCCCC=C(C)C | O.[Li]CCCC.[Br-].C(C)(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.COC(CCCCC=O)=O>>COC(CCCCC=C(C)C)=O | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:10]([CH3:11])[CH3:12])cc1.O=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12] | CC(C)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)CCCCC=O | COC(=O)CCCCC=C(C)C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | null | O=[CH;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[CH;D2;+0:1]=[C;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 101.1 | [{"value": 72.0, "product": "COC(CCCCC=C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.1, "product": "COC(CCCCC=C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a stirred suspension of isopropyltriphenylphosphonium bromide (10.9 g, 28.3 mmol) in THF (60 mL) was added dropwise n-BuLi (12.0 mL, 2.5 M solution in hexanes, 30.0 mmol) at 0° C. under N2. The resulting solution was stirred at this temperature for 30 min and cooled to −78° C. A solution of 6-oxo-hexanoic acid methy... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C1CCOC1 | -78 | 0.5 | CC(C)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)CCCCC=O>C1CCOC1>COC(=O)CCCCC=C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d7be9b2d98a4dcd85a633f7f75d4960 | COC(=O)CCCCC=C(C)C>>CC(C)=CCCCCCO | COC(CCCCC=C(C)C)=O.CC(C)C[AlH]CC(C)C>>CC(=CCCCCCO)C | CO[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])=[O:10]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10] | COC(=O)CCCCC=C(C)C | CC(C)=CCCCCCO | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 98 | [{"value": 98.0, "product": "CC(=CCCCCCO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "CC(=CCCCCCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 7-methyl-oct-6-enoic acid methyl ester (3.29 g, 19.4 mmol) in toluene (180 mL) was added DIBAL-H (48.5 mL, 1 M solution in hexane, 48.5 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (12 mL). Saturated aqueous sodium potassium tartrate (1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | Other | C1(=CC=CC=C1)C | 0 | 0.5 | COC(=O)CCCCC=C(C)C>C1(=CC=CC=C1)C>CC(C)=CCCCCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4efa8e1d496e47bc9bee39c2247c28bd | CC(C)=CCCCCCO.O=C1CCC(=O)N1Br>>CC(C)=CCCCCCBr | C1CC(=O)N(C1=O)Br.CC(=CCCCCCO)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCC=C(C)C | O[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3].O=C1CCC(=O)N1[Br:10]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10] | CC(C)=CCCCCCO.O=C1CCC(=O)N1Br | CC(C)=CCCCCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 77 | [{"value": 77.0, "product": "BrCCCCCC=C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "BrCCCCCC=C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 7-methyl-oct-6-en-1-ol (1.00 g, 7.04 mmol) in DMF (18 mL) was added triphenylphosphine (2.06 g, 7.85 mmol). The solution was cooled to 0° C. and NBS (1.35 g, 7.58 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CC(C)=CCCCCCO.O=C1CCC(=O)N1Br>CN(C)C=O>CC(C)=CCCCCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f398a8f4e7347fcb95044dd74345579 | CC(C)=CCCCCCBr.CN1CCC[C@H]1c1cccnc1>>Br.CC(C)=CCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCC=C(C)C>>Br.[Br-].CC(=CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C)C | [Br:1][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[C:3]([CH3:2])[CH3:4].[n:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3:21])[cH:22]1>>[BrH:1].[CH3:2][C:3]([CH3:4])=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n+:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3:... | CC(C)=CCCCCCBr.CN1CCC[C@H]1c1cccnc1 | Br.CC(C)=CCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[BrH;D0;+0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | To a stired solution of (S)-nicotine (0.33 g, 2.0 mmol) in AcOH (10 ml) was added 8-bromo-2-methyl-oct-2-ene (1.05 g, 5.12 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to (S)-1-(7-methyl-oct-6-enyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CC(C)=CCCCCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CC(C)=CCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed23eba753104b989acd5556d6c144e0 | CC(C)=CCCCCCO>>CC(C)CCCCCCO | CC(=CCCCCCO)C>>CC(CCCCCCO)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10] | CC(C)=CCCCCCO | CC(C)CCCCCCO | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | [C:1]-[C:2]-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6] | 96 | [{"value": 96.0, "product": "CC(CCCCCCO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "CC(CCCCCCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-methyl-oct-6-en-1-ol (1.42 g, 10.0 mmol) in MeOH (70 mL) was hydrogenated with Pd—C (0.40 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 7-methyl-octan-1-ol (1.38 g, 96%) as a colorless oil... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | [Pd].CO | null | null | CC(C)=CCCCCCO>[Pd].CO>CC(C)CCCCCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1dcf53a9a79d4a13b5884fe5d9b1212b | CC(C)CCCCCCO.O=C1CCC(=O)N1Br>>CC(C)CCCCCCBr | C1CC(=O)N(C1=O)Br.CC(CCCCCCO)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCCCCCC(C)C | O[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3].O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10] | CC(C)CCCCCCO.O=C1CCC(=O)N1Br | CC(C)CCCCCCBr | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | null | O-[CH2;D2;+0:1]-[C:2]-[C:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:1]-[C:2]-[C:3] | 74.2 | [{"value": 74.0, "product": "BrCCCCCCC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.2, "product": "BrCCCCCCC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 7-methyl-octan-1-ol (1.20 g, 8.33 mmol) in DMF (20 mL) was added triphenylphosphine (2.43 g, 9.26 mmol). The solution was cooled to 0° C. and NBS (1.60 g, 8.99 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was di... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | null | HO- | CN(C)C=O | 0 | 0.5 | CC(C)CCCCCCO.O=C1CCC(=O)N1Br>CN(C)C=O>CC(C)CCCCCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1fe6ce655e6c48aab8e8d39e3535dc10 | CC(C)CCCCCCBr.CN1CCC[C@H]1c1cccnc1>>Br.CC(C)CCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCCCCCC(C)C>>Br.[Br-].CC(CCCCCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C)C | [Br:1][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:3]([CH3:2])[CH3:4].[n:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH3:21])[cH:22]1>>[BrH:1].[CH3:2][CH:3]([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n+:11]1[cH:12][cH:13][cH:14][c:15]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]2[CH... | CC(C)CCCCCCBr.CN1CCC[C@H]1c1cccnc1 | Br.CC(C)CCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[BrH;D0;+0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | To a stirred solution of (S)-nicotine (0.37 g, 2.3 mmol) in AcOH (10 ml) was added 1-bromo-7-methyl-octane (1.20 g, 5.80 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to (S)-1-(7-methyl-octyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CC(C)CCCCCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>Br.CC(C)CCCCCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-830166ec73f84d72856962a7dc3cd600 | CCOCCOCCBr.CN1CCC[C@H]1c1cccnc1>>CCOCCOCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | N1=CC=CC(=C1)[C@H]1N(C)CCC1.BrCCOCCOCC>>[Br-].C(C)OCCOCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][Br:21].[n:9]1[cH:10][cH:11][cH:12][c:13]([C@@H:14]2[CH2:15][CH2:16][CH2:17][N:18]2[CH3:19])[cH:20]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][n+:9]1[cH:10][cH:11][cH:12][c:13]([C@@H:14]2[CH2:15][CH2:16][CH2:17][N:18]2[CH3:19])[cH:20]1.[Br-:21] | CCOCCOCCBr.CN1CCC[C@H]1c1cccnc1 | CCOCCOCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1c[nH+]cc([C@@H]2CCCN2)c1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9].[Br-;H0;D0:4] | 38 | [{"value": 38.0, "product": "[Br-].C(C)OCCOCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.0, "product": "[Br-].C(C)OCCOCC[N+]1=CC(=CC=C1)[C@H]1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of (S)-nicotine (0.67 g, 4.1 mmol) in AcOH (20 ml) was added 1-bromo-2-(2-ethoxy-ethoxy)-ethane (1.97 g, 10.0 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine succes... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1CC[NH]C1 | null | CC(=O)O | null | null | CCOCCOCCBr.CN1CCC[C@H]1c1cccnc1>CC(=O)O>CCOCCOCC[n+]1cccc([C@@H]2CCCN2C)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3dcb0f7ea6c24452b94fb26d65c2fe19 | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | O.C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C2=CC=CC=C2C1)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][cH:23]1)[N:13]1[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH... | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 82.2 | [{"value": 82.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C2=CC=CC=C2C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.2, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C2=CC=CC=C2C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (15.0 g, 42.7 mmol) and N,N′-carbonyldiimidazole (7.27 g, 44.8 mmol) in tetrahydrofuran (50 mL) under nitrogen was stirred at room temperature for 2 hours. To the resulting solution was added hydroxylamine hydrochloride (3.86 g, 55.5 mmol). T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | 2 | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc860f8e8ab649108b5b56d9f4f04be3 | CCOc1cc(C(N)CC(=O)O)ccc1OC.Cc1ccc2c(c1)C(=O)OC2=O>>CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC | NC(CC(=O)O)C1=CC(=C(C=C1)OC)OCC.CC=1C=C2C(C(=O)OC2=O)=CC1.C(C)(=O)OCC.CCCCCC>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC(=CC2)C)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[NH2:12])[cH:24][cH:25][c:26]1[O:27][CH3:28].O1[C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][c:21]2[C:22]1=[O:23]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[N:12]2[C:13](=[O:14])[c:15]3[cH:16][cH:17][c... | CCOc1cc(C(N)CC(=O)O)ccc1OC.Cc1ccc2c(c1)C(=O)OC2=O | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC | null | null | O.C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [NH2;D1;+0:1]-[C:2](-[c:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]-1:[c:15]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[C:4]-[C:2](-[c:3])-[N;H0;D3;+0:1]1-[C;H0;D3;+0:9](=[O;D1;H0:8])-[c:14](:[c:15]):[c:12](:[c:13])-[C;H0;D3;+0:10]-1=[O;D1;H0:11] | 71 | [{"value": 71.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC(=CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC(=CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 3-amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (3.00 g, 12.5 mmol) and 4-methylphthalic anhydride (2.13 g, 12.5 mmol, 95%) in acetic acid was heated to reflux under nitrogen for 18 hours. The mixture was allowed to cool to room temperature. The solvent was removed in vacuo to give an oil. The ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O.C(C)(=O)O | null | null | CCOc1cc(C(N)CC(=O)O)ccc1OC.Cc1ccc2c(c1)C(=O)OC2=O>O.C(C)(=O)O>CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-970e6417d85d44578213aa5f09be0a14 | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC(=CC2)C)=O.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC(=CC2)C)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][cH:25]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([CH3:20])[cH:21][c:22]2[C:23]1=[O:24])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 88 | [{"value": 88.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC(=CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC(=CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(4-methylphthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(4-methyl-phthalimido)propanoic acid (2.40 g, 6.26 mmol), N,N′-carbonyldiimidazole (1.12 g, 6.91 mmol) and hydroxylamine hydrochloride (530 mg, 7.62 mmol) in tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24545113e7804aafa73858663504a85f | CCOC(=O)N1C(=O)c2ccccc2C1=O.COc1ccc(C(N)CC(=O)O)cc1OC1CCCC1>>COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | NC(CC(=O)O)C1=CC(=C(C=C1)OC)OC1CCCC1.C([O-])([O-])=O.[Na+].[Na+].C(C)OC(=O)N1C(C=2C(C1=O)=CC=CC2)=O>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O | CCOC(=O)N1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[NH2:12])[cH:23][c:24]1[O:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[N:12]2[C:13](=[O:14])... | CCOC(=O)N1C(=O)c2ccccc2C1=O.COc1ccc(C(N)CC(=O)O)cc1OC1CCCC1 | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | null | null | O.C(C)#N | Acylation | OtherReaction | dee4319fb5c05073dfe09fdcfc315b1d79c0b2e71d9dcd2bec537ad3e531713e | bd8b586242504a7a0d63516550627e0a235acd769462fa1476e6d9c6d91ef2e8 | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | C-C-O-C(=O)-N1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6])-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[NH2;D1;+0:9]-[C:10](-[c:11])-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[O;D1;H0:14]=[C:13](-[O;D1;H1:15])-[C:12]-[C:10](-[c:11])-[N;H0;D3;+0:9]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6])-[C;H0;D3;+0:7]-... | 68 | [{"value": 68.0, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-amino-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (3.00 g, 10.8 mmol) and sodium carbonate (1.20 g, 11.3 mmol) in acetonitrile (30 mL) and water (30 mL) under nitrogen was stirred at room temperature for 15 minutes. To the resulting solution was added N-ethoxycarbonyl phthalimide (2.36 g, 10.8 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Substituted dicarboximide.Primary amine | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | O.C(C)#N | null | 0.25 | CCOC(=O)N1C(=O)c2ccccc2C1=O.COc1ccc(C(N)CC(=O)O)cc1OC1CCCC1>O.C(C)#N>COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-073391753dcd4781ab7c7973ddf89a94 | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1.NO>>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O.Cl.NO>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[cH:24]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=... | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1.NO | COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 93.1 | [{"value": 93.0, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Cyclopentyloxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid (1.50 g, 3.67 mmol), N,N′-carbonyldiimidazole (653 mg, 4.03 mmol) and hydroxylamine hydrochloride (308 mg, 4.43 mmol) in tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | O1CCCC1 | null | null | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1.NO>O1CCCC1>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-926f807c397b47dfbafbccccb921a8df | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.CNO.O=C(n1ccnc1)n1ccnc1>>CCOc1cc(C(CC(=O)N(C)O)N2Cc3ccccc3C2=O)ccc1OC.CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.CNO>>ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O.ON(C(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:13])[N:14]2[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[C:22]2=[O:23])[cH:24][cH:25][c:26]1[O:27][CH3:28].[NH:39]([OH:40])[CH3:55].n1[cH:43][cH:42][n:41]([C:35](n2[cH:32][n:11][cH:12][cH:44]2)=[O:31])[cH:49]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6... | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.CNO.O=C(n1ccnc1)n1ccnc1 | CCOc1cc(C(CC(=O)N(C)O)N2Cc3ccccc3C2=O)ccc1OC.CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | f4592d64c00ed31ac9c18840ec71eb36951ee67e7bbf90b0864f860f09befbbb | c3de5cd3f492b712cc166a1880687e5d41a03f0c6ab91da832b6b1edc4ef3d58 | O=C1c2ccccc2CN1Cc1ccccc1.O=C1c2ccccc2CN1Cc1ccccc1 | [CH3;D1;+0:1]-[NH;D2;+0:2]-[O;D1;H1:3].[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[OH;D1;+0:8].[O;H0;D1;+0:9]=[C;H0;D3;+0:10](-[n;H0;D3;+0:11]1:[cH;D2;+0:12]:[cH;D2;+0:13]:n:[cH;D2;+0:14]:1)-n1:[cH;D2;+0:15]:[n;H0;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C;D1;H3:19]-[C:20]-[O;H0;D2;+0:9]-[c;H0;D3;+0:15]1:[c:21]:[c:22](-... | 120.8 | [{"value": 61.0, "product": "ON(C(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 120.8, "product": "ON(C(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Hydroxy-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (1.0 g, 2.8 mmol), carbonyldiimidazole (500 mg, 3.1 mmol) and N-methyl-hydroxylamine hydrochloride (300 mg, 3.5 mmol) in tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Ether.Ether.Secondary amide.Tertiary amide.Tertiary amide | c1c[nH]cn1.c1c[nH]cn1 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccc2c(c1)C[NH]C2 | null | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.CNO.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCOc1cc(C(CC(=O)N(C)O)N2Cc3ccccc3C2=O)ccc1OC.CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1c963156178450983f9ad8624a6b24d | CCOc1cc(C(N)CC(=O)O)ccc1OC.O=C1OC(=O)c2cc3ccccc3cc21>>CCOc1cc(C(CC(=O)O)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC | NC(CC(=O)O)C1=CC(=C(C=C1)OC)OCC.C1=C2C(=CC3=CC=CC=C13)C(=O)OC2=O>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[NH2:12])[cH:27][cH:28][c:29]1[O:30][CH3:31].O1[C:13](=[O:14])[c:15]2[cH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[cH:23][c:24]2[C:25]1=[O:26]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:11])[N:12]2[C:13](=[O:14])[c:1... | CCOc1cc(C(N)CC(=O)O)ccc1OC.O=C1OC(=O)c2cc3ccccc3cc21 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC | null | null | C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | f9f1bcb147a5cf27edd8abfab2e29b7000b0c24cce3f491ccd375f7fa360842b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2cc3ccccc3cc2C(=O)N1Cc1ccccc1 | [NH2;D1;+0:1]-[C:2](-[c:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]-1:[c:15]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[C:4]-[C:2](-[c:3])-[N;H0;D3;+0:1]1-[C;H0;D3;+0:9](=[O;D1;H0:8])-[c:14](:[c:15]):[c:12](:[c:13])-[C;H0;D3;+0:10]-1=[O;D1;H0:11] | 93.5 | [{"value": 93.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.5, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]isoindol-2-yl)-propanoic acid was prepared according to Example 2A from 3-amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (3.00 g, 12.5 mmol), 2,3-napthalene dicarboxylic anhydride (2.59 g, 12.5 mmol) in acetic acid (20 mL) to afford 3-(3-ethoxy-4-methox... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2cc3c(cc2c1)COC3 | c1ccc2cc3c(cc2c1)C[NH]C3 | c1ccccc1.c1ccc2cc3c(cc2c1)C[NH]C3 | HO- | C(C)(=O)O | null | null | CCOc1cc(C(N)CC(=O)O)ccc1OC.O=C1OC(=O)c2cc3ccccc3cc21>C(C)(=O)O>CCOc1cc(C(CC(=O)O)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6243a1e6925a455386d019f4641f100f | CCOc1cc(C(CC(=O)O)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[cH:24][c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:1... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2cc3ccccc3cc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 77.2 | [{"value": 77.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C=C3C(=CC2C1=O)C=CC=C3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]-isoindol-2-yl)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]isoindol-2-yl)propanoic acid (2.00 g, 4.77 mmol), N,N′-carbonyldiimidazole (889 mg, 5.48 mmol) and hydro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2cc3c(cc2c1)C[NH]C3 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ed65af14c334ce9a46a8ca839a30133 | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC>>CCOc1cc(C(CC(=O)NOC)N2Cc3ccccc3C2=O)ccc1OC | CN1CCCCC1.C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.CCOCC>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NOC)N1C(C2=CC=CC=C2C1)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][cH:24]1)[N:14]1[CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23])=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][O:12][CH3:13])[N:14]2[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21... | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC | CCOc1cc(C(CC(=O)NOC)N2Cc3ccccc3C2=O)ccc1OC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 60577a71c8e467034449e13d5ea72c2db8cfd5cc985a5e7caa0754cf14701cd5 | 8805aa8a6f462f0d89c6a6bcd4c045ef9dc917b34f6983d2626d92f6d7b6bf7c | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]>>[#8:5]-[#7:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 67 | [{"value": 67.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NOC)N1C(C2=CC=CC=C2C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (500 mg, 1.41 mmol) and N,N′-carbonyldiimidazole (250 mg, 1.54 mmol) in methylene chloride (30 mL) under nitrogen was stirred at room temperature for 30 minutes. To the solution was added 0-methyl hydroxylamine hydrochloride (175 mg, 2.09 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | null | C(Cl)Cl | null | 0.5 | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC>C(Cl)Cl>CCOc1cc(C(CC(=O)NOC)N2Cc3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90ed20b31c314f3fabedb1f30390738f | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NOCc1ccccc1>>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O.Cl.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32][cH:31]1)[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]1=[O:30])=[O:10].[NH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NOCc1ccccc1 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC(c1ccccc1)N1C(=O)c2ccccc2C1=O)NOCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 94 | [{"value": 94.0, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.8, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-phthalimido-propanoic acid (869 mg, 2.36 mmol), N,N′-carbonyldiimidazole (410 mg, 2.53 mmol) and O-benzylhydroxylamine hydrochloride (444 mg, 2.78 mmol) in tetrahydrofuran (6... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NOCc1ccccc1>O1CCCC1>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ce5d7100d314c03beea022c021460a4 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC.NOCc1ccccc1>>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O.Cl.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35][cH:34]1)[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[c:31]2[C:32]1=[O:33])=[O:10].[NH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC.NOCc1ccccc1 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC(c1ccccc1)N1C(=O)c2ccccc2C1=O)NOCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)propanoic acid (1.30 g, 3.14 mmol), N,N′-carbonyldiimidazole (533 mg, 3.28 mmol) and O-benzylhydroxylamine hydrochloride (550 mg, 3.45 mmol) in t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC.NOCc1ccccc1>O1CCCC1>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abe0a0cc4d6d4af3ab05d2a1afad5be1 | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NOCc1ccccc1>>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2Cc3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.Cl.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31][cH:30]1)[N:20]1[CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]1=[O:29])=[O:10].[NH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][O:1... | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NOCc1ccccc1 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2Cc3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC(c1ccccc1)N1Cc2ccccc2C1=O)NOCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 75.1 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (1.78 g, 5.00 mmol), N,N′-carbonyldiimidazole (850 mg, 5.24 mmol) and O-benzylhydroxylamine hydrochloride (940 mg, 5.89 mmol) in tet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NOCc1ccccc1>O1CCCC1>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2Cc3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6cba90fa83d14687a3ec6c53ce25f1fd | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][cH:24]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[cH:17][cH... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 77 | [{"value": 77.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.8, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-phthalimidopropanoic acid (1.00 g, 2.71 mmol), N,N′-carbonyldiimidazole (461 mg, 2.84 mmol) and hydroxylamine hydrochloride (208 mg, 2.99 mmol) in tetrahydrofuran (6 mL) to aff... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66da087430004165808bba7fc1ca6188 | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC.NO>>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC | COC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O.Cl.NO>>ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[cH:17][cH:18][cH:1... | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC.NO | COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 80.2 | [{"value": 80.0, "product": "ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Hydroxy-3-(3,4-dimethoxyphenyl)-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-(3,4-dimethoxyphenyl)-3-phthalimidopropanoic acid (1.82 g, 5.12 mmol), N,N′-carbonyldiimidazole (870 mg, 5.39 mmol) and hydroxylamine hydrochloride (391 mg, 5.63 mmol) in tetrahydrofuran (8 mL) to afford N-hydr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC.NO>O1CCCC1>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79739ccae09f47ad8b2007ebcb742756 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][cH:27]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[c:24]2[C:25]1=[O:26])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 77 | [{"value": 77.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.8, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4methoxyphenyl)-N-hydroxy-3-(3-nitrophthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)propanoic acid (3.64 g, 8.86 mmol), N,N′-carbonyldiimidazole (1.50 g, 9.25 mmol) and hydroxylamine hydrochloride (672 mg, 9.67 mmol) in tetrahydrofu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1e63243c4814197b9a17347d5a3368b | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC(C)C.NO>>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC(C)C | CC(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OC(C)C)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH:27]([CH3:28])[CH3:29])[cH:24]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[c... | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC(C)C.NO | COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC(C)C | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 68.5 | [{"value": 68.0, "product": "ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "ONC(CC(N1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)OC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Hydroxy-3-{3-(2-propoxy)-4-methoxyphenyl}-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-{3-(2-propoxy)-4-methoxyphenyl}-3-phthalimidopropanoic acid (2.0 g, 5.2 mmol), carbonyldiimidazole (1.02 g, 6.29 mmol), and hydroxylamine hydrochloride (481 mg, 6.92 mmol) in tetrahydrofuran (10 mL) t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC(C)C.NO>O1CCCC1>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccccc3C2=O)cc1OC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d250504239546bd8125a5af3702c54d | CCOc1cc(C(CC(=O)O)N2C(=O)c3c(F)ccc(F)c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3c(F)ccc(F)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2F)F)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2F)F)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][cH:26]1)[N:13]1[C:14](=[O:15])[c:16]2[c:17]([F:18])[cH:19][cH:20][c:21]([F:22])[c:23]2[C:24]1=[O:25])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:... | CCOc1cc(C(CC(=O)O)N2C(=O)c3c(F)ccc(F)c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3c(F)ccc(F)c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 57 | [{"value": 57.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.6, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-3-(3,6-difluorophthalimido)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3,6-difluorophthalimido)propanoic acid (580 mg, 1.43 mmol), carbonyldiimidazole (255 mg, 1.57 mmol) and hydroxylamine hydrochloride (120 mg, 1.73 mmol) in tetrah... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3c(F)ccc(F)c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3c(F)ccc(F)c3C2=O)ccc1OC |
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