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-0d3522fbdd884f9ea992a9cf980ff044 | O=C1CCCNC12CCc1ccccc1C2>>OC1c2ccccc2CCC12CCCCN2 | N1C2(C(CCC1)=O)CC1=CC=CC=C1CC2.CO.[BH4-].[Na+]>>N1C2(CCCC1)C(C1=CC=CC=C1CC2)O | [O:1]=[C:12]1[C:11]2([CH2:2][c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[CH2:9][CH2:10]2)[NH:16][CH2:15][CH2:14][CH2:13]1>>[OH:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][CH2:10][C:11]12[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]2 | O=C1CCCNC12CCc1ccccc1C2 | OC1c2ccccc2CCC12CCCCN2 | null | null | O | Miscellaneous | OtherReaction | 24b2475629273829480e7d8cf68e36a8c1cd83adc110d39c767e13c6335a3909 | 65c0f1e474134afe581396038c9eec1081d3cf2c66a067b33a419661521d5253 | c1ccc2c(c1)CCC1(CCCCN1)C2 | [C:1]-[C:2]1(-[#7:3]-[C:4]-[C:5]-[C:6]-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8])-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[C:2]1(-[#7:3]-[C:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-1)-[CH;D3;+0:9](-[OH;D1;+0:8])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 30 | MINUTE | In 20 ml of methanol was dissolved 0.80 g of 3,4-dihydrospiro[naphthalene-2(1H),2'-piperidin]-one and following addition of 0.15 g of sodium borohydride in small portions, the mixture was stirred for 30 minutes. The reaction mixture was then diluted with water and extracted with methylene chloride. The methylene chlori... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCCN1)C2 | null | O | null | 0.5 | O=C1CCCNC12CCc1ccccc1C2>O>OC1c2ccccc2CCC12CCCCN2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-686546873c7d4c56ba5142ce531de9e0 | COc1ccc2c(c1)CCC1(CCCCN1)C2=O>>COc1ccc2c(c1)CCC1(CCCCN1)C2 | C(C)[SiH](CC)CC.COC=1C=C2CCC3(NCCCC3)C(C2=CC1)=O.Cl>>Cl.COC=1C=C2CCC3(NCCCC3)CC2=CC1 | O=[C:17]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][C:11]12[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][NH:16]1)[CH2:17]2 | COc1ccc2c(c1)CCC1(CCCCN1)C2=O | COc1ccc2c(c1)CCC1(CCCCN1)C2 | null | null | O.FC(C(=O)O)(F)F | Reduction | OtherReaction | 40edb481f91ef73120b0cb754905dfaf94acd35da35b5213a026564437b26a90 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc2c(c1)CCC1(CCCCN1)C2 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[C:5](-[C:6])(-[C:7])-[#7:8]-[C:9]>>[C:6]-[C:5](-[C:7])(-[#7:8]-[C:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | In 30 ml of trifluoroacetic acid was dissolved 6.57 g of 3,4-dihydro-6-methoxyspiro[naphthalene-2(1H),2'-piperidin]-1-one followed by addition of 8.5 ml of triethylsilane and the mixture was stirred for 1 hour. This reaction mixture was poured portionwise in water. To this was added 1N-hydrochloric acid and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCCN1)C2 | Other | O.FC(C(=O)O)(F)F | null | 1 | COc1ccc2c(c1)CCC1(CCCCN1)C2=O>O.FC(C(=O)O)(F)F>COc1ccc2c(c1)CCC1(CCCCN1)C2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-92aedeabdb674b35aa10924e69d9fbbd | BrCc1ccccc1.COc1cc2c(cc1OC)CC1(CCCCN1)CC2>>COc1cc2c(cc1OC)CC1(CCCCN1Cc1ccccc1)CC2 | Cl.COC=1C=C2CCC3(NCCCC3)CC2=CC1OC.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>COC=1C=C2CCC3(N(CCCC3)CC3=CC=CC=C3)CC2=CC1OC | Br[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][C:12]1([CH2:13][CH2:14][CH2:15][CH2:16][NH:17]1)[CH2:25][CH2:26]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][C:12]1([CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][c:... | BrCc1ccccc1.COc1cc2c(cc1OC)CC1(CCCCN1)CC2 | COc1cc2c(cc1OC)CC1(CCCCN1Cc1ccccc1)CC2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e76537564b204757c56ea9f15d9563556e48d483b30b2e91436650a0999d405b | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCCCC23CCc2ccccc2C3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[C:7])(-[C:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:5]-[C:6](-[C:7])(-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10]-[C:11] | null | [] | null | null | null | null | 3,4-Dihydro-6,7-dimethoxyspiro[naphthalene-2(1H),2'-piperidine] hydrochloride (10 mg) was treated with potassium carbonate (10 g) and benzyl bromide (4 ml) in DMF (300 ml) at 60° C. for 2 hours. The reaction product was extracted with ethyl acetate-water, washed with water, dried, and concentrated. Purification with si... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCC[NH]1)C2 | c1ccc2c(c1)CCC1(CCCC[NH]1)C2.c1ccccc1 | HBr | CN(C)C=O | null | null | BrCc1ccccc1.COc1cc2c(cc1OC)CC1(CCCCN1)CC2>CN(C)C=O>COc1cc2c(cc1OC)CC1(CCCCN1Cc1ccccc1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4cc0c6f610bb40f9a1e1e4c513076ae5 | COc1ccc2c(c1)CCC1(CCCCN1C(=O)C(F)(F)F)C2.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F.O=[N+]([O-])[O-].[NH4+]>>COc1cc2c(cc1[N+](=O)[O-])CC1(CCCCN1C(=O)C(F)(F)F)CC2.COc1ccc2c(c1[N+](=O)[O-])CCC1(CCCCN1C(=O)C(F)(F)F)C2 | FC(C(=O)OC(C(F)(F)F)=O)(F)F.O.FC(C(=O)N1C2(CCCC1)CC1=CC=C(C=C1CC2)OC)(F)F.[N+](=O)([O-])[O-].[NH4+]>>FC(C(=O)N1C2(CCCC1)CC1=CC(=C(C=C1CC2)OC)[N+](=O)[O-])(F)F.FC(C(=O)N1C2(CCCC1)CC1=CC=C(C(=C1CC2)[N+](=O)[O-])OC)(F)F | [CH3:1][O:2][c:3]1[cH:4][c:33]2[c:32]([cH:31][cH:30]1)[CH2:52][C:13]1([N:18]([C:19](=[O:20])[C:21]([F:22])([F:23])[F:24])[CH2:17][CH2:43][CH2:42][CH2:41]1)[CH2:39][CH2:38]2.[OH2:36].F[C:5](F)(F)[C:27](O[C:15]([C:16]([F:49])([F:50])[F:51])=[O:47])=[O:28].[N+:9](=[O:10])([O-:11])[O-:37].[NH4+:45]>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccc2c(c1)CCC1(CCCCN1C(=O)C(F)(F)F)C2.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F.O=[N+]([O-])[O-].[NH4+] | COc1cc2c(cc1[N+](=O)[O-])CC1(CCCCN1C(=O)C(F)(F)F)CC2.COc1ccc2c(c1[N+](=O)[O-])CCC1(CCCCN1C(=O)C(F)(F)F)C2 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 3a13d919ad36cc369c9146e3aee3c8ebfb823918c4bcd743476089bdf57d5fef | 2acc14181a82a68dfc7ff499b15e5d6f8c9c09c327ac75439e4d543595b2222f | c1ccc2c(c1)CCC1(CCCCN1)C2.c1ccc2c(c1)CCC1(CCCCN1)C2 | F-[C;H0;D4;+0:1](-F)(-F)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-O-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C;H0;D4;+0:6](-[F;H0;D1;+0:7])(-[F;H0;D1;+0:8])-[F;H0;D1;+0:9].[C;D1;H3:10]-[#8:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[c:14]:[c:15]2:[c;H0;D3;+0:16](:[cH;D2;+0:17]:1)-[C:18]-[CH2;D2;+0:19]-[C;H0;D4;+0:20]1(-[CH2;D2;+0:21]-[C:22]-[C... | null | [] | null | null | 8 | HOUR | 6.0 g of 1'-trifluoroacetyl-3,4-dihydro-6-methoxyspiro[naphthalene-2(1H),2'-piperidine] was dissolved in 150 ml of chloroform. After 1.5 g of ammonium nitrate was suspended in this solution, 9 ml of trifluoroacetic anhydride was added, followed by overnight stirring at room temperature. After water was added, the react... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trifluoro group.Anhydride.Ether.Nitrate | Trifluoro group.Ether.Ether.Nitro group.Nitro group.Tertiary amide | c1ccc2c(c1)CCC1(CCCC[NH]1)C2 | c1ccc2c(c1)CCC1(CCCC[NH]1)C2.c1ccc2c(c1)CCC1(CCCC[NH]1)C2 | c1ccc2c(c1)CCC1(CCCC[NH]1)C2.c1ccc2c(c1)CCC1(CCCC[NH]1)C2 | null | C(Cl)(Cl)Cl | null | 8 | COc1ccc2c(c1)CCC1(CCCCN1C(=O)C(F)(F)F)C2.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F.O=[N+]([O-])[O-].[NH4+]>C(Cl)(Cl)Cl>COc1cc2c(cc1[N+](=O)[O-])CC1(CCCCN1C(=O)C(F)(F)F)CC2.COc1ccc2c(c1[N+](=O)[O-])CCC1(CCCCN1C(=O)C(F)(F)F)C2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3b6a2edc981a43d985cbda64672bb38c | CCOC(=O)C1(N)CCc2cc(OC)c(OC)cc2C1.CN(CC(=O)O)C(=O)OCc1ccccc1>>CCOC(=O)C1(NC(=O)CN(C)C(=O)OCc2ccccc2)CCc2cc(OC)c(OC)cc2C1 | NC1(CC2=CC(=C(C=C2CC1)OC)OC)C(=O)OCC.C(C1=CC=CC=C1)OC(=O)N(C)CC(=O)O.Cl.C(C)N=C=NCCCN(C)C.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(=O)N(C)CC(=O)NC1(CC2=CC(=C(C=C2CC1)OC)OC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([NH2:7])[CH2:23][CH2:24][c:25]2[cH:26][c:27]([O:28][CH3:29])[c:30]([O:31][CH3:32])[cH:33][c:34]2[CH2:35]1.O[C:8](=[O:9])[CH2:10][N:11]([CH3:12])[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([NH:7][C:8](=[O:9])[CH2:... | CCOC(=O)C1(N)CCc2cc(OC)c(OC)cc2C1.CN(CC(=O)O)C(=O)OCc1ccccc1 | CCOC(=O)C1(NC(=O)CN(C)C(=O)OCc2ccccc2)CCc2cc(OC)c(OC)cc2C1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)OCc1ccccc1)NC1CCc2ccccc2C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[C:7]-[C:8](-[NH2;D1;+0:9])(-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[C:14]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6])(-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[C:14] | 75.7 | [{"value": 74.0, "product": "C(C1=CC=CC=C1)OC(=O)N(C)CC(=O)NC1(CC2=CC(=C(C=C2CC1)OC)OC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "C(C1=CC=CC=C1)OC(=O)N(C)CC(=O)NC1(CC2=CC(=C(C=C2CC1)OC)OC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of ethyl 2-amino-1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylate (430 mg, 1.5 mmol), N-benzyloxycarbonylsarcosine (357 mg, 1.6 mmol), and 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride in dichloromethane (5 ml) was added triethylamine (160 mg, 1.6 mmol) under stirring at 0° C. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | ClCCl | 0 | null | CCOC(=O)C1(N)CCc2cc(OC)c(OC)cc2C1.CN(CC(=O)O)C(=O)OCc1ccccc1>ClCCl>CCOC(=O)C1(NC(=O)CN(C)C(=O)OCc2ccccc2)CCc2cc(OC)c(OC)cc2C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9bd1f43edb1547daa2f9d118ae4fcc96 | CCOC(=O)C1(NC(=O)CN(C)C(=O)OCc2ccccc2)CCc2cc(OC)c(OC)cc2C1>>COc1cc2c(cc1OC)CC1(CC2)NC(=O)CC(C)C1=O | C(C1=CC=CC=C1)OC(=O)N(C)CC(=O)NC1(CC2=CC(=C(C=C2CC1)OC)OC)C(=O)OCC.C(C)O>>COC=1C=C2CCC3(NC(CC(C3=O)C)=O)CC2=CC1OC | CCO[C:21]([C:12]1([NH:15][C:16](=[O:17])[CH2:18]N(C(=O)OCc2ccccc2)[CH3:20])[CH2:11][c:6]2[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([O:9][CH3:10])[cH:7]2)[CH2:14][CH2:13]1)=[O:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][C:12]1([CH2:13][CH2:14]2)[NH:15][C:16](=[O:17])[CH2:18][CH:19]([CH3:20])[C... | CCOC(=O)C1(NC(=O)CN(C)C(=O)OCc2ccccc2)CCc2cc(OC)c(OC)cc2C1 | COc1cc2c(cc1OC)CC1(CC2)NC(=O)CC(C)C1=O | null | [Pd].[C] | null | Functional Group Interconversion | OtherReaction | 1e566ba0eac3c52117da9c22073fbafe2426e0ffb781a46d21ae0e9ee9c169a8 | ade0f728b01244fc6e52cce96c5fb074e8879beca54d54dd1088ee9c68307904 | O=C1CCC(=O)C2(CCc3ccccc3C2)N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-N(-[CH3;D1;+0:8])-C(=O)-O-C-c1:c:c:c:c:c:1)(-[C:9])-[C:10]>>[C:9]-[C:3]1(-[C:10])-[#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:11](-[CH3;D1;+0:8])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | 80 | CELSIUS | null | null | A solution of ethyl 2-[(N-benzyloxycarbonyl-N-methylamino)acetylamino]-1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylate (550 mg, 1.1 mmol) in ethanol (20 ml) was hydrogenated in the presence of 10% Pd-carbon (250 mg) for 6 hr. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether | Ketone | c1ccccc1 | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCCN1)C2 | HO- | [Pd].[C] | 80 | null | CCOC(=O)C1(NC(=O)CN(C)C(=O)OCc2ccccc2)CCc2cc(OC)c(OC)cc2C1>[Pd].[C]>COc1cc2c(cc1OC)CC1(CC2)NC(=O)CC(C)C1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-de27506f180e47a2ad3ca470cfd3bc5a | COc1cc2c(cc1OC)CC1(CC2)NC(=O)CN(C)C1=O>>COc1cc2c(cc1OC)CC1(CC2)CN(C)CCN1 | [OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].COC=1C=C2CCC3(NC(CN(C3=O)C)=O)CC2=CC1OC>>COC=1C=C2CCC3(NCCN(C3)C)CC2=CC1OC | O=[C:15]1[C:12]2([CH2:11][c:6]3[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([O:9][CH3:10])[cH:7]3)[CH2:14][CH2:13]2)[NH:20][C:19](=O)[CH2:18][N:16]1[CH3:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][C:12]1([CH2:13][CH2:14]2)[CH2:15][N:16]([CH3:17])[CH2:18][CH2:19][NH:20]1 | COc1cc2c(cc1OC)CC1(CC2)NC(=O)CN(C)C1=O | COc1cc2c(cc1OC)CC1(CC2)CN(C)CCN1 | null | null | CCOCC | Reduction | OtherReaction | 43346047900f30adf11967aa3aafab0638be00f3681f83791b2433d662065d71 | 1e111e1677c741c445104f499dde4d06874c64781551b41f18ee18795c631ec3 | c1ccc2c(c1)CCC1(CNCCN1)C2 | O=[C;H0;D3;+0:1]1-[#7:2](-[C;D1;H3:3])-[C:4]-[C;H0;D3;+0:5](=O)-[#7:6]-[C:7]-1(-[C:8])-[C:9]>>[C:8]-[C:7]1(-[C:9])-[#7:6]-[CH2;D2;+0:5]-[C:4]-[#7:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-1 | 95 | [{"value": 86.0, "product": "COC=1C=C2CCC3(NCCN(C3)C)CC2=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "COC=1C=C2CCC3(NCCN(C3)C)CC2=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a suspension of lithium aluminum hydride (114 mg, 3 mmol) and aluminum chloride (400 mg, 3 mmol) in ether (4 ml) was added the suspension of 3,4-dihydro-6,7-dimethoxy-4'-methylspiro[naphthalene-2(1H),2'-piperazine]-3',6'-dione (50 mg, 0.16 mmol) in ether (2 ml). The reaction mixture was stirred at ambient temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amide | null | c1ccc2c(c1)CCC1(C[NH]CCN1)C2 | c1ccc2c(c1)CCC1(C[NH]CCN1)C2 | c1ccc2c(c1)CCC1(C[NH]CCN1)C2 | Other | CCOCC | null | 0.75 | COc1cc2c(cc1OC)CC1(CC2)NC(=O)CN(C)C1=O>CCOCC>COc1cc2c(cc1OC)CC1(CC2)CN(C)CCN1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8f22d5e763004e2ebbd516fb90970a8d | O=CNCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1>>NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1 | C(=O)NCC(CCCN1CCC(CC1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[OH-].[Na+]>>NCC(CCCN1CCC(CC1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O=C[NH:1][CH2:2][C:3]([CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[NH2:1][CH2:2][C:3]([CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:14]... | O=CNCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1 | NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(C2CCN(CCCC(c3ccccc3)c3ccccc3)CC2)cc1 | O=C-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 100.3 | [{"value": 100.3, "product": "NCC(CCCN1CCC(CC1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-(5-formylamino-4,4-diphenylpentyl)-4-phenylpiperidine (2.07 g) in methanol (50 ml) was added 1N-sodium hydroxide (30 ml) and the mixture was refluxed overnight. This reaction mixture was concentrated to dryness and the group was extracted using methylene chloride and water. The organic layer was wash... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CO | null | null | O=CNCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1>CO>NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dd8d9889812644d1ab380e5a374a299b | COc1ccc2c(c1)CCC1(CCCCN1CCCC(CC#N)(c1ccccc1)c1ccccc1)C2>>COc1ccc2c(c1)CCC1(CCCCN1CCCC(CCN)(c1ccccc1)c1ccccc1)C2 | [OH-].[Na+].COC=1C=C2CCC3(N(CCCC3)CCCC(CC#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2=CC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O>>COC=1C=C2CCC3(N(CCCC3)CCCC(CCN)(C3=CC=CC=C3)C3=CC=CC=C3)CC2=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][C:20]([CH2:21][C:22]#[N:23])([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1)[CH2:36]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:... | COc1ccc2c(c1)CCC1(CCCCN1CCCC(CC#N)(c1ccccc1)c1ccccc1)C2 | COc1ccc2c(c1)CCC1(CCCCN1CCCC(CCN)(c1ccccc1)c1ccccc1)C2 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(C(CCCN2CCCCC23CCc2ccccc2C3)c2ccccc2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 89.2 | [{"value": 89.2, "product": "COC=1C=C2CCC3(N(CCCC3)CCCC(CCN)(C3=CC=CC=C3)C3=CC=CC=C3)CC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 3,4-dihydro-6-methoxy-1'-(5-cyano-4,4-diphenylpentyl)spiro[naphthalene-2(1H),2'-piperidine] (0.6 g) in tetrahydrofuran (15 ml) was added lithium aluminum hydride (95 mg) portionwise under ice-cooling and stirring. After completion of dropwise addition, the mixture was heated at 60° C. for 6 hours. To t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2c(c1)CCC1(CCCC[NH]1)C2.c1ccccc1.c1ccccc1 | null | O1CCCC1 | 60 | null | COc1ccc2c(c1)CCC1(CCCCN1CCCC(CC#N)(c1ccccc1)c1ccccc1)C2>O1CCCC1>COc1ccc2c(c1)CCC1(CCCCN1CCCC(CCN)(c1ccccc1)c1ccccc1)C2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-512e99f9a9254acd8ab4b706e0bfbb8f | CNC.O=CNCC(CCCI)(c1ccccc1)c1ccccc1>>CN(C)CCCC(CNC=O)(c1ccccc1)c1ccccc1 | C(=O)NCC(CCCI)(C1=CC=CC=C1)C1=CC=CC=C1.Cl.CNC.C(C)N(CC)CC.C([O-])([O-])=O.[K+].[K+]>>CN(C)CCCC(CNC=O)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][NH:2][CH3:3].I[CH2:4][CH2:5][CH2:6][C:7]([CH2:8][NH:9][CH:10]=[O:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C:7]([CH2:8][NH:9][CH:10]=[O:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:... | CNC.O=CNCC(CCCI)(c1ccccc1)c1ccccc1 | CN(C)CCCC(CNC=O)(c1ccccc1)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(Cc2ccccc2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 67.1 | [{"value": 67.1, "product": "CN(C)CCCC(CNC=O)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-formylamino-1-iodo-4,4-diphenylpentane (8.5 g), dimethylamine hydrochloride (17.63 g), triethylamine (30.1 ml), and potassium carbonate (3 g) was heated in acetonitrile (250 ml) at 60° C. for 2 hours. This reaction mixture was concentrated to dryness and the group was extracted using ethyl acetate and wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | HI | C(C)#N | null | null | CNC.O=CNCC(CCCI)(c1ccccc1)c1ccccc1>C(C)#N>CN(C)CCCC(CNC=O)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-39787aa98c37454d9bfacfbb145e24ab | Cc1ccc(S(=O)(=O)NCC(CCCNCc2cccc([N+](=O)[O-])c2)(c2ccccc2)c2ccccc2)cc1>>Cc1ccc(S(=O)(=O)NCC(CCCNCc2cccc(N)c2)(c2ccccc2)c2ccccc2)cc1 | C1(=CC=CC=C1)C(CCCNCC1=CC(=CC=C1)[N+](=O)[O-])(CNS(=O)(=O)C1=CC=C(C)C=C1)C1=CC=CC=C1.Cl>>NC=1C=C(CNCCCC(CNS(=O)(=O)C2=CC=C(C)C=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1 | O=[N+:22]([O-])[c:21]1[cH:20][cH:19][cH:18][c:17]([CH2:16][NH:15][CH2:14][CH2:13][CH2:12][C:11]([CH2:10][NH:9][S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:37][cH:36]2)(=[O:7])=[O:8])([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7... | Cc1ccc(S(=O)(=O)NCC(CCCNCc2cccc([N+](=O)[O-])c2)(c2ccccc2)c2ccccc2)cc1 | Cc1ccc(S(=O)(=O)NCC(CCCNCc2cccc(N)c2)(c2ccccc2)c2ccccc2)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(NCC(CCCNCc1ccccc1)(c1ccccc1)c1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 74.7 | [{"value": 74.7, "product": "NC=1C=C(CNCCCC(CNS(=O)(=O)C2=CC=C(C)C=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4,4-diphenyl-1-(3-nitrobenzylamino)-5-(tosylamino)pentane (0.17 g) in ethanol (10 ml) was added hydrochloric acid (0.1 ml) as well as 10% palladium-on-carbon (80 mg) and the mixture was subjected to catalytic hydrogenation at atmospheric temperature and pressure. The catalyst was then removed from the ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].C(C)O | null | null | Cc1ccc(S(=O)(=O)NCC(CCCNCc2cccc([N+](=O)[O-])c2)(c2ccccc2)c2ccccc2)cc1>[Pd].C(C)O>Cc1ccc(S(=O)(=O)NCC(CCCNCc2cccc(N)c2)(c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f481802e6a614778937029828a5a0491 | CS(=O)(=O)Cl.NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1>>CS(=O)(=O)NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1.Cl | NCC(CCCN1CCC(CC1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>Cl.C1(=CC=CC=C1)C(CCCN1CCC(CC1)C1=CC=CC=C1)(CNS(=O)(=O)C)C1=CC=CC=C1 | [CH3:1][S:2](=[O:3])(=[O:4])[Cl:35].[NH2:5][CH2:6][C:7]([CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1)([c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][C:7]([CH2:8][CH2:... | CS(=O)(=O)Cl.NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1 | CS(=O)(=O)NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1.Cl | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc(C2CCN(CCCC(c3ccccc3)c3ccccc3)CC2)cc1 | [C;D1;H3:1]-[S;H0;D4;+0:2](-[Cl;H0;D1;+0:3])(=[O;D1;H0:4])=[O;D1;H0:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[S;H0;D4;+0:2](-[C;D1;H3:1])(=[O;D1;H0:4])=[O;D1;H0:5].[ClH;D0;+0:3] | null | [] | null | null | null | null | To a solution of 5-amino-4,4-diphenyl-1-(4-phenylpiperidino)pentane (0.4 g) and triethylamine (0.42 ml) in methylene chloride (15 ml) was added methanesulfonyl chloride (0.1 ml) dropwise under ice-cooling and stirring. After completion of dropwise addition, the mixture was returned to room temperature and stirred for a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | CS(=O)(=O)Cl.NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CS(=O)(=O)NCC(CCCN1CCC(c2ccccc2)CC1)(c1ccccc1)c1ccccc1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-206c74739b404c849cda9be7a167a4f0 | N#CCCC(C=O)(c1ccccc1)c1ccccc1>>C=CC(O)C(CCC#N)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(CCC#N)(C=O)C1=CC=CC=C1.C(=C)[Mg]Br.O1CCCC1.[Cl-].[NH4+]>>C1(=CC=CC=C1)C(CCC#N)(C(C=C)O)C1=CC=CC=C1 | [CH:3](=[O:4])[C:5]([CH2:6][CH2:7][C:8]#[N:9])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH2:1]=[CH:2][CH:3]([OH:4])[C:5]([CH2:6][CH2:7][C:8]#[N:9])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | N#CCCC(C=O)(c1ccccc1)c1ccccc1 | C=CC(O)C(CCC#N)(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 7c95c9d475b3e4739c4b4bffdb557ccc0332365664dc5f751958e7bb4139acbc | 1cfdacde78204b273e664dc0eb50ffc4dc70522ea435514fcadd01e492b9b547 | c1ccc(Cc2ccccc2)cc1 | [C:1]-[C:2](-[c:3])(-[c:4])-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[C:1]-[C:2](-[c:3])(-[c:4])-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7]=[C;D1;H2:8] | null | [] | null | null | null | null | Under argon gas, 4,4-diphenyl-4-formylbutanenitrile (5.0 g) was dissolved in dry tetrahydrofuran (200 ml). Then, 1M vinylmagnesium bromide-tetrahydrofuran (30 ml) was added dropwise -40° C. After completion of addition, the reaction temperature was allowed to rise gradually to 0° C. (over 3 hours). After completion of ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol.Vinyl | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | null | N#CCCC(C=O)(c1ccccc1)c1ccccc1>O1CCCC1>C=CC(O)C(CCC#N)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7124bdd5272a4ae488ccd70f9adb1d70 | N[C@@H](CCC(=O)O)C(=O)O.Nc1ccc(S(=O)(=O)O)cc1.O=C(O)/C=C\C(=O)O.O=C(O)[C@@H]1CCCN1>>C1COCCN1.CCCCN.CCCN | C(\C=C/C(=O)O)(=O)O.C1(\C=C/C(=O)O1)=O.NCC(=O)O.N[C@@H](CCC(=O)O)C(=O)O.N[C@@H](C)C(=O)O.N1[C@H](C(=O)O)CCC1.C(C=1C(N)=CC=CC1)(=O)O.C1(\C=C/C(=O)O1)=O.S(=O)(C1=CC=C(C=C1)N)(=O)O.NC1=C(C(=CC=C1)C)S(=O)(=O)O.C=1C=CC=2C=C(C=CC2C1)N.C=1C=CC=2C=C(C=CC2C1)N>>C1(\C=C/C(=O)O1)=O.C(CC)N.C(CCC)N.N1CCOCC1 | O=C(O)CC[C@@H](C(=O)O)[NH2:6].O=S(=O)(O)[c:7]1[cH:4][cH:5][c:10]([NH2:11])[cH:9][cH:8]1.O=C(O)/C=[CH:1]\[C:2](=O)[OH:3].O=C(O)[C@@H]1[CH2:12][CH2:13][CH2:14][NH:15]1>>[CH2:1]1[CH2:2][O:3][CH2:4][CH2:5][NH:6]1.[CH3:7][CH2:8][CH2:9][CH2:10][NH2:11].[CH3:12][CH2:13][CH2:14][NH2:15] | N[C@@H](CCC(=O)O)C(=O)O.Nc1ccc(S(=O)(=O)O)cc1.O=C(O)/C=C\C(=O)O.O=C(O)[C@@H]1CCCN1 | C1COCCN1.CCCCN.CCCN | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9ef43ec893906d526b8efc2c8f7bd766d08677a08736af6c7264afc1ae0701cd | b21ff3392680300b41449088b20ca9844ed9d399d436929809148c0373cac5ed | C1COCCN1 | O-C(=O)-C-C-[C@@H](-[NH2;D1;+0:1])-C(-O)=O.O-C(=O)-[C@H]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[NH;D2;+0:5]-1.O-C(=O)/C=[CH;D2;+0:6]\[C;H0;D3;+0:7](=O)-[OH;D1;+0:8].O-S(=O)(=O)-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[N;D1;H2:13]):[cH;D2;+0:14]:[cH;D2;+0:15]:1>>[CH2;D2;+0:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[CH2... | null | [] | null | null | null | null | Examples of monomers which can provide structure units represented by Formula (4) include half amides of maleic acid, prepared by the reaction of maleic anhydride with glycine, glutamic acid, alanine, proline, anthranilic acid or by the reaction of maleic anhydride with sulfanilic acid, amino-toluene sulfonic acid, nap... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Primary amine.Secondary amine.Sulfonic acid | Ether.Primary amine.Secondary amine | c1ccccc1.C1CCNC1 | C1COCCN1 | C1COCCN1 | Other | null | null | null | N[C@@H](CCC(=O)O)C(=O)O.Nc1ccc(S(=O)(=O)O)cc1.O=C(O)/C=C\C(=O)O.O=C(O)[C@@H]1CCCN1>>C1COCCN1.CCCCN.CCCN |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3b264efffb7c4bf6baad7d517a038167 | CC(C)(C)[Si](C)(C)Cl.COC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>>COC(=O)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | O.OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O | Cl[Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[CH2:10][c:11]1[c:12]([O:13][CH3:14])[c:15]([CH3:16])[c:17]2[c:18]([c:19]1[OH:20])[C:28](=[O:29])[O:30][CH2:31]2>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[CH2:10][c:11]1[c:... | CC(C)(C)[Si](C)(C)Cl.COC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | COC(=O)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | null | CN(C=O)C | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | O=C1OCc2ccccc21 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[O;H0;D2;+0:13]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]):[c:14] | null | [] | 50 | CELSIUS | 24 | HOUR | To methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -4-methyl-4-hexenoate (Tetrahedron, 28, 4395, 1972) (10.0 g) in dimethylformamide (75 ml) was added t-butyldimethylsilyl chloride (4.97 g) and imidazole (2.24 g). The mixture was heated at 50° C. for 1 hour, then left at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2c(c1)COC2 | HCl | CN(C=O)C | 50 | 24 | CC(C)(C)[Si](C)(C)Cl.COC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>CN(C=O)C>COC(=O)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dfb5a7b7973c4b7fbba91920cc2aedaa | COC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O.COCCOCCl>>COCCOCOc1c(C/C=C(\C)CCC(=O)OC)c(OC)c(C)c2c1C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O.C(C)(C)N(CC)C(C)C.COCCOCCl>>COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CCC(=O)OC)\C | [OH:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH2:14][CH2:15][C:16](=[O:17])[O:18][CH3:19])[c:20]([O:21][CH3:22])[c:23]([CH3:24])[c:25]2[c:26]1[C:27](=[O:28])[O:29][CH2:30]2.Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH2:14]... | COC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O.COCCOCCl | COCCOCOc1c(C/C=C(\C)CCC(=O)OC)c(OC)c(C)c2c1C(=O)OC2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | O=C1OCc2ccccc21 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[#8:2]-[C:3]):[c:10] | null | [] | null | null | null | null | To methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (61.0 g) in methylene chloride (1000 ml) at 0° C. was added diisopropylethylamine (30.4 g) and methoxyethoxymethyl chloride (29.2 g). After 31/2 hours the solution was washed with dilute hydrochloric acid, dried and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccc2c(c1)COC2 | HCl | C(Cl)Cl | null | null | COC(=O)CC/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O.COCCOCCl>C(Cl)Cl>COCCOCOc1c(C/C=C(\C)CCC(=O)OC)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-782f3ef968454e2fb4c7a53a51cbf910 | COC(=O)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC=O)C(=O)OC2 | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O.ClCCl.N1=CC=CC=C1.CO>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC=O)OC)C)=O | COC(CC/C(C)=[CH:19]/[CH2:18][c:17]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[C:21](=[O:22])[O:23][CH2:24]2)=[O:20]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]1[CH... | COC(=O)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC=O)C(=O)OC2 | null | null | null | Miscellaneous | Alkene oxidation to aldehyde | bead50fbe5f064ca194dd6539169819285be7ad836d4784cf731500fc82ffd81 | 4c6528619563bcf8307b99ed5b55eeec359e10edc84b38b6723a7f0e61ea5d01 | O=C1OCc2ccccc21 | C-O-C(=[O;H0;D1;+0:1])-C-C/C(-C)=[CH;D2;+0:2]/[C:3]-[c:4]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | 45 | MINUTE | A solution of methyl (E)-6-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (11.0 g) in methanol 125 ml), dichloromethane (125 ml) and pyridine (2 ml) was cooled to -78° C. and a stream of ozonized oxygen was bubbled through. After 45 minutes a blue color developed... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccc2c(c1)COC2 | HO- | null | null | 0.75 | COC(=O)CC/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC=O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ea17c53062cd4009bf12f9a094220e13 | COCCOCOc1c(C/C=C(\C)CCC(=O)OC)c(OC)c(C)c2c1C(=O)OC2>>COCCOCOc1c(C/C=C(\C)CCC(=O)O)c(OC)c(C)c2c1C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CCC(=O)OC)\C.[OH-].[Na+]>>COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CCC(=O)O)\C | C[O:18][C:16]([CH2:15][CH2:14]/[C:12](=[CH:11]/[CH2:10][c:9]1[c:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:25]2[c:24]([c:22]([CH3:23])[c:19]1[O:20][CH3:21])[CH2:29][O:28][C:26]2=[O:27])[CH3:13])=[O:17]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH2:14][CH2:15][C:16... | COCCOCOc1c(C/C=C(\C)CCC(=O)OC)c(OC)c(C)c2c1C(=O)OC2 | COCCOCOc1c(C/C=C(\C)CCC(=O)O)c(OC)c(C)c2c1C(=O)OC2 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccccc21 | 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] | null | [] | null | null | null | null | To methyl (E)-6-(1,3-dihydro-6-methoxy -4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (76.0 g) in methanol (300 ml) was added 1N aqueous sodium hydroxide (300 ml). After 11/2 hours the solution was diluted with water, washed twice with ether, then acidified with dilute hydrochloric acid.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)COC2 | Other | O.CO | null | null | COCCOCOc1c(C/C=C(\C)CCC(=O)OC)c(OC)c(C)c2c1C(=O)OC2>O.CO>COCCOCOc1c(C/C=C(\C)CCC(=O)O)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9c6929ae720b47be8f9702cfd7e578b5 | COCCOCOc1c(C/C=C(\C)CCC(=O)O)c(OC)c(C)c2c1C(=O)OC2>>COCCOCOc1c(CC=O)c(OC)c(C)c2c1C(=O)OC2 | CCCCCC.C(C)(=O)OCC.COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CCC(=O)O)\C>>COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CC=O | C/C(CCC(=O)[OH:12])=[CH:11]\[CH2:10][c:9]1[c:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:19]2[c:18]([c:16]([CH3:17])[c:13]1[O:14][CH3:15])[CH2:23][O:22][C:20]2=[O:21]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10][CH:11]=[O:12])[c:13]([O:14][CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[C:20](=[O:21])[... | COCCOCOc1c(C/C=C(\C)CCC(=O)O)c(OC)c(C)c2c1C(=O)OC2 | COCCOCOc1c(CC=O)c(OC)c(C)c2c1C(=O)OC2 | null | null | null | Miscellaneous | Alkene oxidation to aldehyde | 148369763d5ac94fa638d0416b05b2817b88fbcf3e3881a34df5b1c1422931df | 8efb0e76025bf10ceb3c462bb2943eb84b6953d35e82203a100aa1bb9e5b03cd | O=C1OCc2ccccc21 | C/C(-C-C-C(=O)-[OH;D1;+0:1])=[CH;D2;+0:2]\[C:3]-[c:4]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | null | null | By following the procedure of part A and substituting methyl (E)-6-(4-t-butyldimethylsilyloxy-1,3-dihydro -6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate with (E)-6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl -3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, there was obtained 2-(1,3-dihy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | c1ccc2c(c1)COC2 | HO- | null | null | null | COCCOCOc1c(C/C=C(\C)CCC(=O)O)c(OC)c(C)c2c1C(=O)OC2>>COCCOCOc1c(CC=O)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f078921265d0411fa08bc67cd49cab1e | C=C(C)C(O)Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>COC(=O)C(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(C(=C)C)O)OC)C)=O>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OC)C)\C)OC)C)=O | [CH3:1][C:25]([Si:22]([O:21][c:20]1[c:12]([CH2:11][CH:10]([OH:2])[C:8](=[CH2:7])[CH3:9])[c:13]([O:14][CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[C:29](=[O:30])[O:31][CH2:32]2)([CH3:23])[CH3:24])([CH3:26])[CH3:28]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c... | C=C(C)C(O)Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | COC(=O)C(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | null | C(CC)(OC)(OC)OC.C(CC)(=O)O | Functional Group Addition | OtherReaction | 95879aa68e13a7c3887b644a0e5ab788bc8ccac1864a8b46ceb70548db1d9693 | c35876feeb8f837edfa28d6fabc0bcd11e4c5bd63ed79647940225e1df640f0b | O=C1OCc2ccccc21 | [#8:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[CH3;D1;+0:8].[C;D1;H3:9]-[C;H0;D3;+0:10](=[CH2;D1;+0:11])-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:14]-[c:15]>>[#8:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:16])-[C;D1;H3:7].[C;D1;H3:17]-[C:18](-[CH2;D2;+0... | null | [] | null | null | null | null | A solution of 4-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene (0.91 g) in trimethyl orthopropionate (25 ml) and propionic acid (0.08 ml) was heated to 110° C. for 2.5 hours. The solvents were evaporated under vacuum to afford methyl (E)-6-(4-tert-buty... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Vinyl.TMS ether protective group | Ester.TMS ether protective group | null | null | c1ccc2c(c1)COC2 | Other | C(CC)(OC)(OC)OC.C(CC)(=O)O | null | null | C=C(C)C(O)Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>C(CC)(OC)(OC)OC.C(CC)(=O)O>COC(=O)C(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4e1328b28d1a47029e53dfd91f1f4ad0 | COC(=O)C(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>COC(=O)C(C)C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OC)C)\C)OC)C)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OC)C)\C)OC)C)=O | CC(C)(C)[Si](C)(C)[O:14][c:13]1[c:12]([CH2:11]/[CH:10]=[C:8](/[CH2:7][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6])[CH3:9])[c:19]([O:20][CH3:21])[c:17]([CH3:18])[c:16]2[c:15]1[C:24](=[O:25])[O:23][CH2:22]2>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([OH:14])[c:15]2[c:16]([c:... | COC(=O)C(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | COC(=O)C(C)C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | O=C1OCc2ccccc21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#8:7]>>[#8:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | null | null | To methyl (E)-6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoate (0.8 g) in tetrahydrofuran (5 ml) was added 1N tetra-n-butylammonium fluoride in tetrahydrofuran (4 ml). After 10 minutes the solution was diluted with ice water and extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccc2c(c1)COC2 | Other | O1CCCC1 | null | null | COC(=O)C(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>O1CCCC1>COC(=O)C(C)C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-72415126fa004050bfea8158ceb7782c | COC(=O)C(C)C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>>COc1c(C)c2c(c(O)c1C/C=C(\C)CC(C)C(=O)O)C(=O)OC2 | Cl.OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OC)C)\C)OC)C)=O.[OH-].[Li+]>>OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)O)C)\C)OC)C)=O | C[O:20][C:18]([CH:16]([CH2:15]/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:21](=[O:22])[O:23][CH2:24]2)[CH3:14])[CH3:17])=[O:19]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH2:15][CH:16]([CH3:17])[C:18](=[O:19])[OH:... | COC(=O)C(C)C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | COc1c(C)c2c(c(O)c1C/C=C(\C)CC(C)C(=O)O)C(=O)OC2 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccccc21 | 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] | null | [] | null | null | 4 | HOUR | To methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoate (0.85 g) in methanol (10 ml) was added a solution of lithium hydroxide (0.4 g) in water (5 ml). After 4 hours at room temperature, the solution was poured into ice water, acidified with 10% aqueous hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)COC2 | Other | O.CO | null | 4 | COC(=O)C(C)C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>O.CO>COc1c(C)c2c(c(O)c1C/C=C(\C)CC(C)C(=O)O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4f4f7c5bfbac4cb282ab0edfc243fca8 | CC(C=O)=P(c1ccccc1)(c1ccccc1)c1ccccc1.COCCOCOc1c(CC=O)c(OC)c(C)c2c1C(=O)OC2>>COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CC=O.C1(=CC=CC=C1)P(=C(C=O)C)(C1=CC=CC=C1)C1=CC=CC=C1>>COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/C=O)\C | c1ccc(P(c2ccccc2)(c2ccccc2)=[C:12]([CH3:13])[CH:14]=[O:15])cc1.O=[CH:11][CH2:10][c:9]1[c:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:22]2[c:21]([c:19]([CH3:20])[c:16]1[O:17][CH3:18])[CH2:26][O:25][C:23]2=[O:24]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH:14]=[O:15... | CC(C=O)=P(c1ccccc1)(c1ccccc1)c1ccccc1.COCCOCOc1c(CC=O)c(OC)c(C)c2c1C(=O)OC2 | COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Wittig reaction with triphenylphosphorane | ba14f60c8faf1e2b5d258488ef5e81c88d381e470a98a19e511c94a7a3104695 | 3174a51604157c488f07402e36f994f716989b8fc10687ee243713b4cfbdb11a | O=C1OCc2ccccc21 | O=[CH;D2;+0:1]-[C:2]-[c:3].[C;D1;H3:4]-[C;H0;D3;+0:5](-[C:6]=[O;D1;H0:7])=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:4]/[C;H0;D3;+0:5](-[C:6]=[O;D1;H0:7])=[CH;D2;+0:1]\[C:2]-[c:3] | null | [] | null | null | null | null | A solution of 2-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy -7-methyl-3-oxoisobenzofuran-5-yl)acetaldehyde (10.3 g) and 2-(triphenyl-phosphoranylidene)-propionaldehyde (11.6 g) in toluene (250 ml) was refluxed for 7 hours. The solvent was removed under vacuum and the residue was chromatographed on silica gel, eluting... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Aldehyde | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2c(c1)COC2 | HO- | C1(=CC=CC=C1)C | null | null | CC(C=O)=P(c1ccccc1)(c1ccccc1)c1ccccc1.COCCOCOc1c(CC=O)c(OC)c(C)c2c1C(=O)OC2>C1(=CC=CC=C1)C>COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5345bf2b94bc498b82d222f982316189 | CCOC(=O)C(C)C.COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2>>CCOC(=O)C(C)(C)C(O)/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/C=O)\C.C(C)(C)NC(C)C.[Li]CCCC.[NH4+].[Cl-].C(C(C)C)(=O)OCC>>COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/C(C(C(=O)OCC)(C)C)O)\C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[CH3:8].[CH:9](=[O:10])/[C:11]([CH3:12])=[CH:13]/[CH2:14][c:15]1[c:16]([O:17][CH3:18])[c:19]([CH3:20])[c:21]2[c:22]([c:23]1[O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[C:31](=[O:32])[O:33][CH2:34]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[CH:9]([OH:1... | CCOC(=O)C(C)C.COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2 | CCOC(=O)C(C)(C)C(O)/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | null | null | C1CCOC1 | C-C Coupling | Aldol condensation | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | O=C1OCc2ccccc21 | [C;D1;H3:1]/[C:2](=[C:3]\[C:4]-[c:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12](-[C;D1;H3:13])-[C;D1;H3:14]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[CH;D3;+0:6](-[OH;D1;+0:7])/[C:2](-[C;D1;H3:1])=[C:3]/[C:4]-[c:5] | 87 | [{"value": 87.0, "product": "COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/C(C(C(=O)OCC)(C)C)O)\\C)OC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Freshly distilled diisopropylamine (0.425 ml) was dissolved in anhydrous THF (10 ml) and cooled to 0° C. n-BuLi (0.63 ml, 2.35M) was added slowly and the reaction was stirred at 0° C. for 20 minutes and cooled to -78°. Ethyl isobutyrate (0.200 ml) was added and the resulting solution was stirred at -78° C. for 40 minut... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccc2c(c1)COC2 | null | C1CCOC1 | 0 | 0.333333 | CCOC(=O)C(C)C.COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2>C1CCOC1>CCOC(=O)C(C)(C)C(O)/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c8fe2bc179014416806c17e5f7ee215d | CCOC(=O)C(C)(C)C(O)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>>COc1c(C)c2c(c(O)c1C/C=C(\C)C(O)C(C)(C)C(=O)O)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/C(C(C(=O)OCC)(C)C)O)\C)OC)C)=O>>OC1=C2C(OCC2=C(C(=C1C/C=C(/C(C(C(=O)O)(C)C)O)\C)OC)C)=O | CC[O:22][C:20]([C:17]([CH:15](/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:23](=[O:24])[O:25][CH2:26]2)[CH3:14])[OH:16])([CH3:18])[CH3:19])=[O:21]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH:15]([OH:16])[C:17]([CH... | CCOC(=O)C(C)(C)C(O)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | COc1c(C)c2c(c(O)c1C/C=C(\C)C(O)C(C)(C)C(=O)O)C(=O)OC2 | null | null | CCOCC.C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccccc21 | 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] | null | [] | null | null | null | null | By following the procedure of Example ZA-6A and substituting methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) 2,4-dimethyl-4-hexenoate with ethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,2,4-trimethyl-3-hydroxy-4-hexenoate and the corresponding compounds ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)COC2 | Other | CCOCC.C(C)(=O)OCC | null | null | CCOC(=O)C(C)(C)C(O)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>CCOCC.C(C)(=O)OCC>COc1c(C)c2c(c(O)c1C/C=C(\C)C(O)C(C)(C)C(=O)O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-80a07f86bd5b4e04b69809945bd1ada7 | CCOC(=O)CC(O)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.CI>>CCOC(=O)CC(OC)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)O)\C)OC)C)=O.CI>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)OC)\C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])/[C:10]([CH3:11])=[CH:12]/[CH2:13][c:14]1[c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]2[c:21]([c:22]1[O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[C:31](=[O:32])[O:33][CH2:34]2.I[CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([O:8][CH3:9]... | CCOC(=O)CC(O)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.CI | CCOC(=O)CC(OC)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | [Ag]=O | CC#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | O=C1OCc2ccccc21 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](-[OH;D1;+0:7])/[C:8](-[C;D1;H3:9])=[C:10]/[C:11]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](-[O;H0;D2;+0:7]-[CH3;D1;+0:1])/[C:8](-[C;D1;H3:9])=[C:10]/[C:11] | 60 | [{"value": 60.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)OC)\\C)OC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl (E)-6-(1,3-dihydro-4-tert -butyldimethylsilyloxy-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-4-methyl-4-hexenoate (974 mg) was dissolved in a 6:1 mixture of methyl iodide in CH3CN (25 ml). Silver oxide was then added (5.1 g) and the mixture heated at reflux for 24 hr. The mixture was cooled to room tem... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | c1ccc2c(c1)COC2 | HI | [Ag]=O.CC#N | null | null | CCOC(=O)CC(O)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.CI>[Ag]=O.CC#N>CCOC(=O)CC(OC)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-78e66f63118845168ca11d31beeffab3 | CCOC(=O)CC(OC)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>>COc1c(C)c2c(c(O)c1C/C=C(\C)C(CC(=O)O)OC)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)OC)\C)OC)C)=O>>OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)O)OC)\C)OC)C)=O | CC[O:19][C:17]([CH2:16][CH:15](/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:22](=[O:23])[O:24][CH2:25]2)[CH3:14])[O:20][CH3:21])=[O:18]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH:15]([CH2:16][C:17](=[O:18])[OH:19... | CCOC(=O)CC(OC)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | COc1c(C)c2c(c(O)c1C/C=C(\C)C(CC(=O)O)OC)C(=O)OC2 | null | null | CCCCCC.C(Cl)Cl | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccccc21 | 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] | null | [] | null | null | null | null | By following the procedure of Example ZA-6A and substituting methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) 2,4-dimethyl-4-hexenoate with ethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-methoxy-4-methyl-4-hexenoate and the corresponding compounds of Form... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)COC2 | Other | CCCCCC.C(Cl)Cl | null | null | CCOC(=O)CC(OC)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>CCCCCC.C(Cl)Cl>COc1c(C)c2c(c(O)c1C/C=C(\C)C(CC(=O)O)OC)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1cab9284e0e142118725aa659befdec5 | COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2>>COCCOCOc1c(C/C=C(\C)CO)c(OC)c(C)c2c1C(=O)OC2 | O.COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/C=O)\C.[BH4-].[Na+]>>COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CO)\C | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH:14]=[O:15])[c:16]([O:17][CH3:18])[c:19]([CH3:20])[c:21]2[c:22]1[C:23](=[O:24])[O:25][CH2:26]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH2:14][OH:15])[c:16]([O:17][CH3:18])[c:19... | COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2 | COCCOCOc1c(C/C=C(\C)CO)c(OC)c(C)c2c1C(=O)OC2 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=C1OCc2ccccc21 | [C;D1;H3:1]/[C:2](=[C:3]\[C:4]-[c:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[C;D1;H3:1]/[C:2](=[C:3]\[C:4]-[c:5])-[CH2;D2;+0:6]-[OH;D1;+0:7] | null | [] | null | null | null | null | To a solution of (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-enaldehyde (4.6 g) in methanol (60 ml) was added sodium borohydride (0.528 g). After one hour the reaction was added to water (250 ml) and extracted with ethyl acetate (2×150 ml). The extract was dried a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccc2c(c1)COC2 | null | CO | null | null | COCCOCOc1c(C/C=C(\C)C=O)c(OC)c(C)c2c1C(=O)OC2>CO>COCCOCOc1c(C/C=C(\C)CO)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3d832c1fcf3c483f83810b22f9dee1dd | COCCOCOc1c(C/C=C(\C)CO)c(OC)c(C)c2c1C(=O)OC2.O=C1CCC(=O)N1Br>>COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2 | BrN1C(CCC1=O)=O.COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CO)\C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CBr)\C | O[CH2:14]/[C:12](=[CH:11]/[CH2:10][c:9]1[c:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:22]2[c:21]([c:19]([CH3:20])[c:16]1[O:17][CH3:18])[CH2:26][O:25][C:23]2=[O:24])[CH3:13].O=C1CCC(=O)N1[Br:15]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[CH2:14][Br:15])[c:16]([O:17]... | COCCOCOc1c(C/C=C(\C)CO)c(OC)c(C)c2c1C(=O)OC2.O=C1CCC(=O)N1Br | COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | O=C1OCc2ccccc21 | O-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:7]>>[Br;H0;D1;+0:7]-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6] | null | [] | null | null | null | null | To a solution of (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-en-1-ol (4.6 g) in methylene chloride (100 ml) at 0° C. was added triphenylphosphine (3.64 g) then N-bromosuccinimide (2.48 g). After 15 minutes the solution was washed with 10% aqueous sodium bisulphite... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccc2c(c1)COC2 | HO- | C(Cl)Cl | null | null | COCCOCOc1c(C/C=C(\C)CO)c(OC)c(C)c2c1C(=O)OC2.O=C1CCC(=O)N1Br>C(Cl)Cl>COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-974ff8f64ce5424998e02f92638f72db | CCOC(C)=O.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2.[NH4+]>>CCOC(=O)C(N)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | [NH4+].[Cl-].COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CBr)\C.C(C)(=O)OCC.[Li]CCCC.C(C)(C)NC(C)C>>COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)N)\C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].Br[CH2:8]/[C:9]([CH3:10])=[CH:11]/[CH2:12][c:13]1[c:14]([O:15][CH3:16])[c:17]([CH3:18])[c:19]2[c:20]([c:21]1[O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[C:29](=[O:30])[O:31][CH2:32]2.[NH4+:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH2:7])[CH2:8]/[C:9]([CH3:10])=[CH:11]/[... | CCOC(C)=O.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2.[NH4+] | CCOC(=O)C(N)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | null | null | CN(C)P(=O)(N(C)C)N(C)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 021424c3b860edcb551eeea16c22a1ab914c9407329c37932b427a0488e708d5 | 4ccd83de18159de0cdb89422fce5446da660f78eea0800945f87eaa501327824 | O=C1OCc2ccccc21 | Br-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6].[C:7]-[#8:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11].[NH4+;D0:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:11])-[CH;D3;+0:10](-[NH2;D1;+0:12])-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6] | 63 | [{"value": 63.0, "product": "COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)N)\\C)OC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Freshly distilled diisopropylamine (0.435 ml) was dissolved in THF (10 ml). The solution was cooled to 0° C. and n-BuLi (1.3 ml, 2.38M) was added. The mixture was stirred at 0° C. for 20 minutes. The ice-bath was replaced by a dry ice-acetone bath and a solution of ethyl benzylidine glycinate (0.445 g) in THF (2 ml) wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Primary amine | null | null | c1ccc2c(c1)COC2 | HBr | CN(C)P(=O)(N(C)C)N(C)C.C1CCOC1 | 0 | 0.333333 | CCOC(C)=O.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2.[NH4+]>CN(C)P(=O)(N(C)C)N(C)C.C1CCOC1>CCOC(=O)C(N)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2f7d3cefcf884ad1aca8cee6ff44c882 | CCOC(=O)C(N)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2.CS(=O)(=O)Cl>>CCOC(=O)C(C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O)NS(C)(=O)=O | COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)N)\C)OC)C)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)NS(=O)(=O)C)\C)OC)C)=O | COCCOC[O:14][c:13]1[c:12]([CH2:11]/[CH:10]=[C:8](/[CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH2:26])[CH3:9])[c:19]([O:20][CH3:21])[c:17]([CH3:18])[c:16]2[c:15]1[C:24](=[O:25])[O:23][CH2:22]2.Cl[S:27]([CH3:28])(=[O:29])=[O:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c... | CCOC(=O)C(N)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2.CS(=O)(=O)Cl | CCOC(=O)C(C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O)NS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | OtherReaction | f64aef4580e1e6ad92b3d71ef18da39eb289cd14c0135adab56405f63c8662ac | d8b7bf55ed6b85f502ad9039ef600b9b0dfa1f31935b329cea56a7ab8526271d | O=C1OCc2ccccc21 | C-O-C-C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#8:7].[C:8]=[C:9]/[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16].Cl-[S;H0;D4;+0:17](-[C;D1;H3:18])(=[O;D1;H0:19])=[O;D1;H0:20]>>[#8:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3].[C:8]=[C:9]/[C:10]-[C:11](-[NH;D2;+0:12]-[S... | 82 | [{"value": 82.0, "product": "OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)NS(=O)(=O)C)\\C)OC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Ethyl (E)-6-(4-methoxyethoxymethoxy-1,3-dihydro-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2-amino-4-methyl-4-hexenoate (373 mg) was dissolved in CH2Cl2 (10 ml), cooled to 0° C., and triethylamine (0.17 ml) and methylsulfonyl chloride (0.09 ml) were added. The mixture was stirred at 0° C. for 1 hour and at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Sulfonyl halide | Sulfonamide.Aromatic alcohol | null | null | c1ccc2c(c1)COC2 | HCl | C(Cl)Cl | 0 | 2 | CCOC(=O)C(N)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2.CS(=O)(=O)Cl>C(Cl)Cl>CCOC(=O)C(C/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O)NS(C)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8e444441d4214018adf3d389f94b601f | CCOC(=O)C(C)C.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2>>CCOC(=O)C(C)(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | [NH4+].[Cl-].C(C)(C)[N-]C(C)C.[Li+].C(C(C)C)(=O)OCC.COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CBr)\C>>COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)(C)C)\C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[CH3:8].Br[CH2:9]/[C:10]([CH3:11])=[CH:12]/[CH2:13][c:14]1[c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]2[c:21]([c:22]1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[C:30](=[O:31])[O:32][CH2:33]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[CH2:9]/[C:10]([CH... | CCOC(=O)C(C)C.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2 | CCOC(=O)C(C)(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | null | null | CN(C)P(=O)(N(C)C)N(C)C.C(Cl)Cl.CCOC(=O)C.C1CCOC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C1OCc2ccccc21 | Br-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[C;D1;H3:12])-[C;D1;H3:13]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D4;+0:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6] | 74 | [{"value": 74.0, "product": "COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)(C)C)\\C)OC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 40 | MINUTE | A freshly prepared solution of lithium diisopropylamide (2.8 mmol/10 ml THF) was cooled to -78° C. and ethyl isobutyrate (0.75 ml) was added slowly. The solution was stirred at -78° C. for 40 minutes and then a solution of (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2-methylbu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1ccc2c(c1)COC2 | HBr | CN(C)P(=O)(N(C)C)N(C)C.C(Cl)Cl.CCOC(=O)C.C1CCOC1 | -78 | 0.666667 | CCOC(=O)C(C)C.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2>CN(C)P(=O)(N(C)C)N(C)C.C(Cl)Cl.CCOC(=O)C.C1CCOC1>CCOC(=O)C(C)(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c4e229a8b75d49bea2d79b6f95430408 | CCOC(=O)C(C)(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2>>COCCOCOc1c(C/C=C(\C)CC(C)(C)C(=O)O)c(OC)c(C)c2c1C(=O)OC2 | COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)(C)C)\C)OC)C)=O>>COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)O)(C)C)\C)OC)C)=O | CC[O:20][C:18]([C:15]([CH2:14]/[C:12](=[CH:11]/[CH2:10][c:9]1[c:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:27]2[c:26]([c:24]([CH3:25])[c:21]1[O:22][CH3:23])[CH2:31][O:30][C:28]2=[O:29])[CH3:13])([CH3:16])[CH3:17])=[O:19]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[c:9]([CH2:10]/[CH:11]=[C:12](\[CH3:13])[C... | CCOC(=O)C(C)(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2 | COCCOCOc1c(C/C=C(\C)CC(C)(C)C(=O)O)c(OC)c(C)c2c1C(=O)OC2 | null | null | CCCCCC.C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccccc21 | 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] | null | [] | null | null | null | null | By following the procedure of Example ZA-6A and substituting methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -2,4-dimethyl-4-hexenoate with ethyl (E)-6-(4-methoxyethoxymethoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,2,4-trimethyl -4-hexenoate and compounds of Formula 10... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)COC2 | Other | CCCCCC.C(C)(=O)OCC | null | null | CCOC(=O)C(C)(C)C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2>CCCCCC.C(C)(=O)OCC>COCCOCOc1c(C/C=C(\C)CC(C)(C)C(=O)O)c(OC)c(C)c2c1C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6b852ad794654a8dae8183b02d827428 | CCOC(=O)CP(=O)(OC)OC.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2>>CCOC(=O)C(C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2)P(=O)(OC)OC | COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CBr)\C.COP(=O)(OC)CC(=O)OCC.[H-].[Na+]>>COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)P(=O)(OC)OC)\C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][P:32](=[O:33])([O:34][CH3:35])[O:36][CH3:37].Br[CH2:7]/[C:8]([CH3:9])=[CH:10]/[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c:16]([CH3:17])[c:18]2[c:19]([c:20]1[O:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:28](=[O:29])[O:30][CH2:31]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7... | CCOC(=O)CP(=O)(OC)OC.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2 | CCOC(=O)C(C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2)P(=O)(OC)OC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C1OCc2ccccc21 | Br-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6].[#8:7]-[#15:8](-[#8:9])(=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[#8:7]-[#15:8](-[#8:9])(=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5]-[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | null | [] | null | null | 10 | MINUTE | To a solution of ethyl dimethylphosphonoacetate (135 mg) in DMF (5 ml) at 0° was added 50% NaH/oil (33 mg), and the mixture stirred for 10 minutes. (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy7-methyl -3-oxoisobenzofuran-5-yl)-2-methylbut-2-enyl bromide (600 mg) was added at the same temperature and allowed to r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1ccc2c(c1)COC2 | HBr | CN(C)C=O | null | 0.166667 | CCOC(=O)CP(=O)(OC)OC.COCCOCOc1c(C/C=C(\C)CBr)c(OC)c(C)c2c1C(=O)OC2>CN(C)C=O>CCOC(=O)C(C/C(C)=C/Cc1c(OC)c(C)c2c(c1OCOCCOC)C(=O)OC2)P(=O)(OC)OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d3b13ccbffa14eb7a6ef6bc77b1e81ca | COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)C(=O)OC(C)(C)C)C(=O)OC2>>COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)C(=O)O)C(=O)OC2 | CS(=O)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(\C(=O)OC(C)(C)C)/Cl)OC)C)=O>>CS(=O)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(\C(=O)O)/Cl)OC)C)=O | CC(C)(C)[O:21][C:19](/[C:17](=[CH:16]\[CH2:15][c:14]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[O:9][S:10]([CH3:11])(=[O:12])=[O:13])[C:22](=[O:23])[O:24][CH2:25]2)[Cl:18])=[O:20]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10]([CH3:11])(=[O:12])=[O:13])[c:14]1[CH2:15]/[CH:16]=[C:17](/[Cl:18])[C... | COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)C(=O)OC(C)(C)C)C(=O)OC2 | COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)C(=O)O)C(=O)OC2 | null | null | C(Cl)Cl.FC(C(=O)O)(F)F | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1OCc2ccccc21 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4](-[Cl;D1;H0:5])=[C:6]\[C:7]>>[C:7]/[C:6]=[C:4](/[Cl;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 89.4 | [{"value": 89.4, "product": "CS(=O)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(\\C(=O)O)/Cl)OC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | t-Butyl (E)-4-(1,3-dihydro-4-methanesulfonyloxy-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2-chlorobut-2-enoate (2.7 g) was dissolved in freshly distilled trifluoroacetic acid (25 ml) and stirred at room temperature for 90 minutes. The mixture was diluted with CH2Cl2 (25 ml) and evaporated to dryness and repeated unt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2c(c1)COC2 | Other | C(Cl)Cl.FC(C(=O)O)(F)F | null | 1.5 | COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)C(=O)OC(C)(C)C)C(=O)OC2>C(Cl)Cl.FC(C(=O)O)(F)F>COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)C(=O)O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-345a467f4df54eeeb4868c55d548a875 | CCOC(=O)CC(=O)OCC.COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)CBr)C(=O)OC2>>CCOC(=O)C(C/C(Cl)=C\Cc1c(OC)c(C)c2c(c1OS(C)(=O)=O)C(=O)OC2)C(=O)OCC | CS(=O)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(\CBr)/Cl)OC)C)=O.C(CC(=O)OCC)(=O)OCC.[H-].[Na+]>>CS(=O)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(\CC(C(=O)OCC)C(=O)OCC)/Cl)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:30](=[O:31])[O:32][CH2:33][CH3:34].Br[CH2:7]/[C:8]([Cl:9])=[CH:10]\[CH2:11][c:12]1[c:13]([O:14][CH3:15])[c:16]([CH3:17])[c:18]2[c:19]([c:20]1[O:21][S:22]([CH3:23])(=[O:24])=[O:25])[C:26](=[O:27])[O:28][CH2:29]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7]/[C:8]([Cl:9])=[CH:1... | CCOC(=O)CC(=O)OCC.COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)CBr)C(=O)OC2 | CCOC(=O)C(C/C(Cl)=C\Cc1c(OC)c(C)c2c(c1OS(C)(=O)=O)C(=O)OC2)C(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | O=C1OCc2ccccc21 | Br-[CH2;D2;+0:1]/[C:2](-[Cl;D1;H0:3])=[C:4]\[C:5]-[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]/[C:2](-[Cl;D1;H0:3])=[C:4]\[C:5]-[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 57.5 | [{"value": 57.5, "product": "CS(=O)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(\\CC(C(=O)OCC)C(=O)OCC)/Cl)OC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Diethyl malonate (113 mg) was added to a suspension of 50% NaH (35 mg) in THF (3 ml) at 0° C. and the mixture stirred for 30 minutes. To this solution was added (E)-4-(1,3-dihydro-4-methanesulfonyloxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-bromo-2-chlorobut-2-ene (280 mg) in THF (10 ml). The ice bath was removed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccc2c(c1)COC2 | HBr | C1CCOC1 | null | 0.5 | CCOC(=O)CC(=O)OCC.COc1c(C)c2c(c(OS(C)(=O)=O)c1C/C=C(/Cl)CBr)C(=O)OC2>C1CCOC1>CCOC(=O)C(C/C(Cl)=C\Cc1c(OC)c(C)c2c(c1OS(C)(=O)=O)C(=O)OC2)C(=O)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a0f89bc489b2437c8013eb1e5e984063 | C=C(C)C(O)Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.COC(CCCBr)(OC)OC>>COC(=O)C(CCBr)CC(C)=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | C(CC)(=O)O.[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(C(=C)C)O)OC)C)=O.COC(CCCBr)(OC)OC>>BrCCC(C(=O)OC)CC(=CCC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C)C | O[CH:12]([C:10](=[CH2:9])[CH3:11])[CH2:13][c:14]1[c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]2[c:21]([c:22]1[O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[C:31](=[O:32])[O:33][CH2:34]2.CO[C:3]([O:2][CH3:1])([O:4]C)[CH2:5][CH2:6][CH2:7][Br:8]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][Br:8])[C... | C=C(C)C(O)Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.COC(CCCBr)(OC)OC | COC(=O)C(CCBr)CC(C)=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | null | null | Acylation | OtherReaction | 9bf7c01f3fba65ea0cdc8ffe3c902a1716bf21528f214415a6c56fa7fdc4a193 | c738d9923191e0b9d66534a280f828a4b3af1448c6f50b64792c7c450a24abfc | O=C1OCc2ccccc21 | C-O-[C;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[CH2;D2;+0:4]-[C:5]-[C:6])-[O;H0;D2;+0:7]-C.O-[CH;D3;+0:8](-[C:9]-[c:10])-[C;H0;D3;+0:11](-[C;D1;H3:12])=[CH2;D1;+0:13]>>[C:6]-[C:5]-[CH;D3;+0:4](-[CH2;D2;+0:13]-[C;H0;D3;+0:11](-[C;D1;H3:12])=[CH;D2;+0:8]-[C:9]-[c:10])-[C;H0;D3;+0:1](=[O;H0;D1;+0:7])-[#8:2]-[C;D1;H3:3] | null | [] | null | null | null | null | A solution of trimethyl 4-bromoorthobutyrate (20 ml), propionic acid (0.22 ml) and 4-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene (3.18 g) was heated at 110° C. in a three-necked flash with a slow nitrogen stream passing over the reaction mixture. Af... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol.Vinyl | Ester | null | null | c1ccc2c(c1)COC2 | HO- | null | null | null | C=C(C)C(O)Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.COC(CCCBr)(OC)OC>>COC(=O)C(CCBr)CC(C)=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0ae8071f8fc94140b0001a99db3d857b | CC(C)NC(C)C.COC(=O)C(CCBr)CC(C)=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>CC(C)[N-]C(C)C.COC(=O)C1(CC(C)=CCc2c(OC)c(C)c3c(c2O[Si](C)(C)C(C)(C)C)C(=O)OC3)CC1 | C(C)(C)NC(C)C.C(CCC)[Li].BrCCC(C(=O)OC)CC(=CCC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C)C.[Li+].CC(C)[N-]C(C)C>>C(C)(C)[N-]C(C)C.[Li+].COC(=O)C1(CC1)CC(=CCC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C)C | [CH3:1][CH:2]([CH3:3])[NH:4][CH:5]([CH3:6])[CH3:7].Br[CH2:40][CH2:39][CH:12]([C:10]([O:9][CH3:8])=[O:11])[CH2:13][C:14]([CH3:15])=[CH:16][CH2:17][c:18]1[c:19]([O:20][CH3:21])[c:22]([CH3:23])[c:24]2[c:25]([c:26]1[O:27][Si:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[CH3:34])[C:35](=[O:36])[O:37][CH2:38]2>>[CH3:1][C... | CC(C)NC(C)C.COC(=O)C(CCBr)CC(C)=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | CC(C)[N-]C(C)C.COC(=O)C1(CC(C)=CCc2c(OC)c(C)c3c(c2O[Si](C)(C)C(C)(C)C)C(=O)OC3)CC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 954c2f92326cf05ea81d7d009ca43bf34835471a23144b5f5879cbf4cbe25ec0 | 6e06776731664fe9861b643a9b8e2db1cb60f0e675c8f3b0a8d851226bbe26c6 | O=C1OCc2ccc(CC=CCC3CC3)cc21 | Br-[CH2;D2;+0:1]-[C:2]-[CH;D3;+0:3](-[C:4]-[C:5](-[C;D1;H3:6])=[C:7]-[C:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12].[C;D1;H3:13]-[C:14](-[C;D1;H3:15])-[NH;D2;+0:16]-[C:17](-[C;D1;H3:18])-[C;D1;H3:19]>>[C;D1;H3:13]-[C:14](-[C;D1;H3:15])-[N-;H0;D2:16]-[C:17](-[C;D1;H3:18])-[C;D1;H3:19].[C:8]-[C:7]=[C:5](-[C;D1;H3:6])-[... | null | [] | -70 | CELSIUS | 50 | MINUTE | A solution of lithium diisopropyl amide was prepared from diisopropyl amine (2.24 ml) and n-butyllithium (6.4 ml, 2.5N) in THF (60 ml) and cooled to -70° C. Methyl 2-(2-bromoethyl)-6-(4-t-butyldimethylsiloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran -5-yl)-4-methyl-hex-4-enoate (2.66 g) in THF (12 ml was added ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Ester | null | C1CC1 | c1ccc2c(c1)COC2.C1CC1 | HBr | C1CCOC1 | -70 | 0.833333 | CC(C)NC(C)C.COC(=O)C(CCBr)CC(C)=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>C1CCOC1>CC(C)[N-]C(C)C.COC(=O)C1(CC(C)=CCc2c(OC)c(C)c3c(c2O[Si](C)(C)C(C)(C)C)C(=O)OC3)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d4d6d955703f412fbc9575b9b91423d7 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl>>COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)Cl)C(=O)OC2 | CC1=C2C(=C(C(=C1OC)C/C=C(\C)/CCC(=O)O)O)C(=O)OC2.CN(C=O)C.S(=O)(Cl)Cl>>OC1=C2C(OCC2=C(C(=C1CC=C(CCC(=O)Cl)C)OC)C)=O | O[C:17]([CH2:16][CH2:15]/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:20](=[O:21])[O:22][CH2:23]2)[CH3:14])=[O:18].O=S(Cl)[Cl:19]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11][CH:12]=[C:13]([CH3:14])[CH2:15][CH2:16][C:17](=[O:18])[Cl:19])[C:20](... | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl | COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)Cl)C(=O)OC2 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C1OCc2ccccc21 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]\[C:6]=[C:7]>>[C:7]=[C:6]-[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | A solution of mycophenolic acid (320 g, 1 mol) and dimethylformamide (0.1 g) in dichloromethane (3.2L) at reflux was treated dropwise with thionyl chloride (82 mL, 1.12 mol). After one hour additional heating at reflux, the volatiles were distilled at reduced pressure leaving a gray solid residue of (E) 6-(1,3-dihydro-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)COC2 | HCl | ClCCl | null | null | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl>ClCCl>COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)Cl)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d10d3d4f2cce4f3e823df84d28be081a | COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)Cl)C(=O)OC2.O=C1N[C@@H](Cc2ccccc2)CO1>>COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2 | Cl.OC1=C2C(OCC2=C(C(=C1CC=C(CCC(=O)Cl)C)OC)C)=O.C(CCC)[Li].CCCCCC.C(C1=CC=CC=C1)[C@@H]1NC(OC1)=O.C(C)(C)(C)O>>C(C1=CC=CC=C1)C1N(C(OC1)=O)C(CC\C(=C\CC=1C(=C2C(OCC2=C(C1OC)C)=O)O)\C)=O | Cl[C:17]([CH2:16][CH2:15][C:13](=[CH:12][CH2:11][c:10]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:32](=[O:33])[O:34][CH2:35]2)[CH3:14])=[O:18].[NH:19]1[C:20](=[O:21])[O:22][CH2:23][C@@H:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c... | COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)Cl)C(=O)OC2.O=C1N[C@@H](Cc2ccccc2)CO1 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2 | null | null | O1CCCC1.C(C)(=O)OCC | Protection | N-alkylation of secondary amines with alkyl halides | 90b874b95a490ba678a8102349b0a4dbcd41213027fb4e6cf3a650d8fd23bd0d | 4e5209ce9341ab4af6dffbdfa22c50d4dc790b976013dec4e496751ff4457c48 | O=C1OCc2ccc(CC=CCCC(=O)N3C(=O)OCC3Cc3ccccc3)cc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[C:6].[O;D1;H0:7]=[C:8]1-[#8:9]-[C:10]-[C@H;D3;+0:11](-[C:12]-[c:13])-[NH;D2;+0:14]-1>>[C:6]=[C:5]/[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:8](=[O;D1;H0:7])-[#8:9]-[C:10]-[CH;D3;+0:11]-1-[C:12]-[c:13] | null | [] | 0 | CELSIUS | null | null | A solution of (S)-4-benzyl-2-oxazolidinone (177.4 g, 1 mol) and t-butyl alcohol (74.1 g , 1 mol) in anhydrous tetrahydrofuran (2L) was cooled to -78° C. A 1.6M solution of n-butyllithium in hexane (1280 mL, 2 mol) was added maintaining a temperature below -30° C. After recooling to -78° C. the (E) 6-(1,3-dihydro-4-hydr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester | Carbamic ester.Substituted dicarboximide | C1COCN1 | C1COC[NH]1 | C1COC[NH]1.c1ccccc1.c1ccc2c(c1)COC2 | HCl | O1CCCC1.C(C)(=O)OCC | 0 | null | COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)Cl)C(=O)OC2.O=C1N[C@@H](Cc2ccccc2)CO1>O1CCCC1.C(C)(=O)OCC>COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a76e7895a60a43e49f3e09dc222840eb | CI.COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2.C[Si](C)(C)[N-][Si](C)(C)C>>COc1c(C)c2c(c(O)c1C/C=C(\C)CC(C)C(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2.COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2 | Cl.C(C1=CC=CC=C1)C1N(C(OC1)=O)C(CC\C(=C\CC=1C(=C2C(OCC2=C(C1OC)C)=O)O)\C)=O.IC.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>C(C1=CC=CC=C1)C1N(C(OC1)=O)C(CC\C(=C\CC=1C(=C2C(OCC2=C(C1OC)C)=O)O)\C)=O.C(C1=CC=CC=C1)C1N(C(OC1)=O)C(C(C\C(=C\CC=1C(=C2C(OCC2=C(C1OC)C)=O)O)\C)C)=O | I[CH3:17].[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:47]/[CH:48]=[C:49](\[CH3:50])[CH2:51][CH2:52][C:53](=[O:54])[N:55]1[C:56](=[O:57])[O:58][CH2:59][CH:60]1[CH2:61][c:62]1[cH:63][cH:64][cH:65][cH:66][cH:67]1)[C:68](=[O:69])[O:70][CH2:71]2.[Si]([CH3:11])([N-:20][Si]([CH3:24])([CH3:26])[CH3:42]... | CI.COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2.C[Si](C)(C)[N-][Si](C)(C)C | COc1c(C)c2c(c(O)c1C/C=C(\C)CC(C)C(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2.COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | c3747f16c99e5a8882af06091809359bc45494249716c48d4f2edbc76532e2aa | 6086e6621f5fe9e2ec64c99724be0620d1ebc7e7a8ff5acda211b311ca7cf66b | O=C1OCc2ccc(CC=CCCC(=O)N3C(=O)OCC3Cc3ccccc3)cc21.O=C1OCc2ccc(CC=CCCC(=O)N3C(=O)OCC3Cc3ccccc3)cc21 | I-[CH3;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]/[C:7](-[C;D1;H3:8])=[C:9]/[CH2;D2;+0:10]-[c;H0;D3;+0:11]1:[c:12](-[#8:13]):[c:14](-[C;D1;H3:15]):[c;H0;D3;+0:16]2:[c;H0;D3;+0:17](:[c:18]:1-[O;D1;H1:19])-[C;H0;D3;+0:20](=[O;D1;H0:21])-[#8:22]-[CH2;D2;+0:23]-2.[CH3;D1;+0:24]-[Si](-[CH3;D1;+0:25])(-[CH3;D1;+0:26])-[... | null | [] | -30 | CELSIUS | 15 | MINUTE | A 1M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.43L, 0.43 mol) was cooled to -78° C. and treated dropwise with a precooled solution of (S) 4-benzyl-3-[(E) 6-(1,3-dihydro-4-hydroxy -6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoyl]-2-oxazolidinone (86 g, 0.179 mol) in tetrahydrofura... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Silyl protective group.Silyl protective group | Carbamic ester.Ester.Ester.Ether.Ether.Substituted dicarboximide.Aromatic alcohol | c1ccc2c(c1)COC2 | C1COC[NH]1.c1ccccc1.c1ccc2c(c1)COC2.c1ccc2c(c1)COC2 | C1COC[NH]1.c1ccccc1.c1ccc2c(c1)COC2.C1COC[NH]1.c1ccccc1.c1ccc2c(c1)COC2 | I- | O1CCCC1 | -30 | 0.25 | CI.COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2.C[Si](C)(C)[N-][Si](C)(C)C>O1CCCC1>COc1c(C)c2c(c(O)c1C/C=C(\C)CC(C)C(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2.COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)N1C(=O)OCC1Cc1ccccc1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3c98506f7b5947428a6899a4897143df | COc1c(C)c2c(c(O)c1CC=C(C)CC(C)C(=O)O)C(=O)OC2>>COc1c(C)c2c(c(O)c1CC=C(C)CC(C)C(=O)O)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1CC=C(CC(C(=O)O)C)C)OC)C)=O.CC(C1=CC=CC=C1)N>>CC(C1=CC=CC=C1)N.OC1=C2C(OCC2=C(C(=C1CC=C(CC(C(=O)O)C)C)OC)C)=O | [CH3:10][O:11][c:12]1[c:13]([CH3:14])[c:15]2[c:16]([c:17]([OH:18])[c:19]1[CH2:20][CH:21]=[C:22]([CH3:23])[CH2:24][CH:25]([CH3:26])[C:27](=[O:28])[OH:29])[C:30](=[O:31])[O:32][CH2:33]2>>[CH3:10][O:11][c:12]1[c:13]([CH3:14])[c:15]2[c:16]([c:17]([OH:18])[c:19]1[CH2:20][CH:21]=[C:22]([CH3:23])[CH2:24][CH:25]([CH3:26])[C:27... | COc1c(C)c2c(c(O)c1CC=C(C)CC(C)C(=O)O)C(=O)OC2 | COc1c(C)c2c(c(O)c1CC=C(C)CC(C)C(=O)O)C(=O)OC2 | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1OCc2ccccc21 | null | null | [] | null | null | null | null | A solution of the 85:13 acid mixture(E) 6-(1,3-dihydro-4-hydroxy -6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoic acid (810 g, 2.4 mol,) was dissolved in acetone (16L) at 40° C. and (+)-α-methylbenzylamine (800 g, 6.6 mol) was added. Upon cooling, the salt crystallized and was collected by filtratio... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)COC2 | null | CC(=O)C | null | null | COc1c(C)c2c(c(O)c1CC=C(C)CC(C)C(=O)O)C(=O)OC2>CC(=O)C>COc1c(C)c2c(c(O)c1CC=C(C)CC(C)C(=O)O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a413010b44c54d4998306c0743d3f4dd | COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)C1=CCCC1)C(=O)OC2>>COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(=O)C1=CCCC1)C(=O)OC2 | C(C)N(CC)CC.[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(O)C1=CCCC1)OC)C)=O.FC(C(=O)OC(C(F)(F)F)=O)(F)F.CS(=O)C>>C1(=CCCC1)C(=O)CC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]1[CH2:18][CH:19]([OH:20])[C:21]1=[CH:22][CH2:23][CH2:24][CH2:25]1)[C:26](=[O:27])[O:28][CH2:29]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])(... | COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)C1=CCCC1)C(=O)OC2 | COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(=O)C1=CCCC1)C(=O)OC2 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(Cc1ccc2c(c1)C(=O)OC2)C1=CCCC1 | [C:1]-[C:2]=[C:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6]-[c:7])-[C:8]>>[C:1]-[C:2]=[C:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[c:7])-[C:8] | 82.9 | [{"value": 82.9, "product": "C1(=CCCC1)C(=O)CC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 30 | MINUTE | Trifluoroacetic anhydride (1.6 ml) in methylene chloride (3.6 ml) was added dropwise to dimethyl sulfoxide (1.05 ml) and CH2Cl2 (7.5 ml) under nitrogen over 5 minutes at -60° C. and stirred for 30 minutes. After addition of (±)-2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-1-c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1=CCCC1.c1ccc2c(c1)COC2 | null | C(Cl)Cl | -40 | 0.5 | COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)C1=CCCC1)C(=O)OC2>C(Cl)Cl>COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(=O)C1=CCCC1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0b6617e9cfd7449aaea81f512395c478 | CC(C)(C)C(=O)O.CCC(CC)(CC)C([O-])([O-])[O-].COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)C1=CCCC1)C(=O)OC2>>CCOC(=O)CC1CCC/C1=C\Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(O)C1=CCCC1)OC)C)=O.C(C(C)(C)C)(=O)O.C(C)C(C([O-])([O-])[O-])(CC)CC>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C\C=C/1\C(CCC1)CC(=O)OCC)OC)C)=O | C[C:6](C)(C)[C:4]([OH:3])=[O:5].CCC(CC)(C([O-])([O-])[O-])[CH2:2][CH3:1].O[CH:12]([C:11]1=[CH:7][CH2:8][CH2:9][CH2:10]1)[CH2:13][c:14]1[c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]2[c:21]([c:22]1[O:23][Si:24]([CH3:25])([CH3:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[C:31](=[O:32])[O:33][CH2:34]2>>[CH3:1][CH2:2][O:3][C:4](=... | CC(C)(C)C(=O)O.CCC(CC)(CC)C([O-])([O-])[O-].COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)C1=CCCC1)C(=O)OC2 | CCOC(=O)CC1CCC/C1=C\Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | edea5afb4f08e3f70490ee1fcf435c71451d86fc16b124dbfe27b4c4de1bc2d7 | 505f7b4da8def84a80ac616845cb7b0566b14f3232b5b9d3480d84d3e0d284a0 | O=C1OCc2ccc(CC=C3CCCC3)cc21 | C-C-C(-C-C)(-[CH2;D2;+0:1]-[C;D1;H3:2])-C(-[O-])(-[O-])-[O-].C-[C;H0;D4;+0:3](-C)(-C)-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6].O-[CH;D3;+0:7](-[C:8]-[c:9])-[C;H0;D3;+0:10]1=[CH;D2;+0:11]-[C:12]-[C:13]-[C:14]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:3]-[CH;D3;+0:11]1-[C:12]-[C:13]-[C:14]/[C;H0;... | null | [] | 100 | CELSIUS | null | null | A solution of 1-[2-(4-tert-butyldimethylsilyloxy-1,3-dihydro -6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-1-hydroxyeth-1-yl]cyclopent-1-ene (0.22 g) in triethylorthoacetate (10 ml) was treated with pivalic acid (0.010 g) and then heated to 100° C., and maintained at that temperature for 18 hours. After cooling to ambie... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | C1=CCCC1 | C1CCCC1 | C1CCCC1.c1ccc2c(c1)COC2 | HO- | C(C)(=O)OCC | 100 | null | CC(C)(C)C(=O)O.CCC(CC)(CC)C([O-])([O-])[O-].COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)C1=CCCC1)C(=O)OC2>C(C)(=O)OCC>CCOC(=O)CC1CCC/C1=C\Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-089ee3ae5afb430eb9502365490c6f0d | CCOC(=O)C[C@@H]1CCC/C1=C\Cc1c(O)c2c(c(C)c1OC)COC2=O.CI>>CCOC(=O)C(C)[C@@H]1CCC/C1=C\Cc1c(O)c2c(c(C)c1OC)COC2=O | [Cl-].[NH4+].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].OC1=C2C(OCC2=C(C(=C1C\C=C/1\[C@@H](CCC1)CC(=O)OCC)OC)C)=O.CI>>OC1=C2C(OCC2=C(C(=C1C\C=C/1\[C@@H](CCC1)C(C(=O)OCC)C)OC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@@H:8]1[CH2:9][CH2:10][CH2:11]/[C:12]1=[CH:13]\[CH2:14][c:15]1[c:16]([OH:17])[c:18]2[c:19]([c:20]([CH3:21])[c:22]1[O:23][CH3:24])[CH2:25][O:26][C:27]2=[O:28].I[CH3:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[C@@H:8]1[CH2:9][CH2:10][CH2:11]/[C:12]1=[CH:13]\[CH2:14][c:15]1... | CCOC(=O)C[C@@H]1CCC/C1=C\Cc1c(O)c2c(c(C)c1OC)COC2=O.CI | CCOC(=O)C(C)[C@@H]1CCC/C1=C\Cc1c(O)c2c(c(C)c1OC)COC2=O | null | null | O1CCCC1.CN1C(N(CCC1)C)=O.C(C)(=O)OCC | C-C Coupling | Methylation with MeI_secondary | 4a52ebe9ffae5bdd307b0b4ac6a7069bc533ab8d42293ed2712c32b846010273 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | O=C1OCc2ccc(CC=C3CCCC3)cc21 | I-[CH3;D1;+0:1].[C:2]/[C:3](=[C:4]\[C:5])-[C:6](-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C:12]>>[C:2]/[C:3](=[C:4]\[C:5])-[C:6](-[CH;D3;+0:7](-[CH3;D1;+0:1])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C:12] | null | [] | null | null | 30 | MINUTE | To a solution of 1M sodium bis(trimethylsilyl)amide in tetrahydrofuran (31.7 ml ) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2.74 ml) at -78° C. was added ethyl (E) 2-{2-[2-(1,3-dihydro -4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) ethylidene]cyclopent -1-(S)-yl}acetate (3.39 g) in tetrahydrofuran... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | C1CCCC1.c1ccc2c(c1)COC2 | HI | O1CCCC1.CN1C(N(CCC1)C)=O.C(C)(=O)OCC | null | 0.5 | CCOC(=O)C[C@@H]1CCC/C1=C\Cc1c(O)c2c(c(C)c1OC)COC2=O.CI>O1CCCC1.CN1C(N(CCC1)C)=O.C(C)(=O)OCC>CCOC(=O)C(C)[C@@H]1CCC/C1=C\Cc1c(O)c2c(c(C)c1OC)COC2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9607c20c20c74c6fbe9c3af9fb2b3115 | CCC=O.COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=O)C(=O)OC2>>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=C(C)C=O)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=O.C(CC)=O.C1(=CC=CC=C1)C>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C=O)C | [CH2:23]([CH3:24])[CH:25]=[O:26].O=[CH:22][CH2:21][c:20]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[O:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]1)[C:27](=[O:28])[O:29][CH2:30]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:1... | CCC=O.COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=O)C(=O)OC2 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=C(C)C=O)C(=O)OC2 | null | null | null | C-C Coupling | OtherReaction | 154f038b7f5648ae5349abff8a924c982177f620bdfb6a2f53d7ca0fce37c68d | 3174a51604157c488f07402e36f994f716989b8fc10687ee243713b4cfbdb11a | O=C1OCc2cccc(OS(=O)(=O)c3ccccc3)c21 | O=[CH;D2;+0:1]-[C:2]-[c:3].[C;D1;H3:4]-[CH2;D2;+0:5]-[C:6]=[O;D1;H0:7]>>[C;D1;H3:4]-[C;H0;D3;+0:5](-[C:6]=[O;D1;H0:7])=[CH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | 16 | HOUR | A solution of 2-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)acetaldehyde (10.0 g) and 2-triphenylphosphoranylidine propionaldehyde (10.3 g) in toluene (150 mL) was heated under nitrogen atmosphere using an oil bath at 80° C. After allowing the reaction to proceed for 16 hours, the mix... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Aldehyde | null | null | c1ccccc1.c1ccc2c(c1)COC2 | HO- | null | null | 16 | CCC=O.COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=O)C(=O)OC2>>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=C(C)C=O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cf23d575e9194b7e8f2f8af78c19eb28 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=C(C)C=O)C(=O)OC2>>C=CC(O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C=O)C.C(=C)[Mg]Br>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C(C=C)O)C | [CH:3](=[O:4])[C:5]([CH3:6])=[CH:7][CH2:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([CH3:14])[c:15]2[c:16]([c:17]1[O:18][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]1)[C:29](=[O:30])[O:31][CH2:32]2>>[CH2:1]=[CH:2][CH:3]([OH:4])[C:5]([CH3:6])=[CH:7][CH2:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([CH3:14... | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=C(C)C=O)C(=O)OC2 | C=CC(O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 | null | null | O1CCCC1.C(C)(=O)OCC | Miscellaneous | OtherReaction | 7c95c9d475b3e4739c4b4bffdb557ccc0332365664dc5f751958e7bb4139acbc | 1cfdacde78204b273e664dc0eb50ffc4dc70522ea435514fcadd01e492b9b547 | O=C1OCc2cccc(OS(=O)(=O)c3ccccc3)c21 | [C:1]-[C:2]=[C:3](-[C;D1;H3:4])-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[C:1]-[C:2]=[C:3](-[C;D1;H3:4])-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7]=[C;D1;H2:8] | null | [] | null | null | 0.5 | HOUR | To a solution of 4-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)2-methylbut-2-enaldehyde (0.90 g) in tetrahydrofuran (40 mL) was added vinylmagnesium bromide (4.5 mL of a 1M solution in tetrahydrofuran). After stirring for 0.5 hours, the reaction was diluted with ethyl acetate and wash... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol.Vinyl | null | null | c1ccccc1.c1ccc2c(c1)COC2 | Other | O1CCCC1.C(C)(=O)OCC | null | 0.5 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC=C(C)C=O)C(=O)OC2>O1CCCC1.C(C)(=O)OCC>C=CC(O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-976750afea43480dbde7862b5dd1dd25 | C=CC(O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2>>C=CC(=O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C(C=C)O)C.[Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C(C=C)=O)C | [CH2:1]=[CH:2][CH:3]([OH:4])[C:5]([CH3:6])=[CH:7][CH2:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([CH3:14])[c:15]2[c:16]([c:17]1[O:18][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]1)[C:29](=[O:30])[O:31][CH2:32]2>>[CH2:1]=[CH:2][C:3](=[O:4])[C:5]([CH3:6])=[CH:7][CH2:8][c:9]1[c:10]([O:11][CH3:12])[... | C=CC(O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 | C=CC(=O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1OCc2cccc(OS(=O)(=O)c3ccccc3)c21 | [C:1]-[C:2]=[C:3](-[C;D1;H3:4])-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7]=[C;D1;H2:8]>>[C:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]=[C;D1;H2:8] | null | [] | null | null | 3 | HOUR | The oil product from Example ZC-1B, 6-(1,3-dihydro-6-methoxy -7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)-3-hydroxy -4-methylhexa-1,4-diene, was dissolved in methylene chloride (20 mL) and 4A molecular sieves (2 g) were added. With vigorous stirring, pyridinium dichromate (2 g) was added and the reaction a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2c(c1)COC2 | null | C(Cl)Cl | null | 3 | C=CC(O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2>C(Cl)Cl>C=CC(=O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9bfcdef938be481b93d518222f755bb0 | C=CC(=O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2>>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(=O)CC1)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C(C=C)=O)C.B(F)(F)F.CCOCC>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)=O)C | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]3)[c:20]1[CH2:21][CH:22]=[C:23]([CH3:24])[C:25](=[O:26])[CH:27]=[CH2:28])[C:29](=[O:30])[O:31][CH2:32]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]... | C=CC(=O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(=O)CC1)C(=O)OC2 | null | null | C(Cl)Cl.C(C)(=O)OCC | C-C Coupling | OtherReaction | 57106fdf64b8b2da8f414882c67b45f14b6a19fc78b6d73b28d8fd2222e3e4d1 | 2423fd262a32a267ed5d6ae9baff9668729a2c0a60281fcd676d6597312a598b | O=C1C=C(Cc2ccc3c(c2OS(=O)(=O)c2ccccc2)C(=O)OC3)CC1 | [C;D1;H3:1]-[C:2](=[CH;D2;+0:3]-[C:4]-[c:5])-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C;D1;H3:1]-[C:2]1=[C;H0;D3;+0:3](-[C:4]-[c:5])-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[C:6]-1=[O;D1;H0:7] | null | [] | null | null | 0.5 | HOUR | The solid product prepared in Example ZC-1C, 6-(1,3-dihydro -6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl) -4-methylhexa-1,4-dien-3-one was dissolved in methylene chloride (15 mL) and treated with boron trifluoride etherate (0.5 mL). After 0.5 hours, the reaction was diluted with ethyl acetate and ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Vinyl | Ketone | null | C1=CCCC1 | c1ccccc1.C1=CCCC1.c1ccc2c(c1)COC2 | null | C(Cl)Cl.C(C)(=O)OCC | null | 0.5 | C=CC(=O)C(C)=CCc1c(OC)c(C)c2c(c1OS(=O)(=O)c1ccc(C)cc1)C(=O)OC2>C(Cl)Cl.C(C)(=O)OCC>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(=O)CC1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a6c7fd2f95eb41c2a437b2e2f311beb5 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(=O)CC1)C(=O)OC2>>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(O)CC1)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)=O)C.O.O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+]>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)O)C | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]3)[c:20]1[CH2:21][C:22]1=[C:23]([CH3:24])[C:25](=[O:26])[CH2:27][CH2:28]1)[C:29](=[O:30])[O:31][CH2:32]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13... | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(=O)CC1)C(=O)OC2 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(O)CC1)C(=O)OC2 | null | null | O1CCCC1.CO.C(C)(=O)OCC | Reduction | Reduction of ketone to secondary alcohol | cdb715078de81de44f7378b33188a9fd6e2a8cc99d338ab2c91bd5935d725bcf | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C1OCc2ccc(CC3=CCCC3)c(OS(=O)(=O)c3ccccc3)c21 | [C:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[C:8]-1>>[C:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[C:8]-1 | 51.5 | [{"value": 51.5, "product": "COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-one (0.17 g) and cerium trichloride heptahydrate (0.172 g) in tetrahydrofuran/methanol (12 mL, 4/1) was treated with sodium borohydride (0.035 g). After 0.5 hours, the reaction was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=CCCC1 | C1=CCCC1 | c1ccccc1.C1=CCCC1.c1ccc2c(c1)COC2 | null | O1CCCC1.CO.C(C)(=O)OCC | null | 0.5 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(=O)CC1)C(=O)OC2>O1CCCC1.CO.C(C)(=O)OCC>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(O)CC1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-503f176e7c5e44bebb7bb239234d51f6 | C=COC1CCC(Cc2c(OC)c(C)c3c(c2OS(=O)(=O)c2ccc(C)cc2)C(=O)OC3)=C1C.COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(O)CC1)C(=O)OC2>>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(CC=O)CC1)C(=O)OC2 | Cl(=O)(=O)(=O)[O-].[Li+].COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)OC=C)C.COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)O)C>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)CC=O)C | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C([O:28][CH:27]=[CH2:26])CC1)C(=O)OC2.O[CH:25]1[C:23]([CH3:24])=[C:22]([CH2:21][c:20]2[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]3[c:7]([c:8]2[O:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]2)[C:31](=[O:32])[O:33][CH2:34]3)[CH2:30][CH2:29]1>>[CH3:... | C=COC1CCC(Cc2c(OC)c(C)c3c(c2OS(=O)(=O)c2ccc(C)cc2)C(=O)OC3)=C1C.COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(O)CC1)C(=O)OC2 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(CC=O)CC1)C(=O)OC2 | null | null | C([O-])(O)=O.[Na+].CCOCC.C(=C)OCC | Acylation | OtherReaction | 4ac1d4e9ef6c92f6ee3fdeb6d6ffad4520472e6d1762372c8ec75a279a39fec6 | d1039eb65b361cb7e491cf8dfd57a8623cae265c9dbfd4f1fbece64eeda0e199 | O=C1OCc2ccc(CC3=CCCC3)c(OS(=O)(=O)c3ccccc3)c21 | C-O-c1:c(-C):c2:c(:c(-O-S(=O)(=O)-c3:c:c:c(-C):c:c:3):c:1-C-C1=C(-C)-C(-[O;H0;D2;+0:1]-[CH;D2;+0:2]=[CH2;D1;+0:3])-C-C-1)-C(=O)-O-C-2.O-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7](-[C:8])=[C:9]-1-[C;D1;H3:10]>>[C:8]-[C:7]1=[C:9](-[C;D1;H3:10])-[CH;D3;+0:4](-[CH2;D2;+0:3]-[CH;D2;+0:2]=[O;H0;D1;+0:1])-[C:5]-[C:6]-1 | null | [] | null | null | 30 | HOUR | To a solution of 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ol (0.157 g) in ethyl vinyl ether (10 mL) was added mercuric acetate (0.052 g). After stirring for 30 hours at ambient temperature, the reaction was diluted with ether and passed quickly thr... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Ether.Ether.Secondary alcohol.Vinyl | Aldehyde | c1ccccc1.C1=CCCC1.c1ccc2c(c1)COC2.C1=CCCC1 | C1=CCCC1 | c1ccccc1.C1=CCCC1.c1ccc2c(c1)COC2 | TsOH.HO- | C([O-])(O)=O.[Na+].CCOCC.C(=C)OCC | null | 30 | C=COC1CCC(Cc2c(OC)c(C)c3c(c2OS(=O)(=O)c2ccc(C)cc2)C(=O)OC3)=C1C.COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(O)CC1)C(=O)OC2>C([O-])(O)=O.[Na+].CCOCC.C(=C)OCC>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=C(C)C(CC=O)CC1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa7994f29d584866a4cbf0cebfe7ff59 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC=O)CC1)C(=O)OC2>>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC(=O)O)CC1)C(=O)OC2 | Cl.C1(O)=CC(O)=CC=C1.COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=CC(CC1)(C)CC=O.Cl(=O)[O-].[Na+]>>COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=CC(CC1)(C)CC(=O)O | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]3[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]3)[c:20]1[CH2:21][C:22]1=[CH:23][C:24]([CH3:25])([CH2:26][CH:27]=[O:28])[CH2:30][CH2:31]1)[C:32](=[O:33])[O:34][CH2:35]2>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][S:10](=[O:11... | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC=O)CC1)C(=O)OC2 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC(=O)O)CC1)C(=O)OC2 | null | null | O1CCOCC1.C(C)(=O)OCC | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | O=C1OCc2ccc(CC3=CCCC3)c(OS(=O)(=O)c3ccccc3)c21 | [C:1]=[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[O;D1;H0:6]>>[C:1]=[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | 2 | MINUTE | The 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-1-methylcyclopent-2-en-1-ylacetaldehyde was dissolved in dioxane (8 mL) and pH 5 buffer (3 mL) and treated with resorcinol (0.10 g). To this mixture was then added sodium chlorite (0.080 g). After 2 minutes, the reaction was dil... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1ccccc1.C1=CCCC1.c1ccc2c(c1)COC2 | Other | O1CCOCC1.C(C)(=O)OCC | null | 0.033333 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC=O)CC1)C(=O)OC2>O1CCOCC1.C(C)(=O)OCC>COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC(=O)O)CC1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d044b48c5b3d413691e992c6ba016b16 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC(=O)O)CC1)C(=O)OC2>>COc1c(C)c2c(c(O)c1CC1=C(C)C(CC(=O)O)CC1)C(=O)OC2 | COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=CC(CC1)(C)CC(=O)O.O.[OH-].[Li+].CO.Cl>>OC1=C2C(OCC2=C(C(=C1CC1=C(C(CC1)CC(=O)O)C)OC)C)=O | Cc1ccc(S(=O)(=O)[O:9][c:8]2[c:7]3[c:6]([c:4]([CH3:5])[c:3]([O:2][CH3:1])[c:10]2[CH2:11][C:12]2=[CH:13][C:15]([CH3:14])([CH2:16][C:17](=[O:18])[OH:19])[CH2:20][CH2:21]2)[CH2:25][O:24][C:22]3=[O:23])cc1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11][C:12]1=[C:13]([CH3:14])[CH:15]([CH2:16][C:17]... | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC(=O)O)CC1)C(=O)OC2 | COc1c(C)c2c(c(O)c1CC1=C(C)C(CC(=O)O)CC1)C(=O)OC2 | null | null | O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 3b7ec937074c4678fd2476ef5eb15cf0d8cef638bcba24b7cfc4bedc8fe57bc6 | f42bc74ea3e4acde8f757a6addaeeffa0b8900d54d39319d008e787b16303792 | O=C1OCc2ccc(CC3=CCCC3)cc21 | C-c1:c:c:c(-S(=O)(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]-[C:4]-[C:5]2=[CH;D2;+0:6]-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[C:13]-[C:14]-2):[c:15]-[C:16](=[O;D1;H0:17])-[#8:18]):c:c:1>>[#8:18]-[C:16](=[O;D1;H0:17])-[c:15]:[c:2](-[OH;D1;+0:1]):[c:3]-[C:4]-[C:5]1=[C;H0;D3;+0:6](-[CH3;D1;+0:8])-... | null | [] | null | null | 4 | HOUR | The 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy -5-isobenzofuranylmethyl)-1-methylcyclopent-2-en-1-ylacetic acid obtained in Example ZC-1G was dissolved in a mixture of methanol (8 mL) and water (2 mL) and treated with lithium hydroxide monohydrate (0.15 g). After 4 hours, the reaction was diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate | Aromatic alcohol | c1ccccc1.C1=CCCC1 | C1=CCCC1 | C1=CCCC1.c1ccc2c(c1)COC2 | TsOH.HO- | O.C(C)(=O)OCC | null | 4 | COc1c(C)c2c(c(OS(=O)(=O)c3ccc(C)cc3)c1CC1=CC(C)(CC(=O)O)CC1)C(=O)OC2>O.C(C)(=O)OCC>COc1c(C)c2c(c(O)c1CC1=C(C)C(CC(=O)O)CC1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-07739d7edf5d440498c0eb8a27b6ce82 | CCOC(=O)C1CC/C(=C\Cc2c(O)c3c(c(C)c2OC)COC3=O)C1>>COc1c(C)c2c(c(O)c1C/C=C1\CCC(C(=O)O)C1)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C\C=C/1\CC(CC1)C(=O)OCC)OC)C)=O>>OC1=C2C(OCC2=C(C(=C1C\C=C/1\CC(CC1)C(=O)O)OC)C)=O | CC[O:19][C:17]([CH:16]1[CH2:15][CH2:14]/[C:13](=[CH:12]\[CH2:11][c:10]2[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]3[c:7]([c:8]2[OH:9])[C:21](=[O:22])[O:23][CH2:24]3)[CH2:20]1)=[O:18]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11]/[CH:12]=[C:13]1\[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[OH:19])[CH2:... | CCOC(=O)C1CC/C(=C\Cc2c(O)c3c(c(C)c2OC)COC3=O)C1 | COc1c(C)c2c(c(O)c1C/C=C1\CCC(C(=O)O)C1)C(=O)OC2 | null | null | CCCCCC.ClCCl | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccc(CC=C3CCCC3)cc21 | 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] | null | [] | null | null | null | null | By following the procedure of Example ZA-6A and substituting methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoate with ethyl (E)-3-[2-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopentane -1-carboxylate (prepared e.g, as described w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1.c1ccc2c(c1)COC2 | Other | CCCCCC.ClCCl | null | null | CCOC(=O)C1CC/C(=C\Cc2c(O)c3c(c(C)c2OC)COC3=O)C1>CCCCCC.ClCCl>COc1c(C)c2c(c(O)c1C/C=C1\CCC(C(=O)O)C1)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7820518b8590443d8b86b8ccf4ea84e0 | C=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.CC(=O)OC(C)=O>>C=CCc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | C(C)(=O)OC(C)=O.C(C=C)C=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C>>C(C)(=O)OC1=C2C(OCC2=C(C(=C1CC=C)OC)C)=O | CC(C)(C)[Si](C)(C)[O:13][c:12]1[c:4]([CH2:3][CH:2]=[CH2:1])[c:5]([O:6][CH3:7])[c:8]([CH3:9])[c:10]2[c:11]1[C:17](=[O:18])[O:19][CH2:20]2.CC(=O)O[C:14]([CH3:15])=[O:16]>>[CH2:1]=[CH:2][CH2:3][c:4]1[c:5]([O:6][CH3:7])[c:8]([CH3:9])[c:10]2[c:11]([c:12]1[O:13][C:14]([CH3:15])=[O:16])[C:17](=[O:18])[O:19][CH2:20]2 | C=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.CC(=O)OC(C)=O | C=CCc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | null | null | C(C)(=O)O | Acylation | OtherReaction | dc2e4916eb1e0336df7600ab21ace635942c529e40899dfc51f11e1099dafec6 | cd167da0128b84942308a2361251a58b9a15c9502e99a9a75e3e1ddf830ff991 | O=C1OCc2ccccc21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#8:7].C-C(=O)-O-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;D1;H0:10]>>[#8:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[O;H0;D2;+0:1]-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;D1;H0:10]):[c:3] | null | [] | null | null | null | null | A solution of 5-allyl-4-tert-butyldimethylsilyloxy-1,3-dihydro -6-methoxy-7-methyl-3-oxoisobenzofuran [(J. W. Patterson and G. Huang, Chemical Communications, 1579 (1991)] (7.5 g) in acetic acid (95 ml) and acetic anhydride (95 ml) was refluxed for 18 hours, then cooled and poured into ice water. The solution was extra... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.TMS ether protective group | Ester | null | null | c1ccc2c(c1)COC2 | HO- | C(C)(=O)O | null | null | C=CCc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2.CC(=O)OC(C)=O>C(C)(=O)O>C=CCc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9b1df400bb1d44a4868aff1a360a7ffa | C=CCc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2.COC(=O)c1cccc(C)c1Br>>COC(=O)c1cccc(C)c1/C=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | C(C)(=O)OC1=C2C(OCC2=C(C(=C1CC=C)OC)C)=O.BrC1=C(C(=O)OC)C=CC=C1C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.Cl>>C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C/C1=C(C(=O)OC)C=CC=C1C)OC)C)=O | [CH2:12]=[CH:13][CH2:14][c:15]1[c:16]([O:17][CH3:18])[c:19]([CH3:20])[c:21]2[c:22]([c:23]1[O:24][C:25]([CH3:26])=[O:27])[C:28](=[O:29])[O:30][CH2:31]2.Br[c:11]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]1[CH3:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]1/[CH:12]=[CH:13]/[CH2:1... | C=CCc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2.COC(=O)c1cccc(C)c1Br | COC(=O)c1cccc(C)c1/C=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | null | C([O-])([O-])=O.[Ag+2].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C=O)C | C-C Coupling | OtherReaction | 2d4a44695e29e4a9ab430c3b66736ad86dd99247e7216f16f3ca137abca78747 | df8442c9f2045421fb18548edb9c6acaeb9710f63e741d9f72e0000ca35c948a | O=C1OCc2ccc(C/C=C/c3ccccc3)cc21 | Br-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[c:7]):[c:8](-[C;D1;H3:9]):[c:10].[C:11]-[C:12]=[CH2;D1;+0:13]>>[C:11]/[C:12]=[CH;D2;+0:13]/[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[c:7]):[c:8](-[C;D1;H3:9]):[c:10] | null | [] | 100 | CELSIUS | 6 | HOUR | 4-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran (0.6 g), methyl 2-bromo-3-methylbenzoate (0.92 g), silver carbonate (1.3 g), palladium acetate (0.1 g), triphenylphosphine (0.14 g) and dimethylformamide (70 ml) were heated with stirring at 100° C. for 6 hours, then stirred at ambient temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)COC2 | HBr | C([O-])([O-])=O.[Ag+2].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C | 100 | 6 | C=CCc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2.COC(=O)c1cccc(C)c1Br>C([O-])([O-])=O.[Ag+2].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C>COC(=O)c1cccc(C)c1/C=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-47c6f01829024b97bbd90d3a8cd2c7d7 | COC(=O)c1cccc(C)c1/C=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2>>COc1c(C)c2c(c(OC(C)=O)c1C/C=C/c1c(C)cccc1C(=O)O)C(=O)OC2 | C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C/C1=C(C(=O)OC)C=CC=C1C)OC)C)=O.[OH-].[Li+].Cl>>C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C/C1=C(C(=O)O)C=CC=C1C)OC)C)=O | C[O:26][C:24]([c:23]1[c:17](/[CH:16]=[CH:15]/[CH2:14][c:13]2[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]3[c:7]([c:8]2[O:9][C:10]([CH3:11])=[O:12])[C:27](=[O:28])[O:29][CH2:30]3)[c:18]([CH3:19])[cH:20][cH:21][cH:22]1)=[O:25]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][C:10]([CH3:11])=[O:12])[c:13]1[CH2:14]/[CH:15... | COC(=O)c1cccc(C)c1/C=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2 | COc1c(C)c2c(c(OC(C)=O)c1C/C=C/c1c(C)cccc1C(=O)O)C(=O)OC2 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccc(C/C=C/c3ccccc3)cc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A solution of methyl (E)-2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate (0.1 g) and lithium hydroxide (0.06 g) in methanol (1 ml) and water (1 ml) was heated at 70° C. for 48 hours. The solution was cooled and poured into water, then acidified with 2N hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)COC2 | Other | O.CO | null | null | COC(=O)c1cccc(C)c1/C=C/Cc1c(OC)c(C)c2c(c1OC(C)=O)C(=O)OC2>O.CO>COc1c(C)c2c(c(OC(C)=O)c1C/C=C/c1c(C)cccc1C(=O)O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b4a749ba1a50456f8151b855f22ae779 | CC(C)(C)C(=O)O.COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)/C(C)=C/CC(C)C(C)(O[SiH3])C(C)(C)C)C(=O)OC2>>CCOC(=O)CC(CCCO[Si](C)(C)C(C)(C)C)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(/C(=C/CC(C(C(C)(C)C)(O[SiH3])C)C)/C)O)OC)C)=O.C(C(C)(C)C)(=O)O>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO[Si](C)(C)C(C)(C)C)\C)OC)C)=O | [CH3:1][C:2]([C:4]([OH:3])=[O:5])([CH3:13])[CH3:14].C[CH:9]([C:7](O[SiH3:12])([CH3:6])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:8]/[CH:21]=[C:19](/[CH:10]([OH:11])[CH2:22][c:23]1[c:24]([O:25][CH3:26])[c:27]([CH3:28])[c:29]2[c:30]([c:31]1[O:32][Si:33]([CH3:34])([CH3:35])[C:36]([CH3:37])([CH3:38])[CH3:39])[C:40](=[O:41])[O... | CC(C)(C)C(=O)O.COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)/C(C)=C/CC(C)C(C)(O[SiH3])C(C)(C)C)C(=O)OC2 | CCOC(=O)CC(CCCO[Si](C)(C)C(C)(C)C)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | null | CCOCC.C(C)(OCC)(OCC)OCC | C-C Coupling | OtherReaction | a1a7af0c08b7f601e7365d00f615cb09e77e1fb8a8adb2a8aed8c2fb085907d6 | d768a9cd2aa0fcd146aba6171d08b2a3f65cd24f010103bca90ec50d75a81782 | O=C1OCc2ccccc21 | C-[CH;D3;+0:1](-[CH2;D2;+0:2]/[CH;D2;+0:3]=[C;H0;D3;+0:4](\[C;D1;H3:5])-[CH;D3;+0:6](-[OH;D1;+0:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C;H0;D4;+0:12](-[CH3;D1;+0:13])(-O-[SiH3;D1;+0:14])-[C;H0;D4;+0:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18].[C;D1;H3:19]-[C;H0;D4;+0:20](-[CH3;D1;+0:21])(-[CH3;D1;+0:22])-[C;H0;D3... | 276.5 | [{"value": 276.5, "product": "[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO[Si](C)(C)C(C)(C)C)\\C)OC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | (E)-7-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-1-tert-butyldimethyl-silyloxy-6-hydroxy -5-methylhept-4-ene (4.74 g) was dissolved in triethyl orthoacetate (76 ml) and pivalic acid (171 mg) was added. The solution was placed in an oil bath preheated to 130° C., and stirred f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester.TMS ether protective group | null | null | c1ccc2c(c1)COC2 | HO- | CCOCC.C(C)(OCC)(OCC)OCC | null | 0.5 | CC(C)(C)C(=O)O.COc1c(C)c2c(c(O[Si](C)(C)C(C)(C)C)c1CC(O)/C(C)=C/CC(C)C(C)(O[SiH3])C(C)(C)C)C(=O)OC2>CCOCC.C(C)(OCC)(OCC)OCC>CCOC(=O)CC(CCCO[Si](C)(C)C(C)(C)C)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-836ced56c8c24fdfb72bfddef7a5f7f9 | CCOC(=O)CC(CCCO[Si](C)(C)C(C)(C)C)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>CCOC(=O)CC(CCCO)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO[Si](C)(C)C(C)(C)C)\C)OC)C)=O>>[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO)\C)OC)C)=O | CC(C)(C)[Si](C)(C)[O:11][CH2:10][CH2:9][CH2:8][CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])/[C:12]([CH3:13])=[CH:14]/[CH2:15][c:16]1[c:17]([O:18][CH3:19])[c:20]([CH3:21])[c:22]2[c:23]([c:24]1[O:25][Si:26]([CH3:27])([CH3:28])[C:29]([CH3:30])([CH3:31])[CH3:32])[C:33](=[O:34])[O:35][CH2:36]2>>[CH3:1][CH2:2][O:3][C:4](=[... | CCOC(=O)CC(CCCO[Si](C)(C)C(C)(C)C)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | CCOC(=O)CC(CCCO)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | null | null | C(C)#N | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=C1OCc2ccccc21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 87.7 | [{"value": 87.7, "product": "[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO)\\C)OC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxo-isobenzofuran-5-yl)-3-(3-tert-butyldimethylsilyloxypropyl) -4-methylhex-4-enoate (2.92 g) was dissolved in acetonitrile (50 ml). To this was added a solution of 40% aqueous HF (5 ml) in acetonitrile (45 ml), and the reaction mixture stirred... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccc2c(c1)COC2 | Other | C(C)#N | null | 0.166667 | CCOC(=O)CC(CCCO[Si](C)(C)C(C)(C)C)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>C(C)#N>CCOC(=O)CC(CCCO)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0320830997a041e49aaec6fb21a36af9 | CCOC(=O)CC(CCCBr)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>>CCOC(=O)CC(CCCBr)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | [Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCBr)\C)OC)C)=O.O.O.O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCBr)\C)OC)C)=O | CC(C)(C)[Si](C)(C)[O:18][c:17]1[c:16]([CH2:15]/[CH:14]=[C:12](/[CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8][CH2:9][CH2:10][Br:11])[CH3:13])[c:23]([O:24][CH3:25])[c:21]([CH3:22])[c:20]2[c:19]1[C:28](=[O:29])[O:27][CH2:26]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH2:8][CH2:9][CH2:10][Br:11])/[C:12]([CH... | CCOC(=O)CC(CCCBr)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2 | CCOC(=O)CC(CCCBr)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | null | null | CCOCC.C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | O=C1OCc2ccccc21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#8:7]>>[#8:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 62.2 | [{"value": 62.2, "product": "OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCBr)\\C)OC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | A solution of of ethyl (E) 6-(4-tert-butyldimethylsilyloxy -1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -3-(3-bromopropyl)-4-methylhex-4-enoate (1.62 g) was dissolved in THF (25 ml), cooled to 0° C., and a solution of tetrabutylammonium fluoride trihydrate (919 mg) in THF (5 ml) was added. The reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccc2c(c1)COC2 | Other | CCOCC.C1CCOC1 | 0 | 0.25 | CCOC(=O)CC(CCCBr)/C(C)=C/Cc1c(OC)c(C)c2c(c1O[Si](C)(C)C(C)(C)C)C(=O)OC2>CCOCC.C1CCOC1>CCOC(=O)CC(CCCBr)/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8a7d68a9fc10428b81c893f585c53f4a | CCOC(=O)C1CCCC1/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>>COc1c(C)c2c(c(O)c1C/C=C(\C)C1CCCC1C(=O)O)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(\C)/C1C(CCC1)C(=O)OCC)OC)C)=O>>OC1=C2C(OCC2=C(C(=C1C/C=C(\C)/C1C(CCC1)C(=O)O)OC)C)=O | CC[O:22][C:20]([CH:19]1[CH:15](/[C:13](=[CH:12]/[CH2:11][c:10]2[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]3[c:7]([c:8]2[OH:9])[C:23](=[O:24])[O:25][CH2:26]3)[CH3:14])[CH2:16][CH2:17][CH2:18]1)=[O:21]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH:15]1[CH2:16][CH2:17][C... | CCOC(=O)C1CCCC1/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O | COc1c(C)c2c(c(O)c1C/C=C(\C)C1CCCC1C(=O)O)C(=O)OC2 | null | null | CCCCCC.C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1OCc2ccc(CC=CC3CCCC3)cc21 | 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] | null | [] | null | null | null | null | By following the procedure of Example ZA-6A and substituting methyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran -5-yl)-2,4-dimethyl-4-hexenoate with ethyl (E)-2-[-3-(4-hydroxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-methylpropenyl ]-cyclopentane-carboxylate and compounds of Form... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1.c1ccc2c(c1)COC2 | Other | CCCCCC.C(C)(=O)OCC | null | null | CCOC(=O)C1CCCC1/C(C)=C/Cc1c(O)c2c(c(C)c1OC)COC2=O>CCCCCC.C(C)(=O)OCC>COc1c(C)c2c(c(O)c1C/C=C(\C)C1CCCC1C(=O)O)C(=O)OC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ab73c212c79c45b8805584012da837d6 | CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\C(=O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1>>CC1=C[C@H]2O[C@@H]3CC[C@@](C)(C3C)[C@@]2(C)CC1 | [Se](=O)=O.C[C@@H]1CCOC(=O)/C=C/C=C\C(=O)O[C@@H]2C[C@@H]3[C@]4([C@]2([C@]5(CCC(=C[C@H]5O3)C)COC(=O)[C@H]1O)C)CO4>>CC1[C@H]2CC[C@@]1([C@]3(CCC(=C[C@H]3O2)C)C)C | C[C@@H]1CCOC(=O)/C=C/C=C\C(=O)O[C@@H:8]2[CH2:7][C@H:6]3[O:5][C@@H:4]4[CH:3]=[C:2]([CH3:1])[CH2:16][CH2:15][C@@:13]4([C@:9]2([CH3:10])[C@@:11]32O[CH2:12]2)[CH2:14]OC(=O)[C@H]1O>>[CH3:1][C:2]1=[CH:3][C@H:4]2[O:5][C@@H:6]3[CH2:7][CH2:8][C@@:9]([CH3:10])([CH:11]3[CH3:12])[C@@:13]2([CH3:14])[CH2:15][CH2:16]1 | CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\C(=O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1 | CC1=C[C@H]2O[C@@H]3CC[C@@](C)(C3C)[C@@]2(C)CC1 | null | null | null | Reduction | OtherReaction | eab71b612ede83a39b8bdbe09aced4e88043cd674701b49a41ec319f03026e88 | 0d48a27d606bb0a7b9f1bb881aa368ce08db06636d6bc6626511bfbcfa12a5d7 | C1=C[C@H]2O[C@@H]3CCC(C3)C2CC1 | null | null | [] | null | null | null | null | The trichothecene therapeutic agent 16-oxo verrucarin A is prepared by selenium dioxide oxidation of verrucarin A. The MAb hydrazide is then reacted with 16-oxo verrucarin A at 4° C. overnight with agitation, thereby yielding a unique Schiff base-linked targeting protein having the following structure: ##STR19##
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Secondary alcohol.Conjugated diene | null | C1=C[C@H]2O[C@@H]3C[C@H]4OC/C=C\C=C\COCCCCCOC[C@@]2(CC1)[C@@H]4[C@]31CO1 | C1=C[C@H]2O[C@@H]3CC[C@@H](C3)[C@H]2CC1 | C1=C[C@H]2O[C@@H]3CC[C@@H](C3)[C@H]2CC1 | HO- | null | null | null | CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\C(=O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1>>CC1=C[C@H]2O[C@@H]3CC[C@@](C)(C3C)[C@@]2(C)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f301d0b9494940d59d0901c5a8aebf22 | C#CCCC.O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1I>>CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | CO.IC=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O.C#CCCC.C([O-])(O)=O>>C(#CCCC)C=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O | [CH3:1][CH2:2][CH2:3][C:4]#[CH:5].I[c:6]1[cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21] | C#CCCC.O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1I | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | 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.[Cu]I | C(Cl)Cl | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]-[#8:5]):[c:6]:[#7;a:7]:[c:8]:1=[O;D1;H0:9].[C:10]-[C:11]#[CH;D1;+0:12]>>[#8:5]-[C:4]-[#7;a:3]1:[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:1](-[C;H0;D2;+0:12]#[C:11]-[C:10]):[c:2]:1 | 81.9 | [{"value": 81.9, "product": "C(#CCCC)C=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 26 | HOUR | This compound was prepared by the same procedure that Hobbs, F. W. J., J Org Chem (1989) 54: 3420-3422, used for the preparation of other alkynyl substituted nucleosides. A mixture of 30.0 g (84.7 mmol) of 5-iodo-2'deoxyuridine (purchased from Sigma), 23.6 mL of 1-pentyne (Aldrich), 9.79 g of tetrakis (triphenylphosphi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CCOC1 | HI | [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.[Cu]I.C(Cl)Cl | null | 26 | C#CCCC.O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1I>[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.[Cu]I.C(Cl)Cl>CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4fc6b35319144df28c3a7ce2cc497b35 | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>>CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](COC(c3ccccc3)(c3ccc(OC)cc3)c3ccc(OC)cc3)O2)c(=O)[nH]c1=O | C(#CCCC)C=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O.COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1>>COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(=C2)C#CCCC)O)C=C1 | [CH3:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:39]2)[c:40](=[O:41])[nH:42][c:43]1=[O:44].Cl[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)([c:23]1[cH:24][cH:25][c:26]([O:27][CH3:28])[cH:29][cH:30]1)[c:31]1[cH:32][cH:33][c:34]([O:35][CH3:36])[cH:37][cH... | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1 | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](COC(c3ccccc3)(c3ccc(OC)cc3)c3ccc(OC)cc3)O2)c(=O)[nH]c1=O | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb955127af596450632db904a0236d35e158107f202af7adbe96e225ff5ada1f | 5adfb0e9c2ca3c5afac2c4b206fb6fda83b92f44074f2a75e26f913c192bc169 | O=c1ccn([C@H]2CC[C@@H](COC(c3ccccc3)(c3ccccc3)c3ccccc3)O2)c(=O)[nH]1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12]-[C:13]-[OH;D1;+0:14]>>[#8:11]-[C:12]-[C:13]-[O;H0;D2;+0:14]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 54.5 | [{"value": 52.9, "product": "COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(=C2)C#CCCC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(=C2)C#CCCC)O)C=C1", "details":... | null | null | 17 | HOUR | To 20.4 g (69.3 mmol) of 5-(1-pentynyl)-2'-deoxyuridine in 300 mL of dry pyridine was added 22.8 g of 4,4'-dimethoxytrityl chloride. The reaction was stirred for 17 h at room temperature and then concentrated. The residue was taken up in CH2Cl2 and washed twice with 0.5% aqueous NaHCO3, dried (Na2SO4), filtered, and co... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary alcohol | Ether | null | null | c1cncnc1.C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 17 | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>N1=CC=CC=C1>CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](COC(c3ccccc3)(c3ccc(OC)cc3)c3ccc(OC)cc3)O2)c(=O)[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-775c308cf3824ac2aaae6e5316af307d | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>CCCCCc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | C(#CCCC)C=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O>>C(CCCC)C=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O | [CH3:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21] | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | CCCCCc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | null | [Pd] | CO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | [#8:1]-[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6](=[O;D1;H0:7]):[c:8](-[C;H0;D2;+0:9]#[C;H0;D2;+0:10]-[C:11]-[C:12]):[c:13]:1>>[#8:1]-[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6](=[O;D1;H0:7]):[c:8](-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[C:12]):[c:13]:1 | null | [] | null | null | 14 | HOUR | To a solution of 1.03 g (3.50 mmol) of 5-(1-pentynyl)-2'-deoxyuridine in 25 mL of MeOH was added a catalytic amount of 10% Pd on charcoal. The mixture was hydrogenated under 300 psi of H2 for 14 h at room temperature. The mixture was filtered through Celite and concentrated, affording a quantitative yield of product.
C... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1cncnc1.C1CCOC1 | null | [Pd].CO | null | 14 | CCCC#Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>[Pd].CO>CCCCCc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1599ec65fdd54d67a7b447137a9c1a30 | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@]1(O)C(C)=O>>CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@H]1O | Br[C@H]1[C@@H](O[C@@H]([C@]1(O)C(C)=O)COC(C)=O)N1C(=O)NC(=O)C(=C1)C.O.NN.Cl>>Br[C@H]1[C@@H](O[C@@H]([C@H]1O)COC(C)=O)N1C(=O)NC(=O)C(=C1)C | CC(=O)[C@@:20]1([OH:21])[C@@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[O:7][C@@H:8]([n:9]2[cH:10][c:11]([CH3:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[C@@H:18]1[Br:19]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][c:11]([CH3:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[C@H:18]([Br:19])[C@@H:20]1[OH:21] | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@]1(O)C(C)=O | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@H]1O | null | null | O.C(C)#N | Reduction | OtherReaction | 43d88ce45446e857bff66cf064de0c45cea59f153344a8de8b37df2ca8b00fba | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-C(=O)-[C@;H0;D4;+0:1]1(-[O;D1;H1:2])-[C:3](-[Br;D1;H0:4])-[C:5]-[#8:6]-[C:7]-1-[C:8]>>[Br;D1;H0:4]-[C:3]1-[C:5]-[#8:6]-[C:7](-[C:8])-[C@H;D3;+0:1]-1-[O;D1;H1:2] | 92.9 | [{"value": 76.0, "product": "Br[C@H]1[C@@H](O[C@@H]([C@H]1O)COC(C)=O)N1C(=O)NC(=O)C(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "Br[C@H]1[C@@H](O[C@@H]([C@H]1O)COC(C)=O)N1C(=O)NC(=O)C(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 400 ml of acetonitrile and 2.16 g (3 equivalents) of water were added to 16.2 g (40.0 mmol) of 2'-deoxy-2'-bromo-3',5'-O-diacetyl-5-methyluridine, and the mixture was stirred. The resulting solution was cooled to 0° C., 6.01 g (3 equivalents) of hydrazine monohydrate were added thereto, and the mixture was reacted for ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCOC1 | C1CCOC1 | C1CCOC1.c1cncnc1 | HO- | O.C(C)#N | 0 | null | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@]1(O)C(C)=O>O.C(C)#N>CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@H]1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3257e360c2f74fb392e93d05e85ea09c | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@H]1O>>CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O | Br[C@H]1[C@@H](O[C@@H]([C@H]1O)COC(C)=O)N1C(=O)NC(=O)C(=C1)C.C(C)(=O)[O-].[Na+].[H][H]>>C(C)(=O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O | Br[C@H:18]1[C@H:8]([n:9]2[cH:10][c:11]([CH3:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[O:7][C@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[C@H:19]1[OH:20]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][c:11]([CH3:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[CH2:18][C@@H:19]1[OH:20] | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@H]1O | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O | null | S(=O)(=O)([O-])[O-].[Ba+2].[Pd+2].S(=O)(=O)([O-])[O-] | CO | Functional Group Interconversion | Dehalogenation | 2c0570e07732844d84f39e96c7630be6331c1effa6291ee67002cb43b6c323f3 | 6e8d13230370538f865fe4c85906dd6cad07c6cb5b152c1d96823b885b960ee6 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | Br-[C@@H;D3;+0:1]1-[C:2](-[O;D1;H1:3])-[C:4]-[#8:5]-[C:6]-1-[#7;a:7]>>[#7;a:7]-[C:6]1-[#8:5]-[C:4]-[C:2](-[O;D1;H1:3])-[CH2;D2;+0:1]-1 | 38.1 | [{"value": 38.1, "product": "C(C)(=O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.1, "product": "C(C)(=O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 12.47 g (28.1 mmol) of 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine were dissolved in 240 ml of methanol, and 6.91 g (3 equivalents) of sodium acetate were added thereto. To the reaction mixture, were added 1.25 g of 5% palladium-barium sulfate catalyst (0.1 equivalent). Then, the reaction system was filled with hydro... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | C1CCOC1 | C1CCOC1 | C1CCOC1.c1cncnc1 | Br- | S(=O)(=O)([O-])[O-].[Ba+2].[Pd+2].S(=O)(=O)([O-])[O-].CO | null | null | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)[C@H](Br)[C@@H]1O>S(=O)(=O)([O-])[O-].[Ba+2].[Pd+2].S(=O)(=O)([O-])[O-].CO>CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-72f2399edc644c439d5d6ecafa1270b7 | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O.CS(=O)(=O)Cl>>CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1OS(C)(=O)=O | C(C)(=O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O.CS(=O)(=O)Cl.CS(=O)(=O)Cl>>C(C)(=O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)OS(=O)(=O)C | [CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][c:11]([CH3:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[CH2:18][C@@H:19]1[OH:20].Cl[S:21]([CH3:22])(=[O:23])=[O:24]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][c:11]([CH3:12])[c:13](=[O:14])[nH:15][c:16]2=[O:17])[CH2:18][C@@H:19]1... | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O.CS(=O)(=O)Cl | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1OS(C)(=O)=O | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#8:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | null | [] | 0 | CELSIUS | null | null | The 5'-O-acetylthymidine obtained in Example 7 was dissolved in 100 ml of pyridine and cooled to 0° C. Then, 11.57 g (2 equivalents) of methanesulfonyl chloride were added thereto. After these were reacted at 0° C. for 1.5 hours, 5.79 g (one equivalent) of methanesulfonyl chloride were added thereto and reacted at 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CCOC1.c1cncnc1 | HCl | N1=CC=CC=C1 | 0 | null | CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O.CS(=O)(=O)Cl>N1=CC=CC=C1>CC(=O)OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1OS(C)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ba6618a5350d412685ae28c1c46959dc | N#CN=C(Oc1ccccc1)Oc1ccccc1.Nc1cncnc1>>N#CN=C(Nc1cncnc1)Oc1ccccc1 | C1=CC=C(C=C1)OC(=NC#N)OC2=CC=CC=C2.NC=1C=NC=NC1>>C(#N)N=C(NC=1C=NC=NC1)OC1=CC=CC=C1 | c1ccc(O[C:4](=[N:3][C:2]#[N:1])[O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)cc1.[NH2:5][c:6]1[cH:7][n:8][cH:9][n:10][cH:11]1>>[N:1]#[C:2][N:3]=[C:4]([NH:5][c:6]1[cH:7][n:8][cH:9][n:10][cH:11]1)[O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | N#CN=C(Oc1ccccc1)Oc1ccccc1.Nc1cncnc1 | N#CN=C(Nc1cncnc1)Oc1ccccc1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | ee096f5ab320ed58f4369523918a4c51313bdefd69ab4de3888cdce5737c1bea | c04464d7d733f4672f5db3386f93d469810e8d1c6e2a36f603b54b46a74b4d93 | N=C(Nc1cncnc1)Oc1ccccc1 | [N;D1;H0:1]#[C:2]-[#7:3]=[C;H0;D3;+0:4](-O-c1:c:c:c:c:c:1)-[#8:5]-[c:6].[NH2;D1;+0:7]-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1>>[N;D1;H0:1]#[C:2]-[#7:3]=[C;H0;D3;+0:4](-[#8:5]-[c:6])-[NH;D2;+0:7]-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1 | 53.9 | [{"value": 53.9, "product": "C(#N)N=C(NC=1C=NC=NC1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | A stirred mixture of diphenyl cyanocarbonimidate (1.05 g, 0.00442 mol), 5-amino-pyrimidine (0.42 g, 0.00442 mol) and Et2O (15 mL) was kept at ambient temperature for 4 days and at reflux for one day. There was little reaction. The solvent was evaporated and the residue was mixed with DME and warmed at 50°-55° for 2 day... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | Ether.Secondary amine | c1ccccc1 | null | c1cncnc1.c1ccccc1 | HO- | CCOCC | null | 96 | N#CN=C(Oc1ccccc1)Oc1ccccc1.Nc1cncnc1>CCOCC>N#CN=C(Nc1cncnc1)Oc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e078ab19abb14e4ab8ca11ba7e1f1bc5 | C[C@@H](N)c1ccccc1.N#CN=C(Nc1cncnc1)Oc1ccccc1>>C[C@@H](NC(=NC#N)Nc1cncnc1)c1ccccc1 | C(#N)N=C(NC=1C=NC=NC1)OC1=CC=CC=C1.C[C@H](C1=CC=CC=C1)N>>C(#N)N=C(NC=1C=NC=NC1)N[C@H](C)C1=CC=CC=C1 | [CH3:1][C@@H:2]([NH2:3])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.c1ccc(O[C:4](=[N:5][C:6]#[N:7])[NH:8][c:9]2[cH:10][n:11][cH:12][n:13][cH:14]2)cc1>>[CH3:1][C@@H:2]([NH:3][C:4](=[N:5][C:6]#[N:7])[NH:8][c:9]1[cH:10][n:11][cH:12][n:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[C@@H](N)c1ccccc1.N#CN=C(Nc1cncnc1)Oc1ccccc1 | C[C@@H](NC(=NC#N)Nc1cncnc1)c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 114d8f7243f9e520c2011150952e9826f1217db119c95c007b250beda4b0554b | 953ca34981f329c845365ec5b25a3d27fa72aebd3e467f4e6ef8becba38a9d76 | N=C(NCc1ccccc1)Nc1cncnc1 | [#7;a:1]:[c:2]:[c:3](-[#7:4]-[C;H0;D3;+0:5](-O-c1:c:c:c:c:c:1)=[#7:6]-[C:7]#[N;D1;H0:8]):[c:9]:[#7;a:10].[C;D1;H3:11]-[C:12](-[NH2;D1;+0:13])-[c:14]>>[#7;a:1]:[c:2]:[c:3](-[#7:4]-[C;H0;D3;+0:5](=[#7:6]-[C:7]#[N;D1;H0:8])-[NH;D2;+0:13]-[C:12](-[C;D1;H3:11])-[c:14]):[c:9]:[#7;a:10] | null | [] | null | null | 18 | HOUR | A stirred mixture of N'-cyano-N-(5-pyrimidyl)-O-phenylisourea (0.5 g, 0.00209 mol), (R)-α-methylbenzylamine (1.0 mL) and DMF (4 mL) was kept, under nitrogen, at ambient temperature for 18 hours and concentrated in vacuo. The residue was allowed to crystallize from EtOAc-tert-butyl methyl ether. The solid was triturated... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amine | c1ccccc1 | null | c1cncnc1.c1ccccc1 | HO- | CN(C)C=O | null | 18 | C[C@@H](N)c1ccccc1.N#CN=C(Nc1cncnc1)Oc1ccccc1>CN(C)C=O>C[C@@H](NC(=NC#N)Nc1cncnc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f04f23e0e7f145c18e74c42a102f01f6 | COC(C)=O.OCC(CO)CCc1ccc(Br)cc1>>CC(=O)OC[C@@H](CO)CCc1ccc(Br)cc1 | BrC1=CC=C(C=C1)CCC(CO)CO.C(C)(=O)OC>>C(C)(=O)OC[C@H](CCC1=CC=C(C=C1)Br)CO | CO[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH:6]([CH2:7][OH:8])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@@H:6]([CH2:7][OH:8])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1 | COC(C)=O.OCC(CO)CCc1ccc(Br)cc1 | CC(=O)OC[C@@H](CO)CCc1ccc(Br)cc1 | null | null | null | Acylation | Transesterification | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | c1ccccc1 | C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | null | null | To a solution of 4.6 g of 4-(4-bromophenyl)-2-(hydroxymethyl)butanol in 300 ml of methyl acetate was added 33.1 g of the above PPL preparation. The mixture was stirred while the progress of the reaction was monitored by HPLC method A. When the consumption of diol was complete, the mixture was immediately filtered and t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | COC(C)=O.OCC(CO)CCc1ccc(Br)cc1>>CC(=O)OC[C@@H](CO)CCc1ccc(Br)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1445eac5a4014671ac02711e701552ec | COc1ccc(Br)cc1C=O.NO>>COc1ccc(Br)cc1C#N | C(C)(=O)OC(C)=O.BrC1=CC=C(C(C=O)=C1)OC.Cl.NO.C(C)(=O)[O-].[Na+].[OH-].[Na+]>>BrC=1C=CC(=C(C#N)C1)OC | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Br:7])[cH:8]1.O[NH2:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[C:10]#[N:11] | COc1ccc(Br)cc1C=O.NO | COc1ccc(Br)cc1C#N | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | 748a00525e7f639e600a6b1229bb8ce947b6e2e96d815c0b05b54470e6cdbc2a | a27285857ea2428fb666a281ae1a2b961eec077cb33a106e48534c99bfe3d865 | c1ccccc1 | O-[NH2;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 100 | CELSIUS | 1 | HOUR | A mixture of 5-Bromo-o-anisaldehyde (6.45 g), hydroxylamine hydrochloride (2.2 g), sodium acetate (4.1 g) and acetic acid (20 mL) was heated at 100° C. with stirring for 1 h. Acetic anhydride was added (20 mL) and the mixture was refluxed for 8 h. The reaction mixture was poured onto ice water and the mixture was made ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile | null | null | c1ccccc1 | HO- | C(C)(=O)O | 100 | 1 | COc1ccc(Br)cc1C=O.NO>C(C)(=O)O>COc1ccc(Br)cc1C#N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d974bf9235d9408fbea0e1003a2cf886 | COc1ccc(Br)cc1C(=N)N.O=C(CO)CO>>COc1ccc(Br)cc1-c1ncc(CO)[nH]1 | BrC=1C=CC(=C(C(=N)N)C1)OC.OCC(=O)CO.[Cl-].[NH4+].[OH-].[NH4+]>>BrC=1C=CC(=C(C1)C=1NC(=CN1)CO)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[C:10](=[NH:11])[NH2:16].O=[C:13]([CH2:12]O)[CH2:14][OH:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1-[c:10]1[n:11][cH:12][c:13]([CH2:14][OH:15])[nH:16]1 | COc1ccc(Br)cc1C(=N)N.O=C(CO)CO | COc1ccc(Br)cc1-c1ncc(CO)[nH]1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 7040ca240901ea801ff60cc2b70327e852de1f0d8d0e034873a53538d68125d0 | 099961450c7564589a83083f79d293e700761052a76093ed07ed90267b634558 | c1ccc(-c2ncc[nH]2)cc1 | O-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3]-[O;D1;H1:4].[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]):[c:12]:[c:13]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[c;H0;D3;+0:9]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3]-[O;D1;H1:4]):[nH;D2;+0:10]:1):[c:12]:[c:13] | null | [] | 90 | CELSIUS | null | null | A mixture of 5-Bromo-2-methoxy-benzamidine (1.5 g), 1,3-dihydroxy-acetone dimer (1.0 g), ammonium chloride (1.3 g), tetrahydrofuran (3 mL) and concentrated aqueous ammonium hydroxide (10 mL) was heated at 90° C. for 3 h. The reaction mixture was chilled on ice and the precipitated product was collected and recrystalliz... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary amine | null | null | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HO- | O1CCCC1 | 90 | null | COc1ccc(Br)cc1C(=N)N.O=C(CO)CO>O1CCCC1>COc1ccc(Br)cc1-c1ncc(CO)[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-560b22e6b12f490aa00ae31becc38836 | O=S(Cl)Cl.OCc1ccc(Cl)nc1>>ClCc1ccc(Cl)nc1 | ClC1=NC=C(C=C1)CO.S(=O)(Cl)Cl>>ClC1=NC=C(C=C1)CCl | O=S(Cl)[Cl:1].O[CH2:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:9]1>>[Cl:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:9]1 | O=S(Cl)Cl.OCc1ccc(Cl)nc1 | ClCc1ccc(Cl)nc1 | null | null | ClCCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 95.7 | [{"value": 95.7, "product": "ClC1=NC=C(C=C1)CCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 70.3 g of 2-chloro-5-(hydroxymethyl) pyridine and 50 ml of 1,2-dichloroethane was dropwise added to a mixture of 87.4 g of thionyl chloride and 100 ml of 1,2-dichloroethane during 30 minutes in a water bath of 5°-20° C. The mixture was stirred for an hour and a half at room temperature and for 4 hours and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | HCl | ClCCCl | null | 4 | O=S(Cl)Cl.OCc1ccc(Cl)nc1>ClCCCl>ClCc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-62a17c750f504895890fca3760e1030c | ClCc1ccc(Cl)nc1.N>>NCc1ccc(Cl)nc1 | [OH-].[Na+].ClC1=NC=C(C=C1)CCl.O.N>>NCC=1C=CC(=NC1)Cl | Cl[CH2:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:9]1.[NH3:1]>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:9]1 | ClCc1ccc(Cl)nc1.N | NCc1ccc(Cl)nc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 141e57e7b467ef1af7390eea74d28aab60295f9a2146f5e9c32bccbe8d06fe6f | 14467bdca40cd5f74ac0c15917a737e6b818cd36a46b0668375c9383066b6e0b | c1ccncc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 58.1 | [{"value": 58.1, "product": "NCC=1C=CC(=NC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A mixture of 14.99 g of 2-chloro-5-(chloromethyl) pyridine, 63.01 g of 25% ammonia water and 60 ml of acetonitrile in a stainless steel autoclave was stirred for 2 hours in an oil bath of 80° C. After adding 12.3 g of 30% sodium hydroxide aqueous solution, the reaction mixture was concentrated. The residue to which 200... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary amine | null | null | c1ccncc1 | HCl | C(C)#N | 80 | 2 | ClCc1ccc(Cl)nc1.N>C(C)#N>NCc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-15349f90d5234b6aaef6d84c3387a9b8 | CN.ClCc1ccc(Cl)nc1>>CNCc1ccc(Cl)nc1 | ClC1=NC=C(C=C1)CCl.CN>>ClC1=NC=C(C=C1)CNC | [CH3:1][NH2:2].Cl[CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[n:9][cH:10]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[n:9][cH:10]1 | CN.ClCc1ccc(Cl)nc1 | CNCc1ccc(Cl)nc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccncc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 60.3 | [{"value": 60.3, "product": "ClC1=NC=C(C=C1)CNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 15.05 g of 2-chloro-5-(chloromethyl) pyridine and 50 ml of acetonitrile was dropwise added to a mixture of 36 g of 40% methylamine aqueous solution and 200 ml of acetonitrile during an hour at room temperature and stirred for an hour and a half. The reaction mixture was concentrated. The resulting residue ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccncc1 | HCl | C(C)#N | null | null | CN.ClCc1ccc(Cl)nc1>C(C)#N>CNCc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ddec34ddcf93426ea32b4d8fd7bea2af | CN=C=S.Nc1ccc(Cl)nc1>>CNC(=S)Nc1ccc(Cl)nc1 | ClC1=NC=C(C=C1)N.CN=C=S.CN=C=S>>ClC1=CC=C(C=N1)NC(=S)NC | [CH3:1][N:2]=[C:3]=[S:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1>>[CH3:1][NH:2][C:3](=[S:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1 | CN=C=S.Nc1ccc(Cl)nc1 | CNC(=S)Nc1ccc(Cl)nc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | c1ccncc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[S;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[S;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | 70.6 | [{"value": 70.6, "product": "ClC1=CC=C(C=N1)NC(=S)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.07 g of 2-chloro-5-aminopyridine, 2.55 g of methyl isothiocyanate and 30 ml of acetonitrile was refluxed for 13.5 hours, to which 0.70 g of additional methyl isothiocyanate was added and the mixture was refluxed for 3.5 hours. The reaction mixture was concentrated, and the residue was purified by a colum... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccncc1 | null | C(C)#N | null | null | CN=C=S.Nc1ccc(Cl)nc1>C(C)#N>CNC(=S)Nc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0ae21637521349e3a5ce4e7dee9dae97 | CCNCC.CSC(=N)N[N+](=O)[O-]>>CCN(CC)C(=N)N[N+](=O)[O-] | CSC(N[N+](=O)[O-])=N.C(C)NCC>>C(C)N(C(=N)N[N+](=O)[O-])CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].CS[C:6](=[NH:7])[NH:8][N+:9](=[O:10])[O-:11]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[NH:7])[NH:8][N+:9](=[O:10])[O-:11] | CCNCC.CSC(=N)N[N+](=O)[O-] | CCN(CC)C(=N)N[N+](=O)[O-] | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 05b64877b6cb13a4648efb144268a1124b146a9cb0b909480944b9bd8a435a49 | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | null | C-S-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[C;D1;H3:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C;D1;H3:11]>>[C;D1;H3:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C;D1;H3:11])-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6] | 53.1 | [{"value": 53.1, "product": "C(C)N(C(=N)N[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 6 | HOUR | To a mixture of 1.35 g of S-methyl-N-nitroisothiourea and 5 ml of acetonitrile was added 0.88 g of diethylamine, followed by stirring for 6 hours in an oil bath of 60° C. The reaction mixture was concentrated and the residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (20:1)] to... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | null | null | null | Other | C(C)#N | 60 | 6 | CCNCC.CSC(=N)N[N+](=O)[O-]>C(C)#N>CCN(CC)C(=N)N[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7b39bae98337414e9faa77d40fa49602 | C1CCNC1.CSC(=N)N[N+](=O)[O-]>>N=C(N[N+](=O)[O-])N1CCCC1 | CSC(N[N+](=O)[O-])=N.N1CCCC1>>[N+](=O)([O-])NC(=N)N1CCCC1 | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.CS[C:2](=[NH:1])[NH:3][N+:4](=[O:5])[O-:6]>>[NH:1]=[C:2]([NH:3][N+:4](=[O:5])[O-:6])[N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1 | C1CCNC1.CSC(=N)N[N+](=O)[O-] | N=C(N[N+](=O)[O-])N1CCCC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 868057ed7bfa967ecc158180c4e484530f29269be5b11d1bfeff00362dda8c2e | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | C1CCNC1 | C-S-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[C:7]1-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[N;D1;H1:2]=[C;H0;D3;+0:1](-[#7:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:11]-[C:10]-1 | 93.1 | [{"value": 93.1, "product": "[N+](=O)([O-])NC(=N)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 1.0 g of S-methyl-N-nitroisothiourea and 15 ml of acetonitrile was dropwise added 0.61 g of pyrrolidine within 2 minutes, followed by stirring for 30 minutes. The reaction mixture was concentrated. The resulting precipitate was washed with ethyl ether to afford 1.09 g of 1-(N-nitroamidino)pyrrolidine as... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | Other | C(C)#N | null | 0.5 | C1CCNC1.CSC(=N)N[N+](=O)[O-]>C(C)#N>N=C(N[N+](=O)[O-])N1CCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-202a43352c1f4b68988506e8d117a5f3 | CC(=O)OC(C)=O.CSC(=N)N[N+](=O)[O-]>>CSC(=N[N+](=O)[O-])NC(C)=O | CSC(N[N+](=O)[O-])=N.C(C)(=O)OC(C)=O>>C(C)(=O)NC(SC)=N[N+](=O)[O-] | CC(=O)O[C:9]([CH3:10])=[O:11].[CH3:1][S:2][C:3]([NH:4][N+:5](=[O:6])[O-:7])=[NH:8]>>[CH3:1][S:2][C:3](=[N:4][N+:5](=[O:6])[O-:7])[NH:8][C:9]([CH3:10])=[O:11] | CC(=O)OC(C)=O.CSC(=N)N[N+](=O)[O-] | CSC(=N[N+](=O)[O-])NC(C)=O | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 5179bd03f895b7267efad9d9919c77d0bc7bead4953793964c6224650ae47b34 | ee9858b53576953e7a3de0544c9c100a5576f5cd0c0f2d39deb4c9decc8e363a | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[#16:5]-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[NH;D2;+0:8]-[#7;+:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:7]-[C;H0;D3;+0:6](-[#16:5]-[C;D1;H3:4])=[N;H0;D2;+0:8]-[#7;+:9](-[O;-;D1;H0:10])=[O;D1;H0:11] | 77.8 | [{"value": 77.8, "product": "C(C)(=O)NC(SC)=N[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a mixture of 5.0 g of S-methyl-N-nitroisothiourea and 25 ml of pyridine was dropwise added 11.3 g of acetic anhydride at room temperature, taking for 10 minutes, followed by stirring for 5 hours at the same temperature. The reaction mixture was concentrated, and the residue was poured into 50 ml of 2N-hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Anhydride.Monosulfide | Hydrazone.Secondary amide | null | null | null | HO- | N1=CC=CC=C1 | null | 0.166667 | CC(=O)OC(C)=O.CSC(=N)N[N+](=O)[O-]>N1=CC=CC=C1>CSC(=N[N+](=O)[O-])NC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e77115f6fff944f5b5d1ed887385f92e | CCOC(=O)C(Cl)C=O.NC(=S)C(F)(F)F>>CCOC(=O)c1cnc(C(F)(F)F)s1 | FC(C(=S)N)(F)F.ClC(C(=O)OCC)C=O>>FC(C=1SC(=CN1)C(=O)OCC)(F)F | O=[CH:7][CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][C:9]([C:10]([F:11])([F:12])[F:13])=[S:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([C:10]([F:11])([F:12])[F:13])[s:14]1 | CCOC(=O)C(Cl)C=O.NC(=S)C(F)(F)F | CCOC(=O)c1cnc(C(F)(F)F)s1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | ca1a491634351402ba53e022aaddc0a4c7ec0639045153b7668e78d316c6754f | b332eb5ea501618d8dbac38c7e3242fcefa783e31f17b6ca5d4aaeb74530fc69 | c1cscn1 | Cl-[CH;D3;+0:1](-[CH;D2;+0:2]=O)-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[S;H0;D1;+0:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[n;H0;D2;+0:12]:[c;H0;D3;+0:11](-[C:8](-[F;D1;H0:7])(-[F;D1;H0:9])-[F;D1;H0:10]):[s;H0;D2;+0:13... | 24.7 | [{"value": 24.7, "product": "FC(C=1SC(=CN1)C(=O)OCC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | A mixture of 11.22 g of 2,2,2,-trifluorothioacetamide and 10.14 g of ethyl 2-chloro-2-formylacetate was stirred for 30 minutes in an oil bath of 70° C. and then for 1.5 hours in an oil bath of 100° C., to which 100 ml of dichloromethane were added. After removing an insoluble substance, the mixture was concentrated and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Ester.Thioamide | Ester | null | c1cscn1 | c1cscn1 | HCl | ClCCl | 70 | 0.5 | CCOC(=O)C(Cl)C=O.NC(=S)C(F)(F)F>ClCCl>CCOC(=O)c1cnc(C(F)(F)F)s1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ea67113aecf847ec8fb13bda32202f05 | CCN(Cc1ccc(Cl)nc1)C(=NC#N)SC.CN>>CCN(Cc1ccc(Cl)nc1)C(=NC#N)NC | ClC1=CC=C(C=N1)CN(C(SC)=NC#N)CC.CN>>ClC1=CC=C(C=N1)CN(C(=NC#N)NC)CC | CS[C:12]([N:3]([CH2:2][CH3:1])[CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][cH:11]1)=[N:13][C:14]#[N:15].[NH2:16][CH3:17]>>[CH3:1][CH2:2][N:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][cH:11]1)[C:12](=[N:13][C:14]#[N:15])[NH:16][CH3:17] | CCN(Cc1ccc(Cl)nc1)C(=NC#N)SC.CN | CCN(Cc1ccc(Cl)nc1)C(=NC#N)NC | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccncc1 | C-S-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[#7:5](-[C:6])-[C:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[C:6]-[#7:5](-[C:7])-[C;H0;D3;+0:1](=[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:9]-[C;D1;H3:8] | 81.4 | [{"value": 81.4, "product": "ClC1=CC=C(C=N1)CN(C(=NC#N)NC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 0.42 g of 1-(6-chloro-3-pyridylmethyl)-3-cyano-1-ethyl-2-methylisothiourea and 5 ml of acetonitrile was added each 0.5 g of 40% methylamine aqueous solution at an hour interval in total six time (3.0 g), while refluxing and stirring. The reaction mixture was stirred for 6 hours in total. Then, the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccncc1 | Other | C(C)#N | null | null | CCN(Cc1ccc(Cl)nc1)C(=NC#N)SC.CN>C(C)#N>CCN(Cc1ccc(Cl)nc1)C(=NC#N)NC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e223f8a6637044d994743a5abd5433cf | CN(C)C(=N)N[N+](=O)[O-].ClCc1ccc(Cl)nc1>>CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | [H-].[Na+].CN(C(=N)N[N+](=O)[O-])C.ClC1=NC=C(C=C1)CCl>>ClC1=CC=C(C=N1)CNC(=N[N+](=O)[O-])N(C)C | [CH3:1][N:2]([CH3:3])[C:4]([NH:5][N+:6](=[O:7])[O-:8])=[NH:9].Cl[CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]1>>[CH3:1][N:2]([CH3:3])[C:4](=[N:5][N+:6](=[O:7])[O-:8])[NH:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]1 | CN(C)C(=N)N[N+](=O)[O-].ClCc1ccc(Cl)nc1 | CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | null | null | CN(C)C=O | Protection | OtherReaction | 6bc260a19edaf0a9ae100808188306f3bdd7a4767e9712a41beac901d2272dbe | ee9f583c221e42a578248439e705971d77c8a525da3f66f469ff1a1aba186bf7 | c1ccncc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[C;H0;D3;+0:10](=[NH;D1;+0:11])-[NH;D2;+0:12]-[#7;+:13](-[O;-;D1;H0:14])=[O;D1;H0:15]>>[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[C;H0;D3;+0:10](=[N;H0;D2;+0:12]-[#7;+:13](-[O;-;D1;H0:14])=[O;D1;H0:15])-[NH;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3])... | 31.9 | [{"value": 31.9, "product": "ClC1=CC=C(C=N1)CNC(=N[N+](=O)[O-])N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of 0.44 g of 60% sodium hydride (in mineral oil) in 10 ml of DMF was added 1.32 g of N,N-dimethyl-N'-nitroguanidine during 20 minutes at room temperature. After stirring for 10 minutes, 1.62 g of 2-chloro-5-(chloromethyl)pyridine was added to the mixture in 5 minutes, and stirred for 2 hours at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide | Hydrazone.Secondary amine | null | null | c1ccncc1 | HCl | CN(C)C=O | null | 0.166667 | CN(C)C(=N)N[N+](=O)[O-].ClCc1ccc(Cl)nc1>CN(C)C=O>CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a0d445180fdc49e09290c6b0997b3fc5 | CNC(=N[N+](=O)[O-])SC.NCc1ccc(Cl)nc1>>CNC(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | CNC(SC)=N[N+](=O)[O-].NCC=1C=CC(=NC1)Cl>>ClC1=CC=C(C=N1)CNC(=N[N+](=O)[O-])NC | CS[C:3]([NH:2][CH3:1])=[N:4][N+:5](=[O:6])[O-:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[n:15][cH:16]1>>[CH3:1][NH:2][C:3](=[N:4][N+:5](=[O:6])[O-:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[n:15][cH:16]1 | CNC(=N[N+](=O)[O-])SC.NCc1ccc(Cl)nc1 | CNC(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 883fee3f84362c063113a06e86cdc3a3bf94029e9de373b9cf505859a3b7d61a | 07cba6ae0650a80cbffb2d3f121f3eee9c0a2be72294ae9df786d5ac7452446b | c1ccncc1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])=[#7:4]-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7].[#7;a:8]:[c:9]:[c:10]-[C:11]-[NH2;D1;+0:12]>>[#7;a:8]:[c:9]:[c:10]-[C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])=[#7:4]-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7] | 34 | [{"value": 34.0, "product": "ClC1=CC=C(C=N1)CNC(=N[N+](=O)[O-])NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.45 g of 1,2-dimethyl-3-nitroisothiourea, 0.43 g of 5-(aminomethyl)-2-chloropyridine and 25 ml of ethanol was refluxed for 6 hours and concentrated. The residue was purified by a column chromatography [developing solvent: chloroform-ethanol (5:1)] to afford 0.25 g of 1-(6-chloro-3-pyridylmethyl)-3-methyl-... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Primary amine.Monosulfide | Hydrazone.Secondary amine | null | null | c1ccncc1 | Other | C(C)O | null | null | CNC(=N[N+](=O)[O-])SC.NCc1ccc(Cl)nc1>C(C)O>CNC(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eb6b1e439c704066992f2dc01030ffe1 | CNCc1ccc(Cl)nc1.CSC(=N)N[N+](=O)[O-]>>CN(Cc1ccc(Cl)nc1)C(N)=N[N+](=O)[O-] | CSC(N[N+](=O)[O-])=N.ClC1=NC=C(C=C1)CNC>>ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])N)C | [CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[n:9][cH:10]1.CS[C:11](=[NH:12])[NH:13][N+:14](=[O:15])[O-:16]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[n:9][cH:10]1)[C:11]([NH2:12])=[N:13][N+:14](=[O:15])[O-:16] | CNCc1ccc(Cl)nc1.CSC(=N)N[N+](=O)[O-] | CN(Cc1ccc(Cl)nc1)C(N)=N[N+](=O)[O-] | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 8492a5db8ba38868aaf8f542781290a626677d540b1f2ec0ede58678eb181444 | a6d74864a38e00e28e7bd6e7158dd0ac81d24c0ac9fdb6de46f9333a7dc0e609 | c1ccncc1 | C-S-[C;H0;D3;+0:1](=[NH;D1;+0:2])-[NH;D2;+0:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[#7;a:7]:[c:8]:[c:9]-[C:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[#7;a:7]:[c:8]:[c:9]-[C:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[N;H0;D2;+0:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6] | 31.2 | [{"value": 31.2, "product": "ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.676 g of S-methyl-N-nitroisothiourea, 0.783 g of 2-chloro-5-(methylaminomethyl)pyridine and 6 ml of acetonitrile was refluxed for 17 hours, and concentrated. The residue was recrystallized from ethanol to obtain 0.38 g of 1-(6-chloro-3-pyridylmethyl)-1-methyl-2-nitroguanidine (Compound No. 7).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Secondary amine.Monosulfide | Hydrazone.Primary amine.Tertiary amine | null | null | c1ccncc1 | Other | C(C)#N | null | null | CNCc1ccc(Cl)nc1.CSC(=N)N[N+](=O)[O-]>C(C)#N>CN(Cc1ccc(Cl)nc1)C(N)=N[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cfb1593aec87497ca8ab97928a86ad43 | CN.CSC(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1>>CNC(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 | ClC1=CC=C(C=N1)CN(C(SC)=N[N+](=O)[O-])C.CN>>ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])NC)C | [CH3:1][NH2:2].CS[C:3](=[N:4][N+:5](=[O:6])[O-:7])[N:8]([CH3:9])[CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]1>>[CH3:1][NH:2][C:3](=[N:4][N+:5](=[O:6])[O-:7])[N:8]([CH3:9])[CH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]1 | CN.CSC(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 | CNC(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 883fee3f84362c063113a06e86cdc3a3bf94029e9de373b9cf505859a3b7d61a | 07cba6ae0650a80cbffb2d3f121f3eee9c0a2be72294ae9df786d5ac7452446b | c1ccncc1 | C-S-[C;H0;D3;+0:1](=[#7:2]-[#7;+:3](-[O;-;D1;H0:4])=[O;D1;H0:5])-[#7:6](-[C:7])-[C;D1;H3:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C:7]-[#7:6](-[C;D1;H3:8])-[C;H0;D3;+0:1](=[#7:2]-[#7;+:3](-[O;-;D1;H0:4])=[O;D1;H0:5])-[NH;D2;+0:10]-[C;D1;H3:9] | 72.8 | [{"value": 72.8, "product": "ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])NC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | HOUR | A mixture of 0.82 g of 1-(6-chloro-3-pyridyl-methyl)-1,2-dimethyl-3-nitroisothiourea, 0.464 g of 40% methylamine aqueous solution and 10 ml of acetonitrile was stirred for 2 hours at 70° C., and concentrated. The residue was purified by a column chromatography developing solution: dichloromethane-methanol [10:1]) to af... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Primary amine.Monosulfide | Hydrazone.Secondary amine | null | null | c1ccncc1 | Other | C(C)#N | 70 | 2 | CN.CSC(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1>C(C)#N>CNC(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1bca00ba48324653a225f7149bb02d40 | N=C(N)N[N+](=O)[O-].NCc1cccnc1>>N=C(NCc1cccnc1)N[N+](=O)[O-] | [N+](=O)([O-])NC(=N)N.NCC=1C=NC=CC1>>[N+](=O)([O-])NC(=N)NCC=1C=NC=CC1 | N[C:2](=[NH:1])[NH:11][N+:12](=[O:13])[O-:14].[NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[NH:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][N+:12](=[O:13])[O-:14] | N=C(N)N[N+](=O)[O-].NCc1cccnc1 | N=C(NCc1cccnc1)N[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 3a57d6854f77082d71e7a55c408a198c46ae4aa81ffd8dae0cb36847fdc88419 | d3d09bdf4511175432d42d1477b84cc1bf1a82e217a37c22fa170c7e0beabdc1 | c1ccncc1 | N-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[#7;a:7]:[c:8]:[c:9]-[C:10]-[NH2;D1;+0:11]>>[#7;a:7]:[c:8]:[c:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[N;D1;H1:2])-[#7:3]-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6] | 48.3 | [{"value": 48.3, "product": "[N+](=O)([O-])NC(=N)NCC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of 0.53 g of nitroguanidine, 0.61 g of 3-(aminomethyl)pyridine and 10 ml of water was stirred for 1.5 hours at 70°-80° C. and allowed to stand over night at room temperature. The precipitate collected by filtration was washed with ethanol to obtain 0.48 g of N-nitro-N'-(3-pyridylmethyl)guanidine (Compound No.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Secondary amine | null | null | c1ccncc1 | Other | O | null | 1.5 | N=C(N)N[N+](=O)[O-].NCc1cccnc1>O>N=C(NCc1cccnc1)N[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bdd54f199ffc42b194e4d4d34c788ac0 | CI.CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1>>CN(C)C(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 | C(C)(=O)O.IC.ClC1=CC=C(C=N1)CNC(=N[N+](=O)[O-])N(C)C.[H-].[Na+]>>ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])N(C)C)C | I[CH3:10].[CH3:1][N:2]([CH3:3])[C:4](=[N:5][N+:6](=[O:7])[O-:8])[NH:9][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[n:17][cH:18]1>>[CH3:1][N:2]([CH3:3])[C:4](=[N:5][N+:6](=[O:7])[O-:8])[N:9]([CH3:10])[CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[n:17][cH:18]1 | CI.CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | CN(C)C(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccncc1 | I-[CH3;D1;+0:1].[#7:2]-[C:3](=[#7:4]-[#7;+:5])-[NH;D2;+0:6]-[C:7]-[c:8]:[c:9]:[#7;a:10]>>[#7:2]-[C:3](=[#7:4]-[#7;+:5])-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[C:7]-[c:8]:[c:9]:[#7;a:10] | null | [] | null | null | 30 | MINUTE | To a mixture of 0.24 g of 1-(6-chloro-3-pyridylmethyl)-3,3-dimethyl-2-nitroguanidine (Compound No. 6) and 6 ml of dry tetrahydrofuran (THF) was added 0.045 g of 60% sodium hydride (in mineral oil) at room temperature, followed by stirring for 30 minutes. A solution of 0.16 g of iodomethane in 1 ml of THF was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccncc1 | HI | O1CCCC1 | null | 0.5 | CI.CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1>O1CCCC1>CN(C)C(=N[N+](=O)[O-])N(C)Cc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-00bb20223361438ca1a237b149f0cebc | CC(=O)OC=O.CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1>>CN(C)C(=N[N+](=O)[O-])N(C=O)Cc1ccc(Cl)nc1 | [H-].[Na+].ClC1=CC=C(C=N1)CNC(=N[N+](=O)[O-])N(C)C.C(=O)OC(C)=O>>ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])N(C)C)C=O | CC(=O)O[CH:10]=[O:11].[CH3:1][N:2]([CH3:3])[C:4](=[N:5][N+:6](=[O:7])[O-:8])[NH:9][CH2:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[n:18][cH:19]1>>[CH3:1][N:2]([CH3:3])[C:4](=[N:5][N+:6](=[O:7])[O-:8])[N:9]([CH:10]=[O:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[n:18][cH:19]1 | CC(=O)OC=O.CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | CN(C)C(=N[N+](=O)[O-])N(C=O)Cc1ccc(Cl)nc1 | null | null | C1CCOC1 | Acylation | OtherReaction | d178cf3b7716e98c877fb8e7fd543bf80bf7ca766a3397de1d00b85a8dc4cbce | a915e3923d0587efcb1952fd34158dabaf6121028d5282bdf34c96ebf77c7ff6 | c1ccncc1 | C-C(=O)-O-[CH;D2;+0:1]=[O;D1;H0:2].[#7:3]-[C:4](=[#7:5]-[#7;+:6])-[NH;D2;+0:7]-[C:8]-[c:9]:[c:10]:[#7;a:11]>>[#7:3]-[C:4](=[#7:5]-[#7;+:6])-[N;H0;D3;+0:7](-[C:8]-[c:9]:[c:10]:[#7;a:11])-[CH;D2;+0:1]=[O;D1;H0:2] | 34.7 | [{"value": 34.7, "product": "ClC1=CC=C(C=N1)CN(C(=N[N+](=O)[O-])N(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 0.26 g of 1-(6-chloro-3-pyridylmethyl)-3,3-dimethyl-2-nitroguanidine (Compound No. 6) and 3 ml of dry THF was added 0.08 g of 60% sodium hydride (in mineral oil) in a water bath of 20° C., followed by stirring for 30 minutes. A solution of 0.26 g of acetic formic anhydride in 0.5 ml of THF was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Secondary amine | Tertiary amide | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 0.5 | CC(=O)OC=O.CN(C)C(=N[N+](=O)[O-])NCc1ccc(Cl)nc1>C1CCOC1>CN(C)C(=N[N+](=O)[O-])N(C=O)Cc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-deb5e3067b824df78fe41cdb691c4394 | CNC(=S)Nc1ccc(Cl)nc1.N#CN>>CNC(=NC#N)Nc1ccc(Cl)nc1 | ClC1=CC=C(C=N1)NC(=S)NC.N#CN.C1(CCCCC1)N=C=NC1CCCCC1>>ClC1=CC=C(C=N1)NC(=NC#N)NC | S=[C:3]([NH:2][CH3:1])[NH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[n:13][cH:14]1.[NH2:4][C:5]#[N:6]>>[CH3:1][NH:2][C:3](=[N:4][C:5]#[N:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[n:13][cH:14]1 | CNC(=S)Nc1ccc(Cl)nc1.N#CN | CNC(=NC#N)Nc1ccc(Cl)nc1 | null | C(C)N(C(C)C)C(C)C | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | a1eed482de64f210d0aa14250aff2e95896d7c125f5ef11d8db9968ccb473ed2 | 42f73345310a096555cb36ab9248c959f01ac661f032df704842b690aa63e637 | c1ccncc1 | S=[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])-[#7:4]-[c:5]:[c:6]:[#7;a:7].[N;D1;H0:8]#[C:9]-[NH2;D1;+0:10]>>[#7;a:7]:[c:6]:[c:5]-[#7:4]-[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])=[N;H0;D2;+0:10]-[C:9]#[N;D1;H0:8] | 29 | [{"value": 29.0, "product": "ClC1=CC=C(C=N1)NC(=NC#N)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 34 | HOUR | A mixture of 1.03 g of 1-(6-chloro-3-pyridyl)-3-methylthiourea, 0.32 g of cyanamide, 1.58 g of dicyclohexylcarbodiimide, 3 drops of ethyl diisopropylamine and 10 ml of acetonitrile was stirred for 34 hours at room temperature and filtered to collect an insoluble substance. The insoluble substance was recrystallized fro... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Thiourea | null | null | null | c1ccncc1 | Other | C(C)N(C(C)C)C(C)C.C(C)#N | null | 34 | CNC(=S)Nc1ccc(Cl)nc1.N#CN>C(C)N(C(C)C)C(C)C.C(C)#N>CNC(=NC#N)Nc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d848d8ca30a34c3cba54395a638315e6 | CNC(=N[N+](=O)[O-])SC.NCc1cnc(Br)s1>>CNC(=N[N+](=O)[O-])NCc1cnc(Br)s1 | NCC1=CN=C(S1)Br.CNC(SC)=N[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+]>>BrC=1SC(=CN1)CNC(=N[N+](=O)[O-])NC | CS[C:3]([NH:2][CH3:1])=[N:4][N+:5](=[O:6])[O-:7].[NH2:8][CH2:9][c:10]1[cH:11][n:12][c:13]([Br:14])[s:15]1>>[CH3:1][NH:2][C:3](=[N:4][N+:5](=[O:6])[O-:7])[NH:8][CH2:9][c:10]1[cH:11][n:12][c:13]([Br:14])[s:15]1 | CNC(=N[N+](=O)[O-])SC.NCc1cnc(Br)s1 | CNC(=N[N+](=O)[O-])NCc1cnc(Br)s1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 883fee3f84362c063113a06e86cdc3a3bf94029e9de373b9cf505859a3b7d61a | 07cba6ae0650a80cbffb2d3f121f3eee9c0a2be72294ae9df786d5ac7452446b | c1cscn1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])=[#7:4]-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7].[#16;a:8]:[c:9](-[C:10]-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#16;a:8]:[c:9](-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](-[#7:2]-[C;D1;H3:3])=[#7:4]-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7]):[c:12]:[#7;a:13] | null | [] | 60 | CELSIUS | 45 | MINUTE | A mixture of 0.39 g of 5-(aminomethyl)-2-bromothiazole, 0.30 g of 1,2-dimethyl-3-nitroisothiourea, 0.58 g of cuprous bromide, 0.55 g of anhydrous potassium carbonate and 4 ml of dry acetonitrile was stirred in an oil bath of 60° C. for 45 minutes. The reaction mixture was purified by a column chromatography [developing... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Primary amine.Monosulfide | Hydrazone.Secondary amine | null | null | c1cscn1 | Other | C(C)#N | 60 | 0.75 | CNC(=N[N+](=O)[O-])SC.NCc1cnc(Br)s1>C(C)#N>CNC(=N[N+](=O)[O-])NCc1cnc(Br)s1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3a44a0a0754f42bd896f8b2d41e440db | CSC(=N[N+](=O)[O-])NC(C)=O.NCc1ccc(Cl)nc1>>CC(=O)NC(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | C(C)(=O)NC(SC)=N[N+](=O)[O-].NCC=1C=CC(=NC1)Cl>>C(C)(=O)NC(=N[N+](=O)[O-])NCC=1C=NC(=CC1)Cl | CS[C:5]([NH:4][C:2]([CH3:1])=[O:3])=[N:6][N+:7](=[O:8])[O-:9].[NH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[n:17][cH:18]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5](=[N:6][N+:7](=[O:8])[O-:9])[NH:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[n:17][cH:18]1 | CSC(=N[N+](=O)[O-])NC(C)=O.NCc1ccc(Cl)nc1 | CC(=O)NC(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 883fee3f84362c063113a06e86cdc3a3bf94029e9de373b9cf505859a3b7d61a | 07cba6ae0650a80cbffb2d3f121f3eee9c0a2be72294ae9df786d5ac7452446b | c1ccncc1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[C:3](-[C;D1;H3:4])=[O;D1;H0:5])=[#7:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9].[#7;a:10]:[c:11]:[c:12]-[C:13]-[NH2;D1;+0:14]>>[#7;a:10]:[c:11]:[c:12]-[C:13]-[NH;D2;+0:14]-[C;H0;D3;+0:1](-[#7:2]-[C:3](-[C;D1;H3:4])=[O;D1;H0:5])=[#7:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9] | 77 | [{"value": 77.0, "product": "C(C)(=O)NC(=N[N+](=O)[O-])NCC=1C=NC(=CC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 0.5 g of N-acetyl-S-methyl-N'-nitroisothiourea and 5 ml of acetonitrile was dropwise added a solution of 0.44 g of 5-(aminomethyl)-2-chloropyridine in 3 ml of acetonitrile under ice-cooling, followed by stirring for 30 minutes under ice-cooling. The reaction mixture was concentrated and the residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Primary amine.Monosulfide | Hydrazone.Secondary amine | null | null | c1ccncc1 | Other | C(C)#N | null | 0.5 | CSC(=N[N+](=O)[O-])NC(C)=O.NCc1ccc(Cl)nc1>C(C)#N>CC(=O)NC(=N[N+](=O)[O-])NCc1ccc(Cl)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-386686c9206a4c6aa84bffbf027ce9a8 | CC1(C)CC2(CC(C)(C)N1)OC1(CCCCCCCCCCC1)N(CC(O)CN1C(=O)C3(CC(C)(C)NC(C)(C)C3)OC13CCCCCCCCCCC3)C2=O>>CC(=O)OC(CN1C(=O)C2(CC(C)(C)N(C(C)=O)C(C)(C)C2)OC12CCCCCCCCCCC2)CN1C(=O)C2(CC(C)(C)N(C(C)=O)C(C)(C)C2)OC12CCCCCCCCCCC2 | OC(CN1C2(OC3(CC(NC(C3)(C)C)(C)C)C1=O)CCCCCCCCCCC2)CN2C1(OC3(CC(NC(C3)(C)C)(C)C)C2=O)CCCCCCCCCCC1>>C(C)(=O)OC(CN1C2(OC3(CC(N(C(C3)(C)C)C(C)=O)(C)C)C1=O)CCCCCCCCCCC2)CN2C1(OC3(CC(N(C(C3)(C)C)C(C)=O)(C)C)C2=O)CCCCCCCCCCC1 | [CH3:1][C:2]1([CH3:47])[NH:45][C:42]([CH3:43])([CH3:44])[CH2:41][C:40]2([C:38](=[O:39])[N:37]([CH2:36][CH:5]([OH:4])[CH2:6][N:7]3[C:8](=[O:48])[C:10]4([O:3][C:24]35[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]5)[CH2:11][C:16]([CH3:12])([CH3:17])[NH:15][C:19]([CH3:20])([CH3:21]... | CC1(C)CC2(CC(C)(C)N1)OC1(CCCCCCCCCCC1)N(CC(O)CN1C(=O)C3(CC(C)(C)NC(C)(C)C3)OC13CCCCCCCCCCC3)C2=O | CC(=O)OC(CN1C(=O)C2(CC(C)(C)N(C(C)=O)C(C)(C)C2)OC12CCCCCCCCCCC2)CN1C(=O)C2(CC(C)(C)N(C(C)=O)C(C)(C)C2)OC12CCCCCCCCCCC2 | null | null | C(C)(=O)OC(C)=O | Functional Group Addition | OtherReaction | bec8d8226d372e9657754e9deda9f6b7d98c6fb8cff60fac5ce6d3f01bda9190 | 9938faa317b01ea4d0b81f3f0ca2398d55d079d514fe060b980c46b6aa61685e | O=C1N(CCCN2C(=O)C3(CCNCC3)OC23CCCCCCCCCCC3)C2(CCCCCCCCCCC2)OC12CCNCC2 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-[C:4]-[C:5])-[O;H0;D2;+0:6]-[C;H0;D4;+0:7]2(-[C:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH;D2;+0:12]-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[CH3;D1;+0:15])-[CH2;D2;+0:16]-2)-[C;H0;D3;+0:17](=[O;H0;D1;+0:18])-[#7:19]-1-[C:20]-[C:21](-[OH;D1;+0:22])-[C:23]-[#7:24]1-[C:25]-[#8:26]-[C:27]2(-[C:28]-[C:... | null | [] | null | null | null | null | 39.2 g of 20,20'-(2-hydroxy-1,3-propanediyl)bis[2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosan-21-one] were dissolved in 400 cm3 of acetic anhydride and heated so strongly that about 200 cm3 of liquid distilled off over the course of 6 hours. The batch was then evaporated to dryness in vacuo, the resid... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Secondary alcohol.Secondary amine.Secondary amine | Ester.Ether.Tertiary amide.Tertiary amide.Tertiary amide | C1CCCCCC2(CCCCC1)[NH]CC1(CCNCC1)O2.C1CCCCCC2(CCCCC1)[NH]CC1(CCNCC1)O2 | C1CCCCCC2(CCCCC1)[NH]CC1(CC[NH]CC1)O2.C1CCCCCC2(CCCCC1)[NH]CC1(CC[NH]CC1)O2 | C1CCCCCC2(CCCCC1)[NH]CC1(CC[NH]CC1)O2.C1CCCCCC2(CCCCC1)[NH]CC1(CC[NH]CC1)O2 | Other | C(C)(=O)OC(C)=O | null | null | CC1(C)CC2(CC(C)(C)N1)OC1(CCCCCCCCCCC1)N(CC(O)CN1C(=O)C3(CC(C)(C)NC(C)(C)C3)OC13CCCCCCCCCCC3)C2=O>C(C)(=O)OC(C)=O>CC(=O)OC(CN1C(=O)C2(CC(C)(C)N(C(C)=O)C(C)(C)C2)OC12CCCCCCCCCCC2)CN1C(=O)C2(CC(C)(C)N(C(C)=O)C(C)(C)C2)OC12CCCCCCCCCCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1a15931d453046db9c51382d25968c1b | N#Cc1ccc(C=O)cc1.O=C1CCCCCC1>>N#Cc1ccc(C=C2CCCCCC2=O)cc1 | C(#N)C1=CC=C(C=O)C=C1.C1(CCCCCC1)=O>>C(#N)C1=CC=C(C=C1)C=C1C(CCCCC1)=O | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:17][cH:16]1.[CH2:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1=[O:15]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2=[O:15])[cH:16][cH:17]1 | N#Cc1ccc(C=O)cc1.O=C1CCCCCC1 | N#Cc1ccc(C=C2CCCCCC2=O)cc1 | null | null | P(O)(O)(O)=O | C-C Coupling | Aldol condensation | 3dec1fb6f9cde4e05db44511122c36b2d8ebf4e85b66c630348d8cca564268f5 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1CCCCCC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[C:10]>>[C:5]-[C:6]-[C;H0;D3;+0:7](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8](=[O;D1;H0:9])-[C:10] | null | [] | 100 | CELSIUS | null | null | A mixture of 20.0 g of 4-cyanobenzaldehyde, 30.5 g of cycloheptanone, and 200 mL of 85% phosphoric acid is heated for 1.5 h at 100° C. The mixture is cooled to room temperature, and filtered. The filtrate is poured into water (800 mL), and the precipitate is filtered, washed with water, and dried. The solid is purified... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | C1CCCCCC1 | C1CCCCCC1 | c1ccccc1.C1CCCCCC1 | HO- | P(O)(O)(O)=O | 100 | null | N#Cc1ccc(C=O)cc1.O=C1CCCCCC1>P(O)(O)(O)=O>N#Cc1ccc(C=C2CCCCCC2=O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2727f5fbd06a4d3584654f6341198823 | COc1ccc(Br)cc1C=O.NO>>COc1ccc(Br)cc1C#N | [OH-].[Na+].BrC1=CC=C(C(C=O)=C1)OC.Cl.NO.C(=O)[O-].[Na+]>>BrC=1C=CC(=C(C#N)C1)OC | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Br:7])[cH:8]1.O[NH2:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[C:10]#[N:11] | COc1ccc(Br)cc1C=O.NO | COc1ccc(Br)cc1C#N | null | null | C(=O)O | Miscellaneous | OtherReaction | 748a00525e7f639e600a6b1229bb8ce947b6e2e96d815c0b05b54470e6cdbc2a | a27285857ea2428fb666a281ae1a2b961eec077cb33a106e48534c99bfe3d865 | c1ccccc1 | O-[NH2;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 100 | CELSIUS | 1 | HOUR | A mixture of 6.45 g 5-bromo-o-anisaldehyde, 2.2 g of hydroxylamine hydrochloride, 4.1 g of sodium formate and 20 mL formic acid were heated at 100° C. with stirring for 1 h. The reaction mixture was poured onto ice water and the mixture was made basic by the careful addition of 50% sodium hydroxide. The product was ext... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile | null | null | c1ccccc1 | HO- | C(=O)O | 100 | 1 | COc1ccc(Br)cc1C=O.NO>C(=O)O>COc1ccc(Br)cc1C#N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d114fb2eb83049129c2f8def69a7c116 | COc1cccc(C#N)c1OC.C[Si](C)(C)N[Si](C)(C)C>>COc1cccc(C(=N)N)c1OC | Cl.C[Si](N[Si](C)(C)C)(C)C.C(CCC)[Li].COC1=C(C#N)C=CC=C1OC>>COC1=C(C(=N)N)C=CC=C1OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]#[N:9])[c:11]1[O:12][CH3:13].C[Si](C)(C)[NH:10][Si](C)(C)C>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[NH:9])[NH2:10])[c:11]1[O:12][CH3:13] | COc1cccc(C#N)c1OC.C[Si](C)(C)N[Si](C)(C)C | COc1cccc(C(=N)N)c1OC | null | null | CCCCCC.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | c69dc3918ec11d93fc440abf3e0b6efc258614217c8cf5c36cff1eaf4ee3899f | 827d5e8a7cbda8ac46afd217e51ef2b5ed64b3899fb0f9044671ad16df2d1214 | c1ccccc1 | C-[Si](-C)(-C)-[NH;D2;+0:1]-[Si](-C)(-C)-C.[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:1]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 10 | MINUTE | To a solution of 20 g 1,1,1,3,3,3-hexamethyldisilazane in 150 mL dry ether was added 5 mL 2.4M n-butyllithium in hexane. After 10 min at room temperature, 16.3 g 2,3-dimethoxybenzonitrile was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was then poured onto excess 3N ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary amine.Silyl protective group.Silyl protective group | Primary amine | null | null | c1ccccc1 | Other | CCCCCC.CCOCC | null | 0.166667 | COc1cccc(C#N)c1OC.C[Si](C)(C)N[Si](C)(C)C>CCCCCC.CCOCC>COc1cccc(C(=N)N)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0625e72398ed4dd58710646ee2d5a082 | COS(=O)(=O)OC.c1ccc(-c2ncc[nH]2)cc1>>Cn1ccnc1-c1ccccc1 | [Cl-].[NH4+].C1(=CC=CC=C1)C=1NC=CN1.C(C)(C)[N-]C(C)C.[Li+].S(=O)(=O)(OC)OC>>CN1C(=NC=C1)C1=CC=CC=C1 | COS(=O)(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][n:5][c:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | COS(=O)(=O)OC.c1ccc(-c2ncc[nH]2)cc1 | Cn1ccnc1-c1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-methylation | cd2ba7d8131691ffcb15dc3ca1da5447edd8b78d140f3b82779a267b9d6114c9 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(-c2ncc[nH]2)cc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[c:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[c:2] | null | [] | 0 | CELSIUS | 10 | MINUTE | A solution of 40 mL tetrahydrofuran containing 1.0 g of 2-phenylimidazole was cooled to 0° C. and 4 mL of 2M lithium diisopropylamide was added dropwise which resulted in the formation of a white suspension. The mixture was stirred for 10 min at 0° C. and then 0.7 mL of dimethyl sulfate was added. The reaction was allo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.166667 | COS(=O)(=O)OC.c1ccc(-c2ncc[nH]2)cc1>O1CCCC1>Cn1ccnc1-c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2c0cc496a601484484a0b9ec05dbbaef | C=O.Cc1c[nH]c(-c2ccccc2)n1.c1ccc(CC2CCNCC2)cc1>>Cc1[nH]c(-c2ccccc2)nc1CN1CCC(Cc2ccccc2)CC1 | CC=1N=C(NC1)C1=CC=CC=C1.C=O.C(C1=CC=CC=C1)C1CCNCC1>>CC1=C(N=C(N1)C1=CC=CC=C1)CN1CCC(CC1)CC1=CC=CC=C1 | O=[CH2:13].[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[nH:11][cH:12]1.[NH:14]1[CH2:15][CH2:16][CH:17]([CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([CH2:18][... | C=O.Cc1c[nH]c(-c2ccccc2)n1.c1ccc(CC2CCNCC2)cc1 | Cc1[nH]c(-c2ccccc2)nc1CN1CCC(Cc2ccccc2)CC1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 96776234213b3dd2b36e241fe4b7b05149b775b962c3ecc7a824743adfb94abd | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CC2CCN(Cc3c[nH]c(-c4ccccc4)n3)CC2)cc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[c:3]1:[cH;D2;+0:4]:[nH;D2;+0:5]:[c:6](-[c:7]):[n;H0;D2;+0:8]: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]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c:6](-[c:7]):[nH;D2;+0:8]:[c:3]:1-[C;D1;H3:2])-[C:12]-[C:13] | null | [] | 100 | CELSIUS | null | null | To a solution of 1 g of 1 methyl-2-phenylimidazole in 10 mL acetic acid were added 0.4 mL of 37% aqueous formaldehyde and 1.2 mL of 4-benzylpiperidine. The reaction mixture was heated at 100° C. for 10 hours and the acetic acid then removed by evaporated under reduced pressure. The residue was dissolved in water and ma... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1c[nH]cn1.C1CCNCC1 | c1c[nH]cn1.C1CC[NH]CC1 | c1c[nH]cn1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | C(C)(=O)O | 100 | null | C=O.Cc1c[nH]c(-c2ccccc2)n1.c1ccc(CC2CCNCC2)cc1>C(C)(=O)O>Cc1[nH]c(-c2ccccc2)nc1CN1CCC(Cc2ccccc2)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-21a6de5b6dff4930a1b4971decc73307 | CC(=O)[O-].CCNC(=O)C([O-])=S.NCC(=O)c1ccccc1>>CCOC(=O)c1nc(-c2ccccc2)c[nH]1 | C(C)(=O)O.C(C)NC(C(=S)[O-])=O.Cl.NCC(=O)C1=CC=CC=C1.C(C)(=O)[O-].[Na+]>>C1(=CC=CC=C1)C=1N=C(NC1)C(=O)OCC | CC(=O)[O-:3].O=[C:6]([C:4](=S)[O-:5])[NH:7][CH2:2][CH3:1].O=[C:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][NH2:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][nH:16]1 | CC(=O)[O-].CCNC(=O)C([O-])=S.NCC(=O)c1ccccc1 | CCOC(=O)c1nc(-c2ccccc2)c[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5a82c0f043645883ee69c1e8cf46e171d7ccd1fb94c2b266e1cb042f87a3c180 | bd2e4ae1a43ea793c5148ee7f3f6f0b005b5e2df6bfa3d3ebe2f20fff7f21e30 | c1ccc(-c2c[nH]cn2)cc1 | C-C(=O)-[O-;H0;D1:1].O=[C;H0;D3;+0:2](-[CH2;D2;+0:3]-[NH2;D1;+0:4])-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].O=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[CH2;D2;+0:12]-[C;D1;H3:13])-[C;H0;D3;+0:14](=S)-[O-;H0;D1:15]>>[C;D1;H3:13]-[CH2;D2;+0:12]-[O;H0;D2;+0:1]-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[c;H... | null | [] | null | null | null | null | A mixture of 3 g of ethylthiooxamate, 4.25 g of 2-aminoacetophenone hydrochloride and 3.69 g of sodium acetate was dissolved in 20 mL of acetic acid and heated under reflux for 3 hr. The reaction mixture was allowed to cool to room temperature and the acetic acid removed by evaporation under reduced pressure. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide.Primary amine.Thiocarbonyl | Ester | null | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | null | null | null | CC(=O)[O-].CCNC(=O)C([O-])=S.NCC(=O)c1ccccc1>>CCOC(=O)c1nc(-c2ccccc2)c[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1e5b9dea2807444dbd3f6f54b251d447 | CCOC(=O)c1nc(-c2ccccc2)c[nH]1>>OCc1nc(-c2ccccc2)c[nH]1 | C(C)OC(=O)C=1NC=C(N1)C1=CC=CC=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OCC=1NC=C(N1)C1=CC=CC=C1 | CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][nH:13]1>>[OH:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][nH:13]1 | CCOC(=O)c1nc(-c2ccccc2)c[nH]1 | OCc1nc(-c2ccccc2)c[nH]1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2c[nH]cn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1 | 90.3 | [{"value": 90.3, "product": "OCC=1NC=C(N1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2.75 g ethyl-4-phenylimidazole-2-carboxylate in 20 mL tetrahydrofuran was added a suspension of 0.5 g lithium aluminum hydride in 30 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature overnight, poured into 100 mL of ice water and extracted with 2 x I00 mL of ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]cn1.c1ccccc1 | HO- | O1CCCC1 | null | 8 | CCOC(=O)c1nc(-c2ccccc2)c[nH]1>O1CCCC1>OCc1nc(-c2ccccc2)c[nH]1 |
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