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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dcc5f15a2f3f46578b2a4b1538a1f0d4 | Fc1ccc(Cc2ccc(F)cc2)cc1.O=S(=O)(O)O>>O=C(c1ccc(F)cc1)c1ccc(F)cc1 | C1=CC(=CC=C1CC2=CC=C(C=C2)F)F.S(O)(O)(=O)=O>>FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1 | [CH2:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.O=S(=O)(O)[OH:1]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | Fc1ccc(Cc2ccc(F)cc2)cc1.O=S(=O)(O)O | O=C(c1ccc(F)cc1)c1ccc(F)cc1 | null | O=[Mn]=O | O | Heteroatom Alkylation and Arylation | OtherReaction | 7a0b8463d98f4c7b922b16e60aaf09698e9f90cf246a26e079db9b5cbdeab585 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C(c1ccccc1)c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[c:2]:[c:3](-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:4](-[c:3](:[c:2]):[c:8])-[c:5](:[c:6]):[c:7] | 54 | [{"value": 54.0, "product": "FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 2 is used except that the 4,4'-difluorodiphenylmethane, water, and sulfuric acid are first mixed, then heated before the MnO2 is added. The yield is 54% 4,4'-difluorobenzophenone that is 95% pure.
Conditions: See reaction.notes.procedure_details.
Workup: are first mixed; is added | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | O=[Mn]=O.O | null | null | Fc1ccc(Cc2ccc(F)cc2)cc1.O=S(=O)(O)O>O=[Mn]=O.O>O=C(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-96051f14cb3b4b208319a04c297eb60a | COC(O)C(F)(F)F.c1c[nH]c(Cc2ccc[nH]2)c1>>FC(F)(F)C(c1ccc[nH]1)c1ccc[nH]1 | C1=CNC(=C1)CC2=CC=CN2.N1C=CC=C1.COC(C(F)(F)F)O.Cl>>N1C(=CC=C1)C(C(F)(F)F)C=1NC=CC1 | CO[CH:5](O)[C:2]([F:1])([F:3])[F:4].C([c:6]1[cH:7][cH:8][cH:9][nH:10]1)[c:11]1[cH:12][cH:13][cH:14][nH:15]1>>[F:1][C:2]([F:3])([F:4])[CH:5]([c:6]1[cH:7][cH:8][cH:9][nH:10]1)[c:11]1[cH:12][cH:13][cH:14][nH:15]1 | COC(O)C(F)(F)F.c1c[nH]c(Cc2ccc[nH]2)c1 | FC(F)(F)C(c1ccc[nH]1)c1ccc[nH]1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 26bb76746e821a862b1e2d546d22a30a9fdcdd23dd039944c7d038242961e716 | d57bc9a8102fea3a5aa53b38c291195cce6195e07ef2332b8d2a4f85929ab48b | c1c[nH]c(Cc2ccc[nH]2)c1 | C(-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1)-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1.C-O-[CH;D3;+0:11](-O)-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]>>[F;D1;H0:13]-[C:12](-[F;D1;H0:14])(-[F;D1;H0:15])-[CH;D3;+0:11](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1)-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9]:[c:1... | 80 | [{"value": 80.0, "product": "N1C(=CC=C1)C(C(F)(F)F)C=1NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pyrrole (150 mmol) and trifluoroacetaldehyde methyl hemiacetal (75 mmol) in tetrahydrofuran are heated at reflux with catalytic amounts of hydrochloric acid for 2 hours under an inert atmosphere. GC analysis of the reaction mixture indicated the presence of the desired dipyrromethane in greater than 80% yield. Neutrali... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | null | c1cc[nH]c1.c1cc[nH]c1 | c1cc[nH]c1.c1cc[nH]c1 | c1cc[nH]c1.c1cc[nH]c1 | HO- | O1CCCC1 | null | null | COC(O)C(F)(F)F.c1c[nH]c(Cc2ccc[nH]2)c1>O1CCCC1>FC(F)(F)C(c1ccc[nH]1)c1ccc[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68a3f07b1c044ef79787604ed33c105d | C1=Cc2ccccc2C1.Cc1cc(C)c([Si](Cl)(Cl)c2c(C)cc(C)cc2C)c(C)c1.[Li][CH2]CCC>>Cc1cc(C)c([Si](c2c(C)cc(C)cc2C)(C2C=Cc3ccccc32)C2C=Cc3ccccc32)c(C)c1 | C1(=C(C(=CC(=C1)C)C)[Si](Cl)(Cl)C1=C(C=C(C=C1C)C)C)C.C1C=CC2=CC=CC=C12.C(CCC)[Li]>>C1(=C(C(=CC(=C1)C)C)[Si](C1C=CC2=CC=CC=C12)(C1C=CC2=CC=CC=C12)C1=C(C=C(C=C1C)C)C)C | [CH2:26]1[CH:27]=[CH:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21.Cl[Si:7](Cl)([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:37][c:35]1[CH3:36])[c:8]1[c:9]([CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]1[CH3:16].[Li][CH2:19][CH2:18][CH2:17][CH3:25]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([Si:7]([c:8]2[c:9]([CH3:10])[cH:... | C1=Cc2ccccc2C1.Cc1cc(C)c([Si](Cl)(Cl)c2c(C)cc(C)cc2C)c(C)c1.[Li][CH2]CCC | Cc1cc(C)c([Si](c2c(C)cc(C)cc2C)(C2C=Cc3ccccc32)C2C=Cc3ccccc32)c(C)c1 | null | null | C1CCOC1 | Functional Group Addition | OtherReaction | f5ba5559104034d0f598342b2bcfc145616a870a9c5fd32040e01d9d349081e9 | 56324ad3df7b9487aaee7bd464929a93e4e28f6516884ae0bd489c1176bd68e8 | C1=CC([Si](c2ccccc2)(c2ccccc2)C2C=Cc3ccccc32)c2ccccc21 | Cl-[Si;H0;D4;+0:1](-Cl)(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[CH3;D1;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[Li].[c:12]:[c:13]1:[c:14]-[C:15]=[C:16]-[CH2;D2;+0:17]-1>>[c:6]:[c:5](-[Si;H0;D4;+0:1](-[CH;D3;+0:9]1-[CH;D2;+0:10]=[CH;D2;+0:11]-[c:18](:[c:19]):[c;H0;D3;+0:8]-1:[c:20]:[c:21])(-[CH;D3;+0:17]1-[... | null | [] | null | null | null | null | 7 g of indene in 50 cm3of THF were reacted with 24 cm3 of butyllithium (2.5-molar in hexane) at 0° C. under inert conditions. The mixture was heated to room temperature, added dropwise to a solution of 10 g of dimesityldichlorosilane in 40 cm3 of THF, and the mixture was refluxed for 4 hours. Decomposition of the batch... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group.Alkyl lithium | Silyl protective group | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.C1=Cc2ccccc2C1 | c1ccccc1.c1ccccc1.C1=Cc2ccccc2C1.C1=Cc2ccccc2C1 | HCl.Li | C1CCOC1 | null | null | C1=Cc2ccccc2C1.Cc1cc(C)c([Si](Cl)(Cl)c2c(C)cc(C)cc2C)c(C)c1.[Li][CH2]CCC>C1CCOC1>Cc1cc(C)c([Si](c2c(C)cc(C)cc2C)(C2C=Cc3ccccc32)C2C=Cc3ccccc32)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d4e2b55500174bc5b7869b5b5174c913 | C#C[Si](C)(C)C.COc1ccc(C2=CC(=O)CCC2)cc1OC1CCCC1>>COc1ccc(C2(C#C[Si](C)(C)C)CCCC(=O)C2)cc1OC1CCCC1 | C(CCC)[Li].C[Si](C)(C)C#C.[Cl-].C[Al+]C.C1(CCCC1)OC=1C=C(C=CC1OC)C1=CC(CCC1)=O.[C-]#[C-].[Al+3].[C-]#[C-].[C-]#[C-].[Al+3].Cl.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[H-].C(C(C)C)[Al+]CC(C)C>>C1(CCCC1)OC=1C=C(C=CC1OC)C1(CC(CCC1)=O)C#C[Si](C)(C)C | [CH:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[CH:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14]2)[cH:20][c:21]1[O:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([C:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][CH2:16][C:1... | C#C[Si](C)(C)C.COc1ccc(C2=CC(=O)CCC2)cc1OC1CCCC1 | COc1ccc(C2(C#C[Si](C)(C)C)CCCC(=O)C2)cc1OC1CCCC1 | null | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2] | CCOCC | C-C Coupling | OtherReaction | ddd89ebc1749bc44b47a2b082f77fd8d8e29610c5cb4f10c5a05976ac8c3fe51 | 496ecbb5613a35d3e186da35e0b9e585797614c00ffb214bf902564b30c30743 | O=C1CCCC(c2cccc(OC3CCCC3)c2)C1 | [C;D1;H3:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]#[CH;D1;+0:6].[O;D1;H0:7]=[C:8]1-[C:9]-[C:10]-[C:11]-[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])=[CH;D2;+0:16]-1>>[C;D1;H3:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]#[C;H0;D2;+0:6]-[C;H0;D4;+0:12]1(-[c:13](:[c:14]):[c:15])-[C:11]-[C:10]-[C:9]-[C:8](=[O;D1;H0:7])-[CH2;... | null | [] | -10 | CELSIUS | 1.5 | HOUR | n-Butyllithium (2.45M in hexanes, 5.7 mL, 13.96 mmol) was added dropwise over 5 min to a solution of trimethylsilylacetylene (1.97 mL, 13.96 mmol) dissolved in dry ether (30 mL) at -45° C. under an argon atmosphere. After 1.5 h, this solution was cannulated into a solution of dimethylaluminum chloride (1.0M in hexanes,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Ketone.Alkyne | C1=CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1.C1CCCC1 | null | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].CCOCC | -10 | 1.5 | C#C[Si](C)(C)C.COc1ccc(C2=CC(=O)CCC2)cc1OC1CCCC1>C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].CCOCC>COc1ccc(C2(C#C[Si](C)(C)C)CCCC(=O)C2)cc1OC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a765bb3f88ef412dab87283ec66e35db | COc1ccc(C2(C#C[Si](C)(C)C)CCCC(=O)C2)cc1OC1CCCC1>>C#CC1(c2ccc(OC)c(OC3CCCC3)c2)CCCC(=O)C1 | [F-].[K+].C1(CCCC1)OC=1C=C(C=CC1OC)C1(CC(CCC1)=O)C#C[Si](C)(C)C.O>>C1(CCCC1)OC=1C=C(C=CC1OC)C1(CC(CCC1)=O)C#C | C[Si](C)(C)[C:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([O:8][CH3:9])[c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17]2)[CH2:18][CH2:19][CH2:20][C:21](=[O:22])[CH2:23]1>>[CH:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([O:8][CH3:9])[c:10]([O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17]2)[CH2:18][CH2:19][CH2... | COc1ccc(C2(C#C[Si](C)(C)C)CCCC(=O)C2)cc1OC1CCCC1 | C#CC1(c2ccc(OC)c(OC3CCCC3)c2)CCCC(=O)C1 | null | null | CN(C=O)C | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | O=C1CCCC(c2cccc(OC3CCCC3)c2)C1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[C:3]>>[C:3]-[C:2]#[CH;D1;+0:1] | null | [] | null | null | 18 | HOUR | A mixture of potassium fluoride (900 mg, 15.6 mmol) and 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one (0.3 g, 0.78 mmol) were stirred in dry N,N-dimethylformamide (3 mL) under an argon atmosphere. After 18 h, the solvent was removed in vacuo, the residue was partitioned between water and ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.C1CCCC1.C1CCCCC1 | Other | CN(C=O)C | null | 18 | COc1ccc(C2(C#C[Si](C)(C)C)CCCC(=O)C2)cc1OC1CCCC1>CN(C=O)C>C#CC1(c2ccc(OC)c(OC3CCCC3)c2)CCCC(=O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-269b34579b6543ad8b25187fc9fff0bb | CC(C)(C)C=NC1CCNC1.O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O>>NC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C1 | C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C(=O)O.CC(C=NC1CNCC1)(C)C.Cl>>Cl.NC1CN(CC1)C1=C(C=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)F | CC(C)(C)C=[N:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:26]1.F[c:7]1[c:8]([F:9])[cH:10][c:11]2[c:12](=[O:13])[c:14]([C:15](=[O:16])[OH:17])[cH:18][n:19]([CH:20]3[CH2:21][CH2:22]3)[c:23]2[c:24]1[F:25]>>[NH2:2][CH:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8]([F:9])[cH:10][c:11]3[c:12](=[O:13])[c:14]([C:15](=[O:16])[OH:17])[cH:18][n:19]([CH... | CC(C)(C)C=NC1CCNC1.O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O | NC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 710de7c0f65dd5c2121f3b57da0b26f7168348cc6c1e92dfd93051671f74f524 | f353eb8fdf386bd5566d538a686db0446740ceebfed68cde5410916b51190f54 | O=c1ccn(C2CC2)c2cc(N3CCCC3)ccc12 | C-C(-C)(-C)-C=[N;H0;D2;+0:1]-[C:2]1-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.F-[c;H0;D3;+0:7]1:[c:8](-[F;D1;H0:9]):[c:10](:[c:11]:[c:12]:[c:13]:1-[F;D1;H0:14]):[#7;a:15](-[C:16]):[c:17]>>[C:16]-[#7;a:15](:[c:17]):[c:10]1:[c:11]:[c:12]:[c:13](-[F;D1;H0:14]):[c;H0;D3;+0:7](-[N;H0;D3;+0:4]2-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:6]-[C:5]... | null | [] | null | null | null | null | If, for example, 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid is reacted with 3-(2,2-dimethylpropylideneamino)-pyrrolidine and the reaction product is treated with hydrochloric acid, 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Substituted imine.Secondary amine | Primary amine.Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CC(C)(C)C=NC1CCNC1.O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O>>NC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9c49b6d642f487a8b46731f4e1e7af0 | N[C@H]1CCNC1.O=C(O)c1cn(C2CC2)c2c(Cl)c(F)c(F)cc2c1=O.O=C(O)c1cn(C2CC2)c2c(Cl)c(N3CC[C@H](N=Cc4cccc([N+](=O)[O-])c4)C3)c(F)cc2c1=O>>Cl.N[C@H]1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1 | ClC=1C(=C(C=C2C(C(=CN(C12)C1CC1)C(=O)O)=O)F)N1C[C@H](CC1)N=CC1=CC(=CC=C1)[N+](=O)[O-].[N+](=O)([O-])C=1C=C(C=O)C=CC1.N[C@@H]1CNCC1.ClC=1C(=C(C=C2C(C(=CN(C12)C1CC1)C(=O)O)=O)F)F>>Cl.N[C@@H]1CN(CC1)C1=C(C=C2C(C(=CN(C2=C1Cl)C1CC1)C(=O)O)=O)F | [NH2:2][C@H:3]1[CH2:4][CH2:5][NH:6][CH2:26]1.F[c:7]1[c:8]([F:9])[cH:10][c:11]2[c:12](=[O:13])[c:14]([C:15](=[O:16])[OH:17])[cH:18][n:19]([CH:20]3[CH2:21][CH2:22]3)[c:23]2[c:24]1[Cl:25].O=C(O)c1cn(C2CC2)c2c([Cl:1])c(N3CC[C@H](N=Cc4cccc([N+](=O)[O-])c4)C3)c(F)cc2c1=O>>[ClH:1].[NH2:2][C@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[c:8... | N[C@H]1CCNC1.O=C(O)c1cn(C2CC2)c2c(Cl)c(F)c(F)cc2c1=O.O=C(O)c1cn(C2CC2)c2c(Cl)c(N3CC[C@H](N=Cc4cccc([N+](=O)[O-])c4)C3)c(F)cc2c1=O | Cl.N[C@H]1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1 | null | null | null | Functional Group Interconversion | OtherReaction | 78881d4233cf847b87824634d66c42a6f7871c5d6d250c7f037843fc9638c5c1 | 07252a64ae90f2baee4c93a74a5ef061c0a9357a49917c41f677ac91017b1b84 | O=c1ccn(C2CC2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[Cl;D1;H0:3]):[c:4](:[c:5]:[c:6]:[c:7]:1-[F;D1;H0:8]):[#7;a:9](-[C:10]):[c:11].F-c1:c:c2:c(=O):c(-C(-O)=O):c:n(-C3-C-C-3):c:2:c(-[Cl;H0;D1;+0:12]):c:1-N1-C-C-[C@H](-N=C-c2:c:c:c:c(-[N+](=O)-[O-]):c:2)-C-1.[C:13]1-[C:14]-[C:15]-[C:16]-[NH;D2;+0:17]-1>>[C:10]-[#7;a:9](:[c:11]):[c:4]1:[c:5]:[c:6]:... | null | [] | null | null | null | null | If, for example, the reaction mixture of 3-nitrobenzaldehyde and (S)-3-aminopyrrolidine is reacted with 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in a one-pot reaction, the course of the reaction via the intermediately formed 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Substituted imine.Nitro group.Secondary amine.Tertiary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1.C1CC1.c1ccc2ncccc2c1.C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | N[C@H]1CCNC1.O=C(O)c1cn(C2CC2)c2c(Cl)c(F)c(F)cc2c1=O.O=C(O)c1cn(C2CC2)c2c(Cl)c(N3CC[C@H](N=Cc4cccc([N+](=O)[O-])c4)C3)c(F)cc2c1=O>>Cl.N[C@H]1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0f745d78785401496f0649633321e35 | CC(C)(C)C=O.NC1CCNC1>>CC(C)(C)C=NC1CCNC1 | NC1CNCC1.C(C(C)(C)C)=O>>CC(C=NC1CNCC1)(C)C | O=[CH:5][C:2]([CH3:1])([CH3:3])[CH3:4].[NH2:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]=[N:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11]1 | CC(C)(C)C=O.NC1CCNC1 | CC(C)(C)C=NC1CCNC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C1CCNC1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[N;H0;D2;+0:9]=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5])-[C:10] | 74 | [{"value": 74.0, "product": "CC(C=NC1CNCC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 34.5 g (0.4 mol) of 3-aminopyrrolidine are initially introduced into 100 ml of toluene, and 34.5 g (0.3 mol) of 75% strength pivalaldehyde (preparation from Riedel-de-Haen) in 100 ml of toluene are added dropwise at 20° C., while cooling in a water bath. The mixture is subsequently stirred at room temperature for 2 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | C1CCNC1 | HO- | C1(=CC=CC=C1)C | null | 2 | CC(C)(C)C=O.NC1CCNC1>C1(=CC=CC=C1)C>CC(C)(C)C=NC1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8341607dd237492f8c1a68b89ed51a7c | CC(C)(C)C=O.NC1CCNC1>>CC(C)(C)C=NC1CCNC1 | C(C(C)(C)C)=O.NC1CNCC1>>CC(C=NC1CNCC1)(C)C | O=[CH:5][C:2]([CH3:1])([CH3:3])[CH3:4].[NH2:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]=[N:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11]1 | CC(C)(C)C=O.NC1CCNC1 | CC(C)(C)C=NC1CCNC1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C1CCNC1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[N;H0;D2;+0:9]=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5])-[C:10] | null | [] | null | null | 1 | HOUR | 12.1 g (0.1 mol) of 71% strength pivalaldehyde, initially introduced into the reaction vessel and 8.6 g (0.1 mol) of 3-aminopyrrolidine are added dropwise at 20° C. to 30° C., while cooling in a water bath. The mixture is subsequently stirred at room temperature for 1 hour and is then distilled. Yield: 13.5 g (85% of t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | C1CCNC1 | HO- | null | null | 1 | CC(C)(C)C=O.NC1CCNC1>>CC(C)(C)C=NC1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-260f7eb07f4b4633acca339360195729 | C.c1ccc(CNC2CCN(Cc3ccccc3)C2)cc1>>CC(C)(C)C=NC1CCNC1 | C(C1=CC=CC=C1)N1CC(CC1)NCC1=CC=CC=C1.C>>CC(C=NC1CNCC1)(C)C | [CH4:1].c1ccc(C[N:10]2[CH2:9][CH2:8][CH:7]([NH:6][CH2:5][c:2]3[cH:3]ccc[cH:4]3)[CH2:11]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]=[N:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11]1 | C.c1ccc(CNC2CCN(Cc3ccccc3)C2)cc1 | CC(C)(C)C=NC1CCNC1 | null | [Pd] | CO | C-C Coupling | OtherReaction | 008045eaa7bd2f16a9005ebf9e735a9e3e3fc5bf26dd5ea812e145f5407c5bbc | d7a8bf426327cb09b51ad349220aebac5ec6b853324d0e830c43b4d7f3b2056c | C1CCNC1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:6]2:[cH;D2;+0:7]:c:c:c:[cH;D2;+0:8]:2)-[C:9]-[C:10]-1)-c1:c:c:c:c:c:1.[CH4;D0;+0:11]>>[CH3;D1;+0:11]-[C;H0;D4;+0:6](-[CH3;D1;+0:7])(-[CH3;D1;+0:8])-[CH;D2;+0:5]=[N;H0;D2;+0:4]-[C:3]1-[C:2]-[NH;D2;+0:1]-[C:10]-[C:9]-1 | 58 | [{"value": 58.0, "product": "CC(C=NC1CNCC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 36.8 g (0.138 mol) of 1-benzyl-3-benzylaminopyrrolidine are hydrogenated in 160 ml of methanol over 5 g of 5% strength palladium on active charcoal at 130° C. under a hydrogen pressure of 100 bar for 10 hours. The catalyst is filtered off and 16.6 g (0.138 mol ) of 71% strength pivalaldehyde are added to the filtrate, ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Tertiary amine | Substituted imine.Secondary amine | c1ccccc1.C1CC[NH]C1.c1ccccc1 | C1CCNC1 | C1CCNC1 | Other | [Pd].CO | null | null | C.c1ccc(CNC2CCN(Cc3ccccc3)C2)cc1>[Pd].CO>CC(C)(C)C=NC1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2630f868c1ae4906a64306843a19fa7f | CC(C)(C)C=O.NCC1CCNC1>>CC(C)(C)C=NCC1CCNC1 | NCC1CNCC1.C(C(C)(C)C)=O>>CC(C=NCC1CNCC1)(C)C | O=[CH:5][C:2]([CH3:1])([CH3:3])[CH3:4].[NH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]=[N:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:12]1 | CC(C)(C)C=O.NCC1CCNC1 | CC(C)(C)C=NCC1CCNC1 | null | null | CO | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C1CCNC1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[N;H0;D2;+0:8]=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5] | null | [] | null | null | 1 | HOUR | 2.0 g (20 mmol) of 3-aminomethyl-pyrrolidine are initially introduced into 10 ml of methanol, and 1.8 g (22 mmol) of 97% strength pivalaldehyde are added dropwise at room temperature, after which the internal temperature rises to 30° C. The mixture is subsequently stirred for 1 hour and then concentrated, and the resid... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | C1CCNC1 | HO- | CO | null | 1 | CC(C)(C)C=O.NCC1CCNC1>CO>CC(C)(C)C=NCC1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13330458b3c94465aa5dc67623f8b399 | CS(=O)(=O)Cl.N.O=C(c1ccccc1)N1CC=CC1>>CS[C@@H]1CN(C(=O)c2ccccc2)C[C@H]1N | C([O-])([O-])=O.[Na+].[Na+].C(C1=CC=CC=C1)(=O)N1CC=CC1.CS(=O)(=O)Cl.N>>C(C1=CC=CC=C1)(=O)N1C[C@H]([C@@H](C1)SC)N | O=[S:2](=O)(Cl)[CH3:1].[NH3:16].[CH:3]1=[CH:15][CH2:14][N:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:4]1>>[CH3:1][S:2][C@@H:3]1[CH2:4][N:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][C@H:15]1[NH2:16] | CS(=O)(=O)Cl.N.O=C(c1ccccc1)N1CC=CC1 | CS[C@@H]1CN(C(=O)c2ccccc2)C[C@H]1N | null | null | C(Cl)Cl.O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 628efffe4c4c45177dcbdedc5f5da0b6ed938771e8cd394fe86b6a42018453f5 | c76f65538900d68fb447211fd1a77e66f67bd4754b2f351d4c3fdeffd1b6f063 | O=C(c1ccccc1)N1CCCC1 | Cl-[S;H0;D4;+0:1](=O)(=O)-[C;D1;H3:2].[NH3;D0;+0:3].[O;D1;H0:4]=[C:5]-[#7:6]1-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-1>>[C;D1;H3:2]-[S;H0;D2;+0:1]-[C@@H;D3;+0:9]1-[C:10]-[#7:6](-[C:5]=[O;D1;H0:4])-[C:7]-[C@H;D3;+0:8]-1-[NH2;D1;+0:3] | null | [] | null | null | 16 | HOUR | 41.5 g (0.24 mol) of 1-benzoyl-2,5-dihydropyrrole are initially introduced into 240 ml of methylene chloride, and 24.8 g (0.3 mol) of methanesulphonyl chloride are added dropwise at 0° C. The mixture is subsequently stirred at room temperature for 16 hours, the solvent is then stripped off under 8 mbar and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Primary amine.Monosulfide | C1=CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HCl | C(Cl)Cl.O.O1CCCC1 | null | 16 | CS(=O)(=O)Cl.N.O=C(c1ccccc1)N1CC=CC1>C(Cl)Cl.O.O1CCCC1>CS[C@@H]1CN(C(=O)c2ccccc2)C[C@H]1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e8dac3a3e84b49d4bd31f050b2729740 | CC(C)(C)C=O.CS[C@@H]1CNC[C@H]1N>>CS[C@@H]1CNC[C@H]1N=CC(C)(C)C | N[C@@H]1CNC[C@H]1SC.C(C(C)(C)C)=O>>CC(C=N[C@@H]1CNC[C@H]1SC)(C)C | O=[CH:9][C:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][S:2][C@@H:3]1[CH2:4][NH:5][CH2:6][C@H:7]1[NH2:8]>>[CH3:1][S:2][C@@H:3]1[CH2:4][NH:5][CH2:6][C@H:7]1[N:8]=[CH:9][C:10]([CH3:11])([CH3:12])[CH3:13] | CC(C)(C)C=O.CS[C@@H]1CNC[C@H]1N | CS[C@@H]1CNC[C@H]1N=CC(C)(C)C | null | null | CO | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C1CCNC1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[N;H0;D2;+0:9]=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5])-[C:10] | null | [] | null | null | 30 | MINUTE | 1.32 g (10 mmol) of trans-3-amino-4-methylthio-pyrrolidine are initially introduced into 5 ml of methanol, and 1.23 ml (11 mmol) of 97% strength pivalaldehyde are added dropwise, after which the temperature rises from 25° to 36° C. The mixture is subsequently stirred for a further 30 minutes, without cooling, the batch... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | C1CCNC1 | HO- | CO | null | 0.5 | CC(C)(C)C=O.CS[C@@H]1CNC[C@H]1N>CO>CS[C@@H]1CNC[C@H]1N=CC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-182cab8e991e46b5ad9d638c603333a5 | CC(C)(C)C=O.NC1CCNC1.O=C(O)C1=CN(C2CC2)c2c(cc(F)c(F)c2Cl)C1>>NC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1 | C(C(C)(C)C)=O.NC1CNCC1.ClC=1C(=C(C=C2CC(=CN(C12)C1CC1)C(=O)O)F)F.N12CCN(CC1)CC2.CC(C=NC1CNCC1)(C)C>>NC1CN(CC1)C1=C(C=C2C(C(=CN(C2=C1Cl)C1CC1)C(=O)O)=O)F | CC(C)(C)C=[O:12].[NH2:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:25]1.F[c:6]1[c:7]([F:8])[cH:9][c:10]2[c:22]([c:23]1[Cl:24])[N:18]([CH:19]1[CH2:20][CH2:21]1)[CH:17]=[C:13]([C:14](=[O:15])[OH:16])[CH2:11]2>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[c:7]([F:8])[cH:9][c:10]3[c:11](=[O:12])[c:13]([C:14](=[O:15])[OH:16])[cH:17][n:18]... | CC(C)(C)C=O.NC1CCNC1.O=C(O)C1=CN(C2CC2)c2c(cc(F)c(F)c2Cl)C1 | NC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1 | null | null | C(C)#N.CN(C=O)C | Protection | OtherReaction | 52e09cc305f93f960459b1e9edab534f38d5b3d20558176aff439762f0537811 | 92145626fd4a33c3d445ebad61a15684a0400f49184758a2a80d7bdbd8a8df7f | O=c1ccn(C2CC2)c2cc(N3CCCC3)ccc12 | C-C(-C)(-C)-C=[O;H0;D1;+0:1].F-[c;H0;D3;+0:2]1:[c:3](-[Cl;D1;H0:4]):[c:5]2:[c:6](:[c:7]:[c:8]:1-[F;D1;H0:9])-[CH2;D2;+0:10]-[C;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[O;D1;H1:14])=[CH;D2;+0:15]-[N;H0;D3;+0:16]-2-[C:17]1-[C:18]-[C:19]-1.[C:20]1-[C:21]-[C:22]-[C:23]-[NH;D2;+0:24]-1>>[Cl;D1;H0:4]-[c:3]1:[c:5]2:[c:6](:[c:7]:[... | null | [] | null | null | 1 | HOUR | 0.95 g (11 mmol) of pivalaldehyde are added dropwise to a solution of 0.86 g (10 mmol) of 3-aminopyrrolidine in 10 ml of acetonitrile at room temperature in the course of 5 minutes, during which the temperature rises from 22.5° C. to 27.5° C. The mixture is subsequently stirred for 1 hour and a virtually complete conve... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Aldehyde.Secondary amine | Tertiary amine | C1CCNC1.C1=C[NH]c2ccccc2C1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HF | C(C)#N.CN(C=O)C | null | 1 | CC(C)(C)C=O.NC1CCNC1.O=C(O)C1=CN(C2CC2)c2c(cc(F)c(F)c2Cl)C1>C(C)#N.CN(C=O)C>NC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32bc0b3ba19f4eee8fecd0b31789e6b2 | CCOC(=O)CN1Cc2ccccc2C[C@H](N2C(=O)c3ccccc3C2=O)C1=O.O=C(Cl)OCc1ccccc1>>CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O | C(C)N(CC)CC.C(C1=CC=CC=C1)OC(=O)Cl.C1(C=2C(C(N1[C@@H]1C(N(CC3=C(C1)C=CC=C3)CC(=O)OCC)=O)=O)=CC=CC2)=O.C(C)O>>C1(=CC=CC=C1)COC(=O)N[C@@H]1C(N(CC2=C(C1)C=CC=C2)CC(=O)OCC)=O | O=C1c2ccccc2C(=O)[N:17]1[C@H:16]1[CH2:15][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[CH2:8][N:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:28]1=[O:29].Cl[C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]... | CCOC(=O)CN1Cc2ccccc2C[C@H](N2C(=O)c3ccccc3C2=O)C1=O.O=C(Cl)OCc1ccccc1 | CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC.O.NN | Protection | OtherReaction | fe3102b6b408f3d3825eb2b8e397463241cc48fe0961b1edbc9ae90e981158d6 | 1040b538a38b728279e7919c87da3a9c1d00e9f692e311a76ca8b5e574dd287d | O=C(N[C@H]1Cc2ccccc2CNC1=O)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O=C1-[N;H0;D3;+0:5](-[C:6](-[C:7])-[C:8](=[O;D1;H0:9])-[#7:10](-[C:11]-[C:12](-[#8:13])=[O;D1;H0:14])-[C:15])-C(=O)-c2:c:c:c:c:c:2-1>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]-[#7:10](-[C:15])-[C:8](=[O;D1;H0:9])-[C:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:7... | null | [] | 0 | CELSIUS | 2 | HOUR | A solution of (S)-1,3,4,5-tetrahydro-4-phthalimido-3-oxo-2H-2-benzazepine-2-acetic acid, ethyl ester (1.67 g., 4.26 mmol.) in 1.0M hydrazine hydrate in ethanol (9.0 ml., 9.0 mmol.) was stirred at room temperature under argon for 36 hours. The mixture was diluted with an equal volume of ethyl acetate, filtered and filtr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Substituted dicarboximide | Carbamic ester | c1ccc2c(c1)C[NH]C2 | null | c1ccc2c(c1)CCC[NH]C2.c1ccccc1 | HCl | C1(=CC=CC=C1)C.C(C)(=O)OCC.O.NN | 0 | 2 | CCOC(=O)CN1Cc2ccccc2C[C@H](N2C(=O)c3ccccc3C2=O)C1=O.O=C(Cl)OCc1ccccc1>C1(=CC=CC=C1)C.C(C)(=O)OCC.O.NN>CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d232c1adede245b1b40453d6829ded7a | CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O>>CCOC(=O)CN1Cc2ccccc2C[C@H](N)C1=O | C(Cl)(Cl)Cl.CO.C1(=CC=CC=C1)COC(=O)N[C@@H]1C(N(CC2=C(C1)C=CC=C2)CC(=O)OCC)=O.C(Cl)Cl>>N[C@@H]1C(N(CC2=C(C1)C=CC=C2)CC(=O)OCC)=O | O=C(OCc1ccccc1)[NH:17][C@H:16]1[CH2:15][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[CH2:8][N:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH2:15][C@H:16]([NH2:17])[C:18]1=[O:19] | CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O | CCOC(=O)CN1Cc2ccccc2C[C@H](N)C1=O | null | [OH-].[OH-].[Pd+2] | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C1CCc2ccccc2CN1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10])-[C:11]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6](-[C:11])-[C:4](=[O;D1;H0:5])-[C:2](-[NH2;D1;+0:1])-[C:3] | null | [] | null | null | 2 | HOUR | 20% Palladium hydroxide/carbon catalyst was added to a solution of (S)-1,3,4,5-tetrahydro-4-[[(phenylmethoxy)carbonyl]amino]-3-oxo-2H-2-benzazepine-2-acetic acid, ethyl ester (1.037 g., 2.62 mmole) in absolute ethanol (20 ml.) and the resulting suspension was stirred under a hydrogen atmosphere (balloon) for 2 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCC[NH]C2 | HO- | [OH-].[OH-].[Pd+2].C(C)O | null | 2 | CCOC(=O)CN1Cc2ccccc2C[C@H](NC(=O)OCc2ccccc2)C1=O>[OH-].[OH-].[Pd+2].C(C)O>CCOC(=O)CN1Cc2ccccc2C[C@H](N)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5a96d1b986849b2b488b84cd2b4e308 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O.CI>>COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | CI.C([O-])([O-])=O.[Cs+].[Cs+].N#N.CC(C)(OC(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)O)C.O.CO>>N#N.CC(C)(OC(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)OC)C | [OH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].I[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][... | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O.CI | COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | 5 | MINUTE | Cesium carbonate (4.28 g., 13.1 moles) was added to a mixture of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (10 g., 26.3 moles) and 20% water-methanol (60 ml.). The solution became homogeneous within 5 minutes so the solvent was stripped and the residual water removed azeotropically with ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HI | C(C)(=O)OCC | null | 0.083333 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O.CI>C(C)(=O)OCC>COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8042b51b648746afafc70ab52ab4a4bc | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1ccccc1F>>CC(C)(C)OC(=O)N[C@@H](COc1ccccc1[N+](=O)[O-])C(=O)O | [H-].[Na+].FC1=C(C=CC=C1)[N+](=O)[O-].C(Cl)Cl.CC(C)(OC(=O)N[C@@H](CO)C(=O)O)C>>CC(C)(OC(=O)N[C@@H](COC1=C(C=CC=C1)[N+](=O)[O-])C(=O)O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][OH:11])[C:21](=[O:22])[OH:23].F[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20])[C:21](... | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1ccccc1F | CC(C)(C)OC(=O)N[C@@H](COc1ccccc1[N+](=O)[O-])C(=O)O | null | null | CN(C=O)C.CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[C:10]-[C:11]-[OH;D1;+0:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]-[C:8](=[O;D1;H0:7])-[O;D1;H1:9]):[c:2]:[c:3] | null | [] | null | null | null | null | A solution of N-[(1,1-dimethylethoxy)carbonyl]-L-serine (24.3 g., 0.118 mole) in dry dimethylformamide (25 ml.) was added dropwise over a period of 1.0 hour to a cooled (0°, ice-salt bath) suspension of 60% sodium hydride (10.1 g., 0.25 mole) in dry dimethylformamide (200 ml.) and stirring was continued at 0° until the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C=O)C.CO.C(C)(=O)O | null | null | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.O=[N+]([O-])c1ccccc1F>CN(C=O)C.CO.C(C)(=O)O>CC(C)(C)OC(=O)N[C@@H](COc1ccccc1[N+](=O)[O-])C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d33b6c72571d4550bdc29dc44648e499 | CCOC(=O)CBr.O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1>>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OCc2ccccc2)CSC[C@H]1c1ccccc1 | [OH-].[K+].BrCC(=O)OCC.BrCC(=O)OCC.C1(=CC=CC=C1)[C@@H]1CSC[C@@H](C(N1)=O)NC(=O)OCC1=CC=CC=C1>>O=C1N([C@@H](CSC[C@@H]1NC(=O)OCC1=CC=CC=C1)C1=CC=CC=C1)CC(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][S:23][CH2:24][C@H:25]1[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O... | CCOC(=O)CBr.O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1 | CCOC(=O)CN1C(=O)[C@@H](NC(=O)OCc2ccccc2)CSC[C@H]1c1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)(=O)OCC.O1CCCC1.S(=O)(=O)([O-])[O-].[Mg+2] | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 448d2a9bdfd31665de19d5d708bf0615b1c0dce8080afe65ff0e19354a21937a | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#16:6]-[C:7]-[C:8](-[c:9])-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[C:13]>>[#16:6]-[C:7]-[C:8](-[c:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:11](=[O;D1;H0:12])-[C:13] | null | [] | null | null | null | null | A solution of (3R-cis)-tetrahydro-3-phenyl-6-[[(phenylmethoxy)carbonyl]amino]-1,4-thiazepine-5(4H)-one (1.16 g., 3.25 mmol) [prepared as described by Yanagisawa et al., J. Med. Chem., Vol. 30, p. 1984-1991 (1987)] in distilled tetrahydrofuran (30 ml.), under an atmosphere of argon, was cooled to 0° C. and treated with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CNCCSC1 | C1C[NH]CCSC1 | C1C[NH]CCSC1.c1ccccc1.c1ccccc1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.O1CCCC1.S(=O)(=O)([O-])[O-].[Mg+2] | null | null | CCOC(=O)CBr.O=C(N[C@H]1CSC[C@@H](c2ccccc2)NC1=O)OCc1ccccc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.O1CCCC1.S(=O)(=O)([O-])[O-].[Mg+2]>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OCc2ccccc2)CSC[C@H]1c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5d05c1fc29046a898bb31a5a6831fa6 | N[C@@H](Cc1ccccc1)C(=O)O.[Br-]>>O=C(O)[C@@H](Br)Cc1ccccc1 | N(=O)[O-].[Na+].C1(=CC=CC=C1)C.N[C@@H](CC1=CC=CC=C1)C(=O)O.[Br-].[K+]>>Br[C@H](C(=O)O)CC1=CC=CC=C1 | N[C@H:4]([C:2](=[O:1])[OH:3])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[Br-:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([Br:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.[Br-] | O=C(O)[C@@H](Br)Cc1ccccc1 | null | null | C(C)(=O)O.S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 117344ae409beae3589a30d5997369184f62edb887830bd6b795e8dfdf82920d | 9544d3c5449a12cdcbad58c02e82937c94837ec7c67e3baf5ab21c8ae3b17e42 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | 1 | HOUR | A solution of L-phenylalanine (30.0 g., 0.175 mole) and potassium bromide (73.5 g., 0.618 mole) in 2.5N sulfuric acid (365 ml.) was cooled down to 0° (ice-salt bath) and treated portionwise with sodium nitrite (19.3 g., 0.28 mole) over a period of 1.0 hour. Stirring was continued for 1.0 hour at 0° and at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary halide | null | null | c1ccccc1 | Other | C(C)(=O)O.S(O)(O)(=O)=O | null | 1 | N[C@@H](Cc1ccccc1)C(=O)O.[Br-]>C(C)(=O)O.S(O)(O)(=O)=O>O=C(O)[C@@H](Br)Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71de4245449c4d6b882f5e5c1262b960 | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=[N+]([O-])c1ccccc1F>>C[C@@H](Oc1ccccc1[N+](=O)[O-])[C@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)(OC(=O)N[C@@H]([C@H](O)C)C(=O)O)C.[H-].[Na+].FC1=C(C=CC=C1)[N+](=O)[O-]>>CC(C)(OC(=O)N[C@@H]([C@H](OC1=C(C=CC=C1)[N+](=O)[O-])C)C(=O)O)C | [CH3:1][C@@H:2]([OH:3])[C@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:22](=[O:23])[OH:24].F[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[CH3:1][C@@H:2]([O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12])[C@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:... | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=[N+]([O-])c1ccccc1F | C[C@@H](Oc1ccccc1[N+](=O)[O-])[C@H](NC(=O)OC(C)(C)C)C(=O)O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fc6e1b465ae75176f3fa192a660d0d622bdf538cea285b0e2b9dc00b273004b2 | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[C:8](-[OH;D1;+0:9])-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C:8](-[C;D1;H3:7])-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[c:2]:[c:3] | null | [] | 0 | CELSIUS | null | null | A solution of N-[(1,1-dimethylethoxy)carbonyl]-L-threonine (5.02 g., 22.9 mmol.) in dry dimethylformamide (10 ml.) was added dropwise over a period of 30 minutes to a cooled (0° C.) suspension of 60% sodium hydride (1.93 g., 48.25 mmol., 2.11 eq.) in dry dimethylformamide (40 ml.). The reaction was stirred at 0° C. unt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C=O)C | 0 | null | C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=[N+]([O-])c1ccccc1F>CN(C=O)C>C[C@@H](Oc1ccccc1[N+](=O)[O-])[C@H](NC(=O)OC(C)(C)C)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa2dad0a7d324e3da4abe3023c156072 | CO.N[C@@H](CCCCO)C(=O)O>>COC(=O)[C@@H](N)CCCCO | N[C@H](C(=O)O)CCCCO.Cl.CO>>Cl.N[C@H](C(=O)OC)CCCCO | [CH3:1][OH:2].O[C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11] | CO.N[C@@H](CCCCO)C(=O)O | COC(=O)[C@@H](N)CCCCO | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[N;D1;H2:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C:4]-[C:3](-[N;D1;H2:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 2.5 | HOUR | A slurry of (S)-2-amino-6-hydroxyhexanoic acid (2.42 g., 16.4 mmole) in dry methanol (60 ml.) was treated with gaseous hydrogen chloride until the mixture began to reflux. The homogeneous solution was then stirred at room temperature for 2.5 hours. The solvent was stripped and the residue azeotroped three times with to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | null | HO- | null | null | 2.5 | CO.N[C@@H](CCCCO)C(=O)O>>COC(=O)[C@@H](N)CCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32b402f60fe74c78b310c537e44ff646 | CCOC(=O)CN.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>>CCCC[C@@H](C(=O)NCC(=O)OCC)N1C(=O)c2ccccc2C1=O | Cl.NCC(=O)OCC.CN1CCOCC1.C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O.OC1=CC=CC=2NN=NC21>>C1(C=2C(C(N1[C@H](C(=O)NCC(=O)OCC)CCCC)=O)=CC=CC2)=O | [NH2:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH3:14].O[CH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]([C:6](O)=[O:7])[N:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][C@@H:5]([C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[O:12][CH2:13][CH3:14])[N:15]1[C:16](=[O:17])[c:18]2[cH:1... | CCOC(=O)CN.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | CCCC[C@@H](C(=O)NCC(=O)OCC)N1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C | Acylation | OtherReaction | 0417a24920227ec1bd95566b2c81b0ce9679eff3bca069621b0123bac13830c8 | a1b92777bbff0323f68374ba2bb35d2b7447e9327d1247846bdecf2f4bf4b05b | O=C1NC(=O)c2ccccc21 | O-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5](-[#7:6](-[C:7]=[O;D1;H0:8])-[C:9]=[O;D1;H0:10])-[C;H0;D3;+0:11](-O)=[O;D1;H0:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[NH2;D1;+0:18]>>[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[NH;D2;+0:18]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:5](-[C:4]-[C:3]-[C:2]-[CH3;D1;+0:1])-[#7:6](-[C... | null | [] | null | null | 5 | MINUTE | A slurry of glycine, ethyl ester, hydrochloride salt (2.718 g, 19.5 mmol.) in dimethylformamide (36 ml.) was treated with 4-methyl morpholine (2.60 ml., 2.39 g., 23.6 mmol.) and stirred at room temperature for 5 minutes. The mixture was then treated with (S)-2-phthalimido-6-hydroxyhexanoic acid (4.50 g., 16.2 mmol.) an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Primary amine | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2 | HO- | CN(C=O)C | null | 0.083333 | CCOC(=O)CN.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>CN(C=O)C>CCCC[C@@H](C(=O)NCC(=O)OCC)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-75d6830239304b61acc836550d1f3a66 | C=CC(=O)OCC.[N-]=[N+]=NC1CCc2ccccc2NC1=O>>CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21 | N(=[N+]=[N-])C1C(NC2=C(CC1)C=CC=C2)=O.C(C=C)(=O)OCC.C(C)(C)(C)O.[K]>>N(=[N+]=[N-])C1C(N(C2=C(CC1)C=CC=C2)CCC(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[NH:8]1[C:9](=[O:10])[CH:11]([N:12]=[N+:13]=[N-:14])[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[C:9](=[O:10])[CH:11]([N:12]=[N+:13]=[N-:14])[CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | C=CC(=O)OCC.[N-]=[N+]=NC1CCc2ccccc2NC1=O | CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21 | null | null | O1CCCC1.C(C)(C)(C)O.O1CCCC1 | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | ba7c4bd71d9dac9254c12d0209ebbe315a4f74699e256502917bd8de51885203 | 91e54cd6e65f2c08b5c1a8b4338c7ceefc90d4eb91eb55b2313d1887e8793e60 | O=C1CCCc2ccccc2N1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:7]-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[C:1])-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A solution of 3-azido-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one [prepared as described by Watthey et al., J. Med. Chem., 28, p. 1511-15156 (1985)] in tetrahydrofuran/tert-butanol was cooled to 0° C. and treated with ethyl acrylate and 1N tert-butanol, potassium salt/tetrahydrofuran according to the procedure of Example... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Vinyl | Ester.Tertiary amide | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)CCCC[NH]2 | null | O1CCCC1.C(C)(C)(C)O.O1CCCC1 | null | null | C=CC(=O)OCC.[N-]=[N+]=NC1CCc2ccccc2NC1=O>O1CCCC1.C(C)(C)(C)O.O1CCCC1>CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1ba75f5f74140a4b9b975cdffd4a9e5 | CC(C)(C)OC(=O)NN.CCOC(=O)CBr>>CCOC(=O)CNNC(=O)OC(C)(C)C | C(C)N(CC)CC.C(C)N(CC)CC.BrCC(=O)OCC.C(C)N(CC)CC.N(N)C(=O)OC(C)(C)C.BrCC(=O)OCC.BrCC(=O)OCC>>CC(C)(OC(=O)NNCC(=O)OCC)C | [NH2:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15] | CC(C)(C)OC(=O)NN.CCOC(=O)CBr | CCOC(=O)CNNC(=O)OC(C)(C)C | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | a10280ad95ed368c75fdf1d65f9c7b02199bd814b62740ab81803f6da82dc483 | 150ef5d6000fad15b6e5d9a7d488fe3ba905820f4205bfb36d0ee312b4df76ec | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[NH2;D1;+0:14]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[NH;D2;+0:14]-[#7:13]-[C:11](=[O;D1;H0:12])-[#8:10]-[C:7](-[C;D1;H3:6])(-[C;D1;H3:8])-[C;D1;H3:9] | null | [] | null | null | null | null | Triethylamine (13.94 ml., 0.1 mol.) was added to a solution of hydrazine carboxylic acid, 1,1-dimethylethyl ester (13.216 g., 0.1 mole) in benzene (100 ml.), followed by the addition of ethyl bromoacetate (11.09 ml., 0.1 mol.). The reaction mixture was refluxed (oil bath, 95°-100° C.) for 14 hours, after which triethyl... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide | Acylhydrazine.Ester | null | null | null | HBr | C1=CC=CC=C1 | null | null | CC(C)(C)OC(=O)NN.CCOC(=O)CBr>C1=CC=CC=C1>CCOC(=O)CNNC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8692cdf1384947d9936fad43dc8bd8f6 | CCCC[C@@H](N)C(=O)O.[Br-]>>CCCC[C@H](Br)C(=O)O | [Br-].[K+].N[C@H](CCCC)C(=O)O.N(=O)[O-].[Na+]>>Br[C@H](C(=O)O)CCCC | N[C@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:7](=[O:8])[OH:9].[Br-:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([Br:6])[C:7](=[O:8])[OH:9] | CCCC[C@@H](N)C(=O)O.[Br-] | CCCC[C@H](Br)C(=O)O | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 117344ae409beae3589a30d5997369184f62edb887830bd6b795e8dfdf82920d | 9544d3c5449a12cdcbad58c02e82937c94837ec7c67e3baf5ab21c8ae3b17e42 | null | N-[C@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[C@@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | -10 | CELSIUS | 1 | HOUR | Potassium bromide (15.9 g., 133 mmol.) was added to a stirred solution of D-norleucine (5.0 g., 38 mmol.) in 2.5N sulfuric acid (77 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (3.94 g., 57 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary halide | null | null | null | Other | S(O)(O)(=O)=O | -10 | 1 | CCCC[C@@H](N)C(=O)O.[Br-]>S(O)(O)(=O)=O>CCCC[C@H](Br)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a9fc26c3201445093ccc42bd50dbc2c | CC(C)(C)OC(=O)C1CCNN1.O=C(Cl)OCc1ccccc1>>CC(C)(C)OC(=O)C1CCN(C(=O)OCc2ccccc2)N1 | C(C1=CC=CC=C1)OC(=O)Cl.N1=CC=CC=C1.N1NC(CC1)C(=O)OC(C)(C)C>>C1(=CC=CC=C1)COC(=O)N1NC(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][NH:11][NH:22]1.Cl[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[NH:22]1 | CC(C)(C)OC(=O)C1CCNN1.O=C(Cl)OCc1ccccc1 | CC(C)(C)OC(=O)C1CCN(C(=O)OCc2ccccc2)N1 | null | null | C(C)#N.C(C)(=O)OCC | Protection | N-alkylation of secondary amines with alkyl halides | 73992b21715ecca97b52ecaee4e44c394a77dca0dfe1f68c20d7957ed17ccc9d | 5fd6250903fa66c378faf3ffa4e2360187bf8e16b5a0c6900f15dfbc5082c0be | O=C(OCc1ccccc1)N1CCCN1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[#7:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[#7:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:11]-[C:12]-1 | null | [] | 0 | CELSIUS | 3 | HOUR | A solution of 3-pyrazolidinecarboxylic acid, 1,1-dimethylethyl ester (10.935 g., 63.5 mmol.) in dry acetonitrile (90 ml.) was cooled to 0° C. (ice-salt bath) and treated with dry pyridine (11.0 ml.) followed by a solution of benzylchloroformate (12.54 g., 10.5 ml., 69.9 mmol.) in dry acetonitrile (25 ml.). The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine | Acylhydrazine | C1CNNC1 | C1CN[NH]C1 | C1CN[NH]C1.c1ccccc1 | HCl | C(C)#N.C(C)(=O)OCC | 0 | 3 | CC(C)(C)OC(=O)C1CCNN1.O=C(Cl)OCc1ccccc1>C(C)#N.C(C)(=O)OCC>CC(C)(C)OC(=O)C1CCN(C(=O)OCc2ccccc2)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8e6f6d403494c7b94171529ebac16f6 | CC(C)C[C@@H](N)C(=O)O.[Br-]>>CC(C)C[C@H](Br)C(=O)O | [Br-].[K+].N[C@H](CC(C)C)C(=O)O.N(=O)[O-].[Na+]>>Br[C@H](C(=O)O)CC(C)C | N[C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:7](=[O:8])[OH:9].[Br-:6]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([Br:6])[C:7](=[O:8])[OH:9] | CC(C)C[C@@H](N)C(=O)O.[Br-] | CC(C)C[C@H](Br)C(=O)O | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | 117344ae409beae3589a30d5997369184f62edb887830bd6b795e8dfdf82920d | 9544d3c5449a12cdcbad58c02e82937c94837ec7c67e3baf5ab21c8ae3b17e42 | null | N-[C@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[C@@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | -10 | CELSIUS | 1 | HOUR | Potassium bromide (9.5 g., 80 mmol.) was added to a stirred solution of D-leucine (3.0 g., 23 mmol.) in 2.5N sulfuric acid (47 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (2.4 g., 34 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C. After... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary halide | null | null | null | Other | S(O)(O)(=O)=O | -10 | 1 | CC(C)C[C@@H](N)C(=O)O.[Br-]>S(O)(O)(=O)=O>CC(C)C[C@H](Br)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc6e6e4b092043918a2288ce8fa820b4 | CC(=Cc1ccccc1)C(=O)O>>CC(Cc1ccccc1)C(=O)O | CC(C(=O)O)=CC1=CC=CC=C1>>CC(C(=O)O)CC1=CC=CC=C1 | [CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12] | CC(=Cc1ccccc1)C(=O)O | CC(Cc1ccccc1)C(=O)O | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | null | null | A solution of α-methyl cinnamic acid (10.0 g., 61.7 mmol.) in dry methanol (250 ml.) was treated with 10% palladium on carbon and hydrogenated (balloon used) at room temperature for 16 hours. The reaction mixture was diluted with methanol (250 ml.), filtered through a Celite pad in a millipore unit, washing the pad wel... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | [Pd].CO | null | null | CC(=Cc1ccccc1)C(=O)O>[Pd].CO>CC(Cc1ccccc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bb89d795a1f04c6a9aea5994f10b7016 | BrCc1ccccc1.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>>O=C(OCc1ccccc1)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | C([O-])([O-])=O.[Cs+].[Cs+].C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O.C(C1=CC=CC=C1)Br>>C1(C=2C(C(N1[C@H](C(=O)OCC1=CC=CC=C1)CCCCO)=O)=CC=CC2)=O | Br[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:1]=[C:2]([OH:3])[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:17]1[C:18... | BrCc1ccccc1.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | O=C(OCc1ccccc1)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(CN1C(=O)c2ccccc2C1=O)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | A slurry of cesium carbonate (3.819 g, 11.7 mmol.) and (S)-2-phthalimido-6-hydroxyhexanoic acid (6.00 g, 21.6 mmol.) in dimethylformamide (60 ml.) was treated with benzyl bromide (3.30 ml., 4.75 g., 27.7 mmol.). After stirring at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and water.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HBr | CN(C=O)C | null | 2 | BrCc1ccccc1.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>CN(C=O)C>O=C(OCc1ccccc1)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42ed6fb7dd91419caecfec4b1a99a601 | CI.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>>COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O.C([O-])([O-])=O.[Cs+].[Cs+].CI>>C1(C=2C(C(N1[C@H](C(=O)OC)CCCCO)=O)=CC=CC2)=O | I[CH3:1].[OH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21] | CI.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | O=C1NC(=O)c2ccccc21 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 196 | [{"value": 196.0, "product": "C1(C=2C(C(N1[C@H](C(=O)OC)CCCCO)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed succes... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccc2c(c1)C[NH]C2 | HI | CN(C=O)C.C(C)(=O)OCC | null | 2 | CI.O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O>CN(C=O)C.C(C)(=O)OCC>COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-610f08ba6e464144a63f27b6b8c29436 | CCOC(=O)CBr.C[C@@H]1CCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1>>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCC[C@H]1C | CC(C)(OC(=O)N[C@@H]1C(N[C@@H](CCC1)C)=O)C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].BrCC(=O)OCC>>CC(C)(OC(=O)N[C@@H]1C(N([C@@H](CCC1)C)CC(=O)OCC)=O)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20][CH2:21][C@H:22]1[CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[C:8](=[O:9])[C@@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH... | CCOC(=O)CBr.C[C@@H]1CCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1 | CCOC(=O)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCC[C@H]1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 21efda898581b4e7e1b0a01b07328527522c0c899fbfe8483d7f4fdc1f9e273c | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C1CCCCCN1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C:12]>>[C:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:10](-[C;D1;H3:11])-[C:12] | null | [] | null | null | 30 | MINUTE | A solution of (3S-cis)-hexahydro-3-[[(1,1-dimethylethoxy)carbonyl]amino]-7-methyl-2H-azepin-2-one [prepared as described in Example 64(f), 500 mg., 2.06 mmol.] in tetrahydrofuran (13 ml.) at room temperature under argon was treated dropwise with 1.0M lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 ml., 2.7 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1 | HBr | O1CCCC1 | null | 0.5 | CCOC(=O)CBr.C[C@@H]1CCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1>O1CCCC1>CCOC(=O)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCC[C@H]1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9580e3afee14b25a5c17e12c653103b | CC(C)NC(C)C.ClCCCCBr.O=C(O)C1CCCC1>>CC(C)[N-]C(C)C.O=C(O)C1(CCCCCl)CCCC1.[Li+] | BrCCCCCl.C1(CCCC1)C(=O)O.C(C)(C)NC(C)C.C(CCC)[Li]>>C(C)(C)[N-]C(C)C.[Li+].ClCCCCC1(CCCC1)C(=O)O | [CH3:1][CH:2]([CH3:3])[NH:4][CH:5]([CH3:6])[CH3:7].Br[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].[O:8]=[C:9]([OH:10])[CH:11]1[CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[N-:4][CH:5]([CH3:6])[CH3:7].[O:8]=[C:9]([OH:10])[C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][CH2:19][CH2:20]1.[Li+:21] | CC(C)NC(C)C.ClCCCCBr.O=C(O)C1CCCC1 | CC(C)[N-]C(C)C.O=C(O)C1(CCCCCl)CCCC1.[Li+] | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 77153b7242f8754879e3f0b886657cd5957a50555e81a521ab32e496bf739211 | 9ba1e0467902f373f7806da8e18ec7a85760b64f74aa649da2579d00e73d9ca4 | C1CCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])-[NH;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[O;D1;H0:11]=[C:12](-[O;D1;H1:13])-[CH;D3;+0:14]1-[C:15]-[C:16]-[C:17]-[C:18]-1>>[C;D1;H3:4]-[C:5](-[C;D1;H3:6])-[N-;H0;D2:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:14]1(-[C:12](=[O... | null | [] | -74 | CELSIUS | 15 | MINUTE | A solution of lithium diisopropylamide was prepared under nitrogen from diisopropylamine (31.0 ml., 220 mmol.) and n-butyl lithium (1.5M in hexane, 88.0 ml., 220 mmol.) in tetrahydrofuran (80 ml.), maintaining the temperature between -3° C.-1° C. After stirring 15 minutes, cyclopentanecarboxylic acid (11.4 g., 100 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | null | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | O1CCCC1 | -74 | 0.25 | CC(C)NC(C)C.ClCCCCBr.O=C(O)C1CCCC1>O1CCCC1>CC(C)[N-]C(C)C.O=C(O)C1(CCCCCl)CCCC1.[Li+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d8ba9ae803d40f58c0f4e79b8f5ba5f | CCCCC.CCOCC.CCOCC>>O=C1CCCCCC12CCCC2 | C(C)(C)(C)[Li].CCOCC.CCOCC.CCCCC>>C1CCCC12C(CCCCC2)=O | [CH3:8][CH2:12][CH2:11][CH2:10][CH3:9].C([O:1][CH2:2][CH3:3])[CH3:5].CCO[CH2:7][CH3:6]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][CH2:11][CH2:12]2 | CCCCC.CCOCC.CCOCC | O=C1CCCCCC12CCCC2 | null | null | null | Acylation | OtherReaction | 7f9c56080232237cb2af9c91b9ac11dba4e3d417835241b7fb2a95600fe5c061 | 71cd9ffc2461c2b8f2c58f8e59f7f0e3e5cc0afbee292adb82f64bbd7fde8e75 | O=C1CCCCCC12CCCC2 | C-C-O-[CH2;D2;+0:1]-[CH3;D1;+0:2].[CH3;D1;+0:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-C-[CH3;D1;+0:6].[CH3;D1;+0:7]-[C:8]-[C:9]-[C:10]-[CH3;D1;+0:11]>>[O;H0;D1;+0:5]=[C;H0;D3;+0:4]1-[CH2;D2;+0:3]-[C:12]-[CH2;D2;+0:6]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:7]-12-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-2 | null | [] | -100 | CELSIUS | null | null | t-Butyl lithium (1.7M in pentane, 20.0 ml., 34 mmol.) was slowly added to ether (38 ml.) at -20° C. as the reaction was further cooled to -100° C. in a methanol/dry ice/liquid nitrogen bath. To this -100° C. solution was added the product from part (c) (5.0 g., 16.1 mmol.) in 2:1 ether/pentane (3 ml.) over 35 minutes, ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | null | C1CCCC2(CC1)CCCC2 | C1CCCC2(CC1)CCCC2 | HO- | null | -100 | null | CCCCC.CCOCC.CCOCC>>O=C1CCCCCC12CCCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91db5ae7637043fcbd8aafa42c743728 | CC1(C)CCC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>CC1(C)CCC[C@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C(=O)N1 | C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1.O.NN.C1(C=2C(C(N1[C@H]1CCCC(NC1=O)(C)C)=O)=CC=CC2)=O.C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>>C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@H]1CCCC(NC1=O)(C)C | O=C1c2ccccc2C(=O)[N:8]1[C@H:7]1[CH2:6][CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[NH:30][C:28]1=[O:29].Cl[C: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)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][C@H:7]([NH:8][C:9]([c:10]2[cH:11][cH:... | CC1(C)CCC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | CC1(C)CCC[C@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C(=O)N1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a12cf7af8efc46e68d61b624fd0d279b6a62dfdd51fa9a2ebdb998fdcdd29be7 | 28b72e46db2638ded4e9272b0bcac45fdcf86b73ced593a7dbbac98cf9ed0efd | O=C1NCCCC[C@@H]1NC(c1ccccc1)(c1ccccc1)c1ccccc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].O=C1-[N;H0;D3;+0:11](-[C:12](-[C:13])-[C:14](=[O;D1;H0:15])-[#7:16]-[C:17])-C(=O)-c2:c:c:c:c:c:2-1>>[C:17]-[#7:16]-[C:14](=[O;D1;H0:15])-[C:12](-[NH;D2;+0:11]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10... | null | [] | null | null | 72 | HOUR | Hydrazine monohydrate (4.59 ml., 94.6 mmol.) was added to a solution of (S)-hexahydro-6-phthalimido-2,2-dimethyl-2H-azepine-7-one [prepared as described in Example 66(e), 19.98 g., 68.76 mmol.] in methanol (250 ml.) at room temperature under argon. The resulting mixture was stirred for 72 hours then filtered to remove ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Substituted dicarboximide | Secondary amine | c1ccc2c(c1)C[NH]C2 | null | C1CCCNCC1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CO | null | 72 | CC1(C)CCC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>CO>CC1(C)CCC[C@H](NC(c2ccccc2)(c2ccccc2)c2ccccc2)C(=O)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-445ecc728ecd4029a651f6f2abfe3d94 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.O=C1CCCNc2ccccc21>>O=C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | C([O-])(O)=O.[Na+].N1CCCC(C2=C1C=CC=C2)=O.C(C)N(CC)CC.[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1 | Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1.[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][NH:6][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22]... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.O=C1CCCNc2ccccc21 | O=C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 64413dd180580e9c8f2736c3a8c0c162d266e6033cf64f74e0aa763b2659218c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C1CCCN(C(=O)c2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]-[C:12]=[O;D1;H0:13]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:9](:[c:10]):[c:11]-[C:12]=[O;D1;H0:13] | null | [] | null | null | null | null | A 3.32 g portion of 2,3,4,5-tetrahydro-1H-1-benzazepin-5-one and 4.31 ml of triethylamine were dissolved in 33 ml of dichloromethane and, with stirring on an ice bath, 4.59 g of p-nitrobenzoyl chloride was added to the resulting solution. The reaction solution was stirred at room temperature for additional 60 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HCl | ClCCl | null | null | O=C(Cl)c1ccc([N+](=O)[O-])cc1.O=C1CCCNc2ccccc21>ClCCl>O=C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef4bb1c6c9b74f7baca312f5b2f73584 | O=C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21>>Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1.CN(C=O)C>>NC1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][CH2:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]32)[cH:20][cH:21]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][CH2:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]32)[cH:20][cH:21]1 | O=C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1CCCN(C(=O)c2ccccc2)c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A 19.2 g portion of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one was dissolved in a mixed solvent consisting of 200 ml of dimethylformamide and 100 ml of methyl alcohol, and 3 ml of Raney nickel was added to the resulting solution to carry out hydrogenation at normal pressure. After completion of the hydr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | Other | [Ni].CO | null | null | O=C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21>[Ni].CO>Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e6e8e890e41483eb3956e85028c6a40 | Cc1ccc(-c2ccccc2C(=O)O)cc1.Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1>>Cc1ccc(-c2cc(C(=O)N3CCCC(=O)c4ccccc43)ccc2C(=O)Nc2ccccc2)cc1 | CC1=CC=C(C=C1)C1=C(C(=O)O)C=CC=C1.NC1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1>>CC1=CC=C(C=C1)C1=C(C(=O)NC2=CC=CC=C2)C=CC(=C1)C(=O)N1CCCC(C2=C1C=CC=C2)=O | O[C:26]([c:25]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:36][cH:35]2)[cH:7][cH:8][cH:23][cH:24]1)=[O:27].[C:9](=[O:10])([N:11]1[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21)[c:32]1[cH:31][cH:30][c:29]([NH2:28])[cH:34][cH:33]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]... | Cc1ccc(-c2ccccc2C(=O)O)cc1.Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | Cc1ccc(-c2cc(C(=O)N3CCCC(=O)c4ccccc43)ccc2C(=O)Nc2ccccc2)cc1 | null | null | null | C-C Coupling | OtherReaction | a2bc7e50c766d3f3372491c10a493df5289d5bca86a323cef4d7ecb2538ff9c9 | 2bdf1de8aca0687dff29f685df308f1db97c12fed21499bf6def3aaf3ba3ab62 | O=C(Nc1ccccc1)c1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1.[C:9]-[#7:10](-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]:[c:19]:1)-[c:20]>>[C:9]-[#7:10](-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;... | null | [] | null | null | null | null | Using o-(4-methylphenyl)benzoic acid and 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one as starting materials, the procedure of Reference Example 3 was repeated to obtain 2-(4-methylphenyl)-4-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Primary amine | Secondary amide.Tertiary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2.c1ccccc1 | HO- | null | null | null | Cc1ccc(-c2ccccc2C(=O)O)cc1.Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1>>Cc1ccc(-c2cc(C(=O)N3CCCC(=O)c4ccccc43)ccc2C(=O)Nc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a89ffbbd03274d85a4403eaa7a25775f | NC(=S)Cc1ccccn1.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1>>O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4ccccn4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | C1(=CC=CC=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1.Cl.N1=C(C=CC=C1)CC(=S)N>>N1=C(C=CC=C1)CC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3 | [S:14]=[C:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1)[NH2:23].O=[C:24]1[CH2:13][CH2:12][CH2:11][N:10]([C:8]([c:7]2[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]3-[c:39]3[cH:40][cH:41][cH:42][cH:43][cH:44]3)[cH:32][cH:31]2)=[O:9])[c:30]2[c:25]1[cH:26][cH:27][cH:28][cH:29]2>>[O... | NC(=S)Cc1ccccn1.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1 | O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4ccccn4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 90831385c4296843ed9134a5e95a4102cbad965e0d393ec4e6a8a630ca15fc68 | 16c2ab1613ef9809c999e5005ffb432ea914712ab0b2c1320b2137a583f319ec | O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4ccccn4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12].[#7;a:13]:[c:14]-[C:15]-[C;H0;D3;+0:16](-[NH2;D1;+0:17])=[S;H0;D1;+0:18]>>[#7;a:13]:[c:14]-[C:15]-[c;H0;D3;+0:16]1:[n;H0;D2;+0:17]:[c;H0;D3;+0:1]2:[c;H0;D3;+0:2](:[s;H0;D2;+0:18]:1)-[C:3]-[C:4]-[#7:5](-[... | 58.3 | [{"value": 58.3, "product": "N1=C(C=CC=C1)CC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide and 370 mg of 2-pyridylthioacetamide hydrochloride, the procedure of Example 5 was repeated, and the resulting free base was recrystallized from chloroform-diethyl ether to obtain 300 mg of 4'-[[2-(2-pyridylmethyl)-5,6-dihy... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Thioamide | null | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)[NH]CCc1scnc12 | c1ccccc1.c1ccncc1.c1ccc2c(c1)[NH]CCc1scnc12.c1ccccc1.c1ccccc1 | HO- | null | null | null | NC(=S)Cc1ccccn1.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1>>O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4ccccn4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90050701c8ef48ae805729e1fea02e48 | NC(=S)Cc1cccnc1.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1>>O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4cccnc4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | C1(=CC=CC=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1.Cl.N1=CC(=CC=C1)CC(=S)N>>Cl.N1=CC(=CC=C1)CC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3 | [S:15]=[C:16]([CH2:17][c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1)[NH2:24].O=[C:25]1[CH2:14][CH2:13][CH2:12][N:11]([C:9]([c:8]2[cH:7][cH:6][c:5]([NH:4][C:3](=[O:2])[c:34]3[cH:35][cH:36][cH:37][cH:38][c:39]3-[c:40]3[cH:41][cH:42][cH:43][cH:44][cH:45]3)[cH:33][cH:32]2)=[O:10])[c:31]2[c:26]1[cH:27][cH:28][cH:29][cH:30]2>>[... | NC(=S)Cc1cccnc1.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1 | O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4cccnc4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 90831385c4296843ed9134a5e95a4102cbad965e0d393ec4e6a8a630ca15fc68 | 16c2ab1613ef9809c999e5005ffb432ea914712ab0b2c1320b2137a583f319ec | O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4cccnc4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12].[#7;a:13]:[c:14]:[c:15]-[C:16]-[C;H0;D3;+0:17](-[NH2;D1;+0:18])=[S;H0;D1;+0:19]>>[#7;a:13]:[c:14]:[c:15]-[C:16]-[c;H0;D3;+0:17]1:[n;H0;D2;+0:18]:[c;H0;D3;+0:1]2:[c;H0;D3;+0:2](:[s;H0;D2;+0:19]:1)-[C:3]-[... | 18.3 | [{"value": 18.3, "product": "Cl.N1=CC(=CC=C1)CC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide and 400 mg of 3-pyridylthioacetamide hydrochloride, the procedure of Example 5 was repeated to obtain 100 mg of 4'-[[2-(3-pyridylmethyl)-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide hydroch... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Thioamide | null | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)[NH]CCc1scnc12 | c1ccccc1.c1ccncc1.c1ccc2c(c1)[NH]CCc1scnc12.c1ccccc1.c1ccccc1 | HO- | null | null | null | NC(=S)Cc1cccnc1.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1>>O=C(Nc1ccc(C(=O)N2CCc3sc(Cc4cccnc4)nc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-026832da140844da9cfb5930520fe4e3 | CN(C)CCNC(N)=S.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1>>CN(C)CCNc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 | C1(=CC=CC=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1.Cl.CN(C)CCNC(=S)N>>CN(CCNC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[S:11].O=[C:9]1[CH2:10][CH2:12][CH2:13][N:14]([C:15](=[O:16])[c:17]2[cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]3-[c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[cH:36][cH:37]2)[c:38]2[cH:39][cH:40][cH:41][cH:42][c:43]21>>[CH3:... | CN(C)CCNC(N)=S.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1 | CN(C)CCNc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 46e4505adf07cbe530a0c849599290eef25c051af2c21072fd50c73fa13dc0c2 | 07a0b9468f27db415286267ce195abab600eca1857ac5ed441aacbc6b5c39b8e | O=C(Nc1ccc(C(=O)N2CCc3scnc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12].[C:13]-[#7:14]-[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[S;H0;D1;+0:17]>>[C:13]-[#7:14]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[c;H0;D3;+0:1]2:[c;H0;D3;+0:2](:[s;H0;D2;+0:17]:1)-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-... | 58.8 | [{"value": 58.8, "product": "CN(CCNC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro1H-1-benzazepin-1-yl)carbonyl]benzanilide and 300 mg of dimethylaminoethylthiourea hydrochloride and using ethyl alcohol as the reaction solvent, the procedure of Example 5 was repeated and the resulting residue was recrystallized from ethyl acetate-diethyl ether to... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Thiourea | null | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)[NH]CCc1scnc12 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1scnc12 | HO- | C(C)O | null | null | CN(C)CCNC(N)=S.O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1-c1ccccc1>C(C)O>CN(C)CCNc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-52eeeb285aa44f2a8df38cb2bd9296be | CC(C)(C)OC(=O)NCC(=O)O.CCN=C=NCCCN(C)C.Nc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2>>CC(C)O.NCC(=O)Nc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 | C(C)(C)(C)OC(=O)NCC(=O)O.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.Cl.C(C)N=C=NCCCN(C)C.Br.NC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3>>Cl.CC(C)O.NCC(=O)NC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3 | CC(C)(C)OC(=O)[NH:6][CH2:7][C:8]([OH:4])=[O:9].CN(CCCN=C=N[CH2:2][CH3:1])[CH3:3].[NH2:10][c:11]1[n:12][c:13]2[c:14]([s:15]1)[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([NH:25][C:26](=[O:27])[c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]3-[c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[cH:40][cH:41]1)[c:42... | CC(C)(C)OC(=O)NCC(=O)O.CCN=C=NCCCN(C)C.Nc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 | CC(C)O.NCC(=O)Nc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 | null | null | ClCCl.O.C(C)N(CC)CC | Acylation | OtherReaction | 47ded26842dab283296de32f5d8298ef874e2d0794235c9ebd8543fdbee99e79 | 82ca69076342c33c07f6f6551734c390737770207af37de3dbab41142214a909 | O=C(Nc1ccc(C(=O)N2CCc3scnc3-c3ccccc32)cc1)c1ccccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[OH;D1;+0:5].C-N(-[CH3;D1;+0:6])-C-C-C-N=C=N-[CH2;D2;+0:7]-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[C;D1;H3:8]-[CH;D3;+0:7](-[CH3;D1;+0:6])-[OH;D1;+0:5].[NH2;D1;+0:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:9]-[c:10... | 55.7 | [{"value": 55.7, "product": "Cl.CC(C)O.NCC(=O)NC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | After dissolving 176 mg of t-butoxycarbonylglycine, 205 mg of 1-hydroxybenztriazole and 0.15 ml of N-methylmorpholine in 3.5 ml of dichloromethane, 192 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to the resulting solution with stirring on an ice bath, and the mixture was warmed up to roo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Tertiary amine.Boc | Secondary amide.Secondary alcohol.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1scnc12 | HO- | ClCCl.O.C(C)N(CC)CC | null | 8 | CC(C)(C)OC(=O)NCC(=O)O.CCN=C=NCCCN(C)C.Nc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2>ClCCl.O.C(C)N(CC)CC>CC(C)O.NCC(=O)Nc1nc2c(s1)CCN(C(=O)c1ccc(NC(=O)c3ccccc3-c3ccccc3)cc1)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-63cce50ac648477a9245c0dedfc173bd | Cl>>Cl | CC=1NC2=C(CCN(C3=C2C=CC=C3)C(=O)C3=CC=C(NC(C2=C(C=CC=C2)C2=CC=CC=C2)=O)C=C3)N1.Cl.C(C)(=O)OCC>>Cl.CC=1NC2=C(CCN(C3=C2C=CC=C3)C(=O)C3=CC=C(NC(C2=C(C=CC=C2)C2=CC=CC=C2)=O)C=C3)N1 | [ClH:39]>>[ClH:39] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 4'-[(2-Methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide was dissolved in 5 ml of ethyl alcohol, the resulting solution was mixed with 0.19 ml of 4N hydrochloric acid-ethyl acetate and cooled on an ice bath and then the thus precipitated crystals were collected by filtration and wa... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58cd2e04d7a34df7b31f8a8ce82f18d5 | Cl>>Cl | CC1=CC=C(C=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=CC=C1.Cl.C(C)(=O)OCC>>Cl.CC1=CC=C(C=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=CC=C1 | [ClH:40]>>[ClH:40] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 2-(4-Methylphenyl)-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]benzanilide was dissolved in 10 ml of ethyl alcohol, the resulting solution was mixed with 0.37 ml of 4N hydrochloric acid-ethyl acetate and cooled on an ice bath and then the thus precipitated crystals were collected by filtra... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23a39ece3a4041d69c341d884e898380 | Cc1ccccc1C(=O)O.Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | CC1=C(C(=O)O)C=CC=C1.NC1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1>>CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1 | O[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH2:20][C:21](=[O:22])[c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]32)[cH:29][cH:30]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:... | Cc1ccccc1C(=O)O.Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Using o-methylbenzoic acid and 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one as starting materials, the procedure of Reference Example 3 was repeated to obtain 2-methyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | null | null | null | Cc1ccccc1C(=O)O.Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3679fbd88dec487795772a47ae39b783 | COc1cc(C(=O)O)ccc1-c1ccccc1.O=C1CCCNc2ccccc21>>COc1ccccc1-c1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | C(C(=O)Cl)(=O)Cl.CN(C=O)C.COC=1C(=CC=C(C1)C(=O)O)C1=CC=CC=C1.O=C1CCCNC2=C1C=CC=C2>>COC1=C(C2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1 | O[C:13]([c:12]1[cH:4][c:3]([O:2][CH3:1])[c:8](-[c:9]2[cH:10][cH:5][cH:6][cH:27][cH:28]2)[cH:7][cH:11]1)=[O:14].[NH:15]1[CH2:16][CH2:17][CH2:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]2[CH2:16][CH2:17][CH... | COc1cc(C(=O)O)ccc1-c1ccccc1.O=C1CCCNc2ccccc21 | COc1ccccc1-c1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 | null | null | ClCCl.O.C(C)N(CC)CC | Acylation | OtherReaction | 2699e622f477dfe56b054072967f9069c986e7f245eb9ffc00114ced8b7936a0 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1CCCN(C(=O)c2ccc(-c3ccccc3)cc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](-[c:7]2:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:2):[c:13](-[#8:14]):[cH;D2;+0:15]:1.[C:16]-[C:17]-[NH;D2;+0:18]-[c:19](:[c:20]):[c:21]-[C:22]=[O;D1;H0:23]>>[#8:14]-[c:13]1:[cH;D2;+0:15]:[cH;D2;+0:11]:[cH;D2;+0:10]:[cH;D2... | null | [] | null | null | 1 | HOUR | A 1.67 g portion of 2-methoxybiphen-4-ylcarboxylic acid was dissolved in 17 ml of dichloromethane, 0.95 ml of oxalyl chloride and a catalytically effective amount of dimethylformamide were added to the resulting solution with cooling on an ice bath and then the resulting mixture was warmed up to room temperature. When ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCCN2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | ClCCl.O.C(C)N(CC)CC | null | 1 | COc1cc(C(=O)O)ccc1-c1ccccc1.O=C1CCCNc2ccccc21>ClCCl.O.C(C)N(CC)CC>COc1ccccc1-c1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77372f28b5544f559aa1a847d124d17d | CC(C)c1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1.O>>Cc1nc2c([nH]1)-c1ccccc1N(C(=O)c1ccc(NC(=O)c3ccccc3OC(C)C)cc1)CC2 | O.[Br-].[Br-].[Br-].C1(=CC=CC=C1)[N+](C)(C)C.C1(=CC=CC=C1)[N+](C)(C)C.C1(=CC=CC=C1)[N+](C)(C)C.O1CCCC1.O=C1CCCN(C2=C1C=CC=C2)C(=O)C2=CC=C(NC(C1=C(C=CC=C1)C(C)C)=O)C=C2>>C(C)(C)OC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=CC=C1 | O=[C:5]1[CH2:4][CH2:36][CH2:35][N:13]([C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]3[CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]2)[c:12]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2.[OH2:29]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([nH:6]1)-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N:1... | CC(C)c1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1.O | Cc1nc2c([nH]1)-c1ccccc1N(C(=O)c1ccc(NC(=O)c3ccccc3OC(C)C)cc1)CC2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8da4d93b70782d4182728790bbda24f41f058aac9ebd9ad8cc383fc60ea690aa | 5e29fd0fa54248dfa34055e1e50bb98b692fd7998effad13ce7949bd843a9b7e | O=C(Nc1ccc(C(=O)N2CCc3nc[nH]c3-c3ccccc32)cc1)c1ccccc1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[#7:5](-[C:6]=[O;D1;H0:7])-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12].[C;D1;H3:13]-[CH;D3;+0:14](-[C;D1;H3:15])-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19](-[C:20](=[O;D1;H0:21])-[#7:22]-[c:23]):[c:24].[OH2;D0;+0:25]>>[C;D1;H3:13]-[CH;D3;+0:14](-[C;D1;H3:15])-[O;H0;D2;+0:25]-[c... | null | [] | null | null | 60 | MINUTE | With cooling on an ice bath, a 793 mg portion of phenyltrimethylammonium tribromide was added to 20 ml of tetrahydrofuran solution containing 1.0 g of 4'-[(5-oxo-2,3,4,5-tetrahydro1H-1-benzazepin-1-yl)carbonyl]-2-isopropylbenzanilide, and the mixture was warmed up to room temperature. Filtration was carried out when di... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ether | c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | c1ccccc1.c1ccc2c(c1)[NH]CCc1[nH]cnc12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1[nH]cnc12 | null | null | null | 1 | CC(C)c1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3ccccc32)cc1.O>>Cc1nc2c([nH]1)-c1ccccc1N(C(=O)c1ccc(NC(=O)c3ccccc3OC(C)C)cc1)CC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d43c74a9d90473996cdace2ba79d6f8 | Cl>>Cl | COC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)N1CCC2=C(C3=C1C=CC=C3)NC(=N2)C.Cl.C(C)(=O)OCC>>Cl.COC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)N1CCC2=C(C3=C1C=CC=C3)NC(=N2)C | [ClH:32]>>[ClH:32] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 6-[(2'-Methoxy-4-biphenylyl)carbonyl]-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine was dissolved in 4.8 ml of ethyl alcohol, the solution was mixed with 0.44 ml of 4N hydrochloric acid-ethyl acetate and cooled on an ice bath to effect crystal formation, and then the thus formed crystals were collected by fil... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d699a2fd0bfb49f2b2d9d51a6a3e6ab2 | BrCCCCBr.CCOC(C)=O.N#CCc1ccccc1.O>>O=C(O)C1(c2ccccc2)CCCC1 | C(C1=CC=CC=C1)C#N.BrCCCCBr.O.C(C)(=O)OCC>>C1(=CC=CC=C1)C1(CCCC1)C(=O)O | Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.CCOC(C)=[O:1].N#[C:2][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[OH2:3]>>[O:1]=[C:2]([OH:3])[C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH2:13][CH2:14]1 | BrCCCCBr.CCOC(C)=O.N#CCc1ccccc1.O | O=C(O)C1(c2ccccc2)CCCC1 | null | null | O1CCCC1.[H-].[Na+] | Acylation | OtherReaction | 598d21fce22d09c3bae94a7cf2d53009fcc10a866bc3741483fa873ad200cb91 | 3aba3ab6e23932b358809e97064fffaa9ac61a401ccbbd64df773b827e78c111 | c1ccc(C2CCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-Br.C-C-O-C(-C)=[O;H0;D1;+0:5].N#[C;H0;D2;+0:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10].[OH2;D0;+0:11]>>[O;H0;D1;+0:5]=[C;H0;D3;+0:6](-[OH;D1;+0:11])-[C;H0;D4;+0:7]1(-[c:8](:[c:9]):[c:10])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | null | null | 1 | HOUR | In a stream of argon, 60% sodium hydride was dissolved in 10 ml of tetrahydrofuran, and the solution was mixed with 2.0 g of benzyl cyanide, stirred for 1 hour at room temperature, further mixed with 3.69 g of 1,4-dibromobutane and again stirred for 16 hours at room temperature. The reaction mixture was mixed with wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ester.Nitrile | Carboxylic acid | null | C1CCCC1 | c1ccccc1.C1CCCC1 | HBr | O1CCCC1.[H-].[Na+] | null | 1 | BrCCCCBr.CCOC(C)=O.N#CCc1ccccc1.O>O1CCCC1.[H-].[Na+]>O=C(O)C1(c2ccccc2)CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a3bb18217e0f4155870b6f9c59379a87 | CI.Cc1nc2c([nH]1)-c1ccccc1N(C(=O)c1ccc([N+](=O)[O-])cc1)CC2>>Cc1nc2c(n1C)CCN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1-2 | [H-].[Na+].O.[N+](=O)([O-])C1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=C1.CI>>[N+](=O)([O-])C1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)N=C(N3C)C)C=C1 | I[CH3:7].[CH3:1][c:2]1[n:3][c:4]2[c:5]([nH:6]1)-[c:27]1[c:22]([cH:23][cH:24][cH:25][cH:26]1)[N:10]([C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1)[CH2:9][CH2:8]2>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([n:6]1[CH3:7])[CH2:8][CH2:9][N:10]([C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:1... | CI.Cc1nc2c([nH]1)-c1ccccc1N(C(=O)c1ccc([N+](=O)[O-])cc1)CC2 | Cc1nc2c(n1C)CCN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1-2 | null | null | CN(C=O)C.C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 6567d10a77e90bdf51acf993b92a04165f271a5ae281eb951627268c7a6c60f6 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C(c1ccccc1)N1CCc2[nH]cnc2-c2ccccc21 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c;H0;D3;+0:5]2:[c;H0;D3;+0:6](:[nH;D2;+0:7]:1)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](:[c:12])-[#7:13](-[C:14]=[O;D1;H0:15])-[C:16]-[CH2;D2;+0:17]-2>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c;H0;D3;+0:5]2:[c;H0;D3;+0:6](:[n;H0;D3;+0:7]:1-[CH3;D1;+0:1])-[CH2;D2;+0:17]-[C:16]-[#7:13](-[C:1... | null | [] | null | null | 1 | HOUR | In a stream of argon, 144 mg of 60% sodium hydride was suspended in a small volume of N,N-dimethylformamide to which, with cooling on an ice bath, was then added dropwise a solution prepared by dissolving 500 mg of 6-(4-nitrobenzoyl)-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine in 20 ml of N,N-dimethylformam... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)[NH]CCc1[nH]cnc12 | c1nc2c([nH]1)c1ccccc1NCC2 | c1ccccc1.c1nc2c([nH]1)c1ccccc1NCC2 | HI | CN(C=O)C.C(Cl)(Cl)Cl | null | 1 | CI.Cc1nc2c([nH]1)-c1ccccc1N(C(=O)c1ccc([N+](=O)[O-])cc1)CC2>CN(C=O)C.C(Cl)(Cl)Cl>Cc1nc2c(n1C)CCN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b911c15a1a684981b9d7562f530a2f04 | Cc1nc2c(n1C)CCN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1-2>>Cc1nc2c(n1C)CCN(C(=O)c1ccc(N)cc1)c1ccccc1-2 | [N+](=O)([O-])C1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)N=C(N3C)C)C=C1>>NC1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)N=C(N3C)C)C=C1 | O=[N+:17]([O-])[c:16]1[cH:15][cH:14][c:13]([C:11]([N:10]2[CH2:9][CH2:8][c:5]3[c:4]([n:3][c:2]([CH3:1])[n:6]3[CH3:7])-[c:25]3[c:20]2[cH:21][cH:22][cH:23][cH:24]3)=[O:12])[cH:19][cH:18]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([n:6]1[CH3:7])[CH2:8][CH2:9][N:10]([C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([NH2:17])[cH:18][cH:19]1)[... | Cc1nc2c(n1C)CCN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1-2 | Cc1nc2c(n1C)CCN(C(=O)c1ccc(N)cc1)c1ccccc1-2 | null | [C].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCc2[nH]cnc2-c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A 1.421 g portion of 6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine was dissolved in 50 ml of methyl alcohol, and the solution was mixed with 300 mg of palladium-carbon and subjected to hydrogenation under normal pressure. After completion of the hydrogen absorption, the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1nc2c([nH]1)c1ccccc1NCC2 | Other | [C].[Pd].CO | null | null | Cc1nc2c(n1C)CCN(C(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1-2>[C].[Pd].CO>Cc1nc2c(n1C)CCN(C(=O)c1ccc(N)cc1)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a12f514f3a754a2d8e08fdd22d30526b | CCOC(=O)Cc1cccc(Br)c1>>O=CCc1cccc(Br)c1 | [H-].C(C(C)C)[Al+]CC(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC=1C=C(C=CC1)CC(=O)OCC.BrC=1C=C(C=CC1)CC(=O)OCC>>BrC=1C=C(C=CC1)CC=O | CCO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1>>[O:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1 | CCOC(=O)Cc1cccc(Br)c1 | O=CCc1cccc(Br)c1 | null | null | null | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]>>[O;D1;H0:2]=[CH;D2;+0:1]-[C:3]-[c:4] | null | [] | null | null | null | null | Compound G can be obtained as described in J. Med. Chem. 1995, 38, 4764-4767, and as shown in Reaction Scheme 1. Thus, referring now specifically to Reaction Scheme 1, ethyl 3-bromophenylacetate (Compound B, made by esterification of 3-bromophenylacetic acid) is reduced with diisobutylaluminum hydride (DIBAL H) to yiel... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)Cc1cccc(Br)c1>>O=CCc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b3dbd0407beb47cbade768f03604d785 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 | BrC=1C=C(C=CC1)CC=O.C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>BrC=1C=C(C=CC1)CCCC(=O)OCC | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[CH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1cccc(Br)c1 | CCOC(=O)CCCc1cccc(Br)c1 | null | null | null | C-C Coupling | OtherReaction | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | Compound G can be obtained as described in J. Med. Chem. 1995, 38, 4764-4767, and as shown in Reaction Scheme 1. Thus, referring now specifically to Reaction Scheme 1, ethyl 3-bromophenylacetate (Compound B, made by esterification of 3-bromophenylacetic acid) is reduced with diisobutylaluminum hydride (DIBAL H) to yiel... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72b51fbb7ecd44859f1e2ed402ee2144 | CC1(C)CCC(=O)c2cc(Br)ccc21.Sc1ccccc1>>CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 | C1(CCCC2CC=CC=C12)=O.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.C1(=CC=CC=C1)S.C1CC=CC2=CC=CC=C12>>CC1(CC=C(C2=CC(=CC=C12)Br)SC1=CC=CC=C1)C | O=[C:6]1[CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[c:20]2[c:14]1[cH:15][c:16]([Br:17])[cH:18][cH:19]2.[SH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([S:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | CC1(C)CCC(=O)c2cc(Br)ccc21.Sc1ccccc1 | CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 | null | [Ti](Cl)(Cl)(Cl)Cl | O1CCCC1.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | 0ada3ae671ad3b060b96add65fbcfec1b731cae0a6c858eea87374516a4ac73a | f936d6b76ed560a8fec322bcfbbde18f0a579df08bd9baf16a1cafcec3158898 | C1=C(Sc2ccccc2)c2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[S;H0;D2;+0:8]-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7]):[c:11] | null | [] | null | null | null | null | Reaction Scheme 3 provides further examples for the synthesis of compounds within the scope of Formula 5 where the linking group between the dihydronaphthalene moiety and the Y group is --CH=CH--. In the sequence of reactions described here the oxo function of a starting tetrahydronaphthalene-one moiety is modified bef... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic thiol | Monosulfide | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | c1ccccc1.C1=Cc2ccccc2CC1 | HO- | [Ti](Cl)(Cl)(Cl)Cl.O1CCCC1.C(C)N(CC)CC | null | null | CC1(C)CCC(=O)c2cc(Br)ccc21.Sc1ccccc1>[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1.C(C)N(CC)CC>CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-254a6649ca41404ba268a53b6dace89f | CCOC(=O)CBr.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1>>CCOC(=O)CC1(O)CCC(C)(C)c2ccc(/C=C/c3ccc(C(=O)OCC)cc3)cc21 | C1CCCC2=CC=CC=C12.CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.BrCC(=O)OCC.C1C(CCC2CC=CC=C12)=O>>CC1(C=2C=CC(=CC2C(CC1)(CC(=O)OCC)O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[C:7]1(=[O:8])[CH2:9][CH2:10][C:11]([CH3:12])([CH3:13])[c:14]2[cH:15][cH:16][c:17](/[CH:18]=[CH:19]/[c:20]3[cH:21][cH:22][c:23]([C:24](=[O:25])[O:26][CH2:27][CH3:28])[cH:29][cH:30]3)[cH:31][c:32]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1([OH:8])[CH2:9][CH2:10][C:11]([CH3... | CCOC(=O)CBr.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1 | CCOC(=O)CC1(O)CCC(C)(C)c2ccc(/C=C/c3ccc(C(=O)OCC)cc3)cc21 | null | [Zn] | null | C-C Coupling | Grignard_alcohol | ae6802bc43630c235b581c1f69ee3f400dd59564bb5948df811879329723b99c | 86d8e63c1eeb9e82c583fd2409352b28a569a3f780f9f297e86b8d2f688ca9d6 | C(=C/c1ccc2c(c1)CCCC2)\c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7]-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | Reaction Scheme 5 discloses another example for the preparation of compounds within the scope of Formula 3. In this example the substituent is introduced to replace the oxo function of tetrahydronaphthalene-2-one after the Z--Y(R2)--A--B group has already been coupled to the tetrahydronaphthalene nucleus. Thus, ethyl(E... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ester.Tertiary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | Br- | [Zn] | null | null | CCOC(=O)CBr.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1>[Zn]>CCOC(=O)CC1(O)CCC(C)(C)c2ccc(/C=C/c3ccc(C(=O)OCC)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35d47ce82ae748faaaaa6e03a0967fb0 | CC(C)(C)[Si](C)(C)Cl.CC1(C)CCC(O)c2cc(Br)ccc21>>CC1(C)CCC(O[Si](C)(C)C(C)(C)C)c2cc(Br)ccc21 | BrC=1C=C2C(CCC(C2=CC1)(C)C)O.[Si](C)(C)(C(C)(C)C)Cl>>BrC=1C=C2C(CCC(C2=CC1)(C)C)O[Si](C)(C)C(C)(C)C | Cl[Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14].[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH:6]([OH:7])[c:15]2[cH:16][c:17]([Br:18])[cH:19][cH:20][c:21]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH:6]([O:7][Si:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]2[cH:16][c:17]([Br:18])[cH:19][cH:20][c:2... | CC(C)(C)[Si](C)(C)Cl.CC1(C)CCC(O)c2cc(Br)ccc21 | CC1(C)CCC(O[Si](C)(C)C(C)(C)C)c2cc(Br)ccc21 | null | null | null | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | c1ccc2c(c1)CCCC2 | 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].[C:8]-[C:9](-[OH;D1;+0:10])-[c:11]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[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:11] | null | [] | null | null | null | null | Continuing on with the description of Reaction Scheme 6, 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-hydroxynaphthalene is reacted in the presence of base with t-butyldimethylsilyl chloride to provide 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-(t-butyldimethylsilyloxy)naphthalene (Compound B15). The starting 6-bromo-1,2,3... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2c(c1)CCCC2 | HCl | null | null | null | CC(C)(C)[Si](C)(C)Cl.CC1(C)CCC(O)c2cc(Br)ccc21>>CC1(C)CCC(O[Si](C)(C)C(C)(C)C)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d320d86af6964f16a5a4454d35f645dc | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O[Si](C)(C)C(C)(C)C)CCC4(C)C)ccc2c1>>CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1 | CC1(C=2C=CC(=CC2C(CC1)O[Si](C)(C)C(C)(C)C)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C | CC(C)(C)[Si](C)(C)[O:19][CH:18]1[c:16]2[c:15]([cH:14][cH:13][c:12](-[c:11]3[cH:10][c:9]4[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:28][c:27]4[cH:26][cH:25]3)[cH:17]2)[C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15... | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O[Si](C)(C)C(C)(C)C)CCC4(C)C)ccc2c1 | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1 | null | null | null | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | c1ccc2cc(-c3ccc4c(c3)CCCC4)ccc2c1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Continuing on with the description of Reaction Scheme 6, 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-hydroxynaphthalene is reacted in the presence of base with t-butyldimethylsilyl chloride to provide 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-(t-butyldimethylsilyloxy)naphthalene (Compound B15). The starting 6-bromo-1,2,3... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O[Si](C)(C)C(C)(C)C)CCC4(C)C)ccc2c1>>CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36cb55ed95f3473c9784f61cd4f7575f | CC1(C)CCC(=O)c2cc(Br)ccc21.C[C](C)(C)[Mg][Cl]>>CC(C)(C)C1=CCC(C)(C)c2ccc(Br)cc21 | C1(=CC=C(C=C1)S(=O)(=O)O)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.C(C)(C)(C)[Mg]Cl>>BrC1=CC=C2C(CC=C(C2=C1)C(C)(C)C)(C)C | O=[C:5]1[CH2:6][CH2:7][C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]21.[Cl][Mg][C:2]([CH3:1])([CH3:3])[CH3:4]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]1=[CH:6][CH2:7][C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]21 | CC1(C)CCC(=O)c2cc(Br)ccc21.C[C](C)(C)[Mg][Cl] | CC(C)(C)C1=CCC(C)(C)c2ccc(Br)cc21 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | cad3ebb460626e0b3c0c5e79b5d003dc2c6720d4441d1a3b1dd15d07bbe3c73a | 6765e06b4fce5c2cc632b64cfcd2cebf695ba9495ab888b1531784cd07e6e026 | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[C;D1;H3:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[Mg]-[Cl]>>[C;D1;H3:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7] | null | [] | null | null | null | null | Reaction Scheme 9 discloses the preferred method of synthesis of a starting material from which certain examples for compounds of the invention within the scope of Formula 6 are preferably made. In accordance with this scheme 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) is reacted with t-butylmagne... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HCl.Mg | O1CCCC1 | null | null | CC1(C)CCC(=O)c2cc(Br)ccc21.C[C](C)(C)[Mg][Cl]>O1CCCC1>CC(C)(C)C1=CCC(C)(C)c2ccc(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40f1c896966e44febe91ff5b043dfe79 | CCO.O=C(O)Cc1ccc(Br)cc1>>CCOC(=O)Cc1ccc(Br)cc1 | BrC1=CC=C(C=C1)CC(=O)O.OS(=O)(=O)O.C(C)O.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(CC1=CC=C(C=C1)Br)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1 | CCO.O=C(O)Cc1ccc(Br)cc1 | CCOC(=O)Cc1ccc(Br)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[C;D1;H3:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | null | null | A solution of 43 g (200 mmol) of 4-bromophenylacetic acid and 0.2 g of conc. H2SO4 in 470 ml of ethanol was refluxed for 16 hours. The reaction mixture was cooled to ambient temperature, stirred with 6 g of solid K2CO3 for 30 minutes and then filtered. The filtrate was concentrated in vacuo, diluted with Et2O (200 ml),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)Cc1ccc(Br)cc1>>CCOC(=O)Cc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f9d9123ba1f04c7494e0e6ceb5f56621 | CCOC(=O)Cc1ccc(Br)cc1.O=C(O)Cc1cccc(Br)c1>>CCOC(=O)Cc1cccc(Br)c1 | C(C)OC(CC1=CC=C(C=C1)Br)=O.C(C)OC(CC1=CC=C(C=C1)Br)=O.BrC=1C=C(C=CC1)CC(=O)O>>C(C)OC(CC1=CC(=CC=C1)Br)=O | O=C(Cc1ccc(Br)cc1)O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[cH:13]1 | CCOC(=O)Cc1ccc(Br)cc1.O=C(O)Cc1cccc(Br)c1 | CCOC(=O)Cc1cccc(Br)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 042509afb850b7ae8d1b416db2a7d99308189364e9a5fcf96184b5eead3a8ee2 | b4a89122cda2e12df412f0af60b7839f49d2933dbee64ad6cf28e3443255e82d | c1ccccc1 | Br-c1:c:c:c(-C-C(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2]):c:c:1.[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | Employing the same general procedure as for the preparation of ethyl(4-bromophenyl)acetate (Compound A), 100 g (463 mmol) of 3-bromophenylacetic acid was converted into the title compound (yellow oil) using 2 g of conc. H2SO4 and 500 ml of ethanol. PMR (CDCl3): δ 1.26 (3H, t, J=7.0 Hz), 3.56 (2H, s), 4.16 (2H, q, J=7.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Ester | Ester | c1ccccc1 | null | c1ccccc1 | HBr | null | null | null | CCOC(=O)Cc1ccc(Br)cc1.O=C(O)Cc1cccc(Br)c1>>CCOC(=O)Cc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2d92d9e8c6e2432b8ddf16f2363dcbf0 | CCOC(=O)Cc1ccc(Br)cc1>>O=CCc1ccc(Br)cc1 | [H-].C(C(C)C)[Al+]CC(C)C.C(C)OC(CC1=CC=C(C=C1)Br)=O.C(C)OC(CC1=CC=C(C=C1)Br)=O.[H-].C(C(C)C)[Al+]CC(C)C>>BrC1=CC=C(C=C1)CC=O | CCO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>>[O:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1 | CCOC(=O)Cc1ccc(Br)cc1 | O=CCc1ccc(Br)cc1 | null | null | C(Cl)Cl | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]>>[O;D1;H0:2]=[CH;D2;+0:1]-[C:3]-[c:4] | null | [] | -78 | CELSIUS | null | null | To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl(4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an ad... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccccc1 | HO- | C(Cl)Cl | -78 | null | CCOC(=O)Cc1ccc(Br)cc1>C(Cl)Cl>O=CCc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dfb925c910634ae6a49615162b2da243 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1ccc(Br)cc1>>CCOC(=O)C=CCc1ccc(Br)cc1 | BrC1=CC=C(C=C1)CC=O.ClCl.C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>BrC1=CC=C(C=C1)CC=CC(=O)OCC | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[CH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1ccc(Br)cc1 | CCOC(=O)C=CCc1ccc(Br)cc1 | null | null | C(Cl)Cl | C-C Coupling | Wittig reaction with triphenylphosphorane | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | 16 | HOUR | To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl(4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an ad... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | C(Cl)Cl | null | 16 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=CCc1ccc(Br)cc1>C(Cl)Cl>CCOC(=O)C=CCc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd88e66de55049f7ad9914c5bfbadd5a | CCOC(=O)CCCc1ccc(Br)cc1.CCOC(=O)Cc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 | C(C)OC(CCCC1=CC=C(C=C1)Br)=O.C(C)OC(CCCC1=CC=C(C=C1)Br)=O.BrC=1C=C(C=CC1)CC(=O)OCC.BrC=1C=C(C=CC1)CC(=O)OCC>>BrC=1C=C(C=CC1)CCCC(=O)OCC | Br[c:12]1[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:15][cH:13]1.CCOC(=O)Cc1cccc([Br:14])c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | CCOC(=O)CCCc1ccc(Br)cc1.CCOC(=O)Cc1cccc(Br)c1 | CCOC(=O)CCCc1cccc(Br)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 434198cbd735c3e210a63326c76eb747349a83f3c9f01bbe2eff06a955199ae4 | d0508361c24262840b1fde4be03be16061d0fd8ada9f40d1b6c5100911d70222 | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.C-C-O-C(=O)-C-c1:c:c:c:c(-[Br;H0;D1;+0:7]):c:1>>[Br;H0;D1;+0:7]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | Employing the same general multistep preparation as for ethyl4-(4-bromophenyl)butanoate (Compound C), 60 g (246 mmol) of ethyl (3-bromophenyl)acetate (Compound B) was converted into the title compound (oil) using 255 ml (255 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M in hexane), 85.8 g (250 mmol) of (carbethoxyme... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | null | null | CCOC(=O)CCCc1ccc(Br)cc1.CCOC(=O)Cc1cccc(Br)c1>>CCOC(=O)CCCc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cfa73652b7a144b88fc260b76438c1a1 | CC(=O)O.CC1(C)CCCc2cc(Br)ccc21>>CC1(C)CCC(=O)c2cc(Br)ccc21 | C(C)(=O)OC(C)=O.C(C)(=O)O.BrC=1C=C2CCCC(C2=CC1)(C)C.BrC=1C=C2CCCC(C2=CC1)(C)C>>BrC1=CC=C2C(CCC(C2=C1)=O)(C)C | CC(O)=[O:7].[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]21 | CC(=O)O.CC1(C)CCCc2cc(Br)ccc21 | CC1(C)CCC(=O)c2cc(Br)ccc21 | null | [O-2].[O-2].[O-2].[Cr+6] | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 06b75b2d4fdd308e9ae14eb39d86aacd806c7aa02919897cbe294a3bc24409c8 | bd34f155ea119239d8395e98fadac5c7a5507ae7ce37531b09373c8830fc562b | O=C1CCCc2ccccc21 | C-C(-O)=[O;H0;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:1])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | To a cold mixture (0° C.) of 209 g (200 mmol) of chromium trioxide, 100 ml (1.06 mol) of acetic anhydride and 200 ml (3.5 mol) of acetic acid was added a solution of 10 g (41.8 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F) in 125 ml of benzene. The reaction mixture was stirred for 1 hour, que... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | [O-2].[O-2].[O-2].[Cr+6].C1=CC=CC=C1 | null | 1 | CC(=O)O.CC1(C)CCCc2cc(Br)ccc21>[O-2].[O-2].[O-2].[Cr+6].C1=CC=CC=C1>CC1(C)CCC(=O)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6185c04dffd4470aa6c626e04baee724 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1cscn1>>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(c2nccs2)=CCC3(C)C)cc1 | S1C=NC=C1.C(CCC)[Li].[NH4+].[Cl-].CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)/C=C/C1=CC=C(C(=O)OCC)C=C1)C>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CN1)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | O=S(=O)(O[C:18]1=[CH:24][CH2:25][C:26]([CH3:27])([CH3:28])[c:15]2[cH:14][cH:13][c:12](/[CH:11]=[CH:10]/[c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:30][cH:29]3)[cH:17][c:16]21)C(F)(F)F.[cH:19]1[n:20][cH:21][cH:22][s:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](/[CH:10]=[CH:11]/[c:12]2[c... | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1cscn1 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(c2nccs2)=CCC3(C)C)cc1 | null | [Cl-].[Zn+2].[Cl-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1CCOC1.O1CCCC1 | C-C Coupling | OtherReaction | eaab030020d56665bc4d9779272e990b86f74e43fc7c76c6cb4d4209c9406879 | 253c3b9fccee9bf420e0fb1f267e37bad5aa0c206427cb57447e420babcc09c8 | C1=C(c2nccs2)c2cc(/C=C/c3ccccc3)ccc2CC1 | F-C(-F)(-F)-S(=O)(=O)-O-[C;H0;D3;+0:1](=[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[#16;a:7]1:[c:8]:[c:9]:[#7;a:10]:[cH;D2;+0:11]:1>>[C:3]-[C:2]=[C;H0;D3;+0:1](-[c;H0;D3;+0:11]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | To a cold (-78° C.) solution of thiazole (0.38 g (0.10 mL, 1.4 mmol) in THF (2.0 mL) was added n-butyl lithium (1.6M solution in hexanes, 0.5 mL, 0.8 mmol) and stirred for 30 min. To this solution was added 0.176 g (1.3 mmol) of zinc chloride in 3.0 mL of tetrahydrofuran and stirred for 45 min. The resulting turbid sol... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | C1=Cc2ccccc2CC1.c1cscn1 | c1cscn1.C1=Cc2ccccc2CC1 | c1ccccc1.c1cscn1.C1=Cc2ccccc2CC1 | TfOH.HO- | [Cl-].[Zn+2].[Cl-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.O1CCCC1 | null | 0.5 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1cscn1>[Cl-].[Zn+2].[Cl-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.O1CCCC1>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(c2nccs2)=... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-833ae973b3214608bac2a8fbd227ff25 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1ccsc1>>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1.[Li][c]1cccs1 | CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.S1C=CC=C1.C(CCC)[Li]>>[Li]C=1SC=CC1.CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | O=[S:23](=O)(O[C:18]1=[CH:24][CH2:25][C:26]([CH3:27])([CH3:28])[c:15]2[cH:14][cH:13][c:12](/[CH:11]=[CH:10]/[c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:30][cH:29]3)[cH:17][c:16]21)[C:19](F)(F)F.CC1(C)CC=C(OS(=O)(=O)C(F)(F)F)c2cc(/C=C/c3ccc(C(=O)O[CH2:22][CH3:21])c[cH:20]3)ccc21.[cH:32]1[cH:33][cH:34][c... | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1ccsc1 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1.[Li][c]1cccs1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Cl-].[Zn+2].[Cl-] | O1CCCC1 | C-C Coupling | OtherReaction | 3ab4abadd4882aae99f9c2cd26eb7fcdba47688026b16b611ccf1d84a12340e9 | 94f8d63ba54e5b4480bbb52ffd8b132aaa72b3e60c8cdc4274bdef82a5ac73e2 | C1=C(c2cccs2)c2cc(/C=C/c3ccccc3)ccc2CC1.c1ccsc1 | C-C1(-C)-C-C=C(-O-S(=O)(=O)-C(-F)(-F)-F)-c2:c:c(/C=C/c3:[cH;D2;+0:1]:c:c(-C(=O)-O-[CH2;D2;+0:2]-[CH3;D1;+0:3]):c:c:3):c:c:c:2-1.F-[C;H0;D4;+0:4](-F)(-F)-[S;H0;D4;+0:5](=O)(=O)-O-[C;H0;D3;+0:6](=[C:7]-[C:8])-[c:9](:[c:10]):[c:11].[#16;a:12]1:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:1>>[C:8]-[C:7]=[C;H0;D3;+0:6](-[c;H0;D3;+0:4... | null | [] | -78 | CELSIUS | 35 | MINUTE | A solution of lithiothiophene was prepared by the addition of 0.10 g (0.095 mL, 1.2 mmol) of thiophene to a cold solution (-78° C.) of 0.61 g (0.90 mL, 1.4 mmol, 1.6M in hexanes) of n-butyl lithium in 2.0 mL of tetrahydrofuran. The solution was stirred at -78° C. for 35 min and then a solution of 0.158 g (1.2 mmol) of ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate.Ester | Aryl lithium | C1=Cc2ccccc2CC1.C1=Cc2ccccc2CC1.c1ccccc1.c1ccsc1 | c1ccsc1.C1=Cc2ccccc2CC1.c1ccsc1 | c1ccccc1.c1ccsc1.C1=Cc2ccccc2CC1.c1ccsc1 | TfOH.HO- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Cl-].[Zn+2].[Cl-].O1CCCC1 | -78 | 0.583333 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1ccsc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Cl-].[Zn+2... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6359f090cbac49c6a126e41999e4f8b9 | C=Cc1ccc(C(=O)OCC)cc1.CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21>>CCOC(=O)c1ccc(/C=C/c2cccc3c2C(Sc2ccccc2)=CCC3(C)C)cc1 | BrC1=CC=2C(=CCC(C2C=C1)(C)C)SC1=CC=CC=C1.C(=C)C1=CC=C(C(=O)OCC)C=C1.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C>>CC1(C=2C=CC=C(C2C(=CC1)SC1=CC=CC=C1)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]=[CH2:11])[cH:31][cH:32]1.Br[c:13]1[cH:12][c:17]2[c:16]([cH:15][cH:14]1)[C:28]([CH3:29])([CH3:30])[CH2:27][CH:26]=[C:18]2[S:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](/[CH:10]=[CH:11]/[c:12]2[cH:1... | C=Cc1ccc(C(=O)OCC)cc1.CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 | CCOC(=O)c1ccc(/C=C/c2cccc3c2C(Sc2ccccc2)=CCC3(C)C)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)N(CC)CC | C-C Coupling | OtherReaction | d6db5010b59f0381092da76cd6769358edce2251432e88a0ee3eec12ec5f513f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C1=C(Sc2ccccc2)c2c(/C=C/c3ccccc3)cccc2CC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[cH;D2;+0:6]:1)-[C:7](-[#16:8])=[C:9]-[C:10].[CH2;D1;+0:11]=[C:12]-[c:13]>>[#16:8]-[C:7](=[C:9]-[C:10])-[c:5]1:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:[c;H0;D3;+0:6]:1/[CH;D2;+0:11]=[C:12]/[c:13] | null | [] | 90 | CELSIUS | null | null | To a degassed solution of 0.35 g (1.0 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(phenylthio)-naphthalene (Compound A35) and 0.34 g (1.9 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 0.066 g (0.2 mmol) of tri-o-tolylphosphine and then 0.025 g (0.1 mmol) of palladium(II) acetate. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | c1ccccc1.c1ccccc1.C1=Cc2ccccc2CC1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)N(CC)CC | 90 | null | C=Cc1ccc(C(=O)OCC)cc1.CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)N(CC)CC>CCOC(=O)c1ccc(/C=C/c2cccc3c2C(Sc2ccccc2)=CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b1bd58830652436484aeb0d21b29efe6 | C=Cc1ccc(C(=O)OCC)cc1.CCSC1=CCC(C)(C)c2ccc(Br)cc21>>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(SCC)=CCC3(C)C)cc1 | BrC1=CC=2C(=CCC(C2C=C1)(C)C)SCC.C(=C)C1=CC=C(C(=O)OCC)C=C1.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C>>CC1(C=2C=CC(=CC2C(=CC1)SCC)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]=[CH2:11])[cH:27][cH:28]1.Br[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([S:19][CH2:20][CH3:21])=[CH:22][CH2:23][C:24]2([CH3:25])[CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](/[CH:10]=[CH:11]/[c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:... | C=Cc1ccc(C(=O)OCC)cc1.CCSC1=CCC(C)(C)c2ccc(Br)cc21 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(SCC)=CCC3(C)C)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)N(CC)CC | C-C Coupling | Heck terminal vinyl | d6db5010b59f0381092da76cd6769358edce2251432e88a0ee3eec12ec5f513f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C1=Cc2cc(/C=C/c3ccccc3)ccc2CC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].[CH2;D1;+0:8]=[C:9]-[c:10]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](/[CH;D2;+0:8]=[C:9]/[c:10]):[c:2]:[c:3] | null | [] | 90 | CELSIUS | null | null | To a degassed solution of 0.50 g (1.7 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalene (Compound A36) and 0.45 g (2.5 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 109 mg (0.36 mmol) of tri-o-tolylphosphine and then 35 mg (0.16 mmol) of palladium(II) acetate. The reaction was h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | c1ccccc1.C1=Cc2ccccc2CC1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)N(CC)CC | 90 | null | C=Cc1ccc(C(=O)OCC)cc1.CCSC1=CCC(C)(C)c2ccc(Br)cc21>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)N(CC)CC>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(SCC)=CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ccd6fb9e203040fbbcdbd667f32b7bf3 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.SCCCS>>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(C2SCCCS2)CCC3(C)C)cc1 | CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.C(CCS)S.C(Cl)Cl>>CC1(C=2C=CC(=CC2C(CC1)C1SCCCS1)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | O=[C:18]1[c:16]2[c:15]([cH:14][cH:13][c:12](/[CH:11]=[CH:10]/[c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:31][cH:30]3)[cH:17]2)[C:27]([CH3:28])([CH3:29])[CH2:26][CH2:25]1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)[C:19](=O)CCC3(C)C)cc1.[SH:20][CH2:21][CH2:22][CH2:23][SH:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c... | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.SCCCS | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(C2SCCCS2)CCC3(C)C)cc1 | null | null | C([O-])([O-])=O.[K+].[K+] | Heteroatom Alkylation and Arylation | OtherReaction | 64dafd51f6e96d2f44dadf0a6d95a9dbc5cf350f99e7383f9b372b1304b1e932 | da72bab5ffc932eb295072267fea429a9d06ee1d767d90827ba9b07cdc2bf904 | C(=C/c1ccc2c(c1)C(C1SCCCS1)CCC2)\c1ccccc1 | C-C-O-C(=O)-c1:c:c:c(/C=C/c2:c:c:c3:c(:c:2)-[C;H0;D3;+0:1](=O)-C-C-C-3(-C)-C):c:c:1.O=[C;H0;D3;+0:2](-[C:3]-[C:4])-[c:5](:[c:6]):[c:7].[SH;D1;+0:8]-[C:9]-[C:10]-[C:11]-[SH;D1;+0:12]>>[C:4]-[C:3]-[CH;D3;+0:2](-[CH;D3;+0:1]1-[S;H0;D2;+0:8]-[C:9]-[C:10]-[C:11]-[S;H0;D2;+0:12]-1)-[c:5](:[c:6]):[c:7] | null | [] | null | null | 4 | HOUR | To a cold solution (0° C.) of 140 mg (0.40 mmol) of ethyl(E)-4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2), in 6.0 mL of methylene chloride was added dropwise 130 mg (0.12 mL, 1.2 mmol) of 1,3-propanedithiol and 0.17 g (0.15 mL, 102 mmol) of borontrifluoride diethyl etherate.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Aliphatic thiol.Aliphatic thiol | Monosulfide.Monosulfide | c1ccc2c(c1)CCCC2.c1ccccc1.c1ccc2c(c1)CCCC2 | C1CSCSC1.c1ccc2c(c1)CCCC2 | c1ccccc1.C1CSCSC1.c1ccc2c(c1)CCCC2 | HO- | C([O-])([O-])=O.[K+].[K+] | null | 4 | CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.SCCCS>C([O-])([O-])=O.[K+].[K+]>CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(C2SCCCS2)CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-223a80a8841041078a01144bb56456f4 | CCOC(=O)CBr.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1>>CCCOC(=O)C1(O)CCC(C)(C)c2ccc(/C=C/c3ccc(C(=O)OCC)cc3)cc21 | CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C.C1=CC=CC=C1.C1=CC=CC=C1.BrCC(=O)OCC>>CC1(C=2C=CC(=CC2C(CC1)(C(=O)OCCC)O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C | Br[CH2:7][C:5]([O:4][CH2:3][CH3:2])=[O:6].O=C1[CH2:9][CH2:10][C:11]([CH3:12])([CH3:13])[c:14]2[cH:15][cH:16][c:17](/[CH:18]=[CH:19]/[c:20]3[cH:21][cH:22][c:23]([C:24](=[O:25])[O:26][CH2:27][CH3:28])[cH:29][cH:30]3)[cH:31][c:32]21.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=[O:8])CCC3(C)C)cc1>>[CH3:1][CH2:2][CH2:3][O:4][C:5](=[O:6... | CCOC(=O)CBr.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1 | CCCOC(=O)C1(O)CCC(C)(C)c2ccc(/C=C/c3ccc(C(=O)OCC)cc3)cc21 | null | [Zn] | null | Heteroatom Alkylation and Arylation | OtherReaction | e9daa679284560e3818bb78145ca809068888d6601447cd2e1942192e8d7b935 | 0d4b3a07af04e7d8299f6f866f25c8b805b051e483ac6e2127853c0cc486c00a | C(=C/c1ccc2c(c1)CCCC2)\c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]-[CH3;D1;+0:6].C-C-O-C(=O)-c1:c:c:c(/C=C/c2:c:c:c3:c(:c:2)-C(=[O;H0;D1;+0:7])-C-C-C-3(-C)-C):c:c:1.O=C1-[CH2;D2;+0:8]-[C:9]-[C:10]-[c:11](:[c:12]):[c;H0;D3;+0:13]-1:[c:14]:[c:15]/[C:16]=[C:17]>>[C:17]=[C:16]/[c:15]:[c:14]:[c;H0;D3;+0:13]1:[c:11](:[c:12])-[C:10]-[C:9]-[CH... | null | [] | null | null | null | null | To a refluxing solution of 0.75 g (11.5 mmol) of granular zinc in 5.0 mL of benzene was added a solution of ethyl(E)-4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2) in 5.0 mL of benzene followed by 0.27 g (0.18 mmol) of ethyl bromoacetate. The resulting mixture was refluxed for... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone.Ester.Ester | Ester.Tertiary alcohol | c1ccc2c(c1)CCCC2.c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | HBr | [Zn] | null | null | CCOC(=O)CBr.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1.CCOC(=O)c1ccc(/C=C/c2ccc3c(c2)C(=O)CCC3(C)C)cc1>[Zn]>CCCOC(=O)C1(O)CCC(C)(C)c2ccc(/C=C/c3ccc(C(=O)OCC)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-becf0ee7c3024fadba4ea32c31403111 | CC1(C)CCC(=O)c2cc(Br)ccc21.Sc1ccccc1>>CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 | BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.C1CCOC1.C1(=CC=CC=C1)S.C(C)N(CC)CC.C1CCOC1>>CC1(CC=C(C2=CC(=CC=C12)Br)SC1=CC=CC=C1)C | O=[C:6]1[CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[c:20]2[c:14]1[cH:15][c:16]([Br:17])[cH:18][cH:19]2.[SH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([S:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]21 | CC1(C)CCC(=O)c2cc(Br)ccc21.Sc1ccccc1 | CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 | null | [Ti](Cl)(Cl)(Cl)Cl | O | Heteroatom Alkylation and Arylation | OtherReaction | 0ada3ae671ad3b060b96add65fbcfec1b731cae0a6c858eea87374516a4ac73a | f936d6b76ed560a8fec322bcfbbde18f0a579df08bd9baf16a1cafcec3158898 | C1=C(Sc2ccccc2)c2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[S;H0;D2;+0:8]-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7]):[c:11] | null | [] | null | null | 5 | HOUR | To a stirred solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G, 1.48 g, 5.9 mmol), titanium tetrachloride (1.09 g, 5.7 mmol) and THF (10 mL) was added a mixture of thiophenol (660 mg, 6 mmol), triethylamine (1.16 g, 11.5 mmol) and THF (20 mL) via an addition funnel at ambient temperature. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic thiol | Monosulfide | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | c1ccccc1.C1=Cc2ccccc2CC1 | HO- | [Ti](Cl)(Cl)(Cl)Cl.O | null | 5 | CC1(C)CCC(=O)c2cc(Br)ccc21.Sc1ccccc1>[Ti](Cl)(Cl)(Cl)Cl.O>CC1(C)CC=C(Sc2ccccc2)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-afbd95ad9dd44e7e978ad560efb01622 | CC1(C)CCC(=O)c2cc(Br)ccc21.CCS>>CCSC1=CCC(C)(C)c2ccc(Br)cc21 | BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.C(C)S.C(C)N(CC)CC>>BrC1=CC=2C(=CCC(C2C=C1)(C)C)SCC | O=[C:4]1[CH2:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21.[CH3:1][CH2:2][SH:3]>>[CH3:1][CH2:2][S:3][C:4]1=[CH:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21 | CC1(C)CCC(=O)c2cc(Br)ccc21.CCS | CCSC1=CCC(C)(C)c2ccc(Br)cc21 | null | [Ti](Cl)(Cl)(Cl)Cl | O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | bda6e7a342b4c92698d6328240364017658687b3f6d783caade4c130bf5f7284 | 643de5ae757bb3e6c9835c2c9ec31b7c88e55e46a044a7a875bb5d5888cf6cf3 | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[C;D1;H3:8]-[C:9]-[SH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[S;H0;D2;+0:10]-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7] | null | [] | null | null | 10 | MINUTE | To a solution of 1.03 g (4.1 mmol) of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) in 30.0 mL of tetrahydrofuran, was added dropwise 0.49 g (0.85 mL, 7.8 mmol) of titaniumtetrachloride and the resulting solution stirred for 10 min. A solution of 35 mg (0.50 mL, 6.7 mmol) of ethanethiol and 0.54 g (... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aliphatic thiol | Monosulfide | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | [Ti](Cl)(Cl)(Cl)Cl.O.O1CCCC1 | null | 0.166667 | CC1(C)CCC(=O)c2cc(Br)ccc21.CCS>[Ti](Cl)(Cl)(Cl)Cl.O.O1CCCC1>CCSC1=CCC(C)(C)c2ccc(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-97b20453788c4bc8828b820164729c18 | CC1(C)CCCc2cc(B(O)O)ccc21.CCOC(=O)c1ccc2cc(Br)ccc2c1>>CCOC(=O)c1ccc2cc(C3Cc4ccccc4C(C)(C)C3)ccc2c1 | C(C)(=O)OCC.BrC=1C=C2C=CC(=CC2=CC1)C(=O)OCC.C1(=CC=CC=C1)C.CC1(C=2C=CC(=CC2CCC1)B(O)O)C>>C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)C1CC(C=2C=CC=CC2C1)(C)C | OB(O)[c:16]1[cH:15][c:14]2[c:19]([cH:18][cH:17]1)[C:20]([CH3:21])([CH3:22])[CH2:23][CH2:12][CH2:13]2.Br[c:11]1[cH:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:27][c:26]2[cH:25][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11]([CH:12]3[CH2:13][c:14]4[cH:15][cH:16][cH:17][... | CC1(C)CCCc2cc(B(O)O)ccc21.CCOC(=O)c1ccc2cc(Br)ccc2c1 | CCOC(=O)c1ccc2cc(C3Cc4ccccc4C(C)(C)C3)ccc2c1 | null | null | C([O-])([O-])=O.[Na+].[Na+].CCCCCC.CO.C(=O)([O-])[O-].[Na+].[Na+] | C-C Coupling | OtherReaction | 8c1ecf349dc0cac2cc32df7a1092f55021e4e4a0fc1edd7e41af351130e7178a | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc2c(c1)CCC(c1ccc3ccccc3c1)C2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]-[C:9]-[CH2;D2;+0:10]-[C:11]-[C:12]):[c:13]:[c:14]>>[C:12]-[C:11]-[CH;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[c:8]:[c:7]:[cH;D2;+0:6]:[c:13]:[c:14] | null | [] | 80 | CELSIUS | null | null | To a degassed solution of 0.39 g (1.4 mmol) of ethyl 6-bromo-naphthalene-2-carboxylate and 3.0 mL of toluene, was added sequentially 49 mg (0.04 mmol) of tetrakis-triphenylphosphine palladium(0), 2.0 mL (2.0 mmol) of 1M sodium carbonate and then a solution of 0.32 g (1.6 mmol) of (5,6,7,8-tetrahydro-5,5-dimethylnaphth-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCCC2.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | HBr.B | C([O-])([O-])=O.[Na+].[Na+].CCCCCC.CO.C(=O)([O-])[O-].[Na+].[Na+] | 80 | null | CC1(C)CCCc2cc(B(O)O)ccc21.CCOC(=O)c1ccc2cc(Br)ccc2c1>C([O-])([O-])=O.[Na+].[Na+].CCCCCC.CO.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(=O)c1ccc2cc(C3Cc4ccccc4C(C)(C)C3)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9be964bec0914ee8a55f4080f106b48c | CC1(C)CCC(O[Si](C)(C)C(C)(C)C)c2cc(B(O)O)ccc21.CCOC(=O)c1cccc2cc(Br)ccc12>>CCOC(=O)c1ccc2cc(C3CC(C)(C)c4ccccc4C3O[Si](C)(C)C(C)(C)C)ccc2c1 | CC1(C=2C=CC(=CC2C(CC1)O[Si](C)(C)C(C)(C)C)B(O)O)C.BrC=1C=C2C=CC=C(C2=CC1)C(=O)OCC.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>>C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)C1CC(C=2C=CC=CC2C1O[Si](C)(C)C(C)(C)C)(C)C | OB(O)[c:20]1[cH:19][cH:18][c:17]2[c:22]([cH:21]1)[CH:23]([O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:12][CH2:13][C:14]2([CH3:15])[CH3:16].Br[c:11]1[cH:10][c:9]2[c:34]([c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][cH:35]2)[cH:33][cH:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH... | CC1(C)CCC(O[Si](C)(C)C(C)(C)C)c2cc(B(O)O)ccc21.CCOC(=O)c1cccc2cc(Br)ccc12 | CCOC(=O)c1ccc2cc(C3CC(C)(C)c4ccccc4C3O[Si](C)(C)C(C)(C)C)ccc2c1 | null | null | CO | C-C Coupling | OtherReaction | e7b6f1d120a40f2704f595d417e6c75976f2e148ca7773f9836acb061b27d70f | 4180a79a01f5556153dc91b20f033722a6f8d4c6baaa6b570c0ebf5e6298912a | c1ccc2c(c1)CCC(c1ccc3ccccc3c1)C2 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3]2:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:[c;H0;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c;H0;D3;+0:12]:2:[c:13]:[c:14]:1.O-B(-O)-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]-[C:20](-[#8:21])-[CH2;D2;+0:22]-[C:23]-[C:24]>>[#8:21]-[C:20](-[c:19]:[c:18]:[cH;D2;+0:15]:[c:16]:[c:17])-[... | null | [] | 90 | CELSIUS | null | null | To a degassed solution of 722 mg (2.6 mmol) of ethyl 6-bromo-naphthalenecarboxylate in 6.0 mL of toluene, was added sequentially 90 mg (0.08 mmol) of tetrakis-triphenylphosphine palladium (O), 5.0 mL (10.0 mmol) of 2M sodium carbonate, and a solution of 1.018 g (3.1 mmol) of (5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyld... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Ester | c1ccc2c(c1)CCCC2.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | HBr.B | CO | 90 | null | CC1(C)CCC(O[Si](C)(C)C(C)(C)C)c2cc(B(O)O)ccc21.CCOC(=O)c1cccc2cc(Br)ccc12>CO>CCOC(=O)c1ccc2cc(C3CC(C)(C)c4ccccc4C3O[Si](C)(C)C(C)(C)C)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-03a49a1bcde34b059ad4b6f47e61b002 | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1>>CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(=O)CCC4(C)C)ccc2c1 | CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C.CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C.C[N+]1(CCOCC1)[O-].C(C)(=O)OCC>>C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)C1=CC=2C(CCC(C2C=C1)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[CH:18]([OH:19])[CH2:20][CH2:21][C:22]4([CH3:23])[CH3:24])[cH:25][cH:26][c:27]2[cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]4[c:16]([cH:17]3)[... | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1 | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(=O)CCC4(C)C)ccc2c1 | null | null | C(Cl)Cl.CCCCCC.O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | b5ed2230f6b74a2addb911914d598ef68d7e447cad6e33e5f6091319c5e0b79b | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCc2ccc(-c3ccc4ccccc4c3)cc21 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 3 | HOUR | To a solution of 101 mg (0.27 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-7-yl]naphth-2-oate (Compound B4) in 1.5 mL of methylene chloride was added 50 mg (0.43 mmol) of N-methylmorpholine N-oxide and 6.0 mg (0.017 mmol) of tetrapropylammonium perruthenate(VII). The reaction was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | null | C(Cl)Cl.CCCCCC.O | null | 3 | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1>C(Cl)Cl.CCCCCC.O>CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(=O)CCC4(C)C)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13e57f77780b42eab24c40acb5fbde1d | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1.CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1.COCCl>>CCOC(=O)c1ccc2cc(C3CC(C)(C)c4ccccc4C3OCOC)ccc2c1 | COCCl.O.CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C.CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C.CCN(C(C)C)C(C)C.[I-].C(C)(C)(C)[NH3+]>>C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)C1CC(C=2C=CC=CC2C1OCOC)(C)C | CCOC(=O)c1ccc2cc(-[c:20]3[cH:19][cH:18][c:17]4[c:22]([cH:21]3)[CH:23]([OH:24])[CH2:12][CH2:13][C:14]4([CH3:15])[CH3:16])ccc2c1.CC1(C)CCC(O)c2cc(-[c:11]3[cH:10][c:9]4[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:31][c:30]4[cH:29][cH:28]3)ccc21.Cl[CH2:25][O:26][CH3:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:... | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1.CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1.COCCl | CCOC(=O)c1ccc2cc(C3CC(C)(C)c4ccccc4C3OCOC)ccc2c1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | d1c73ad34a93da1da54be2006a8803b8c04d84dedebae94dc755c6dc7d59ce1c | 49912efb2c127ee8d87392198e88165a6b142ddbbf53b1600b735d645c264d98 | c1ccc2c(c1)CCC(c1ccc3ccccc3c1)C2 | C-C-O-C(=O)-c1:c:c:c2:c:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[OH;D1;+0:7])-[CH2;D2;+0:8]-[C:9]-[C:10]):c:c:c:2:c:1.C-C1(-C)-C-C-C(-O)-c2:c:c(-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):c:c:c:2-1.Cl-[CH2;D2;+0:16]-[#8:17]-[C;D1;H3:18]>>[C:10]-[C:9]-[CH;D3;+0:8](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[... | null | [] | null | null | 14 | HOUR | To a cold (0° C.) solution of 130 mg (0.35 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(hydroxy)-naphth-7-yl]naphth-2-oate (Compound B4) in 2.0 mL of methylene chloride was added 50 mg (0.15 mL, 0.86 mmol) of Hunig's base, followed by 0.21 g (0.20 mL, 2.6 mmol) chloromethyl methyl ether was added and stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 14 | CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1.CCOC(=O)c1ccc2cc(-c3ccc4c(c3)C(O)CCC4(C)C)ccc2c1.COCCl>C(Cl)Cl.C(C)(=O)OCC>CCOC(=O)c1ccc2cc(C3CC(C)(C)c4ccccc4C3OCOC)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1def6f145a124de08c583f52bfc46d3d | CC(C)OB(OC(C)C)OC(C)C.CC1(C)CCCc2cc(Br)ccc21>>CC1(C)CCCc2cc(B(O)O)ccc21 | C(C)(C)OB(OC(C)C)OC(C)C.BrC=1C=C2CCCC(C2=CC1)(C)C.[Li]CCCC>>CC1(C=2C=CC(=CC2CCC1)B(O)O)C | CC(C)O[B:10]([O:11]C(C)C)[O:12]C(C)C.Br[c:9]1[cH:8][c:7]2[c:15]([cH:14][cH:13]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][CH2:6]2>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][c:9]([B:10]([OH:11])[OH:12])[cH:13][cH:14][c:15]21 | CC(C)OB(OC(C)C)OC(C)C.CC1(C)CCCc2cc(Br)ccc21 | CC1(C)CCCc2cc(B(O)O)ccc21 | null | null | C1(=CC=CC=C1)C.Cl | Miscellaneous | Preparation of boronic acids | 44976aedc627652e57cf654966855ab06a9db6d01924d4ea2bf9f8b5ec0f6db6 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc2c(c1)CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)-O-[B;H0;D3;+0:6](-[O;H0;D2;+0:7]-C(-C)-C)-[O;H0;D2;+0:8]-C(-C)-C>>[OH;D1;+0:7]-[B;H0;D3;+0:6](-[OH;D1;+0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 45 | MINUTE | To a cold (-78° C.) solution of 2.02 g (8.4 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene in 11.0 mL of toluene, was added 4.6 g (6.8 mL, 10.9 mmol, 1.6M in hexane) of n-BuLi. The resulting solution was stirred at -78° C. for 45 min. and then 2.40 g (3.0 mL, 12.7 mmol) of triisopropylborate was dropwise a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HBr | C1(=CC=CC=C1)C.Cl | -78 | 0.75 | CC(C)OB(OC(C)C)OC(C)C.CC1(C)CCCc2cc(Br)ccc21>C1(=CC=CC=C1)C.Cl>CC1(C)CCCc2cc(B(O)O)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95296aadd2f34ea7a8a15d80c932bee0 | CC1(C)CCC(=O)c2cc(Br)ccc21.C[C](C)(C)[Mg][Cl]>>CC(C)(C)C1=CCC(C)(C)c2ccc(Br)cc21 | C(C)(C)(C)[Mg]Cl.CO.C1(=CC=C(C=C1)S(=O)(=O)O)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C>>BrC1=CC=C2C(CC=C(C2=C1)C(C)(C)C)(C)C | O=[C:5]1[CH2:6][CH2:7][C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]21.[Cl][Mg][C:2]([CH3:1])([CH3:3])[CH3:4]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5]1=[CH:6][CH2:7][C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]21 | CC1(C)CCC(=O)c2cc(Br)ccc21.C[C](C)(C)[Mg][Cl] | CC(C)(C)C1=CCC(C)(C)c2ccc(Br)cc21 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | cad3ebb460626e0b3c0c5e79b5d003dc2c6720d4441d1a3b1dd15d07bbe3c73a | 6765e06b4fce5c2cc632b64cfcd2cebf695ba9495ab888b1531784cd07e6e026 | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[C;D1;H3:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[Mg]-[Cl]>>[C;D1;H3:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7] | null | [] | -20 | CELSIUS | 1 | HOUR | In a flame dried round bottom flask 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G, 2.0 g, 7.93 mmol) was dissolved in anhydrous THF (50 ml) and 3,4,5,6,-tetrahydro-2(H)-pyrimidinone (DMPU) (11.5 ml, 95.16 mmol) was added, under argon atmosphere. The reaction was then cooled to -20° C. and a solution ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HCl.Mg | C1CCOC1 | -20 | 1 | CC1(C)CCC(=O)c2cc(Br)ccc21.C[C](C)(C)[Mg][Cl]>C1CCOC1>CC(C)(C)C1=CCC(C)(C)c2ccc(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-763f0c0f3fec45499feba900588ad0eb | CCOC(=O)CC1(O)CCC(C)(C)c2ccc(N=Nc3ccc(C(=O)OCC)cc3)cc21>>CCOC(=O)CC1=CCC(C)(C)c2ccc(N=Nc3ccc(C(=O)OCC)cc3)cc21 | CC1(C=2C=CC(=CC2C(CC1)(CC(=O)OCC)O)N=NC1=CC=C(C(=O)OCC)C=C1)C.CC1(C=2C=CC(=CC2C(CC1)(CC(=O)OCC)O)N=NC1=CC=C(C(=O)OCC)C=C1)C.C1CCC(CC1)N=C=NC2CCCCC2>>CC1(C=2C=CC(=CC2C(=CC1)CC(=O)OCC)N=NC1=CC=C(C(=O)OCC)C=C1)C | O[C:7]1([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8][CH2:9][C:10]([CH3:11])([CH3:12])[c:13]2[cH:14][cH:15][c:16]([N:17]=[N:18][c:19]3[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH2:26][CH3:27])[cH:28][cH:29]3)[cH:30][c:31]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1=[CH:8][CH2:9][C:10]([CH3:11])([CH3:12])[c:13]2... | CCOC(=O)CC1(O)CCC(C)(C)c2ccc(N=Nc3ccc(C(=O)OCC)cc3)cc21 | CCOC(=O)CC1=CCC(C)(C)c2ccc(N=Nc3ccc(C(=O)OCC)cc3)cc21 | null | Cl[Cu] | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 55de719a68f8efde968ccdcfe54c921765e82cad5ee57c0bae7adf2d5c6460b3 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=Cc2cc(N=Nc3ccccc3)ccc2CC1 | O-[C;H0;D4;+0:1]1(-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH2;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12] | null | [] | null | null | null | null | A solution of (±)ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate (Compound D1, 108 mg, 0.25 mmol), DCC (55.9 mg, 0.271 mmol) and CuCl (36.6 mg, 0.37 mmol) in 8 ml of dry benzene was heated under reflux for 7 days. After cooling to room temperature, the solids were filtered... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1.c1ccccc1 | HO- | Cl[Cu].C1=CC=CC=C1 | null | null | CCOC(=O)CC1(O)CCC(C)(C)c2ccc(N=Nc3ccc(C(=O)OCC)cc3)cc21>Cl[Cu].C1=CC=CC=C1>CCOC(=O)CC1=CCC(C)(C)c2ccc(N=Nc3ccc(C(=O)OCC)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-febdc1c7fac448b78a423b7cf31b3624 | CC1(C)CCC(=O)c2ccccc21.O=[N+]([O-])O>>CC1(C)CCC(=O)c2cc([N+](=O)[O-])ccc21 | OS(=O)(=O)O.[N+](=O)(O)[O-].OS(=O)(=O)O.CC1(CCC(C2=CC=CC=C12)=O)C>>CC1(CCC(C2=CC(=CC=C12)[N+](=O)[O-])=O)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:14][cH:15][c:16]21.O[N+:11](=[O:12])[O-:13]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]21 | CC1(C)CCC(=O)c2ccccc21.O=[N+]([O-])O | CC1(C)CCC(=O)c2cc([N+](=O)[O-])ccc21 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 5993c528ef8bcdffbf8c0a893a552b598272f75e0f1825b53fb570da12e0cd5d | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1CCCc2ccccc21 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:7]:[c:6]-[C:5]=[O;D1;H0:4] | null | [] | null | null | 20 | MINUTE | To 1.7 mL (3.0g, 30.6 mmol, 18M) H2SO4 at 5° C. (ice-NaCl bath) was slowly added 783.0 mg (4.49 mmol) of 3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-one. A solution of HNO3 (426.7 mg 6.88 mmol, 0.43 mL, 16M), and 1.31 g (0.013 mol, 0.74 mL, 18M) Of H2SO4 were slowly added. After 20 min, ice was added and the resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | null | null | 0.333333 | CC1(C)CCC(=O)c2ccccc21.O=[N+]([O-])O>>CC1(C)CCC(=O)c2cc([N+](=O)[O-])ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c7356141cfe445de9c86a692d1573d44 | CC1(C)CCC(=O)c2cc([N+](=O)[O-])ccc21>>CC1(C)CCC(=O)c2cc(N)ccc21 | CC1(CCC(C2=CC(=CC=C12)[N+](=O)[O-])=O)C.CC1(CCC(C2=CC(=CC=C12)[N+](=O)[O-])=O)C>>CC1(CCC(C2=CC(=CC=C12)N)=O)C | O=[N+:11]([O-])[c:10]1[cH:9][c:8]2[c:14]([cH:13][cH:12]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]21 | CC1(C)CCC(=O)c2cc([N+](=O)[O-])ccc21 | CC1(C)CCC(=O)c2cc(N)ccc21 | null | [Pd] | CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1CCCc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 230.0 mg (1.05 mmol) 3,4-dihydro-4,4-dimethyl-7-nitro-naphthalen-1(2H)-one (Compound D8) in 5.0 mL of EtOAc was stirred at room temperature with a catalytic amount of 10% Pd-C under 1 atm of H2 for 24 h. The catalyst was removed by filtration through a pad of Celite, and the filtrate concentrated under re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCCC2 | Other | [Pd].CCOC(=O)C | null | null | CC1(C)CCC(=O)c2cc([N+](=O)[O-])ccc21>[Pd].CCOC(=O)C>CC1(C)CCC(=O)c2cc(N)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef3ec04d343b4c5986b9256d5cce3915 | CCOC(=O)c1ccc(N=Nc2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1ccsc1>>CCOC(=O)c1ccc(N=Nc2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1 | CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)N=NC1=CC=C(C(=O)OCC)C=C1)C.S1C=CC=C1.[Li]C(C)(C)C>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)N=NC1=CC=C(C(=O)OCC)C=C1)C | O=S(=O)(O[C:18]1=[CH:24][CH2:25][C:26]([CH3:27])([CH3:28])[c:15]2[cH:14][cH:13][c:12]([N:11]=[N:10][c:9]3[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:30][cH:29]3)[cH:17][c:16]21)C(F)(F)F.[cH:19]1[cH:20][cH:21][cH:22][s:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][c... | CCOC(=O)c1ccc(N=Nc2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1ccsc1 | CCOC(=O)c1ccc(N=Nc2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1 | null | [Cl-].[Cl-].[Zn+2].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1CCOC1.[NH4+].[Cl-] | C-C Coupling | OtherReaction | 1635e33838212f74c180ab5d22f02760affb57410f7f71f8f01e910656be3423 | 253c3b9fccee9bf420e0fb1f267e37bad5aa0c206427cb57447e420babcc09c8 | C1=C(c2cccs2)c2cc(N=Nc3ccccc3)ccc2CC1 | F-C(-F)(-F)-S(=O)(=O)-O-[C;H0;D3;+0:1](=[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[#16;a:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[C:3]-[C:2]=[C;H0;D3;+0:1](-[c;H0;D3;+0:11]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | To a cold solution (-78° C.) of thiophene (0.07 ml, 0.75 mmol) in 1.5 ml of THF was added t-BuLi (0.457 ml, 0.75 mmol, 1.7M in pentane) and stirred for 2 h. To this solution, ZnCl2 (168 mg, 1.2 mmol) in 1.5 ml of THF was added. The resulting solution was warmed to room temperature, stirred for 1 h and was added (via ca... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | C1=Cc2ccccc2CC1.c1ccsc1 | c1ccsc1.C1=Cc2ccccc2CC1 | c1ccccc1.c1ccsc1.C1=Cc2ccccc2CC1 | TfOH.HO- | [Cl-].[Cl-].[Zn+2].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.[NH4+].[Cl-] | null | 2 | CCOC(=O)c1ccc(N=Nc2ccc3c(c2)C(OS(=O)(=O)C(F)(F)F)=CCC3(C)C)cc1.c1ccsc1>[Cl-].[Cl-].[Zn+2].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.[NH4+].[Cl-]>CCOC(=O)c1ccc(N=Nc2ccc3c(c2)C(c2cccs2)... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71d8a412e47743ae868fcc2cf8c525e8 | CC(=O)c1ccc2c(c1)C(C)(C)CCC2=O.OCCO>>CC1(C)CCC(=O)c2ccc(C3(C)OCCO3)cc21 | C(CO)O.CC1(CCC(C2=CC(=CC=C12)C(C)=O)=O)C.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.CC1(CCC(C2=CC=C(C=C12)C(C)=O)=O)C>>CC1(OCCO1)C=1C=C2C(CCC(C2=CC1)=O)(C)C | O=[C:12]([c:11]1[cH:10][cH:9][c:8]2[c:19]([cH:18]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7])[CH3:13].[OH:14][CH2:15][CH2:16][OH:17]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]3([CH3:13])[O:14][CH2:15][CH2:16][O:17]3)[cH:18][c:19]21 | CC(=O)c1ccc2c(c1)C(C)(C)CCC2=O.OCCO | CC1(C)CCC(=O)c2ccc(C3(C)OCCO3)cc21 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 2baa95c632045e217509d8ec12cda8674252268fe3f8cb44eb2e5ebe0f27c30f | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | O=C1CCCc2cc(C3OCCO3)ccc21 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[C:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[c:3](:[c:4]):[c:5])-[O;H0;D2;+0:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-1 | 10 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.80 g (8.34 mmol) of a 1:5 mixture of 3,4-dihydro-4,4-dimethyl-7-acetyl-naphthalen-1(2H)-one (Compound D14a); and 3,4-dihydro-4,4-dimethyl-6-acetyl-naphthalen-1(2H)-one (Compound D14b) in 50 mL benzene was combined with 517.7 mg (8.34 mmol) of ethylene glycol and 20.0 mg (0.11 mmol) of p-toluenesulfonic ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccc2c(c1)CCCC2.C1COCO1 | HO- | C1=CC=CC=C1 | null | null | CC(=O)c1ccc2c(c1)C(C)(C)CCC2=O.OCCO>C1=CC=CC=C1>CC1(C)CCC(=O)c2ccc(C3(C)OCCO3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46f36199a03b442ba91746cd3e3add7b | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C3(C)OCCO3)ccc21>>CCOC(=O)CC1=CCC(C)(C)c2cc(C(C)=O)ccc21 | CC1(OCCO1)C=1C=C2C(CCC(C2=CC1)(CC(=O)OCC)O)(C)C.CC=1C=CC(=CC1)S(=O)(=O)O.O>>CC1(CC=C(C2=CC=C(C=C12)C(C)=O)CC(=O)OCC)C | O[C:7]1([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8][CH2:9][C:10]([CH3:11])([CH3:12])[c:13]2[cH:14][c:15]([C:16]3([CH3:17])OCC[O:18]3)[cH:19][cH:20][c:21]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1=[CH:8][CH2:9][C:10]([CH3:11])([CH3:12])[c:13]2[cH:14][c:15]([C:16]([CH3:17])=[O:18])[cH:19][cH:20][c:21]21 | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C3(C)OCCO3)ccc21 | CCOC(=O)CC1=CCC(C)(C)c2cc(C(C)=O)ccc21 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 9d4ab51434e135588277b1abca09c019ba592a5324ec3ef14e049c0ab80fdb7b | 443dac47cd5d45a6cddf21b9d72a18d45ad34952e38f4958ebce8b1ddd0eb30d | C1=Cc2ccccc2CC1 | O-[C;H0;D4;+0:1]1(-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH2;D2;+0:7]-[C:8]-[C:9]-[c:10]2:[c:11]:[c:12](-[C;H0;D4;+0:13]3(-[C;D1;H3:14])-O-C-C-[O;H0;D2;+0:15]-3):[c:16]:[c:17]:[c:18]:2-1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:7]-[C:8]-[C:9]-[c:10]2:[c:11]:[c:12](-[C;H0;D3;+0:13](-[C;D1;H3:... | null | [] | null | null | null | null | A solution of (±)6-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthlene ((Compound D16, 321 mg, 0.90 mmol) and catalytic amount of TsOH in 20 ml of benzene was refluxed for 12 h. During the reaction the water generated from the reaction was periodically removed by a De... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary alcohol | Ketone | c1ccc2c(c1)CCCC2.C1COCO1 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | C1=CC=CC=C1 | null | null | CCOC(=O)CC1(O)CCC(C)(C)c2cc(C3(C)OCCO3)ccc21>C1=CC=CC=C1>CCOC(=O)CC1=CCC(C)(C)c2cc(C(C)=O)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-130b3a00a9dc43f5a473799157e45ada | CC1(C)CCC(=O)c2ccccc21.CCOCC.[Li][C](C)(C)C>>CC(=O)c1ccc2c(c1)C(C)(C)CC=C2C(C)(C)C | O=S(Cl)Cl.CC1(CCC(C2=CC=CC=C12)=O)C.[Li]C(C)(C)C.CCOCC>>CC1(CC=C(C2=CC=C(C=C12)C(C)=O)C(C)(C)C)C | [O:3]=[C:15]1[c:7]2[cH:6][cH:5][cH:4][cH:9][c:8]2[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14]1.CCO[CH2:2][CH3:1].[Li][C:16]([CH3:17])([CH3:18])[CH3:19]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH:14]=[C:15]2[C:16]([CH3:17])([CH3:18])[CH3:19] | CC1(C)CCC(=O)c2ccccc21.CCOCC.[Li][C](C)(C)C | CC(=O)c1ccc2c(c1)C(C)(C)CC=C2C(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 2ea059215f3fee8060392dd5e073e50c86e682d9ccd36b54923fc97f9447780d | 2a55fa5b64016cbe1065d8e162e8394140e0c89b5a40b3ee805cb2dd6c82c75d | C1=Cc2ccccc2CC1 | C-C-O-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[Li].[O;H0;D1;+0:7]=[C;H0;D3;+0:8]1-[CH2;D2;+0:9]-[C:10]-[C:11]-[c:12]2:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16]:[c:17]:2-1>>[C;D1;H3:3]-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:8]1=[CH;D2;+0:9]-[C:10]-[C:11]-[c:12]2:[c:13]:[... | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of 6-(2-methyl-1,3-dioxolan-2-yl)!-3,4-dihydro-4,4-dimethylnaphthlen-1(2H)-one ((Compound D15, 353 mg, 1.36 mmol) in 3 ml of dry ether at -78° C. was added dropwise t-BuLi (1 ml, 1.7 mmol, 1.7M solution in pentane). This dear light yellow solution was left at -78° C. for 30 min. Then, fleshly distilled SO... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Alkyl lithium | Ketone | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO-.Li | null | -78 | 0.5 | CC1(C)CCC(=O)c2ccccc21.CCOCC.[Li][C](C)(C)C>>CC(=O)c1ccc2c(c1)C(C)(C)CC=C2C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-772b5fad62a14312b842257dffc914b5 | CC(=O)c1ccc2c(c1)C(C)(C)CC=C2c1cccs1.O=Cc1ccc(C(=O)O)cc1>>CC1(C)CC=C(c2cccs2)c2ccc(C(=O)C=Cc3ccc(C(=O)O)cc3)cc21 | S1C(=CC=C1)C1=CCC(C2=CC(=CC=C12)C(C)=O)(C)C.C(=O)(O)C1=CC=C(C=O)C=C1.[OH-].[Na+]>>O=C(C=CC1=CC=C(C(=O)O)C=C1)C1=CC=2C(CC=C(C2C=C1)C=1SC=CC1)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][cH:10][s:11]2)[c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[CH3:18])[cH:29][c:30]21.O=[CH:19][c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][cH:10][s:11]2)[c:12]2[cH:13][cH:14][c:1... | CC(=O)c1ccc2c(c1)C(C)(C)CC=C2c1cccs1.O=Cc1ccc(C(=O)O)cc1 | CC1(C)CC=C(c2cccs2)c2ccc(C(=O)C=Cc3ccc(C(=O)O)cc3)cc21 | null | null | CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1ccccc1)c1ccc2c(c1)CCC=C2c1cccs1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 12 | HOUR | To a solution of 62.6 mg (0.222 mmol) 3,4-dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene (Compound D33) in 4.0 mL of MeOH were added 33.4 mg (0.222 mmol) of 4-carboxy benzaldehyde, and 240.0 mg (6.00 mmol; 2.0 mL of 3M aqueous NaOH). The resulting solution was stirred at room temperature for 12 h, concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccsc1.C1=Cc2ccccc2CC1.c1ccccc1 | HO- | CO | null | 12 | CC(=O)c1ccc2c(c1)C(C)(C)CC=C2c1cccs1.O=Cc1ccc(C(=O)O)cc1>CO>CC1(C)CC=C(c2cccs2)c2ccc(C(=O)C=Cc3ccc(C(=O)O)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5f9f7585dafc4f17ad29c89236ac8a9d | COC(=O)c1ccc2c(c1)C(=O)CCC2(C)C>>CC1(C)CCC(=O)c2ccccc21 | CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C.CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C.[OH-].[Na+].Cl>>CC1(C=2C=CC=CC2C(CC1)=O)C | COC(=O)[c:10]1[cH:9][c:8]2[c:13]([cH:12][cH:11]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | COC(=O)c1ccc2c(c1)C(=O)CCC2(C)C | CC1(C)CCC(=O)c2ccccc21 | null | null | C(C)O.C1CCOC1 | Reduction | Decarboxylation | d6bbb76477b08de1e249c18973b19813a0f61a90fc74922e437d8dcd688d09f7 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=C1CCCc2ccccc21 | C-O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[O;D1;H0:7]>>[O;D1;H0:7]=[C:6]-[c:5]:[c:4]:[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | 16 | HOUR | To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 1.05 g, 4.5 mmol) in 10 mL of ethanol and THF (10 mL) was added sodiumhydroxide 9 mL (1M solution). The solution was stirred for 16 h and thereafter acidified with 10% HCl. The mixture was extracted with ethyl acetate, the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | C(C)O.C1CCOC1 | null | 16 | COC(=O)c1ccc2c(c1)C(=O)CCC2(C)C>C(C)O.C1CCOC1>CC1(C)CCC(=O)c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9c61c395e2c4475a549c72777a848f0 | COC(=O)c1ccc2c(c1)C(OS(=O)(=O)C(F)(F)F)=CCC2(C)C.c1ccsc1>>COC(=O)c1ccc2c(c1)C(c1cccs1)=CCC2(C)C | CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)C(=O)OC)C.CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)C(=O)OC)C.S1C=CC=C1.C(CCC)[Li]>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC)C | O=S(=O)(O[C:11]1=[CH:17][CH2:18][C:19]([CH3:20])([CH3:21])[c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10][c:9]21)C(F)(F)F.[cH:12]1[cH:13][cH:14][cH:15][s:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11]([c:12]1[cH:13][cH:14][cH:15][s:16]1)=[CH:17][CH2:18][C:19]2([CH3:20])[CH3:21] | COC(=O)c1ccc2c(c1)C(OS(=O)(=O)C(F)(F)F)=CCC2(C)C.c1ccsc1 | COC(=O)c1ccc2c(c1)C(c1cccs1)=CCC2(C)C | null | [Cl-].[Cl-].[Zn+2] | C1CCOC1 | C-C Coupling | OtherReaction | 1635e33838212f74c180ab5d22f02760affb57410f7f71f8f01e910656be3423 | 253c3b9fccee9bf420e0fb1f267e37bad5aa0c206427cb57447e420babcc09c8 | C1=C(c2cccs2)c2ccccc2CC1 | F-C(-F)(-F)-S(=O)(=O)-O-[C;H0;D3;+0:1](=[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[#16;a:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[C:3]-[C:2]=[C;H0;D3;+0:1](-[c;H0;D3;+0:11]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1)-[c:4](:[c:5]):[c:6] | 5 | [{"value": 5.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | (Compound E5) To a solution of 329.0 mg (3.93 mmol) of thiophene in 2.0 mL THF at 0° C. was added 251.8 mg (3.93 mmol, 1.56 mL of 2.5M solution in hexanes) of n-butyllithium. After stirring for 3 h at 0° C., a solution of 845.0 mg (6.28 mmol) of ZnCl2 in 5.0 mL THF was added and the resulting solution stirred for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | C1=Cc2ccccc2CC1.c1ccsc1 | c1ccsc1.C1=Cc2ccccc2CC1 | c1ccsc1.C1=Cc2ccccc2CC1 | TfOH.HO- | [Cl-].[Cl-].[Zn+2].C1CCOC1 | 0 | 3 | COC(=O)c1ccc2c(c1)C(OS(=O)(=O)C(F)(F)F)=CCC2(C)C.c1ccsc1>[Cl-].[Cl-].[Zn+2].C1CCOC1>COC(=O)c1ccc2c(c1)C(c1cccs1)=CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8760b059f5814b0b8512bcb8b33a9346 | COC(=O)c1ccc2c(c1)C(c1cccs1)=CCC2(C)C>>CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21 | CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC)C.CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC)C.[OH-].[Na+]>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)O)C | C[O:17][C:15]([c:14]1[cH:13][c:12]2[c:20]([cH:19][cH:18]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH:5]=[C:6]2[c:7]1[cH:8][cH:9][cH:10][s:11]1)=[O:16]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][cH:10][s:11]2)[c:12]2[cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19][c:20]21 | COC(=O)c1ccc2c(c1)C(c1cccs1)=CCC2(C)C | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21 | null | null | C1CCOC1.CCO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=C(c2cccs2)c2ccccc2CC1 | 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 | [] | 35 | CELSIUS | null | null | To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate (Compound E5, 430.0 mg, 1.44 mmol) in 3.0 mL of EtOH and 3.0 mL THF was added NaOH (240.0 mg, 6.00 mmol; 3.0 mL of a 2N aqueous solution). The resulting solution was warmed to 35° C. for 6 h, cooled to room temperature and quenched ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccsc1.C1=Cc2ccccc2CC1 | Other | C1CCOC1.CCO | 35 | null | COC(=O)c1ccc2c(c1)C(c1cccs1)=CCC2(C)C>C1CCOC1.CCO>CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-efe92404a0254b2b89ad1b766a802326 | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21.CCOC(=O)c1ccc(O)cc1>>CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1 | CCOC(=O)C.CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)O)C.CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)O)C.OC1=CC=C(C(=O)OCC)C=C1.Cl.CN(CCCN=C=NCC)C>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC1=CC=C(C(=O)OCC)C=C1)C | O[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[C:19]([c:20]1[cH:21][cH:22][cH:23][s:24]1)=[CH:25][CH2:26][C:27]2([CH3:28])[CH3:29].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][C:11](=[O:12])[c:13]2[cH:14][cH... | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21.CCOC(=O)c1ccc(O)cc1 | CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1 | null | null | CN(C)C=O | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Oc1ccccc1)c1ccc2c(c1)C(c1cccs1)=CCC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid (Compound E6, 50.0 mg, 0.177 mmol), ethyl 4-hydroxybenzoate (38.2 mg, 0.230 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (44.0 mg, 0.230 mmol), and 4-N,N-dimethylaminopyridine (28.0 mg, 0.230 mmol) in 2.0 mL DMF was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccsc1.C1=Cc2ccccc2CC1 | HO- | CN(C)C=O | null | null | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21.CCOC(=O)c1ccc(O)cc1>CN(C)C=O>CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(c2cccs2)=CCC3(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d50f3e28aedd4932b721cce8a6aefdfd | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21.C[Si](C)(C)CCOC(=O)c1ccc(O)cc1>>CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 | CCOCC.CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)O)C.CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)O)C.OC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1.Cl.CN(CCCN=C=NCC)C>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)C | O[C:15]([c:14]1[cH:13][c:12]2[c:35]([cH:34][cH:33]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH:5]=[C:6]2[c:7]1[cH:8][cH:9][cH:10][s:11]1)=[O:16].[OH:17][c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[cH:31][cH:32]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9... | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21.C[Si](C)(C)CCOC(=O)c1ccc(O)cc1 | CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 | null | null | CN(C)C=O | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Oc1ccccc1)c1ccc2c(c1)C(c1cccs1)=CCC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid (Compound E6, 79.0 mg, 0.280 mmol), 2-trimethylsilylethyl 4-hydroxybenzoate (73.3 mg, 0.308 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (70.0 mg, 0.364 mmol), and 4-N,N-dimethylaminopyridine (44.5 mg, 0.364 mmol) i... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccsc1.C1=Cc2ccccc2CC1.c1ccccc1 | HO- | CN(C)C=O | null | null | CC1(C)CC=C(c2cccs2)c2cc(C(=O)O)ccc21.C[Si](C)(C)CCOC(=O)c1ccc(O)cc1>CN(C)C=O>CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54921a0488e14a3e81bfab9c9a8565e8 | CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21>>CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc21 | CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)C(=O)OC1=CC=C(C(=O)O)C=C1)C | C[Si](C)(C)CC[O:24][C:22]([c:21]1[cH:20][cH:19][c:18]([O:17][C:15]([c:14]2[cH:13][c:12]3[c:29]([cH:28][cH:27]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH:5]=[C:6]3[c:7]2[cH:8][cH:9][cH:10][s:11]2)=[O:16])[cH:26][cH:25]1)=[O:23]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][cH:10][s:11]2)[c:12]2[cH:13][c:14]([C:1... | CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21 | CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc21 | null | null | C1CCOC1.CCOC(=O)C | Deprotection | Ester saponification (alkyl deprotection) | a3c1e490feb6b7fce3c6323047260c78ad5d894f96ffb52fbe21f86a88668678 | 5b01c4b72bcb1d31e02ab060e26bc1888b853fee0b286003b9b19e22cf024145 | O=C(Oc1ccccc1)c1ccc2c(c1)C(c1cccs1)=CCC2 | C-[Si](-C)(-C)-C-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 | 8 | HOUR | To a solution of 2-trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate (Compound E10, 100.0 mg, 0.198 mmol) in 2.0 mL THF at room temperature was added 155.3 mg of tetrabutylammonium fluoride (0.594 mmol 0.6 mL of a 1M solution in THF). After stirring overnight the rea... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Silyl protective group | Carboxylic acid | null | null | c1ccsc1.C1=Cc2ccccc2CC1.c1ccccc1 | Other | C1CCOC1.CCOC(=O)C | null | 8 | CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21>C1CCOC1.CCOC(=O)C>CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83bf3c1c076c4485b404b1a77f65cfe6 | COC(=O)c1ccc2c(c1)C(=O)CCC2(C)C.Sc1ccccc1>>COC(=O)c1ccc2c(c1)C(Sc1ccccc1)=CCC2(C)C | C1(=CC=CC=C1)S.CCN(CC)CC.CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C.CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C.O>>COC(=O)C1=CC=2C(=CCC(C2C=C1)(C)C)SC1=CC=CC=C1 | O=[C:11]1[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[C:21]([CH3:22])([CH3:23])[CH2:20][CH2:19]1.[SH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11]([S:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[CH:19][CH2:20][C:21]2([CH3:... | COC(=O)c1ccc2c(c1)C(=O)CCC2(C)C.Sc1ccccc1 | COC(=O)c1ccc2c(c1)C(Sc1ccccc1)=CCC2(C)C | null | Cl[Ti](Cl)(Cl)Cl | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0ada3ae671ad3b060b96add65fbcfec1b731cae0a6c858eea87374516a4ac73a | f936d6b76ed560a8fec322bcfbbde18f0a579df08bd9baf16a1cafcec3158898 | C1=C(Sc2ccccc2)c2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:7]:[c:6]1:[c:5]-[C:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1]-1-[S;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 835.0 mg, 3.60 mmol) in 25.0 mL of THF at room temperature was added TiCl4 (670.0 mg, 3.55 mmol). Thereafter a solution of thiophenol (430.0 mg, 3.90 mmol) and Et3N (730.0 mg, 7.20 mmol) in 10 mL THF was added. The resulti... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic thiol | Monosulfide | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | c1ccccc1.C1=Cc2ccccc2CC1 | HO- | Cl[Ti](Cl)(Cl)Cl.C1CCOC1 | null | null | COC(=O)c1ccc2c(c1)C(=O)CCC2(C)C.Sc1ccccc1>Cl[Ti](Cl)(Cl)Cl.C1CCOC1>COC(=O)c1ccc2c(c1)C(Sc1ccccc1)=CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e3e7b7ca98e641d6a2d408b95787c8d2 | COC(=O)c1ccc2c(c1)C(Sc1ccccc1)=CCC2(C)C>>CC1(C)CC=C(Sc2ccccc2)c2cc(C(=O)O)ccc21 | CC1(C=2C=CC(=CC2C(=CC1)SC1=CC=CC=C1)C(=O)OC)C.CC1(C=2C=CC(=CC2C(=CC1)SC1=CC=CC=C1)C(=O)OC)C.[OH-].[Na+]>>CC1(C=2C=CC(=CC2C(=CC1)SC1=CC=CC=C1)C(=O)O)C | C[O:19][C:17]([c:16]1[cH:15][c:14]2[c:22]([cH:21][cH:20]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH:5]=[C:6]2[S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:18]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH:5]=[C:6]([S:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]21 | COC(=O)c1ccc2c(c1)C(Sc1ccccc1)=CCC2(C)C | CC1(C)CC=C(Sc2ccccc2)c2cc(C(=O)O)ccc21 | null | null | C1CCOC1.CCO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=C(Sc2ccccc2)c2ccccc2CC1 | 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 | 8 | HOUR | To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate (Compound E18, 300.0 mg, 0.926 mmol) in 4.0 mL of EtOH and 2.0 mL THF was added NaOH (200.0 mg, 5.00 mmol; 5.0 mL of a 1N aqueous solution). After stirring overnight at room temperature the reaction was quenched by the addition of... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1=Cc2ccccc2CC1 | Other | C1CCOC1.CCO | null | 8 | COC(=O)c1ccc2c(c1)C(Sc1ccccc1)=CCC2(C)C>C1CCOC1.CCO>CC1(C)CC=C(Sc2ccccc2)c2cc(C(=O)O)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf2e44a5bdea4415bef84fd79bdef046 | CC1(C)CCC(=O)c2cc(Br)ccc21.CCOC(=O)CBr>>CCOC(=O)CC1(O)CCC(C)(C)c2ccc(Br)cc21 | BrCC(=O)OCC.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C.BrC1=CC=C2C(CCC(C2=C1)=O)(C)C>>OC1(CCC(C2=CC=C(C=C12)Br)(C)C)CC(=O)OCC | [C:7]1(=[O:8])[CH2:9][CH2:10][C:11]([CH3:12])([CH3:13])[c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]21.Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1([OH:8])[CH2:9][CH2:10][C:11]([CH3:12])([CH3:13])[c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]21 | CC1(C)CCC(=O)c2cc(Br)ccc21.CCOC(=O)CBr | CCOC(=O)CC1(O)CCC(C)(C)c2ccc(Br)cc21 | null | [Zn] | C1=CC=CC=C1 | C-C Coupling | Grignard_alcohol | ae6802bc43630c235b581c1f69ee3f400dd59564bb5948df811879329723b99c | 86d8e63c1eeb9e82c583fd2409352b28a569a3f780f9f297e86b8d2f688ca9d6 | c1ccc2c(c1)CCCC2 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7]-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | To a suspension of Zn (1.20 g, 18.4 mmol) in 10 mL benzene at 100° C. was slowly added a solution of ethyl 2-bromoacetate (658.0 mg, 3.94 mmol) and 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G, 500.0 mg, 1.97 mmol) in 20.0 mL benzene. The resulting mixture was heated for 2 h, cooled to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ester.Tertiary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Br- | [Zn].C1=CC=CC=C1 | null | null | CC1(C)CCC(=O)c2cc(Br)ccc21.CCOC(=O)CBr>[Zn].C1=CC=CC=C1>CCOC(=O)CC1(O)CCC(C)(C)c2ccc(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ecb612d8d5a4573ace4ca6045265aad | CC(=O)OC(C)=O.CCOC(=O)CC1(O)CCC(C)(C)c2ccc(Br)cc21>>CCOC(=O)CC1(OC(C)=O)CCC(C)(C)c2ccc(Br)cc21 | OC1(CCC(C2=CC=C(C=C12)Br)(C)C)CC(=O)OCC.C(C)(=O)OC(C)=O>>C(C)(=O)OC1(CCC(C2=CC=C(C=C12)Br)(C)C)CC(=O)OCC | CC(=O)O[C:9]([CH3:10])=[O:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1([OH:8])[CH2:12][CH2:13][C:14]([CH3:15])([CH3:16])[c:17]2[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1([O:8][C:9]([CH3:10])=[O:11])[CH2:12][CH2:13][C:14]([CH3:15])([CH3:16])[c:17]2[cH:18][cH:19][c:20... | CC(=O)OC(C)=O.CCOC(=O)CC1(O)CCC(C)(C)c2ccc(Br)cc21 | CCOC(=O)CC1(OC(C)=O)CCC(C)(C)c2ccc(Br)cc21 | null | null | CCOC(=O)C.C(Cl)Cl | Acylation | Transesterification | 7845e6caeb9ebcfc4e11ccde0ca862e171727c1b0b0f5c55f250826811ed7095 | aad6c0b0b2e56c19696d13bcd56b340e680e45229f4a56b765d97baaf778738e | c1ccc2c(c1)CCCC2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8](-[OH;D1;+0:9])(-[C:10])-[c:11]>>[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])(-[C:10])-[c:11] | null | [] | null | null | 8 | HOUR | To a solution of (±)ethyl 2-(1-hydroxy-1,2,3,4-tetrahydro-4,4-dimethyl-7-bromo-naphthalen-1-yl)acetate (Compound E47, 200.0 mg, 0.586 mmol) and 4-N,N-dimethylaminopyridine (86.0 mg, 0.703 mmol) in 4.0 mL CH2Cl2 at 0° C. was added acetic anhydride (239.3 mg, 2.344 mmol). The resulting solution was warmed to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Tertiary alcohol | Ester | null | null | c1ccc2c(c1)CCCC2 | HO- | CCOC(=O)C.C(Cl)Cl | null | 8 | CC(=O)OC(C)=O.CCOC(=O)CC1(O)CCC(C)(C)c2ccc(Br)cc21>CCOC(=O)C.C(Cl)Cl>CCOC(=O)CC1(OC(C)=O)CCC(C)(C)c2ccc(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f22788fdfdc049bab420209786ecbc6d | CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(O)(C(=O)OCC)CCC3(C)C)cc1>>CCOC(=O)C1=CCC(C)(C)c2ccc(C(=O)Oc3ccc(C(=O)OCC)cc3)cc21 | CC1(C=2C=CC(=CC2C(CC1)(C(=O)OCC)O)C(=O)OC1=CC=C(C(=O)OCC)C=C1)C.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1(C=2C=CC(=CC2C(=CC1)C(=O)OCC)C(=O)OC1=CC=C(C(=O)OCC)C=C1)C | O[C:6]1([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][c:19]3[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH2:26][CH3:27])[cH:28][cH:29]3)[cH:30][c:31]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]2[cH:13][... | CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(O)(C(=O)OCC)CCC3(C)C)cc1 | CCOC(=O)C1=CCC(C)(C)c2ccc(C(=O)Oc3ccc(C(=O)OCC)cc3)cc21 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 0d4902b4a0354b39eb06a3aca835d99df3984d26d91039f7ea7b84a4d6ff29ff | 694c4e8841d135e88d9ce8d5ff0cd8a883ffff2e7714effccf3da6c8a7d1d0fb | O=C(Oc1ccccc1)c1ccc2c(c1)C=CCC2 | O-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[CH2;D2;+0:6]-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[C;H0;D3;+0:1]1=[CH;D2;+0:6]-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11] | 10 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (±)ethyl 4-[[(5,5-dimethyl-8-hydroxy-8-(carbethoxy)-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]oxy]benzoate (Compound E54, 35.0 mg, 0.077 mmol) in 10 mL benzene was added a catalytic amount (approximately 2 mg) of p-toluenesulfonic acid monohydrate. The solution was heated to reflux under a Dean-Stark ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary alcohol | Ester | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | 8 | CCOC(=O)c1ccc(OC(=O)c2ccc3c(c2)C(O)(C(=O)OCC)CCC3(C)C)cc1>C1=CC=CC=C1>CCOC(=O)C1=CCC(C)(C)c2ccc(C(=O)Oc3ccc(C(=O)OCC)cc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-453ce30ee5274954b0f4cd3bf04e1207 | CC1(C)CCC(=O)c2cc(C(=O)O)ccc21.CC1(C)CCC(=O)c2cc(C(=O)O)ccc21.CCOC(C)=O.CN(C)c1ccccn1>>CC1(C)CCC(=O)c2cc(C(=O)Oc3ccc(C(=O)OCc4ccccc4)cc3)ccc21 | CN(C)C1=NC=CC=C1.C(C)(=O)OCC.CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)O)C.CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)O)C>>C(C1=CC=CC=C1)OC(C1=CC=C(C=C1)OC(=O)C1=CC=2C(CCC(C2C=C1)(C)C)=O)=O | CC1(C)CCC(=O)[c:15]2[c:14]1[cH:29][cH:28][c:17]([C:18](=[O:19])[OH:20])[cH:16]2.[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:30][cH:31][c:32]21.CC(=O)O[CH2:21][CH3:27].CN(C)[c:22]1n[cH:26][cH:25][cH:24][cH:23]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[cH... | CC1(C)CCC(=O)c2cc(C(=O)O)ccc21.CC1(C)CCC(=O)c2cc(C(=O)O)ccc21.CCOC(C)=O.CN(C)c1ccccn1 | CC1(C)CCC(=O)c2cc(C(=O)Oc3ccc(C(=O)OCc4ccccc4)cc3)ccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b8e18650f2f7b7caf5929c1531b8dd577696d464ec72569f4ab2648f973f63cd | c97b5103fb5809046a98660f39dac8bdf0ef3933daf7a854242cffd272e2b30b | O=C(OCc1ccccc1)c1ccc(OC(=O)c2ccc3c(c2)C(=O)CCC3)cc1 | C-C(=O)-O-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-C1(-C)-C-C-C(=O)-[c;H0;D3;+0:3]2:[c:4]:[c:5](-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:9]:[c:10]:[c;H0;D3;+0:11]:2-1.C-N(-C)-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:n:1.[O;D1;H0:17]=[C:18](-[OH;D1;+0:19])-[c:20]>>[O;D1;H0:17]=[C:18](-[c:20])-[O;H0;D2;+0:19]-[c;H0;D3;+0:11... | null | [] | null | null | 10 | MINUTE | To a solution of 5,5-dimethyl-5,6,7,8-tetrahydro-8-oxo-naphthalen-2-carboxylic acid (Compound E3, 386 mg, 1.77 mmol) in dimethylformamide (4 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarboimide hydrochloride (440 mg, 2.3 mmol) followed by dimethylamino pyridine (DMAP) (280 mg, 2.3 mmol). The mixture was stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ketone.Ester.Tertiary amine | Ester.Ester | c1ccc2c(c1)CCCC2.c1ccncc1 | c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCC2.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | 0.166667 | CC1(C)CCC(=O)c2cc(C(=O)O)ccc21.CC1(C)CCC(=O)c2cc(C(=O)O)ccc21.CCOC(C)=O.CN(C)c1ccccn1>CN(C=O)C>CC1(C)CCC(=O)c2cc(C(=O)Oc3ccc(C(=O)OCc4ccccc4)cc3)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4fb35b7c4bda4aad9a8f5688f126c64d | C=CN1CCCC1=O>>C=CN1CCCC1=O | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(C(=C)C)(=O)OCCCCCCCCCCCC.C(=C)N1C(CCC1)=O.N(=NC(C#N)(C)C)C(C#N)(C)C.C(=C)N1C(CCC1)=O.C(C(=C)C)(=O)OCCCCCCCCCCCC>>C(C(=C)C)(=O)OCCCCCCCCCCCC.C(=C)N1C(CCC1)=O | [CH2:19]=[CH:20][N:21]1[CH2:22][CH2:23][CH2:24][C:25]1=[O:26]>>[CH2:19]=[CH:20][N:21]1[CH2:22][CH2:23][CH2:24][C:25]1=[O:26] | C=CN1CCCC1=O | C=CN1CCCC1=O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCCN1 | null | null | [] | 30 | CELSIUS | 10 | MINUTE | A solution of 95 parts by weight of lauryl methacrylate in 200 parts by weight of IP Solvent 1620 (produced by Idemitsu Petrochemical Co., Ltd.) is prepared. Argon gas is blown into the solution for 10 minutes to displace the gas entrained in the entire reaction system with argon gas. Then, benzoyl peroxide is added as... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1 | null | null | 30 | 0.166667 | C=CN1CCCC1=O>>C=CN1CCCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-62dac6c13c4c4aa59ca7877a94095e3c | CCCCC[Si@@H]1CC[C@@H](CC(O)C#Cc2ccc(F)cc2)CC1>>CCCCC[Si@@H]1CC[C@@H](/C=C/C#Cc2ccc(F)cc2)CC1 | FC1=CC=C(C=C1)C#CC(C[C@@H]1CC[Si@H](CC1)CCCCC)O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=CC=C(C=C1)C#C\C=C\[C@@H]1CC[Si@H](CC1)CCCCC | O[CH:11]([CH2:10][C@H:9]1[CH2:8][CH2:7][Si@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:22][CH2:21]1)[C:12]#[C:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][Si@H:6]1[CH2:7][CH2:8][C@H:9](/[CH:10]=[CH:11]/[C:12]#[C:13][c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:2... | CCCCC[Si@@H]1CC[C@@H](CC(O)C#Cc2ccc(F)cc2)CC1 | CCCCC[Si@@H]1CC[C@@H](/C=C/C#Cc2ccc(F)cc2)CC1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 24323612d5486e9fd0704523d3a93bd4db9c6e3295677a91ceb1aea86b497d01 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | C(#Cc1ccccc1)/C=C/C1CC[SiH2]CC1 | O-[CH;D3;+0:1](-[C:2]#[C:3]-[c:4])-[CH2;D2;+0:5]-[C:6](-[C:7])-[C:8]>>[C:7]-[C:6](/[CH;D2;+0:5]=[CH;D2;+0:1]/[C:2]#[C:3]-[c:4])-[C:8] | 15.9 | [{"value": 15.9, "product": "FC1=CC=C(C=C1)C#C\\C=C\\[C@@H]1CC[Si@H](CC1)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "FC1=CC=C(C=C1)C#C\\C=C\\[C@@H]1CC[Si@H](CC1)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(4-fluorophenyl)-4-(trans-4-pentyl-4-silacyclohexyl)-1-butyne-3-ol 8.0 g (24 mmol), p-toluenesulfonic acid monohydrate 1.6 g, and benzene 200 ml was heated under reflux to remove the water and then subjected to a conventional post-treatment. The reaction mixture thus obtained was not only a mixture of tr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | C1CC[SiH]CC1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | null | CCCCC[Si@@H]1CC[C@@H](CC(O)C#Cc2ccc(F)cc2)CC1>C1=CC=CC=C1>CCCCC[Si@@H]1CC[C@@H](/C=C/C#Cc2ccc(F)cc2)CC1 |
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