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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-311e46e924e444df924ddcbbce7004ba | COc1cc(C(O)c2ccccc2F)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccccc2F)ccc1OCc1ccccc1 | [Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1.C(C1=CC=CC=C1)OC1=C(C=C(C(C2=C(C=CC=C2)F)O)C=C1)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C(=O)C2=C(C=CC=C2)F)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH... | COc1cc(C(O)c2ccccc2F)ccc1OCc1ccccc1 | COc1cc(C(=O)c2ccccc2F)ccc1OCc1ccccc1 | null | null | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1ccc(OCc2ccccc2)cc1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 3 | HOUR | 69.8 g of 4-(benzyloxy)-2'-fluoro-3-methoxybenzhydrol (dissolved in 600 ml of methylene chloride) are treated within 30 minutes at 20° with 45.3 g of pyridinium chlorochromate and stirred at 20° for 3 hours. The precipitate formed is subsequently filtered and washed with methylene chloride. The filtrate is evaporated a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | 3 | COc1cc(C(O)c2ccccc2F)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccccc2F)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a0b6669d0ef14f60878fe0cc42ec141a | COc1cc(C(=O)c2ccccc2F)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccccc2F)ccc1O | Br.C(C1=CC=CC=C1)OC1=C(C=C(C(=O)C2=C(C=CC=C2)F)C=C1)OC>>FC1=C(C=CC=C1)C(C1=CC(=C(C=C1)O)OC)=O | c1ccc(C[O:18][c:17]2[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[F:14])[cH:15][cH:16]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15][cH:16][c:17]1[OH:18] | COc1cc(C(=O)c2ccccc2F)ccc1OCc1ccccc1 | COc1cc(C(=O)c2ccccc2F)ccc1O | null | null | C(C)(=O)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 1.5 | HOUR | 170 ml of 33 percent hydrobromic acid in glacial acetic acid are added at 20°-25° within 20 minutes to 42.4 g of 4-(benzyloxy)-2'-fluoro-3-methoxybenzophenone (dissolved in 450 ml of methylene chloride). After stirring at 20° for 1.5 hours, the reaction mixture is poured into 750 ml of ice-water; the methylene chloride... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O | null | 1.5 | COc1cc(C(=O)c2ccccc2F)ccc1OCc1ccccc1>C(C)(=O)O>COc1cc(C(=O)c2ccccc2F)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-44336f450f774728b453f11af0e91f07 | COc1cc(C(=O)c2ccccc2F)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2ccccc2F)cc([N+](=O)[O-])c1O | [N+](=O)(O)[O-].FC1=C(C=CC=C1)C(C1=CC(=C(C=C1)O)OC)=O>>FC1=C(C=CC=C1)C(C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15][cH:16][c:20]1[OH:21].O[N+:17](=[O:18])[O-:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]1[OH:21] | COc1cc(C(=O)c2ccccc2F)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)c2ccccc2F)cc([N+](=O)[O-])c1O | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C(c1ccccc1)c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 1.5 | HOUR | 7.8 ml of 65 percent nitric acid are added dropwise at 20° within 20 minutes to 29.4 g of 2'-fluoro-4-hydroxy-3-methoxybenzophenone (dissolved in 450 ml of acetic acid). After stirring for 1.5 hours, the reaction mixture is poured into 2 l of ice-water and the precipitate formed is filtered off, washed with water and d... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | 1.5 | COc1cc(C(=O)c2ccccc2F)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2ccccc2F)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-de5a925d6e474d548e5d51dfa8edebcc | NC(=S)NCCc1ccccc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.O=[N+]([O-])c1cc(-c2csc(NCCc3ccccc3)n2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.C(CC1=CC=CC=C1)NC(=S)N>>Br.[N+](=O)([O-])C1=C(C(O)=CC(=C1)C=1N=C(SC1)NCCC1=CC=CC=C1)O | [S:10]=[C:11]([NH:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH2:21].O=[C:8]([c:7]1[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:25]([OH:26])[c:23]([OH:24])[cH:22]1)[CH2:9][Br:1]>>[BrH:1].[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][s:10][c:11]([NH:12][CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19... | NC(=S)NCCc1ccccc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.O=[N+]([O-])c1cc(-c2csc(NCCc3ccccc3)n2)cc(O)c1O | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(CCNc2nc(-c3ccccc3)cs2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C:9]-[#7:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[S;H0;D1;+0:13]>>[BrH;D0;+0:3].[C:9]-[#7:10]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:2]:[s;H0;D2;+0:13]:1 | null | [] | null | null | null | null | A suspension of 13.8 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 9.0 g of 1-(phenethyl)-2-thiourea in 150 ml of n-butanol and the mixture is heated to boiling under reflux for 3 hours. After cooling to room temperature, the crystals are filtered under suction and crystallized from n-butanol. There... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccccc1 | HO- | C(CCC)O | null | null | NC(=S)NCCc1ccccc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(CCC)O>Br.O=[N+]([O-])c1cc(-c2csc(NCCc3ccccc3)n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4d95d8063f6240228a4e9c125dc2970a | NC(=S)NC12CC3CC(CC(C3)C1)C2.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.O=[N+]([O-])c1cc(-c2cnc(NC34CC5CC(CC(C5)C3)C4)s2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.C12(CC3CC(CC(C1)C3)C2)NC(=S)N>>Br.C12(CC3CC(CC(C1)C3)C2)NC=2SC(=CN2)C2=CC(=C(C(O)=C2)O)[N+](=O)[O-] | [NH2:10][C:11]([NH:12][C:13]12[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:20]3)[CH2:21]1)[CH2:22]2)=[S:23].O=[C:8]([c:7]1[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:27]([OH:28])[c:25]([OH:26])[cH:24]1)[CH2:9][Br:1]>>[BrH:1].[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][n:10][c:11]([NH:12][C:13]34[CH2:14][CH:15]5... | NC(=S)NC12CC3CC(CC(C3)C1)C2.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.O=[N+]([O-])c1cc(-c2cnc(NC34CC5CC(CC(C5)C3)C4)s2)cc(O)c1O | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(-c2cnc(NC34CC5CC(CC(C5)C3)C4)s2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C:9]-[#7:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[S;H0;D1;+0:13]>>[BrH;D0;+0:3].[C:9]-[#7:10]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[s;H0;D2;+0:13]:1 | null | [] | null | null | null | null | A suspension of 8.3 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 1-(1-adamantyl)-2-thiourea in 90 ml of n-butanol and the mixture is heated to boiling under reflux for 4 hours. After cooling to room temperature, the crystals are filtered under suction and recrystallized from n-butanol. There is obt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1cscn1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HO- | C(CCC)O | null | null | NC(=S)NC12CC3CC(CC(C3)C1)C2.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(CCC)O>Br.O=[N+]([O-])c1cc(-c2cnc(NC34CC5CC(CC(C5)C3)C4)s2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e4e15c3ce7554449852d2801074d3ecb | CC(=O)OCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=C(CO)c1cc(O)c(O)c([N+](=O)[O-])c1 | C(C)(=O)OCC(C1=CC(=C(C(=C1)[N+](=O)[O-])O)O)=O>>OCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | CC(=O)[O:4][CH2:3][C:2](=[O:1])[c:5]1[cH:6][c:7]([OH:8])[c:9]([OH:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1>>[O:1]=[C:2]([CH2:3][OH:4])[c:5]1[cH:6][c:7]([OH:8])[c:9]([OH:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | CC(=O)OCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=C(CO)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | Cl.C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[O;D1;H0:4]=[C:3](-[c:5])-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | A suspension of 2.6 g of (3,4-dihydroxy-5-nitrobenzoyl)methyl acetate in 20 ml of ethanol and 20 ml of 1N hydrochloric acid is heated to boiling under reflux for 5 hours. The reaction mixture is then evaporated, the residue is distilled with toluene and then recrystallized from ethanol. There is obtained 2,3',4'-trihyd... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | Cl.C(C)O | null | null | CC(=O)OCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1>Cl.C(C)O>O=C(CO)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ca95057036464fb2a555c89433f5e408 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.N#C/C(N)=C(/N)C#N>>N#Cc1nc(O)c(-c2cc(O)c(O)c([N+](=O)[O-])c2)nc1C#N | OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C(=O)OCCCCCC)=O.N/C(=C(/C#N)\N)/C#N>>OC1=C(N=C(C(=N1)C#N)C#N)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | CCCCCCO[C:5](=[O:6])[C:7](=O)[c:8]1[cH:9][c:10]([OH:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1.[N:1]#[C:2]/[C:3]([NH2:4])=[C:20](/[NH2:19])[C:21]#[N:22]>>[N:1]#[C:2][c:3]1[n:4][c:5]([OH:6])[c:7](-[c:8]2[cH:9][c:10]([OH:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]2)[n:19][c:20]1[C:21]#[N:22] | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.N#C/C(N)=C(/N)C#N | N#Cc1nc(O)c(-c2cc(O)c(O)c([N+](=O)[O-])c2)nc1C#N | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | b9cc8aadffc394af5d830908307996f03955b4d8cc7045f4b42af3988f24d3a7 | e1dd4674d59a7a9788bb2a36dcd479ddd279bc27e880caff550f05806685f20c | c1ccc(-c2cnccn2)cc1 | C-C-C-C-C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[N;D1;H0:9]#[C:10]/[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[C;H0;D3;+0:13](/[NH2;D1;+0:14])-[C:15]#[N;D1;H0:16]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:3](-[c;H0;D3;+... | null | [] | null | null | null | null | A solution of 4.0 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 1.5 g of diaminomaleonitrile in 35 ml of ethanol is heated to boiling under reflux for 24 hours. The alcohol is then distilled, the residue is dissolved in ether, washed with water, dried over sodium sulfate, filtered and evaporated. There is obta... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ketone.Ester | Aromatic alcohol | null | c1cnccn1 | c1cnccn1.c1ccccc1 | HO- | C(C)O | null | null | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.N#C/C(N)=C(/N)C#N>C(C)O>N#Cc1nc(O)c(-c2cc(O)c(O)c([N+](=O)[O-])c2)nc1C#N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fd31337ad3a24725a4de49e2d018ed9f | COc1cc(C(=O)CBr)cc(C#N)c1OC>>N#Cc1cc(C(=O)CBr)cc(O)c1O | BrCC(=O)C=1C=C(C(=C(C#N)C1)OC)OC.B(Br)(Br)Br.C(O)([O-])=O.[Na+].C(C)(=O)O>>BrCC(=O)C=1C=C(C(=C(C#N)C1)O)O | C[O:12][c:11]1[cH:10][c:5]([C:6](=[O:7])[CH2:8][Br:9])[cH:4][c:3]([C:2]#[N:1])[c:13]1[O:14]C>>[N:1]#[C:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][Br:9])[cH:10][c:11]([OH:12])[c:13]1[OH:14] | COc1cc(C(=O)CBr)cc(C#N)c1OC | N#Cc1cc(C(=O)CBr)cc(O)c1O | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 18 | HOUR | 4.2 g of 5-(bromoacetyl)-2,3-dimethoxybenzonitrile dissolved in 150 ml of methylene chloride are treated with 8.9 ml of boron tribromide. The reaction mixture is stirred at 20° for 18 hours. It is subsequently poured into 220 ml of saturated sodium hydrogen carbonate solution and 100 g of ice, adjusted to pH 6 with gla... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 18 | COc1cc(C(=O)CBr)cc(C#N)c1OC>C(Cl)Cl>N#Cc1cc(C(=O)CBr)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-21b99671dadd41de8b36e62c0a1d232f | N#Cc1cc(C(=O)CBr)cc(O)c1O.NC(=S)Nc1ccccc1>>N#Cc1cc(-c2csc(Nc3ccccc3)n2)cc(O)c1O | BrCC(=O)C=1C=C(C(=C(C#N)C1)O)O.C1(=CC=CC=C1)NC(=S)N.Cl>>Cl.N(C1=CC=CC=C1)C=1SC=C(N1)C=1C=C(C(=C(C#N)C1)O)O | O=[C:7]([c:6]1[cH:5][c:4]([C:3]#[N:2])[c:22]([OH:23])[c:20]([OH:21])[cH:19]1)[CH2:8]Br.[S:9]=[C:10]([NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[NH2:18]>>[N:2]#[C:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18]2)[cH:19][c:20]([OH:21])[c:22]1[OH:23] | N#Cc1cc(C(=O)CBr)cc(O)c1O.NC(=S)Nc1ccccc1 | N#Cc1cc(-c2csc(Nc3ccccc3)n2)cc(O)c1O | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(Nc2nc(-c3ccccc3)cs2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[#7:11]-[c:12]>>[c:12]-[#7:11]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+0:1]:[s;H0;D2;+0:10]:1 | null | [] | null | null | 5 | HOUR | 3.8 g of 5-(bromoacetyl)-2,3-dihydroxybenzonitrile dissolved in 25 ml of N,N-dimethylformamide are treated with N-phenylthiourea and stirred at 100° for 5 hours. Thereafter, the solvent is removed by evaporation. The residue is treated with 200 ml of 1N sodium carbonate solution and extracted three times with 100 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccccc1 | HBr | CN(C=O)C | null | 5 | N#Cc1cc(C(=O)CBr)cc(O)c1O.NC(=S)Nc1ccccc1>CN(C=O)C>N#Cc1cc(-c2csc(Nc3ccccc3)n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2fdeb7175db243fd8b1813d6a634da82 | COc1cc(Br)ccc1OCc1ccccc1.O=Cc1ccnc2ccccc12>>COc1cc(C(O)c2ccnc3ccccc23)ccc1OCc1ccccc1 | O.N1=CC=C(C2=CC=CC=C12)C=O.C(C)(C)(C)[Li].C(C1=CC=CC=C1)OC1=C(C=C(C=C1)Br)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(O)C1=CC=NC2=CC=CC=C12)OC | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:19][cH:18]1.[CH:6](=[O:7])[c:8]1[cH:9][cH:10][n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c... | COc1cc(Br)ccc1OCc1ccccc1.O=Cc1ccnc2ccccc12 | COc1cc(C(O)c2ccnc3ccccc23)ccc1OCc1ccccc1 | null | null | O1CCCC1.C(C)(=O)O | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(COc2ccc(Cc3ccnc4ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 1 | HOUR | 25 ml of tert.-butyllithium solution (1.4M in hexane) are added dropwise at -70° within 10 minutes to 10 g of 4-(benzyloxy)-3-methoxy-bromobenzene dissolved in 100 ml of tetrahydrofuran. After stirring at -70° for 1 hour, 5 g of quinoline-4-carbaldehyde dissolved in 50 ml of tetrahydrofuran are added dropwise within 30... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | Br- | O1CCCC1.C(C)(=O)O | null | 1 | COc1cc(Br)ccc1OCc1ccccc1.O=Cc1ccnc2ccccc12>O1CCCC1.C(C)(=O)O>COc1cc(C(O)c2ccnc3ccccc23)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2391726614f84beea4c6846656d926fa | COc1cc(C(=O)c2ccnc3ccccc23)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccnc3ccccc23)ccc1O | C([O-])(O)=O.[Na+].Br.N1=CC=C(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OC>>N1=CC=C(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)O)OC | c1ccc(C[O:21][c:20]2[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[c:8]3[cH:9][cH:10][n:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]34)[cH:18][cH:19]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][cH:19][c:20]1[OH:21] | COc1cc(C(=O)c2ccnc3ccccc23)ccc1OCc1ccccc1 | COc1cc(C(=O)c2ccnc3ccccc23)ccc1O | null | null | C(C)(=O)O.C(Cl)Cl | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1ccnc2ccccc12 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 4.5 | HOUR | 15 ml of 33 percent hydrobromic acid in glacial acetic acid are added dropwise within 5 minutes at room temperature to 7.5 g of 4-(benzyloxy)-3-methoxyphenyl 4-quinolyl ketone dissolved in 150 ml of methylene chloride. After stirring at 20° for 4.5 hours, the reaction mixture is poured portionwise into 250 ml of satura... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2ncccc2c1 | Other | C(C)(=O)O.C(Cl)Cl | null | 4.5 | COc1cc(C(=O)c2ccnc3ccccc23)ccc1OCc1ccccc1>C(C)(=O)O.C(Cl)Cl>COc1cc(C(=O)c2ccnc3ccccc23)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-79d72dfbe430467d8bd631340094b4e0 | COc1cc(C(=O)c2ccnc3ccccc23)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2ccnc3ccccc23)cc([N+](=O)[O-])c1O | N.[N+](=O)(O)[O-].N1=CC=C(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)O)OC>>N1=CC=C(C2=CC=CC=C12)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][cH:19][c:23]1[OH:24].O[N+:20](=[O:21])[O-:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]([N+:20](=[O:21])[O-:22])[c:... | COc1cc(C(=O)c2ccnc3ccccc23)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)c2ccnc3ccccc23)cc([N+](=O)[O-])c1O | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C(c1ccccc1)c1ccnc2ccccc12 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 3 | HOUR | 0.37 ml of 65 percent nitric acid is added dropwise at room temperature to 1.3 g of 4-hydroxy-3-methoxyphenyl 4-quinolyl ketone. After stirring for 3 hours the reaction mixture is poured into ice-water, adjusted to pH 6 with conc. ammonia and the precipitate formed is filtered. The thus-obtained residue is heated under... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1 | HO- | null | null | 3 | COc1cc(C(=O)c2ccnc3ccccc23)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2ccnc3ccccc23)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0e0e72cbaa14419480f213f20421c579 | COc1cc(C(=O)c2ccnc3ccccc23)cc([N+](=O)[O-])c1O>>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1ccnc2ccccc12 | N1=CC=C(C2=CC=CC=C12)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.Br>>Br.N1=CC=C(C2=CC=CC=C12)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | C[O:7][c:6]1[cH:5][c:4]([C:3](=[O:2])[c:15]2[cH:16][cH:17][n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[cH:14][c:10]([N+:11](=[O:12])[O-:13])[c:8]1[OH:9]>>[O:2]=[C:3]([c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1)[c:15]1[cH:16][cH:17][n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12 | COc1cc(C(=O)c2ccnc3ccccc23)cc([N+](=O)[O-])c1O | O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1ccnc2ccccc12 | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1ccnc2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | 1 g of 4-hydroxy-3-methoxy-5-nitrophenyl 4-quinolyl ketone dissolved in 30 ml of 48 percent aqueous hydrobromic acid is stirred at 100° for 18 hours. After cooling to room temperature, the reaction mixture is diluted with 30 ml of water and the precipitate is filtered under suction. There is obtained 3,4-dihydroxy-5-ni... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | O | null | 18 | COc1cc(C(=O)c2ccnc3ccccc23)cc([N+](=O)[O-])c1O>O>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1ccnc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ac475188b08e48ee8e91a622daaf4906 | COc1cc(C=O)cc([N+](=O)[O-])c1OC.[Li][CH2]CCC>>COc1cc(C(O)c2cccs2)cc([N+](=O)[O-])c1OC | C(CCC)[Li].COC=1C=C(C=O)C=C(C1OC)[N+](=O)[O-].S(O)(O)(=O)=O>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(O)C=1SC=CC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]1[O:19][CH3:20].[Li][CH2:10][CH2:11][CH2:9][CH3:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]1[O:19][CH3:20] | COc1cc(C=O)cc([N+](=O)[O-])c1OC.[Li][CH2]CCC | COc1cc(C(O)c2cccs2)cc([N+](=O)[O-])c1OC | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 661e7f8071acc0898ca40b7ca38444f163c7212e8a16f4ad52f40bf89281dbb8 | 18b29b9c7cb3e5d60d4b6da2d631bced0464176d02310b4899c1610484f5ac30 | c1ccc(Cc2cccs2)cc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[Li].[O;H0;D1;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[OH;D1;+0:5]-[CH;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c;H0;D3;+0:1]1:[#16;a:10]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:2]:1 | null | [] | null | null | 30 | MINUTE | 18.8 ml of n-butyllithium solution (1.6M in hexane) are added dropwise at -50° within 10 minutes to 4.03 g of thiophone dissolved in 40 ml of tetrahydrofuran. After stirring at -50° for 30 minutes 6.3 g of 3,4-dimethoxy-5-nitrobenzaldehyde dissolved in 100 ml of tetrahydrofuran are added dropwise within 30 minutes. The... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Alkyl lithium | Secondary alcohol | null | c1ccsc1 | c1ccccc1.c1ccsc1 | null | O1CCCC1 | null | 0.5 | COc1cc(C=O)cc([N+](=O)[O-])c1OC.[Li][CH2]CCC>O1CCCC1>COc1cc(C(O)c2cccs2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c6ffc2b54698401c861526dd4690776e | COc1cc(C(O)c2cccs2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)c2cccs2)cc([N+](=O)[O-])c1OC | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(O)C=1SC=CC1>>S1C(=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]1[O:19][CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]1[O:19][CH3:20] | COc1cc(C(O)c2cccs2)cc([N+](=O)[O-])c1OC | COc1cc(C(=O)c2cccs2)cc([N+](=O)[O-])c1OC | null | [O-2].[O-2].[Mn+4] | CC(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1cccs1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[#16;a:8]:[c:9]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[#16;a:8]:[c:9] | null | [] | null | null | null | null | 9.9 g of α-(3,4-dimethoxy-5-nitrophenyl)-2-thiophenemethanol dissolved in 300 ml of acetone are treated with 90 g of manganese dioxide and heated under reflux for 4 hours. The manganese dioxide is removed by suction filtration and the filtrate is evaporated. There is obtained 3,4-dimethoxy-5-nitrophenyl 2-thienyl keton... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccsc1 | null | [O-2].[O-2].[Mn+4].CC(=O)C | null | null | COc1cc(C(O)c2cccs2)cc([N+](=O)[O-])c1OC>[O-2].[O-2].[Mn+4].CC(=O)C>COc1cc(C(=O)c2cccs2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d4e18fa418d445f6af7e22b2933b4461 | COc1cc(C(=O)c2cccs2)cc([N+](=O)[O-])c1OC>>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1cccs1 | S1C(=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])OC)OC>>S1C(=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | C[O:6][c:5]1[cH:4][c:3]([C:2](=[O:1])[c:14]2[cH:15][cH:16][cH:17][s:18]2)[cH:13][c:9]([N+:10](=[O:11])[O-:12])[c:7]1[O:8]C>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1)[c:14]1[cH:15][cH:16][cH:17][s:18]1 | COc1cc(C(=O)c2cccs2)cc([N+](=O)[O-])c1OC | O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1cccs1 | null | null | C(C)(=O)O.Br | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(c1ccccc1)c1cccs1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 2 g of 3,4-dimethoxy-5-nitrophenyl 2-thienyl ketone are stirred at 100° for 8 hours in a mixture of 20 ml of 30-33 percent hydrobromic acid in glacial acetic acid and 20 ml of 48 percent aqueous hydrobromic acid. The reaction mixture is subsequently evaporated to dryness. The residue is taken up in ethyl acetate, washe... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccsc1 | Other | C(C)(=O)O.Br | null | null | COc1cc(C(=O)c2cccs2)cc([N+](=O)[O-])c1OC>C(C)(=O)O.Br>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1cccs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b0b474ca97b1456681b659e1caf77daf | CC(=O)Nc1ccccc1.O=[N+]([O-])O>>CC(=O)Nc1ccc([N+](=O)[O-])cc1 | C(C)(=O)NC1=CC=CC=C1.[N+](=O)(O)[O-].S(O)(O)(=O)=O>>CC(=O)NC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:12][cH:13]1.O[N+:9](=[O:10])[O-:11]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1 | CC(=O)Nc1ccccc1.O=[N+]([O-])O | CC(=O)Nc1ccc([N+](=O)[O-])cc1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | null | null | nitrating acetanilide using a mixture of nitric acid and sulfuric acid to produce 4-nitroacetanilide and nitrating further using a mixture of nitric acid and sulfuric acid to produce VI;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)Nc1ccccc1.O=[N+]([O-])O>>CC(=O)Nc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3c454c91ecb24bbd82b66c7cb9c203d6 | Nc1c([N+](=O)[O-])cc([N+](=O)[O-])cc1[N+](=O)[O-]>>Nc1c([N+](=O)[O-])cc([N+](=O)[O-])c(N)c1[N+](=O)[O-] | Cl.C1=C(C=C(C(=C1[N+](=O)[O-])N)[N+](=O)[O-])[N+](=O)[O-].C(C1=CC=CC=C1)ON.C[O-].[Na+]>>C1=C(C(=C(C(=C1[N+](=O)[O-])N)[N+](=O)[O-])N)[N+](=O)[O-] | [NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:14]1[N+:15](=[O:16])[O-:17]>>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([NH2:13])[c:14]1[N+:15](=[O:16])[O-:17] | Nc1c([N+](=O)[O-])cc([N+](=O)[O-])cc1[N+](=O)[O-] | Nc1c([N+](=O)[O-])cc([N+](=O)[O-])c(N)c1[N+](=O)[O-] | null | null | CS(=O)C | Functional Group Addition | OtherReaction | 60732f4102305dd78afd0dd3679bbaf7f92e00d937b526eb4d81318ee97c4790 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccccc1 | [#7;+:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[#7;+:6]):[c:7]>>[#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[N;D1;H2:8]):[c:5](-[#7;+:6]):[c:7] | 87.4 | [{"value": 87.0, "product": "C1=C(C(=C(C(=C1[N+](=O)[O-])N)[N+](=O)[O-])N)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "C1=C(C(=C(C(=C1[N+](=O)[O-])N)[N+](=O)[O-])N)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | DMSO (15 ml) is added with rapid stirring to a mixture of picramide (0.477 g, 2.09 mmol), O-benzylhydroxylamine (1.64 g, 10.3 mmol) and sodium methoxide (1.91 g, 35.4 mmol). The brown suspension is stirred at ambient temperature for 15 hr. The reaction mixture is poured into cold 0.12N aqueous HCl (200 ml). The resulti... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CS(=O)C | null | 15 | Nc1c([N+](=O)[O-])cc([N+](=O)[O-])cc1[N+](=O)[O-]>CS(=O)C>Nc1c([N+](=O)[O-])cc([N+](=O)[O-])c(N)c1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7244e5de2c67430a83f92a241e475c14 | CC(=O)Nc1ccccc1.O=[N+]([O-])O>>CC(=O)Nc1ccc([N+](=O)[O-])cc1 | C(C)(=O)NC1=CC=CC=C1.[N+](=O)(O)[O-].S(O)(O)(=O)=O>>CC(=O)NC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:12][cH:13]1.O[N+:9](=[O:10])[O-:11]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1 | CC(=O)Nc1ccccc1.O=[N+]([O-])O | CC(=O)Nc1ccc([N+](=O)[O-])cc1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | null | null | nitrating acetanilide using a mixture of nitric acid and sulfuric acid to produce 4-nitroacetanilide and nitrating further using a mixture of nitric acid and sulfuric acid to produce compound VI;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)Nc1ccccc1.O=[N+]([O-])O>>CC(=O)Nc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d7c519f58a6c4629bc42c97f592c844b | CC(=O)Oc1ccc2c(c1)[C@H](O)C[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12>>C[C@@]12C=CC[C@H]1[C@@H]1C[C@@H](O)c3cc(O)ccc3[C@H]1CC2 | C(C)(=O)OC1=CC=2[C@@H](C[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3C2C=C1)O.C(C)(=O)[O-]>>C[C@@]12C=CC[C@H]1[C@@H]1C[C@H](C=3C=C(C=CC3[C@H]1CC2)O)O | CC(=O)[O:14][c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[C@@H:18]1[C@H:7]([C@H:6]3[C@@:2]([CH3:1])([CH:3]=[CH:4][CH2:5]3)[CH2:20][CH2:19]1)[CH2:8][C@H:9]2[OH:10]>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][C@@H:9]([OH:10])[c:11]3[cH:12][c:13]([OH:14])[cH:15][cH:16][c:17]3[C@H:18]1[CH2:19][CH2:20]2 | CC(=O)Oc1ccc2c(c1)[C@H](O)C[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12 | C[C@@]12C=CC[C@H]1[C@@H]1C[C@@H](O)c3cc(O)ccc3[C@H]1CC2 | null | null | null | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | C1=CC2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 6β-HYDROXYESTRA-1,3,5(10),16-TETRAEN-3-YL ACETATE (Acetate of E12/N1)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | C1=C[C@@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | HO- | null | null | null | CC(=O)Oc1ccc2c(c1)[C@H](O)C[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12>>C[C@@]12C=CC[C@H]1[C@@H]1C[C@@H](O)c3cc(O)ccc3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-33907cecb1614b779cc8c7288c4d0f70 | CC(=O)Oc1ccc2c3c(ccc2c1)[C@@H]1CC=C[C@@]1(C)CC3>>C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C | C(C)(=O)OC1=CC2=CC=C3[C@@H]4CC=C[C@@]4(C)CCC3=C2C=C1.C(C)(=O)[O-]>>C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O | CC(=O)[O:12][c:11]1[cH:10][c:9]2[cH:8][cH:7][c:6]3[c:16]([c:15]2[cH:14][cH:13]1)[CH2:17][CH2:18][C@:19]1([CH3:20])[CH:2]=[CH:3][CH2:4][C@@H:5]31>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][C:9]4=[CH:10][C:11](=[O:12])[CH2:13][CH2:14][C@@H:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20] | CC(=O)Oc1ccc2c3c(ccc2c1)[C@@H]1CC=C[C@@]1(C)CC3 | C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C | null | null | null | Reduction | OtherReaction | c0f1a18ea822e10b2b924b15b29531f2a9546a4fcb3176721a6e21fd9610a270 | 042913d2a4053e95d008323463f697351e585aee96acad85f412a98f9122a77f | C=C1CC[C@@H]2C1CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@@H]21 | C-C(=O)-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]3:[c;H0;D3;+0:8](:[c;H0;D3;+0:9]:2:[cH;D2;+0:10]:[cH;D2;+0:11]:1)-[C:12]-[C:13]-[C:14]1(-[C;D1;H3:15])-[CH;D2;+0:16]=[CH;D2;+0:17]-[C:18]-[C:19]-3-1>>[C;D1;H2:20]=[C;H0;D3;+0:16]1-[CH2;D2;+0:17]-[C:18]-[C:19]2-[C... | null | [] | null | null | null | null | ESTRA-1,3,5,7,9,16-HEXAEN-3-YL ACETATE (Acetate of E10/N1)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Vinyl | C1=C[C@H]2CCc3c(ccc4ccccc34)[C@@H]2C1 | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | Other | null | null | null | CC(=O)Oc1ccc2c3c(ccc2c1)[C@@H]1CC=C[C@@]1(C)CC3>>C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-faefcb6adc014d408ac9431750c1a3af | C[C@@]12C=CC[C@H]1[C@@H]1CC(=O)c3cc(CC(=O)[O-])ccc3[C@H]1CC2>>C[C@@]12C=CC[C@H]1[C@@H]1CC(O)c3cc(O)ccc3[C@H]1CC2 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C1CCOC1.C[C@@]12C=CC[C@H]1[C@@H]1CC(C=3C=C(C=CC3[C@H]1CC2)CC(=O)[O-])=O.C1CCOC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C[C@@]12C=CC[C@H]1[C@@H]1CC(C=3C=C(C=CC3[C@H]1CC2)O)O | O=C(C[c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[C@@H:18]1[C@H:7]([C@H:6]3[C@@:2]([CH3:1])([CH:3]=[CH:4][CH2:5]3)[CH2:20][CH2:19]1)[CH2:8][C:9]2=[O:10])[O-:14]>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH:9]([OH:10])[c:11]3[cH:12][c:13]([OH:14])[cH:15][cH:16][c:17]3[C@H:18]1[CH2:19][CH2:20]2 | C[C@@]12C=CC[C@H]1[C@@H]1CC(=O)c3cc(CC(=O)[O-])ccc3[C@H]1CC2 | C[C@@]12C=CC[C@H]1[C@@H]1CC(O)c3cc(O)ccc3[C@H]1CC2 | null | null | null | Miscellaneous | OtherReaction | cc2f5e8005a287a08c065935489dee192fce1a046b7112c1d4cb35ce45b1c55a | ab1b13ab052e8454aed68379869f83b5f307c8e8172db29eaf75ac46c3da9c09 | C1=CC2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | O=C(-[O-;H0;D1:1])-C-[c;H0;D3;+0:2]1:[c:3]:[c:4](:[c:5]:[c:6]:[c:7]:1)-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]-[C:11]>>[C:11]-[C:10]-[CH;D3;+0:8](-[OH;D1;+0:9])-[c:4]1:[c:3]:[c;H0;D3;+0:2](-[OH;D1;+0:1]):[c:7]:[c:6]:[c:5]:1 | 10 | [{"value": 10.0, "product": "C[C@@]12C=CC[C@H]1[C@@H]1CC(C=3C=C(C=CC3[C@H]1CC2)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of lithium aluminum hydride (LAH, 95%, 46.9 mg, 1.17 mmol) in 5 mL of anhydrous THF was added estra-1,3,5(10),16-tetraen-6-one-3-yl-acetate (6) (422.9 mg, 1.360 mmol) in 5 mL of anhydrous THF dropwise, with stirring. The reaction was stirred 50 min., after which further LAH (46.5 mg, 1.16 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol.Aromatic alcohol | C1=C[C@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | C1=C[C@@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | C1=C[C@@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | Other | null | null | null | C[C@@]12C=CC[C@H]1[C@@H]1CC(=O)c3cc(CC(=O)[O-])ccc3[C@H]1CC2>>C[C@@]12C=CC[C@H]1[C@@H]1CC(O)c3cc(O)ccc3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cc1b14e0a7fe4a6e80978c8fa4432adb | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O>>C[C@@]12CCC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 | Cl.NN.[OH-].[K+].C[C@]12CC[C@@H]3C=4C=CC(=CC4CC=C3[C@@H]1CCC2=O)O>>C[C@@]12CCC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O | O=[C:3]1[C@:2]2([CH3:1])[C@@H:6]([CH2:5][CH2:4]1)[C:7]1=[CH:8][CH2:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH2:3][CH2:4][CH2:5][C@H:6]1[C:7]1=[CH:8][CH2:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[C@H:17]1[CH2:18][CH2:19]2 | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O | C[C@@]12CCC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 | null | null | O.C(COCCO)O | Reduction | OtherReaction | 11b0f05f13f348a1e22dfedd2b26d07f1878b2edd41602781ca10f6aa8c5cfef | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | C1=C2[C@H](CCC3CCC[C@@H]23)c2ccccc2C1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]=[C:6])-[C:7]-1(-[C;D1;H3:8])-[C:9]>>[C:9]-[C:7]1(-[C;D1;H3:8])-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-1-[C:5]=[C:6] | 14 | [{"value": 14.0, "product": "C[C@@]12CCC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.9, "product": "C[C@@]12CCC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of equilin (100.2 mg, 0.3733 mmol) in 2 mL of diethylene glycol were added hydrazine (59 μL, 1.9 mmol) and potassium hydroxide (0.04 g, 0.7 mmol). The mixture was stirred in an oil bath at 200°-214° C. for 2 h, after which the cooled reaction was diluted with 10 mL of water, neutralized with 1N HCl, and... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1=C2[C@H](CC[C@@H]3CCC[C@@H]23)c2ccccc2C1 | C1=C2[C@H](CC[C@H]3CCC[C@@H]23)c2ccccc2C1 | C1=C2[C@H](CC[C@H]3CCC[C@@H]23)c2ccccc2C1 | Other | O.C(COCCO)O | null | 2 | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O>O.C(COCCO)O>C[C@@]12CCC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-13e55dc3a2d64554a99a1dd2a344d976 | C[C@]12CC[C@@H]3c4ccc(O)cc4C=C[C@H]3[C@@H]1CCC2=O>>C[C@@]12CCC[C@H]1[C@@H]1C=Cc3cc(O)ccc3[C@H]1CC2 | Cl.C[C@@]12C(CC[C@H]1[C@@H]1C=CC=3C=C(C=CC3[C@H]1CC2)O)=O.NN.[OH-].[K+]>>C[C@@]12CCC[C@H]1[C@@H]1C=CC=3C=C(C=CC3[C@H]1CC2)O | O=[C:3]1[C@:2]2([CH3:1])[C@@H:6]([CH2:5][CH2:4]1)[C@@H:7]1[CH:8]=[CH:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:7]1[CH:8]=[CH:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[C@H:17]1[CH2:18][CH2:19]2 | C[C@]12CC[C@@H]3c4ccc(O)cc4C=C[C@H]3[C@@H]1CCC2=O | C[C@@]12CCC[C@H]1[C@@H]1C=Cc3cc(O)ccc3[C@H]1CC2 | null | null | O.C(COCCO)O | Reduction | OtherReaction | eecb09633bf6a470053455cdcdf5805617dbff75e27df63d7964b5bd688fd862 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | C1=C[C@@H]2[C@H](CCC3CCC[C@H]32)c2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1(-[C;D1;H3:6])-[C:7]>>[C:7]-[C:5]1(-[C;D1;H3:6])-[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | Estra-1,3,5(10),6-tetraen-3-ol-17-one (91.1 mg, 0.339 mmol), hydrazine (54 μL, 1.7 mmol), and potassium hydroxide (0.06 g) in 1.8 mL of diethylene glycol were heated in a 200° C. bath under argon for 2 h. After cooling to RT 10 mL of water were added and the solution was acidified to pH≈2 with 1N HCl. The resulting sus... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1=C[C@H]2[C@@H]3CCC[C@H]3CC[C@@H]2c2ccccc21 | C1=C[C@H]2[C@@H]3CCC[C@@H]3CC[C@@H]2c2ccccc21 | C1=C[C@H]2[C@@H]3CCC[C@@H]3CC[C@@H]2c2ccccc21 | Other | O.C(COCCO)O | null | null | C[C@]12CC[C@@H]3c4ccc(O)cc4C=C[C@H]3[C@@H]1CCC2=O>O.C(COCCO)O>C[C@@]12CCC[C@H]1[C@@H]1C=Cc3cc(O)ccc3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-64dc57ddcc04413ba25434526df7bca5 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CC[C@@H]3[C@H]1CC2>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(O)CC[C@@H]3[C@H]1CC2 | O.O.O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Na+].[Na+].C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O.C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O | [CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][C:10]3=[CH:11][C:12](=[O:13])[CH2:14][CH2:15][C@@H:16]3[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][C:10]3=[CH:11][CH:12]([OH:13])[CH2:14][CH2:15][C@@H:16]3[C@H:17]1[CH2:18][CH2:19]2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CC[C@@H]3[C@H]1CC2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(O)CC[C@@H]3[C@H]1CC2 | null | null | CCOCC | Reduction | Reduction of ketone to secondary alcohol | dee937cc1d956629e7fc3568753db0f6a443a8832909c31808ca7ad163002c5f | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CC2CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]2C1 | [C:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[C:7]-[C:8]-1>>[C:1]-[C:2]1=[C:3]-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | 17 | MINUTE | To estra-4,16-dien-3-one, (1) (87.2 mg, 0.340 mmol) in 1.7 mL of anh. ether was added lithium aluminum hydride (15.0 mg, 0.395 mmol) and the suspension was stirred 17 min. Reaction was then agitated 10 min. with 0.50 g of sodium sulfate decahydrate and filtered through Celite. The residue was washed with three 10 mL po... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]2C1 | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]2C1 | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]2C1 | null | CCOCC | null | 0.283333 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CC[C@@H]3[C@H]1CC2>CCOCC>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(O)CC[C@@H]3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-03b574ac27ae4dca90e3d4f976fa9ef4 | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CC[C@@H]3[C@H]1CC2 | C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@H]34.C(C)(=O)[O-].CC(=O)OC(=O)C.N#N.C(C)(=O)[O-]>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O | O[C@@H:3]1[C@:2]2([CH3:1])[C@@H:6]([CH2:5][CH2:4]1)[C@@H:7]1[CH2:8][CH2:9][C:10]3=[CH:11][C:12](=[O:13])[CH2:14][CH2:15][C@@H:16]3[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][C:10]3=[CH:11][C:12](=[O:13])[CH2:14][CH2:15][C@@H:16]3[C@H:17]1[CH2:18][CH2:19]2 | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CC[C@@H]3[C@H]1CC2 | null | null | N1=CC=CC=C1.C1(=CC=CC=C1)C.C(Cl)Cl | Functional Group Interconversion | OtherReaction | e0b95ade950374b335849c20f817b6abe1cda9d562afeb4f105c11c5a481b532 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | O=C1C=C2CC[C@@H]3[C@H](CCC4C=CC[C@H]43)[C@H]2CC1 | O-[C@H;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[C:5]-1(-[C;D1;H3:6])-[C:7]>>[C:7]-[C:5]1(-[C;D1;H3:6])-[C:4]-[C:3]-[CH;D2;+0:2]=[CH;D2;+0:1]-1 | 28 | [{"value": 28.0, "product": "C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This synthesis is depicted in FIG. 11. 19-Nor-testosterone (XIX) is commercially available, e.g., from Chemical Dynamics Corp. It provides the starting material for 19-Nor-16-androstene derivatives. 19-Nor-testosterone (XIX) was converted into the acetate (Hartman, J. A. et al., J. Am. Chem. Soc. (1956) 78:5662) with a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]2C1 | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]2C1 | HO- | N1=CC=CC=C1.C1(=CC=CC=C1)C.C(Cl)Cl | null | null | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O>N1=CC=CC=C1.C1(=CC=CC=C1)C.C(Cl)Cl>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CC[C@@H]3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8ea679507e1a43dfb8823c5133c2a071 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3CC(=O)CC[C@@H]3[C@H]1CC2>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3C[C@H](O)CC[C@@H]3[C@H]1CC2 | CCC([BH-](C(CC)C)C(CC)C)C.[Li+].C[C@@]12C=CC[C@H]1[C@@H]1CCC3CC(CC[C@@H]3[C@H]1CC2)=O.[OH-].[Na+].OO>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3C[C@@H](CC[C@@H]3[C@H]1CC2)O | [CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][CH:10]3[CH2:11][C:12](=[O:13])[CH2:14][CH2:15][C@@H:16]3[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][CH:10]3[CH2:11][C@H:12]([OH:13])[CH2:14][CH2:15][C@@H:16]3[C@H:17]1[CH2:18][CH2:19]2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3CC(=O)CC[C@@H]3[C@H]1CC2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3C[C@H](O)CC[C@@H]3[C@H]1CC2 | null | null | O.CCOCC.C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | cb85db3f3980e7ea597896adaf5455a2c05ef13ef2470093bc4791ad567ed2e7 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=CC2CC[C@H]3[C@@H](CCC4CCCC[C@@H]43)[C@@H]2C1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | 87 | [{"value": 87.0, "product": "C[C@@]12C=CC[C@H]1[C@@H]1CCC3C[C@@H](CC[C@@H]3[C@H]1CC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "C[C@@]12C=CC[C@H]1[C@@H]1CCC3C[C@@H](CC[C@@H]3[C@H]1CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | This synthesis is depicted in FIG. 11. L-Selectride (d, lithium tri(sec-butyl)hydridoborate, 4 ml of a 1M solution in THF, 4 mmol) was added dropwise at 0° to a solution of ketone 10 (800 mg, 3.10 mmol) in dry ether (5 ml). After stirring for 1 h at 0°, water was added (10 ml). The boranes were oxidized by adding 10% a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4CCCC[C@@H]43)[C@@H]2C1 | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4CCCC[C@@H]43)[C@@H]2C1 | C1=C[C@@H]2CC[C@H]3[C@@H](CCC4CCCC[C@@H]43)[C@@H]2C1 | null | O.CCOCC.C1CCOC1 | null | 1 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3CC(=O)CC[C@@H]3[C@H]1CC2>O.CCOCC.C1CCOC1>C[C@@]12C=CC[C@H]1[C@@H]1CCC3C[C@H](O)CC[C@@H]3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4eb3c756514440079e34b385af51e750 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=C(CCC(=O)C3)[C@H]1CC2>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CCC3=C1CC2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC=3CC(CCC3[C@H]1CC2)=O.C[C@@]12C=CC[C@H]1[C@@H]1CCC=3CC(CCC3[C@H]1CC2)=O.N1=CC=CC=C1.C1(=CC=CC=C1)O>>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CCC3=C1CC2)=O | [CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][C:10]3=[C:16]([CH2:15][CH2:14][C:12](=[O:13])[CH2:11]3)[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH2:9][C:10]3=[CH:11][C:12](=[O:13])[CH2:14][CH2:15][C:16]3=[C:17]1[CH2:18][CH2:19]2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=C(CCC(=O)C3)[C@H]1CC2 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CCC3=C1CC2 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 90fc578482e51c8b1c4837e66a0377326f0e500906b54de91f1021394be28d13 | f394080031812a9c0cde55fa330311dfe42bea38dbdf0b4621700859838ffa32 | O=C1C=C2CC[C@@H]3C(=C2CC1)CCC1C=CC[C@H]13 | [C:1]-[C:2]-[C@H;D3;+0:3]1-[C:4](-[C:5])-[C:6]-[C:7]-[C;H0;D3;+0:8]2=[C;H0;D3;+0:9]-1-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-2>>[C:1]-[C:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:9]2-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[CH;D2;+0:14]=[C;H0;D3;+0:8]-2-[C:7]-[C:6]-[C:4]-1-[C:5] | 31 | [{"value": 31.0, "product": "C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(CCC3=C1CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | MINUTE | Estra-5(10),16-dien-3-one, 3 (0.38 g, 1.5 mmol), in pyridine (5.0 mL, 62 mmol) was cooled in an ice-salt bath to -13° C. and pyridinium bromide perbromide (1.58 g, 4.94 mmol) was added in small portions so that T<-4° C. After swirling 1 min. phenol (0.25 g, 2.7 mmol) was added and reaction continued 24 h at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=C[C@@H]2CC[C@@H]3C4=C(CCCC4)CC[C@H]3[C@@H]2C1 | C1=C[C@@H]2CCC3=C4CCCC=C4CC[C@H]3[C@@H]2C1 | C1=C[C@@H]2CCC3=C4CCCC=C4CC[C@H]3[C@@H]2C1 | null | C(C)(=O)OCC | null | 0.016667 | C[C@@]12C=CC[C@H]1[C@@H]1CCC3=C(CCC(=O)C3)[C@H]1CC2>C(C)(=O)OCC>C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(=O)CCC3=C1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-52f5f6e37c8948ff842063e43a31449a | CC(=O)Oc1ccc2c(c1)C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12>>C[C@@]12C=CC[C@H]1[C@@H]1CC(O)c3cc(O)ccc3[C@H]1CC2 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)(=O)OC1=CC=2C(C[C@H]3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3C2C=C1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C[C@@]12C=CC[C@H]1[C@@H]1CC(C=3C=C(C=CC3[C@H]1CC2)O)O | CC(=O)[O:14][c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[C@@H:18]1[C@H:7]([C@H:6]3[C@@:2]([CH3:1])([CH:3]=[CH:4][CH2:5]3)[CH2:20][CH2:19]1)[CH2:8][C:9]2=[O:10]>>[CH3:1][C@@:2]12[CH:3]=[CH:4][CH2:5][C@H:6]1[C@@H:7]1[CH2:8][CH:9]([OH:10])[c:11]3[cH:12][c:13]([OH:14])[cH:15][cH:16][c:17]3[C@H:18]1[CH2:19][CH2:20]2 | CC(=O)Oc1ccc2c(c1)C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12 | C[C@@]12C=CC[C@H]1[C@@H]1CC(O)c3cc(O)ccc3[C@H]1CC2 | null | null | C1CCOC1 | Reduction | OtherReaction | 5c3011efb770f5bb284f9eda986003f634d1804b0054957f56865b0f5cfeb83c | 0ceccbeb1a171407aae4661a0628d0d4c1bc76338bade38dd330e39814e68322 | C1=CC2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](:[c:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[CH;D3;+0:7](-[OH;D1;+0:8])-[c:5](:[c:6]):[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 10 | [{"value": 10.0, "product": "C[C@@]12C=CC[C@H]1[C@@H]1CC(C=3C=C(C=CC3[C@H]1CC2)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of lithium aluminum hydride (LAH, 95%, 46.9 mg, 1.17 mmol) in 5 mL of anhydrous THF was added estra-1,3,5(10),16-tetraen-6-one-3-yl acetate, 6 (422.9 mg, 1.360 mmol) in 5 mL of anhydrous THF dropwise, with stirring. See FIG. 13. The reaction was stirred 50 min., after which further LAH (46.5 mg, 1.16 mm... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Secondary alcohol.Aromatic alcohol | C1=C[C@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | C1=C[C@@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | C1=C[C@@H]2CC[C@@H]3c4ccccc4CC[C@H]3[C@@H]2C1 | Other | C1CCOC1 | null | null | CC(=O)Oc1ccc2c(c1)C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C=CC[C@@H]12>C1CCOC1>C[C@@]12C=CC[C@H]1[C@@H]1CC(O)c3cc(O)ccc3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8d6ef4ffcec455e83cfc0cf4e62d64c | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O>>C[C@@]12CCC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 | NN.[OH-].[K+].C[C@]12CC[C@@H]3C=4C=CC(=CC4CC=C3[C@@H]1CCC2=O)O.Cl>>C[C@@]12CCC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O | O=[C:3]1[C@:2]2([CH3:1])[C@@H:6]([CH2:5][CH2:4]1)[C:7]1=[CH:8][CH2:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[C@H:17]1[CH2:18][CH2:19]2>>[CH3:1][C@@:2]12[CH2:3][CH2:4][CH2:5][C@H:6]1[C:7]1=[CH:8][CH2:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[C@H:17]1[CH2:18][CH2:19]2 | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O | C[C@@]12CCC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 | null | null | O.C(COCCO)O | Reduction | OtherReaction | 11b0f05f13f348a1e22dfedd2b26d07f1878b2edd41602781ca10f6aa8c5cfef | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | C1=C2[C@H](CCC3CCC[C@@H]23)c2ccccc2C1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]=[C:6])-[C:7]-1(-[C;D1;H3:8])-[C:9]>>[C:9]-[C:7]1(-[C;D1;H3:8])-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-1-[C:5]=[C:6] | 14 | [{"value": 14.0, "product": "C[C@@]12CCC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.9, "product": "C[C@@]12CCC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of equilin (100.2 mg, 0.3733 mmol) in 2 mL of diethylene glycol were added hydrazine (59 μL, 1.9 mmol) and potassium hydroxide (0.04 g, 0.7 mmol). See FIG. 14. The mixture was stirred in an oil bath at 200°-214° C. for 2h, after which the cooled reaction was diluted with 10 mL of water, neutralized with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1=C2[C@H](CC[C@@H]3CCC[C@@H]23)c2ccccc2C1 | C1=C2[C@H](CC[C@H]3CCC[C@@H]23)c2ccccc2C1 | C1=C2[C@H](CC[C@H]3CCC[C@@H]23)c2ccccc2C1 | Other | O.C(COCCO)O | null | null | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O>O.C(COCCO)O>C[C@@]12CCC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-97916d286a614ca395578599dd7642c2 | CC(=O)OC(C)=O.C[C@@]12C=CC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2>>CC(=O)Oc1ccc2c(c1)CC=C1[C@@H]2CC[C@]2(C)C=CC[C@@H]12 | C[C@@]12C=CC[C@H]1C1=CCC=3C=C(C=CC3[C@H]1CC2)O.N1=CC=CC=C1.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=CC=2CC=C3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3C2C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH:12]=[C:13]1[C@@H:14]2[CH2:15][CH2:16][C@:17]2([CH3:18])[CH:19]=[CH:20][CH2:21][C@@H:22]12>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH:12]=[C:13]1[C@@H:14]2[CH2:15][CH2:16][C@:17]2([CH3:18])[CH:19]=[CH:2... | CC(=O)OC(C)=O.C[C@@]12C=CC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2 | CC(=O)Oc1ccc2c(c1)CC=C1[C@@H]2CC[C@]2(C)C=CC[C@@H]12 | null | null | C(C)(=O)OCC | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | C1=CC2CC[C@H]3C(=CCc4ccccc43)[C@@H]2C1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 35.1 | [{"value": 35.0, "product": "C(C)(=O)OC1=CC=2CC=C3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3C2C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.1, "product": "C(C)(=O)OC1=CC=2CC=C3[C@@H]4CC=C[C@@]4(C)CC[C@@H]3C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of estra-1,3,5(10),7,16-pentaen-3-ol (5, 192.1 mg, 0.7612 mmol) in anh. pyridine (2.6 mL, 32 mmol) and acetic anhydride (0.36 mL, 3.8 mmol) was stirred 6 h, after which 30 mL, of ethyl acetate were added. The mixture was washed with three 10 mL portions of 1M hydrochloric acid+10 mL of saturated sodium bicar... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | C1=C[C@H]2CC[C@H]3C(=CCc4ccccc43)[C@@H]2C1 | HO- | C(C)(=O)OCC | null | null | CC(=O)OC(C)=O.C[C@@]12C=CC[C@H]1C1=CCc3cc(O)ccc3[C@H]1CC2>C(C)(=O)OCC>CC(=O)Oc1ccc2c(c1)CC=C1[C@@H]2CC[C@]2(C)C=CC[C@@H]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-468cb3245f1d495c916c0c2155cad422 | CC(=O)OC(C)=O.C[C@@]12C=CC[C@H]1c1ccc3cc(O)ccc3c1CC2>>CC(=O)Oc1ccc2c3c(ccc2c1)[C@@H]1CC=C[C@@]1(C)CC3 | C[C@@]12C=CC[C@H]1C=1C=CC=3C=C(C=CC3C1CC2)O.N1=CC=CC=C1.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=CC=2C=CC=3[C@@H]4CC=C[C@@]4(C)CCC3C2C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]3[c:10]([cH:11][cH:12][c:13]2[cH:14]1)[C@@H:15]1[CH2:16][CH:17]=[CH:18][C@@:19]1([CH3:20])[CH2:21][CH2:22]3>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]3[c:10]([cH:11][cH:12][c:13]2[cH:14]1)[C@@H:15]1[CH2:16][CH:17]=[CH:18][C@@:19]1([CH3:20])[CH2... | CC(=O)OC(C)=O.C[C@@]12C=CC[C@H]1c1ccc3cc(O)ccc3c1CC2 | CC(=O)Oc1ccc2c3c(ccc2c1)[C@@H]1CC=C[C@@]1(C)CC3 | null | null | C(C)(=O)OCC | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | C1=CC2CCc3c(ccc4ccccc34)[C@@H]2C1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A solution of estra-1,3,5(10),6,8,16-hexaen-3-ol Q8, 148.8 mg, 0.5944 mmol) in anh. pyridine (2.0 mL, 25 mmol) and acetic anhydride (0.28 mL, 3.0 mmol) was stirred 6 h, after which ethyl acetate (20 mL) was added. See FIG. 16. The mixture was washed with three 10 mL portions of 1N hydrochloric acid+10 mL of saturated s... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | C1=C[C@H]2CCc3c(ccc4ccccc34)[C@@H]2C1 | HO- | C(C)(=O)OCC | null | null | CC(=O)OC(C)=O.C[C@@]12C=CC[C@H]1c1ccc3cc(O)ccc3c1CC2>C(C)(=O)OCC>CC(=O)Oc1ccc2c3c(ccc2c1)[C@@H]1CC=C[C@@]1(C)CC3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f5acae62e6b3429fbdd22b19dd4f3794 | C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O>>C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C | CC(C)([O-])C.[K+].C[C@]12CC[C@@H]3C=4C=CC(=CC4CC[C@H]3[C@@H]1CCC2=O)O>>C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O | O=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20] | C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CS(=O)C | Functional Group Interconversion | OtherReaction | 2a089c86876da4b63340b50ce6162eb9d8dae1d5c1a6286dd27616876622d717 | f395a9efbb80a99833acb686d4944d4880257993d074f4e04e21822999af09fe | C=C1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1(-[C;D1;H3:6])-[C:7]>>[C:7]-[C:5]1(-[C;D1;H3:6])-[C:4]-[C:3]-[C:2]-[C;H0;D3;+0:1]-1=[C;D1;H2:8] | 76.3 | [{"value": 76.0, "product": "C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of methyltriphenylphosphonium bromide (100.03 g, 0.28001 mol) and potassium t-butoxide (31.42 g, 0.2800 mol) in anh. dimethylsulfoxide (DMSO, 320 mL) under argon was stirred in an oil bath (68°-81° C.) 1 h, after which estrone (15.14 g, 55.99 mmol) in anh. DMSO (320 mL) was added via syringe. See FIG. 17. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)C | null | 1 | C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)C>C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d81d78f7d3a948e5a0a669fa1bb5c419 | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C.CC(=O)OC(C)=O>>C=C1CC[C@H]2[C@@H]3CCc4cc(OC(C)=O)ccc4[C@H]3CC[C@]12C | C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O.N1=CC=CC=C1.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1)=C | [CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([OH:12])[cH:16][cH:17][c:18]4[C@H:19]3[CH2:20][CH2:21][C@:22]12[CH3:23].CC(=O)O[C:13]([CH3:14])=[O:15]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([O:12][C:13]([CH3:14])=[O:15])[cH:16][cH:17][c:18]4[C@H:19... | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C.CC(=O)OC(C)=O | C=C1CC[C@H]2[C@@H]3CCc4cc(OC(C)=O)ccc4[C@H]3CC[C@]12C | null | null | C(C)(=O)OCC | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | C=C1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A solution of 17-methylenestra-1,3,5(10)-trien-3-ol (10, 5.84 g, 21.8 mmol) in anh. pyridine (32 mL, 0.40 mol) and acetic anhydride (9.7 mL, 0.10 mol) was stirred 24, after which ethyl acetate (250 mL) was added. See FIG. 17. The mixture was washed with three 100 mL portions of 1N hydrochloric acid+100 mL of saturated ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | HO- | C(C)(=O)OCC | null | null | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C.CC(=O)OC(C)=O>C(C)(=O)OCC>C=C1CC[C@H]2[C@@H]3CCc4cc(OC(C)=O)ccc4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fa3190d1b079451ab839b5c743c6536d | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C.COS(=O)(=O)OC>>C=C1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C | S(=O)(=O)(OC)OC.O.C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O.C([O-])([O-])=O.[K+].[K+].S(=O)(=O)(OC)OC>>COC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1)=C | [CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([OH:12])[cH:14][cH:15][c:16]4[C@H:17]3[CH2:18][CH2:19][C@:20]12[CH3:21].COS(=O)(=O)O[CH3:13]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]4[C@H:17]3[CH2:18][CH2:19][C@:20]... | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C.COS(=O)(=O)OC | C=C1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C | null | null | C(C)O | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | C=C1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 69 | [{"value": 69.0, "product": "COC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "COC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 17-methylenestra-1,3,5(10)-trien-3-ol (5.37 g, 20.0 mmol) and potassium carbonate (50.82 g, 0.3678 mol) at reflux in 90% ethanol (500 mL) was added dimethyl sulfate (5.0 mL, 53 mmol). After 1/2 h reflux additional dimethyl sulfate (36 mL, 0.38 mol, in three 12 mL aliquots) was added over the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | HO- | C(C)O | null | null | C=C1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C.COS(=O)(=O)OC>C(C)O>C=C1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fb10217d359f48f58ad443914a1b25a3 | C=C1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C>>C=C1CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@]12C | N.COC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1)=C.C(C)(C)(C)O.[Li]>>COC=1CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2CC1)=C | [CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[c:10]([cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16]4)[C@H:17]3[CH2:18][CH2:19][C@:20]12[CH3:21]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][C:9]4=[C:10]([CH2:11][CH:12]=[C:13]([O:14][CH3:15])[CH2:16]4)[C@H:17]3[CH2:18][CH2:19][C@:20]12[CH3... | C=C1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C | C=C1CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@]12C | null | null | O.CO.C1CCOC1 | Miscellaneous | OtherReaction | cd6b08444c76e87f4ece7264249dc37390bc498e903fcc9da807aa1c49e6b2c3 | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | C=C1CC[C@@H]2C1CC[C@@H]1C3=C(CC=CC3)CC[C@H]12 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[c;H0;D3;+0:6]2:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[#8:9]-[C;D1;H3:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:2-1>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]2=[C;H0;D3;+0:13]-1-[CH2;D2;+0:12]-[CH;D2;+0:11]=[C;H0;D3;+0:8](-[#8:9]-[C;D1;H3:10])-[CH2;D2;+0:7]-2 | 72 | [{"value": 72.0, "product": "COC=1CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2CC1)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "COC=1CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2CC1)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Approximately 70 mL of anh. ammonia was distilled through a KOH tower into a 250 mL flame-dried 3-neck flask fitted with an inlet adapter, magnetic stirring bar, dry ice/acetone condenser, and ground glass stopper. See FIG. 17. A solution of 17-methylenestra-1,3,5(10)-trien-3-yl methyl ether (14, 1.1297 g, 4.0001 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | C1=CCC2=C(C1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | C1=CCC2=C(C1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | null | O.CO.C1CCOC1 | null | 8 | C=C1CC[C@H]2[C@@H]3CCc4cc(OC)ccc4[C@H]3CC[C@]12C>O.CO.C1CCOC1>C=C1CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fe253937794b47dba1a5c9239e4b8e93 | C=C1CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@]12C>>C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C | Cl.O.COC=1CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2CC1)=C.C([O-])(O)=O.[Na+]>>C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O | C[O:12][C:11]1=[CH:13][CH2:14][C:15]2=[C:9]([CH2:8][CH2:7][C@H:6]3[C@@H:5]4[CH2:4][CH2:3][C:2](=[CH2:1])[C@@:19]4([CH3:20])[CH2:18][CH2:17][C@@H:16]32)[CH2:10]1>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][C:9]4=[CH:10][C:11](=[O:12])[CH2:13][CH2:14][C@@H:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20] | C=C1CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@]12C | C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C | null | null | CC(=O)C.CO | Miscellaneous | OtherReaction | ea3d0afa2d1ffd7144e5caf5674fcf0682e454869e2a8d1788fe76c2c7afe20e | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | C=C1CC[C@@H]2C1CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@@H]21 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[C;H0;D3;+0:5]2=[C;H0;D3;+0:6](-[C:7]-[C:8]-[C:9]-[C:10]-2-[C:11])-[CH2;D2;+0:12]-1>>[C:11]-[C:10]1-[C:9]-[C:8]-[C:7]-[C;H0;D3;+0:6]2=[CH;D2;+0:12]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH2;D2;+0:3]-[C:4]-[C@H;D3;+0:5]-1-2 | null | [] | null | null | 1 | HOUR | Con. hydrochloric acid (6.0 mL) and water (6.0 mL) were added to a solution of 17-methylenestra-2,5(10)-dien-3-yl methyl ether (15, 702.8 mg. 2.471 mmol) in methanol (6 mL) and acetone (20 mL). See Example 17. After stirring 1 h, sodium bicarbonate (7.50 g) was added cautiously. The mixture was concentrated under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCC2=C(C1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | Other | CC(=O)C.CO | null | 1 | C=C1CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@]12C>CC(=O)C.CO>C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-95307c0c52d74de4a0f61e340d47b4aa | C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C>>C=C1CC[C@H]2[C@@H]3CCC4=C[C@@H](O)CC[C@@H]4[C@H]3CC[C@]12C | C(C)(C)(C)O[AlH-](OC(C)(C)C)OC(C)(C)C.[Li+].C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)=O.[O-]S(=O)(=O)[O-].[Na+].[Na+]>>C=C1[C@]2(C)[C@@H](CC1)[C@@H]1CCC3=C[C@H](CC[C@@H]3[C@H]1CC2)O | [CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][C:9]4=[CH:10][C:11](=[O:12])[CH2:13][CH2:14][C@@H:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][C:9]4=[CH:10][C@@H:11]([OH:12])[CH2:13][CH2:14][C@@H:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20] | C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C | C=C1CC[C@H]2[C@@H]3CCC4=C[C@@H](O)CC[C@@H]4[C@H]3CC[C@]12C | null | null | CCOCC | Reduction | Reduction of ketone to secondary alcohol | 390b75d1195a100e50c97c7f859b524c3c3615b11c43a66f31167fa5991c4f1b | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C=C1CC[C@@H]2C1CC[C@H]1[C@H]2CCC2=CCCC[C@@H]21 | [C:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[C:7]-[C:8]-1>>[C:1]-[C:2]1=[C:3]-[C@@H;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | 4 | HOUR | Lithium tri-t-butoxyaluminohydride (766.6 mg, 3.015 mmol) was added to a solution of 17-methylenestr-4-en-3-one (16, 203.7 mg, 0.7533 mmol) in 10 mL of anh. ether and the reaction was stirred 4 h. See FIG. 18. Glauber's salt (3.80 g) was added and the suspension was stirred an additional 1/2 h. The mixture was filtered... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | C1=C2CC[C@H]3[C@@H]4CCC[C@H]4CC[C@@H]3[C@H]2CCC1 | null | CCOCC | null | 4 | C=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C>CCOCC>C=C1CC[C@H]2[C@@H]3CCC4=C[C@@H](O)CC[C@@H]4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0e8369bf0a9a4d91adb66baad07b17e0 | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O>>C=C1CC[C@H]2C3=CCc4cc(O)ccc4[C@H]3CC[C@]12C | CC(C)([O-])C.[K+].C[C@]12CC[C@@H]3C=4C=CC(=CC4CC=C3[C@@H]1CCC2=O)O>>C=C1[C@]2(C)[C@@H](CC1)C1=CCC=3C=C(C=CC3[C@H]1CC2)O | O=[C:2]1[CH2:3][CH2:4][C@H:5]2[C:6]3=[CH:7][CH2:8][c:9]4[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C:6]3=[CH:7][CH2:8][c:9]4[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]4[C@H:16]3[CH2:17][CH2:18][C@:19]12[CH3:20] | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O | C=C1CC[C@H]2C3=CCc4cc(O)ccc4[C@H]3CC[C@]12C | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CS(=O)C | Functional Group Interconversion | OtherReaction | 305fb2af506a862f4985a5f618ab133b7f9e59303be672ddaa067c5a17ed4016 | f395a9efbb80a99833acb686d4944d4880257993d074f4e04e21822999af09fe | C=C1CC[C@H]2C3=CCc4ccccc4[C@H]3CCC12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]=[C:6])-[C:7]-1(-[C;D1;H3:8])-[C:9]>>[C:9]-[C:7]1(-[C;D1;H3:8])-[C:4](-[C:3]-[C:2]-[C;H0;D3;+0:1]-1=[C;D1;H2:10])-[C:5]=[C:6] | null | [] | null | null | 1 | HOUR | Methyltriphenylphosphonium bromide (1.9967 g, 5.5892 mmol) and potassium t-butoxide (627.2 mg, 5.589 mmol) suspended in 6.1 mL of anh. DMSO under argon were 1 h in an oil bath (71°-83° C., after which equilin (300.0 mg, 1.118 mmol) in 6.1 μL of anh. DMSO was added via syringe. See FIG. 18. After stirring a further 70 m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | C1=C2[C@H](CC[C@@H]3CCC[C@@H]23)c2ccccc2C1 | C1=C2[C@H](CC[C@@H]3CCC[C@@H]23)c2ccccc2C1 | C1=C2[C@H](CC[C@@H]3CCC[C@@H]23)c2ccccc2C1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)C | null | 1 | C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)C>C=C1CC[C@H]2C3=CCc4cc(O)ccc4[C@H]3CC[C@]12C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2e0ece114db9467e960ec8e99788788f | C=CCBr.C=Cc1ccc(OC(C)=O)cc1>>C=CCOc1ccc(C=C)cc1 | C(C)(=O)OC1=CC=C(C=C)C=C1.C(C=C)Br>>C(C=C)OC1=CC=C(C=C)C=C1 | Br[CH2:3][CH:2]=[CH2:1].CC(=O)[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH2:10])[cH:11][cH:12]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH2:10])[cH:11][cH:12]1 | C=CCBr.C=Cc1ccc(OC(C)=O)cc1 | C=CCOc1ccc(C=C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 627a64bd2b77f284ffc6fe82ac9807d934aaaf644e904d52b272599944577038 | cdd4d9002f407af0bc850abdcb3e8813f27873457591f92bc1a76b4ee9a3be0c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].C-C(=O)-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 82 | [{"value": 82.0, "product": "C(C=C)OC1=CC=C(C=C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction described in Example 1 was repeated on the same scale but with the reaction temperature maintained in the range of 4°-6° C., rather than 10° C., during the addition of 4-acetoxystyrene and allyl bromide. In this case, 4-allyloxystyrene was obtained in 82% yield following vacuum distillation. Residual conce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ether | null | null | c1ccccc1 | HBr | null | null | null | C=CCBr.C=Cc1ccc(OC(C)=O)cc1>>C=CCOc1ccc(C=C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e7db0fa7d4e34c8d9ea16de03925fd0f | C=CCBr.C=Cc1ccc(OC(C)=O)cc1>>C=CCOc1ccc(C=C)cc1 | C(C)(=O)OC1=CC=C(C=C)C=C1.C(C=C)Br>>C(C=C)OC1=CC=C(C=C)C=C1 | Br[CH2:3][CH:2]=[CH2:1].CC(=O)[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH2:10])[cH:11][cH:12]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH2:10])[cH:11][cH:12]1 | C=CCBr.C=Cc1ccc(OC(C)=O)cc1 | C=CCOc1ccc(C=C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 627a64bd2b77f284ffc6fe82ac9807d934aaaf644e904d52b272599944577038 | cdd4d9002f407af0bc850abdcb3e8813f27873457591f92bc1a76b4ee9a3be0c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].C-C(=O)-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 66 | [{"value": 66.0, "product": "C(C=C)OC1=CC=C(C=C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction described in Example 1 was repeated on the same scale but with the reaction temperature maintained at ambient (23° C.), rather than 10° C., during the addition of 4-acetoxystyrene and allyl bromide. In this case, 4-allyloxystyrene was obtained in 66 % yield following vacuum distillation.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ether | null | null | c1ccccc1 | HBr | null | null | null | C=CCBr.C=Cc1ccc(OC(C)=O)cc1>>C=CCOc1ccc(C=C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-63cf88ed289a47f680735419176263a5 | C=CCBr.C=Cc1ccc(OC(C)=O)cc1>>C=CCOc1ccc(C=C)cc1 | C(C)(=O)OC1=CC=C(C=C)C=C1.[OH-].[K+].O.C(C=C)Br>>C(C=C)OC1=CC=C(C=C)C=C1 | Br[CH2:3][CH:2]=[CH2:1].CC(=O)[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH2:10])[cH:11][cH:12]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH2:10])[cH:11][cH:12]1 | C=CCBr.C=Cc1ccc(OC(C)=O)cc1 | C=CCOc1ccc(C=C)cc1 | null | null | O1CCOCC1.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 627a64bd2b77f284ffc6fe82ac9807d934aaaf644e904d52b272599944577038 | cdd4d9002f407af0bc850abdcb3e8813f27873457591f92bc1a76b4ee9a3be0c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].C-C(=O)-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 5 | CELSIUS | 2.5 | HOUR | To a 4-necked, nitrogen swept, 2 liter glass reaction vessel equipped with a mechanical stirrer, double-walled condenser, thermocouple and pressure compensating addition funnel is added 1,4-dioxane (600 mls), potassium hydroxide (112.0 g, 2.00 moles) and water (39 g). The mixture is stirred and cooled to 10° C. at whic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ether | null | null | c1ccccc1 | HBr | O1CCOCC1.C1(=CC=CC=C1)C | 5 | 2.5 | C=CCBr.C=Cc1ccc(OC(C)=O)cc1>O1CCOCC1.C1(=CC=CC=C1)C>C=CCOc1ccc(C=C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f24cc0230cab430e999525bce7ab4a89 | c1ccc(N=Nc2ccccc2)cc1>>c1ccc(N=Nc2ccc(Nc3ccccc3)cc2)cc1 | N(=NC1=CC=CC=C1)C1=CC=CC=C1>>C1=CC=C(C=C1)NC2=CC=C(C=C2)N=NC3=CC=CC=C3 | [cH:1]1[cH:3][c:4]([N:5]=[N:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:20][cH:21][cH:7]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]=[N:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1 | c1ccc(N=Nc2ccccc2)cc1 | c1ccc(N=Nc2ccc(Nc3ccccc3)cc2)cc1 | null | null | NC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 64b7165b3362727a5e4a6fea8f01ad1f3bfa61b4d1e9957fe4d0366099fdd975 | f133b56cb7805e90c3a5a052e39a2b7100d8327860d3b4578b7c2e2fce369e36 | c1ccc(N=Nc2ccc(Nc3ccccc3)cc2)cc1 | [c:1]:[c:2](-[N;H0;D2;+0:3]=[N;H0;D2;+0:4]-[c:5]1:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1):[c:11]>>[c:1]:[c:2](-[NH;D2;+0:3]-[c:12]1:[c:13]:[c:14]:[c;H0;D3;+0:8](-[#7:15]=[N;H0;D2;+0:4]-[c:5]2:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:9]:[c:16]:[cH;D2;+0:10]:2):[c:17]:[c:18]:1):[c:11] | 90 | [{"value": 90.0, "product": "C1=CC=C(C=C1)NC2=CC=C(C=C2)N=NC3=CC=CC=C3", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 25% aqueous tetramethylammonium hydroxide (8 mL) was concentrated under vacuum at 75° C. until solid material formed. Azobenzene (1.8 g) and aniline (10 mL) were added and the solution was stirred under the same conditions for 4 hours and then in the presence of air for 12 hours. Analysis of the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Diazene | Diazene.Secondary amine | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | NC1=CC=CC=C1 | null | 4 | c1ccc(N=Nc2ccccc2)cc1>NC1=CC=CC=C1>c1ccc(N=Nc2ccc(Nc3ccccc3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-44988dfca7bd41258d4d28be93b8e091 | C=CC(=C)C>>C=CC(=C)C | C=CC=C.C(C)(=O)O.C(CCC)[Li].C(CCC)[Li].C=CC(C)=C.C=CC(C)=C.C=CC=C.O1CCCC1.C=CC(C)=C>>C=CC(C)=C.C=CC=C.C=CC(C)=C | [CH2:6]=[CH:7][C:8](=[CH2:9])[CH3:10]>>[CH2:6]=[CH:7][C:8](=[CH2:9])[CH3:10] | C=CC(=C)C | C=CC(=C)C | null | null | C1CCCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 50 | CELSIUS | 1 | HOUR | Three hundred milliliters (mL) of purified, dried cyclohexane was introduced into a six-hundred milliliter stirred glass reactor. Air was removed from the reactor under vacuum and replaced by dry nitrogen. The reactor was equipped with an air driven stirrer, a pressure gauge, thermocouple, top face inlet valve, dip tub... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C1CCCCC1 | 50 | 1 | C=CC(=C)C>C1CCCCC1>C=CC(=C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0c25e0f6a1bf4fe58b27283b9cf351bd | C=CC=C.C[CH2][Al]([CH2]C)[CH2]C>>C=CC(=C)C.C=CC=C | [H][H].[H][H].[OH-].[NH4+].N.C=CC=C.C=CC(C)=C.[H][H].C(C)[Al](CC)CC.[H][H].[H][H]>>C=CC(C)=C.C=CC=C.C=CC(C)=C | [CH2:11]=[CH:12][CH:13]=[CH2:14].[CH2]([Al]([CH2:2][CH3:1])[CH2:3][CH3:5])[CH3:4]>>[CH2:1]=[CH:2][C:3](=[CH2:4])[CH3:5].[CH2:11]=[CH:12][CH:13]=[CH2:14] | C=CC=C.C[CH2][Al]([CH2]C)[CH2]C | C=CC(=C)C.C=CC=C | null | CCCCCCCC(=O)[O-].CCCCCCCC(=O)[O-].[Ni+2].[Ni] | C1CCCCC1.CO | C-C Coupling | C-methylation | 19f47f0a1c39d163ea22e2abf31005b56a6bc0ddcea0a4676c93bcfa8578de99 | 9295f74b88ae60b5ebc8d79e405026bba0c3f5a8811447b0a4357dab1e3ec179 | null | [C;D1;H3:1]-[CH2;D2;+0:2]-[Al](-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2]-[CH3;D1;+0:5]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:5])-[CH;D2;+0:3]=[CH2;D1;+0:4] | null | [] | 50 | CELSIUS | 30 | MINUTE | A solution of 250 mL of cyclohexane and 23 g of a triblock polymer prepared in a manner similar to that described in Example I was purged of air by evacuation followed by introduction of dry nitrogen. This amount of polymer contained 0.403 moles of polybutadiene unsaturation. To the polymer solution was added 25 mL of ... | 10.6084/m9.figshare.5104873.v1 | null | null | Vinyl.Vinyl | null | null | null | Other | CCCCCCCC(=O)[O-].CCCCCCCC(=O)[O-].[Ni+2].[Ni].C1CCCCC1.CO | 50 | 0.5 | C=CC=C.C[CH2][Al]([CH2]C)[CH2]C>CCCCCCCC(=O)[O-].CCCCCCCC(=O)[O-].[Ni+2].[Ni].C1CCCCC1.CO>C=CC(=C)C.C=CC=C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-595f7592228d409abede8d544a1ed793 | C[CH2][Al]([CH2]C)[CH2]C>>C=CC(=C)C | C(C)[Al](CC)CC.[H][H].[H][H].C=CC=C>>C=CC(C)=C.C=CC=C | C[CH2:4][Al]([CH2:1][CH3:2])[CH2:3][CH3:5]>>[CH2:1]=[CH:2][C:3](=[CH2:4])[CH3:5] | C[CH2][Al]([CH2]C)[CH2]C | C=CC(=C)C | null | [Co].[Al].CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Co+2] | C1CCCCC1.[Co] | Miscellaneous | OtherReaction | b4e0efc9cc290a9b30be44680637729e6703a0d33ce2c0e94e1cf7262d59b37b | 8088804b2f510891cc563e9f665e95c30529f26dee02f10a944fab24cca5ce0b | null | C-[CH2;D2;+0:1]-[Al](-[CH2;D2;+0:2]-[CH3;D1;+0:3])-[CH2;D2;+0:4]-[C;D1;H3:5]>>[C;D1;H3:5]-[C;H0;D3;+0:4](=[CH2;D1;+0:1])-[CH;D2;+0:3]=[CH2;D1;+0:2] | null | [] | null | null | null | null | Part of the polymeric solution (195 g) described in Example V was introduced into a 0.5 L Fischer-Porter reactor. The total amount of polymer added to the reactor was 31.4 g which represents 0.540 moles of butadiene unsaturation. The hydrogenation catalyst was prepared by adding 35.1 mL of a 1.7M triethylaluminum solut... | 10.6084/m9.figshare.5104873.v1 | null | null | Vinyl.Vinyl | null | null | null | Other | [Co].[Al].CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Co+2].C1CCCCC1.[Co] | null | null | C[CH2][Al]([CH2]C)[CH2]C>[Co].[Al].CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Co+2].C1CCCCC1.[Co]>C=CC(=C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a3eda3d721a549a6bcd88ad5e8f9a4a3 | C=CC=C>>C=CC=C | C(CCC)[Li].C(CCC)[Li].C=CC=C.C=CC(C)=C.[Na]>>C=CC(C)=C.C=CC=C | [CH2:6]=[CH:7][CH:8]=[CH2:9]>>[CH2:6]=[CH:7][CH:8]=[CH2:9] | C=CC=C | C=CC=C | null | null | O1CCCC1.C1CCCCC1.CCCCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 4 | HOUR | Eleven hundred milliliters of purified pentane was introduced under a nitrogen atmosphere into a two quart glass-bowled pressure reactor. The reactor was equipped with an air driven stirrer, a pressure gauge, a thermometer well, a heat exchange coil, a top surface inlet valve, a dip tube feeder with a valve, a syringe ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O1CCCC1.C1CCCCC1.CCCCC | null | 4 | C=CC=C>O1CCCC1.C1CCCCC1.CCCCC>C=CC=C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-25ff45b66b4f4d2196e608014e91c72c | C=Cc1ccc(C)cc1>>C=Cc1ccc(C)cc1 | C(CCC)[Li].CC1=CC=C(C=C)C=C1.C=CC=C.C=CC=C.CC1=CC=C(C=C)C=C1.C(CCC)[Li]>>CC1=CC=C(C=C)C=C1.C=CC=C | [CH2:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]1>>[CH2:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]1 | C=Cc1ccc(C)cc1 | C=Cc1ccc(C)cc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | 35 | CELSIUS | 3.6 | HOUR | One thousand milliliters of purified pentane and 100 mL of tetrahydrofuran distilled over benzophenone ketyl were introduced under a nitrogen atmosphere into a two quart glass bowled stirred pressure reactor. The reactor was equipped with an air driven stirrer, a pressure gauge, a thermometer well, a heat exchange coil... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | 35 | 3.6 | C=Cc1ccc(C)cc1>>C=Cc1ccc(C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3592964bb411464a9d252afbb2f06a56 | CC(C)(C)OC(=O)N[C@H](CO)C(c1ccccc1)c1ccccc1.FC(F)(F)c1cc(CBr)cc(C(F)(F)F)c1>>CC(C)(C)OC(=O)N[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 | C(C)(C)(C)OC(=O)N[C@H](CO)C(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Na+].FC(C=1C=C(CBr)C=C(C1)C(F)(F)F)(F)F>>C(C)(C)(C)OC(=O)N[C@H](COCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][OH:11])[CH:27]([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.Br[CH2:12][c:13]1[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:... | CC(C)(C)OC(=O)N[C@H](CO)C(c1ccccc1)c1ccccc1.FC(F)(F)c1cc(CBr)cc(C(F)(F)F)c1 | CC(C)(C)OC(=O)N[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 | null | null | O1CCCC1.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc(COCCC(c2ccccc2)c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 16 | HOUR | To a cooled solution (0° C.) of (S)-2-t-butoxycarbonylamino-3,3-diphenylpropan-1-ol (2.04 g, 6.2 mmol, Example 1 g) in tetrahydrofuran (50 ml) and dimethylformamide (10 ml) was added sodium hydride (0.187 g, 80% suspension in oil) over 15 minutes. After an additional 10 minutes 3,5-bis(trifluoromethyl)benzyl bromide (1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.CN(C=O)C | null | 16 | CC(C)(C)OC(=O)N[C@H](CO)C(c1ccccc1)c1ccccc1.FC(F)(F)c1cc(CBr)cc(C(F)(F)F)c1>O1CCCC1.CN(C=O)C>CC(C)(C)OC(=O)N[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2f9111900eb248048af418ff562d0e49 | COC(=O)CBr.N[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1>>COC(=O)CN[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 | N[C@H](COCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(=O)OC>>COC(CN[C@H](COCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][C@H:7]([CH2:8][O:9][CH2:10][c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]1)[CH:25]([c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C@H:7]([CH2:... | COC(=O)CBr.N[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 | COC(=O)CN[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 308780347cfd56717124ea78bf2bc5de380db774d7ce948246e279dfd7d8998b | d2327a8d30a39f085182e5e2f77f5b022ac99c077866b86103acfec639a8f73d | c1ccc(COCCC(c2ccccc2)c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]-[C:7](-[C:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5] | null | [] | null | null | 0.75 | HOUR | To a solution of (S)-2-amino-1-((3,5-bis(trifluoromethyl) phenyl)methyloxy)-3,3-diphenylpropane (8.6 g, Example 1i) and anhydrous K2CO3 (13.0 g)in dimethylformamide (50 ml) was added methyl bromoacetate (4.5 ml). The reaction was stirred at room temperature for 0.75 h then diluted with ethyl acetate (200 ml) and washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 0.75 | COC(=O)CBr.N[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1>CN(C=O)C.C(C)(=O)OCC>COC(=O)CN[C@H](COCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2dbe524b12974d9382613c2ccfb3e4d0 | CSCc1cc(C(C)(C)C)cc(Cl)c1N>>Cc1cc(C(C)(C)C)cc(Cl)c1N | C(C)(C)(C)C1=CC(=C(N)C(=C1)CSC)Cl>>C(C)(C)(C)C1=CC(=C(N)C(=C1)C)Cl | CS[CH2:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([Cl:11])[c:12]1[NH2:13]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([Cl:11])[c:12]1[NH2:13] | CSCc1cc(C(C)(C)C)cc(Cl)c1N | Cc1cc(C(C)(C)C)cc(Cl)c1N | null | [Ni] | CO | Reduction | OtherReaction | 4b57e24218e2409c207dcfe624aba83448b3ad4b3549d9bc7855651565b7e76d | 32a5269109432865a866e9a2b5da238f4471b13dee7daf193dc4e8c41b091706 | c1ccccc1 | C-S-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 4-t-Butyl-2-chloro-6-(methylthiomethyl)aniline (1.3 g) was dissolved in methanol (50 ml) and Raney-nickel (prewashed to pH 7) was added portionwise until t.l.c. indicated all starting material had reacted (ether-hexane, 1:10). The Raney-nickel was removed by filtration through Celite and the filtrate was evaporated. Th... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | null | null | c1ccccc1 | Other | [Ni].CO | null | null | CSCc1cc(C(C)(C)C)cc(Cl)c1N>[Ni].CO>Cc1cc(C(C)(C)C)cc(Cl)c1N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4135a6eeef0c445ba7a7b80232208f57 | Cc1cc(C(C)(C)C)cc(Cl)c1N>>Cc1cc(Cl)cc(C(C)(C)C)c1 | C(C)(C)(C)C1=CC(=C(N)C(=C1)C)Cl.S(O)(O)(=O)=O.N(=O)[O-].[Na+]>>C(C)(C)(C)C=1C=C(C=C(C1)Cl)C | N[c:3]1[c:2]([CH3:1])[cH:12][c:7]([C:8]([CH3:9])([CH3:10])[CH3:11])[cH:6][c:4]1[Cl:5]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12]1 | Cc1cc(C(C)(C)C)cc(Cl)c1N | Cc1cc(Cl)cc(C(C)(C)C)c1 | null | null | C(C)O | Reduction | OtherReaction | a069304de6b46c6d557b2e80c544464adc3bb98001f26c098e87c25f29d552f9 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](-[Cl;D1;H0:6]):[c:7]>>[C;D1;H3:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[Cl;D1;H0:6]):[c:7] | null | [] | null | null | null | null | 4-t-Butyl-2-chloro-6-methylaniline (1.97 g) was dissolved in ethanol (50 ml), sulphuric acid (1.88 ml, conc.) was added dropwise and the resulting blue solution was heated at reflux. Sodium nitrite (1.72 g) was added portionwise over 30 min. The resulting mixture was heated at reflux for a further 30 rain, then cooled ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)O | null | null | Cc1cc(C(C)(C)C)cc(Cl)c1N>C(C)O>Cc1cc(Cl)cc(C(C)(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dac80fb0f36f4b17b2c012191b64c977 | Cc1cc(Cl)cc(C(C)(C)C)c1.O=C1CCC(=O)N1Br>>CC(C)(C)c1cc(Cl)cc(CBr)c1 | C(C)(C)(C)C=1C=C(C=C(C1)Cl)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(C)(C)(C)C=1C=C(CBr)C=C(C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]([CH3:11])[cH:13]1.O=C1CCC(=O)N1[Br:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]([CH2:11][Br:12])[cH:13]1 | Cc1cc(Cl)cc(C(C)(C)C)c1.O=C1CCC(=O)N1Br | CC(C)(C)c1cc(Cl)cc(CBr)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 3-t-Butyl-5-chlorotoluene (5.7 g) was dissolved in carbon tetrachloride (80 ml) and N-bromosuccinimide (5.56 g) was added followed by benzoyl peroxide (750 mg). This mixture was heated at reflux for 6 h. The mixture was cooled, filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1cc(Cl)cc(C(C)(C)C)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CC(C)(C)c1cc(Cl)cc(CBr)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-202a9bbb4dca40d0b986898be9ca314e | COc1cc(C)cc(C)c1.O=C1CCC(=O)N1Br>>COc1cc(C)cc(CBr)c1 | CC=1C=C(C=C(C1)C)OC.BrN1C(CCC1=O)=O>>BrCC=1C=C(C=C(C1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[cH:11]1.O=C1CCC(=O)N1[Br:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH2:9][Br:10])[cH:11]1 | COc1cc(C)cc(C)c1.O=C1CCC(=O)N1Br | COc1cc(C)cc(CBr)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A refluxing solution of 3,5-dimethylanisole (13 g), azoisobutyronitrile (1.6 g) and N-bromosuccinimide (17 g) in carbon tetrachloride (100 ml) was irradiated with light for 6 h. The solution was filtered and the solvent removed in vacuo. The residue was purified by chromatography on silica gel (eluting with 0-5% ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COc1cc(C)cc(C)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COc1cc(C)cc(CBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d84299200b2b4f29be7d2236be2306f3 | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21>>O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | C12C(C3C1C(=O)OC3=O)C(=O)OC2=O.C1=CC(=CC(=C1)N)C(=O)N>>C12C(C3C1C(=O)OC3=O)C(=O)OC2=O.C1=CC(=CC(=C1)N)C(=O)N | [O:11]=[C:12]1[O:13][C:14](=[O:15])[CH:16]2[CH:17]1[CH:18]1[C:19](=[O:20])[O:21][C:22](=[O:23])[CH:24]21>>[O:11]=[C:12]1[O:13][C:14](=[O:15])[CH:16]2[CH:17]1[CH:18]1[C:19](=[O:20])[O:21][C:22](=[O:23])[CH:24]21 | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | null | null | [] | null | null | null | null | 19.22 g (0.098 mol) of CBDA and 12.22 g (0.1 mol) of 3-ABA were reacted in 283 g of NMP at room temperature for 5 hours to prepare a polyamic acid solution. The polymerization reaction proceeded easily and uniformly, and the molecular weights were measured in the same manner as in Preparation Example 1 and as a result,... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1OCC2C1C1COCC21 | null | CN1CCCC1=O | null | null | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21>CN1CCCC1=O>O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d185d75b7569442fb2f6092f3d83f5ac | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21>>O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | C12C(C3C1C(=O)OC3=O)C(=O)OC2=O.C1=CC=C2C=C3C=C(C=CC3=CC2=C1)CCCC(=O)O>>C12C(C3C1C(=O)OC3=O)C(=O)OC2=O.C1=CC=C2C=C3C=C(C=CC3=CC2=C1)CCCC(=O)O | [O:21]=[C:22]1[O:23][C:24](=[O:25])[CH:26]2[CH:27]1[CH:28]1[C:29](=[O:30])[O:31][C:32](=[O:33])[CH:34]21>>[O:21]=[C:22]1[O:23][C:24](=[O:25])[CH:26]2[CH:27]1[CH:28]1[C:29](=[O:30])[O:31][C:32](=[O:33])[CH:34]21 | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 | null | null | [] | null | null | null | null | 19.22 g (0.098 mol) of CBDA, 9.77 g (0.08 mol) of 4-ABA and 5.85 g (0.02 mol) of DADOB were reacted in 197 g of NMP at room temperature for 5 hours to prepare a polyamic acid solution. The polymerization reaction proceeded easily and uniformly, and the molecular weights were measured in the same manner as in Preparatio... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1OCC2C1C1COCC21 | null | CN1CCCC1=O | null | null | O=C1OC(=O)C2C1C1C(=O)OC(=O)C21>CN1CCCC1=O>O=C1OC(=O)C2C1C1C(=O)OC(=O)C21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00c4384d6b5048e79b0f47e3215b50a5 | O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12>>O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12 | C1=C2C(=CC3=C1C(=O)OC3=O)C(=O)OC2=O.C1=CC=C2C=C3C=C(C=CC3=CC2=C1)CCCC(=O)O>>C1=C2C(=CC3=C1C(=O)OC3=O)C(=O)OC2=O.C1=CC=C2C=C3C=C(C=CC3=CC2=C1)CCCC(=O)O | [O:21]=[c:22]1[o:23][c:24](=[O:25])[c:26]2[cH:27][c:28]3[c:29](=[O:30])[o:31][c:32](=[O:33])[c:34]3[cH:35][c:36]12>>[O:21]=[c:22]1[o:23][c:24](=[O:25])[c:26]2[cH:27][c:28]3[c:29](=[O:30])[o:31][c:32](=[O:33])[c:34]3[cH:35][c:36]12 | O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12 | O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12 | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12 | null | null | [] | null | null | null | null | 20.94 g (0.096 mol) of PMDA, 11.00 g (0.09 mol) of 4-ABA and 3.49 g (0.01 mol) of DAHOB were reacted in 201 g of NMP at room temperature for 5 hours to prepare a polyamic acid solution. The polymerization reaction proceeded easily and uniformly, and the molecular weights were measured in the same manner as in Preparati... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1occ2cc3cocc3cc12 | null | CN1CCCC1=O | null | null | O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12>CN1CCCC1=O>O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-817cd11527084050ab0e75f85e5e8e0a | CCCS(=O)(=O)Cl.Cc1ccccc1C(C#N)=C1SC=CC1=NO>>CCCS(=O)(=O)ON=C1C=CSC1=C(C#N)c1ccccc1C | ON=C1C(SC=C1)=C(C#N)C1=C(C=CC=C1)C.C(CC)S(=O)(=O)Cl.O.C(C)N(CC)CC>>C(CC)S(=O)(=O)ON=C1C(SC=C1)=C(C#N)C1=C(C=CC=C1)C | Cl[S:4]([CH2:3][CH2:2][CH3:1])(=[O:5])=[O:6].[OH:7][N:8]=[C:9]1[CH:10]=[CH:11][S:12][C:13]1=[C:14]([C:15]#[N:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[CH3:23]>>[CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[O:7][N:8]=[C:9]1[CH:10]=[CH:11][S:12][C:13]1=[C:14]([C:15]#[N:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[CH3... | CCCS(=O)(=O)Cl.Cc1ccccc1C(C#N)=C1SC=CC1=NO | CCCS(=O)(=O)ON=C1C=CSC1=C(C#N)c1ccccc1C | null | null | O1CCCC1.ClCCl | Acylation | OtherReaction | 50146a9530af828763c7589f586cdd6b32faf532de89bafbd92bbb2e801c1a6a | f6092cbe9db0fc6e43032da5237b29b2d78e210f79dcfa1490f3f662cbf1cda2 | N=C1C=CSC1=Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[C:6]=[C:7]1-[#16:8]-[C:9]=[C:10]-[C:11]-1=[#7:12]-[OH;D1;+0:13]>>[C:6]=[C:7]1-[#16:8]-[C:9]=[C:10]-[C:11]-1=[#7:12]-[O;H0;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5] | 70 | [{"value": 70.0, "product": "C(CC)S(=O)(=O)ON=C1C(SC=C1)=C(C#N)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In 490 g of tetrahydrofuran were dissolved 45 g (0.19 mol) of (3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile in Synthesis Example 1 and 27.0 g (0.19 mol) of commercially available propanesulfonyl chloride. To the solution cooled, 20.6 g (0.20 mol) of triethylamine was added dropwise such that th... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide.Oxime | Sulfonate | null | null | C1=CSCC1.c1ccccc1 | HCl | O1CCCC1.ClCCl | null | 1 | CCCS(=O)(=O)Cl.Cc1ccccc1C(C#N)=C1SC=CC1=NO>O1CCCC1.ClCCl>CCCS(=O)(=O)ON=C1C=CSC1=C(C#N)c1ccccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eea2c1ce513848f792f52b7e8a031284 | Nc1ccccc1N.O=C(O)C(F)(F)C(F)(F)C(=O)O>>FC(F)(c1nc2ccccc2[nH]1)C(F)(F)c1nc2ccccc2[nH]1 | C1(=C(C=CC=C1)N)N.FC(C(C(=O)O)(F)F)(C(=O)O)F>>N1=C(NC2=C1C=CC=C2)C(C(F)(F)C=2NC1=C(N2)C=CC=C1)(F)F | [NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].O=[C:16](O)[C:2]([F:1])([F:3])[C:18]([F:14])([F:15])[C:23](=O)O>>[F:1][C:2]([F:3])([c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[nH:12]1)[C:13]([F:14])([F:15])[c:16]1[n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[nH:24]1 | Nc1ccccc1N.O=C(O)C(F)(F)C(F)(F)C(=O)O | FC(F)(c1nc2ccccc2[nH]1)C(F)(F)c1nc2ccccc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d8bb4423619e5b6e1a1183ec72b61c8c6bd81d8c419173f3499a36a0ba67607d | 6affff663b9fd2961056497c561c38101c041d6e07e5e9d7618df47ef448e4e4 | c1ccc2[nH]c(CCc3nc4ccccc4[nH]3)nc2c1 | O-[C;H0;D3;+0:1](=O)-[C;H0;D4;+0:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:5](-[F;H0;D1;+0:6])(-[F;H0;D1;+0:7])-[C;H0;D3;+0:8](-O)=O.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[F;D1;H0:3]-[C;H0;D4;+0:2](-[F;D1;H0:4])(-[c:15]1:[n;H0;D2;+0:13]:[c:12](:[c:14]):[c:10](:[c:11]):[nH;D2;+0:9]:1)-[C:16](-[F... | null | [] | 160 | CELSIUS | 7 | HOUR | In a 250 mL 35/25 ball joint flask, 1,2-phenylenediamine (5.92 g, 54.7 mmol) was combined with tetrafluorosuccinic acid (5.2 g, 27.36 mmol). Polyphosphoric acid (83 g) was added directly to the solid mixture. The flask was fitted with an air-driven mechanical stirring shaft and heated to 160° C. under a nitrogen purge ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | null | null | 160 | 7 | Nc1ccccc1N.O=C(O)C(F)(F)C(F)(F)C(=O)O>>FC(F)(c1nc2ccccc2[nH]1)C(F)(F)c1nc2ccccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f4736c1983ad4437920881e9356b17a0 | C=CCCCCCCCCC(=O)O.O=C(Cl)C(=O)Cl>>C=CCCCCCCCCC(=O)Cl | C(CCCCCCCCC=C)(=O)O.C(=O)(C(=O)Cl)Cl>>C(CCCCCCCCC=C)(=O)Cl | O[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])=[O:12].O=C(Cl)C(=O)[Cl:13]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[Cl:13] | C=CCCCCCCCCC(=O)O.O=C(Cl)C(=O)Cl | C=CCCCCCCCCC(=O)Cl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | null | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | 100 | [{"value": 100.0, "product": "C(CCCCCCCCC=C)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 10-undecenoic acid (5.055 mL, 25 mmol) in CH2Cl2 (50 mL) was slowly added (COCl)2 (4.364 mL, 50 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure to give 10-undecenoyl chloride (25 mmol). The product was used for the next reaction witho... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | null | HCl | C(Cl)Cl | null | 8 | C=CCCCCCCCCC(=O)O.O=C(Cl)C(=O)Cl>C(Cl)Cl>C=CCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ba0da86e63347cf8a214eba91698af6 | C=CCCCCCCCCC(=O)Cl.CCOC(=O)CC(=O)[O-]>>C=CCCCCCCCCC(=O)CC(=O)OCC | C(CC(=O)[O-])(=O)OCC.[Li]CCCC.C(CCCCCCCCC=C)(=O)Cl>>O=C(CC(=O)OCC)CCCCCCCCC=C | Cl[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])=[O:12].O=C([O-])[CH2:13][C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[CH2:13][C:14](=[O:15])[O:16][CH2:17][CH3:18] | C=CCCCCCCCCC(=O)Cl.CCOC(=O)CC(=O)[O-] | C=CCCCCCCCCC(=O)CC(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 9c255438d8e6adeba9ee52582b8e97af5f85bef382cd416953270ac55bd10486 | 4c7bc8856483317e0c04a17d8cd6aba13cdf5ed9f64b61fe01f230a819039f82 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].O=C(-[O-])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 98.6 | [{"value": 98.6, "product": "O=C(CC(=O)OCC)CCCCCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A stirred solution of monoethyl malonate (5.3 g, 40 mmol) in anhydrous THF (150 mL) was cooled to −78° C. under an argon atmosphere, and n-BuLi (2.5 M, 32 mL, 80 mmol) was added drop-wise via an air-tight syringe. After the addition, the temperature was raised to 0° C., and the stirring was continued for 1 hour. The re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester | Ketone | null | null | null | Other | C1CCOC1 | 0 | 1 | C=CCCCCCCCCC(=O)Cl.CCOC(=O)CC(=O)[O-]>C1CCOC1>C=CCCCCCCCCC(=O)CC(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aee179ab58eb4efda743c97ebbe68cb4 | CCCCCCCCCC(=O)Cl.CCOC(=O)CC(=O)[O-]>>CCCCCCCCCC(=O)CC(=O)OCC | C(CC(=O)[O-])(=O)OCC.[Li]CCCC.C(CCCCCCCCC)(=O)Cl>>O=C(CC(=O)OCC)CCCCCCCCC | O=C(Cl)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[O-][C:10](=[O:11])[CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17] | CCCCCCCCCC(=O)Cl.CCOC(=O)CC(=O)[O-] | CCCCCCCCCC(=O)CC(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | e0a45010daec094b0d5e8e4fbe0fbbb99cf9610754539ead723b25846a3ea8fc | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | null | Cl-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](-[O-])=[O;D1;H0:10]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[CH2;D2;+0:1]-[C:2]-[C:3] | 120.2 | [{"value": 120.2, "product": "O=C(CC(=O)OCC)CCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A stirred solution of monoethyl malonate (1.26 g, 9.6 mmol) in 25 mL anhydrous THF was cooled to −78° C. under an argon atmosphere, and n-BuLi (2.5 M, 8 mL, 20 mmol) was added drop-wise via an air-tight syringe. After the addition, the temperature was raised to 0° C., and the stirring was continued for 1 hour. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | null | null | null | Other | C1CCOC1 | 0 | 1 | CCCCCCCCCC(=O)Cl.CCOC(=O)CC(=O)[O-]>C1CCOC1>CCCCCCCCCC(=O)CC(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bccd1606f68f46538243c62ad1d15035 | CCCCCCCCCC(=O)CC(=O)OCC.OCCO>>CCCCCCCCCC1(CC(=O)OCC)OCCO1 | O=C(CC(=O)OCC)CCCCCCCCC.C(CO)O.CC=1C=CC(=CC1)S(=O)(=O)O>>C1OC(CC(=O)OCC)(CCCCCCCCC)OC1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH2:11][C:12](=[O:13])[O:14][CH2:15][CH3:16])=[O:17].O[CH2:18][CH2:19][OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH2:11][C:12](=[O:13])[O:14][CH2:15][CH3:16])[O:17][CH2:18][CH2:19][O:20]1 | CCCCCCCCCC(=O)CC(=O)OCC.OCCO | CCCCCCCCCC1(CC(=O)OCC)OCCO1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 2baa95c632045e217509d8ec12cda8674252268fe3f8cb44eb2e5ebe0f27c30f | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | C1COCO1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]-[C:12]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C;H0;D4;+0:9]1(-[C:11]-[C:12])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1 | 79 | [{"value": 79.0, "product": "C1OC(CC(=O)OCC)(CCCCCCCCC)OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of ethyl 3-oxododecanoate (1.456 g, ca. 5 mmol), ethylene glycol (2.78 mL, 50 mmol) and a catalytic amount of p-TsOH (95 mg, 0.5 mmol) in benzene (50 mL) was heated to 110° C. under an argon atmosphere overnight. The solvent was removed, and the residue was diluted with 50 mL ethyl acetate. The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | C1COCO1 | HO- | C1=CC=CC=C1 | null | null | CCCCCCCCCC(=O)CC(=O)OCC.OCCO>C1=CC=CC=C1>CCCCCCCCCC1(CC(=O)OCC)OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-082ac3331501484a9c124c4ecaa3c4fc | CCCCCCCCCC1(CC(=O)OCC)OCCO1>>CCCCCCCCCC1(CC(=O)O)OCCO1 | Cl.C1OC(CC(=O)OCC)(CCCCCCCCC)OC1.O[Li].O.C1CCOC1>>C1OC(CC(=O)O)(CCCCCCCCC)OC1 | CC[O:14][C:12]([CH2:11][C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:15][CH2:16][CH2:17][O:18]1)=[O:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH2:11][C:12](=[O:13])[OH:14])[O:15][CH2:16][CH2:17][O:18]1 | CCCCCCCCCC1(CC(=O)OCC)OCCO1 | CCCCCCCCCC1(CC(=O)O)OCCO1 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1COCO1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 81 | [{"value": 81.0, "product": "C1OC(CC(=O)O)(CCCCCCCCC)OC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "C1OC(CC(=O)O)(CCCCCCCCC)OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a 25 mL flask were added ethyl 3,3-ethylenedioxydodecanoate (1.131 g, 3.95 mmol), LiOH.H2O (840 mg, 20 mmol), THF (5 mL), and water (5 mL). The mixture was stirred at room temperature overnight. The solution was acidified by the addition of 1 M HCl (50 mL), and extracted with ethyl acetate (3×50 mL). The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1COCO1 | Other | O | null | 8 | CCCCCCCCCC1(CC(=O)OCC)OCCO1>O>CCCCCCCCCC1(CC(=O)O)OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a6750458ed94fe5aaffc536dc12f1f2 | CCCCCCCCCC1(CC(=O)O)OCCO1.N[C@@H]1CCC[C@H]1O>>CCCCCCCCCC(=O)CC(=O)N[C@@H]1CCC[C@H]1O | C(CCl)Cl.CCN(C(C)C)C(C)C.C1OC(CC(=O)O)(CCCCCCCCC)OC1.Cl.N[C@H]1[C@@H](CCC1)O>>O[C@H]1[C@@H](CCC1)NC(CC(CCCCCCCCC)=O)=O | O[C:13]([CH2:12][C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])OCC[O:11]1)=[O:14].[NH2:15][C@@H:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[OH:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[CH2:12][C:13](=[O:14])[NH:15][C@@H:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[O... | CCCCCCCCCC1(CC(=O)O)OCCO1.N[C@@H]1CCC[C@H]1O | CCCCCCCCCC(=O)CC(=O)N[C@@H]1CCC[C@H]1O | null | CN(C)C=1C=CN=CC1 | CN(C)C=O.C(=O)(C(F)(F)F)O | Acylation | OtherReaction | d0c6aecfd4ea74a053ef63024963609c51e883e82bba95129bbece5aa4e2b368 | e776385d4a3d7d421c579bc9c2d56b9a8877fa86a206c7577e42d62c95dc339e | C1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;H0;D4;+0:4]1(-[C:5]-[C:6])-O-C-C-[O;H0;D2;+0:7]-1.[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:7])-[C:5]-[C:6])-[C:11] | 54 | [{"value": 54.0, "product": "O[C@H]1[C@@H](CCC1)NC(CC(CCCCCCCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 3,3-ethylenedioxydodecanoic acid (55 mg, 0.213 mmol) (Pearson et al., Proc. Natl Acad. Sci. USA 91:197-201 (1994); Bu et al., Synthetic agonists of a Pseudomonas aeruginosa quorum sensing molecule, submitted for publication, which are hereby incorporated by reference in their entirety) and trans-2-amin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Primary amine | Ketone.Secondary amide | C1COCO1 | null | C1CCCC1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O.C(=O)(C(F)(F)F)O | null | 18 | CCCCCCCCCC1(CC(=O)O)OCCO1.N[C@@H]1CCC[C@H]1O>CN(C)C=1C=CN=CC1.CN(C)C=O.C(=O)(C(F)(F)F)O>CCCCCCCCCC(=O)CC(=O)N[C@@H]1CCC[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04d741497f364ad9b516fc50990e2c22 | CCCC(=O)N[C@H]1CCOC1=O>>CCCC(=O)O.N[C@@H]1CCCC[C@H]1O.N[C@@H]1CCC[C@H]1O | C(CCl)Cl.CCCC(=O)N[C@H]1CCOC1=O>>C(CCC)(=O)O.N[C@H]1[C@@H](CCC1)O.N[C@H]1[C@@H](CCCC1)O | [CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:7][C@H:8]1[CH2:9][CH2:10][O:6][C:13]1=[O:14]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[OH:6].[NH2:7][C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[OH:14].[NH2:15][C@@H:16]1[CH2:17][CH2:18][CH2:19][C@H:20]1[OH:21] | CCCC(=O)N[C@H]1CCOC1=O | CCCC(=O)O.N[C@@H]1CCCC[C@H]1O.N[C@@H]1CCC[C@H]1O | null | null | null | Functional Group Addition | Oxidation of amide to carboxylic acid | 542012aeaa708674d041630f8b9df1bea6718662aacc80b9ee6b28e816479fa9 | 5e2ad6f68252a0c4cc0e9b52bcfe117d063b6982056e6c894db512d3b9f8d6f9 | C1CCCC1.C1CCCCC1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[C:6]1-[C:7]-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:10]-1=[O;H0;D1;+0:11]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[OH;D1;+0:9].[NH2;D1;+0:5]-[C:6]1-[C:7]-[CH2;D2;+0:8]-[C:12]-[C:13]-[C@H;D3;+0:10]-1-[OH;D1;+0:11] | null | [] | null | null | null | null | The procedure for the preparation of C4-HSL was used for this series of molecules. The EDC-mediated coupling of butyric acid and trans-2- amino-cyclopentanol or trans-2-amino-cyclohexanol afforded 6 in 66% yield or 8 in 82% yield. 6: IR (KBr) 3284, 2960, 1643, 1567, 1058 cm−1; 1H NMR (500 MHz, CDCl3) δ 0.952 (t, J=7.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Carboxylic acid.Secondary alcohol.Secondary alcohol.Primary amine.Primary amine | C1CCOC1 | C1CCCCC1.C1CCCC1 | C1CCCCC1.C1CCCC1 | Other | null | null | null | CCCC(=O)N[C@H]1CCOC1=O>>CCCC(=O)O.N[C@@H]1CCCC[C@H]1O.N[C@@H]1CCC[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca9f5351d49a4a978457ad82bd1fbd60 | CCCC[C@@H](NC(=O)[C@H](N)CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O.O=C(O)C(F)(F)F>>CC(C)(C)OC(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O | C(=O)(C(F)(F)F)O.N[C@H](CCCNC(N)=N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCNC(N)=N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)NCC(=O)N[C@H](CC1=CC=C(C=C1)O)C(=O)N.C1(=CC=CC=C1)O.C1(=CC=CC=C1)C.C(=O)(C(F)(F)F)O>>N(CC(=O)N[C@H](CC1=CC=C(C=C1)O)C(=O)N)C(=O)OC(C)(C)C | CCCC[C@@H](NC(=O)[C@H](N)CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@@H](C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)[C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][C@H:13]([CH2:14][c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]1)[C:22]([NH2:23])=[O:24])[CH2:3]CC[CH3:4].O=[C:2]([C:1](F)(F)F)[... | CCCC[C@@H](NC(=O)[C@H](N)CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O.O=C(O)C(F)(F)F | CC(C)(C)OC(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | dd722390e0f931a1e91da0a580dd86bb43d4e6a09fcff7959cb32fed079f3dbf | d5fdf5772f396142214745bda546e0d1591f84ba68c45fef9f87b717d7d7541a | c1ccccc1 | C-C-C-C-[C@@H](-N-C(=O)-[C@H](-N)-C-C-C-N-C(-N)=N)-C(=O)-N-[C@H](-C-C-C-C)-C(=O)-N-[C@@H](-[CH2;D2;+0:1]-C-C-[CH3;D1;+0:2])-C(=O)-N-[C@H](-C-C-C-N-C(-N)=N)-C(=O)-N-[C@H](-C-C-C-C)-C(=O)-N-[C@H](-C-C-C-C)-C(=O)-N-[C@H](-C-C-C-C)-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9].F-[C;H0;D4;+0:10](-F)(-... | null | [] | null | null | null | null | The deprotected peptide SF1257-13 (TFA-(D)Arg-(D)Nle-(D)Nle-(D)Nle-(D)Arg-(D)Nle-(D)Nle-(D)Nle-Gly-(D)Tyr-NH2 (SEQ ID NO:1) is made by slowly adding TFA (A×3 l) to a mixture of SF1257-12 (A kg) and phenol (A×0.1 kg) in toluene and THF while maintaining the temperature at ≦18° C. The reaction mixture is allowed to warm ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Primary amine.Primary amine.Primary amine.Secondary amine.Secondary amine | Carbamic ester.Ether.Boc | null | null | c1ccccc1 | HF | C1CCOC1 | null | null | CCCC[C@@H](NC(=O)[C@H](N)CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O.O=C(O)C(F)(F)F>C1CCOC1>CC(C)(C)OC(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89f48428d4e84988964422372e55b7e2 | CCCC[C@H](O)[C@@H](CC1CC1)C(=O)NC1N=C(c2ccccn2)c2ccccc2N(C)C1=O>>CCCCC[C@@H](CC1CC1)C(=O)NC1N=C(c2ccccn2)c2ccccc2N(C)C1=O | C1(CC1)C[C@@H](C(=O)NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)C)=O)[C@H](CCCC)O.NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)C)=O>>O=C([C@@H](CCCCC)CC1CC1)NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)C)=O | O[C@@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C@@H:6]([CH2:7][CH:8]1[CH2:9][CH2:10]1)[C:11](=[O:12])[NH:13][CH:14]1[N:15]=[C:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][n:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[N:29]([CH3:30])[C:31]1=[O:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([CH2:7][CH:8]1[CH2:9][CH2:10]1)[C:11... | CCCC[C@H](O)[C@@H](CC1CC1)C(=O)NC1N=C(c2ccccn2)c2ccccc2N(C)C1=O | CCCCC[C@@H](CC1CC1)C(=O)NC1N=C(c2ccccn2)c2ccccc2N(C)C1=O | null | null | null | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | O=C(CCC1CC1)NC1N=C(c2ccccn2)c2ccccc2NC1=O | O-[C@@H;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C:5])-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[#7:10])-[C:11](=[O;D1;H0:12])-[#7:13]>>[#7:10]-[C:9](-[#7:8]-[C:6](=[O;D1;H0:7])-[C:4](-[C:5])-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:11](=[O;D1;H0:12])-[#7:13] | null | [] | null | null | null | null | (±)-3-(2-(R)-Cyclopropylmethyl-3-(S)-hydroxyl-1-oxoheptyl)amino-1-methyl-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one was made from 1 and 3-amino-1-methyl-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepine-2-one (G. Semple et al Synth. Commun. 1996, 26, 721) according to step 1 in Example 1. MS (ESI): 449 (M... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | C1CC1.c1ccncc1.C1=NCC[NH]c2ccccc21 | Other | null | null | null | CCCC[C@H](O)[C@@H](CC1CC1)C(=O)NC1N=C(c2ccccn2)c2ccccc2N(C)C1=O>>CCCCC[C@@H](CC1CC1)C(=O)NC1N=C(c2ccccn2)c2ccccc2N(C)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65c80db4378345879329b129a789998c | CN(C)CCc1c[nH]c2ccc(N)cc12.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>Cc1c(S(=O)(=O)Nc2ccc3[nH]cc(CCN(C)C)c3c2)sc2ccc(Cl)cc12 | NC=1C=C2C(=CNC2=CC1)CCN(C)C.ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1>>CN(CCC1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)Cl)C)C | [NH2:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][cH:13][c:14]([CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[c:20]2[cH:21]1.Cl[S:4]([c:3]1[c:2]([CH3:1])[c:29]2[c:23]([s:22]1)[cH:24][cH:25][c:26]([Cl:27])[cH:28]2)(=[O:5])=[O:6]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]3[nH:12][cH:13][c:14]([CH2:15][CH2... | CN(C)CCc1c[nH]c2ccc(N)cc12.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | Cc1c(S(=O)(=O)Nc2ccc3[nH]cc(CCN(C)C)c3c2)sc2ccc(Cl)cc12 | null | null | N1=CC=CC=C1 | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1ccc2[nH]ccc2c1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 82 | [{"value": 82.0, "product": "CN(CCC1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)Cl)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "CN(CCC1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)Cl)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of 3.05 g (15 mMol) of 5-amino-3-(2-dimethylaminoethyl)-1H-indol in 100 ml of pyridine is added dropwise at ambient temperature a solution of 4.21 g (15 mMol) of 5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride in 20 ml of pyridine. The reaction mixture is stirred at ambient temperature for 20 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2[nH]ccc2c1.c1ccc2sccc2c1 | HCl | N1=CC=CC=C1 | null | 20 | CN(C)CCc1c[nH]c2ccc(N)cc12.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>N1=CC=CC=C1>Cc1c(S(=O)(=O)Nc2ccc3[nH]cc(CCN(C)C)c3c2)sc2ccc(Cl)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da28e3f72905445186f85e1905136ebe | CCI.CCN(CC)CCc1c[nH]c2ccc(NS(=O)(=O)c3ccc4ccccc4c3)cc12>>CCN(CC)CCc1c[nH]c2ccc(N(CC)S(=O)(=O)c3ccc4ccccc4c3)cc12 | O.C(C)N(CCC1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC2=CC=CC=C2C=C1)CC.CC(C)([O-])C.[K+].C(C)I>>C(C)N(CCC1=CNC2=CC=C(C=C12)N(S(=O)(=O)C1=CC2=CC=CC=C2C=C1)CC)CC | I[CH2:16][CH3:17].[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][c:8]1[cH:9][nH:10][c:11]2[cH:12][cH:13][c:14]([NH:15][S:18](=[O:19])(=[O:20])[c:21]3[cH:22][cH:23][c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]4[cH:30]3)[cH:31][c:32]12>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][c:8]1[cH:9][nH:10][c:11]2[cH:12][cH:... | CCI.CCN(CC)CCc1c[nH]c2ccc(NS(=O)(=O)c3ccc4ccccc4c3)cc12 | CCN(CC)CCc1c[nH]c2ccc(N(CC)S(=O)(=O)c3ccc4ccccc4c3)cc12 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(Nc1ccc2[nH]ccc2c1)c1ccc2ccccc2c1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[#16:4](=[O;D1;H0:5])(-[c:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[#16:4](=[O;D1;H0:3])(=[O;D1;H0:5])-[c:6] | null | [] | null | null | 30 | MINUTE | To a mixture of 285 mg (0.7 mMol) of N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide (example 17) and 80 mg (0.7 mMol) of potassium t-butoxide in 3 ml of DMSO are stirred for 30 minutes at ambient temperature. Then are added 105 mg (0.7 mMol) of ethyl iodide and left with stirring for 3 hours. Water... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccc2[nH]ccc2c1.c1ccc2ccccc2c1 | HI | CS(=O)C | null | 0.5 | CCI.CCN(CC)CCc1c[nH]c2ccc(NS(=O)(=O)c3ccc4ccccc4c3)cc12>CS(=O)C>CCN(CC)CCc1c[nH]c2ccc(N(CC)S(=O)(=O)c3ccc4ccccc4c3)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2ceadb7003543839098c55a9adcf662 | CN1CCC(=O)CC1.O=S(=O)(Nc1ccc2[nH]ccc2c1)c1cccc2ccccc12>>CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 | CN1CCC(CC1)=O.C[O-].[Na+].N1C=CC2=CC(=CC=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12>>CN1CCC(=CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12 | O=[C:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:30][CH2:29]1.[cH:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([NH:13][S:14](=[O:15])(=[O:16])[c:17]3[cH:18][cH:19][cH:20][c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][c:28]12>>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([c:6]2[cH:7][nH:8][c:9]3[cH:10][cH:11][c:12]([NH:13][S:14](=[O:15])... | CN1CCC(=O)CC1.O=S(=O)(Nc1ccc2[nH]ccc2c1)c1cccc2ccccc12 | CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 | null | null | CO | C-C Coupling | piperidine_indole | 2c09067bd257df167078887e4090fe0d7bc8a234e11e68ee424f29322f615f2e | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=S(=O)(Nc1ccc2[nH]cc(C3=CCNCC3)c2c1)c1cccc2ccccc12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C;D1;H3:5])-[C:6]-[CH2;D2;+0:7]-1.[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[#7:4]1-[C:3]-[C:2]-[C;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:2:[c:14])=[CH;D2;+0:7]-[C:6]-1 | 52 | [{"value": 52.0, "product": "CN1CCC(=CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.0, "product": "CN1CCC(=CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 712 mg (13.2 mMol) of sodium methoxide in 100 ml of methanol are added 850 mg (2.64 mMol) of N-[1H-indol-5-yl]naphthalene-1-sulphonamide followed by 596 mg (5.28 mMol) of 1-methyl-4-piperidone and the resulting solution is heated to reflux for 48 hours. The reaction mixture is concentrated at reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CC[NH]CC1.c1ccc2[nH]ccc2c1 | C1=CC[NH]CC1.c1ccc2[nH]ccc2c1 | C1=CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2ccccc2c1 | HO- | CO | null | null | CN1CCC(=O)CC1.O=S(=O)(Nc1ccc2[nH]ccc2c1)c1cccc2ccccc12>CO>CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89760789d5364662a7531ad6c3dacc80 | CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1>>CN1CCC(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 | CN1CCC(=CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12.[H][H]>>CN1CCC(CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([c:6]2[cH:7][nH:8][c:9]3[cH:10][cH:11][c:12]([NH:13][S:14](=[O:15])(=[O:16])[c:17]4[cH:18][cH:19][cH:20][c:21]5[cH:22][cH:23][cH:24][cH:25][c:26]45)[cH:27][c:28]23)[CH2:29][CH2:30]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][nH:8][c:9]3[cH:10][cH:11][c:12]([NH:13][S:14](=[O:15])(=[... | CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 | CN1CCC(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 | null | [Pd] | CO.C(C)OCC | Reduction | Hydrogenation (double to single) | 641ee5df237f030873b7ef4c8f313c4da4e38b634b6176a5872cc6f99e79a814 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=S(=O)(Nc1ccc2[nH]cc(C3CCNCC3)c2c1)c1cccc2ccccc12 | [C;D1;H3:1]-[#7:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2)=[CH;D2;+0:11]-[C:12]-1>>[C;D1;H3:1]-[#7:2]1-[C:3]-[C:4]-[CH;D3;+0:5](-[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2)-[CH2;D2;+0:11]-[C:12]-1 | 65 | [{"value": 65.0, "product": "CN1CCC(CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.8, "product": "CN1CCC(CC1)C1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 417 mg (1 mMol) of N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide in 50 ml of methanol are added 100 mg of 5% palladium on carbon. The mixture is hydrogenated at ambient temperature at an initial hydrogen pressure of 3 atmospheres for 20 hours. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2ccccc2c1 | null | [Pd].CO.C(C)OCC | null | null | CN1CC=C(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1>[Pd].CO.C(C)OCC>CN1CCC(c2c[nH]c3ccc(NS(=O)(=O)c4cccc5ccccc45)cc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbe38b21f1884409ba46563e39eeffe4 | Cl>>Cl | Cl.C(C)N(CCC1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12)CC>>Cl.C(C)N(CCC1=CNC2=CC=C(C=C12)NS(=O)(=O)C1=CC=CC2=CC=CC=C12)CC | [ClH:31]>>[ClH:31] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 1.05 g (2.5 mMol) of N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-1-sulphonamide (example 2) are dissolved in 10 ml of ethanol and 0.6 ml are added of a 4.2 N solution of hydrochloric acid in ethanol. It is allowed to crystallise at ambient temperature. N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-1-sul... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8283582e54f4892a69fd5f201a4c969 | Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1>>Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1 | C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O.Cl>>C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O.Cl | [NH2:2][c:3]1[cH:4][cH:5][n:6]([C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@@H:14]2[OH:15])[c:16](=[O:17])[n:18]1>>[NH2:2][c:3]1[cH:4][cH:5][n:6]([C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@@H:14]2[OH:15])[c:16](=[O:17])[n:18]1 | Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1 | Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1ncccn1[C@H]1CCCO1 | null | 96.3 | [{"value": 96.0, "product": "C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O.Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 2 | CELSIUS | null | null | A 5 L, 3-neck flask equipped with an overhead stirrer and thermocouple was charged with cytarabine (500 g, 2.06 mol) and methanol (2.0 L). The suspension was cooled to 2° C. HCl gas was bubbled in, giving a very thick mixture and an exotherm to 25° C. The suspension was diluted with methanol (0.5 L) to facilitate stirr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cncnc1.C1CCOC1 | null | CO | 2 | null | Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1>CO>Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a09d052e34b42498da108bf302c1b78 | CC(=O)CCC(C)=O.Nc1ccc(Br)cn1>>Cc1ccc(C)n1-c1ccc(Br)cn1 | NC1=NC=C(C=C1)Br.CC(CCC(C)=O)=O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C=CC(=NC1)N1C(=CC=C1C)C | O=[C:2]([CH3:1])[CH2:3][CH2:4][C:5](=O)[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]1 | CC(=O)CCC(C)=O.Nc1ccc(Br)cn1 | Cc1ccc(C)n1-c1ccc(Br)cn1 | null | null | CCCCCCC | Aromatic Heterocycle Formation | Paal-Knorr pyrrole synthesis | 0dbcc2550964c10d57651fd35699c19ea2fb10549389c3d3c9cfc6181b9e43ad | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1ccc(-n2cccc2)nc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[NH2;D1;+0:7]-[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[c:11]:[c:12]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[C;D1;H3:6]):[n;H0;D3;+0:7]:1-[c;H0;D3;+0:8](:[#7;a:9]:[c:10]):[c:11]:[c:12] | 80 | [{"value": 80.0, "product": "BrC=1C=CC(=NC1)N1C(=CC=C1C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | 2-Amino-5-bromopyridine (6.0 Kg, 34.7 mol), 2,5-hexanedione (4.35 Kg, 38.2 mol) and p-toluenesulfonic acid (12 g) were dissolved in heptane (36 L) and refluxed under Dean Stark conditions overnight. The equipment was set for distillation and heptane (18 L) was removed by distillation. The mixture was cooled to 20° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1ccc[nH]1 | c1ccc[nH]1.c1ccncc1 | HO- | CCCCCCC | 20 | 2 | CC(=O)CCC(C)=O.Nc1ccc(Br)cn1>CCCCCCC>Cc1ccc(C)n1-c1ccc(Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3942f2c63344068ae32f7ebd7a47258 | CON(C)C(=O)CCl.Cc1ccc(C)n1-c1ccc(Br)cn1>>Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1 | Cl.ClCC(=O)N(C)OC.BrC=1C=CC(=NC1)N1C(=CC=C1C)C.C(CCC)[Li]>>ClCC(=O)C=1C=NC(=CC1)N1C(=CC=C1C)C | CON(C)[C:12](=[O:13])[CH2:14][Cl:15].Br[c:11]1[cH:10][cH:9][c:8](-[n:7]2[c:2]([CH3:1])[cH:3][cH:4][c:5]2[CH3:6])[n:17][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH2:14][Cl:15])[cH:16][n:17]1 | CON(C)C(=O)CCl.Cc1ccc(C)n1-c1ccc(Br)cn1 | Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1 | null | null | O.CC(C)(C)OC | C-C Coupling | OtherReaction | aeedefb516da447a7938cf0e8e86abd66c9a6aa8bd6688105f56ff15f4aef307 | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | c1ccc(-n2cccc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.C-O-N(-C)-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[Cl;D1;H0:10]>>[Cl;D1;H0:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 78.8 | [{"value": 78.8, "product": "ClCC(=O)C=1C=NC(=CC1)N1C(=CC=C1C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine (1.00 Kg 3.98 mol) in TBME (7.5 L) was cooled to −70° C. n-Butyl lithium (2.5N in hexane; 1.73 L, 4.32 mol) was added drop-wise over 1 hour maintaining the temperature between −74° C. and −69° C. The mixture was then stirred at a temperature between −74° C. and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccncc1 | c1ccncc1 | c1ccc[nH]1.c1ccncc1 | HBr | O.CC(C)(C)OC | null | 0.25 | CON(C)C(=O)CCl.Cc1ccc(C)n1-c1ccc(Br)cn1>O.CC(C)(C)OC>Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8995507e24b4c86a0deb264fbb402c3 | Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1>>Cc1ccc(C)n1-c1ccc(C2CO2)cn1 | ClCC(=O)C=1C=NC(=CC1)N1C(=CC=C1C)C.O.[BH4-].[Na+]>>CC=1N(C(=CC1)C)C1=NC=C(C=C1)C1OC1 | Cl[CH2:13][C:12]([c:11]1[cH:10][cH:9][c:8](-[n:7]2[c:2]([CH3:1])[cH:3][cH:4][c:5]2[CH3:6])[n:16][cH:15]1)=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][c:11]([CH:12]2[CH2:13][O:14]2)[cH:15][n:16]1 | Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1 | Cc1ccc(C)n1-c1ccc(C2CO2)cn1 | null | null | O1CCCC1.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 040b28e8687bbf29652da8799a10f1a268145019b9a625d75da3ba77970763f1 | 98d62a2f88bda9a16db724874a7a21c7201c15ae486e75d3477ada88c887a7ad | c1ccn(-c2ccc(C3CO3)cn2)c1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]>>[c:5]:[c:4](-[CH;D3;+0:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-1):[c:6]:[#7;a:7]:[c:8] | 98 | [{"value": 98.0, "product": "CC=1N(C(=CC1)C)C1=NC=C(C=C1)C1OC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Water (1.08 Kg) was added dropwise to a suspension of sodium borohydride (0.17 Kg, 4.36 mol) in 1,4-dioxane (6.49 L) at 16° C. and the resulting solution stirred at room temperature. A solution of 2-chloro-1-[6-(2,5-dimethylpyrrol-1-yl)pyridin-3-yl]ethanone (1.08 Kg, 4.35 mol) in tetrahydrofuran (2.16 L) was added over... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ether | null | C1CO1 | c1ccc[nH]1.c1ccncc1.C1CO1 | Other | O1CCCC1.O1CCOCC1 | null | 8 | Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1>O1CCCC1.O1CCOCC1>Cc1ccc(C)n1-c1ccc(C2CO2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b710966a6568404d83990214ede4ffd5 | CCC=O.C[C@H](N)CO.Cc1ccc(C)n1-c1ccc(C2CO2)cn1>>CCCN(CC(O)c1ccc(-n2c(C)ccc2C)nc1)[C@@H](C)CO | C(CC)=O.CC=1N(C(=CC1)C)C1=NC=C(C=C1)C1OC1.N[C@H](CO)C.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN([C@H](CO)C)CCC)O | O=[CH:3][CH2:2][CH3:1].[NH2:4][C@@H:21]([CH3:22])[CH2:23][OH:24].[CH2:5]1[CH:6]([c:8]2[cH:9][cH:10][c:11](-[n:12]3[c:13]([CH3:14])[cH:15][cH:16][c:17]3[CH3:18])[n:19][cH:20]2)[O:7]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH:6]([OH:7])[c:8]1[cH:9][cH:10][c:11](-[n:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]2[CH3:18])[n:19][cH... | CCC=O.C[C@H](N)CO.Cc1ccc(C)n1-c1ccc(C2CO2)cn1 | CCCN(CC(O)c1ccc(-n2c(C)ccc2C)nc1)[C@@H](C)CO | null | null | O.C1(=CC=CC=C1)C.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a87f24ce5b1e3fe1bd7467517d104e8f030c516efb839848b90fcd8dfb3aea84 | 7f6cbb1838c3a51c1ccf9cb420b73a7085d2d86eff0ad9e99407ef77638b78c4 | c1ccc(-n2cccc2)nc1 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[#7;a:4]:[c:5]:[c:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1.[C:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[#7;a:4]:[c:5]:[c:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[N;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:11](-[C:10])-[C;D1;H3:12] | 89 | [{"value": 89.0, "product": "CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN([C@H](CO)C)CCC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2-(2,5-dimethylpyrrol-1-yl)-5-oxiranylpyridine (0.65 Kg, 3.04 mol), (S)-(+)-2-amino-1-propanol (0.30 Kg, 3.95 mol) in toluene (6.50 L) was heated to reflux overnight. The reaction mixture was cooled to room temperature and DCM (6.5 L) and water (1.30 L) were added and the phases allowed to separate. Sodium... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccncc1.c1ccc[nH]1 | Other | O.C1(=CC=CC=C1)C.C(Cl)Cl | null | 1 | CCC=O.C[C@H](N)CO.Cc1ccc(C)n1-c1ccc(C2CO2)cn1>O.C1(=CC=CC=C1)C.C(Cl)Cl>CCCN(CC(O)c1ccc(-n2c(C)ccc2C)nc1)[C@@H](C)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-805059097d6842fea67f3471bb31e042 | C[C@H](N)CO.Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1>>Cc1ccc(C)n1-c1ccc(C(O)CN[C@@H](C)CO)cn1 | C(Cl)Cl.[BH4-].[Na+].ClCC(=O)C=1C=NC(=CC1)N1C(=CC=C1C)C.N[C@H](CO)C>>CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN[C@H](CO)C)O | [NH2:15][C@@H:16]([CH3:17])[CH2:18][OH:19].Cl[CH2:14][C:12]([c:11]1[cH:10][cH:9][c:8](-[n:7]2[c:2]([CH3:1])[cH:3][cH:4][c:5]2[CH3:6])[n:21][cH:20]1)=[O:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[cH:9][cH:10][c:11]([CH:12]([OH:13])[CH2:14][NH:15][C@@H:16]([CH3:17])[CH2:18][OH:19])[cH:20][n:21]1 | C[C@H](N)CO.Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1 | Cc1ccc(C)n1-c1ccc(C(O)CN[C@@H](C)CO)cn1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 1c7faa1e6cb9e060b7e89d591b967fa7b694f333cb5a775c79fc9a9f84d0a6be | d0da6e2f6de7d14ed85c2c5a966c155ca30e7a0510b1db3dd27bbc45bfc08d34 | c1ccc(-n2cccc2)nc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[C:9]-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12]>>[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | 65 | [{"value": 65.0, "product": "CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN[C@H](CO)C)O", "details": "PERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 8 | HOUR | Water (15.0 L) was added to a suspension of sodium borohydride (4.11 Kg, 109 mol) in tetrahydrofuran (140 L) at 15° C. and the resulting solution stirred at 15° C. A solution of 2-chloro-1-[6-(2,5-dimethylpyrrol-1-yl)pyridin-3-yl]ethanone (30.0 Kg, 120.6 mol) in tetrahydrofuran (100 L) and water (15 L) was added over 4... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | Secondary alcohol.Secondary amine | null | null | c1ccc[nH]1.c1ccncc1 | Other | O1CCCC1.O | 15 | 8 | C[C@H](N)CO.Cc1ccc(C)n1-c1ccc(C(=O)CCl)cn1>O1CCCC1.O>Cc1ccc(C)n1-c1ccc(C(O)CN[C@@H](C)CO)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-930a6bc0fb78413f84726922de9c8a63 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.Cc1ccc(C)n1-c1ccc(C(O)CN[C@@H](C)CO)cn1>>CCCN(CC(O)c1ccc(-n2c(C)ccc2C)nc1)[C@@H](C)CO | CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN[C@H](CO)C)O.C(Cl)Cl.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(Cl)Cl.C(Cl)Cl>>CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN([C@H](CO)C)CCC)O | CC(=O)O[BH-](OC(C)=O)OC(=O)[CH3:1].[NH:4]([CH2:5][CH:6]([OH:7])[c:8]1[cH:9][cH:10][c:11](-[n:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]2[CH3:18])[n:19][cH:20]1)[C@@H:21]([CH3:22])[CH2:23][OH:24]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH:6]([OH:7])[c:8]1[cH:9][cH:10][c:11](-[n:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]2[CH3:18... | CC(=O)O[BH-](OC(C)=O)OC(C)=O.Cc1ccc(C)n1-c1ccc(C(O)CN[C@@H](C)CO)cn1 | CCCN(CC(O)c1ccc(-n2c(C)ccc2C)nc1)[C@@H](C)CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(-n2cccc2)nc1 | C-C(=O)-O-[BH-](-O-C(-C)=O)-O-C(=O)-[CH3;D1;+0:1].[C:2]-[C:3](-[C;D1;H3:4])-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:2]-[C:3](-[C;D1;H3:4])-[N;H0;D3;+0:5](-[C:8]-[C:9]-[CH3;D1;+0:1])-[C:6]-[C:7] | 100 | [{"value": 100.0, "product": "CC=1N(C(=CC1)C)C1=CC=C(C=N1)C(CN([C@H](CO)C)CCC)O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | Propioanaldehyde (5.02 Kg, 86.4 mol) was added over 10 minutes to a solution of (2S)-2-[{(RS)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-2-hydroxyethyl} amino]propan-1-ol (22.7 Kg, 78.6 mol) in DCM (123 L) at 20° C. The resulting solution was stirred at 20° C. for 2 hours and then allowed to settle before adding i... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccncc1.c1ccc[nH]1 | HO-.B | null | 20 | 2 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.Cc1ccc(C)n1-c1ccc(C(O)CN[C@@H](C)CO)cn1>>CCCN(CC(O)c1ccc(-n2c(C)ccc2C)nc1)[C@@H](C)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b3178f60b4774d0b9e3efc65f3fe44ff | COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12>>COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)CCC[C@@H]12 | C[C@]12CC[C@@H]3C4=CC(=C(C=C4CC[C@H]3[C@@H]1CCC2=O)O)OC.Cl.O.NN.[OH-].[K+].C[C@]12CC[C@@H]3C4=CC(=C(C=C4CC[C@H]3[C@@H]1CCC2=O)O)OC>>COC=1C(=CC=2CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3C2C1)O | O=[C:18]1[C@@:16]2([CH3:17])[CH2:15][CH2:14][C@@H:13]3[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:8]([OH:9])[cH:7][c:6]4[CH2:10][CH2:11][C@H:12]3[C@@H:21]2[CH2:20][CH2:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[CH2:10][CH2:11][C@@H:12]1[C@@H:13]2[CH2:14][CH2:15][C@:16]2([CH3:17])[CH2:18][CH2:19][CH2:20][C@@H:2... | COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)CCC[C@@H]12 | null | null | C(CCC)O.C(CO)O | Reduction | OtherReaction | fd58e1827afbea1124957b3c36988b8bd802de991df6da1a5316964c3ec7a550 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc2c(c1)CC[C@@H]1[C@@H]2CCC2CCC[C@H]21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1(-[C;D1;H3:6])-[C:7]>>[C:7]-[C:5]1(-[C;D1;H3:6])-[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-1 | 72 | [{"value": 72.0, "product": "COC=1C(=CC=2CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3C2C1)O", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | 2-Methoxyestrone (Scheme 1, Compound 4) (450 mg, 1.5 mmol) was suspended in ethylene glycol (10 mL) and n-butanol (2 mL). Hydrazine hydrate (0.145 mL, 3 mmol) was added and the mixture was heated to 130° C. for 1 h. The reaction was cooled to 70° C., KOH (253 mg, 4.5 mmol) was added, then the reaction was heated at 200... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | Other | C(CCC)O.C(CO)O | 130 | null | COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12>C(CCC)O.C(CO)O>COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)CCC[C@@H]12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da81b91a196a42238b3e7f89d253e55f | CN(C)C=O.COc1cc2c(cc1OS(=O)(=O)C(F)(F)F)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.C[Si](C)(C)N[Si](C)(C)C>>COc1cc2c(cc1C(N)=O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | FC(F)(F)S(=O)(=O)OC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1OC)=O.FC(F)(F)S(=O)(=O)OC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1OC)=O.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C[Si](N[Si](C)(C)C)(C)C.CN(C=O)C>>COC=1C(=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C1)=O)C(=O)N | CN(C)[CH:9]=[O:11].O=S(=O)(O[c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[CH2:12][CH2:13][C@@H:14]1[C@@H:15]2[CH2:16][CH2:17][C@:18]2([CH3:19])[C:20](=[O:21])[CH2:22][CH2:23][C@@H:24]12)C(F)(F)F.C[Si](C)(C)[NH:10][Si](C)(C)C>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[C:9]([NH2:10])=[O:11])[CH2:12][CH2:13][... | CN(C)C=O.COc1cc2c(cc1OS(=O)(=O)C(F)(F)F)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.C[Si](C)(C)N[Si](C)(C)C | COc1cc2c(cc1C(N)=O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 | null | [Pd](Cl)Cl | null | Acylation | OtherReaction | 28dfc2095901125ca6aeb494c4f6700f9e5669474dc40f8f7f307fdeb24c9e0f | 20828c3ba691e9e648802e3d84cb3d844d05384246e1426a16d21d50c98982f9 | O=C1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].C-[Si](-C)(-C)-[NH;D2;+0:3]-[Si](-C)(-C)-C.F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[#8:8]):[c:9]>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[C;H0;D3;+0:1](-[NH2;D1;+0:3])=[O;D1;H0:2]):[c:5]:[c:6] | 44 | [{"value": 44.0, "product": "COC=1C(=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C1)=O)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 5 | MINUTE | A 1-L 3 neck round-bottomed flask equipped with an overhead stirrer, reflux condenser, nitrogen inlet and thermocouple, was charged with 2-methoxy-17-oxoestra-1,3,5(10)-triene-3-yl(trifluoromethyl)sulfonate (Scheme 5, Compound 42) (15 g, 34.7 mmol), 1,3-bis(diphenylphosphino)propane (1.54 g, 3.73 mmol), palladium (II) ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tertiary amide.Secondary amine.Silyl protective group.Silyl protective group | Primary amide | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | TfOH.HO- | [Pd](Cl)Cl | 110 | 0.083333 | CN(C)C=O.COc1cc2c(cc1OS(=O)(=O)C(F)(F)F)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.C[Si](C)(C)N[Si](C)(C)C>[Pd](Cl)Cl>COc1cc2c(cc1C(N)=O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-409b30f7236646f697e501d779c099f8 | C=C1CC[C@H]2[C@@H]3CCc4cc(OS(=O)(=O)C(F)(F)F)c(OC)cc4[C@H]3CC[C@]12C.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C>>C=C1CC[C@H]2[C@@H]3CCc4cc(C(N)=O)c(OC)cc4[C@H]3CC[C@]12C | FC(F)(F)S(=O)(=O)OC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1OC)=C.FC(F)(F)S(=O)(=O)OC1=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C=C1OC)=C.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C[Si](N[Si](C)(C)C)(C)C.CN(C=O)C>>COC=1C(=CC=2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3C2C1)=C)C(=O)N | O=S(=O)(O[c:11]1[cH:10][c:9]2[c:19]([cH:18][c:15]1[O:16][CH3:17])[C@@H:20]1[C@H:6]([C@@H:5]3[CH2:4][CH2:3][C:2](=[CH2:1])[C@@:23]3([CH3:24])[CH2:22][CH2:21]1)[CH2:7][CH2:8]2)C(F)(F)F.CN(C)[CH:12]=[O:14].C[Si](C)(C)[NH:13][Si](C)(C)C>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]3[CH2:7][CH2:8][c:9]4[cH:10][c:11]([C:12](... | C=C1CC[C@H]2[C@@H]3CCc4cc(OS(=O)(=O)C(F)(F)F)c(OC)cc4[C@H]3CC[C@]12C.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C | C=C1CC[C@H]2[C@@H]3CCc4cc(C(N)=O)c(OC)cc4[C@H]3CC[C@]12C | null | [Pd](Cl)Cl | null | Acylation | OtherReaction | 28dfc2095901125ca6aeb494c4f6700f9e5669474dc40f8f7f307fdeb24c9e0f | 20828c3ba691e9e648802e3d84cb3d844d05384246e1426a16d21d50c98982f9 | C=C1CC[C@@H]2C1CC[C@@H]1c3ccccc3CC[C@H]12 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].C-[Si](-C)(-C)-[NH;D2;+0:3]-[Si](-C)(-C)-C.F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[#8:8]):[c:9]>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[C;H0;D3;+0:1](-[NH2;D1;+0:3])=[O;D1;H0:2]):[c:5]:[c:6] | null | [] | 100 | CELSIUS | 18 | HOUR | A 250 mL three-necked flask equipped with an overhead stirrer, thermocouple, and nitrogen inlet, was charged with 2-Methoxy-17-methyleneestra-1,3,5(110)-trien-3-yl(trifluoromethyl)-sulfonate (Scheme 5, Compound 48) (20.0 g, 46.5 mmol), palladium (II) chloride (0.41 g, 2.3 mmol), 1,3-bis(diphenylphosphino)propane (1.9 g... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tertiary amide.Secondary amine.Silyl protective group.Silyl protective group | Primary amide | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | c1ccc2c(c1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@H]21 | TfOH.HO- | [Pd](Cl)Cl | 100 | 18 | C=C1CC[C@H]2[C@@H]3CCc4cc(OS(=O)(=O)C(F)(F)F)c(OC)cc4[C@H]3CC[C@]12C.CN(C)C=O.C[Si](C)(C)N[Si](C)(C)C>[Pd](Cl)Cl>C=C1CC[C@H]2[C@@H]3CCc4cc(C(N)=O)c(OC)cc4[C@H]3CC[C@]12C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7607adb8172842e19e814c4670b1e131 | CC(=O)OC(C)=O.NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12>>CC(=O)NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 | C(=O)(O)[O-].[Na+].Cl.ClC=1N=C2SC=CN2C1S(=O)(=O)N1C=C(C2=CC=CC=C12)CCN.C(C)N(CC)CC.C(C)(=O)OC(C)=O>>ClC=1N=C2SC=CN2C1S(=O)(=O)N1C=C(C2=CC=CC=C12)CCNC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][CH2:6][c:7]1[cH:8][n:9]([S:10](=[O:11])(=[O:12])[c:13]2[c:14]([Cl:15])[n:16][c:17]3[s:18][cH:19][cH:20][n:21]23)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][c:7]1[cH:8][n:9]([S:10](=[O:11])(=[O:12])[c:13]2[c:14]([Cl:15])[n:16][c:17]3[s:... | CC(=O)OC(C)=O.NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 | CC(=O)NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=S(=O)(c1cnc2sccn12)n1ccc2ccccc21 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 92 | [{"value": 92.0, "product": "ClC=1N=C2SC=CN2C1S(=O)(=O)N1C=C(C2=CC=CC=C12)CCNC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A stirred mixture of 2-{1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}ethylamine hydrochloride, 417 mg, 1.00 mmol) in dichloromethane and triethylamine (0.40 mL, 3.0 mmol) is treated with catalytic 4-dimethylaminopyridine (DMAP) (˜5 mg) at room temperature under nitrogen. The heterogeneous mixture... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1cn2ccsc2n1.c1c[nH]c2ccccc12 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 16 | CC(=O)OC(C)=O.NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12>CN(C1=CC=NC=C1)C.ClCCl>CC(=O)NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67b6ab2bb49b4b18a905c4f867c281dc | O=C(O)Cc1c[nH]c2ccccc12.O=S(=O)(Cl)c1c(Cl)nc2sccn12>>O=C(O)Cc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 | C(CCC)[Li].N1C=C(C2=CC=CC=C12)CC(=O)O.ClC=1N=C2SC=CN2C1S(=O)(=O)Cl>>ClC=1N=C2SC=CN2C1S(=O)(=O)N1C=C(C2=CC=CC=C12)CC(=O)O | [O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][nH:7][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12.Cl[S:8](=[O:9])(=[O:10])[c:11]1[c:12]([Cl:13])[n:14][c:15]2[s:16][cH:17][cH:18][n:19]12>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][n:7]([S:8](=[O:9])(=[O:10])[c:11]2[c:12]([Cl:13])[n:14][c:15]3[s:16][cH:17][cH:18][n:19]23)[c:20]2[cH:21... | O=C(O)Cc1c[nH]c2ccccc12.O=S(=O)(Cl)c1c(Cl)nc2sccn12 | O=C(O)Cc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 | null | null | C1CCOC1 | Acylation | OtherReaction | 95ce265d6113e7bac468269631ca11b794a98d7e0e0f7d7a9efc825210a64f28 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cnc2sccn12)n1ccc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#7;a:5]2:[c:6]:[c:7]:[#16;a:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[Cl;D1;H0:12].[c:13]:[c:14]1:[c:15]:[c:16]:[c:17]:[nH;D2;+0:18]:1>>[Cl;D1;H0:12]-[c:11]1:[#7;a:10]:[c:9]2:[#16;a:8]:[c:7]:[c:6]:[#7;a:5]:2:[c:4]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[n;H0;D3;+0:18]1:[... | null | [] | null | null | 1 | HOUR | A stirred solution of 3-indolylacetic acid (175 mg, 1.00 mmol) in THF is cooled to −78° C. under nitrogen and treated portionwise with 2.5 M n-butyllithium in hexanes (0.84 mL, 2.10 mmol) over a 10 min. period. After 1 h at −78° C., the reaction mixture is treated with (6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1cn2ccsc2n1.c1c[nH]c2ccccc12 | HCl | C1CCOC1 | null | 1 | O=C(O)Cc1c[nH]c2ccccc12.O=S(=O)(Cl)c1c(Cl)nc2sccn12>C1CCOC1>O=C(O)Cc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9adc3242043549e2b147b75100f9d183 | COC(=O)C1OC(OC(=O)NCCc2cn(S(=O)(=O)c3c(Cl)nc4sccn34)c3ccccc23)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O>>O=C(NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O | O[Li].O.COC(=O)C1OC(C(C(C1OC(C)=O)OC(C)=O)OC(C)=O)OC(NCCC1=CN(C2=CC=CC=C12)S(=O)(=O)C1=C(N=C2SC=CN21)Cl)=O.CO>>ClC=1N=C2SC=CN2C1S(=O)(=O)N1C=C(C2=CC=CC=C12)CCNC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)C(=O)O | CC(=O)[O:35][CH:34]1[CH:30]([C:31](=[O:32])[O:33]C)[O:29][CH:28]([O:27][C:2](=[O:1])[NH:3][CH2:4][CH2:5][c:6]2[cH:7][n:8]([S:9](=[O:10])(=[O:11])[c:12]3[c:13]([Cl:14])[n:15][c:16]4[s:17][cH:18][cH:19][n:20]34)[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]23)[CH:38]([O:39]C(C)=O)[CH:36]1[O:37]C(C)=O>>[O:1]=[C:2]([NH:3][CH2:4... | COC(=O)C1OC(OC(=O)NCCc2cn(S(=O)(=O)c3c(Cl)nc4sccn34)c3ccccc23)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O | O=C(NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O | null | null | O.C1CCOC1 | Reduction | OtherReaction | ac21e131e66a6fc26598d42c229af8ee8a14320b82729f3ff0604619f2d5774a | 774ba88a5fc25f9cae8664c12e4c35fb030d3c68b1211c590a49c4e8da3b6eaa | O=C(NCCc1cn(S(=O)(=O)c2cnc3sccn23)c2ccccc12)O[C@H]1CCCCO1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4]1-[#8:5]-[C:6](-[#8:7]-[C:8]=[O;D1;H0:9])-[CH;D3;+0:10](-[O;H0;D2;+0:11]-C(-C)=O)-[CH;D3;+0:12](-[O;H0;D2;+0:13]-C(-C)=O)-[CH;D3;+0:14]-1-[O;H0;D2;+0:15]-C(-C)=O>>[O;D1;H0:9]=[C:8]-[#8:7]-[C:6]1-[#8:5]-[C@H;D3;+0:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C@@H;D3;+0:14](-[OH... | 86 | [{"value": 86.0, "product": "ClC=1N=C2SC=CN2C1S(=O)(=O)N1C=C(C2=CC=CC=C12)CCNC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A solution of 3,4,5-triacetoxy-6-(2-{1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}ethycarbamoyloxy)tetrahydropyran-2-carboxylic acid methyl ester (1.0 g, 1.35 mmol) in THF is treated with CH3OH (38.8 mL) and H2O (10 mL), cooled to 0° C. (ice-water bath), treated with a solution of LiOH.H2O (340 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Carboxylic acid.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1cn2ccsc2n1.c1c[nH]c2ccccc12.C1CCOCC1 | HO- | O.C1CCOC1 | 0 | 2 | COC(=O)C1OC(OC(=O)NCCc2cn(S(=O)(=O)c3c(Cl)nc4sccn34)c3ccccc23)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O>O.C1CCOC1>O=C(NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47698fe631f744f7bb78fc6f4bd9c905 | O=C(Cl)OCc1ccccc1.O=C1CCNCC1>>O=C1CCN(C(=O)OCc2ccccc2)CC1 | O.Cl.N1CCC(CC1)=O.C(C1=CC=CC=C1)OC(=O)Cl.Cl>>C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=O | Cl[C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[O:1]=[C:2]1[CH2:3][CH2:4][NH:5][CH2:16][CH2:17]1>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | O=C(Cl)OCc1ccccc1.O=C1CCNCC1 | O=C1CCN(C(=O)OCc2ccccc2)CC1 | null | null | [OH-].[Na+] | Protection | N-alkylation of secondary amines with alkyl halides | c6eb958652ca8104567d61601fc03a9cfee33fb7bb328952993831b03fec41c4 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C1CCN(C(=O)OCc2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:6](=[O;D1;H0:5])-[C:11]-[C:10]-1 | 100.3 | [{"value": 100.3, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A 4-piperidone hydrochloride monohydrate (15.3 g) was dissolved in 2N aqueous solution of sodium hydroxide (100 mL). To the solution was added a benzyloxycarbonyl chloride (20.4 g) at 0° C. The mixture was stirred for 1 hour. The reaction mixture was neutralized with 2N hydrochloric acid, and the aqueous solution was e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HCl | [OH-].[Na+] | null | 1 | O=C(Cl)OCc1ccccc1.O=C1CCNCC1>[OH-].[Na+]>O=C1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b14c93ecec2d476e8a8652d824d39716 | CCCCN1C(=O)N(CC(C)C)C(=O)C12CCNCC2.OCCCCCCc1ccccc1>>CCCCN1C(=O)N(CC(C)C)C(=O)C12CCN(CCCCCCc1ccccc1)CC2.Cl | C(CCC)N1C(N(C(C12CCNCC2)=O)CC(C)C)=O.C(C)(C)N(C(C)C)CC.[O-]S(=O)Cl.S(=O)(=O)(C1=CC=C(C)C=C1)Cl.C1(=CC=CC=C1)CCCCCCO>>Cl.C(CCC)N1C(N(C(C12CCN(CC2)CCCCCCC2=CC=CC=C2)=O)CC(C)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[N:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:13](=[O:14])[C:15]12[CH2:16][CH2:17][NH:18][CH2:31][CH2:32]2.O[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[N:8]([CH2:9][CH:10]([CH3:11]... | CCCCN1C(=O)N(CC(C)C)C(=O)C12CCNCC2.OCCCCCCc1ccccc1 | CCCCN1C(=O)N(CC(C)C)C(=O)C12CCN(CCCCCCc1ccccc1)CC2.Cl | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | f01877d5f4d6b145622352021fe8f9745a4c30591b43e5dec47ccc59181025f7 | 6e06e85700930d51d4c0cb20c3022615516bd88d7fb3acc5347c37adfe490c2e | O=C1NC(=O)C2(CCN(CCCCCCc3ccccc3)CC2)N1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 58.9 | [{"value": 58.9, "product": "Cl.C(CCC)N1C(N(C(C12CCN(CC2)CCCCCCC2=CC=CC=C2)=O)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 18 | HOUR | To a solution of the compound prepared in Example 1 (28 mg) and N,N-diisopropylethylamine (155 mg) in acetonitrile (3 mL) were added benzenesulfonylchloride resin (Argonaut, product name PS-TsCl, product number 800276, 1.22 mmol/g, 0.20 mmol) (164 mg) and sulfonyl resin (175 mg) which is prepared from 6-phenylhexanol (... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CC2(CCN1)C[NH]C[NH]2 | C1CC2(CC[NH]1)C[NH]C[NH]2 | C1CC2(CC[NH]1)C[NH]C[NH]2.c1ccccc1 | null | C(C)#N | 70 | 18 | CCCCN1C(=O)N(CC(C)C)C(=O)C12CCNCC2.OCCCCCCc1ccccc1>C(C)#N>CCCCN1C(=O)N(CC(C)C)C(=O)C12CCN(CCCCCCc1ccccc1)CC2.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d47409756b99485191fa800c4bb3463b | CC(C)(C)OC(=O)OC(=O)[O-].CCCCN1C(=O)NC(=O)C12CCNCC2>>CCCCN1C(=O)NC(=O)C12CCN(C(=O)OC(C)(C)C)CC2 | Cl.C(CCC)N1C(NC(C12CCNCC2)=O)=O.C([O-])([O-])=O.[K+].[K+].C(=O)(OC(C)(C)C)OC(=O)[O-]>>C(CCC)N1C(NC(C12CCN(CC2)C(=O)OC(C)(C)C)=O)=O | O=C([O-])O[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[NH:8][C:9](=[O:10])[C:11]12[CH2:12][CH2:13][NH:14][CH2:22][CH2:23]2>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[NH:8][C:9](=[O:10])[C:11]12[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([... | CC(C)(C)OC(=O)OC(=O)[O-].CCCCN1C(=O)NC(=O)C12CCNCC2 | CCCCN1C(=O)NC(=O)C12CCN(C(=O)OC(C)(C)C)CC2 | null | null | O | Protection | Boc amine protection of secondary amine | d816530f227781f8e6590c0d5cfe00eacef223384b02c93d14dd45764d658f23 | 94226cf5c3bba13e4d3d11ce3d1edf3253d2a0a588e2936ded4f0148bd13453e | O=C1NC(=O)C2(CCNCC2)N1 | O=C(-[O-])-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11]-[C:12] | 89 | [{"value": 89.0, "product": "C(CCC)N1C(NC(C12CCN(CC2)C(=O)OC(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of the compound prepared in Example 5 (326 mg) in water (3 mL) were added potassium carbonate and t-butyl dicarbonate (348 mg) subsequently, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was neutralized with 1N hydrochloric acid. The aqueous layer was extracted three tim... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Acid.Carbonic Ester.Secondary amine | Carbamic ester | C1CC2(CCN1)CNC[NH]2 | C1CC2(CC[NH]1)CNC[NH]2 | C1CC2(CC[NH]1)CNC[NH]2 | HO- | O | null | 1 | CC(C)(C)OC(=O)OC(=O)[O-].CCCCN1C(=O)NC(=O)C12CCNCC2>O>CCCCN1C(=O)NC(=O)C12CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-976196165fb343849eb72f934f0676e2 | CS(C)=O.O=C1CCN(C(=O)OCc2ccccc2)CC1>>C=C1CCN(C(=O)OCc2ccccc2)CC1 | CS(=O)C.[H-].[Na+].CS(=O)C.O=C1CCN(CC1)C(=O)OCC1=CC=CC=C1.CS(=O)C.O>>C=C1CCN(CC1)C(=O)OCC1=CC=CC=C1 | CS(=O)[CH3:1].O=[C:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[CH2:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | CS(C)=O.O=C1CCN(C(=O)OCc2ccccc2)CC1 | C=C1CCN(C(=O)OCc2ccccc2)CC1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | null | C-C Coupling | OtherReaction | 593fb794de720cb3f59082c2c95327f5639ea17530f6acb7c816aef56ee603f2 | 6fc2b071b1f532559c8505df2edcc254183c53cc557dcde7348c30c4ff0e0293 | C=C1CCN(C(=O)OCc2ccccc2)CC1 | C-S(=O)-[CH3;D1;+0:1].O=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1>>[CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1 | null | [] | 60 | CELSIUS | 30 | MINUTE | A sodium hydride (13.2 g) was added to an anhydrous dimethylsulfoxide (176 mL) and the mixture was heated for 2 hours at 60° C. After cooling, to a suspension of methyltriphenylphosphonium bromide (110.4 g) in dimethylsulfoxide (120 mL) was added the reaction mixture, and the mixture was stirred for 30 minutes at room ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Sulfoxide | Vinyl | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | 60 | 0.5 | CS(C)=O.O=C1CCN(C(=O)OCc2ccccc2)CC1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>C=C1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8edc50dcb802428d8fb2902680b5c810 | O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1.O=CCCc1ccccc1>>O=C1c2ccccc2OC2(CCN(CCCc3ccccc3)CC2)CN1Cc1ccccc1 | C(C1=CC=CC=C1)N1CC2(CCNCC2)OC2=C(C1=O)C=CC=C2.C1(=CC=CC=C1)CCC=O>>C(C1=CC=CC=C1)N1CC2(CCN(CC2)CCCC2=CC=CC=C2)OC2=C(C1=O)C=CC=C2 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[O:9][C:10]2([CH2:11][CH2:12][NH:13][CH2:23][CH2:24]2)[CH2:25][N:26]1[CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.O=[CH:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[O:9][C:10]2([CH2:11][CH2:12][N:1... | O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1.O=CCCc1ccccc1 | O=C1c2ccccc2OC2(CCN(CCCc3ccccc3)CC2)CN1Cc1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | reductive amination | cab13708e7b292a586907f472f086163341816f4e309b786c5613261810170cd | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1c2ccccc2OC2(CCN(CCCc3ccccc3)CC2)CN1Cc1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | null | [] | 25 | CELSIUS | 8 | HOUR | To a solution of the compound prepared in Example 30 (0.01 mmol) in tetrahydrofuran (0.4 mL) were added 3-phenylpropanal (0.02 mmol) and MP-BH(OAc)3 (Argonaut, product number 800415, loading; 2.25 mmol/g) (13.3 mg). The mixture was stirred overnight at 25° C. To the reaction mixture were added tetrahydrofuran (0.4 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)C[NH]CC1(CCNCC1)O2 | c1ccc2c(c1)C[NH]CC1(CC[NH]CC1)O2 | c1ccc2c(c1)C[NH]CC1(CC[NH]CC1)O2.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | 25 | 8 | O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1.O=CCCc1ccccc1>O1CCCC1>O=C1c2ccccc2OC2(CCN(CCCc3ccccc3)CC2)CN1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36a25b36fc474b1286cb28173d92e0f6 | O=C(Cl)C1CCCC1.O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1>>O=C1c2ccccc2OC2(CCN(C(=O)C3CCCC3)CC2)CN1Cc1ccccc1 | C(C(CO)(CO)N)O.C(C1=CC=CC=C1)N1CC2(CCNCC2)OC2=C(C1=O)C=CC=C2.C1(CCCC1)C(=O)Cl>>C(C1=CC=CC=C1)N1CC2(CCN(CC2)C(=O)C2CCCC2)OC2=C(C1=O)C=CC=C2 | Cl[C:14](=[O:15])[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[O:9][C:10]2([CH2:11][CH2:12][NH:13][CH2:21][CH2:22]2)[CH2:23][N:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[O:9][C:10]2([CH2:11][CH2:12][N:13]([C:14](... | O=C(Cl)C1CCCC1.O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1 | O=C1c2ccccc2OC2(CCN(C(=O)C3CCCC3)CC2)CN1Cc1ccccc1 | null | null | ClC(C)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 36f1c0bfb99e2f9b2d14ec2c5050fb72b5b1281d5fcbeed0d46117918e5cbf45 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C1c2ccccc2OC2(CCN(C(=O)C3CCCC3)CC2)CN1Cc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5])-[C:9]-[C:10] | null | [] | 25 | CELSIUS | 8 | HOUR | To a solution of the compound prepared in Example 30 (0.010 mmol) in dichloroethane (0.7 mL) were added cyclopentanecarbonylchloride (0.020 mmol) and poly(4-vinylpyridine) (2% cross-linked, Aldrich, CAS#9017-40-7) (5.3 mg). The mixture was stirred overnight at 25° C. To the reaction mixture was added PS-trisamine (Argo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)C[NH]CC1(CCNCC1)O2 | c1ccc2c(c1)C[NH]CC1(CC[NH]CC1)O2 | c1ccc2c(c1)C[NH]CC1(CC[NH]CC1)O2.C1CCCC1.c1ccccc1 | HCl | ClC(C)Cl | 25 | 8 | O=C(Cl)C1CCCC1.O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1>ClC(C)Cl>O=C1c2ccccc2OC2(CCN(C(=O)C3CCCC3)CC2)CN1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee60cafbad574b10a5cdb22bc2c72c38 | O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1.O=C=NC1CCCC1>>O=C(NC1CCCC1)N1CCC2(CC1)CN(Cc1ccccc1)C(=O)c1ccccc1O2 | C(C(CO)(CO)N)O.C(C1=CC=CC=C1)N1CC2(CCNCC2)OC2=C(C1=O)C=CC=C2.C1(CCCC1)N=C=O>>C(C1=CC=CC=C1)N1CC2(CCN(CC2)C(=O)NC2CCCC2)OC2=C(C1=O)C=CC=C2 | [NH:9]1[CH2:10][CH2:11][C:12]2([CH2:13][CH2:14]1)[CH2:15][N:16]([CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[O:32]2.[O:1]=[C:2]=[N:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[N:9]1[CH2:10][CH2:11][C:12]2... | O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1.O=C=NC1CCCC1 | O=C(NC1CCCC1)N1CCC2(CC1)CN(Cc1ccccc1)C(=O)c1ccccc1O2 | null | null | ClC(C)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | f4f68aa12a4bf52f03cdb454deba752e653bd798d66151d0bd499d5ce7635a71 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC1CCCC1)N1CCC2(CC1)CN(Cc1ccccc1)C(=O)c1ccccc1O2 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2](-[C:1])-[C:6])-[C:10]-[C:11] | null | [] | 25 | CELSIUS | 8 | HOUR | To a solution of the compound prepared in Example 30 (0.010 mmol) in dichloroethane (0.7 mL) was added cyclopentylisocyanate (0.020 mmol), the mixture was stirred overnight at 25° C. To the reaction mixture was added PS-trisamine (Argonaut, product number 800229, loading; 4.36 mmol/g) (6.9 mg). After stirring overnight... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | c1ccc2c(c1)C[NH]CC1(CCNCC1)O2 | c1ccc2c(c1)C[NH]CC1(CC[NH]CC1)O2 | C1CCCC1.c1ccccc1.c1ccc2c(c1)C[NH]CC1(CC[NH]CC1)O2 | null | ClC(C)Cl | 25 | 8 | O=C1c2ccccc2OC2(CCNCC2)CN1Cc1ccccc1.O=C=NC1CCCC1>ClC(C)Cl>O=C(NC1CCCC1)N1CCC2(CC1)CN(Cc1ccccc1)C(=O)c1ccccc1O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-baafc576f1474e7fb9a12c824e87400d | Oc1ccnc2cccnc12.c1ccc2ncccc2c1>>CCCN.Nc1ccnc2cccnc12 | CS(=O)(=O)Cl.FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.N1=CC=CC2=CC=CC=C12.OC1=CC=NC2=CC=CN=C12>>NC1=CC=NC2=CC=CN=C12.C(CC)N | O[c:6]1[cH:7][cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][n:4][c:15]12.c1cc2c[cH:1][cH:2][cH:3]c2[n:5]c1>>[CH3:1][CH2:2][CH2:3][NH2:4].[NH2:5][c:6]1[cH:7][cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][n:14][c:15]12 | Oc1ccnc2cccnc12.c1ccc2ncccc2c1 | CCCN.Nc1ccnc2cccnc12 | null | null | N1=CC=CC=C1.P(=O)(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b920627501e0b78695d1f74f03b9b5240dde241078ccd0ada39ed7b9c7cd004c | 11a0d4fd36384a8e12e77a477d006f39b61f75211efa6ba3ed965004c60c82a4 | c1cnc2cccnc2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:10]:2:1.[cH;D2;+0:11]1:[cH;D2;+0:12]:[cH;D2;+0:13]:c2:[n;H0;D2;+0:14]:c:c:c:c:2:c:1>>[CH3;D1;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[NH2;D1;+0:9].[NH2;D1;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[cH;D2;... | null | [] | null | null | null | null | 4-Hydroxy-1,5-naphthyridines can be prepared from 3-aminopyridine derivatives by reaction with diethyl ethoxymethylene malonate to produce the 4-hydroxy-3-carboxylic acid ester derivative with subsequent hydrolysis to the acid, followed by thermal decarboxylation in quinoline (as for example described for 4-Hydroxy-[1,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Primary amine.Primary amine | c1cnc2cccnc2c1.c1ccc2ncccc2c1 | c1cnc2cccnc2c1 | c1cnc2cccnc2c1 | Other | N1=CC=CC=C1.P(=O)(Cl)(Cl)Cl | null | null | Oc1ccnc2cccnc12.c1ccc2ncccc2c1>N1=CC=CC=C1.P(=O)(Cl)(Cl)Cl>CCCN.Nc1ccnc2cccnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06b6e82898044d80ac59438df31c00cd | Brc1cccc2ccncc12>>O=c1[nH]ccc2cccc(Br)c12 | BrC=1C=CC=C2C=CN=CC12.C(C)OC(C=O)OCC>>BrC=1C=CC=C2C=CNC(C12)=O | [cH:2]1[n:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]12>>[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]12 | Brc1cccc2ccncc12 | O=c1[nH]ccc2cccc(Br)c12 | null | null | null | Oxidation | OtherReaction | e9c4006c1d3c140a429b5a663648b08cb79a652ba3eeab8801d7f4317b065849 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=c1[nH]ccc2ccccc12 | [c:1]:[c:2]1:[c:3]:[c:4]:[c:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:1>>[O;D1;H0:8]=[c;H0;D3;+0:7]1:[nH;D2;+0:6]:[c:5]:[c:4]:[c:3]:[c:2]:1:[c:1] | null | [] | null | null | null | null | The isoquinolin-8-yl system can be prepared from the appropriately substituted benzylamine by cyclocondensation with diethoxy-acetaldehyde (see, for example, K. Kido and Y. Watanabe, Chemical & Pharmaceutical Bulletin, 35(12), 4964-6; 1987). Alternatively 8-bromo-isoquinoline (prepared by the method of F. T. Tyson, J.A... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2cnccc2c1 | c1cccc2ccncc12 | c1cccc2ccncc12 | Other | null | null | null | Brc1cccc2ccncc12>>O=c1[nH]ccc2cccc(Br)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d9dc825fe334515b6fc7488d845bd7e | CC1(C)OC(=O)CC(=O)O1.N#Cc1ccc(N)cc1>>CC1(C)OC(=O)C(=CNc2ccc(C#N)cc2)C(=O)O1 | NC1=CC=C(C#N)C=C1.CC1(OC(CC(O1)=O)=O)C.COC(OC)OC>>CC1(OC(C(C(O1)=O)=CNC1=CC=C(C#N)C=C1)=O)C | [CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C:18](=[O:19])[O:20]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[C:7](=[CH:8][NH:9][c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[C:18](=[O:19])[O:20]1 | CC1(C)OC(=O)CC(=O)O1.N#Cc1ccc(N)cc1 | CC1(C)OC(=O)C(=CNc2ccc(C#N)cc2)C(=O)O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 16f6e689ff4988a3075463cf8c372a4929ef73d83eb11dd6443a2ba775713df7 | cb45d3f2664ea1c07edca6192a95c91d6c98f4c61196cc5a896d41447e7a94b5 | O=C1OCOC(=O)C1=CNc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12]-1=[C:13]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 97 | [{"value": 97.0, "product": "CC1(OC(C(C(O1)=O)=CNC1=CC=C(C#N)C=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-amino-benzonitrile (12.5 g, 0.106 mol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (18.3 g, 0.127 mol) and trimethylorthoformate (16 ml) in ethanol (100 ml) was refluxed for 3 hours. After cooling the solid was filtered off, washed with ethanol and air dried. The product was obtained as an off-white solid (27.9... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Enamine | C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | Other | C(C)O | null | null | CC1(C)OC(=O)CC(=O)O1.N#Cc1ccc(N)cc1>C(C)O>CC1(C)OC(=O)C(=CNc2ccc(C#N)cc2)C(=O)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e707d5fa7344215a30237ad995c66c0 | CC1(C)OC(=O)C(=CNc2ccc(C#N)cc2)C(=O)O1>>N#Cc1ccc2[nH]ccc(=O)c2c1 | CC1(OC(C(C(O1)=O)=CNC1=CC=C(C#N)C=C1)=O)C.C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2>>O=C1C=CNC2=CC=C(C=C12)C#N | CC1(C)OC(=O)[C:9](=[CH:8][NH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:13][cH:12]2)[C:10](=[O:11])O1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:10](=[O:11])[c:12]2[cH:13]1 | CC1(C)OC(=O)C(=CNc2ccc(C#N)cc2)C(=O)O1 | N#Cc1ccc2[nH]ccc(=O)c2c1 | null | null | CCOCC | Reduction | OtherReaction | 52b8b44ec33384424e5377fd29a8403152187dc69024d02f388dfabe3faf6d53 | be90257307957f9ad8e8667a185148216df19dcbaac80f1b7b16cd45c83e3aa5 | O=c1cc[nH]c2ccccc12 | C-C1(-C)-O-C(=O)-[C;H0;D3;+0:1](=[CH;D2;+0:2]-[NH;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8])-[C;H0;D3;+0:9](=[O;D1;H0:10])-O-1>>[O;D1;H0:10]=[c;H0;D3;+0:9]1:[cH;D2;+0:1]:[cH;D2;+0:2]:[nH;D2;+0:3]:[c:4](:[c:5]):[c;H0;D3;+0:6]:1:[c:7]:[c:8] | 94.3 | [{"value": 94.0, "product": "O=C1C=CNC2=CC=C(C=C12)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "O=C1C=CNC2=CC=C(C=C12)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Intermediate (a) (27.5 g, 0.101 mol) was slowly added over five minutes to refluxing Dowtherm A (200 ml). After an additional five minutes at reflux, the mixture was allow to cool to room temperature then ether (200 ml) was added. The product was filtered off, thoroughly washed with ether then air dried to afford the p... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | null | C1COCOC1.c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CCOCC | null | null | CC1(C)OC(=O)C(=CNc2ccc(C#N)cc2)C(=O)O1>CCOCC>N#Cc1ccc2[nH]ccc(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04563999b3a041a0b74bd013cbe3b613 | BrP(Br)Br.N#Cc1ccc2[nH]ccc(=O)c2c1>>N#Cc1ccc2nccc(Br)c2c1 | O=C1C=CNC2=CC=C(C=C12)C#N.P(Br)(Br)Br>>BrC1=CC=NC2=CC=C(C=C12)C#N | BrP(Br)[Br:11].O=[c:10]1[cH:9][cH:8][nH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:13][c:12]21>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][cH:9][c:10]([Br:11])[c:12]2[cH:13]1 | BrP(Br)Br.N#Cc1ccc2[nH]ccc(=O)c2c1 | N#Cc1ccc2nccc(Br)c2c1 | null | null | O.CN(C)C=O | Functional Group Interconversion | OtherReaction | 438e974ce5f8b1c45ff57c7a7dddacdfe9d2415c193d181f3fd6e6e5ac7f9d1c | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncccc2c1 | Br-P(-Br)-[Br;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 87 | [{"value": 87.0, "product": "BrC1=CC=NC2=CC=C(C=C12)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "BrC1=CC=NC2=CC=C(C=C12)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (b) (12 g, 70.5 mmol) in DMF (75 ml) was added dropwise phosphorous tribromide (8 ml, 84.6 mmol) over five minutes (slightly exothermic). The reaction was allowed to cool to room temperature and was then diluted with ice water (100 ml) and stirred 1 hour then diluted with additional water (300 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | O.CN(C)C=O | null | 1 | BrP(Br)Br.N#Cc1ccc2[nH]ccc(=O)c2c1>O.CN(C)C=O>N#Cc1ccc2nccc(Br)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3322c82fa1d54539995fdfa8f5ce8b6b | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.N#Cc1ccc2nccc(Br)c2c1>>C=Cc1ccnc2ccc(C#N)cc12 | BrC1=CC=NC2=CC=C(C=C12)C#N.C(=C)[Sn](CCCC)(CCCC)CCCC>>C(=C)C1=CC=NC2=CC=C(C=C12)C#N | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][n:6][c:7]2[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][c:14]12>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][n:6][c:7]2[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][c:14]12 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.N#Cc1ccc2nccc(Br)c2c1 | C=Cc1ccnc2ccc(C#N)cc12 | null | [Pd].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.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 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_vinyl | b76d02284eab1606d02e43e8d6b217f827d8bc76b0b2203ccf942abed5fcc5b2 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:9]=[C;D1;H2:10]>>[C;D1;H2:10]=[CH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | 64.5 | [{"value": 64.0, "product": "C(=C)C1=CC=NC2=CC=C(C=C12)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.5, "product": "C(=C)C1=CC=NC2=CC=C(C=C12)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (c) (1 g, 4.3 mmol) and vinyltributyltin (1.5 mL, 5.17 mmol) in degassed toluene (20 ml) was added tetrakis(triphenylphosphine) palladium (0) (245 mg, 5 mol %) and the mixture was refluxed under argon for 2 hours. Evaporation and flash silica chromatography eluting with chloroform afforded the product ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr.Sn | [Pd].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.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.C1(=CC=CC=C1)C | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.N#Cc1ccc2nccc(Br)c2c1>[Pd].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.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.C1(=CC=CC=C1)C>C=Cc1ccnc2ccc(C#N)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-281727cb74e9404f8ec80ef3f0e73d68 | C=Cc1ccnc2ccc(C#N)cc12.CC(C)(C)OC(=O)NC1CCNCC1>>CC(C)(C)OC(=O)NC1CCN(CCc2ccnc3ccc(C#N)cc23)CC1 | C(=C)C1=CC=NC2=CC=C(C=C12)C#N.C(C)(C)(C)OC(NC1CCNCC1)=O>>C(C)(C)(C)OC(NC1CCN(CC1)CCC1=CC=NC2=CC=C(C=C12)C#N)=O | [CH2:13]=[CH:14][c:15]1[cH:16][cH:17][n:18][c:19]2[cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25][c:26]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:27][CH2:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][c:15]2[cH:16][c... | C=Cc1ccnc2ccc(C#N)cc12.CC(C)(C)OC(=O)NC1CCNCC1 | CC(C)(C)OC(=O)NC1CCN(CCc2ccnc3ccc(C#N)cc23)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | d3e8cc768c824777b70742851768dcb27bf5f461c310912ac3f5a7abd08f6975 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | c1ccc2c(CCN3CCCCC3)ccnc2c1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | 99.9 | [{"value": 96.0, "product": "C(C)(C)(C)OC(NC1CCN(CC1)CCC1=CC=NC2=CC=C(C=C12)C#N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "C(C)(C)(C)OC(NC1CCN(CC1)CCC1=CC=NC2=CC=C(C=C12)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of (d) (150 mg, 0.8 mmol), piperidin-4-yl-carbamic acid tert-butyl ester (166 mg, 0.8 mmol) and chloroform (0.5 ml) were heated at 50° C. in a loosely capped vial for 6 hours. The product was purified by flash silica chromatography eluting with a 0-2% methanol in chloroform gradient affording the product as a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | null | C(Cl)(Cl)Cl | 50 | null | C=Cc1ccnc2ccc(C#N)cc12.CC(C)(C)OC(=O)NC1CCNCC1>C(Cl)(Cl)Cl>CC(C)(C)OC(=O)NC1CCN(CCc2ccnc3ccc(C#N)cc23)CC1 |
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