dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af31012b08574561a1c9a10811e4bf9f | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.COC(=O)C(CN)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.C(C)(C)(C)C=1C=C2C(C(=O)OC2=O)=CC1>>C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][c:19]2[C:20]1=[O:21].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:22]1([CH3:23])[O:24][CH2:25][CH2:26][O:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:1... | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.COC(=O)C(CN)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5-t-butyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.14 g, 14%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.50 g, 2.64 mmol) and 4-t-butylphthalic anhydride (0.70 g, 3.43 mmol), ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.COC(=O)C(CN)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d9bd298abef4d1a8592a82a173535b8 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(O)cccc21>>COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.OC1=C2C(C(=O)OC2=O)=CC=C1>>OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([OH:15])[c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([OH:15])[c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:21... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(O)cccc21 | COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.84 g, 45%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (1.00 g, 5.54 mmol) and 3-hydroxyphthalic anhydride (1.00 g, 6.09 mmol), ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(O)cccc21>>COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54daba3da7de46289f7ac27c43312a51 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21>>COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.ClC1=C2C(C(=O)OC2=O)=C(C=C1)Cl>>ClC1=C2C(N(C(C2=C(C=C1)Cl)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:8](=[O:9])[c:10]2[c:11]([Cl:12])[cH:13][cH:14][c:15]([Cl:16])[c:17]2[C:18]1=[O:19]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[c:11]([Cl:12])[cH:13][cH:14][c:15]([Cl:16])[c:17]2[C:18]1=[O:19])[C:20]... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21 | COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.23 g, 30%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 2.30 mmol) and 3,6-dichlorophthalic anhydride (0.50 g, 2.30 m... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21>>COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4eeb9803d7254579bb51be4e9a23faa9 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21>>COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.ClC=1C=C2C(C(=O)OC2=O)=CC1Cl>>ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:8](=[O:9])[c:10]2[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21 | COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.42 g, 39%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.50 g, 2.64 mmol) and 4,5-dichlorophthalic anhydride (0.80 g, 3.64 m... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21>>COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f6ca9e302e948e0bf4ab1d4a60676d4 | COC(=O)C(CN)C1(C)OCCO1.O=C1C=C(c2ccccc2)C(=O)O1>>COC(=O)C(CN1C(=O)C=C(c2ccccc2)C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.C1(=CC=CC=C1)/C=1/C(=O)OC(\C1)=O>>O=C1N(C(C=C1C1=CC=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:8](=[O:9])[CH:10]=[C:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18]1=[O:19]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[CH:10]=[C:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18]1=[O:19])[C:2... | COC(=O)C(CN)C1(C)OCCO1.O=C1C=C(c2ccccc2)C(=O)O1 | COC(=O)C(CN1C(=O)C=C(c2ccccc2)C1=O)C1(C)OCCO1 | null | null | null | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=C(c2ccccc2)C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]=[C:12]-1-[c:13]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[C:12](-[c:13])=[C:11]-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(2,5-dioxo-3-phenyl-2,5-dihydro-pyrrol-1-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (1.0 g, 56%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (1.00 g, 5.29 mmol) and phenylmaleic anhydride (1.10 g, 6.34 mmol), and the o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccccc1.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1C=C(c2ccccc2)C(=O)O1>>COC(=O)C(CN1C(=O)C=C(c2ccccc2)C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-128369000365468e8ac4191f5ff6d728 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(F)ccc21>>COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.FC=1C=C2C(C(=O)OC2=O)=CC1>>FC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:21][... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(F)ccc21 | COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.66 g, 47%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 5.07 mmol) and 4-fluorophthalic anhydride (0.80 g, 5.07 mmol), an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(F)ccc21>>COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba36ac71896c4e299590b9da60b729a0 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)ccc21>>COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.ClC=1C=C2C(C(=O)OC2=O)=CC1>>ClC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:21... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)ccc21 | COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.54 g, 73%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 2.11 mmol) and 4-chlorophthalic anhydride (0.50 g, 2.74 mmol), an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)ccc21>>COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0aca16acb83b4339af15f31b931fbbf8 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Br)ccc21>>COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.BrC=1C=C2C(C(=O)OC2=O)=CC1>>BrC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:21... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Br)ccc21 | COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.48 g, 57 mmol) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.62 g, 2.75 mmol) and 4-bromophthalic anhydride (0.62 g, 2.75 mmol), ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Br)ccc21>>COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-507b77cf8a6148b682e37f9d01ce208c | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1ccc1ccccc21>>COC(=O)C(CN1C(=O)c2ccc3ccccc3c2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.C1=CC=C2C(=C1)C=CC3=C2C(=O)OC3=O>>O=C1N(C(C=2C=CC3=C(C12)C=CC=C3)=O)CC(C(=O)OC)C3(OCCO3)C | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:22]1([CH3:23])[O:24][CH2:25][CH2:26][O:27]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]2[C:20]1=[O:21]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:1... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1ccc1ccccc21 | COC(=O)C(CN1C(=O)c2ccc3ccccc3c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | 7c75a11b07ca67b4445d3306ca6d5d55860988fcd49e2187d1e057a7bf0214e0 | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccc3ccccc3c2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(1,3-dioxo-1,3-dihydro-benzo[e]isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.45 g, 58%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 2.11 mmol) and 1,2-naphthalic anhydride (0.55 g, 2.75 mmol), and t... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c3c(ccc2c1)COC3 | c1ccc2c3c(ccc2c1)C[NH]C3 | c1ccc2c3c(ccc2c1)C[NH]C3.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1ccc1ccccc21>>COC(=O)C(CN1C(=O)c2ccc3ccccc3c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-803be0e00f494b65b61925570b396a30 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>>CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.[N+](=O)([O-])C=1C=C2C(C(=O)OC2=O)=CC1>>[N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:22]1([CH3:23])[O:24][CH2:25][CH2:26][O:27]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]2[C:20]1=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21 | CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 | null | null | C(Cl)(Cl)Cl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | 83.2 | [{"value": 83.0, "product": "[N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.2, "product": "[N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (800 mg, 3.94 mmol) was dissolved in 15 mL of chloroform, and 4-nitrophthalic anhydride (988 mg, 4.33 mmol) was added to the obtained solution. The resulting mixture was then refluxed at 80° C. for 5 days. After the reaction was completed, the solvent was evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | C(Cl)(Cl)Cl | 80 | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>C(Cl)(Cl)Cl>CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03ceec0af51845ab888e49764d0f39ed | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21>>CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.FC1=C2C(C(=O)OC2=O)=CC=C1>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]1=[O:19])[C:20]1(... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21 | CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.25 g, 28%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.50 g, 2.64 mmol) and 3-fluorophthalic anhydride (0.57 g, 3.43 mmol), and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21>>CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54c317bf5f6643cd8f51c9f73264cc75 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)ccc(F)c21>>CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.FC1=C2C(C(=O)OC2=O)=C(C=C1)F>>FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:9](=[O:10])[c:11]2[c:12]([F:13])[cH:14][cH:15][c:16]([F:17])[c:18]2[C:19]1=[O:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[c:12]([F:13])[cH:14][cH:15][c:16]([F:17])[c:18]2[C:19]1=[... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)ccc(F)c21 | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 3.94 mmol) and 3,6-difluorophthalic anhydride (0.94 g, 4.33 mmol), and the o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)ccc(F)c21>>CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8f84cf070604788a184785d3e608165 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1cccc2[N+](=O)[O-]>>CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.[N+](=O)([O-])C1=C2C(C(=O)OC2=O)=CC=C1>>[N+](=O)([O-])C1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:22]1([CH3:23])[O:24][CH2:25][CH2:26][O:27]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]2[C:20]1=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1cccc2[N+](=O)[O-] | CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.64 g, 51%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.68 g, 3.34 mmol) and 3-nitrophthalic anhydride (0.84 g, 4.33 mmol), and t... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1cccc2[N+](=O)[O-]>>CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d050367120a4dafa8c3c812b63dbc82 | CCOC(=O)C(CN)C1(C)OCCO1.Cc1cccc2c1C(=O)OC2=O>>CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.CC1=C2C(C(=O)OC2=O)=CC=C1>>CC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([CH3:16])[c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([CH3:16])[c:17]2[C:18]1=[O:19])[C:2... | CCOC(=O)C(CN)C1(C)OCCO1.Cc1cccc2c1C(=O)OC2=O | CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(4-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.57 g, 76%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.60 g, 3.25 mmol) and 3-methylphthalic anhydride (0.79 g, 4.87 mmol), and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.Cc1cccc2c1C(=O)OC2=O>>CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd672a05df5a4c7da2b20b10ff055803 | CCOC(=O)C(CN)C1(C)OCCO1.Cc1ccc2c(c1)C(=O)OC2=O>>CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.CC=1C=C2C(C(=O)OC2=O)=CC1>>CC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][c:17]2[C:18]1=[O:19])[C:2... | CCOC(=O)C(CN)C1(C)OCCO1.Cc1ccc2c(c1)C(=O)OC2=O | CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(5-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.38 g, 40%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.60 g, 3.25 mmol) and 4-methylphthalic anhydride (0.79 g, 4.87 mmol), and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.Cc1ccc2c(c1)C(=O)OC2=O>>CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-552804aa978c4ce39582b3320065a2ad | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.CCOC(=O)C(CN)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.C(C)(C)(C)C=1C=C2C(C(=O)OC2=O)=CC1>>C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]2[C:21]1=[O:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:23]1([CH3:24])[O:25][CH2:26][CH2:27][O:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([C:15]([CH3:16])... | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.CCOC(=O)C(CN)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(5-t-butyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.54 g, 35%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 3.94 mmol) and 4-t-butylphthalic anhydride (0.88 g, 4.33 mmol), a... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.CCOC(=O)C(CN)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-958756ffd18845888710f0970aeb4d2c | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(O)cccc21>>CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.OC1=C2C(C(=O)OC2=O)=CC=C1>>OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]2[C:18]1=[O:19])[C:20]... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(O)cccc21 | CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.46 g, 67%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 1.96 mmol) and 3-hydroxyphthalic anhydride (0.42 g, 2.16 mmol), a... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(O)cccc21>>CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa18f1214ee14dfda574447a07657dad | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21>>CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.ClC1=C2C(C(=O)OC2=O)=C(C=C1)Cl>>ClC1=C2C(N(C(C2=C(C=C1)Cl)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][cH:15][c:16]([Cl:17])[c:18]2[C:19]1=[O:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][cH:15][c:16]([Cl:17])[c:18]2[C:19... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21 | CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (1.10 g, 74%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 3.94 mmol) and 3,6-dichlorophthalic anhydride (0.94 g, 4.33 mm... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21>>CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b65c8bbe15784ca3b285bbca9b865f1d | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21>>CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.ClC=1C=C2C(C(=O)OC2=O)=CC1Cl>>ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:9](=[O:10])[c:11]2[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]2[C:19]1=[O:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]2[C:19... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21 | CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.66 g, 50%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.60 g, 3.25 mmol) and 4,5-dichlorophthalic anhydride (0.85 g, 3.90 mm... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21>>CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62631dd2405c45b2ad8f5dbb8fd5e602 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)C2=C1CCCC2>>CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.C1(C2=C(C(=O)O1)CCCC2)=O>>O=C1N(C(C=2CCCCC12)=O)CC(C(=O)OCC)C1(OCCO1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:9](=[O:10])[C:11]2=[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17]1=[O:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[C:11]2=[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17]1=[O:18])[C:19]1(... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)C2=C1CCCC2 | CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C1(C)OCCO1 | null | null | null | Acylation | OtherReaction | e8011a3b0be1a45acf4cbe99b6add2c178c54f184ca2415e1c1cb07e7aee07ff | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2=C(CCCC2)C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[C:7]-[C:8]1=[C:9](-[C:10])-[C;H0;D3;+0:11](=[O;D1;H0:12])-O-[C;H0;D3;+0:13]-1=[O;D1;H0:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:13](=[O;D1;H0:14])-[C:8](=[C:9](-[C:10])-[C;H0;D3;+0:11]-1=[O;D1;H0:12])-[C:7] | null | [] | null | null | null | null | Ethyl 3-(1,3-dioxo-1,3,4,5,6,7-hexahydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.91 g, 69%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 3.94 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (0.78 g, 4.33... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CCC2=C(C1)COC2 | C1CCC2=C(C1)C[NH]C2 | C1CCC2=C(C1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)C2=C1CCCC2>>CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-add2ac49407c438e8ea33308f273e188 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1C=C(c2ccccc2)C(=O)O1>>CCOC(=O)C(CN1C(=O)C=C(c2ccccc2)C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.C1(=CC=CC=C1)/C=1/C(=O)OC(\C1)=O>>O=C1N(C(C=C1C1=CC=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:9](=[O:10])[CH:11]=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C:19]1=[O:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[CH:11]=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C:... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1C=C(c2ccccc2)C(=O)O1 | CCOC(=O)C(CN1C(=O)C=C(c2ccccc2)C1=O)C1(C)OCCO1 | null | null | null | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=C(c2ccccc2)C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[c:12])=[C:13]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[c:12])=[C:13]-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(2,5-dioxo-3-phenyl-2,5-dihydro-pyrrol-1-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.41 g, 58%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 1.96 mmol) and phenylmaleic anhydride (0.57 g, 2.16 mmol), and the o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccccc1.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1C=C(c2ccccc2)C(=O)O1>>CCOC(=O)C(CN1C(=O)C=C(c2ccccc2)C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06ae0656ad3549c789a8f7bfef960b25 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(F)ccc21>>CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.FC=1C=C2C(C(=O)OC2=O)=CC1>>FC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]1(... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(F)ccc21 | CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.77 g, 56%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 3.94 mmol) and 4-fluorophthalic anhydride (0.78 g, 4.72 mmol), and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(F)ccc21>>CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0bbbc01340ee40928ac299d561b6d223 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)ccc21>>CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.ClC=1C=C2C(C(=O)OC2=O)=CC1>>ClC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)ccc21 | CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.37 g, 50%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 1.97 mmol) and 4-chlorophthalic anhydride (0.47 g, 2.56 mmol), and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Cl)ccc21>>CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4540155d90c04f88aab8dc893bf4fe03 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Br)ccc21>>CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.BrC=1C=C2C(C(=O)OC2=O)=CC1>>BrC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Br)ccc21 | CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.42 g, 52%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 1.97 mmol) and 4-bromophthalic anhydride (0.58 g, 2.56 mmol), and t... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc(Br)ccc21>>CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8581dabe000a4ae7832a590adb4022f8 | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1ccc1ccccc21>>CCOC(=O)C(CN1C(=O)c2ccc3ccccc3c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC)C1(OCCO1)C.C1=CC=C2C(=C1)C=CC3=C2C(=O)OC3=O>>O=C1N(C(C=2C=CC3=C(C12)C=CC=C3)=O)CC(C(=O)OCC)C3(OCCO3)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][NH2:8])[C:23]1([CH3:24])[O:25][CH2:26][CH2:27][O:28]1.O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[c:20]2[C:21]1=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][c... | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1ccc1ccccc21 | CCOC(=O)C(CN1C(=O)c2ccc3ccccc3c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | 7c75a11b07ca67b4445d3306ca6d5d55860988fcd49e2187d1e057a7bf0214e0 | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccc3ccccc3c2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](:[c:14])-[C;H0;D3;+0:8]-1=[O;D1;H0:7] | null | [] | null | null | null | null | Ethyl 3-(1,3-dioxo-1,3-dihydro-benzo[e]isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.55 g, 73%) in the same manner as described in the above example 5 (20) from ethyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.40 g, 1.97 mmol) and 1,2-naphthalic anhydride (0.51 g, 2.56 mmol), and th... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c3c(ccc2c1)COC3 | c1ccc2c3c(ccc2c1)C[NH]C3 | c1ccc2c3c(ccc2c1)C[NH]C3.C1COCO1 | HO- | null | null | null | CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1ccc1ccccc21>>CCOC(=O)C(CN1C(=O)c2ccc3ccccc3c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8a25e85c5804342b5d24a98cbc5cbf2 | C=CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21>>C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OCC=C)C1(OCCO1)C.FC1=C2C(C(=O)OC2=O)=CC=C1>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC=C)C1(OCCO1)C)=O | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH:7]([CH2:8][NH2:9])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]2[C:19]1=[O:20]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH:7]([CH2:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]2[C:19]1... | C=CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21 | C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | null | null | C(Cl)(Cl)Cl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | 52 | [{"value": 52.0, "product": "FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC=C)C1(OCCO1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC=C)C1(OCCO1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Allyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (400 mg, 1.86 mmol) was dissolved in 10 mL of chloroform, and 3-fluorophthalic anhydride (401 mg, 2.42 mol) was added to the obtained solution. The resulting mixture was then refluxed at 80° C. for 3 days after adding. After the reaction was completed, the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | C(Cl)(Cl)Cl | 80 | null | C=CCOC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21>C(Cl)(Cl)Cl>C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f68dd14708ea4825b48a089d06cc2308 | COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C(C)=O | OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][c:14]([OH:15])[c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([OH:15])[c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C(C)=O | null | null | CC(=O)C.O | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | 100 | CELSIUS | null | null | Methyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.84 g, 2.51 mmol) was dissolved in 24 mL of a solvent mixture of acetone/water (v/v=5/1), and p-toluenesulfonic acid monohydrate (about 0.19 g) was then added to the obtained solution. The resulting mixture was refluxed... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | CC(=O)C.O | 100 | null | COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1>CC(=O)C.O>COC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3ebaa063c454d8d879f69eb56ce606e | COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O | FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (71 mg, 34%) in the same manner as described in the above example 6 (1) from methyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.23 g, 0.70 mmol) and p-toluenesulfonic acid monohydr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62701179ca51420fb3f51cdbc6c5b7ac | COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:22][C:20]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[c:11]([F:12])[cH:13][cH:14][c:15]([F:16])[c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[c:11]([F:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (46 mg, 19%) in the same manner as described in the above example 6 (1) from methyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.24 g, 0.67 mmol) and p-toluenesulfonic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1357119f269043dbbf41f649f1824da3 | COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C(C)=O | [N+](=O)([O-])C1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>[N+](=O)([O-])C1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:23][C:21]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]3[C:19]2=[O:20])([CH3:22])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]2[C:19]1=[O:20])[C:21]([CH3... | COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared in the same manner as described in the above example 6 (1) from methyl 3-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.24 g, 0.67 mmol) and p-toluenesulfonic acid monohydrate (51 mg), an... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9eb773d5cf146d1882af8f7a3cef232 | COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C(C)=O | [N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>[N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:23][C:21]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]3[C:19]2=[O:20])([CH3:22])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]2[C:19]1=[O:20])[C:21]([CH3... | COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (95 mg, 35%) in the same manner as described in the above example 6 (1) from methyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.29 g, 0.82 mmol) and p-toluenesulfonic acid monohydrat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ddaa7f5fed0245d29a48d007a1d6b283 | COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C(C)=O | CC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][c:14]([CH3:15])[c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([CH3:15])[c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(4-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (117 mg, 31%) in the same manner as described in the above example 6 (1) from methyl 3-(4-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.37 g, 1.31 mmol) and p-toluenesulfonic acid monohyd... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ad88a54b4bd49018dc1a7ffa47f287d | COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C(C)=O | CC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][c:13]([CH3:14])[cH:15][c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (23 mg, 26%) in the same manner as described in the above example 6 (1) from methyl 3-(5-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.10 g, 0.30 mmol) and p-toluenesulfonic acid monohydr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-720e49c7acf746f18148a8891b8b18d1 | COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C(C)=O | C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:24][C:22]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][c:19]3[C:20]2=[O:21])([CH3:23])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][c:19]2[C:2... | COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5-t-butyl-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (42 mg, 34%) in the same manner as described in the above example 6 (1) from methyl 3-(5-t-butyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.14 g, 0.34 mmol) and p-toluenesulfonic acid monohy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9a0924a195c42a8b8b44f501e62a87e | COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C(C)=O | ClC1=C2C(N(C(C2=C(C=C1)Cl)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC1=C2C(N(C(C2=C(C=C1)Cl)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:22][C:20]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[c:11]([Cl:12])[cH:13][cH:14][c:15]([Cl:16])[c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[c:11]([Cl:12])[cH:13][cH:14][c:15]([Cl:16])[c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (69 mg, 39%) in the same manner as described in the above example 6 (1) from methyl 3-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.20 g, 0.52 mmol) and p-toluenesulfonic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65905da7d6be42118321cab77b1401e3 | COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C(C)=O | ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C(=O)OC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:22][C:20]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16][c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (46 mg, 19%) in the same manner as described in the above example 6 (1) from methyl 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.24 g, 0.67 mmol) and p-toluenesulfonic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3638464869634d608350c500cadf9765 | COC(=O)C(CN1C(=O)c2cc3ccccc3cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cc3ccccc3cc2C1=O)C(C)=O | O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)CC(C(=O)OC)C3(OCCO3)C.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)CC(C(=O)OC)C(C)=O | C1C[O:24][C:22]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[cH:18][c:19]3[C:20]2=[O:21])([CH3:23])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[cH:18][c:19]2[C:20]1=[O:21])[C:... | COC(=O)C(CN1C(=O)c2cc3ccccc3cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2cc3ccccc3cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2cc3ccccc3cc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(1,3-dioxo-1,3-dihydro-benzo[f]isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (18 mg, 51%) in the same manner as described in the above example 6 (1) from methyl 3-(1,3-dioxo-1,3-dihydro-benzo[f]isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (40 mg, 0.11 mmol) and pyridinium p-toluenesulfonate (5 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2cc3c(cc2c1)C[NH]C3 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2cc3ccccc3cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2cc3ccccc3cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb1e6c547fdd41eab3aaf147b5403fb4 | COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C(C)=O | FC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>FC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (84 mg, 15%) in the same manner as described in the above example 6 (1) from methyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.63 g, 1.87 mmol) and pyridinium p-toluenesulfonate (... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f023ebd192b94180bd6b89b614e87614 | COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C(C)=O | ClC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>ClC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (269 mg, 59%) in the same manner as described in the above example 6 (1) from methyl 3-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.52 g, 1.48 mmol) and pyridinium p-toluenesulfonate ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab63db83853d4ccb8d9d9614aaf7cc4f | COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C(C)=O | BrC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>BrC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C(C)=O)=O | C1C[O:21][C:19]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][N:7]2[C:8](=[O:9])[c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]3[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 | COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Methyl 2-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (106 mg, 24%) in the same manner as described in the above example 6 (1) from methyl 3-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.46 g, 1.14 mmol) and pyridinium p-toluenesulfonate (5... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1>>COC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7980a10b9df46969fa9c65469c6ee48 | CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C(C)=O | O=C1N(C(C=2CCCCC12)=O)CC(C(=O)OCC)C1(OCCO1)C.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O=C1N(C(C=2CCCCC12)=O)CC(C(=O)OCC)C(C)=O | C1C[O:21][C:19]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[C:11]3=[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[C:17]2=[O:18])([CH3:20])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[C:11]2=[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17]1=[O:18])[C:19]([CH3:20])=[O:21] | CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C(C)=O | null | null | CC(=O)C.O | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)C2=C1CCCC2 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | 80 | CELSIUS | null | null | Ethyl 3-(1,3-dioxo-1,3,4,5,6,7-hexahydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (866 mg, 2.57 mmol) was dissolved in a a solvent mixture of acetone/water (v/v=5/1), and a catalytic amount of p-toluenesulfonic acid monohydrate (190 mg, 0.76 mmol) was then added to the obtained solution. The resulting m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | C1CCC2=C(C1)C[NH]C2 | HO- | CC(=O)C.O | 80 | null | CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C1(C)OCCO1>CC(=O)C.O>CCOC(=O)C(CN1C(=O)C2=C(CCCC2)C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e27e690a4aec466f94ab3a1ad3f915b3 | CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O | FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (46 mg, 19%) in the same manner as described in the above example 6 (20) from ethyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.23 g, 0.67 mmol) and p-toluenesulfonic acid monohydra... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1128c1ce8b8c44ffb3d0fb344dab9d9b | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:23][C:21]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[c:12]([F:13])[cH:14][cH:15][c:16]([F:17])[c:18]3[C:19]2=[O:20])([CH3:22])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[c:12]([F:13])[cH:14][cH:15][c:16]([F:17])[c:18]2[C:19]1=[O:20])[C:21]([CH3:22]... | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (95 mg, 19%) in the same manner as described in the above example 6 (20) from ethyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.58 g, 1.57 mmol) and p-toluenesulfonic acid m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b32310baa350497fbb1d64d219987896 | CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C(C)=O | [N+](=O)([O-])C1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>[N+](=O)([O-])C1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:24][C:22]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]3[C:20]2=[O:21])([CH3:23])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]2[C:20]1=[O... | CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (116 mg, 22%) in the same manner as described in the above example 6 (20) from ethyl 3-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.38 g, 1.58 mmol) and p-toluenesulfonic acid monohydrat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b107b3ced8345309a9cc9320ba9b752 | CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C(C)=O | [N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>[N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:24][C:22]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]3[C:20]2=[O:21])([CH3:23])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]2[C:20]1=[O... | CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (263 mg, 27%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (1.11 g, 2.96 mmol) and p-toluenesulfonic acid monohydrat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e41519821f454cd388d56ea46bc3f66f | CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C(C)=O | CC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][c:15]([CH3:16])[c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([CH3:16])[c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(4-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (208 mg, 39%) in the same manner as described in the above example 6 (20) from ethyl 3-(4-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.52 g, 1.76 mmol) and p-toluenesulfonic acid monohydr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b966851e12b34c5d89fd02a94fff8372 | CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C(C)=O | CC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([CH3:15])[cH:16][c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (93 mg, 35%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.38 g, 1.07 mmol) and p-toluenesulfonic acid monohydra... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7d838764484c4e75b33ebcc5f5b9d865 | CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C(C)=O | C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:25][C:23]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]3[C:21]2=[O:22])([CH3:24])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c... | CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5-t-butyl-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (126 mg, 28%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-t-butyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.52 g, 1.33 mmol) and p-toluenesulfonic acid monohy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d97126b1e0d43839371c77736e5d7fa | CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C(C)=O | OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([OH:16])[c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (121 mg, 31%) in the same manner as described in the above example 6 (20) from ethyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.46 g, 1.46 mmol) and p-toluenesulfonic acid monohy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb0f56ce48264298a0ac8f210ad7cd89 | CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C(C)=O | ClC1=C2C(N(C(C2=C(C=C1)Cl)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC1=C2C(N(C(C2=C(C=C1)Cl)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:23][C:21]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[c:12]([Cl:13])[cH:14][cH:15][c:16]([Cl:17])[c:18]3[C:19]2=[O:20])([CH3:22])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[c:12]([Cl:13])[cH:14][cH:15][c:16]([Cl:17])[c:18]2[C:19]1=[O:20])[C:21]([CH3... | CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (264 mg, 26%) in the same manner as described in the above example 6 (20) from ethyl 3-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (1.13 g, 2.80 mmol) and p-toluenesulfonic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2c(Cl)ccc(Cl)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b9942074436404597d0bfe9a603c355 | CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C(C)=O | ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:23][C:21]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]3[C:19]2=[O:20])([CH3:22])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]2[C:19]1=[O:20])[C:21]([CH3... | CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (171 mg, 34%) in the same manner as described in the above example 6 (20) from ethyl 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.57 g, 1.42 mmol) and p-toluenesulfonic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edfa71e5d1c242b187a010eb8f1ce17b | CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C(C)=O | FC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (220 mg, 34%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.75 g, 2.13 mmol) and p-toluenesulfonic acid monohydr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(F)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16cdca0fbdee4983a28bd5c0535e7bcf | CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C(C)=O | ClC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (171 mg, 34%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.45 g, 1.22 mmol) and p-toluenesulfonic acid monohydr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(Cl)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e70fee253b1a44369d949e92a133e2c0 | CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C(C)=O | BrC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OCC)C(C)=O)=O | C1C[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]3[C:18]2=[O:19])([CH3:21])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[C:18]1=[O:19])[C:20]([CH3:21])=[O:22] | CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D4;+0:7]1(-[C;D1;H3:8])-O-C-C-[O;H0;D2;+0:9]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | Ethyl 2-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (168 mg, 31%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.41 g, 1.36 mmol) and p-toluenesulfonic acid monohydrat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2ccc(Br)cc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ab64c3ee79f4ec68259b9f3e101f5c1 | CC(=O)Cl.CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1>>CCOC(=O)C(CN1C(=O)c2cccc(OC(C)=O)c2C1=O)C(C)=O | OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C1(OCCO1)C)=O.N1=CC=CC=C1.C(C)(=O)Cl>>C(C)(=O)OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O | Cl[C:17]([CH3:18])=[O:19].C1C[O:25][C:23]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][c:15]([OH:16])[c:20]3[C:21]2=[O:22])([CH3:24])O1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([O:16][C:17]([CH3:18])=[O:19])[... | CC(=O)Cl.CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1 | CCOC(=O)C(CN1C(=O)c2cccc(OC(C)=O)c2C1=O)C(C)=O | null | null | ClCCl | Acylation | OtherReaction | 74b36f1a0dde9c2a1493cb51d1389fac31d3bec25f9609135736b36210e13199 | 10c4aaf8721ada3036ed96c6b4889612752b36faab04ff410d360199e0d16b75 | O=C1NC(=O)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8](-[C:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]:[c:14](-[OH;D1;+0:15]):[c:16])-[C;H0;D4;+0:17]1(-[C;D1;H3:18])-O-C-C-[O;H0;D2;+0:19]-1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8](-[C:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]:[c:14](-[O;H0;D2;+0:15... | 54.2 | [{"value": 54.0, "product": "C(C)(=O)OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.2, "product": "C(C)(=O)OC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC)C(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Ethyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (102.4 mg, 0.34 mmol) was dissolved in dichloromethane, and pyridine (55 μl, 0.682 mmol) and acetyl chloride (49 μl, 0.68 mmol) were then slowly added dropwise to the obtained solution at 0° C. The resulting mixture was th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Ether.Aromatic alcohol | Ketone.Ester | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HCl | ClCCl | null | 0.166667 | CC(=O)Cl.CCOC(=O)C(CN1C(=O)c2cccc(O)c2C1=O)C1(C)OCCO1>ClCCl>CCOC(=O)C(CN1C(=O)c2cccc(OC(C)=O)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbb505f7b1a54d5491bd553456441248 | C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1>>C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O | FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC=C)C1(OCCO1)C)=O.C1(=CC=C(C=C1)S(=O)(=O)OS(=O)(=O)C1=CC=C(C=C1)C)C>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OCC=C)C(C)=O)=O | C1C[O:23][C:21]([CH:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:8][N:9]2[C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]3[C:19]2=[O:20])([CH3:22])O1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH:7]([CH2:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]2[C:19]1=[O:20])[C:21]([CH3:2... | C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O | null | null | CC(=O)C.O | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]=[C;D1;H2:8])-[C;H0;D4;+0:9]1(-[C;D1;H3:10])-O-C-C-[O;H0;D2;+0:11]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]=[C;D1;H2:8])-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11] | null | [] | 80 | CELSIUS | null | null | Allyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (331 mg, 0.91 mmol) was dissolved in a a solvent mixture of acetone/water (v/v=5/1), and catalyst amount of p-toluenesulfonic acid anhydride was added to the obtained solution. The resulting mixture was refluxed at 80° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | CC(=O)C.O | 80 | null | C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1>CC(=O)C.O>C=CCOC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0e06be6c1f349d980d1a243c257c9be | C=CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1>>C=CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OCC=C)C1(OCCO1)C)=O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OCC=C)C(C)=O)=O | C1C[O:24][C:22]([CH:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:8][N:9]2[C:10](=[O:11])[c:12]3[c:13]([F:14])[cH:15][cH:16][c:17]([F:18])[c:19]3[C:20]2=[O:21])([CH3:23])O1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH:7]([CH2:8][N:9]1[C:10](=[O:11])[c:12]2[c:13]([F:14])[cH:15][cH:16][c:17]([F:18])[c:19]2[C:20]1=[O:21]... | C=CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | C=CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]=[C;D1;H2:8])-[C;H0;D4;+0:9]1(-[C;D1;H3:10])-O-C-C-[O;H0;D2;+0:11]-1>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]-[C:7]=[C;D1;H2:8])-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11] | null | [] | null | null | null | null | Allyl 2-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (86 mg, 23%) in the same manner as described in the above Example 6 (40) from allyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.35 g, 0.92 mmol) and p-toluenesulfonic acid m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | C=CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1>>C=CCOC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9468fbfcecd4c3a9ebd4c328a36dce6 | C=C=C(CC(O)CCC(C)=O)C[Si](C)(C)C>>C=C1CC2CCC(C)(O2)C1=C | O.C(C)OCC.OC(CCC(C)=O)CC(=C=C)C[Si](C)(C)C.FC(S(=O)(=O)O[Si](C)(C)C)(F)F>>CC12C(C(CC(CC1)O2)=C)=C | C[Si](C)(C)[CH2:10][C:2](=[C:1]=[CH2:11])[CH2:3][CH:4](O)[CH2:5][CH2:6][C:7]([CH3:8])=[O:9]>>[CH2:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][C:7]([CH3:8])([O:9]2)[C:10]1=[CH2:11] | C=C=C(CC(O)CCC(C)=O)C[Si](C)(C)C | C=C1CC2CCC(C)(O2)C1=C | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 6aef231dd1a031932fd908a7abaacfbac2680aadf19f1a4c9f1ff3e51f2a5518 | 89bd44f901d8a093f1cd13a927c119e45bbcc230b4473f7bceea85667b283899 | C=C1CC2CCC(O2)C1=C | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C:2](-[C:3]-[CH;D3;+0:4](-O)-[C:5]-[C:6]-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9])=[C;H0;D2;+0:10]=[CH2;D1;+0:11]>>[C;D1;H3:8]-[C;H0;D4;+0:7]12-[C:6]-[C:5]-[CH;D3;+0:4](-[C:3]-[C:2](=[CH2;D1;+0:10])-[C;H0;D3;+0:1]-1=[CH2;D1;+0:11])-[O;H0;D2;+0:9]-2 | 94.3 | [{"value": 94.0, "product": "CC12C(C(CC(CC1)O2)=C)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "CC12C(C(CC(CC1)O2)=C)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 1.50 mL of diethyl ether was added to 5-hydroxy-7-trimethylsilanylmethyl-nona-7,8-diene-2-one (86 mg, 0.36 mmol) under nitrogen atmosphere. While stirring at −78° C., trimethylsilyl trifluoromethanesulfonate (TMSOTf; 64.7 μL, 0.36 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Allene.Silyl protective group | Ether.Vinyl.Vinyl | null | C1CC2CCC(C1)O2 | C1CC2CCC(C1)O2 | HO- | C(C)(=O)OCC | -78 | null | C=C=C(CC(O)CCC(C)=O)C[Si](C)(C)C>C(C)(=O)OCC>C=C1CC2CCC(C)(O2)C1=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca52429c7d944b719557a85bafc3b396 | C=C=C(CC(O)CCC(=O)c1ccccc1)C[Si](C)(C)C>>C=C1CC2CCC(c3ccccc3)(O2)C1=C | O.C(C)OCC.OC(CCC(=O)C1=CC=CC=C1)CC(=C=C)C[Si](C)(C)C.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C=C1C2(CCC(CC1=C)O2)C2=CC=CC=C2 | C[Si](C)(C)[CH2:15][C:2](=[C:1]=[CH2:16])[CH2:3][CH:4]([CH2:5][CH2:6][C:7](=O)[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[OH:14]>>[CH2:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][C:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)([O:14]2)[C:15]1=[CH2:16] | C=C=C(CC(O)CCC(=O)c1ccccc1)C[Si](C)(C)C | C=C1CC2CCC(c3ccccc3)(O2)C1=C | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 6aef231dd1a031932fd908a7abaacfbac2680aadf19f1a4c9f1ff3e51f2a5518 | 89bd44f901d8a093f1cd13a927c119e45bbcc230b4473f7bceea85667b283899 | C=C1CC2CCC(c3ccccc3)(O2)C1=C | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C:2](-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-[C:7]-[C;H0;D3;+0:8](=O)-[c:9](:[c:10]):[c:11])=[C;H0;D2;+0:12]=[CH2;D1;+0:13]>>[CH2;D1;+0:13]=[C;H0;D3;+0:1]1-[C:2](=[CH2;D1;+0:12])-[C:3]-[C:4]2-[C:6]-[C:7]-[C;H0;D4;+0:8]-1(-[c:9](:[c:10]):[c:11])-[O;H0;D2;+0:5]-2 | 96.8 | [{"value": 96.0, "product": "C=C1C2(CCC(CC1=C)O2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "C=C1C2(CCC(CC1=C)O2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 1.50 mL of diethyl ether was added to 4-hydroxy-1-phenyl-6-trimethylsilanylmethyl-octa-6.7-diene-1-one (110 mg, 0.36 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (64.7 μL, 0.36 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Allene.Silyl protective group | Ether.Vinyl.Vinyl | null | C1CC2CCC(C1)O2 | C1CC2CCC(C1)O2.c1ccccc1 | HO- | CCOC(=O)C | -78 | null | C=C=C(CC(O)CCC(=O)c1ccccc1)C[Si](C)(C)C>CCOC(=O)C>C=C1CC2CCC(c3ccccc3)(O2)C1=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cebfcae03c554024b6a4d007d5dc77c3 | C=C=C(CC(O)c1ccccc1C=O)C[Si](C)(C)C>>C=C1CC2OC(C1=C)C1C=CC=C=C21 | O.C(C)OCC.OC(CC(=C=C)C[Si](C)(C)C)C1=C(C=O)C=CC=C1.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C=C1C2C3C=CC=C=C3C(CC1=C)O2 | C[Si](C)(C)[CH2:8][C:7](=[C:2]=[CH2:1])[CH2:3][CH:4]([OH:5])[c:14]1[c:9]([CH:6]=O)[cH:10][cH:11][cH:12][cH:13]1>>[CH2:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH:6]([C:7]1=[CH2:8])[CH:9]1[CH:10]=[CH:11][CH:12]=[C:13]=[C:14]21 | C=C=C(CC(O)c1ccccc1C=O)C[Si](C)(C)C | C=C1CC2OC(C1=C)C1C=CC=C=C21 | null | null | CCOC(=O)C | Reduction | OtherReaction | 21d70ea98e3c6f33513fa84fba7abae1856a53be3f335ab357348d3538cbc324 | 9a80bacad9022e560be8e6d371e6af5cd7b2b02f82a3db3a4a100414e754d162 | C=C1CC2OC(C1=C)C1C=CC=C=C21 | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[C;H0;D2;+0:3]=[C;D1;H2:4])-[CH2;D2;+0:5]-[C:6](-[OH;D1;+0:7])-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[CH;D2;+0:14]=O>>[C;D1;H2:4]=[C;H0;D3;+0:3]1-[CH2;D2;+0:5]-[C:6]2-[O;H0;D2;+0:7]-[CH;D3;+0:14](-[C;H0;D3;+0:2]-1=[CH2;D1;+0... | 77.2 | [{"value": 77.0, "product": "C=C1C2C3C=CC=C=C3C(CC1=C)O2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "C=C1C2C3C=CC=C=C3C(CC1=C)O2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 5.2 mL of diethyl ether was added to 2-(1-hydroxy-3-trimethylsilanylmethyl-penta-3,4-dienyl)-benzaldehyde (358 mg, 1.30 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (235 μL, 1.30 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol.Allene.Silyl protective group | Ether.Vinyl.Vinyl.Allene | c1ccccc1 | C1=CC=CC2C=1C1CCCC2O1 | C1=CC=CC2C=1C1CCCC2O1 | HO- | CCOC(=O)C | -78 | null | C=C=C(CC(O)c1ccccc1C=O)C[Si](C)(C)C>CCOC(=O)C>C=C1CC2OC(C1=C)C1C=CC=C=C21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7a75a81d0d140da93aa04a74ed8d4fd | C=C=C(CC(O)CC1CCCC1=O)C[Si](C)(C)C>>C=C1CC2CC3CCCC3(O2)C1=C | O.C(C)OCC.OC(CC1C(CCC1)=O)CC(=C=C)C[Si](C)(C)C.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C=C1CC2CC3CCCC3(C1=C)O2 | C[Si](C)(C)[CH2:12][C:2](=[C:1]=[CH2:13])[CH2:3][CH:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][C:10]1=O)[OH:11]>>[CH2:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH:6]3[CH2:7][CH2:8][CH2:9][C:10]3([O:11]2)[C:12]1=[CH2:13] | C=C=C(CC(O)CC1CCCC1=O)C[Si](C)(C)C | C=C1CC2CC3CCCC3(O2)C1=C | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | e3a012bab00abb279dea2da371660d0b01b1cf2d295a6197e7bb079cf94c108f | 89bd44f901d8a093f1cd13a927c119e45bbcc230b4473f7bceea85667b283899 | C=C1CC2CC3CCCC3(O2)C1=C | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C:2](-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[C;H0;D3;+0:11]-1=O)=[C;H0;D2;+0:12]=[CH2;D1;+0:13]>>[CH2;D1;+0:13]=[C;H0;D3;+0:1]1-[C:2](=[CH2;D1;+0:12])-[C:3]-[C:4]2-[C:6]-[C:7]3-[C:8]-[C:9]-[C:10]-[C;H0;D4;+0:11]-3-1-[O;H0;D2;+0:5]-2 | 78.6 | [{"value": 77.0, "product": "C=C1CC2CC3CCCC3(C1=C)O2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "C=C1CC2CC3CCCC3(C1=C)O2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 1.1 mL of diethyl ether was added to 2-(2-hydroxy-4-trimethylsilanylmethyl-hexa-4,5-dienyl)-cyclopentanone (70 mg, 0.26 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (48 μL, 0.26 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Allene.Silyl protective group | Ether.Vinyl.Vinyl | C1CCCC1 | C1CC2CC3CCCC3(C1)O2 | C1CC2CC3CCCC3(C1)O2 | HO- | CCOC(=O)C | -78 | null | C=C=C(CC(O)CC1CCCC1=O)C[Si](C)(C)C>CCOC(=O)C>C=C1CC2CC3CCCC3(O2)C1=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64eff3d1816e4a43a31ba2f5a16e85bb | C=C=C(CC(O)CC1CCCCC1=O)C[Si](C)(C)C>>C=C1CC2CC3CCCCC3(O2)C1=C | O.C(C)OCC.OC(CC1C(CCCC1)=O)CC(=C=C)C[Si](C)(C)C.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C=C1CC2CC3CCCCC3(C1=C)O2 | C[Si](C)(C)[CH2:13][C:2](=[C:1]=[CH2:14])[CH2:3][CH:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1=O)[OH:12]>>[CH2:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]3([O:12]2)[C:13]1=[CH2:14] | C=C=C(CC(O)CC1CCCCC1=O)C[Si](C)(C)C | C=C1CC2CC3CCCCC3(O2)C1=C | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 20caf4eb4814201af66b9e83dab15d99eef926e68bfff90216813ae1078f11de | 89bd44f901d8a093f1cd13a927c119e45bbcc230b4473f7bceea85667b283899 | C=C1CC2CC3CCCCC3(O2)C1=C | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C:2](-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-[C:7](-[C:8])-[C;H0;D3;+0:9](=O)-[C:10]-[C:11])=[C;H0;D2;+0:12]=[CH2;D1;+0:13]>>[C:8]-[C:7]1-[C:6]-[C:4]2-[C:3]-[C:2](=[CH2;D1;+0:12])-[C;H0;D3;+0:1](=[CH2;D1;+0:13])-[C;H0;D4;+0:9]-1(-[C:10]-[C:11])-[O;H0;D2;+0:5]-2 | 78 | [{"value": 78.0, "product": "C=C1CC2CC3CCCCC3(C1=C)O2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "C=C1CC2CC3CCCCC3(C1=C)O2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 1.5 mL of diethyl ether was added to 2-(2-hydroxy-4-trimethylsilanylmethyl-hexa-4,5-dienyl)-cyclohexanone (100 mg, 0.36 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (64.5 μL, 0.36 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Allene.Silyl protective group | Ether.Vinyl.Vinyl | C1CCCCC1 | C1CCC23CCCC(CC2C1)O3 | C1CCC23CCCC(CC2C1)O3 | HO- | CCOC(=O)C | -78 | null | C=C=C(CC(O)CC1CCCCC1=O)C[Si](C)(C)C>CCOC(=O)C>C=C1CC2CC3CCCCC3(O2)C1=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d98115824bce4000b70e1610633eaced | C=C=C(CC(O)CC1CCCCCC1=O)C[Si](C)(C)C>>C=C1CC2CC3CCCCCC3(O2)C1=C | O.CCOCC.OC(CC1C(CCCCC1)=O)CC(=C=C)C[Si](C)(C)C.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C=C1CC2CC3CCCCCC3(C1=C)O2 | C[Si](C)(C)[CH2:14][C:2](=[C:1]=[CH2:15])[CH2:3][CH:4](O)[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1=[O:13]>>[CH2:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]3([O:13]2)[C:14]1=[CH2:15] | C=C=C(CC(O)CC1CCCCCC1=O)C[Si](C)(C)C | C=C1CC2CC3CCCCCC3(O2)C1=C | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 3c576ff88f6aff6acb77915aab2a4a0d8fe0c4abe09fee22cff9657431ab00b6 | 89bd44f901d8a093f1cd13a927c119e45bbcc230b4473f7bceea85667b283899 | C=C1CC2CC3CCCCCC3(O2)C1=C | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C:2](-[C:3]-[CH;D3;+0:4](-O)-[C:5]-[C:6](-[C:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]-[C:11])=[C;H0;D2;+0:12]=[CH2;D1;+0:13]>>[C:11]-[C:10]-[C;H0;D4;+0:8]12-[O;H0;D2;+0:9]-[CH;D3;+0:4](-[C:3]-[C:2](=[CH2;D1;+0:12])-[C;H0;D3;+0:1]-1=[CH2;D1;+0:13])-[C:5]-[C:6]-2-[C:7] | 90.2 | [{"value": 90.0, "product": "C=C1CC2CC3CCCCCC3(C1=C)O2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.2, "product": "C=C1CC2CC3CCCCCC3(C1=C)O2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | 1.30 mL of ether was added to 2-(2-hydroxy-4-trimethylsilanylmethyl-hexa-4,5-dienyl)-cycloheptanone (95 mg, 0.32 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (58.4 μL, 0.32 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature for 3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary alcohol.Allene.Silyl protective group | Ether.Vinyl.Vinyl | C1CCCCCC1 | C1CCC2CC3CCCC2(CC1)O3 | C1CCC2CC3CCCC2(CC1)O3 | HO- | CCOC(=O)C | -78 | null | C=C=C(CC(O)CC1CCCCCC1=O)C[Si](C)(C)C>CCOC(=O)C>C=C1CC2CC3CCCCCC3(O2)C1=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c2a80a2d1154010aca22c7ac1ac6a93 | COC(=O)c1ccc(C(F)(F)F)cc1[N+](=O)[O-].C[S-]>>COC(=O)c1ccc(C(F)(F)F)cc1SC | C[S-].[Na+].[N+](=O)([O-])C1=C(C(=O)OC)C=CC(=C1)C(F)(F)F>>CSC1=C(C(=O)OC)C=CC(=C1)C(F)(F)F | O=[N+]([O-])[c:14]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1.[S-:15][CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[S:15][CH3:16] | COC(=O)c1ccc(C(F)(F)F)cc1[N+](=O)[O-].C[S-] | COC(=O)c1ccc(C(F)(F)F)cc1SC | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | a2c5de54d572b1b7b77bab1c1b5e66676bcc489fa7c5c5e2277967f40a73f057 | 584a0ae1f6f3f62784f5d37b0650f491a1fe511cf5bf271ab4525bc0f6bf414d | c1ccccc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9].[C;D1;H3:10]-[S-;H0;D1:11]>>[C;D1;H3:10]-[S;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9] | 103.9 | [{"value": 103.9, "product": "CSC1=C(C(=O)OC)C=CC(=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium thiomethoxide (91 mg; 1.3 mmol; 1.3 equiv) was dissolved in water (0.34 mL). Tetrabutylammonium bromide (48 mg; 0.15 mmol; 0.15 equiv) was added. Methyl 2-nitro-4trifluoromethylbenzoate (5a; 249 mg; 1.0 mmol) was dissolved in toluene and added to the mixture. The reaction mixture was stirred at ambient temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C1(=CC=CC=C1)C | null | 1 | COC(=O)c1ccc(C(F)(F)F)cc1[N+](=O)[O-].C[S-]>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C1(=CC=CC=C1)C>COC(=O)c1ccc(C(F)(F)F)cc1SC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4ad2d2b18aa4c3b8db9e260bf88c5de | CCN(CC)CC.CO.C[S-].O=[N+]([O-])c1cc(C(F)(F)F)ccc1Br>>COC(=O)c1ccc(C(F)(F)F)cc1SC | BrC1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-].C(C)N(CC)CC.CO.C[S-].[Na+].O>>CSC1=C(C(=O)OC)C=CC(=C1)C(F)(F)F | CCN(CC)C[CH3:14].[CH3:1][OH:2].[S-:15][CH3:16].[O-][N+](=[O:4])[c:5]1[c:3](Br)[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[S:15][CH3:16] | CCN(CC)CC.CO.C[S-].O=[N+]([O-])c1cc(C(F)(F)F)ccc1Br | COC(=O)c1ccc(C(F)(F)F)cc1SC | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Acylation | OtherReaction | e2ca1bb39888d4631f5b757b65965607e449b06b76e8f1263fd66526c9824c68 | 40b0a56f8c4c4fd4ae76ce1b887c15d23cee9642af26b34a803ba7a170540a9d | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3]:[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[cH;D2;+0:9]:[c;H0;D3;+0:10]:1-[N+](-[O-])=[O;H0;D1;+0:11].C-C-N(-C-C)-C-[CH3;D1;+0:12].[C;D1;H3:13]-[OH;D1;+0:14].[C;D1;H3:15]-[S-;H0;D1:16]>>[C;D1;H3:15]-[S;H0;D2;+0:16]-[c;H0;D3;+0:12]1:[cH;D2;+0:9]:[c:4](-[C:5](-[F;D1;H0:6])... | null | [] | 100 | CELSIUS | 18 | HOUR | Dichlorobis(triphenylphosphine)palladium (140 mg; 0.20 mmol; 0.01 equiv) was added to a 100-mL autoclave. A mixture of 4-bromo-3-nitrobenzotrifluoride (4a; 3.06 mL; 20 mmol), triethylamine (3.5 mL; 25 mmol; 1.25 equiv), and methanol (60 mL; 75 equiv) was added and the mixture was pressurized and purged with helium thre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Tertiary amine.Methanol | Ester.Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | 100 | 18 | CCN(CC)CC.CO.C[S-].O=[N+]([O-])c1cc(C(F)(F)F)ccc1Br>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>COC(=O)c1ccc(C(F)(F)F)cc1SC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c23ebe7c2534221923202bb5e04eb41 | COc1ccc(OC)c(C(=O)CNC(=O)CCl)c1.[N-]=[N+]=[N-]>>COc1ccc(OC)c(C(=O)CNC(=O)CN=[N+]=[N-])c1 | ClCC(=O)NCC(C1=C(C=CC(=C1)OC)OC)=O.[N-]=[N+]=[N-].[Na+].[I-].[K+]>>N(=[N+]=[N-])CC(=O)NCC(C1=C(C=CC(=C1)OC)OC)=O | Cl[CH2:16][C:14]([NH:13][CH2:12][C:10]([c:9]1[c:6]([O:7][CH3:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20]1)=[O:11])=[O:15].[N-:17]=[N+:18]=[N-:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([C:10](=[O:11])[CH2:12][NH:13][C:14](=[O:15])[CH2:16][N:17]=[N+:18]=[N-:19])[cH:20]1 | COc1ccc(OC)c(C(=O)CNC(=O)CCl)c1.[N-]=[N+]=[N-] | COc1ccc(OC)c(C(=O)CNC(=O)CN=[N+]=[N-])c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]-[C:6]=[O;D1;H0:7].[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[N;-;D1;H0:10]=[#7;+:9]=[N;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]-[C:6]=[O;D1;H0:7] | 91 | [{"value": 91.0, "product": "N(=[N+]=[N-])CC(=O)NCC(C1=C(C=CC(=C1)OC)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | In a four neck round bottomed flask, 45 gm (0.165 mole) of 2-Chloro-N-(β-oxo-2,5-Dimethoxy phenethyl)-acetamide prepared according to step (b), 27 g (0.415 mole) sodium azide and 8.3 g (0.049 mole) potassium iodide and 900 ml of acetone is charged. The solution is refluxed at 60° C. for 5 hours. After completion of the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccccc1 | Other | CC(=O)C | 60 | null | COc1ccc(OC)c(C(=O)CNC(=O)CCl)c1.[N-]=[N+]=[N-]>CC(=O)C>COc1ccc(OC)c(C(=O)CNC(=O)CN=[N+]=[N-])c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49b04b3396aa4f99b9f5b82ae05606ee | COc1ccc(OC)c(C(=O)CNC(=O)CN=[N+]=[N-])c1>>COc1ccc(OC)c(C(O)CNC(=O)CN=[N+]=[N-])c1 | N(=[N+]=[N-])CC(=O)NCC(C1=C(C=CC(=C1)OC)OC)=O.[BH4-].[Na+].C(C)(=O)O>>N(=[N+]=[N-])CC(=O)NCC(C1=C(C=CC(=C1)OC)OC)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([C:10](=[O:11])[CH2:12][NH:13][C:14](=[O:15])[CH2:16][N:17]=[N+:18]=[N-:19])[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([CH:10]([OH:11])[CH2:12][NH:13][C:14](=[O:15])[CH2:16][N:17]=[N+:18]=[N-:19])[cH:20]1 | COc1ccc(OC)c(C(=O)CNC(=O)CN=[N+]=[N-])c1 | COc1ccc(OC)c(C(O)CNC(=O)CN=[N+]=[N-])c1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:1]=[C:2]-[#7:3]-[C:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[c:7](:[c:8]):[c:9] | 95 | [{"value": 95.0, "product": "N(=[N+]=[N-])CC(=O)NCC(C1=C(C=CC(=C1)OC)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | In a four neck round bottomed flask 32.4 gm (0.11 mole) of 2-azido-N-(β-Oxo-2,5-dimethoxy phenehyl)-acetamide is prepared according to the step (c) and 260 ml methanol is charged and cooled to 0° C. To this 3.24 gm (0.08 mole) sodium boro hydride is added slowly over a period. After completion of the addition, the reac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | CO | 0 | null | COc1ccc(OC)c(C(=O)CNC(=O)CN=[N+]=[N-])c1>CO>COc1ccc(OC)c(C(O)CNC(=O)CN=[N+]=[N-])c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c173cccf2294dd195a5d48fb56cd6ad | Nc1ccccc1.OCCCCCCCl>>OCCCCCCN(CCCCCCO)c1ccccc1 | NC1=CC=CC=C1.ClCCCCCCO.C([O-])([O-])=O.[K+].[K+]>>OCCCCCCN(C1=CC=CC=C1)CCCCCCO | [NH2:8][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | Nc1ccccc1.OCCCCCCCl | OCCCCCCN(CCCCCCO)c1ccccc1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | cb80e9a46d8c2d8d08c158090272d8a5b407d47fba09c3f98fc6474f6bb994bf | cfc7b673978f72d38d33e3cd77e47153ac3726463ad8eac018511ad9c173bf12 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:8]-[C:9])-[c:5](:[c:6]):[c:7] | 60 | [{"value": 60.0, "product": "OCCCCCCN(C1=CC=CC=C1)CCCCCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 9.3 g (100 mmol) freshly distilled aniline, 30.0 g (220 mmol) 6-chloro-1-hexanol and 30.4 g (220 mmol) potassium carbonate were heated in 50 ml of n-butanol under reflux for 4 days. After cooling the solids were filtered of and the solvent is removed in vacuum. Purification by liquid chromatography (ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Primary alcohol.Tertiary amine | null | null | c1ccccc1 | null | C(CCC)O | null | null | Nc1ccccc1.OCCCCCCCl>C(CCC)O>OCCCCCCN(CCCCCCO)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23c4a84d57fe4641be57dc04c183155c | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | COC(C)(C)C.N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O.N(=O)[O-].[Na+]>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 86 | [{"value": 86.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.5, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was stirred at 20° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 20 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edcb3a81fb514e78824e93b36d4fa57d | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 87 | [{"value": 87.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 5.93 g (60.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 20 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9255b6e2cea94af38ecea3b74658cfbd | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 123.5 | [{"value": 87.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 123.5, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 4.15 g (42.4 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 20 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-420957afd9b44a9fab3ce48480a6b208 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 69 | [{"value": 69.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 14.83 g (151.3 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 20 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82ddcfc87e73454eb44775dbd7683f7e | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 70 | [{"value": 70.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 0° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 0 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96950af56707463597c262dab0ced699 | N[C@@H](Cc1ccccc1)C(=O)O.O=N[O-]>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O>>O[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.O=N[O-:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=N[O-] | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O.S(O)(O)(=O)=O | Heteroatom Alkylation and Arylation | OtherReaction | 96293b935516bd3d70ed9581b0ffab95b04652155775b1fa9490160f75981e14 | 0401edb90dae5ba876eed037c39fbf2af9211443c51f74e11f18bcb04d1c906f | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O=N-[O-;H0;D1:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 85 | [{"value": 85.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 14 g (217 mmol) of sodium nitrite in 20 ml of water was added dropwise to a solution of 14 g (85 mmol) of L-phenylalanine in 100 ml of 1 N sulfuric acid at 0° C. over 3 hours, and the mixture was stirred overnight at room temperature. After extraction with three 100-ml portions of ethyl acetate, the organ... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O.S(O)(O)(=O)=O | null | 8 | N[C@@H](Cc1ccccc1)C(=O)O.O=N[O-]>O.S(O)(O)(=O)=O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34b06c52d9884760b076e7e3869bff2c | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 89 | [{"value": 89.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 40° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 40 | null | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ce647dc35724674a6e47ab76fa24571 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 85 | [{"value": 85.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 70° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 70 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66c520f123764eefb64f66951fce3ddc | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 85 | [{"value": 85.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 2 hours. After addition, the mixture was stirred at 20° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 20 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-027bf69b4874463cb094106d2ed51263 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | N(=O)[O-].[Na+].N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 64 | [{"value": 64.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 55 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | O | 20 | 20 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>O>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79eb3b90098a49eca07b18af68982a22 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>>O=C(O)[C@@H](O)Cc1ccccc1 | Cl.N[C@@H](CC1=CC=CC=C1)C(=O)O.S(O)(O)(=O)=O.N(=O)[O-].[Na+].O>>O[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.O=S(=O)(O)[OH:5]>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O | O=C(O)[C@@H](O)Cc1ccccc1 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 6305f39d713203796327b5582587c533759939bc4f6c83ca30f3a398df504033 | ddaf11a7e50668ee9409cbdeaf9c6593f1c2842e515616fbd57e96c3fd2bf6e3 | c1ccccc1 | N-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].O-S(=O)(=O)-[OH;D1;+0:7]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C@@H;D3;+0:1](-[OH;D1;+0:7])-[C:2]-[c:3] | 42 | [{"value": 42.0, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.8, "product": "O[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | L-Phenylalanine hydrochloride (12.2 g, 60.5 mmol) was added to 183 ml of 5% sulfuric acid (sulfuric acid: 96.0 mmol) and the solution was treated with a mixture of 8.35 g (121 mmol) of sodium nitrite and 44.5 g of water at 0° C. for 3 hours. Thereafter, 100 ml of diethyl ether was added to the reaction mixture and, aft... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary alcohol | null | null | c1ccccc1 | HO- | C(C)OCC | null | null | N[C@@H](Cc1ccccc1)C(=O)O.O=S(=O)(O)O>C(C)OCC>O=C(O)[C@@H](O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f826208111eb48df98d017f97031333a | O=C(O)[C@@H](O)Cc1ccccc1.O=S(Cl)Cl>>O=C(O)[C@H](Cl)Cc1ccccc1 | S(=O)(Cl)Cl.O[C@H](C(=O)O)CC1=CC=CC=C1.O>>Cl[C@@H](C(=O)O)CC1=CC=CC=C1 | O[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.O=S(Cl)[Cl:5]>>[O:1]=[C:2]([OH:3])[C@H:4]([Cl:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | O=C(O)[C@@H](O)Cc1ccccc1.O=S(Cl)Cl | O=C(O)[C@H](Cl)Cc1ccccc1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC | O1CCCC1 | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C@@H;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[Cl;H0;D1;+0:1]-[C@H;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 90.1 | [{"value": 90.0, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 15 | HOUR | Thionyl chloride (0.66 ml, 9.0 mmol) was added dropwise to a solution of (2S)-2-hydroxy-3-phenylpropionic acid (500 mg, 3.0 mmol, optical purity 100% ee (S)) in 5 ml of tetrahydrofuran at room temperature, and the mixture was stirred for 15 hours. To the reaction mixture was added 170 mg (0.60 mmol) of tetra-n-butylamm... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HCl | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCCC1 | 40 | 15 | O=C(O)[C@@H](O)Cc1ccccc1.O=S(Cl)Cl>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCCC1>O=C(O)[C@H](Cl)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ace0d3f0bca842909fab2c1f9032469b | Cl.O=C(O)[C@@H](O)Cc1ccccc1>>O=C(O)[C@H](Cl)Cc1ccccc1 | Cl.S(=O)(Cl)Cl.O[C@H](C(=O)O)CC1=CC=CC=C1.CN(C=O)C>>Cl[C@@H](C(=O)O)CC1=CC=CC=C1 | [ClH:5].O[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>>[O:1]=[C:2]([OH:3])[C@H:4]([Cl:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | Cl.O=C(O)[C@@H](O)Cc1ccccc1 | O=C(O)[C@H](Cl)Cc1ccccc1 | null | null | O.O1CCCC1.C1(=CC=CC=C1)C | Miscellaneous | Alcohol to chloride_HCl | 0b8aa535606bb6d799ae035c3035d948e3eeed30a3f065a1ed6275598226022d | c32244244ec49ec521938c83c713d3129edfe4b7502c328e1c36f2eef304d82a | c1ccccc1 | O-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[ClH;D0;+0:7]>>[Cl;H0;D1;+0:7]-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 93 | [{"value": 93.0, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 37.5 | CELSIUS | 2 | HOUR | Thionyl chloride (43.8 g, 368.4 mmol) was added dropwise to a solution of 20.4 g (122.8 mmol) of (2S)-2-hydroxy-3-phenylpropionic acid (optical purity 100% ee (S)) in 200 ml of tetrahydrofuran, and the mixture was stirred at 35 to 40° C. for 2 hours. To that solution was added 1.8 g (24.6 mmol) of dimethylformamide, an... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HO- | O.O1CCCC1.C1(=CC=CC=C1)C | 37.5 | 2 | Cl.O=C(O)[C@@H](O)Cc1ccccc1>O.O1CCCC1.C1(=CC=CC=C1)C>O=C(O)[C@H](Cl)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-676602d0f422426992ce2497de828afa | Cl.O=C(O)[C@@H](O)Cc1ccccc1>>O=C(O)[C@H](Cl)Cc1ccccc1 | Cl.O[C@H](C(=O)O)CC1=CC=CC=C1.S(=O)(Cl)Cl.CN(C=O)C>>Cl[C@@H](C(=O)O)CC1=CC=CC=C1 | [ClH:5].O[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>>[O:1]=[C:2]([OH:3])[C@H:4]([Cl:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | Cl.O=C(O)[C@@H](O)Cc1ccccc1 | O=C(O)[C@H](Cl)Cc1ccccc1 | null | null | O.O1CCOCC1.C1(=CC=CC=C1)C | Miscellaneous | Alcohol to chloride_HCl | 0b8aa535606bb6d799ae035c3035d948e3eeed30a3f065a1ed6275598226022d | c32244244ec49ec521938c83c713d3129edfe4b7502c328e1c36f2eef304d82a | c1ccccc1 | O-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[ClH;D0;+0:7]>>[Cl;H0;D1;+0:7]-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 84.1 | [{"value": 84.0, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | 1,4-Dioxane (200 ml) was added to 20.4 g (122.8 mmol) of (2S)-2-hydroxy-3-phenylpropionic acid (optical purity 100% ee (S)), 43.8 g (368.4 mmol) of thionyl chloride was added dropwise, and the mixture was stirred at 40° C. for 2 hours. To that solution was added 1.8 g (24.6 mmol) of dimethylformamide, and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HO- | O.O1CCOCC1.C1(=CC=CC=C1)C | 40 | 2 | Cl.O=C(O)[C@@H](O)Cc1ccccc1>O.O1CCOCC1.C1(=CC=CC=C1)C>O=C(O)[C@H](Cl)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b86ef2a16984fffb9c07f941abec728 | Cl.O=C(O)[C@@H](O)Cc1ccccc1>>O=C(O)[C@H](Cl)Cc1ccccc1 | Cl.S(=O)(Cl)Cl.O[C@H](C(=O)O)CC1=CC=CC=C1.CN(C=O)C>>Cl[C@@H](C(=O)O)CC1=CC=CC=C1 | [ClH:5].O[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>>[O:1]=[C:2]([OH:3])[C@H:4]([Cl:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | Cl.O=C(O)[C@@H](O)Cc1ccccc1 | O=C(O)[C@H](Cl)Cc1ccccc1 | null | null | O.C1(=CC=CC=C1)C | Miscellaneous | Alcohol to chloride_HCl | 0b8aa535606bb6d799ae035c3035d948e3eeed30a3f065a1ed6275598226022d | c32244244ec49ec521938c83c713d3129edfe4b7502c328e1c36f2eef304d82a | c1ccccc1 | O-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[ClH;D0;+0:7]>>[Cl;H0;D1;+0:7]-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 95 | [{"value": 95.0, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | Thionyl chloride (43.8 g, 368.4 mmol) was added dropwise to a solution of 20.4 g (122.8 mmol) of (2S)-2-hydroxy-3-phenylpropionic acid (optical purity 100% ee (S)) in 200 ml of toluene, and the mixture was stirred at 40° C. for 2 hours. To that solution was added 1.8 g (24.6 mmol) of dimethylformamide, and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HO- | O.C1(=CC=CC=C1)C | 40 | 2 | Cl.O=C(O)[C@@H](O)Cc1ccccc1>O.C1(=CC=CC=C1)C>O=C(O)[C@H](Cl)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68ea3333903c4a81957930d0868694d9 | O=C(O)[C@@H](O)Cc1ccccc1.O=S(Cl)Cl>>O=C(O)[C@H](Cl)Cc1ccccc1 | O.S(=O)(Cl)Cl.O[C@H](C(=O)O)CC1=CC=CC=C1.N1=CC=CC=C1>>Cl[C@@H](C(=O)O)CC1=CC=CC=C1 | O[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.O=S(Cl)[Cl:5]>>[O:1]=[C:2]([OH:3])[C@H:4]([Cl:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | O=C(O)[C@@H](O)Cc1ccccc1.O=S(Cl)Cl | O=C(O)[C@H](Cl)Cc1ccccc1 | null | null | C(OC)COC | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C@@H;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[Cl;H0;D1;+0:1]-[C@H;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 61 | [{"value": 61.0, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "Cl[C@@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | Thionyl chloride (0.18 ml, 2.4 mmol) was added dropwise to a solution of 200 mg (1.2 mmol) of (2S)-2-hydroxy-3-phenylpropionic acid (optical purity 100% ee (S)) in 2 ml of dimethoxyethane at room temperature, and the mixture was stirred for 15 hours. To that reaction mixture was added 0.01 ml (0.12 mmol) of pyridine, a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HCl | C(OC)COC | null | 15 | O=C(O)[C@@H](O)Cc1ccccc1.O=S(Cl)Cl>C(OC)COC>O=C(O)[C@H](Cl)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-908bddf74474441f8443475f190a40a2 | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1>>CC(=O)S[C@@H](Cc1ccccc1)C(=O)O | C(C)(=S)[O-].[K+].Cl[C@@H](C(=O)O)CC1=CC=CC=C1.S(=S)(=O)([O-])[O-].[Na+].[Na+]>>C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1 | [CH3:1][C:2]([O-:3])=[S:4].Cl[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15]>>[CH3:1][C:2](=[O:3])[S:4][C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15] | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1 | CC(=O)S[C@@H](Cc1ccccc1)C(=O)O | null | null | CN(C=O)C | Acylation | OtherReaction | fb0feb458ec3ce58113f846e0298c71e9283e4a1a2049c2d3d2f75d227413bf4 | 86068a19cdf3a43185421f62a7479868adb1c4df5f522b8ab7be3cab26d60d11 | c1ccccc1 | Cl-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[C;D1;H3:7]-[C;H0;D3;+0:8](-[O-;H0;D1:9])=[S;H0;D1;+0:10]>>[C;D1;H3:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[S;H0;D2;+0:10]-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 83.4 | [{"value": 83.0, "product": "C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Potassium thioacetate (68 mg, 0.64 mmol) was added to a solution of 100 mg (0.54 mmol) of the (2R)-2-chloro-3-phenylpropionic acid obtained in Example 14 in 2 ml of dimethylformamide at room temperature, and the mixture was stirred for 24 hours. A 6% aqueous solution of sodium thiosulfate (0.5 ml) was added to the reac... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Thiocarbonyl | Carbo-thioester | null | null | c1ccccc1 | Other | CN(C=O)C | null | 24 | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1>CN(C=O)C>CC(=O)S[C@@H](Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ac7e1c187a74ce1bb0d90b6c53ef431 | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1>>CC(=O)S[C@@H](Cc1ccccc1)C(=O)O | C(C)(=S)[O-].[K+].Cl[C@@H](C(=O)O)CC1=CC=CC=C1>>C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1 | [CH3:1][C:2]([O-:3])=[S:4].Cl[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15]>>[CH3:1][C:2](=[O:3])[S:4][C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15] | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1 | CC(=O)S[C@@H](Cc1ccccc1)C(=O)O | null | null | CN1C(CCC1)=O | Acylation | OtherReaction | fb0feb458ec3ce58113f846e0298c71e9283e4a1a2049c2d3d2f75d227413bf4 | 86068a19cdf3a43185421f62a7479868adb1c4df5f522b8ab7be3cab26d60d11 | c1ccccc1 | Cl-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[C;D1;H3:7]-[C;H0;D3;+0:8](-[O-;H0;D1:9])=[S;H0;D1;+0:10]>>[C;D1;H3:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[S;H0;D2;+0:10]-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 94.4 | [{"value": 94.0, "product": "C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.4, "product": "C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Potassium thioacetate (93 mg, 0.81 mmol) was added to a solution of 100 mg (0.54 mmol) of (2R)-2-chloro-3-phenylpropionic acid in 2 ml of N-methyl-2-pyrrolidone at room temperature, and the mixture was stirred for 24 hours. The work-up procedure in the same manner as in Example 18 of the reaction mixture was followed t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Thiocarbonyl | Carbo-thioester | null | null | c1ccccc1 | Other | CN1C(CCC1)=O | null | 24 | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1>CN1C(CCC1)=O>CC(=O)S[C@@H](Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7520f1cf780d441d8c777cb01452a67b | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1>>CC(=O)S[C@@H](Cc1ccccc1)C(=O)O | Cl.S(=S)(=O)([O-])[O-].[Na+].[Na+].Cl[C@@H](C(=O)O)CC1=CC=CC=C1.C(C)(=S)[O-].[K+]>>C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1 | [CH3:1][C:2]([O-:3])=[S:4].Cl[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15]>>[CH3:1][C:2](=[O:3])[S:4][C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15] | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1 | CC(=O)S[C@@H](Cc1ccccc1)C(=O)O | null | null | CN(C=O)C.C1(=CC=CC=C1)C | Acylation | OtherReaction | fb0feb458ec3ce58113f846e0298c71e9283e4a1a2049c2d3d2f75d227413bf4 | 86068a19cdf3a43185421f62a7479868adb1c4df5f522b8ab7be3cab26d60d11 | c1ccccc1 | Cl-[C@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[C;D1;H3:7]-[C;H0;D3;+0:8](-[O-;H0;D1:9])=[S;H0;D1;+0:10]>>[C;D1;H3:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[S;H0;D2;+0:10]-[C@@H;D3;+0:1](-[C:2]-[c:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 85 | [{"value": 85.0, "product": "C(C)(=O)S[C@H](C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | The (2R)-2-chloro-3-phenylpropionic acid obtained in Example 13, 20.0 g (108.0 ml), to a mixture of 16.1 g (141.0 mmol) of potassium thioacetate and 40 ml of dimethylformamide was added dropwise at 0° C. and the mixture was stirred at room temperature for 24 hours. To the reaction mixture were added 60 ml of 6% sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Thiocarbonyl | Carbo-thioester | null | null | c1ccccc1 | Other | CN(C=O)C.C1(=CC=CC=C1)C | null | 24 | CC([O-])=S.O=C(O)[C@H](Cl)Cc1ccccc1>CN(C=O)C.C1(=CC=CC=C1)C>CC(=O)S[C@@H](Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-180b7cd0d66e453baf7dc0724e4d95f7 | Cc1cc(C)c(C(=O)Cl)c(C)c1.Cc1ccccc1Pc1ccccc1C.OO>>Cc1cc(C)c(C(=O)P(=O)(c2ccccc2C)c2ccccc2C)c(C)c1 | OO.[Na].[Cl-].C1(=C(C=CC=C1)PC1=C(C=CC=C1)C)C.CC1=C(C(=O)Cl)C(=CC(=C1)C)C>>CC1=C(C(=O)P(C2=C(C=CC=C2)C)(C2=C(C=CC=C2)C)=O)C(=CC(=C1)C)C | Cl[C:7]([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:27][c:25]1[CH3:26])=[O:8].[PH:9]([c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[CH3:24].O[OH:10]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([C:7](=[O:8])[P:9](=[O:10])([c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH3:17])[c:18... | Cc1cc(C)c(C(=O)Cl)c(C)c1.Cc1ccccc1Pc1ccccc1C.OO | Cc1cc(C)c(C(=O)P(=O)(c2ccccc2C)c2ccccc2C)c(C)c1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ca046c3fbf68135b5038305cdccc4cc1ae2d8d095c48be86839dd14fc2833d00 | e8964f36a0b6a66028a106c5bd97ed56da7f8b50c5bfeddb45caadf3e7260c23 | O=C(c1ccccc1)P(=O)(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-[OH;D1;+0:6].[c:7]:[c:8](-[PH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[P;H0;D4;+0:9](=[O;H0;D1;+0:6])(-[c:8](:[c:7]):[c:13])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | Under argon and with exclusion of moisture, 4.6 g of chopped sodium (0.20 mol) are placed at room temperature in 100 ml of tetrahydrofuran. Stirring slowly, 24.9 g (0.10 mol) of ditolylphosphine chloride (isomeric mixture of di-ortho, di-para and ortho-para) are added dropwise at 20–25° C. After stirring for 12 h, the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Peroxide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | O1CCCC1 | null | null | Cc1cc(C)c(C(=O)Cl)c(C)c1.Cc1ccccc1Pc1ccccc1C.OO>O1CCCC1>Cc1cc(C)c(C(=O)P(=O)(c2ccccc2C)c2ccccc2C)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-916bc1de34d74789ad6be2392b25c84c | Cc1cc(C)c(C(=O)Cl)c(C)c1.ClP(c1ccccc1)c1ccccc1.OO>>Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1 | CC1=C(C(=O)Cl)C(=CC(=C1)C)C.[Li].C1=CC=CC2=CC=CC=C12.OO.ClP(C1=CC=CC=C1)C1=CC=CC=C1>>CC1=C(C(=O)P(C2=CC=CC=C2)(C2=CC=CC=C2)=O)C(=CC(=C1)C)C | Cl[C:7]([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:25][c:23]1[CH3:24])=[O:8].Cl[P:9]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.O[OH:10]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([C:7](=[O:8])[P:9](=[O:10])([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:... | Cc1cc(C)c(C(=O)Cl)c(C)c1.ClP(c1ccccc1)c1ccccc1.OO | Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | ca046c3fbf68135b5038305cdccc4cc1ae2d8d095c48be86839dd14fc2833d00 | e8964f36a0b6a66028a106c5bd97ed56da7f8b50c5bfeddb45caadf3e7260c23 | O=C(c1ccccc1)P(=O)(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-[P;H0;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12].O-[OH;D1;+0:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[P;H0;D4;+0:6](=[O;H0;D1;+0:13])(-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 10 | MINUTE | Under argon and with exclusion of moisture, 2.76 g of lithium (0.40 mol) are suspended at room temperature in 100 ml of THF and this suspension is charged with 0.10 g (0.00078 mol) of naphthalene. This mixture is then stirred for 10 minutes at room temperature. With occasional cooling and vigorous stirring, 45.2 g (0.0... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Peroxide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | 0.166667 | Cc1cc(C)c(C(=O)Cl)c(C)c1.ClP(c1ccccc1)c1ccccc1.OO>C1CCOC1>Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-943639b9c51d44ceb787ea43af14469e | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | ClS(=O)(=O)O.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C\C(=O)OC)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C/C(=O)OC)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O | CO[C:7](/[CH:6]=[C:5](\[C:3]([O:2][CH3:1])=[O:4])[O:18][c:17]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16])=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]2[o:18]1 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC | COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9384d0801651565ab66bb416179aa137f0bcb0f94958177c45a9b77d57a9c857 | c0e3e35880ade0a1551f21fe5d55ed0cd49362b919d955c9570932395b26a0c8 | O=c1ccoc2ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5... | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 6 | HOUR | A reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 250 parts by weight of chlorosulfonic acid. Thereto, 50 parts by weight of a mixture (content: 82.1% by weight, fumaric acid/maleic acid ratio=58/42) of dimethyl 2-(2-nitrophenoxy)fumarate and dimethyl 2-(2-nitrophenoxy)male... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | 70 | 6 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5644d8518a04903aeea57b173d4d671 | O=C(O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)O>>O=C(O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | ClS(=O)(=O)O.[N+](=O)([O-])C1=C(O/C(/C(=O)O)=C\C(=O)O)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)O)=C/C(=O)O)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)O)=O | O[C:6](/[CH:5]=[C:4](\[C:2](=[O:1])[OH:3])[O:17][c:16]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15])=[O:7]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]2[o:17]1 | O=C(O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)O | O=C(O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c45fe4dbc99c6805dd6c25fddc347a0cbcda70a9dc9cc8de97a3a3f087e5bd66 | 0bd39ef66a7a4f4941c6fda7c46b6c5c0a5e537ad6476ec658a74a23156fe0e7 | O=c1ccoc2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[O;D1;H0:12]=[C:11](-[O;D1;H1:13])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5]:1 | 70 | [{"value": 70.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 6 | HOUR | After a reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 25 parts by weight of chlorosulfonic acid, 5 parts by weight of a mixture (content: 65.7% by weight) containing 2-(2-nitrophenoxy)fumaric acid and 2-(2-nitrophenoxy)maleic acid was added. After that, the inner temperat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | null | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | 60 | 6 | O=C(O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)O>>O=C(O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82b9fddd628e4a618f9e86e30cf66450 | CCOC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OCC>>CCOC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | ClS(=O)(=O)O.C(\C=C\C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.[N+](=O)([O-])C1=C(O/C(/C(=O)OCC)=C\C(=O)OCC)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)OCC)=C/C(=O)OCC)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OCC)=O | CCO[C:8](/[CH:7]=[C:6](\[C:4]([O:3][CH2:2][CH3:1])=[O:5])[O:19][c:18]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17])=[O:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]2[o:19]1 | CCOC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OCC | CCOC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9384d0801651565ab66bb416179aa137f0bcb0f94958177c45a9b77d57a9c857 | c0e3e35880ade0a1551f21fe5d55ed0cd49362b919d955c9570932395b26a0c8 | O=c1ccoc2ccccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5]:1 | 70 | [{"value": 70.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 7 | HOUR | After a reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 15 parts by weight of chlorosulfonic acid, 3 parts by weight of a mixture (content: 84.4% by weight, fumaric acid/maleic acid ratio=49/51) containing diethyl 2-(2-nitrophenoxy)fumarate and diethyl 2-(2-nitrophenoxy)mal... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | 70 | 7 | CCOC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OCC>>CCOC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0e070e2ec3446a5a41e6eba8eb8baa1 | O=C(O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)O>>O=C(O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | S(O)(O)(=O)=O.[N+](=O)([O-])C1=C(O/C(/C(=O)O)=C\C(=O)O)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)O)=C/C(=O)O)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)O)=O | O[C:6](/[CH:5]=[C:4](\[C:2](=[O:1])[OH:3])[O:17][c:16]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15])=[O:7]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]2[o:17]1 | O=C(O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)O | O=C(O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c45fe4dbc99c6805dd6c25fddc347a0cbcda70a9dc9cc8de97a3a3f087e5bd66 | 0bd39ef66a7a4f4941c6fda7c46b6c5c0a5e537ad6476ec658a74a23156fe0e7 | O=c1ccoc2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[O;D1;H0:12]=[C:11](-[O;D1;H1:13])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5]:1 | 35 | [{"value": 35.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | After a reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 20 parts by weight of fuming sulfuric acid, 2 parts by weight of a mixture (content: 65.7% by weight) containing 2-(2-nitrophenoxy)fumaric acid and 2-(2-nitrophenoxy)maleic acid was added. After that, the mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | null | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | null | 2 | O=C(O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)O>>O=C(O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-072c3d9de7de4b1389dab342867a40c5 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | ClS(=O)(=O)O.C(\C=C\C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C\C(=O)OC)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C/C(=O)OC)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O | CO[C:7](/[CH:6]=[C:5](\[C:3]([O:2][CH3:1])=[O:4])[O:18][c:17]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16])=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]2[o:18]1 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC | COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9384d0801651565ab66bb416179aa137f0bcb0f94958177c45a9b77d57a9c857 | c0e3e35880ade0a1551f21fe5d55ed0cd49362b919d955c9570932395b26a0c8 | O=c1ccoc2ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5... | 86 | [{"value": 86.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | A reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 300 parts by weight of chlorosulfonic acid. Thereto, 60 parts by weight of a mixture (content: 81.1% by weight, fumaric acid/maleic acid ratio=57/43) containing dimethyl 2-(2-nitrophenoxy)fumarate and dimethyl 2-(2-nitrophen... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | 60 | 3 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9f824f0c5e2416cb52f40f910d00786 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | ClS(=O)(=O)O.S(O)(O)(=O)=O.C(\C=C\C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C\C(=O)OC)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C/C(=O)OC)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O | CO[C:7](/[CH:6]=[C:5](\[C:3]([O:2][CH3:1])=[O:4])[O:18][c:17]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16])=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]2[o:18]1 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC | COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9384d0801651565ab66bb416179aa137f0bcb0f94958177c45a9b77d57a9c857 | c0e3e35880ade0a1551f21fe5d55ed0cd49362b919d955c9570932395b26a0c8 | O=c1ccoc2ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5... | 88 | [{"value": 88.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | A reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 50.2 parts by weight of chlorosulfonic acid. Thereto, 25.1 parts by weight of 98% sulfuric acid was added dropwise over 1 hour and the mixture was then warmed to 60° C. Thereto, 25.6 parts by weight of a mixture (content: 89... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | 60 | 4 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b42345baf61644a1b75b6e3ae9158f01 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | ClS(=O)(=O)O.S(O)(O)(=O)=O.C(\C=C\C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C\C(=O)OC)C=CC=C1.[N+](=O)([O-])C1=C(O/C(/C(=O)OC)=C/C(=O)OC)C=CC=C1>>[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O | CO[C:7](/[CH:6]=[C:5](\[C:3]([O:2][CH3:1])=[O:4])[O:18][c:17]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N+:14](=[O:15])[O-:16])=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]2[o:18]1 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC | COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9384d0801651565ab66bb416179aa137f0bcb0f94958177c45a9b77d57a9c857 | c0e3e35880ade0a1551f21fe5d55ed0cd49362b919d955c9570932395b26a0c8 | O=c1ccoc2ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5... | 88 | [{"value": 88.0, "product": "[N+](=O)([O-])C1=CC=CC=2C(C=C(OC21)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | A reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 50.2 parts by weight of chlorosulfonic acid. Thereto, 25.0 parts by weight of 98% sulfuric acid was added dropwise over 1 hour and the mixture was then warmed to 60° C. Thereto, 25.3 parts by weight of the mixture (content: ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester | c1ccccc1 | c1ccc2ccccc2o1 | c1ccc2ccccc2o1 | HO- | null | 60 | 4 | COC(=O)/C=C(/Oc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)c1cc(=O)c2cccc([N+](=O)[O-])c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daa30c7028e44abdaf2b1a76d660e842 | COC(=O)/C=C(/Oc1ccc([N+](=O)[O-])cc1)C(=O)OC>>COC(=O)c1cc(=O)c2cc([N+](=O)[O-])ccc2o1 | ClS(=O)(=O)O.[N+](=O)([O-])C1=CC=C(O/C(/C(=O)OC)=C\C(=O)OC)C=C1.[N+](=O)([O-])C1=CC=C(O/C(/C(=O)OC)=C/C(=O)OC)C=C1>>[N+](=O)([O-])C=1C=CC2=C(C(C=C(O2)C(=O)OC)=O)C1 | CO[C:7](/[CH:6]=[C:5](\[C:3]([O:2][CH3:1])=[O:4])[O:18][c:17]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1)=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](=[O:8])[c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][c:17]2[o:18]1 | COC(=O)/C=C(/Oc1ccc([N+](=O)[O-])cc1)C(=O)OC | COC(=O)c1cc(=O)c2cc([N+](=O)[O-])ccc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | afbccf033d2260f46a27997e8cb11d28f0ac49520b31c0c03f124f8753acd45e | c0e3e35880ade0a1551f21fe5d55ed0cd49362b919d955c9570932395b26a0c8 | O=c1ccoc2ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[CH;D2;+0:3]=[C;H0;D3;+0:4](/[O;H0;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[o;H0;D2;+0:5... | 95 | [{"value": 95.0, "product": "[N+](=O)([O-])C=1C=CC2=C(C(C=C(O2)C(=O)OC)=O)C1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 6 | HOUR | A reaction container equipped with a stirrer, a cooling tube and a thermometer was charged with 79.3 parts by weight of chlorosulfonic acid and warmed to 60° C. Thereto 20.2 parts by weight of a mixture (content: 55.8% by weight, isomer ratio=52/48) containing dimethyl 2-(4-nitrophenoxy)fumarate and dimethyl 2-(4-nitro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester | c1ccccc1 | c1ccc2occcc2c1 | c1ccc2occcc2c1 | HO- | null | 60 | 6 | COC(=O)/C=C(/Oc1ccc([N+](=O)[O-])cc1)C(=O)OC>>COC(=O)c1cc(=O)c2cc([N+](=O)[O-])ccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c673a36413bb4095a3c1e179447fff08 | CC(C)(C)c1ccc2c(c1)Cc1cc(C(C)(C)C)cc(Br)c1-2>>Brc1cccc2c1-c1ccccc1C2 | BrC1=CC(=CC=2CC3=CC(=CC=C3C12)C(C)(C)C)C(C)(C)C.[Al+3].[Cl-].[Cl-].[Cl-]>>BrC1=CC=CC=2CC3=CC=CC=C3C12 | CC(C)(C)[c:4]1[cH:3][c:2]([Br:1])[c:7]2[c:6]([cH:5]1)[CH2:14][c:13]1[c:8]-2[cH:9][cH:10][c:11](C(C)(C)C)[cH:12]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1-[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14]2 | CC(C)(C)c1ccc2c(c1)Cc1cc(C(C)(C)C)cc(Br)c1-2 | Brc1cccc2c1-c1ccccc1C2 | null | null | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 7485c424a96c23e8b4a89284451c0507b7498ca4a7bb665380fbfafa32f39180 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(c1)Cc1ccccc1-2 | C-C(-C)(-C)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)(-C)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[cH;D2;+0:1]:[c:2]:[c:3].[c:8]:[c:7]:[cH;D2;+0:6]:[c:9]:[c:10] | null | [] | null | null | null | null | The 4-bromo-2,7-di-t-butyl-fluorene is then reacted with benzene and AlCl3 to produce 4-bromo-fluorene as follows:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | Other | C1=CC=CC=C1 | null | null | CC(C)(C)c1ccc2c(c1)Cc1cc(C(C)(C)C)cc(Br)c1-2>C1=CC=CC=C1>Brc1cccc2c1-c1ccccc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-620740ab78764f6d8422ea034b41264b | CC(C)(C)c1cc2c(cc1Br)Cc1cc(Br)c(C(C)(C)C)cc1-2.OB(O)c1ccccc1>>CC(C)(C)c1cc2c(cc1-c1ccccc1)Cc1cc(-c3ccccc3)c(C(C)(C)C)cc1-2 | BrC1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)Br.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=CC=C1)C1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)C1=CC=CC=C1 | Br[c:10]1[c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:6][c:7]2[c:8]([cH:9]1)[CH2:17][c:18]1[cH:19][c:20](Br)[c:27]([C:28]([CH3:12])([CH3:13])[CH3:31])[cH:32][c:33]1-2.OB(O)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]2[c:8]([cH:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:... | CC(C)(C)c1cc2c(cc1Br)Cc1cc(Br)c(C(C)(C)C)cc1-2.OB(O)c1ccccc1 | CC(C)(C)c1cc2c(cc1-c1ccccc1)Cc1cc(-c3ccccc3)c(C(C)(C)C)cc1-2 | 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 | CCO.O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | d481c0b3db173d545763ad3d9df9fc5e4f0d74bcfec4915fafa1a7eb453cd588 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | c1ccc(-c2ccc3c(c2)Cc2cc(-c4ccccc4)ccc2-3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8]):[c:9].Br-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[C:14]):[c:15].O-B(-O)-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[C;D1;H3:21]-[C;H0;D4;+0:5](-[C;D1;H3:22])(-[C;D1;H3:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:16]... | 179.4 | [{"value": 90.0, "product": "C1(=CC=CC=C1)C1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 179.4, "product": "C1(=CC=CC=C1)C1=CC=2CC3=CC(=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a mixture of 2,7-dibromo-3,6-di-t-butylfluorene (0.96 g, 2.20 mmol) and Pd(PPh3)4 (260 mg, 0.22 mmol) in toluene (50 ml) was added a solution of phenylboronic acid (0.81 g, 6.63 mmol) in EtOH (10 ml) and a solution of Na2CO3 (1.5 g) in water (10 ml). The reaction mixture was stirred for 6 hours under reflux. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | Br-.B | 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.CCO.O.C1(=CC=CC=C1)C | null | 6 | CC(C)(C)c1cc2c(cc1Br)Cc1cc(Br)c(C(C)(C)C)cc1-2.OB(O)c1ccccc1>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.CCO.O.C1(=CC=CC=C1)C>CC(C)(C)c1cc2c(cc1-c1ccccc1)Cc1cc(-c3ccccc3)c(C(C)(C)C)cc1-2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b5a009ec29f4539a20aacaba4de1f91 | CC(C)(C)c1ccc2c(c1)-c1cc(C(C)(C)C)c(CCl)cc1C2>>Cc1cc2c(cc1C(C)(C)C)-c1cc(C(C)(C)C)ccc1C2 | ClCC1=CC=2CC3=CC=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC1=CC=2CC3=CC=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C | Cl[CH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([CH3:9])([CH3:10])[CH3:11])-[c:12]1[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20][c:21]1[CH2:22]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]([CH3:9])([CH3:10])[CH3:11])-[c:12]1[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20][c:21]... | CC(C)(C)c1ccc2c(c1)-c1cc(C(C)(C)C)c(CCl)cc1C2 | Cc1cc2c(cc1C(C)(C)C)-c1cc(C(C)(C)C)ccc1C2 | null | null | C1CCOC1 | Functional Group Interconversion | Dehalogenation | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc2c(c1)Cc1ccccc1-2 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | 102.9 | [{"value": 102.9, "product": "CC1=CC=2CC3=CC=C(C=C3C2C=C1C(C)(C)C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-chloromethyl-3,6-di-t-butylfluorene (0.74 g, 2.26 mmol) in THF (15 ml) was added a small portion of LiAlH4 (129 mg, 3.39 mmol) under stirring and the mixture was refluxed for 5 hours. The reaction was quenched with water and NaOH and extracted with ether. The ether solution was evaporated under vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccc2c(c1)Cc1ccccc12 | Other | C1CCOC1 | null | null | CC(C)(C)c1ccc2c(c1)-c1cc(C(C)(C)C)c(CCl)cc1C2>C1CCOC1>Cc1cc2c(cc1C(C)(C)C)-c1cc(C(C)(C)C)ccc1C2 |
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