dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18221401c57e4374b9d089c4d5b209c7 | Brc1ccsc1.CC(=O)c1nc(C)oc1C>>Cc1nc(C(C)(O)c2ccsc2)c(C)o1 | BrC1=CSC=C1.C(C)(=O)C=1N=C(OC1C)C>>CC=1OC(=C(N1)C(C)(O)C1=CSC=C1)C | Br[c:8]1[cH:9][cH:10][s:11][cH:12]1.[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])=[O:7])[c:13]([CH3:14])[o:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])([OH:7])[c:8]2[cH:9][cH:10][s:11][cH:12]2)[c:13]([CH3:14])[o:15]1 | Brc1ccsc1.CC(=O)c1nc(C)oc1C | Cc1nc(C(C)(O)c2ccsc2)c(C)o1 | null | null | null | C-C Coupling | Grignard_alcohol | ced8db25e742cc856055ca33877a37cbea1e62e1ac0cab97d987f0994afc50bc | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1nc(Cc2ccsc2)co1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#8;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#8;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromothiophene and 4-acetyl-2,5-dimethyloxazole and following the general method of Example 4 the title compound was prepared. M.p. 83°-84° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1cocn1.c1ccsc1 | Br- | null | null | null | Brc1ccsc1.CC(=O)c1nc(C)oc1C>>Cc1nc(C(C)(O)c2ccsc2)c(C)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01df543a66bb4268b36a7edbe14246e3 | CC(=O)c1cc(C)oc1C.Cc1cscn1>>Cc1cc(C(C)(O)c2scnc2C)c(C)o1 | C(CCC)[Li].C(O)([O-])=O.[Na+].C[Si](C)(C)Cl.C(CCC)[Li].C(C)(=O)C1=C(OC(=C1)C)C.CC=1N=CSC1>>CC=1OC(=CC1C(C)(O)C1=C(N=CS1)C)C | [CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])=[O:7])[c:14]([CH3:15])[o:16]1.[cH:8]1[s:9][cH:10][n:11][c:12]1[CH3:13]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([OH:7])[c:8]2[s:9][cH:10][n:11][c:12]2[CH3:13])[c:14]([CH3:15])[o:16]1 | CC(=O)c1cc(C)oc1C.Cc1cscn1 | Cc1cc(C(C)(O)c2scnc2C)c(C)o1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | acd195ea3234757fa63ebadb8d31a476ea220e3bfd4b639c71b1e4fe8ddfd859 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1cc(Cc2cncs2)co1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[cH;D2;+0:6]:1.[C;D1;H3:7]-[c:8]1:[#8;a:9]:[c:10]:[c:11]:[c:12]:1-[C;H0;D3;+0:13](-[C;D1;H3:14])=[O;H0;D1;+0:15]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[OH;D1;+0:15])-[c:12]1:[c:11]:[c:10]:[#8;a:9]:[c:8]:1-[C;D1;H3:7] | null | [] | -70 | CELSIUS | 1 | HOUR | 4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cscn1 | c1cscn1 | c1ccoc1.c1cscn1 | null | O1CCCC1 | -70 | 1 | CC(=O)c1cc(C)oc1C.Cc1cscn1>O1CCCC1>Cc1cc(C(C)(O)c2scnc2C)c(C)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a210beaddfb84e2bacb0459a8fb6e751 | CC(=O)c1ccco1.Cc1cscn1>>Cc1ncsc1C(C)(O)c1ccco1 | CC=1N=CSC1.C(C)(=O)C=1OC=CC1>>O1C(=CC=C1)C(C)(O)C1=C(N=CS1)C | [C:7]([CH3:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][o:14]1.[CH3:1][c:2]1[n:3][cH:4][s:5][cH:6]1>>[CH3:1][c:2]1[n:3][cH:4][s:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][cH:13][o:14]1 | CC(=O)c1ccco1.Cc1cscn1 | Cc1ncsc1C(C)(O)c1ccco1 | null | null | null | C-C Coupling | OtherReaction | acd195ea3234757fa63ebadb8d31a476ea220e3bfd4b639c71b1e4fe8ddfd859 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1coc(Cc2cncs2)c1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[#8;a:6]:[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[cH;D2;+0:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[c;H0;D3;+0:13]:1-[C;H0;D4;+0:2](-[C;D1;H3:1])(-[OH;D1;+0:3])-[c:4](:[c:5]):[#8;a:6]:[c:7] | null | [] | null | null | null | null | Starting with 4-methylthiazole and 2-acetylfuran and following the general method of Example 15 the title compound was prepared. M.p. 127°-128° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cscn1 | c1cscn1 | c1cscn1.c1ccoc1 | null | null | null | null | CC(=O)c1ccco1.Cc1cscn1>>Cc1ncsc1C(C)(O)c1ccco1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5c6c64398c34e29931916d91cb3bfd4 | CC(=O)c1cccs1.Cc1cscn1>>Cc1ncsc1C(C)(O)c1cccs1 | CC=1N=CSC1.C(C)(=O)C=1SC=CC1>>CC=1N=CSC1C(C)(O)C=1SC=CC1 | [C:7]([CH3:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][s:14]1.[CH3:1][c:2]1[n:3][cH:4][s:5][cH:6]1>>[CH3:1][c:2]1[n:3][cH:4][s:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][cH:13][s:14]1 | CC(=O)c1cccs1.Cc1cscn1 | Cc1ncsc1C(C)(O)c1cccs1 | null | null | null | C-C Coupling | OtherReaction | acd195ea3234757fa63ebadb8d31a476ea220e3bfd4b639c71b1e4fe8ddfd859 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1csc(Cc2cncs2)c1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[cH;D2;+0:13]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[c;H0;D3;+0:13]:1-[C;H0;D4;+0:2](-[C;D1;H3:1])(-[OH;D1;+0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7] | null | [] | null | null | null | null | Starting with 4-methylthiazole and 2-acetylthiophene and following the general method of Example 15 the title compound was prepared. M.p. 146.5°-147.5° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cscn1 | c1cscn1 | c1cscn1.c1ccsc1 | null | null | null | null | CC(=O)c1cccs1.Cc1cscn1>>Cc1ncsc1C(C)(O)c1cccs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7674ce8e93ec4e02859f77b6a1662375 | CC(=O)c1ccsc1.C[Si](C)(C)c1nccs1>>CC(O)(c1ccsc1)c1cncs1 | C(O)([O-])=O.[Na+].C(C)(=O)C1=CSC=C1.C(CCC)[Li].C[Si](C=1SC=CN1)(C)C>>S1C=NC=C1C(C)(O)C1=CSC=C1 | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][s:7][cH:8]1.C[Si](C)(C)[c:12]1[n:11][cH:10][cH:9][s:13]1>>[CH3:1][C:2]([OH:3])([c:4]1[cH:5][cH:6][s:7][cH:8]1)[c:9]1[cH:10][n:11][cH:12][s:13]1 | CC(=O)c1ccsc1.C[Si](C)(C)c1nccs1 | CC(O)(c1ccsc1)c1cncs1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 5a13a76517abc481d18e323a5c6c18a4e7b3154319796cea55453b7d5b071d2c | ba292e2f26094ec157e2ffb4e80ae84c33cd53ebd701e5703ae56960fea8e68f | c1cc(Cc2cncs2)cs1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[cH;D2;+0:3]:[c:4]:[#7;a:5]:1.[C;D1;H3:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9]1:[c:10]:[c:11]:[#16;a:12]:[c:13]:1>>[C;D1;H3:6]-[C;H0;D4;+0:7](-[OH;D1;+0:8])(-[c:9]1:[c:10]:[c:11]:[#16;a:12]:[c:13]:1)-[c;H0;D3;+0:3]1:[#16;a:2]:[cH;D2;+0:1]:[#7;a:5]:[c:4]:1 | null | [] | null | null | 45 | MINUTE | n-Butyllithium (2.5M solution in hexane, 5.6 ml) in diethylether (25 ml) was stirred at -70° C. under a nitrogen atmosphere and 2-trimethylsilylthiazole (2 g) in diethylether (25 ml) was added dropwise. After 30 minutes 3-acetylthiophene (1.93 g) in diethylether (25 ml) was added dropwise. After a further 45 minutes th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Silyl protective group | Tertiary alcohol | c1cscn1 | c1cscn1 | c1ccsc1.c1cscn1 | Other | C(C)OCC | null | 0.75 | CC(=O)c1ccsc1.C[Si](C)(C)c1nccs1>C(C)OCC>CC(O)(c1ccsc1)c1cncs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8ae87d4cdb04743b3be2fcbfdc05511 | Cc1ncoc1C(C)(O)c1ccoc1>>C=C(c1ccoc1)c1ocnc1C | C(O)([O-])=O.[Na+].O1C=C(C=C1)C(C)(O)C1=C(N=CO1)C.Cl.C(C)OCC>>O1C=C(C=C1)C(=C)C1=C(N=CO1)C | O[C:2]([CH3:1])([c:3]1[cH:4][cH:5][o:6][cH:7]1)[c:8]1[o:9][cH:10][n:11][c:12]1[CH3:13]>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][o:6][cH:7]1)[c:8]1[o:9][cH:10][n:11][c:12]1[CH3:13] | Cc1ncoc1C(C)(O)c1ccoc1 | C=C(c1ccoc1)c1ocnc1C | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 2308ca9261cc4508224f0a5bf7cda8624f4e05d90876372dcc82c257ed89c11a | eea2743fbea38c6dcccd1d257095859a33500c4f909c86118b5a2f77112ebdea | C=C(c1ccoc1)c1cnco1 | O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1)-[c:8]1:[#8;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[C;D1;H3:13]>>[C;D1;H3:13]-[c:12]1:[#7;a:11]:[c:10]:[#8;a:9]:[c:8]:1-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1 | null | [] | null | null | 10 | MINUTE | 1-(3-Furyl)-1-(4-methyl-5-oxazolyl)ethanol (900 mg) in dry chloroform was treated with 1M anhydrous hydrogen chloride in diethylether (1.1 equivalents). After 10 minutes at room temperature, aqueous sodium hydrogen carbonate was added and the mixture was extracted with dichloromethane. The material thus obtained was pu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Vinyl | null | null | c1ccoc1.c1cocn1 | HO- | C(Cl)(Cl)Cl | null | 0.166667 | Cc1ncoc1C(C)(O)c1ccoc1>C(Cl)(Cl)Cl>C=C(c1ccoc1)c1ocnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9563069ad89e455ea5d20776f1f48877 | COC(C)(c1ccoc1)c1oc(C)nc1C>>C=C(c1ccoc1)c1oc(C)nc1C | CC=1OC(=C(N1)C)C(C)(OC)C1=COC=C1.Cl>>Cl.CC=1OC(=C(N1)C)C(=C)C1=COC=C1 | CO[C:2]([CH3:1])([c:3]1[cH:4][cH:5][o:6][cH:7]1)[c:8]1[o:9][c:10]([CH3:11])[n:12][c:13]1[CH3:14]>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][o:6][cH:7]1)[c:8]1[o:9][c:10]([CH3:11])[n:12][c:13]1[CH3:14] | COC(C)(c1ccoc1)c1oc(C)nc1C | C=C(c1ccoc1)c1oc(C)nc1C | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | ed5ebc279b9b9a90d76d9bfdf51247e16a646652657fa7c19d4e0abb0d5fb866 | ad641e1d0d5bc929f413157ac3f03f6855b2543026034902e6df156b88622b6d | C=C(c1ccoc1)c1cnco1 | C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1)-[c:8]1:[#8;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[C;D1;H3:13]>>[C;D1;H3:13]-[c:12]1:[#7;a:11]:[c:10]:[#8;a:9]:[c:8]:1-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1 | null | [] | null | null | null | null | 1-(2,4-Dimethyl-5-oxazolyl)-1-(3-furyl)-1-methoxyethane (790 mg) in dry diethylether was treated with 1M anhydrous hydrogen chloride in diethylether (1.2 equivalents). The title compound was obtained as a white solid which was filtered off, washed and dried. M.p. 128.5°-130° C.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Vinyl | null | null | c1ccoc1.c1cocn1 | HO- | C(C)OCC | null | null | COC(C)(c1ccoc1)c1oc(C)nc1C>C(C)OCC>C=C(c1ccoc1)c1oc(C)nc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a2eac6693d1472983219b852d6d0ec0 | CC(=O)c1ocnc1C.[Li][c]1ccco1>>Cc1ncoc1C(C)(O)c1ccco1 | C(C)(=O)C1=C(N=CO1)C.[Li]C=1OC=CC1>>O1C(=CC=C1)C(C)(O)C1=C(N=CO1)C | [CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])=[O:9].[Li][c:10]1[cH:11][cH:12][cH:13][o:14]1>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][cH:13][o:14]1 | CC(=O)c1ocnc1C.[Li][c]1ccco1 | Cc1ncoc1C(C)(O)c1ccco1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 8ba84549b458a473bed1ce3f130210aec377300d749c212d5b3208f8322a4467 | 1ce2a90fc82c66bb25293f8dd2f68813821f177fdf0916a1c51bb26296b4d38b | c1coc(Cc2cnco2)c1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9].[Li]-[c;H0;D3;+0:10]1:[#8;a:11]:[c:12]:[c:13]:[c:14]:1>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;H0;D4;+0:7](-[C;D1;H3:8])(-[OH;D1;+0:9])-[c;H0;D3;+0:10]1:[#8;a:11]:[c:12]:[c:13]:[c:14]:1 | null | [] | null | null | 8 | HOUR | 5-Acetyl-4-methyloxazole (4 g) in dry diethylether was added dropwise to a stirred solution of 2-lithiofuran (1 equivalent) in diethylether at -20° C. The mixture was allowed to warm to room temperature and was then left overnight. Work-up and flash chromatography then gave the title compound as a white solid, m.p. 73°... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aryl lithium | Tertiary alcohol | c1ccoc1 | c1ccoc1 | c1cocn1.c1ccoc1 | Li | C(C)OCC | null | 8 | CC(=O)c1ocnc1C.[Li][c]1ccco1>C(C)OCC>Cc1ncoc1C(C)(O)c1ccco1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64a5fb908811427eb165211883741e3d | CC(=O)c1sc(C)nc1C.[Li][c]1cccnc1>>Cc1nc(C)c(C(C)(O)c2cccnc2)s1 | C(C)(=O)C1=C(N=C(S1)C)C.[Li]C=1C=NC=CC1.C(O)([O-])=O.[Na+]>>CC=1SC(=C(N1)C)C(C)(O)C=1C=NC=CC1 | [CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])=[O:9])[s:16]1.[Li][c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])([OH:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[s:16]1 | CC(=O)c1sc(C)nc1C.[Li][c]1cccnc1 | Cc1nc(C)c(C(C)(O)c2cccnc2)s1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 8d05c101695e22ee37904717b9f3b8f3de2597fa76d2b14d2a001428eddaf89c | 1ce2a90fc82c66bb25293f8dd2f68813821f177fdf0916a1c51bb26296b4d38b | c1cncc(Cc2cncs2)c1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;H0;D1;+0:9].[Li]-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D4;+0:7](-[C;D1;H3:8])(-[OH;D1;+0:9])-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1 | null | [] | null | null | 3 | HOUR | 5-Acetyl-2,4-dimethylthiazole (2.5 g) in dry diethylether (10 ml) was added dropwise to a stirred solution of 3-lithiopyridine (from 3.5 g 3-bromopyridine) in diethylether at -70° C. After 3 hours the mixture was allowed to warm to room temperature. After a further 1 hour, aqueous sodium hydrogen carbonate was added an... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aryl lithium | Tertiary alcohol | c1ccncc1 | c1ccncc1 | c1cscn1.c1ccncc1 | Li | C(C)OCC | null | 3 | CC(=O)c1sc(C)nc1C.[Li][c]1cccnc1>C(C)OCC>Cc1nc(C)c(C(C)(O)c2cccnc2)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9af96c4c69f344379ebe313338e1ebf0 | Brc1ccsc1.CC(=O)c1c(C)noc1C>>Cc1noc(C)c1C(C)(O)c1ccsc1 | C(C)(=O)C=1C(=NOC1C)C.BrC1=CSC=C1>>CC1=NOC(=C1C(C)(O)C1=CSC=C1)C | Br[c:11]1[cH:12][cH:13][s:14][cH:15]1.[CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[C:8]([CH3:9])=[O:10]>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[C:8]([CH3:9])([OH:10])[c:11]1[cH:12][cH:13][s:14][cH:15]1 | Brc1ccsc1.CC(=O)c1c(C)noc1C | Cc1noc(C)c1C(C)(O)c1ccsc1 | null | null | null | C-C Coupling | Grignard_alcohol | ced8db25e742cc856055ca33877a37cbea1e62e1ac0cab97d987f0994afc50bc | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cc(Cc2cnoc2)cs1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#8;a:9]:[c:10](-[C;D1;H3:11]):[c:12]:1-[C;H0;D3;+0:13](-[C;D1;H3:14])=[O;H0;D1;+0:15]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[#8;a:9]:[c:10](-[C;D1;H3:11]):[c:12]:1-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[OH;D1;+0:15])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c... | null | [] | null | null | null | null | The title compound was prepared following the general method of Example 4 but starting with 4-acetyl-3,5-dimethylisoxazole and 3-bromothiophene.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1cnoc1.c1ccsc1 | Br- | null | null | null | Brc1ccsc1.CC(=O)c1c(C)noc1C>>Cc1noc(C)c1C(C)(O)c1ccsc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-59fd6eb77b07405893186404a2c88e70 | CI.Cc1nc(C)c(C(C)(O)c2ccoc2)o1>>COC(C)(c1ccoc1)c1oc(C)nc1C | C(O)([O-])=O.[Na+].O1C=C(C=C1)C(C)(O)C1=C(N=C(O1)C)C.[H-].[Na+].CI>>COC(C)(C1=COC=C1)C1=C(N=C(O1)C)C | I[CH3:1].[OH:2][C:3]([CH3:4])([c:5]1[cH:6][cH:7][o:8][cH:9]1)[c:10]1[o:11][c:12]([CH3:13])[n:14][c:15]1[CH3:16]>>[CH3:1][O:2][C:3]([CH3:4])([c:5]1[cH:6][cH:7][o:8][cH:9]1)[c:10]1[o:11][c:12]([CH3:13])[n:14][c:15]1[CH3:16] | CI.Cc1nc(C)c(C(C)(O)c2ccoc2)o1 | COC(C)(c1ccoc1)c1oc(C)nc1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | cd10a9010f842ab825b304bd2965f17f9c39c4c64e5fc6cd91306ae51817de0d | 9271b713ded6954f3329c61a211042ac37c82b3aff1b62cb455035e69339dd27 | c1cc(Cc2cnco2)co1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]:[c:4](-[C:5](-[C;D1;H3:6])(-[OH;D1;+0:7])-[c:8]:[c:9]:[#8;a:10]):[#8;a:11]>>[#7;a:2]:[c:3]:[c:4](-[C:5](-[C;D1;H3:6])(-[O;H0;D2;+0:7]-[CH3;D1;+0:1])-[c:8]:[c:9]:[#8;a:10]):[#8;a:11] | null | [] | null | null | 20 | MINUTE | 1-(3-Furyl)-1-(2,4-dimethyl-5-oxazolyl)ethanol (2g) in dry N,N-dimethylformamide (15 ml) was added to a stirred suspension of sodium hydride (80%, 300 mg) in dry N,N-dimethylformamide (10 ml) at 0° C. After 20 minutes, methyl iodide (1.5 g) was added dropwise. The mixture was allowed to warm to room temperature and aft... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Ether | null | null | c1ccoc1.c1cocn1 | HI | CN(C=O)C | null | 0.333333 | CI.Cc1nc(C)c(C(C)(O)c2ccoc2)o1>CN(C=O)C>COC(C)(c1ccoc1)c1oc(C)nc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b8d6ab59a04244b59a32293274773631 | CC(=O)c1cccs1.Cc1ncsc1C>>Cc1nc(C(C)(O)c2cccs2)sc1C | C(C)(=O)C=1SC=CC1.C(CCC)[Li].CC=1N=CSC1C>>CC=1N=C(SC1C)C(C)(O)C=1SC=CC1 | [C:5]([CH3:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][s:12]1.[CH3:1][c:2]1[n:3][cH:4][s:13][c:14]1[CH3:15]>>[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])([OH:7])[c:8]2[cH:9][cH:10][cH:11][s:12]2)[s:13][c:14]1[CH3:15] | CC(=O)c1cccs1.Cc1ncsc1C | Cc1nc(C(C)(O)c2cccs2)sc1C | null | null | C(C)OCC | C-C Coupling | OtherReaction | acd195ea3234757fa63ebadb8d31a476ea220e3bfd4b639c71b1e4fe8ddfd859 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1csc(Cc2nccs2)c1 | [#16;a:1]1:[c:2]:[c:3]:[#7;a:4]:[cH;D2;+0:5]:1.[C;D1;H3:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[#16;a:11]:[c:12]>>[C;D1;H3:6]-[C;H0;D4;+0:7](-[OH;D1;+0:8])(-[c:9](:[c:10]):[#16;a:11]:[c:12])-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[#7;a:4]:1 | null | [] | null | null | 30 | MINUTE | n-Butyllithium (2.5M solution in hexanes, 9.7 ml) was added dropwise to a stirred solution of 4,5-dimethylthiazole (2.5 g) in dry diethyl ether (30 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylthiophene (3.1 g) in diethyl ether (20 ml) was added dropwise. After a further 1 hour the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cscn1 | c1cscn1 | c1cscn1.c1ccsc1 | null | C(C)OCC | null | 0.5 | CC(=O)c1cccs1.Cc1ncsc1C>C(C)OCC>Cc1nc(C(C)(O)c2cccs2)sc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47117198c8d046e0b5bd18f8ec9abb21 | Cc1cscn1.O=C(CCCCl)c1cccs1>>Cc1csc(C2(c3cccs3)CCCO2)n1 | CC=1N=CSC1.ClCCCC(=O)C=1SC=CC1>>CC=1N=C(SC1)C1(OCCC1)C=1SC=CC1 | [CH3:1][c:2]1[cH:3][s:4][cH:5][n:16]1.Cl[CH2:14][CH2:13][CH2:12][C:6]([c:7]1[cH:8][cH:9][cH:10][s:11]1)=[O:15]>>[CH3:1][c:2]1[cH:3][s:4][c:5]([C:6]2([c:7]3[cH:8][cH:9][cH:10][s:11]3)[CH2:12][CH2:13][CH2:14][O:15]2)[n:16]1 | Cc1cscn1.O=C(CCCCl)c1cccs1 | Cc1csc(C2(c3cccs3)CCCO2)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4ba89a1e75cd3cfd3160711124195e0db992f60c52150da9ca11cc10e8e21b21 | 98d62a2f88bda9a16db724874a7a21c7201c15ae486e75d3477ada88c887a7ad | c1csc(C2(c3nccs3)CCCO2)c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c:6](:[c:7]):[#16;a:8]:[c:9].[#16;a:10]1:[c:11]:[c:12]:[#7;a:13]:[cH;D2;+0:14]:1>>[c:9]:[#16;a:8]:[c:6](-[C;H0;D4;+0:4]1(-[c;H0;D3;+0:14]2:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:2)-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-1):[c:7] | null | [] | null | null | null | null | The title compound was prepared from 4-methylthiazole and 4-chloro-1-(2-thienyl)-1-butanone, using the general method of Example 36. M.p. 59°-60° C., 13C Nmr (CDCl3) 17.4, 26.2, 41.2, 69.3, 86.2, 113.9, 124.2, 124.7, 126.8, 148.9, 153.1 and 175.6 ppm.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ether | c1cscn1 | c1cscn1.C1CCOC1 | c1cscn1.c1ccsc1.C1CCOC1 | HCl | null | null | null | Cc1cscn1.O=C(CCCCl)c1cccs1>>Cc1csc(C2(c3cccs3)CCCO2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c11173c9d7a4647bd65210ad622b55b | CC(=O)c1cc2ccccc2o1.Cc1csc([Si](C)(C)C)n1>>Cc1ncsc1C(C)(O)c1cc2ccccc2o1 | C(C)(=O)C=1OC2=C(C1)C=CC=C2.C(CCC)[Li].CC=1N=C(SC1)[Si](C)(C)C>>O1C(=CC2=C1C=CC=C2)C(C)(O)C2=C(N=CS2)C | [C:7]([CH3:8])(=[O:9])[c:10]1[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[o:18]1.C[Si](C)(C)[c:4]1[n:3][c:2]([CH3:1])[cH:6][s:5]1>>[CH3:1][c:2]1[n:3][cH:4][s:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[o:18]1 | CC(=O)c1cc2ccccc2o1.Cc1csc([Si](C)(C)C)n1 | Cc1ncsc1C(C)(O)c1cc2ccccc2o1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 5a13a76517abc481d18e323a5c6c18a4e7b3154319796cea55453b7d5b071d2c | ba292e2f26094ec157e2ffb4e80ae84c33cd53ebd701e5703ae56960fea8e68f | c1ccc2oc(Cc3cncs3)cc2c1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[cH;D2;+0:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:1.[C;D1;H3:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[#8;a:12]:[c:13]>>[C;D1;H3:5]-[c:4]1:[#7;a:6]:[cH;D2;+0:1]:[#16;a:2]:[c;H0;D3;+0:3]:1-[C;H0;D4;+0:8](-[C;D1;H3:7])(-[OH;D1;+0:9])-[c:10](:[c:11]):[#8;a:12]:[c:13] | null | [] | null | null | 30 | MINUTE | n-Butyllithium (2.5M solution in hexane, 1 equivalent) was added dropwise to a solution of 4-methyl-2-trimethylsilylthiazole (1 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylbenzofuran (1 equivalent) in diethyl ether was added. After 1 hour the mixture was al... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Silyl protective group | Tertiary alcohol | c1cscn1 | c1cscn1 | c1cscn1.c1ccc2occc2c1 | Other | C(C)OCC | null | 0.5 | CC(=O)c1cc2ccccc2o1.Cc1csc([Si](C)(C)C)n1>C(C)OCC>Cc1ncsc1C(C)(O)c1cc2ccccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6b8bc5eaf364257b6235f60aa86b148 | CC(=O)c1ccco1.Cc1nn(C)c(C)c1Br>>Cc1nn(C)c(C)c1C(C)(O)c1ccco1 | BrC=1C(=NN(C1C)C)C.C(C)(=O)C=1OC=CC1>>O1C(=CC=C1)C(C)(O)C=1C(=NN(C1C)C)C | [C:9]([CH3:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][o:16]1.Br[c:8]1[c:2]([CH3:1])[n:3][n:4]([CH3:5])[c:6]1[CH3:7]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([CH3:7])[c:8]1[C:9]([CH3:10])([OH:11])[c:12]1[cH:13][cH:14][cH:15][o:16]1 | CC(=O)c1ccco1.Cc1nn(C)c(C)c1Br | Cc1nn(C)c(C)c1C(C)(O)c1ccco1 | null | null | null | C-C Coupling | Grignard_alcohol | 867b05745a50e050669540e95bb7b56f7649cafafd59c323b0fc7ce5fb8c5702 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1coc(Cc2cn[nH]c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[#7;a:4]:[#7;a:5](-[C;D1;H3:6]):[c:7]:1-[C;D1;H3:8].[C;D1;H3:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[#8;a:14]:[c:15]>>[C;D1;H3:9]-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[c:12](:[c:13]):[#8;a:14]:[c:15])-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[#7;a:4]:[#7;a:5](-[C;D1;H3:6]):[c... | null | [] | null | null | null | null | 4-Bromo-1,3,5-trimethylpyrazole was converted into the corresponding 4-lithio compound which was then reacted in situ with 2-acetylfuran.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccoc1 | Br- | null | null | null | CC(=O)c1ccco1.Cc1nn(C)c(C)c1Br>>Cc1nn(C)c(C)c1C(C)(O)c1ccco1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9e8f852e5b4a473880332d65fd05ff5a | C[Si](C)(C)C(F)(F)F.Cc1nc(C)c(C(=O)c2ccoc2)o1>>Cc1nc(C)c(C(O)(c2ccoc2)C(F)(F)F)o1 | Cl.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1C=C(C=C1)C(=O)C1=C(N=C(O1)C)C.FC(F)(F)[Si](C)(C)C.C(O)([O-])=O.[Na+]>>CC=1OC(=C(N1)C)C(C(F)(F)F)(O)C1=COC=C1 | C[Si](C)(C)[C:14]([F:15])([F:16])[F:17].[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][o:12][cH:13]2)[o:18]1>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][o:12][cH:13]2)[C:14]([F:15])([F:16])[F:17])[o:18]1 | C[Si](C)(C)C(F)(F)F.Cc1nc(C)c(C(=O)c2ccoc2)o1 | Cc1nc(C)c(C(O)(c2ccoc2)C(F)(F)F)o1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | dfa995a1ded6b569a532c6523aafcfe2cc62e0013499fd31224672ecb3516b9f | 2ce208121d6571fcaa14b1a3313dc208052e5b2c9201de548c57a6101c962912 | c1cc(Cc2cnco2)co1 | C-[Si](-C)(-C)-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[F;D1;H0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#8;a:9]:[c:10]:1-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13]1:[c:14]:[c:15]:[#8;a:16]:[c:17]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#8;a:9]:[c:10]:1-[C;H0;D4;+0:11](-[OH;D1;+0:12])(-[c:13]1:[c:14]:[c:15]:[#8;a:16]:[c:17... | null | [] | null | null | null | null | Tetrabutylammonium fluoride (250 mg) was added to a stirred solution of 2,4-dimethyl-5-oxazolyl 3-furyl ketone (1.7 g) and (trifluoromethyl) trimethylsilane (1.9 g) in dry tetrahydrofuran (30 ml) at -10° C. The mixture was allowed to warm to room temperature. After 45 minutes 6M hydrochloric acid (30 ml) was added. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ketone.Silyl protective group | Trifluoro group.Tertiary alcohol | null | null | c1cocn1.c1ccoc1 | Other | O1CCCC1 | null | null | C[Si](C)(C)C(F)(F)F.Cc1nc(C)c(C(=O)c2ccoc2)o1>O1CCCC1>Cc1nc(C)c(C(O)(c2ccoc2)C(F)(F)F)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a84f7dd10911495d860973d4009ad6f3 | CC(=O)c1sc(C)nc1C.Cn1cccc1>>Cc1nc(C)c(C(C)(O)c2cccn2C)s1 | C(C)(=O)C1=C(N=C(S1)C)C.CN(C)CCN(C)C.C(CCC)[Li].CN1C=CC=C1>>CC=1SC(=C(N1)C)C(C)(O)C=1N(C=CC1)C | [CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])=[O:9])[s:16]1.[cH:10]1[cH:11][cH:12][cH:13][n:14]1[CH3:15]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])([OH:9])[c:10]2[cH:11][cH:12][cH:13][n:14]2[CH3:15])[s:16]1 | CC(=O)c1sc(C)nc1C.Cn1cccc1 | Cc1nc(C)c(C(C)(O)c2cccn2C)s1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 74a7a57737bc3a3f8ff699a520b9acb98d9fd2843b33b3d885ba3bc512a8ff74 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1c[nH]c(Cc2cncs2)c1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.[C;D1;H3:7]-[c:8]1:[#7;a:9]:[c:10]:[#16;a:11]:[c:12]:1-[C;H0;D3;+0:13](-[C;D1;H3:14])=[O;H0;D1;+0:15]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[OH;D1;+0:15])-[c:12]1:[#16;a:11]:[c:10]:[#7;a:9]:[c:8]:1-[C;D1;H3:7] | null | [] | null | null | 5 | MINUTE | n-Butyllithium (2.5M solution in hexanes, 20 ml) in dry diethyl ether was cooled to -70° C. under dry nitrogen and TMEDA (5.8 g) was added. After 5 minutes, 1-methylpyrrole (5.4 g) in diethyl ether was added dropwise. After a further 15 minutes, 5-acetyl-2,4-dimethylthiazole (4.5 ml) was added dropwise. After 30 minute... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cc[nH]c1 | c1ccc[nH]1 | c1cscn1.c1ccc[nH]1 | null | C(C)OCC | null | 0.083333 | CC(=O)c1sc(C)nc1C.Cn1cccc1>C(C)OCC>Cc1nc(C)c(C(C)(O)c2cccn2C)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a5eb6ad04954fd4aa68e9d330119b48 | CC(=O)c1ccsc1.Cc1ncsc1CCO>>Cc1nc(C(C)(O)c2ccsc2)sc1CCO | C(C)(=O)C1=CSC=C1.C(CCC)[Li].OCCC1=C(N=CS1)C>>OCCC1=C(N=C(S1)C(C)(O)C1=CSC=C1)C | [C:5]([CH3:6])(=[O:7])[c:8]1[cH:9][cH:10][s:11][cH:12]1.[CH3:1][c:2]1[n:3][cH:4][s:13][c:14]1[CH2:15][CH2:16][OH:17]>>[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])([OH:7])[c:8]2[cH:9][cH:10][s:11][cH:12]2)[s:13][c:14]1[CH2:15][CH2:16][OH:17] | CC(=O)c1ccsc1.Cc1ncsc1CCO | Cc1nc(C(C)(O)c2ccsc2)sc1CCO | null | null | O1CCCC1 | C-C Coupling | OtherReaction | acd195ea3234757fa63ebadb8d31a476ea220e3bfd4b639c71b1e4fe8ddfd859 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1csc(Cc2ccsc2)n1 | [#16;a:1]1:[c:2]:[c:3]:[#7;a:4]:[cH;D2;+0:5]:1.[C;D1;H3:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9]1:[c:10]:[#16;a:11]:[c:12]:[c:13]:1>>[C;D1;H3:6]-[C;H0;D4;+0:7](-[OH;D1;+0:8])(-[c:9]1:[c:10]:[#16;a:11]:[c:12]:[c:13]:1)-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[#7;a:4]:1 | null | [] | null | null | 30 | MINUTE | n-Butyllithium (2.5M solution in hexanes, 75 mmoles) was added to a stirred solution of 5-(2-hydroxyethyl)-4-methylthiazole (35 mmoles) in dry tetrahydrofuran (80 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 3-acetylthiophene (38 mmoles) in dry tetrahydrofuran (10 ml) was added dropwise. After ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cscn1 | c1cscn1 | c1cscn1.c1ccsc1 | null | O1CCCC1 | null | 0.5 | CC(=O)c1ccsc1.Cc1ncsc1CCO>O1CCCC1>Cc1nc(C(C)(O)c2ccsc2)sc1CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-19e5e84795b74736b737dbe52b48c69c | CC(=O)c1oc(C)nc1C.[Li][c]1cocc1Br>>Cc1nc(C)c(C(C)(O)c2cocc2Br)o1 | C(C)(=O)C1=C(N=C(O1)C)C.BrC=1C(=COC1)[Li]>>BrC=1C(=COC1)C(C)(O)C1=C(N=C(O1)C)C | [CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])=[O:9])[o:16]1.[Li][c:10]1[cH:11][o:12][cH:13][c:14]1[Br:15]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])([OH:9])[c:10]2[cH:11][o:12][cH:13][c:14]2[Br:15])[o:16]1 | CC(=O)c1oc(C)nc1C.[Li][c]1cocc1Br | Cc1nc(C)c(C(C)(O)c2cocc2Br)o1 | null | null | null | C-C Coupling | OtherReaction | 8ba84549b458a473bed1ce3f130210aec377300d749c212d5b3208f8322a4467 | 1ce2a90fc82c66bb25293f8dd2f68813821f177fdf0916a1c51bb26296b4d38b | c1cc(Cc2cnco2)co1 | [Br;D1;H0:1]-[c:2]1:[c:3]:[#8;a:4]:[c:5]:[c;H0;D3;+0:6]:1-[Li].[C;D1;H3:7]-[c:8]1:[#7;a:9]:[c:10]:[#8;a:11]:[c:12]:1-[C;H0;D3;+0:13](-[C;D1;H3:14])=[O;H0;D1;+0:15]>>[Br;D1;H0:1]-[c:2]1:[c:3]:[#8;a:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:13](-[C;D1;H3:14])(-[OH;D1;+0:15])-[c:12]1:[#8;a:11]:[c:10]:[#7;a:9]:[c:8]:1-[C;D1;H3... | null | [] | null | null | null | null | Following the general method of Example la but using 5-acetyl-2,4-dimethyloxazole and 4-bromo-3-lithiofuran (Liebigs Ann. Chem., 1986, 625-637), the title compound was prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aryl lithium | Tertiary alcohol | c1ccoc1 | c1ccoc1 | c1cocn1.c1ccoc1 | Li | null | null | null | CC(=O)c1oc(C)nc1C.[Li][c]1cocc1Br>>Cc1nc(C)c(C(C)(O)c2cocc2Br)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c91163ae137242d2923ab319d4372fc6 | CC(=O)c1ccsc1.COCc1scnc1C>>COCc1sc(C(C)(O)c2ccsc2)nc1C | C(C)(=O)C1=CSC=C1.COCC1=C(N=CS1)C>>COCC1=C(N=C(S1)C(C)(O)C1=CSC=C1)C | [C:7]([CH3:8])(=[O:9])[c:10]1[cH:11][cH:12][s:13][cH:14]1.[CH3:1][O:2][CH2:3][c:4]1[s:5][cH:6][n:15][c:16]1[CH3:17]>>[CH3:1][O:2][CH2:3][c:4]1[s:5][c:6]([C:7]([CH3:8])([OH:9])[c:10]2[cH:11][cH:12][s:13][cH:14]2)[n:15][c:16]1[CH3:17] | CC(=O)c1ccsc1.COCc1scnc1C | COCc1sc(C(C)(O)c2ccsc2)nc1C | null | null | null | C-C Coupling | OtherReaction | acd195ea3234757fa63ebadb8d31a476ea220e3bfd4b639c71b1e4fe8ddfd859 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1csc(Cc2ccsc2)n1 | [#16;a:1]1:[c:2]:[c:3]:[#7;a:4]:[cH;D2;+0:5]:1.[C;D1;H3:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9]1:[c:10]:[c:11]:[#16;a:12]:[c:13]:1>>[C;D1;H3:6]-[C;H0;D4;+0:7](-[OH;D1;+0:8])(-[c:9]1:[c:10]:[c:11]:[#16;a:12]:[c:13]:1)-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[#7;a:4]:1 | null | [] | null | null | null | null | The title compound was prepared by following the general method of Example 36 but using 3-acetylthiophene and 5-methoxymethyl-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cscn1 | c1cscn1 | c1cscn1.c1ccsc1 | null | null | null | null | CC(=O)c1ccsc1.COCc1scnc1C>>COCc1sc(C(C)(O)c2ccsc2)nc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5df902db51f4973b3595b8e30064e32 | C[Si](C)(C)N=[N+]=[N-].Cc1ncoc1C(C)(O)c1ccoc1>>Cc1ncoc1C(C)(N=[N+]=[N-])c1ccoc1 | O.O1C=C(C=C1)C(C)(O)C1=C(N=CO1)C.C[Si](C)(C)N=[N+]=[N-].B(F)(F)F>>N(=[N+]=[N-])C(C)(C1=C(N=CO1)C)C1=COC=C1 | C[Si](C)(C)[N:9]=[N+:10]=[N-:11].O[C:7]([c:6]1[c:2]([CH3:1])[n:3][cH:4][o:5]1)([CH3:8])[c:12]1[cH:13][cH:14][o:15][cH:16]1>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])([N:9]=[N+:10]=[N-:11])[c:12]1[cH:13][cH:14][o:15][cH:16]1 | C[Si](C)(C)N=[N+]=[N-].Cc1ncoc1C(C)(O)c1ccoc1 | Cc1ncoc1C(C)(N=[N+]=[N-])c1ccoc1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 0509339f927cf4d56b29cc090967b960c097a7bdff4eba5e10a42acb1ecc7a22 | af4082b86080041b9f6d702bf62e48a6b9d294ca1f4446f55ade86dd878f5885 | c1cc(Cc2cnco2)co1 | C-[Si](-C)(-C)-[N;H0;D2;+0:1]=[#7;+:2]=[N;-;D1;H0:3].O-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[c:6]1:[c:7]:[c:8]:[#8;a:9]:[c:10]:1)-[c:11]1:[#8;a:12]:[c:13]:[#7;a:14]:[c:15]:1-[C;D1;H3:16]>>[C;D1;H3:16]-[c:15]1:[#7;a:14]:[c:13]:[#8;a:12]:[c:11]:1-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[N;H0;D2;+0:1]=[#7;+:2]=[N;-;D1;H0:3])-[c:6]1:[c:7]:... | null | [] | null | null | 8 | HOUR | 1-(3-Furyl)-1-(4-methyl-5-oxazolyl)ethanol (1 g) was suspended in benzene (4 ml). Trimethylsilylazide (822 μl) was added followed by boron trifluoride diethyletherate (770 μl). The mixture was stirred overnight at room temperature, then poured into water and extracted to give the title compound.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Tertiary alcohol.Silyl protective group | Azide | null | null | c1cocn1.c1ccoc1 | HO- | C1=CC=CC=C1 | null | 8 | C[Si](C)(C)N=[N+]=[N-].Cc1ncoc1C(C)(O)c1ccoc1>C1=CC=CC=C1>Cc1ncoc1C(C)(N=[N+]=[N-])c1ccoc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dab48b2bfda241a4b7f0f62acf90e643 | Cc1ncoc1C(C)(N=[N+]=[N-])c1ccoc1>>Cc1ncoc1C(C)(N)c1ccoc1 | N(=[N+]=[N-])C(C)(C1=C(N=CO1)C)C1=COC=C1>>O1C=C(C=C1)C(C)(C1=C(N=CO1)C)N | [N-]=[N+]=[N:9][C:7]([c:6]1[c:2]([CH3:1])[n:3][cH:4][o:5]1)([CH3:8])[c:10]1[cH:11][cH:12][o:13][cH:14]1>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])([NH2:9])[c:10]1[cH:11][cH:12][o:13][cH:14]1 | Cc1ncoc1C(C)(N=[N+]=[N-])c1ccoc1 | Cc1ncoc1C(C)(N)c1ccoc1 | null | [Pd] | C(C)O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1cc(Cc2cnco2)co1 | [#7;a:1]:[c:2]:[c:3](-[C:4](-[C;D1;H3:5])(-[N;H0;D2;+0:6]=[N+]=[N-])-[c:7]:[c:8]:[#8;a:9]):[#8;a:10]>>[#7;a:1]:[c:2]:[c:3](-[C:4](-[C;D1;H3:5])(-[NH2;D1;+0:6])-[c:7]:[c:8]:[#8;a:9]):[#8;a:10] | null | [] | null | null | null | null | The product from Example 65 in ethanol was hydrogenated in the presence of 10% palladium-on-charcoal to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1cocn1.c1ccoc1 | Other | [Pd].C(C)O | null | null | Cc1ncoc1C(C)(N=[N+]=[N-])c1ccoc1>[Pd].C(C)O>Cc1ncoc1C(C)(N)c1ccoc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8bbdc1d08b854285b965d5186398def4 | COc1ccc(CCN)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>COc1ccc(CCN=C=O)cc1 | COC1=CC=C(C=C1)CCN.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>COC1=CC=C(C=C1)CCN=C=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[cH:12][cH:13]1.ClC(Cl)(Cl)O[C:10](OC(Cl)(Cl)Cl)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]=[C:10]=[O:11])[cH:12][cH:13]1 | COc1ccc(CCN)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | COc1ccc(CCN=C=O)cc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 38334b31448e1d8428e2cb6569eceaecc2305b2359c734a98433aa0746ff9140 | a539b8d5e65abe163774733461d6850ba8234d38df1df3c2ccdeef5ce9de389b | c1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[N;H0;D2;+0:5]=[C;H0;D2;+0:1]=[O;D1;H0:2] | 0.1 | [{"value": 0.1, "product": "COC1=CC=C(C=C1)CCN=C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.53 g (30 mol) of 4-methoxy-β-phenylethylamine are added dropwise to a solution of 2.96 g (10.0 mol) of triphosgene in 30 ml of dry tetrahydrofuran and the mixture is heated at the boiling point for 2 hours. The solution is cooled to room temperature and filtered and the filtrate is concentrated in vacuo. The colorles... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine | Isocyanate | null | null | c1ccccc1 | HCl | O1CCCC1 | null | null | COc1ccc(CCN)cc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O1CCCC1>COc1ccc(CCN=C=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ee33145d3712452584d543409e62c64a | C[Si](C)(C)OCCNCCO[Si](C)(C)C.O=S(=O)(Cl)c1ccccc1>>C[Si](C)(C)OCCN(CCO[Si](C)(C)C)S(=O)(=O)c1ccccc1 | C[Si](C)(C)OCCNCCO[Si](C)(C)C.C(C)N(CC)CC.C1(=CC=CC=C1)S(=O)(=O)Cl>>C[Si](OCCN(S(=O)(=O)C1=CC=CC=C1)CCO[Si](C)(C)C)(C)C | [CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[CH3:15].Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[S:16](=[O:17])(=[O:18]... | C[Si](C)(C)OCCNCCO[Si](C)(C)C.O=S(=O)(Cl)c1ccccc1 | C[Si](C)(C)OCCN(CCO[Si](C)(C)C)S(=O)(=O)c1ccccc1 | null | null | C1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 88 | [{"value": 88.0, "product": "C[Si](OCCN(S(=O)(=O)C1=CC=CC=C1)CCO[Si](C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 4.97 g of bis(2-trimethylsilyloxylethyl)amine, 3.03 g of triethylamine and 50 ml of benzene, 3.21 g of benzenesulfonyl chloride was added at 0° C. under stirring. After the addition, the mixture was taken out of the cooling bath and stirred further for 2 hours. The reaction mixture was filtered, mixture... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1 | HCl | C1=CC=CC=C1 | null | null | C[Si](C)(C)OCCNCCO[Si](C)(C)C.O=S(=O)(Cl)c1ccccc1>C1=CC=CC=C1>C[Si](C)(C)OCCN(CCO[Si](C)(C)C)S(=O)(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39d007a1ceb040768775ffb5002a1d9e | CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)[c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)c(S(=O)(=O)... | [Si](C)(C)(C(C)(C)C)OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(... | CC(C)(C)[Si](C)(C)[O:19][CH2:18][CH2:17][N:16]([S:13]([c:12]1[cH:11][cH:10][c:9]([Bi:8]([c:7]2[cH:6][cH:5][c:4]([S:2](=[O:1])(=[O:3])[N:73]([CH2:74][CH2:75][O:76][Si](C)(C)C(C)(C)C)[CH2:77][CH2:78][O:79][Si](C)(C)C(C)(C)C)[cH:72][c:61]2[S:62](=[O:63])(=[O:64])[N:65]([CH2:66][CH2:67][O:68][Si](C)(C)C(C)(C)C)[CH2:69][CH2... | CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)[c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)c(S(=O)(=O)... | O=S(=O)(c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO)CCO)cc2S(=O)(=O)N(CCO)CCO)[c]2ccc(S(=O)(=O)N(CCO)CCO)cc2S(=O)(=O)N(CCO)CCO)c(S(=O)(=O)N(CCO)CCO)c1)N(CCO)CCO | null | null | ClCCl | Acylation | OtherReaction | 359bed4e3c72098746a78db3da27cb1c0b97b319d671d22f5a85b7ad088942cb | 599c6070da98d6760709ea4de50e837637a1694af54ce586f2fc58936c993de1 | c1cc[c]([Bi]([c]2ccccc2)[c]2ccccc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:4]-[C:5]-[C:6].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:7]-[C:8]-[C:9].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:10]-[C:11]-[C:12].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:13]-[C:14]-[C:15].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:16]-[C:17]-[C:18]... | 79.5 | [{"value": 79.5, "product": "OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO)CCO)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 13.59 g of the tris(2,4-bis(N,N-bis(2-t-butyldimethylsilyloxyethyl)sulfamoyl)phenyl)bismuthine preparation prepared in Example 5 was dissolved in a mixed solvent containing 13.6 ml of ethanol and 27 ml of dichloromethane, and 0.272 g of p-toluenesulfonic acid monohydrate was added thereto. The mixture was refluxed unde... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether prot... | Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | TsOH.HO- | ClCCl | 50 | null | CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)[c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)c(S(=O)(=O)... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3672ccce920d49079a5e6ae5ceeb8bc3 | CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)[c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)c(S(=O)(=O)... | [Si](C)(C)(C(C)(C)C)OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(... | CC(C)(C)[Si](C)(C)[O:19][CH2:18][CH2:17][N:16]([S:13]([c:12]1[cH:11][cH:10][c:9]([Bi:8]([c:7]2[cH:6][cH:5][c:4]([S:2](=[O:1])(=[O:3])[N:73]([CH2:74][CH2:75][O:76][Si](C)(C)C(C)(C)C)[CH2:77]C[O:71][Si](C)(C)C(C)(C)C)[cH:72][c:61]2[S:62](=[O:63])(=[O:64])[N:65]([CH2:66][CH2:78][O:79][Si](C)(C)C(C)(C)C)[CH2:69][CH2:70][O:... | CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)[c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)c(S(=O)(=O)... | O=S(=O)(c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO)CCO)cc2S(=O)(=O)N(CCO)CCO)[c]2ccc(S(=O)(=O)N(CCO)CCO)cc2S(=O)(=O)N(CCO)CCO)c(S(=O)(=O)N(CCO)CCO)c1)N(CCO)CCO | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 27071b625f155943525e8e1dca0bcfaee51b4f12629eef0a240fd7b9410de62b | 8da181d42bd002294543811ee0c10c300809942818f884161cd413d2680745af | c1cc[c]([Bi]([c]2ccccc2)[c]2ccccc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-C-[CH2;D2;+0:2]-[#7:3](-[#16:4])-[C:5]-[C:6]-[O;H0;D2;+0:7]-[Si](-C)(-C)-C(-C)(-C)-C.C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[C:10]-[#7:11](-[#16:12])-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[O;H0;D2;+0:15]-[Si](-C)(-C)-C(-C)(-C)-C.C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:16]-[C:... | 94.7 | [{"value": 94.7, "product": "OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO)CCO)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | null | null | A solution of 1.38 g of the tris(2,4-bis(N,N-bis(2-t-butyldimethylsilyloxyethyl)sulfamoyl)phenyl)bismuthine preparation obtained in Example 5 in 15 ml of tetrahydrofuran was cooled to -30° C., and 5.88 ml of a 1 M/1 tetrahydrofuran solution of tetra-n-butylammonium fluoride was gradually added droprise under stirring. ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective gr... | Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | -30 | null | CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1cc[c]([Bi]([c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)[c]2ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)cc2S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)c(S(=O)(=O)... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-51c44092234a4bbebe6940b7ac132c46 | CCNCC.CCOC(=O)CC(C)=O>>CCN(CC)C(=O)CC(C)=O | C(CC(=O)C)(=O)OCC.C(C)NCC>>C(C)N(C(CC(C)=O)=O)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].CCO[C:6](=[O:7])[CH2:8][C:9]([CH3:10])=[O:11]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[CH2:8][C:9]([CH3:10])=[O:11] | CCNCC.CCOC(=O)CC(C)=O | CCN(CC)C(=O)CC(C)=O | null | null | null | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C;D1;H3:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C;D1;H3:11]>>[C;D1;H3:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9](-[C:8]-[C;D1;H3:7])-[C:10]-[C;D1;H3:11] | 65.7 | [{"value": 65.7, "product": "C(C)N(C(CC(C)=O)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 40 g (0.31 mol) of ethyl acetoacetate and 24 g (0.33 mol) of diethylamine were stirred in a Parr apparatus at 150° C. for 10'. The crude mixture was distilled at 115°-120° C./9 mmHg, to give 32 g of the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: The crude mixture was distilled at 115°-120... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | null | HO- | null | null | null | CCNCC.CCOC(=O)CC(C)=O>>CCN(CC)C(=O)CC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70526c16165b456992991e767fe845d3 | CCN(CC)C(=O)CC(C)=O.N#[N+]c1ccccc1>>CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O | [Cl-].C1(=CC=CC=C1)[N+]#N.C(C)N(C(CC(C)=O)=O)CC.CC(=O)O[Na].O>>C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[CH2:8][C:17]([CH3:18])=[O:19].[N:9]#[N+:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[C:8](=[N:9][NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17]([CH3:18])=[O:19] | CCN(CC)C(=O)CC(C)=O.N#[N+]c1ccccc1 | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O | null | null | C(C)O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | c1ccccc1 | [C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[N;H0;D1;+0:10]#[N+;H0;D2:11]-[c:12](:[c:13]):[c:14]>>[C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[N;H0;D2;+0:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | null | [] | 10 | CELSIUS | null | null | 15.7 g (0.1 mol) of N,N-diethyl-3-oxobutyramide were mixed with 12 g (0.14 mol) of CH3COONa, 20 ml of water and 75 ml of ethanol. The solution obtained was cooled to 10° C. and 0.1 mol of freshly prepared solution of phenyldiazonium chloride [Organic Reactions, R. Adams Ed; Wiley, New York, 10, 32-33, (1951-1959)] were... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1 | null | C(C)O | 10 | null | CCN(CC)C(=O)CC(C)=O.N#[N+]c1ccccc1>C(C)O>CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9d861ba9b54b4ef8a7a1d9b237766965 | CCCNCCC.CCOC(=O)CC(C)=O>>CCCN(CCC)C(=O)CC(C)=O | C(CC(=O)C)(=O)OCC.C(CC)NCCC>>C(CC)N(C(CC(C)=O)=O)CCC | [CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH3:7].CCO[C:8](=[O:9])[CH2:10][C:11]([CH3:12])=[O:13]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[CH2:10][C:11]([CH3:12])=[O:13] | CCCNCCC.CCOC(=O)CC(C)=O | CCCN(CCC)C(=O)CC(C)=O | null | null | null | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6] | 0.6 | [{"value": 0.6, "product": "C(CC)N(C(CC(C)=O)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 43.4 g (43.3 mol) of ethyl acetoacetate and 33.7 g (43.3 mol) of dipropylamine were treated as described in preparation 1. The crude oil was distilled at 86°-89° C./ 0.8 mmHg, to give 44.3 g of the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: as described in preparation 1; The crude oil was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | null | HO- | null | null | null | CCCNCCC.CCOC(=O)CC(C)=O>>CCCN(CCC)C(=O)CC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-549c90cb2eaf4302a24586469500c664 | CCCN(CCC)C(=O)CC(C)=O.N#[N+]c1ccccc1>>CCCN(CCC)C(=O)C(=NNc1ccccc1)C(C)=O | C(CC)N(C(CC(C)=O)=O)CCC.CC(=O)O[Na].O.[Cl-].C1(=CC=CC=C1)[N+]#N>>C(CC)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CCC | [CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[CH2:10][C:19]([CH3:20])=[O:21].[N:11]#[N+:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[C:10](=[N:11][NH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19]([CH3:20])=[O:21] | CCCN(CCC)C(=O)CC(C)=O.N#[N+]c1ccccc1 | CCCN(CCC)C(=O)C(=NNc1ccccc1)C(C)=O | null | null | C(C)O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | c1ccccc1 | [C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[N;H0;D1;+0:10]#[N+;H0;D2:11]-[c:12](:[c:13]):[c:14]>>[C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[N;H0;D2;+0:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 14.5 | [{"value": 14.5, "product": "C(CC)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 18.5 g (0.1 mol) of N,N-dipropyl-3-oxobutyramide, 12 g (0.146 mol) of CH3COONa, 20 ml of water, 75 ml of ethanol and a solution of 0.1 mol of phenyldiazonium chloride were treated as described in preparation 2. The precipitated solid was filtered and dried in vacuo yielding 4.2 g of the title compound. M.p.=79°-80° C.
... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1 | null | C(C)O | null | null | CCCN(CCC)C(=O)CC(C)=O.N#[N+]c1ccccc1>C(C)O>CCCN(CCC)C(=O)C(=NNc1ccccc1)C(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78feaec48f454c398ecf0ddf11da5e02 | CC(C)CO.CCOC(=O)CC(C)=O>>CC(=O)CC(=O)OCC(C)C | C(CC(=O)C)(=O)OCC.C(C(C)C)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(CC(=O)C)(=O)OCC(C)C | [OH:7][CH2:8][CH:9]([CH3:10])[CH3:11].CCO[C:5]([CH2:4][C:2]([CH3:1])=[O:3])=[O:6]>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[O:7][CH2:8][CH:9]([CH3:10])[CH3:11] | CC(C)CO.CCOC(=O)CC(C)=O | CC(=O)CC(=O)OCC(C)C | null | null | null | Acylation | Transesterification | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6] | null | [] | null | null | null | null | 30 ml of ethyl acetoacetate were dissolved in 350 ml of i-butyl alcohol and a catalytic amount of p-toluensulphonic acid (PTSA) was added. The solution was refluxed for 18 h. The reaction mixture was evaporated in vacuo and the residue was dissolved in ether. The resulted solution was treated with s.s. NaHCO3. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | null | HO- | null | null | null | CC(C)CO.CCOC(=O)CC(C)=O>>CC(=O)CC(=O)OCC(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb91f88045c44fa2ba05b793165e13a8 | CC(=O)CC(=O)OCC(C)C.N#[N+]c1ccccc1>>CC(=O)C(=NNc1ccccc1)C(=O)OCC(C)C | C(CC(=O)C)(=O)OCC(C)C.O.[Cl-].C1(=CC=CC=C1)[N+]#N>>C1(=CC=CC=C1)NN=C(C(=O)OCC(C)C)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:13](=[O:14])[O:15][CH2:16][CH:17]([CH3:18])[CH3:19].[N:5]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[C:4](=[N:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[O:15][CH2:16][CH:17]([CH3:18])[CH3:19] | CC(=O)CC(=O)OCC(C)C.N#[N+]c1ccccc1 | CC(=O)C(=NNc1ccccc1)C(=O)OCC(C)C | null | null | C(C)O | Functional Group Addition | OtherReaction | ac990c1d08488fa2e65d155d0c3fe4275090c987d9bb341129ddd972268410d2 | b6b5844d1b47f1f414d9a8547509e4caf3076e8d8ccfaed07a6c1e5bfa92686d | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8].[N;H0;D1;+0:9]#[N+;H0;D2:10]-[c:11](:[c:12]):[c:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[N;H0;D2;+0:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:6](-[C;D1;H3:7])=[O;D1;H0:8] | 88.1 | [{"value": 88.1, "product": "C1(=CC=CC=C1)NN=C(C(=O)OCC(C)C)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 15.8 g (0.1 mol) of i-butyl acetoacetate, 12 g (0.146 mol) of CH3 COONa, 20 ml of water, 75 ml of ethanol and a solution of 0.1 mol of phenyldiazonium chloride were treated as described in preparation 2. The precipitated solid was filtered an dried in vacuo yielding 23.1 g of the title compound. M.p.=45°-50° C.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Hydrazone | null | null | c1ccccc1 | null | C(C)O | null | null | CC(=O)CC(=O)OCC(C)C.N#[N+]c1ccccc1>C(C)O>CC(=O)C(=NNc1ccccc1)C(=O)OCC(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f260c158922847e2b6dce05f84aaf68d | CC1=CC(=O)OC(C)(C)O1.NCc1ccccc1>>CC(=O)CC(=O)NCc1ccccc1 | CC1(OC(=CC(O1)=O)C)C.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC(CC(C)=O)=O | CC1(C)O[C:5](=[O:6])[CH:4]=[C:2]([CH3:1])[O:3]1.[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | CC1=CC(=O)OC(C)(C)O1.NCc1ccccc1 | CC(=O)CC(=O)NCc1ccccc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | d3497dc1fa1b901da02291a01ed87bb0f2a9e66617453ae54be3d88b09104f0d | 60464cf75aa3f9019baecc3c3022956a9a8a68b3326c8dcc2d0679ff3c32da26 | c1ccccc1 | C-C1(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C;D1;H3:5])-[O;H0;D2;+0:6]-1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[C;D1;H3:5]-[C;H0;D3;+0:4](=[O;H0;D1;+0:6])-[CH2;D2;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:8]-[c:9] | null | [] | null | null | null | null | 9 ml (0.05 mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (diketene-acetone adduct) were added dropwise to a solution of 5.5 ml (0.05 mol) of benzylamine in 20 ml of toluene and the temperature was allowed to rise 70° C. The solution was refluxed for 2 h then the solvent was removed in vacuo. The crude product was tritura... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine | Ketone.Secondary amide | C1=COCOC1 | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC1=CC(=O)OC(C)(C)O1.NCc1ccccc1>C1(=CC=CC=C1)C>CC(=O)CC(=O)NCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-24aef19954464872a4172777d7b361e8 | CC(=O)CC(=O)NCc1ccccc1.N#[N+]c1ccccc1>>CC(=O)C(=NNc1ccccc1)C(=O)NCc1ccccc1 | [Cl-].C1(=CC=CC=C1)[N+]#N.C(C1=CC=CC=C1)NC(CC(C)=O)=O.[OH-].[Na+]>>C(C1=CC=CC=C1)NC(C(C(C)=O)=NNC1=CC=CC=C1)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:13](=[O:14])[NH:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[N:5]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[C:4](=[N:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[NH:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)CC(=O)NCc1ccccc1.N#[N+]c1ccccc1 | CC(=O)C(=NNc1ccccc1)C(=O)NCc1ccccc1 | null | null | O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | O=C(C=NNc1ccccc1)NCc1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8].[N;H0;D1;+0:9]#[N+;H0;D2:10]-[c:11](:[c:12]):[c:13]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[N;H0;D2;+0:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:6](-[C;D1;H3:7])=[O;D1;H0:8] | null | [] | null | null | null | null | 7.27 g (0.038) of N-benzyl-3-oxobutyramide were dissolved in a solution of 5.32 g (0.133 mol) of NaOH in 58 ml of water. To the ice-cooled stirred solution, 0.040 mol of phenyldiazonium chloride were added dropwise at such a rate as to keep the temperature at 0° C. The precipitated solid was filtered and recrystallised... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1.c1ccccc1 | null | O | null | null | CC(=O)CC(=O)NCc1ccccc1.N#[N+]c1ccccc1>O>CC(=O)C(=NNc1ccccc1)C(=O)NCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fc50405695d1443a80eda06a3dd99d45 | C1CCNC1.C=C1CC(=O)O1>>CC(=O)CC(=O)N1CCCC1 | C=C1CC(=O)O1.CC(=O)C.N1CCCC1>>O=C(CC(=O)N1CCCC1)C | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.[CH2:1]=[C:2]1[O:3][C:5](=[O:6])[CH2:4]1>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1 | C1CCNC1.C=C1CC(=O)O1 | CC(=O)CC(=O)N1CCCC1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 1993eb37d80a920c8fe458a795d74455bf51017aa874ab2592fe04454f920492 | 9efa0c835be0aa9453aa895a9d5c6a73c10e08e695158204e8f0348795b4fe67 | C1CCNC1 | [CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.[C:7]1-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:6])-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:11]-[C:10]-1 | 97.9 | [{"value": 97.9, "product": "O=C(CC(=O)N1CCCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 9 ml (0.05 mol) of diketene-acetone adduct and a solution of 4.2 ml (0.05 mol) of pyrrolidine in 20 ml of toluene were treated as described in preparation 7. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→1%) yielding 7.6 g of the title compound as a dark oi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Vinyl | Ketone.Tertiary amide | C1CCNC1.C1COC1 | C1CC[NH]C1 | C1CC[NH]C1 | null | C1(=CC=CC=C1)C | null | null | C1CCNC1.C=C1CC(=O)O1>C1(=CC=CC=C1)C>CC(=O)CC(=O)N1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f388a24479e44c98bc290884466e1ad3 | CC(=O)CC(=O)Nc1ccccc1.N#[N+]c1ccccc1>>CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1 | C(CC(=O)C)(=O)NC1=CC=CC=C1.[OH-].[Na+].[Cl-].C1(=CC=CC=C1)[N+]#N>>C1(=CC=CC=C1)NC(C(C(C)=O)=NNC1=CC=CC=C1)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:13](=[O:14])[NH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[N:5]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[C:4](=[N:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[NH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CC(=O)CC(=O)Nc1ccccc1.N#[N+]c1ccccc1 | CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1 | null | null | O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | O=C(C=NNc1ccccc1)Nc1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8].[N;H0;D1;+0:9]#[N+;H0;D2:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[C;H0;D3;+0:4](=[N;H0;D2;+0:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8] | 47.6 | [{"value": 47.6, "product": "C1(=CC=CC=C1)NC(C(C(C)=O)=NNC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.5 g (25.4 mmol) of acetoacetanilide, a solution of 3.46 g (89 mmol) of NaOH in 45 ml of water and 95 mmol of phenyldiazonium chloride were treated as described in preparation 8. The residue was crystallised from EtOH, yielding 3.4 g of the title compound. M.p.=96°-97° C.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1.c1ccccc1 | null | O | null | null | CC(=O)CC(=O)Nc1ccccc1.N#[N+]c1ccccc1>O>CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb592b1203c74e969732293b7513ee02 | C=C1CC(=O)O1.CNC>>CC(=O)CC(=O)N(C)C | C=C1CC(=O)O1.CC(=O)C.CNC>>CN(C(CC(C)=O)=O)C | [CH2:1]=[C:2]1[O:3][C:5](=[O:6])[CH2:4]1.[NH:7]([CH3:8])[CH3:9]>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[N:7]([CH3:8])[CH3:9] | C=C1CC(=O)O1.CNC | CC(=O)CC(=O)N(C)C | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 064f44e0040954705f8be5256a3aced414ff315ce6eb541c993cd172d38561e4 | 9efa0c835be0aa9453aa895a9d5c6a73c10e08e695158204e8f0348795b4fe67 | null | [C;D1;H3:1]-[NH;D2;+0:2]-[C;D1;H3:3].[CH2;D1;+0:4]=[C;H0;D3;+0:5]1-[C:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:6]-[C;H0;D3;+0:5](-[CH3;D1;+0:4])=[O;H0;D1;+0:9] | null | [] | null | null | null | null | A solution of 9 ml (0.05 mmol) of diketene-acetone adduct in 20 ml of toluene was treated with gaseous dimethylamine at room temperature until the reaction was complete. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→10%) yielding 7.0 g of the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Vinyl | Ketone.Tertiary amide | C1COC1 | null | null | null | C1(=CC=CC=C1)C | null | null | C=C1CC(=O)O1.CNC>C1(=CC=CC=C1)C>CC(=O)CC(=O)N(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b070703fd73b4d8680fe6f71c91c67d7 | CC(=O)CC(=O)N(C)C.N#[N+]c1ccccc1>>CC(=O)C(=NNc1ccccc1)C(=O)N(C)C | CN(C(CC(C)=O)=O)C.[OH-].[Na+].[Cl-].C1(=CC=CC=C1)[N+]#N>>CN(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C | [CH3:1][C:2](=[O:3])[CH2:4][C:13](=[O:14])[N:15]([CH3:16])[CH3:17].[N:5]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[C:4](=[N:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[N:15]([CH3:16])[CH3:17] | CC(=O)CC(=O)N(C)C.N#[N+]c1ccccc1 | CC(=O)C(=NNc1ccccc1)C(=O)N(C)C | null | null | O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | c1ccccc1 | [C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[N;H0;D1;+0:10]#[N+;H0;D2:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[N;H0;D2;+0:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 42.9 | [{"value": 42.9, "product": "CN(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.5 g (0.035 mol) of N,N-dimethyl-3-oxobutyramide, a solution of 4.9 g (0.122 mol) of NaOH in 45 ml of water and 0.037 mol of phenyldiazonium chloride were treated as described in preparation 8. The crude reaction mixture was purified by chromatography on silica gel (hexane/Et2O 0%→100%) obtaining 3.5 g of the title co... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1 | null | O | null | null | CC(=O)CC(=O)N(C)C.N#[N+]c1ccccc1>O>CC(=O)C(=NNc1ccccc1)C(=O)N(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa496a7ce126439c8a04c703ffcedc08 | CC(=O)CC(N)=O.N#[N+]c1ccccc1>>CC(=O)C(=NNc1ccccc1)C(N)=O | O=C(CC(=O)N)C.[OH-].[Na+].[Cl-].C1(=CC=CC=C1)[N+]#N>>C1(=CC=CC=C1)NN=C(C(=O)N)C(C)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:13]([NH2:14])=[O:15].[N:5]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[C:4](=[N:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]([NH2:14])=[O:15] | CC(=O)CC(N)=O.N#[N+]c1ccccc1 | CC(=O)C(=NNc1ccccc1)C(N)=O | null | null | O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | c1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C:5](-[N;D1;H2:6])=[O;D1;H0:7].[N;H0;D1;+0:8]#[N+;H0;D2:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[C;H0;D3;+0:4](=[N;H0;D2;+0:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:5](-[N;D1;H2:6])=[O;D1;H0:7] | null | [] | null | null | null | null | 5.0 g (0.049 mol) of 3-oxobutyramide, a solution of 6.9 g (0.171 mol) of NaOH in 75 ml of water and 0.051 mol of phenyldiazonium chloride were treated as described in preparation 8. The crude reaction mixture was purified by chromatography on silica gel(EtOAc) obtaining 3 g of the title compound which was used as such ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1 | null | O | null | null | CC(=O)CC(N)=O.N#[N+]c1ccccc1>O>CC(=O)C(=NNc1ccccc1)C(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ee71b009ed3f4c28bab5abd1c42abd9d | CC(=O)CC(=O)N(C(C)C)C(C)C.N#[N+]c1ccccc1>>CC(=O)C(=NNc1ccccc1)C(=O)N(C(C)C)C(C)C | C(C)(C)N(C(CC(C)=O)=O)C(C)C.[OH-].[Na+].[Cl-].C1(=CC=CC=C1)[N+]#N>>C(C)(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C(C)C | [CH3:1][C:2](=[O:3])[CH2:4][C:13](=[O:14])[N:15]([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21].[N:5]#[N+:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[C:4](=[N:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[N:15]([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21] | CC(=O)CC(=O)N(C(C)C)C(C)C.N#[N+]c1ccccc1 | CC(=O)C(=NNc1ccccc1)C(=O)N(C(C)C)C(C)C | null | null | O | Functional Group Addition | OtherReaction | 7ec843ece642d406b254050374a9acdeded6ee16c74f2d78979f305a41c35216 | ea063a30965cc9c0238244fbd3133685f07e51f73fbeaf7c962038081c44c705 | c1ccccc1 | [C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[N;H0;D1;+0:10]#[N+;H0;D2:11]-[c:12](:[c:13]):[c:14]>>[C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[N;H0;D2;+0:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 68.2 | [{"value": 68.2, "product": "C(C)(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7.0 g (0.038 mol) of N,N-diisopropyl-3-oxobutyramide, a solution of 5.3 g (0.133 mol) of NaOH in 58 ml of water and 0.04 mol of phenyldiazonium chloride were treated as described in preparation 8. The crude reaction mixture was purified by chromatography on silica gel (hexane/Et2O 95:5) obtaining 7.5 g of the title com... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Hydrazone | null | null | c1ccccc1 | null | O | null | null | CC(=O)CC(=O)N(C(C)C)C(C)C.N#[N+]c1ccccc1>O>CC(=O)C(=NNc1ccccc1)C(=O)N(C(C)C)C(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5378909b6f194efbaaaae9d5077f9d43 | CCOC(=O)CC(=O)C(F)(F)F.N#[N+]c1ccccc1>>CCOC(=O)C(=NNc1ccccc1)C(=O)C(F)(F)F | CCOC(=O)CC(=O)C(F)(F)F.CC(=O)O[Na].O.[Cl-].C1(=CC=CC=C1)[N+]#N>>C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C(F)(F)F)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:15](=[O:16])[C:17]([F:18])([F:19])[F:20].[N:7]#[N+:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[N:7][NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[C:17]([F:18])([F:19])[F:20] | CCOC(=O)CC(=O)C(F)(F)F.N#[N+]c1ccccc1 | CCOC(=O)C(=NNc1ccccc1)C(=O)C(F)(F)F | null | null | C(C)O | Functional Group Addition | OtherReaction | ac990c1d08488fa2e65d155d0c3fe4275090c987d9bb341129ddd972268410d2 | b6b5844d1b47f1f414d9a8547509e4caf3076e8d8ccfaed07a6c1e5bfa92686d | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[N;H0;D1;+0:12]#[N+;H0;D2:13]-[c:14](:[c:15]):[c:16]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[N;H0;D2;+0:12]-[NH;D2;+0:13]-[c:14](:[c:15]):[c:16])-[C:6](=[O;D1;H0:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H... | 60 | [{"value": 60.0, "product": "C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7.3 ml (0.05 mol) of ethyl 3-oxo-4,4,4-trifluoroacetoacetate, 6 g (0.073 mol) of CH3COONa, 20 ml of water, 37.5 ml of ethanol and a solution of 0.05 mol of phenyldiazonium chloride were treated as described in preparation 2. The crude product was purified by chromatography on silica gel (hexane/Et2O 0%→25%) obtaining 8... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Hydrazone | null | null | c1ccccc1 | null | C(C)O | null | null | CCOC(=O)CC(=O)C(F)(F)F.N#[N+]c1ccccc1>C(C)O>CCOC(=O)C(=NNc1ccccc1)C(=O)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-65c40f72159b46c38bd188c224445f20 | C=COC(=O)Cl.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>>COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1.Cl | C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C.C(=C)OC(=O)Cl>>Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O | C=COC(=O)[Cl:20].CC[N:11]1[CH2:10][CH2:9][C@@:8]2([c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19]3)[C@H:13]([CH2:12]1)[CH2:14][CH2:15][C:16](=[O:17])[CH2:18]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C@:8]23[CH2:9][CH2:10][NH:11][CH2:12][C@@H:13]2[CH2:14][CH2:15][C:16](=[O:17])[CH2:18]3)[cH:19]1.[ClH:20] | C=COC(=O)Cl.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1.Cl | null | null | ClCCCl | Miscellaneous | OtherReaction | 3772a9f4b4332669564daf911df24c9f8519db39dd2cee234af6094fd48a7fbc | 0cd324a7b0205d651c1ead3697762ad8fc9df01bb471480a7b4de674230fb053 | O=C1CC[C@H]2CNCC[C@]2(c2ccccc2)C1 | C-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].C=C-O-C(=O)-[Cl;H0;D1;+0:6]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3].[ClH;D0;+0:6] | 70.8 | [{"value": 70.8, "product": "Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1.2 g (4.2 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline and 1.8 g (12.6 mmol) of proton sponge in 34 ml of 1,2-dichloroethane was treated with 1.4 ml (16.8 mmol) of vinylchloroformate at 0° C. under nitrogen atmosphere. The reaction mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Tertiary amine.Vinyl | Secondary amine | C1CC[C@H]2C[NH]CC[C@@H]2C1 | C1CC[C@H]2CNCC[C@H]2C1 | c1ccccc1.C1CC[C@H]2CNCC[C@H]2C1 | HO- | ClCCCl | null | 0.25 | C=COC(=O)Cl.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>ClCCCl>COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d8b6f19e1cf843a08f290872c0b51286 | BrCC1CC1.COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1>>COc1cccc([C@]23CCN(CC4CC4)C[C@@H]2CCC(=O)C3)c1 | Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O.C1(CC1)CBr.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>Cl.C1(CC1)CN1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O | Br[CH2:12][CH:13]1[CH2:14][CH2:15]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C@:8]23[CH2:9][CH2:10][NH:11][CH2:16][C@@H:17]2[CH2:18][CH2:19][C:20](=[O:21])[CH2:22]3)[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C@:8]23[CH2:9][CH2:10][N:11]([CH2:12][CH:13]4[CH2:14][CH2:15]4)[CH2:16][C@@H:17]2[CH2:18][CH2:19][C:... | BrCC1CC1.COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1 | COc1cccc([C@]23CCN(CC4CC4)C[C@@H]2CCC(=O)C3)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6e833cca23f118c68a36bbb41859e9d07893cc24605eee90454f4e286f04398 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CC[C@H]2CN(CC3CC3)CC[C@]2(c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1)-[C:8]-[C:9] | 26 | [{"value": 26.0, "product": "Cl.C1(CC1)CN1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.88 g (3.08 mmol) of (±)-trans-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.44 g (3,23 mmol) of cyclopropylmethyl bromide, 0.64 g of potassium carbonate and a catalytical amount of potassium iodide in 15.4 ml of DMF were stirred at 60° C. for 2 h. The solvent was removed in v... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CC[C@H]2CNCC[C@H]2C1 | C1CC[C@H]2C[NH]CC[C@H]2C1 | c1ccccc1.C1CC1.C1CC[C@H]2C[NH]CC[C@H]2C1 | HBr | CN(C)C=O | null | null | BrCC1CC1.COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1>CN(C)C=O>COc1cccc([C@]23CCN(CC4CC4)C[C@@H]2CCC(=O)C3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cef4a5077a74084b0f66091336f0c5e | CCCCBr.COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1>>CCCCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O.C(CCC)Br.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>C(CCC)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O | Br[CH2:4][CH2:3][CH2:2][CH3:1].[NH:5]1[CH2:6][CH2:7][C@:8]2([c:9]3[cH:10][cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16]3)[CH2:17][C:18](=[O:19])[CH2:20][CH2:21][C@H:22]2[CH2:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C@:8]2([c:9]3[cH:10][cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16]3)[CH2:17][C:18](=[O:19])[CH2:2... | CCCCBr.COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1 | CCCCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 62ec5e6cc7d6988505f056dcfa4f57f44a5c16cd7a5130d4ceb03a3c06191c3a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CC[C@H]2CNCC[C@]2(c2ccccc2)C1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 24.9 | [{"value": 24.9, "product": "C(CCC)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.71 g (2.55 mmol) of (±)-trans-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline hydrochloride, 0.37 g (2.68 mmol) of butyl bromide, 0.53 g of potassium carbonate and a catalytical amount of potassium iodide in 15 ml of DMF were reacted as described in preparation 20, yielding 0.2 g of the title ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CC[C@H]2CNCC[C@@H]2C1 | C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | HBr | CN(C)C=O | null | null | CCCCBr.COc1cccc([C@]23CCNC[C@@H]2CCC(=O)C3)c1>CN(C)C=O>CCCCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4eac917dd565431a9f46b59b364b582d | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.NO>>CCN1CC[C@]2(c3cccc(OC)c3)CC(=NO)CC[C@H]2C1 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.Cl.NO>>C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=NO | O=[C:16]1[CH2:15][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]3)[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:22][C@@H:21]2[CH2:20][CH2:19]1.[NH2:17][OH:18]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]3)[CH2:15][C:16](=[N:17][OH:18])[CH2:19][CH2:20][C@H:2... | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.NO | CCN1CC[C@]2(c3cccc(OC)c3)CC(=NO)CC[C@H]2C1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 3fc1f10cfb677761aaa276368e7c40afd0a88b5ed184b5f398dacd07530a3fa9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C1CC[C@H]2CNCC[C@]2(c2ccccc2)C1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[C:5]-[C:4]-[C;H0;D3;+0:1](=[N;H0;D2;+0:6]-[O;D1;H1:7])-[C:2]-[C:3] | 96.6 | [{"value": 96.6, "product": "C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.5 g (1.54 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.456 g (6.56 mmol) of hydroxylamine hydrochloride and 0.64 g of KHCO3 in 10 ml of MeOH were refluxed for 45 min. The precipitate was filtered, the solvent was removed in vacuo and the residue ta... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | C1CC[C@H]2C[NH]CC[C@@H]2C1 | C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | HO- | CO | null | null | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.NO>CO>CCN1CC[C@]2(c3cccc(OC)c3)CC(=NO)CC[C@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ceee2b4669514a49ad828e34aae4470f | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.CCOC(=O)C(=NNc1ccccc1)C(C)=O>>CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C)=O.CC(=O)O[Na]>>C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)OCC | O=[C:8]1[CH2:9][CH2:12][C@H:13]2[CH2:14][N:15]([CH2:16][CH3:17])[CH2:18][CH2:19][C@:20]2([c:21]2[cH:22][cH:23][cH:24][c:25]([O:26][CH3:27])[cH:28]2)[CH2:29]1.O=[C:10]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[N:7]Nc1ccccc1)[CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[c:9]([c:10]1[CH3:11])[CH2:12][C@@H:13... | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.CCOC(=O)C(=NNc1ccccc1)C(C)=O | CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 3be4aad3c4d371a76ae664baccdc8bb6992e32dbd7ed2871d79c38fbfe0b2616 | c182a26a1e4916f0df3a6716875f414b9379b6dc7bc3991b1a368fed15ba5da9 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[N;H0;D2;+0:4]-N-c1:c:c:c:c:c:1)-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].O=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c;H0;D3;+0:9]2:[c;H0;D3;+0:14](:[c;H0;D3;+0:1]:1-[C;D1;H3:2])-[C:13]-[C:12]-[C:1... | 61.3 | [{"value": 61.3, "product": "C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.8 g (2.47 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride and 0.87 g (93.7 mmol) of ethyl 2-phenylhydrazono-3-oxobutyrate [Organic Reactions, R. Adams Ed; Wiley, New York, 10, 32-33, (1951-1959)] were dissolved in a mixture of 3 mi of glacial acetic acid... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone.Ester | Ester | C1CC[C@H]2C[NH]CC[C@@H]2C1.c1ccccc1 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.c1ccccc1 | HO- | [Zn].C(C)(=O)O | null | null | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.CCOC(=O)C(=NNc1ccccc1)C(C)=O>[Zn].C(C)(=O)O>CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3f82d7c91db94bdba2a3ad864f8f9a22 | CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2>>CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(O)c1)C2 | C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)OCC.B(Br)(Br)Br>>C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)OCC | C[O:26][c:25]1[cH:24][cH:23][cH:22][c:21]([C@@:20]23[C@H:13]([CH2:12][c:9]4[c:8]([nH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:10]4[CH3:11])[CH2:28]2)[CH2:14][N:15]([CH2:16][CH3:17])[CH2:18][CH2:19]3)[cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[c:9]([c:10]1[CH3:11])[CH2:12][C@@H:13]1[CH2:14][N:15]([CH... | CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 | CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(O)c1)C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 20.9 | [{"value": 20.9, "product": "C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.6 g (1.5 mmol) of (±)-trans-6-ethyl-2-ethoxycarbonyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.84 ml (9.0 mmol) of boron tribromide as described in example 2. The crude solid was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:2), yieldi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.c1ccccc1 | Other | null | null | null | CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2>>CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(O)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a47955b82844c658fba77886c3a3881 | CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(OC)c3)CCN(CC)C[C@H]1C2>>CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(O)c3)CCN(CC)C[C@H]1C2 | Cl.C(CC)N(C(=O)N1C=C(C2=C1C[C@@]1(CCN(C[C@H]1C2)CC)C2=CC(=CC=C2)OC)C)CCC.B(Br)(Br)Br>>C(CC)N(C(=O)N1C=C(C2=C1C[C@@]1(CCN(C[C@H]1C2)CC)C2=CC(=CC=C2)O)C)CCC | C[O:23][c:22]1[cH:21][cH:20][cH:19][c:18]([C@:17]23[CH2:16][c:15]4[n:10]([C:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:11][c:12]([CH3:13])[c:14]4[CH2:32][C@@H:31]2[CH2:30][N:27]([CH2:28][CH3:29])[CH2:26][CH2:25]3)[cH:24]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[n:10]1[cH:11]... | CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(OC)c3)CCN(CC)C[C@H]1C2 | CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(O)c3)CCN(CC)C[C@H]1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 0.56 g (1.15 mmol) of (±)-trans-dipropylaminocarbonyl-6-ethyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride were treated with 0.65 ml (7 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 7... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1c[nH]c2c1C[C@@H]1CNCCC1C2 | Other | null | null | null | CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(OC)c3)CCN(CC)C[C@H]1C2>>CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(O)c3)CCN(CC)C[C@H]1C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c4dcc751dbde49eaa01591fb6c337bfc | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1 | Cl.C(C(C)C)OC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)OC)N1)C.B(Br)(Br)Br>>Cl.C(C(C)C)OC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)O)N1)C | C[O:12][c:11]1[cH:10][cH:9][cH:8][c:7]([C@@:6]23[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:30][C@H:29]2[CH2:28][c:27]2[c:15]([nH:16][c:17]([C:18](=[O:19])[O:20][CH2:21][CH:22]([CH3:23])[CH3:24])[c:25]2[CH3:26])[CH2:14]3)[cH:13]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:13]3)[... | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1 | CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 0.56 g of (±)-trans-2-(i-butoxycarbonyl)-6-ethyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride were treated with 0.68 ml (7.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5) ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2 | Other | null | null | null | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4e872fd5a6e4a58b4e93bf3d6bae84a | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(C)CC[C@@]1(c1cccc(OC)c1)C2 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC.CC(=O)O[Na]>>C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)OC)N1)C)CC | O=[C:12]([C:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])=[N:9]Nc1ccccc1)[CH3:13].C[CH2:18][N:17]1[CH2:16][C@@H:15]2[CH2:14][CH2:11][C:10](=O)[CH2:30][C@@:21]2([c:22]2[cH:23][cH:24][cH:25][c:26]([O:27][CH3:28])[cH:29]2)[CH2:20][CH2:19]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[nH:9][c:10]2[c:11]([... | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(C)CC[C@@]1(c1cccc(OC)c1)C2 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 02f7ff219a45cc53342484f47524b7c84fa4304eb3eca6fa510465db3cfe5a17 | c19b01bf1c2954a1ff8dd269aaeb96f6c0aebc2ca18c537766f4a468d99b4eb8 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | C-[CH2;D2;+0:1]-[#7:2](-[C:3])-[C:4]-[C:5]1-[C:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=O)-[C:9]-[C:10]-1.O=[C;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:13](=[N;H0;D2;+0:14]-N-c1:c:c:c:c:c:1)-[C:15](=[O;D1;H0:16])-[#7:17](-[C:18])-[C:19]>>[C:3]-[#7:2](-[CH3;D1;+0:1])-[C:4]-[C:5]1-[C:6]-[c;H0;D3;+0:7]2:[c;H0;D3;+0:8](:[nH;D2;+0:1... | 14.7 | [{"value": 14.7, "product": "C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)OC)N1)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3 g (9.3 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.92 g (11.2 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.92 g (11.2 mmol) of CH3COONa, 2.8 g (42.8 mmol) of zinc dust and 9.3 ml of glacial acetic acid were treated as described in exa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone | null | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.c1ccccc1 | HO- | [Zn].C(C)(=O)O | null | null | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>[Zn].C(C)(=O)O>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(C)CC[C@@]1(c1cccc(OC)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a50aa20c2f95459b844fc6848f1ecb10 | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.CCN1CC[C@]2(c3cccc(OC)c3)CCC(=O)C[C@H]2C1>>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2 | Cl.C(C)N1C[C@@H]2CC(CC[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC.CC(=O)O[Na]>>C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)OC)C)CC | O=[C:12]([C:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])=[N:9]Nc1ccccc1)[CH3:13].C[CH2:27][N:26]1[CH2:25][CH2:24][C@:15]2([c:16]3[cH:17][cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23]3)[CH2:14][CH2:11][C:10](=O)[CH2:30][C@H:29]2[CH2:28]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[nH:9][c:10]2[c:11]([c:... | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.CCN1CC[C@]2(c3cccc(OC)c3)CCC(=O)C[C@H]2C1 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | a7c96afd46d67adcd8db93b524889f1b0e9b87cc8633c4df140052736ddcff04 | c19b01bf1c2954a1ff8dd269aaeb96f6c0aebc2ca18c537766f4a468d99b4eb8 | c1ccc([C@]23CCNC[C@@H]2Cc2[nH]ccc2C3)cc1 | C-[CH2;D2;+0:1]-[#7:2](-[C:3])-[C:4]-[C:5]1-[C:6]-[C:7]-[CH2;D2;+0:8]-[C;H0;D3;+0:9](=O)-[C:10]-1.O=[C;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:13](=[N;H0;D2;+0:14]-N-c1:c:c:c:c:c:1)-[C:15](=[O;D1;H0:16])-[#7:17](-[C:18])-[C:19]>>[C:3]-[#7:2](-[CH3;D1;+0:1])-[C:4]-[C:5]1-[C:6]-[C:7]-[c;H0;D3;+0:8]2:[c;H0;D3;+0:9](:[nH;D... | 16.8 | [{"value": 16.8, "product": "C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)OC)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.9 g (2.9 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-7-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride (J. Med. Chem., 35, 48, 1992), 0.9 g (3.5 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.28 g (3.5 mmol) of CH3COONa, 0.87 g (13.3 mmol) of zinc dust and 5 ml of glacial acetic acid were... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone | null | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1cc2c([nH]1)C[C@H]1C[NH]CC[C@@H]1C2 | c1ccccc1.c1cc2c([nH]1)C[C@H]1C[NH]CC[C@@H]1C2 | HO- | [Zn].C(C)(=O)O | null | null | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.CCN1CC[C@]2(c3cccc(OC)c3)CCC(=O)C[C@H]2C1>[Zn].C(C)(=O)O>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9bb3a9b9e5d04bb5b051c031681b6c2c | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2>>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(O)c3)CCN(C)C[C@@H]1C2 | C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)OC)C)CC.B(Br)(Br)Br>>C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)O)C)CC | C[O:21][c:20]1[cH:19][cH:18][cH:17][c:16]([C@@:15]23[CH2:14][c:11]4[c:10]([nH:9][c:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[c:12]4[CH3:13])[CH2:29][C@H:28]2[CH2:27][N:25]([CH3:26])[CH2:24][CH2:23]3)[cH:22]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[nH:9][c:10]2[c:11]([c:12]1[CH3:13])[CH2:14][C... | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(O)c3)CCN(C)C[C@@H]1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([C@]23CCNC[C@@H]2Cc2[nH]ccc2C3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 49.9 | [{"value": 49.9, "product": "C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)O)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.29 g (0.71 mmol) of (±)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline were treated with 0.4 ml (4.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4OH 80:12:0.8). Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c([nH]1)C[C@H]1C[NH]CC[C@@H]1C2 | Other | null | null | null | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2>>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(O)c3)CCN(C)C[C@@H]1C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a987530b45942d59d9beddfbfacbbc6 | CC(=O)C(=NNc1ccccc1)C(=O)NCc1ccccc1.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>>COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C(C1=CC=CC=C1)NC(C(C(C)=O)=NNC1=CC=CC=C1)=O>>C(C1=CC=CC=C1)NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)OC)N1)C | O=[C:30]([C:19](=[N:18]Nc1ccccc1)[C:20](=[O:21])[NH:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH3:31].C[CH2:12][N:11]1[CH2:10][CH2:9][C@@:8]2([c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33]3)[C@H:14]([CH2:13]1)[CH2:15][CH2:16][C:17](=O)[CH2:32]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C@@:8]23[CH2:... | CC(=O)C(=NNc1ccccc1)C(=O)NCc1ccccc1.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 737b89c143e6b780fcc30370e3e4edb8ee05461cfbd75d6d7efab90d7bf53785 | c19b01bf1c2954a1ff8dd269aaeb96f6c0aebc2ca18c537766f4a468d99b4eb8 | O=C(NCc1ccccc1)c1cc2c([nH]1)C[C@]1(c3ccccc3)CCNC[C@H]1C2 | C-[CH2;D2;+0:1]-[#7:2](-[C:3])-[C:4]-[C:5]1-[C:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=O)-[C:9]-[C:10]-1.O=[C;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:13](=[N;H0;D2;+0:14]-N-c1:c:c:c:c:c:1)-[C:15](=[O;D1;H0:16])-[#7:17]-[C:18]>>[C:3]-[#7:2](-[CH3;D1;+0:1])-[C:4]-[C:5]1-[C:6]-[c;H0;D3;+0:7]2:[c;H0;D3;+0:8](:[nH;D2;+0:14]:[c;H0;... | null | [] | null | null | null | null | 1 g (3.3 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.95 g (10 mmol) of N-benzyl-2-phenylhydrazono-3-oxobutyramide, 0.82 g (10 mmol) of CH3 COONa, 2.6 g (40 mmol) of zinc dust and 5 ml of glacial acetic acid were treated as described in example 1. Th... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone | null | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1cc2c(n1)C[C@H]1CC[N]C[C@H]1C2 | c1ccccc1.c1cc2c(n1)C[C@H]1CC[N]C[C@H]1C2.c1ccccc1 | HO- | [Zn].C(C)(=O)O | null | null | CC(=O)C(=NNc1ccccc1)C(=O)NCc1ccccc1.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>[Zn].C(C)(=O)O>COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2895d0d365944737af7826beeea98209 | COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1>>Cc1c(C(=O)NCc2ccccc2)[nH]c2c1C[C@@H]1CN(C)CC[C@@]1(c1cccc(O)c1)C2 | C(C1=CC=CC=C1)NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)OC)N1)C.B(Br)(Br)Br.Cl.CCOCC>>Cl.C(C1=CC=CC=C1)NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)O)N1)C | C[O:30][c:29]1[cH:28][cH:27][cH:26][c:25]([C@@:24]23[C@H:18]([CH2:17][c:16]4[c:2]([CH3:1])[c:3]([C:4](=[O:5])[NH:6][CH2:7][c:8]5[cH:9][cH:10][cH:11][cH:12][cH:13]5)[nH:14][c:15]4[CH2:32]2)[CH2:19][N:20]([CH3:21])[CH2:22][CH2:23]3)[cH:31]1>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c... | COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1 | Cc1c(C(=O)NCc2ccccc2)[nH]c2c1C[C@@H]1CN(C)CC[C@@]1(c1cccc(O)c1)C2 | null | null | CO | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(NCc1ccccc1)c1cc2c([nH]1)C[C@]1(c3ccccc3)CCNC[C@H]1C2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 0.38 g of (±)-trans-2-benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.55 ml (5.7 mmol) of boron tribromide as described in example 2. The residue was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.c1ccccc1 | Other | CO | null | null | COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1>CO>Cc1c(C(=O)NCc2ccccc2)[nH]c2c1C[C@@H]1CN(C)CC[C@@]1(c1cccc(O)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-840135d79ba844fc945788ee77b22f4f | CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>>CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C1(=CC=CC=C1)NC(C(C(C)=O)=NNC1=CC=CC=C1)=O>>C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)NC3=CC=CC=C3 | O=[C:28]([C:18](=[N:17]Nc1ccccc1)[C:19](=[O:20])[NH:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH3:29].O=[C:16]1[CH2:15][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]3)[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:33][C@@H:32]2[CH2:31][CH2:30]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH... | CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 8bedcc1ec5488f2567cac7dc6b2d45e5a0271f1fd0d1fd73222e637ddd374a05 | c19b01bf1c2954a1ff8dd269aaeb96f6c0aebc2ca18c537766f4a468d99b4eb8 | O=C(Nc1ccccc1)c1cc2c([nH]1)C[C@]1(c3ccccc3)CCNC[C@H]1C2 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[N;H0;D2;+0:4]-N-c1:c:c:c:c:c:1)-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8].O=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-1>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:3](-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]):[nH;D2;+0:4]:[c;H0;D3;+0:9]2:[c;H0;D3;+0:14]:1-[C:13]-[C:12]-[C:1... | 25.6 | [{"value": 25.6, "product": "C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)NC3=CC=CC=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.8 g (2.47 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.7 g (2.47 mmol) of N-phenyl-2-phenylhydrazono-3-oxobutyramide, 0.24 g (3 mmol) of CH3 COONa, 0.74 g (11.3 mmol) of zinc dust and 2.5 ml of glacial acetic acid were treated as described in examp... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone | null | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2 | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2.c1ccccc1 | HO- | [Zn].C(C)(=O)O | null | null | CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>[Zn].C(C)(=O)O>CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7d0772f09424c2a8285b114d4b7d007 | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 | C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)NC3=CC=CC=C3.B(Br)(Br)Br>>C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)NC3=CC=CC=C3 | C[O:12][c:11]1[cH:10][cH:9][cH:8][c:7]([C@@:6]23[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:32][C@H:31]2[CH2:30][c:29]2[c:15]([nH:16][c:17]([C:18](=[O:19])[NH:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[c:27]2[CH3:28])[CH2:14]3)[cH:13]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([OH:12]... | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 | CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Nc1ccccc1)c1cc2c([nH]1)C[C@]1(c3ccccc3)CCNC[C@H]1C2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 22.1 | [{"value": 22.1, "product": "C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)NC3=CC=CC=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.28 g of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.35 (1.9 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:2) yielding 0.06 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2.c1ccccc1 | Other | null | null | null | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aadff68fc9964d3da32320a270554fa5 | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.COc1cccc([C@]23CCN(CC4CC4)C[C@@H]2CCC(=O)C3)c1>>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC3CC3)CC[C@@]1(c1cccc(OC)c1)C2 | Cl.C1(CC1)CN1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC.CC(=O)O[Na]>>Cl.C1(CC1)CN1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)N(CC)CC | O=[C:12]([C:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])=[N:9]Nc1ccccc1)[CH3:13].O=[C:10]1[CH2:11][CH2:14][C@H:15]2[CH2:16][N:17]([CH2:18][CH:19]3[CH2:20][CH2:21]3)[CH2:22][CH2:23][C@:24]2([c:25]2[cH:26][cH:27][cH:28][c:29]([O:30][CH3:31])[cH:32]2)[CH2:33]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]... | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.COc1cccc([C@]23CCN(CC4CC4)C[C@@H]2CCC(=O)C3)c1 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC3CC3)CC[C@@]1(c1cccc(OC)c1)C2 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 02f7ff219a45cc53342484f47524b7c84fa4304eb3eca6fa510465db3cfe5a17 | c19b01bf1c2954a1ff8dd269aaeb96f6c0aebc2ca18c537766f4a468d99b4eb8 | c1ccc([C@@]23CCN(CC4CC4)C[C@H]2Cc2cc[nH]c2C3)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[N;H0;D2;+0:4]-N-c1:c:c:c:c:c:1)-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8])-[C:9].O=[C;H0;D3;+0:10]1-[C:11]-[C:12]-[C:13]-[C:14]-[CH2;D2;+0:15]-1>>[C:8]-[#7:7](-[C:9])-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c;H0;D3;+0:10]2:[c;H0;D3;+0:15](:[c;H0;D3;+0:1]:1-[C;D1;H3:2])-... | 57.9 | [{"value": 57.9, "product": "Cl.C1(CC1)CN1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)N(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.28 g (0.80 mmol) of (±)-trans-2-cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.56 g (2.14 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.131 g (1.6 mmol) of CH3COONa, 0.402 g (6.16 mmol) of zinc dust and 10 ml of glacial acetic acid were treated as... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone | null | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.C1CC1.c1ccccc1 | HO- | [Zn].C(C)(=O)O | null | null | CCN(CC)C(=O)C(=NNc1ccccc1)C(C)=O.COc1cccc([C@]23CCN(CC4CC4)C[C@@H]2CCC(=O)C3)c1>[Zn].C(C)(=O)O>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC3CC3)CC[C@@]1(c1cccc(OC)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-85e68abf33ca4928bc83045893ab7a1b | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1 | Cl.CCOCC.C(C)(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)OC)N1)C)C(C)C.B(Br)(Br)Br>>Cl.C(C)(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)O)N1)C)C(C)C | C[O:12][c:11]1[cH:10][cH:9][cH:8][c:7]([C@@:6]23[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:32][C@H:31]2[CH2:30][c:29]2[c:15]([nH:16][c:17]([C:18](=[O:19])[N:20]([CH:21]([CH3:22])[CH3:23])[CH:24]([CH3:25])[CH3:26])[c:27]2[CH3:28])[CH2:14]3)[cH:13]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]... | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1 | CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1 | null | null | CO | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 1.0 g (2.2 mmol) of (±)-trans-2-diisopropylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline were treated with 1.15 ml (12.0 mmol) of boron tribromide as described in example 2. The crude product was dissolved in MeOH and the solution brought to acidic pH wit... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2 | Other | CO | null | null | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1>CO>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d4dc502d78a2417cbeb0d77e8113c760 | CC(=O)C(=NNc1ccccc1)C(N)=O.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>>CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(N)=O)c(C)c3C[C@@H]2C1 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C1(=CC=CC=C1)NN=C(C(=O)N)C(C)=O.CC(=O)O[Na].C(C)(=O)O>>NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)OC)N1)C | O=[C:22]([C:18](=[N:17]Nc1ccccc1)[C:19]([NH2:20])=[O:21])[CH3:23].O=[C:16]1[CH2:15][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]3)[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:27][C@@H:26]2[CH2:25][CH2:24]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]3)[... | CC(=O)C(=NNc1ccccc1)C(N)=O.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(N)=O)c(C)c3C[C@@H]2C1 | null | [Zn] | null | Miscellaneous | OtherReaction | 8bedcc1ec5488f2567cac7dc6b2d45e5a0271f1fd0d1fd73222e637ddd374a05 | c19b01bf1c2954a1ff8dd269aaeb96f6c0aebc2ca18c537766f4a468d99b4eb8 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[N;H0;D2;+0:4]-N-c1:c:c:c:c:c:1)-[C:5](-[N;D1;H2:6])=[O;D1;H0:7].O=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-1>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:3](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[nH;D2;+0:4]:[c;H0;D3;+0:8]2:[c;H0;D3;+0:13]:1-[C:12]-[C:11]-[C:10]-... | null | [] | null | null | null | null | 3.24 g (10 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 6.16 g (30.0 mmol) of 2-phenylhydrazono-3-oxobutyramide, 2.46 g (7.0 mmol) of CH3COONa, 7.85 g (120.0 mmol) of zinc dust and 15 ml of glacial acetic acid were treated as described in example 1. Th... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone | null | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1 | c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2 | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2 | HO- | [Zn] | null | null | CC(=O)C(=NNc1ccccc1)C(N)=O.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>[Zn]>CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(N)=O)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e47c72c20e604a20b47414090524ffc6 | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.CCOC(=O)C(=NNc1ccccc1)C(=O)C(F)(F)F>>CCOC(=O)c1[nH]c2c(c1C(F)(F)F)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C(F)(F)F)=O.CC(=O)O[Na]>>C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C(F)(F)F)C(=O)OCC | O=[C:8]1[CH2:9][CH2:15][C@H:16]2[CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH2:22][C@:23]2([c:24]2[cH:25][cH:26][cH:27][c:28]([O:29][CH3:30])[cH:31]2)[CH2:32]1.O=[C:10]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[N:7]Nc1ccccc1)[C:11]([F:12])([F:13])[F:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[c:9]([c:10]1[C:11... | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.CCOC(=O)C(=NNc1ccccc1)C(=O)C(F)(F)F | CCOC(=O)c1[nH]c2c(c1C(F)(F)F)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 3be4aad3c4d371a76ae664baccdc8bb6992e32dbd7ed2871d79c38fbfe0b2616 | c182a26a1e4916f0df3a6716875f414b9379b6dc7bc3991b1a368fed15ba5da9 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | O=[C;H0;D3;+0:1](-[C;H0;D3;+0:2](=[N;H0;D2;+0:3]-N-c1:c:c:c:c:c:1)-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].O=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15]-[C:16]-[CH2;D2;+0:17]-1>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c;H0;D3;+0:12]2:[c;H0;D3;+0:17](:[c;H0;D3;+... | 66.6 | [{"value": 66.6, "product": "C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C(F)(F)F)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.24 g (10 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 8.65 g (30 mmol) of ethyl 2-phenylhydrazono-4,4,4-trifluoro-3-oxobutyrate, 2.46 g (30 mmol) of CH3COONa, 7.85 g (120 mmol) of zinc dust and 15 ml of glacial acetic acid were treated as described i... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone.Ester | Ester | C1CC[C@H]2C[NH]CC[C@@H]2C1.c1ccccc1 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.c1ccccc1 | HO- | [Zn].C(C)(=O)O | null | null | CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.CCOC(=O)C(=NNc1ccccc1)C(=O)C(F)(F)F>[Zn].C(C)(=O)O>CCOC(=O)c1[nH]c2c(c1C(F)(F)F)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53e465a32b0c4c70bcd0b9d12d1a9382 | CC(=O)C(=NNc1ccccc1)C(=O)N(C)C.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>>Cc1c[nH]c2c1CC1CNCCC1C2 | Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O.CN(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C.CC(=O)O[Na]>>CC1=CNC=2CC3CCNCC3CC21 | CN(C)C(=O)[C:3]([C:2](=O)[CH3:1])=[N:4]Nc1ccccc1.CC[N:10]1[CH2:9][C@@H:8]2[CH2:7][CH2:6][C:5](=O)[CH2:14][C@@:13]2(c2cccc(OC)c2)[CH2:12][CH2:11]1>>[CH3:1][c:2]1[cH:3][nH:4][c:5]2[c:6]1[CH2:7][CH:8]1[CH2:9][NH:10][CH2:11][CH2:12][CH:13]1[CH2:14]2 | CC(=O)C(=NNc1ccccc1)C(=O)N(C)C.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1 | Cc1c[nH]c2c1CC1CNCCC1C2 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 17c398210d61b4b9a698f2ca3ce9b049a4f801567b1f4664f037ab8075bab0b9 | 344df68336dcd4690b45c2b4f31b820278a1bb019f647d1126a2f0747f1fba87 | c1cc2c([nH]1)CC1CCNCC1C2 | C-C-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C@;H0;D4;+0:4]2(-c3:c:c:c:c(-O-C):c:3)-[C:5]-[C;H0;D3;+0:6](=O)-[CH2;D2;+0:7]-[C:8]-[C@H;D3;+0:9]-2-[C:10]-1.C-N(-C)-C(=O)-[C;H0;D3;+0:11](=[N;H0;D2;+0:12]-N-c1:c:c:c:c:c:1)-[C;H0;D3;+0:13](=O)-[C;D1;H3:14]>>[C;D1;H3:14]-[c;H0;D3;+0:13]1:[cH;D2;+0:11]:[nH;D2;+0:12]:[c;H0;D3;+0:6]2:[c;H0... | 84.8 | [{"value": 84.8, "product": "CC1=CNC=2CC3CCNCC3CC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g (3.1 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.33 g (10 mmol) of N, N-dimethyl-2-phenylhydrazono-3-oxobutyramide, 0.82 g (1 0 mmol) of CH3COONa, 2.6 g (40 mmol) of zinc dust and 5 ml of glacial acetic acid were treated as described in exampl... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ketone.Ether.Tertiary amide.Tertiary amine | Secondary amine | c1ccccc1.C1CC[C@H]2C[NH]CC[C@@H]2C1.c1ccccc1 | c1cc2c([nH]1)CC1CCNCC1C2 | c1cc2c([nH]1)CC1CCNCC1C2 | HO- | [Zn].C(C)(=O)O | null | null | CC(=O)C(=NNc1ccccc1)C(=O)N(C)C.CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1>[Zn].C(C)(=O)O>Cc1c[nH]c2c1CC1CNCCC1C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ae2e96f1f8c4014ac444d242c55c3da | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1 | CN(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)OC)N1)C)C.B(Br)(Br)Br.Cl.CCOCC>>Cl.CN(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)O)N1)C)C | C[O:12][c:11]1[cH:10][cH:9][cH:8][c:7]([C@@:6]23[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:28][C@H:27]2[CH2:26][c:25]2[c:15]([nH:16][c:17]([C:18](=[O:19])[N:20]([CH3:21])[CH3:22])[c:23]2[CH3:24])[CH2:14]3)[cH:13]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:13]3)[CH2:14][c:15]3[... | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1 | CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1 | null | null | CO | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc([C@@]23CCNC[C@H]2Cc2cc[nH]c2C3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 0.5 g (1.25 mmol) of (±)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline were treated with 0.725 ml (7.5 mmol) of boron tribromide as described in example 2. The etude product was dissolved in MeOH and the solution brought to acidic pH with H... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2 | Other | CO | null | null | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1>CO>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cd9b39ec611d404d9a8ea9bc73cb12d3 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CNCC[C@@]1(c1cccc(OC)c1)C2.O=Cc1ccco1>>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(Cc3ccco3)CC[C@@]1(c1cccc(OC)c1)C2 | O1C(=CC=C1)C=O.C(#N)[BH3-].[Na+].Cl.C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCNC[C@H]3C2)C2=CC(=CC=C2)OC)N1)C)CC.O1C(=CC=C1)C=O.C(#N)[BH3-].[Na+]>>Cl.C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC=2OC=CC2)C2=CC(=CC=C2)OC)N1)C)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[nH:9][c:10]2[c:11]([c:12]1[CH3:13])[CH2:14][C@@H:15]1[CH2:16][NH:17][CH2:24][CH2:25][C@@:26]1([c:27]1[cH:28][cH:29][cH:30][c:31]([O:32][CH3:33])[cH:34]1)[CH2:35]2.O=[CH:18][c:19]1[cH:20][cH:21][cH:22][o:23]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[n... | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CNCC[C@@]1(c1cccc(OC)c1)C2.O=Cc1ccco1 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(Cc3ccco3)CC[C@@]1(c1cccc(OC)c1)C2 | null | null | C(C)(=O)O.CO | Heteroatom Alkylation and Arylation | reductive amination | 6051e74c13bd3699ee2da9cef24ae529ce1510384b28dcfec56f7d71af562bec | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc([C@@]23CCN(Cc4ccco4)C[C@H]2Cc2cc[nH]c2C3)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5])-[C:9]-[C:10] | null | [] | 0 | CELSIUS | 15 | HOUR | 1.3 g (3.3 mmol) of (±)-trans-2-diethylaminocarbonyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline, 0.28 ml (4.95 mmol) of acetic acid, 0.33 ml (3.96 mmol) of 2-furaldehyde were dissolved in 50 ml of MeOH under nitrogen atmosphere. 0.415 g (6.6 mmol) of sodium cyanoborohydride ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1cc2c([nH]1)C[C@@H]1CCNC[C@H]1C2 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2 | c1cc2c([nH]1)C[C@@H]1CC[NH]C[C@H]1C2.c1ccoc1.c1ccccc1 | Other | C(C)(=O)O.CO | 0 | 15 | CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CNCC[C@@]1(c1cccc(OC)c1)C2.O=Cc1ccco1>C(C)(=O)O.CO>CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@H]1CN(Cc3ccco3)CC[C@@]1(c1cccc(OC)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e576ebaa84304ffda5a1fb2e2ebe1efc | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1 | C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)N3CCCC3.B(Br)(Br)Br>>C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)N3CCCC3 | C[O:12][c:11]1[cH:10][cH:9][cH:8][c:7]([C@@:6]23[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:30][C@H:29]2[CH2:28][c:27]2[c:15]([nH:16][c:17]([C:18](=[O:19])[N:20]4[CH2:21][CH2:22][CH2:23][CH2:24]4)[c:25]2[CH3:26])[CH2:14]3)[cH:13]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@:6]2([c:7]3[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:13]3)... | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1 | CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1cc2c([nH]1)C[C@]1(c3ccccc3)CCNC[C@H]1C2)N1CCCC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 23.3 | [{"value": 23.3, "product": "C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)N3CCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.63 g (1.37 mmol) of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.77 ml (8.22 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:0.5). ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cc2c(n1)C[C@@H]1CC[N]C[C@H]1C2.C1CC[NH]C1 | Other | null | null | null | CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1>>CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-10d566a7e6924599b73ffe5a8d4c02d6 | CC(C)(C)OC(=O)N1C(=O)CC[C@H]1CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C.CI>>C[C@@H]1C[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)N(C(=O)OC(C)(C)C)C1=O | IC.C(C)(C)(C)OC(=O)N1C(CC[C@H]1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)=O.[Li]N([Si](C)(C)C)[Si](C)(C)C>>C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C)=O | [CH2:2]1[CH2:3][C@@H:4]([CH2:5][O:6][Si:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:20]([CH3:21])([CH3:22])[CH3:23])[N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[C:32]1=[O:33].I[CH3:1]>>[CH3:1][C@@H:2]1[CH2:3][C@@H:4]([CH2:5][O:6][Si:7]([c:8]2[cH:9][cH:... | CC(C)(C)OC(=O)N1C(=O)CC[C@H]1CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C.CI | C[C@@H]1C[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)N(C(=O)OC(C)(C)C)C1=O | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_secondary | a6c1ce0a3374e4ae08505cc3e98b837620321d13fa6cd312b247b9c30998e781 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1CC[C@@H](CO[SiH](c2ccccc2)c2ccccc2)N1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9]1-[C:10]-[C:11]-[CH2;D2;+0:12]-[C:13]-1=[O;D1;H0:14]>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9]1-[C:10]-[C:11]-[C@@H;D3;+0:12](-[CH3;D1;+0:1])-[C:13]-1=[O;D1;H0:14] | 47.3 | [{"value": 47.0, "product": "C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 1 | HOUR | To a solution of (S)-1-t-butoxycarbonyl-5-t-butyldiphenylsiloxymethyl-pyrrolidine-2-one (15 g, 33 mmol) in THF (250 mL) at -78° C. a 1M solution of LiN(SiMe3)2 (35 mL, 35 mmol) was slowly added. After stirring for 1 hr, iodomethane (6.2 mL, 100 mmol) was added. The reaction mixture was allowed to stir for another 2 hr ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HI | C1CCOC1 | null | 1 | CC(C)(C)OC(=O)N1C(=O)CC[C@H]1CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C.CI>C1CCOC1>C[C@@H]1C[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)N(C(=O)OC(C)(C)C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6b339a53b1934e9da154c7d3ab813c29 | C[C@@H]1C[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)N(C(=O)OC(C)(C)C)C1=O>>C[C@@H]1C[C@@H](CO)N(C(=O)OC(C)(C)C)C1=O | C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C)=O.C(C)(=O)O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC>>C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO)C)=O | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:6][CH2:5][C@@H:4]1[CH2:3][C@@H:2]([CH3:1])[C:15](=[O:16])[N:7]1[C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]>>[CH3:1][C@@H:2]1[CH2:3][C@@H:4]([CH2:5][OH:6])[N:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15]1=[O:16] | C[C@@H]1C[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)N(C(=O)OC(C)(C)C)C1=O | C[C@@H]1C[C@@H](CO)N(C(=O)OC(C)(C)C)C1=O | null | null | C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | O=C1CCCN1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#7:4])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7:4]-[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of (3R,5S)-1-t-butoxycarbonyl-5-t-butyldiphenylsiloxymethyl-3-methyl-pyrrolidine-2-one (17.8 g, 38.1 mmol) and glacial acetic acid (2 eq) in dry THF (50 mL) at 0° C. was added a 1.0M solution of tetrabutylammonium fluoride in THF (150 mL, 150 mmol). The solution was allowed to warm room temperature and st... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | C1CC[NH]C1 | Other | C1CCOC1 | null | 8 | C[C@@H]1C[C@@H](CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)N(C(=O)OC(C)(C)C)C1=O>C1CCOC1>C[C@@H]1C[C@@H](CO)N(C(=O)OC(C)(C)C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94c314721a7e472a8dbf1f4c15f24609 | C[C@@H]1C[C@@H](CO)N(C(=O)OC(C)(C)C)C1=O.O>>C[C@@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1=O | I(=O)(=O)(=O)[O-].[Na+].C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO)C)=O.C(C)#N.C(Cl)(Cl)(Cl)Cl.O.ClCCl>>C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1C(=O)O)C)=O | [CH3:1][C@@H:2]1[CH2:3][C@@H:4]([CH2:5][OH:7])[N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C:16]1=[O:17].[OH2:6]>>[CH3:1][C@@H:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[OH:7])[N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C:16]1=[O:17] | C[C@@H]1C[C@@H](CO)N(C(=O)OC(C)(C)C)C1=O.O | C[C@@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1=O | null | [Ru](Cl)(Cl)Cl | [Cl-].[Na+].O | Heteroatom Alkylation and Arylation | OtherReaction | 345c33ef221a703d0195f5e2e95e13b23ff84fd249db06983973a14c521bda14 | 61cf901f3ab42f325ea04925d4645e2208b580d0b1f80879b3cd6caca2ef04e0 | O=C1CCCN1 | [C:1]-[C:2](-[CH2;D2;+0:3]-[O;D1;H1:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]=[O;D1;H0:14].[OH2;D0;+0:15]>>[C:1]-[C:2](-[C;H0;D3;+0:3](-[O;D1;H1:4])=[O;H0;D1;+0:15])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]=[O;D1;H0... | 54 | [{"value": 54.0, "product": "C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1C(=O)O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (3R,5S)-1-t-butoxycarbonyl-5-hydroxymethyl-3-methylpyrrolidine-2-one in a solvent mixture of acetonitrile:carbon tetrachloride:water (2:2:3, 266 mL) was added sodium periodate (3 eq, 24.0 g) and ruthenium trichloride (2.2 mol %, 0.174 g). The solution was stirred 2 hr at room temperature and then dilut... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | C1CC[NH]C1 | null | [Ru](Cl)(Cl)Cl.[Cl-].[Na+].O | null | 2 | C[C@@H]1C[C@@H](CO)N(C(=O)OC(C)(C)C)C1=O.O>[Ru](Cl)(Cl)Cl.[Cl-].[Na+].O>C[C@@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-739eba69493e45fba73186e7ab16d952 | C[C@@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1=O.O>>C[C@H](C[C@H](NC(=O)OC(C)(C)C)C(=O)O)C(=O)O | C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1C(=O)O)C)=O.O.[OH-].[Li+].O>>C(C)(C)(C)OC(=O)N[C@@H](C[C@H](C(=O)O)C)C(=O)O | [CH3:1][C@@H:2]1[CH2:3][C@@H:4]([C:13](=[O:14])[OH:15])[N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:16]1=[O:17].[OH2:18]>>[CH3:1][C@H:2]([CH2:3][C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[OH:15])[C:16](=[O:17])[OH:18] | C[C@@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1=O.O | C[C@H](C[C@H](NC(=O)OC(C)(C)C)C(=O)O)C(=O)O | null | null | C1CCOC1 | Protection | OtherReaction | 12ea568f5bbd96adab73aff3283996480961f612757e466255423c5645af0e6e | d205f1320160ea6fd9f0bda4863ee5979f7ad336699029216ee1832d3dc0743f | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[C:13]-[C:14](-[C;D1;H3:15])-[C;H0;D3;+0:16]-1=[O;D1;H0:17].[OH2;D0;+0:18]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9](-[C:13]-[C:14](-[C;D... | 99 | [{"value": 99.0, "product": "C(C)(C)(C)OC(=O)N[C@@H](C[C@H](C(=O)O)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "C(C)(C)(C)OC(=O)N[C@@H](C[C@H](C(=O)O)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (3R,5S)-1-t-Butoxycarbonyl-5-carboxy-3-methylpyrrolidine-2-one (6.2 g, 25.5 mmol) in THF (50 mL) was treated with lithium hydroxide monohydrate (3 eq, 3.20 g) and water (5 mL). After stirring for 16 hr at room temperature the THF was removed in vacuo and water (20 mL) was added. The pH was adjusted to 3 b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Substituted dicarboximide | Carbamic ester.Carboxylic acid | C1CC[NH]C1 | null | null | null | C1CCOC1 | null | null | C[C@@H]1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1=O.O>C1CCOC1>C[C@H](C[C@H](NC(=O)OC(C)(C)C)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cc72150513eb4fa69899ef3b1e23e777 | C[C@H](C[C@H](NC(=O)OC(C)(C)C)C(=O)O)C(=O)O>>C[C@H](C[C@H](N)C(=O)O)C(=O)O | C(C)(C)(C)OC(=O)N[C@@H](C[C@H](C(=O)O)C)C(=O)O>>C[C@H](C[C@H](N)C(=O)O)C(=O)O | CC(C)(C)OC(=O)[NH:5][C@@H:4]([CH2:3][C@@H:2]([CH3:1])[C:9](=[O:10])[OH:11])[C:6](=[O:7])[OH:8]>>[CH3:1][C@H:2]([CH2:3][C@H:4]([NH2:5])[C:6](=[O:7])[OH:8])[C:9](=[O:10])[OH:11] | C[C@H](C[C@H](NC(=O)OC(C)(C)C)C(=O)O)C(=O)O | C[C@H](C[C@H](N)C(=O)O)C(=O)O | null | null | FC(C(=O)O)(F)F.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | null | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | 48 | HOUR | The Boc-protected diacid, (2S, 4R)-N-t-butoxycarbonyl- 4-methyl glutamic acid, was subjected to a mixture of trifluoroacetic acid:methylene chloride (40:60, 100 mL) for 3 hr at room temperature. The volatiles were removed in vacuo and the residue was azeotroped with toluene (50 mL). Water (150 mL) was added and the aqu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | null | HO- | FC(C(=O)O)(F)F.C(Cl)Cl | null | 48 | C[C@H](C[C@H](NC(=O)OC(C)(C)C)C(=O)O)C(=O)O>FC(C(=O)O)(F)F.C(Cl)Cl>C[C@H](C[C@H](N)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c37bb1656a64973bff4ef3e79448c12 | COC(=O)Cc1cccc2ccc(OC)cc12>>COc1ccc2cccc(CCO)c2c1 | [H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].COC1=CC=C2C=CC=C(C2=C1)CC(=O)OC.O>>COC1=CC=C2C=CC=C(C2=C1)CCO | CO[C:12]([CH2:11][c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][c:14]21)=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][OH:13])[c:14]2[cH:15]1 | COC(=O)Cc1cccc2ccc(OC)cc12 | COc1ccc2cccc(CCO)c2c1 | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2ccccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:3]-[c:4] | null | [] | null | null | null | null | 3.34 g of lithium aluminum hydride are placed in a 250-cm3 flask, and ether is added gently with stirring. Using a dropping funnel, 5 g of methyl (7-methoxy-1-naphthyl)acetate previously dissolved in 50 cm3 of ether are added slowly. The reaction medium is left stirring for 30 minutes. It is poured very slowly into a m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2ccccc2c1 | Other | CCOCC | null | null | COC(=O)Cc1cccc2ccc(OC)cc12>CCOCC>COc1ccc2cccc(CCO)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-930d75a478a44c1f993455a3cf0bd573 | COc1ccc2cccc(CCO)c2c1.CS(=O)(=O)Cl>>COc1ccc2cccc(CCOS(C)(=O)=O)c2c1 | C(C)N(CC)CC.S(=O)(=O)(C)Cl.COC1=CC=C2C=CC=C(C2=C1)CCO>>S(C)(=O)(=O)OCCC1=CC=CC2=CC=C(C=C12)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][OH:13])[c:18]2[cH:19]1.Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17])[c:18]2[cH:19]1 | COc1ccc2cccc(CCO)c2c1.CS(=O)(=O)Cl | COc1ccc2cccc(CCOS(C)(=O)=O)c2c1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2ccccc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | -10 | CELSIUS | null | null | In a 250-cm3 flask, 4 g of 2-(7-methoxy-1-naphthyl)ethanol are dissolved in 100 cm3 of dichloromethane, and 3.3 cm3 of triethylamine are added. The mixture is cooled in an ice bath at -10° C. and 2.75 g of mesyl chloride are then added dropwise and with stirring. The mixture is left stirring for 30 minutes. The aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2ccccc2c1 | HCl | ClCCl | -10 | null | COc1ccc2cccc(CCO)c2c1.CS(=O)(=O)Cl>ClCCl>COc1ccc2cccc(CCOS(C)(=O)=O)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-14978e6518ec43e492e5f892cd564bb7 | CCc1ccccc1.O=C1CCC(=O)O1>>CCc1ccc(C(=O)CCC(=O)O)cc1 | Cl.C(C)C1=CC=CC=C1.[Cl-].[Al+3].[Cl-].[Cl-].C1(CCC(=O)O1)=O>>O=C(CCC(=O)O)C1=CC=C(C=C1)CC | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:14][cH:15]1.[C:7]1(=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[O:13]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1 | CCc1ccccc1.O=C1CCC(=O)O1 | CCc1ccc(C(=O)CCC(=O)O)cc1 | null | null | null | C-C Coupling | OtherReaction | 95de0079bfd4d0e2b70eac1863ad8bac063c1a1557f674f5eb3c0cde67534555 | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccccc1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11]:[c:12] | null | [] | null | null | 3 | HOUR | 5 cm3 of ethylbenzene and 2.6 g of aluminum chloride are mixed with magnetic stirring in a 50-cm3 flask. The solution is cooled in an ice bath and 1 g of succinic anhydride is then added. The reaction mixture is stirred for 1 h 30 min at a temperature of 0° C. and then for 3 h at room temperature. It is poured into ice... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | c1ccccc1.C1CCOC1 | c1ccccc1 | c1ccccc1 | null | null | null | 3 | CCc1ccccc1.O=C1CCC(=O)O1>>CCc1ccc(C(=O)CCC(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ff41cf49840a4862bb629df3394008db | CCc1ccc(C(=O)CCC(=O)O)cc1>>CCc1ccc(CCCC(=O)O)cc1 | C(C)[SiH](CC)CC.O=C(CCC(=O)O)C1=CC=C(C=C1)CC>>C(C)C1=CC=C(C=C1)CCCC(=O)O | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:14][cH:13]1)[CH2:8][CH2:9][C:10](=[O:11])[OH:12]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][C:10](=[O:11])[OH:12])[cH:13][cH:14]1 | CCc1ccc(C(=O)CCC(=O)O)cc1 | CCc1ccc(CCCC(=O)O)cc1 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 86 | HOUR | In a 100-cm3 flask, 2.5 g of 4-oxo-4-(4-ethylphenyl)butyric acid are dissolved with magnetic stirring in 19 cm3 of trifluoroacetic acid. 3.2 g of triethylsilane are added dropwise. The reaction mixture is stirred for 86 hours at room temperature. It is poured into ice. It is extracted with 3 volumes of ether. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | FC(C(=O)O)(F)F | null | 86 | CCc1ccc(C(=O)CCC(=O)O)cc1>FC(C(=O)O)(F)F>CCc1ccc(CCCC(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ebf01e6b38bc42c089b9940d05b2423f | COc1ccc2cccc(CCCOS(C)(=O)=O)c2c1.[C-]#N>>COc1ccc2cccc(CCCC#N)c2c1 | [C-]#N.[K+].S(C)(=O)(=O)OCCCC1=CC=CC2=CC=C(C=C12)OC>>COC1=CC=C2C=CC=C(C2=C1)CCCC#N | CS(=O)(=O)O[CH2:13][CH2:12][CH2:11][c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17][c:16]21.[C-:14]#[N:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][C:14]#[N:15])[c:16]2[cH:17]1 | COc1ccc2cccc(CCCOS(C)(=O)=O)c2c1.[C-]#N | COc1ccc2cccc(CCCC#N)c2c1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 18f4bbb9c586d5002707644e5539611116bc9c01fc56c5a56ec0d1b0251f5f0b | 89d1e6e004e8ba10561e22cfb8893e96c375691951aae8f42243dfb0e0a04eec | c1ccc2ccccc2c1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C-;H0;D1:4]#[N;D1;H0:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:4]#[N;D1;H0:5] | null | [] | null | null | null | null | In a 100-cm3 flask, the 3-(7-methoxy-1-naphthyl)propyl mesylate obtained in stage D is dissolved in DMSO. KCN is added and the mixture is brought to reflux for 2 h. It is allowed to cool. It is poured into a water/ice mixture. The resulting mixture is extracted with ether. The organic phase is washed with water, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Nitrile | null | null | c1ccc2ccccc2c1 | MsOH.HO- | CS(=O)C | null | null | COc1ccc2cccc(CCCOS(C)(=O)=O)c2c1.[C-]#N>CS(=O)C>COc1ccc2cccc(CCCC#N)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23a827758ec74998ac781f9b6412b1c4 | CC(=O)Cl.COc1ccc2cccc(CCCN)c2c1>>COc1ccc2cccc(CCCNC(C)=O)c2c1 | Cl.C([O-])([O-])=O.[K+].[K+].Cl.COC1=CC=C2C=CC=C(C2=C1)CCCN.C(C)(=O)Cl>>COC1=CC=C2C=CC=C(C2=C1)CCCNC(C)=O | Cl[C:15]([CH3:16])=[O:17].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][NH2:14])[c:18]2[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([CH3:16])=[O:17])[c:18]2[cH:19]1 | CC(=O)Cl.COc1ccc2cccc(CCCN)c2c1 | COc1ccc2cccc(CCCNC(C)=O)c2c1 | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 2 | HOUR | After 0.005 mol (equivalent to 1.26 g) of 3-(7-methoxy-1-naphthyl)propylamine hydrochloride has been dissolved in 20 cm3 of water, 0.015 mol of potassium carbonate is added. The amine precipitates. Thereafter, 50 cm3 of chloroform are added and 0.010 mol of acetyl chloride is added dropwise. The medium is left stirring... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1 | HCl | O | null | 2 | CC(=O)Cl.COc1ccc2cccc(CCCN)c2c1>O>COc1ccc2cccc(CCCNC(C)=O)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-97b454fff5d740a79020045a749f01a7 | COc1ccc2cccc(CCCNC(C)=O)c2c1.O=C(Cl)c1ccccc1>>COc1ccc2cc(C(=O)c3ccccc3)cc(CCCNC(C)=O)c2c1 | COC1=CC=C2C=CC=C(C2=C1)CCCNC(C)=O.C(C1=CC=CC=C1)(=O)Cl>>COC1=CC=C2C=C(C=C(C2=C1)CCCNC(C)=O)C(C1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:17][c:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([CH3:24])=[O:25])[c:26]2[cH:27]1.Cl[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][c:18]([CH2:1... | COc1ccc2cccc(CCCNC(C)=O)c2c1.O=C(Cl)c1ccccc1 | COc1ccc2cc(C(=O)c3ccccc3)cc(CCCNC(C)=O)c2c1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 12bfc1cb494a0014608d71eb38cabea029a6bf3a3526b0cc7babc0ad4f29f3e1 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:8](:[c:7]:[c:6]):[c:9]:[c:10] | null | [] | null | null | null | null | By reacting N-[3-(7-methoxy-1-naphthyl)propyl]acetamide obtained in Example 1 with benzoyl chloride, the compound of the title is obtained.
Conditions: See reaction.notes.procedure_details.
Workup: the compound of the title is obtained | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccccc1 | HCl | null | null | null | COc1ccc2cccc(CCCNC(C)=O)c2c1.O=C(Cl)c1ccccc1>>COc1ccc2cc(C(=O)c3ccccc3)cc(CCCNC(C)=O)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-412e177c658c41ed889ff8abc67dfcca | CC(=O)Cl.COc1ccc2cccc(CCCNC(C)=O)c2c1>>COc1ccc2cc(C(C)=O)cc(CCCNC(C)=O)c2c1 | COC1=CC=C2C=CC=C(C2=C1)CCCNC(C)=O.C(C)(=O)Cl>>COC1=CC=C2C=C(C=C(C2=C1)CCCNC(C)=O)C(C)=O | Cl[C:9]([CH3:10])=[O:11].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:12][c:13]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([CH3:19])=[O:20])[c:21]2[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9]([CH3:10])=[O:11])[cH:12][c:13]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([CH3:19])=[O:20])[c:21]2[cH:22]1 | CC(=O)Cl.COc1ccc2cccc(CCCNC(C)=O)c2c1 | COc1ccc2cc(C(C)=O)cc(CCCNC(C)=O)c2c1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 12bfc1cb494a0014608d71eb38cabea029a6bf3a3526b0cc7babc0ad4f29f3e1 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | null | null | By reacting N-[3-(7-methoxy-1-naphthyl)propyl]acetamide obtained in Example 1 with acetyl chloride, the compound of the title is obtained.
Conditions: See reaction.notes.procedure_details.
Workup: the compound of the title is obtained | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HCl | null | null | null | CC(=O)Cl.COc1ccc2cccc(CCCNC(C)=O)c2c1>>COc1ccc2cc(C(C)=O)cc(CCCNC(C)=O)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f0a8b290beed4251bf550b18be2b89c0 | Cc1cc(C2C=CCC2)c(S(C)(=O)=O)cc1C(=O)Cl.N=C(N)N>>Cc1cc(C2C=CCC2)c(S(C)(=O)=O)cc1C(=O)N=C(N)N | CC1=C(C(=O)Cl)C=C(C(=C1)C1C=CCC1)S(=O)(=O)C.NC(=N)N.[Cl-].NC(=[NH2+])N.[Na].CC1C(C(=O)OC)=CC(=C(C1=S(=O)=O)Br)C.C1=CCCC1>>NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C1C=CCC1)C)=O)N | Cl[C:17]([c:16]1[c:2]([CH3:1])[cH:3][c:4]([CH:5]2[CH:6]=[CH:7][CH2:8][CH2:9]2)[c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15]1)=[O:18].[NH:19]=[C:20]([NH2:21])[NH2:22]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]2[CH:6]=[CH:7][CH2:8][CH2:9]2)[c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][c:16]1[C:17](=[O:18])[N:19]=[C:20]([NH2:21... | Cc1cc(C2C=CCC2)c(S(C)(=O)=O)cc1C(=O)Cl.N=C(N)N | Cc1cc(C2C=CCC2)c(S(C)(=O)=O)cc1C(=O)N=C(N)N | null | null | COCCOC | Acylation | OtherReaction | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | C1=CC(c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C:7](-[N;D1;H2:8])=[NH;D1;+0:9]>>[N;D1;H2:6]-[C:7](-[N;D1;H2:8])=[N;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | A fresh guanidine solution prepared from 5.6 g of guanidinium chloride and 1.6 g of sodium in 40 ml of ethylene glycol dimethyl ether is added to a solution of 1.2 g of 2-methyl-4-(1-cyclopentene-3-yl)-5-methylsulfonylbenzoyl chloride [obtainable by reaction of methyl 2-methyl-4-bromo-5-methyl-sulfonyl-benzoate with cy... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1ccccc1.C1=CCCC1 | HCl | COCCOC | null | 2 | Cc1cc(C2C=CCC2)c(S(C)(=O)=O)cc1C(=O)Cl.N=C(N)N>COCCOC>Cc1cc(C2C=CCC2)c(S(C)(=O)=O)cc1C(=O)N=C(N)N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c4cda8c04324a8b924c6c3506ced1f7 | CS(=O)(=O)O>>CS(=O)(=O)[O-] | NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C1C=CCC1)C)=O)N.CS(=O)(=O)O>>NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C1C=CCC1)C)=O)N.CS(=O)(=O)[O-] | [CH3:1][S:2](=[O:3])(=[O:4])[OH:5]>>[CH3:1][S:2](=[O:3])(=[O:4])[O-:5] | CS(=O)(=O)O | CS(=O)(=O)[O-] | null | null | CC(=O)C | Oxidation | OtherReaction | 8411f9fce1f185c5c08a89a741e7494817f2d5e55ac6ad2b663e4ffb9ef8fbab | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | null | [C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[OH;D1;+0:5]>>[C;D1;H3:1]-[#16:2](-[O-;H0;D1:5])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | 700 mg of N-diaminomethylene-2-methyl-4-(1-cyclopenten-3-yl)-5-methylsulfonylbenzamide [which can be prepared according to Example 1; m.p. 212°-214°] are dissolved in 20 ml of acetone, and 6.1 ml of methanesulfonic acid are added, while stirring. Filtration and lyophilization give N-diaminomethylene-2-methyl-4-(1-cyclo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(=O)C | null | null | CS(=O)(=O)O>CC(=O)C>CS(=O)(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90f641ecf797467592f5799ba146037c | CS(=O)(=O)c1cc(C(=O)Cl)ccc1C1C=CCC1.N=C(N)N>>CS(=O)(=O)c1cc(C(=O)N=C(N)N)ccc1C1C=CCC1 | CS(=O)(=O)C=1C=C(C(=O)Cl)C=CC1C1C=CCC1.NC(=N)N>>NC(=NC(C1=CC(=C(C=C1)C1C=CCC1)S(=O)(=O)C)=O)N | Cl[C:8]([c:7]1[cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:16]([CH:17]2[CH:18]=[CH:19][CH2:20][CH2:21]2)[cH:15][cH:14]1)=[O:9].[NH:10]=[C:11]([NH2:12])[NH2:13]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([C:8](=[O:9])[N:10]=[C:11]([NH2:12])[NH2:13])[cH:14][cH:15][c:16]1[CH:17]1[CH:18]=[CH:19][CH2:20][CH2:21]1 | CS(=O)(=O)c1cc(C(=O)Cl)ccc1C1C=CCC1.N=C(N)N | CS(=O)(=O)c1cc(C(=O)N=C(N)N)ccc1C1C=CCC1 | null | null | null | Acylation | OtherReaction | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | C1=CC(c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C:7](-[N;D1;H2:8])=[NH;D1;+0:9]>>[N;D1;H2:6]-[C:7](-[N;D1;H2:8])=[N;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Analogously to Example 1, by reaction of 2.2 g of 3-methylsulfonyl-4-(1-cyclopenten-3-yl)-benzoyl chloride with guanidine, customary working up gives N-diaminomethylene-3-methylsulfonyl-4-(1-cyclopenten-3-yl)benzamide, which can be recrystallized from acetonitrile/diethylether, m.p. 188°-190°.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1ccccc1.C1=CCCC1 | HCl | null | null | null | CS(=O)(=O)c1cc(C(=O)Cl)ccc1C1C=CCC1.N=C(N)N>>CS(=O)(=O)c1cc(C(=O)N=C(N)N)ccc1C1C=CCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9a7eb44685f468d8f6ff10d7448f0ce | C#Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O.N=C(N)N>>C=Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O | [H][H].NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C#C)C)=O)N.CC1=C(C(=O)OC)C=C(C(=C1)Br)S(=O)(=O)C.CC1=C(C(=O)OC)C=C(C(=C1)C#C)S(=O)(=O)C.NC(=N)N>>NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C=C)C)=O)N | NC(N)=N[C:8]([c:7]1[c:5]([CH3:6])[cH:4][c:3]([C:2]#[CH:1])[c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:14]1)=[O:9].[NH:10]=[C:11]([NH2:12])[NH2:13]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH3:6])[c:7]([C:8](=[O:9])[N:10]=[C:11]([NH2:12])[NH2:13])[cH:14][c:15]1[S:16]([CH3:17])(=[O:18])=[O:19] | C#Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O.N=C(N)N | C=Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O | null | [Pd].C(=O)([O-])[O-].[Ca+2] | CN(C)C=O | Acylation | OtherReaction | f724adc768b346031737a96e026428a011a44d8640356509ca79dfcc8ffff7d9 | 96baac3eb89613d5226811d099c12ee84b213a1838d7b0a18d41caca2f6cdb3f | c1ccccc1 | N-C(-N)=N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6](-[C;H0;D2;+0:7]#[CH;D1;+0:8]):[c:9]:[c:10]:1.[N;D1;H2:11]-[C:12](-[N;D1;H2:13])=[NH;D1;+0:14]>>[CH2;D1;+0:8]=[CH;D2;+0:7]-[c:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D2;+0:14]=[C:12](-[N;D1;H2:11])-[N;D1;H2:13]):[c:10]:[c:9]:1 | null | [] | null | null | null | null | 6.0 g of N-diaminomethylene-2-methyl-4-ethynyl-5-methylsulfonylbenzamide, m.p. 223°-226° [obtainable by reaction of methyl 2-methyl-4-bromo-5-methylsulfonyl-benzoate with Li acetylide to give methyl 2-methyl-4-ethynyl-5-methylsulfonyl-benzoate and subsequent reaction with guanidine] are dissolved in 300 ml of DMF and h... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Alkyne | Vinyl | null | null | c1ccccc1 | Other | [Pd].C(=O)([O-])[O-].[Ca+2].CN(C)C=O | null | null | C#Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O.N=C(N)N>[Pd].C(=O)([O-])[O-].[Ca+2].CN(C)C=O>C=Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa0f7fe1f9b24e3d99fc0030bef32d89 | COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]>>COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1N | [N+](=O)([O-])C=1C=C(C=CC1OC)\C=C/C1=CC(=C(C(=C1)OC)OC)OC>>NC=1C=C(C=CC1OC)\C=C/C1=CC(=C(C(=C1)OC)OC)OC | O=[N+:23]([O-])[c:22]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6](/[CH:7]=[CH:8]\[c:9]2[cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]2)[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]\[c:9]2[cH:10][c:11]([O:12][CH3:13])[c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]2)[cH:21][c... | COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-] | COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1N | null | [Zn] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=C\c1ccccc1)\c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 49.3 | [{"value": 49.3, "product": "NC=1C=C(C=CC1OC)\\C=C/C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.1, "product": "NC=1C=C(C=CC1OC)\\C=C/C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 700 mg of (Z)-1-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethene were dissolved in 35 ml of acetic acid, and 7 g of zinc were added thereto and stirred for one hour. The reaction liquid was filtered, concentrated and purified by silica gel column chromatography (dichloromethane:hexane=2:1 by volume) to obtai... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Zn].C(C)(=O)O | null | 1 | COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]>[Zn].C(C)(=O)O>COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7682e2cee87a4592adfa5b6aefdb5c2b | COc1cc(C[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc(OC)c1OC.O=Cc1ccc(Cl)c([N+](=O)[O-])c1>>COc1cc(/C=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC | [Cl-].[Na+].[N+](=O)([O-])C=1C=C(C=O)C=CC1Cl.[Br-].COC=1C=C(CP(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C1OC)OC.[H-].[Na+]>>[N+](=O)([O-])C=1C=C(C=CC1Cl)\C=C/C1=CC(=C(C(=C1)OC)OC)OC | c1ccc([PH](c2ccccc2)(c2ccccc2)[CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:19]([O:20][CH3:21])[cH:18]2)cc1.O=[CH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[CH:6]=[CH:7]\[c:8]2[cH:9][cH:10][c:11]([Cl:12])[c:13]([N+:14](=[O:15])[O-:16])[c... | COc1cc(C[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc(OC)c1OC.O=Cc1ccc(Cl)c([N+](=O)[O-])c1 | COc1cc(/C=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC | null | null | C(C)(=O)O.C1=CC=CC=C1 | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C\c1ccccc1)\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6](-[CH2;D2;+0:7]-[PH](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:8]>>[c:3]:[c:2](/[CH;D2;+0:1]=[CH;D2;+0:7]\[c:6](:[c:5]):[c:8]):[c:4] | 50.9 | [{"value": 50.9, "product": "[N+](=O)([O-])C=1C=C(C=CC1Cl)\\C=C/C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g of 3-nitro-4-chlorobenzaldehyde and 2.8 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 260 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature. The reaction liquid was neutralized with ac... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C1=CC=CC=C1 | null | null | COc1cc(C[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc(OC)c1OC.O=Cc1ccc(Cl)c([N+](=O)[O-])c1>C(C)(=O)O.C1=CC=CC=C1>COc1cc(/C=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d94aaed8109c4f10b8798228c27f900e | COc1cc(C[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc(OC)c1OC.Cc1ccc(C=O)cc1[N+](=O)[O-]>>COc1cc(/C=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | [Cl-].[Na+].[N+](=O)([O-])C=1C=C(C=O)C=CC1C.[Br-].COC=1C=C(CP(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C1OC)OC.[H-].[Na+]>>[N+](=O)([O-])C=1C=C(C=CC1C)\C=C/C1=CC(=C(C(=C1)OC)OC)OC | c1ccc([PH](c2ccccc2)(c2ccccc2)[CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:19]([O:20][CH3:21])[cH:18]2)cc1.O=[CH:7][c:8]1[cH:9][cH:10][c:11]([CH3:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[CH:6]=[CH:7]\[c:8]2[cH:9][cH:10][c:11]([CH3:12])[c:13]([N+:14](=[O:15])[O-:16])... | COc1cc(C[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc(OC)c1OC.Cc1ccc(C=O)cc1[N+](=O)[O-] | COc1cc(/C=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | null | null | C(C)(=O)O.C1=CC=CC=C1 | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C\c1ccccc1)\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6](-[CH2;D2;+0:7]-[PH](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:8]>>[c:3]:[c:2](/[CH;D2;+0:1]=[CH;D2;+0:7]\[c:6](:[c:5]):[c:8]):[c:4] | 49.6 | [{"value": 49.6, "product": "[N+](=O)([O-])C=1C=C(C=CC1C)\\C=C/C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g of 3-nitro-4-methylbenzaldehyde and 3.3 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 302 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature. The reaction liquid was neutralized with ac... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C1=CC=CC=C1 | null | null | COc1cc(C[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc(OC)c1OC.Cc1ccc(C=O)cc1[N+](=O)[O-]>C(C)(=O)O.C1=CC=CC=C1>COc1cc(/C=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8e7d1432c9064f03900f1184067040ee | COc1cc(/C=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC>>COc1cc(/C=C\c2ccc(C)c(N)c2)cc(OC)c1OC | [N+](=O)([O-])C=1C=C(C=CC1C)\C=C/C1=CC(=C(C(=C1)OC)OC)OC>>NC=1C=C(C=CC1C)\C=C/C1=CC(=C(C(=C1)OC)OC)OC | O=[N+:14]([O-])[c:13]1[c:11]([CH3:12])[cH:10][cH:9][c:8](/[CH:7]=[CH:6]\[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:20]([O:21][CH3:22])[c:17]([O:18][CH3:19])[cH:16]2)[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[CH:6]=[CH:7]\[c:8]2[cH:9][cH:10][c:11]([CH3:12])[c:13]([NH2:14])[cH:15]2)[cH:16][c:17]([O:18][CH3:19])[c:20]1[O:21][CH3:22... | COc1cc(/C=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | COc1cc(/C=C\c2ccc(C)c(N)c2)cc(OC)c1OC | null | [Zn] | C(C)(=O)O.ClCCl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=C\c1ccccc1)\c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 49.1 | [{"value": 46.5, "product": "NC=1C=C(C=CC1C)\\C=C/C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.1, "product": "NC=1C=C(C=CC1C)\\C=C/C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 65 mg of (Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl) ethene were dissolved in 4 ml of acetic acid and 4 ml of dichloromethane, and 300 mg of zinc were added thereto and stirred for one hour. The reaction liquid was filtered, concentrated and purified by silica gel column chromatography (dichloromethane:he... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Zn].C(C)(=O)O.ClCCl | null | 1 | COc1cc(/C=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC>[Zn].C(C)(=O)O.ClCCl>COc1cc(/C=C\c2ccc(C)c(N)c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-404ecda70ed446ed84b005842ee3c774 | COc1ccc(/C=C(\C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]>>COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C=C(C=CC1OC)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC>>[N+](=O)([O-])C=1C=C(C=CC1OC)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[C:8](\[C:9]#[N:10])[c:11]2[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]2)[cH:23][c:24]1[N+:25](=[O:26])[O-:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[C:8](/[C:9]#[N:10])[c:11]2[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[c:19]... | COc1ccc(/C=C(\C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-] | COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-] | null | null | C(C)#N | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C(=Cc1ccccc1)c1ccccc1 | null | 49.8 | [{"value": 49.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1OC)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.8, "product": "[N+](=O)([O-])C=1C=C(C=CC1OC)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.0 g of (Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile were dissolved in 500 ml of acetonitrile and exposed to visible light rays for 60 minutes. The reaction liquid was concentrated and crystallized from ethyl acetate to obtain 996 mg of the intended compound. The yield was 49%.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | null | C(C)#N | null | null | COc1ccc(/C=C(\C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]>C(C)#N>COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed51f9672c6c4e2fa5a22df5f59b9419 | COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]>>COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1N | [N+](=O)([O-])C=1C=C(C=CC1OC)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC>>NC=1C=C(C=CC1OC)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | O=[N+:25]([O-])[c:24]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6](/[CH:7]=[C:8](/[C:9]#[N:10])[c:11]2[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]2)[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[C:8](/[C:9]#[N:10])[c:11]2[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[c:19]([O:20... | COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-] | COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1N | null | [Zn] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=Cc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.5 | [{"value": 99.0, "product": "NC=1C=C(C=CC1OC)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "NC=1C=C(C=CC1OC)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 500 mg of (E)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile were dissolved in 25 ml of acetic acid, and 5 g of zinc were added thereto and stirred for 30 minutes at room temperature. The reaction liquid was filtered and then concentrated. The concentrated liquid was purified by silica gel co... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Zn].C(C)(=O)O | null | 0.5 | COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1[N+](=O)[O-]>[Zn].C(C)(=O)O>COc1ccc(/C=C(/C#N)c2cc(OC)c(OC)c(OC)c2)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0522bf4210474a18b5909e43c5604b2d | COc1cc(CC#N)cc(OC)c1OC.Cc1ccc(C=O)cc1[N+](=O)[O-]>>COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | [N+](=O)([O-])C=1C=C(C=O)C=CC1C.COC=1C=C(C=C(C1OC)OC)CC#N.[OH-].[Na+]>>[N+](=O)([O-])C=1C=C(C=CC1C)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7]#[N:8])[cH:20][c:21]([O:22][CH3:23])[c:24]1[O:25][CH3:26].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([CH3:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]/[c:10]2[cH:11][cH:12][c:13]([CH3:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)... | COc1cc(CC#N)cc(OC)c1OC.Cc1ccc(C=O)cc1[N+](=O)[O-] | COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | null | [Cl-].C(CCCCCCC)[N+](C)(CCCCCCCC)CCCCCCCC | ClCCl.O | C-C Coupling | OtherReaction | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C/c1ccccc1)\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[N;D1;H0:5]#[C:6]/[C;H0;D3;+0:7](=[CH;D2;+0:1]\[c:2](:[c:3]):[c:4])-[c:8](:[c:9]):[c:10] | 14.1 | [{"value": 14.1, "product": "[N+](=O)([O-])C=1C=C(C=CC1C)\\C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1C)\\C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5.0 g of 3-nitro-4-methylbenzaldehyde, 6.27 g of 3,4,5-trimethoxyphenylacetonitrile, 1.44 g of sodium hydroxide and 500 mg of trioctylmethylammonium chloride were dissolved in 25 ml of water and 500 ml of dichloromethane. The mixture was stirred vigorously for 3 hours at room temperature. The ice water was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1.c1ccccc1 | HO- | [Cl-].C(CCCCCCC)[N+](C)(CCCCCCCC)CCCCCCCC.ClCCl.O | null | 3 | COc1cc(CC#N)cc(OC)c1OC.Cc1ccc(C=O)cc1[N+](=O)[O-]>[Cl-].C(CCCCCCC)[N+](C)(CCCCCCCC)CCCCCCCC.ClCCl.O>COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-57d4b77be99049839cad797e5f680f84 | COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC>>COc1cc(/C(C#N)=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | [N+](=O)([O-])C=1C=C(C=CC1C)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC>>[N+](=O)([O-])C=1C=C(C=CC1C)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]/[c:10]2[cH:11][cH:12][c:13]([CH3:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[cH:20][c:21]([O:22][CH3:23])[c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]\[c:10]2[cH:11][cH:12][c:13]([CH3:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)... | COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | COc1cc(/C(C#N)=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C(=C\c1ccccc1)\c1ccccc1 | null | 7.2 | [{"value": 7.2, "product": "[N+](=O)([O-])C=1C=C(C=CC1C)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.38 g of (Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 500 ml of acetone and the mixture was reacted in a photochemical apparatus (visible light) for 1 hour. The reaction mixture was concentrated and a quarter of it was purified on a silica gel plate to give 100 mg of th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | null | CC(=O)C | null | null | COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC>CC(=O)C>COc1cc(/C(C#N)=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed7ebba3c7234968814e60ccc77d8c58 | COc1cc(/C(C#N)=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC>>COc1cc(/C(C#N)=C\c2ccc(C)c(N)c2)cc(OC)c1OC | [N+](=O)([O-])C=1C=C(C=CC1C)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC>>NC=1C=C(C=CC1C)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | O=[N+:16]([O-])[c:15]1[c:13]([CH3:14])[cH:12][cH:11][c:10](/[CH:9]=[C:6](\[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:19]([O:20][CH3:21])[cH:18]2)[C:7]#[N:8])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]\[c:10]2[cH:11][cH:12][c:13]([CH3:14])[c:15]([NH2:16])[cH:17]2)[cH:18][c:19]([O:20][... | COc1cc(/C(C#N)=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC | COc1cc(/C(C#N)=C\c2ccc(C)c(N)c2)cc(OC)c1OC | null | [Zn] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=C\c1ccccc1)\c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 78 | [{"value": 78.0, "product": "NC=1C=C(C=CC1C)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 84 mg of (E)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 8 ml of acetic acid then zinc was added to the mixture. The mixture was stirred vigorously for 1 hour then filtered and concentrated. The residue was purified on a silica gel plate (dichloromethane) to give 60 mg of t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Zn].C(C)(=O)O | null | 1 | COc1cc(/C(C#N)=C\c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC>[Zn].C(C)(=O)O>COc1cc(/C(C#N)=C\c2ccc(C)c(N)c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0713a93170224a6cbc1dbbb08f705236 | COc1cc(/C(C#N)=C/c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC>>COc1cc(/C(C#N)=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC | [N+](=O)([O-])C=1C=C(C=CC1Cl)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC>>[N+](=O)([O-])C=1C=C(C=CC1Cl)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]/[c:10]2[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[cH:20][c:21]([O:22][CH3:23])[c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]\[c:10]2[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[c... | COc1cc(/C(C#N)=C/c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC | COc1cc(/C(C#N)=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC | null | null | CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C(=C\c1ccccc1)\c1ccccc1 | null | 26.7 | [{"value": 26.7, "product": "[N+](=O)([O-])C=1C=C(C=CC1Cl)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.5 g of (Z)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 500 ml of acetone and the solution was reacted in a photochemical apparatus (visible light) for 1 hour. The reaction mixture was concentrated and a half of it was purified on a silica gel plate to give 400 mg of the i... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | null | CC(=O)C | null | null | COc1cc(/C(C#N)=C/c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC>CC(=O)C>COc1cc(/C(C#N)=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7addc825e2ab4603a52563957c8959bb | COc1cc(/C(C#N)=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC>>COc1cc(/C(C#N)=C\c2ccc(Cl)c(N)c2)cc(OC)c1OC | [N+](=O)([O-])C=1C=C(C=CC1Cl)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC>>NC=1C=C(C=CC1Cl)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC | O=[N+:16]([O-])[c:15]1[c:13]([Cl:14])[cH:12][cH:11][c:10](/[CH:9]=[C:6](\[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:19]([O:20][CH3:21])[cH:18]2)[C:7]#[N:8])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[C:6]([C:7]#[N:8])=[CH:9]\[c:10]2[cH:11][cH:12][c:13]([Cl:14])[c:15]([NH2:16])[cH:17]2)[cH:18][c:19]([O:20][CH... | COc1cc(/C(C#N)=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC | COc1cc(/C(C#N)=C\c2ccc(Cl)c(N)c2)cc(OC)c1OC | null | [Zn] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | C(=C\c1ccccc1)\c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 33.6 | [{"value": 33.0, "product": "NC=1C=C(C=CC1Cl)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.6, "product": "NC=1C=C(C=CC1Cl)/C=C(/C#N)\\C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | (E)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 330 mg was dissolved in 8 ml of acetic acid then zinc was added to the mixture. The mixture was stirred vigorously for one hour then filtered and concentrated. The residue was purified on a silica gel plate (dichloromethane) to give 102 mg of ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Zn].C(C)(=O)O | null | 1 | COc1cc(/C(C#N)=C\c2ccc(Cl)c([N+](=O)[O-])c2)cc(OC)c1OC>[Zn].C(C)(=O)O>COc1cc(/C(C#N)=C\c2ccc(Cl)c(N)c2)cc(OC)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9dbcb3fceb74a8f85be0773e105b776 | CCOc1ccc2[nH]c(=O)c(C(=O)OC)c(-c3ccc4c(c3)OCO4)c2c1.COc1ccccc1CCl>>CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2Cc1ccccc1OC | ClC(=O)CC(=O)OC.NC1=C(C=C(C=C1)OCC)C(C1=CC2=C(C=C1)OCO2)=O.C(C)(C)(C)OC(=O)NC1=CC=C(C=C1)OCC.C(C)(C)(C)[Li].COC1=C(CCl)C=CC=C1.O1COC2=C1C=CC(=C2)C2=C(C(NC1=CC=C(C=C21)OCC)=O)C(=O)OC.NC1=C(C=C(C=C1)OCC)C(C1=CC2=C(C=C1)OCO2)=O.C1OC=2C=C(C=O)C=CC2O1>>O1COC2=C1C=CC(=C2)C2=C(C(N(C1=CC=C(C=C21)OCC)CC2=C(C=CC=C2)OC)=O)C(=O)OC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10](-[c:11]1[cH:12][cH:13][c:14]3[c:15]([cH:16]1)[O:17][CH2:18][O:19]3)[c:20]([C:21](=[O:22])[O:23][CH3:24])[c:25](=[O:26])[nH:27]2.Cl[CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][c:34]1[O:35][CH3:36]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:... | CCOc1ccc2[nH]c(=O)c(C(=O)OC)c(-c3ccc4c(c3)OCO4)c2c1.COc1ccccc1CCl | CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2Cc1ccccc1OC | null | null | C([O-])([O-])=O.[K+].[K+].C1CCOC1.C[O-].[Na+].ClCCl.CN(C)C=O.C(C)N(C(C)C)C(C)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1472a48c3f9f0239b8165e6233084b0a0375c831b35ecd4cc0ba8f1bdeda2bcb | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1cc(-c2ccc3c(c2)OCO3)c2ccccc2n1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c:12](:[c:13]):[c:14]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12](:[c:13]):[c:14] | null | [] | null | null | 4 | HOUR | A 50% solution of 0.4 g of 2-methoxybenzyl chloride ("A") in dichloromethane is added to a solution of 0.4 g of methyl 4-(1,3-benzodioxol-5-yl)-1, 2-dihydro-6-ethoxy-2-oxoquinoline-3-carboxylate (obtainable by reacting 1-amino-2-(3,4-methylenedioxybenzoyl)-4-ethoxybenzene and methyl chloroformylacetate in dichlorometha... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ccccc2c1 | c1ccc2ncccc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1.c1ccccc1 | HCl | C([O-])([O-])=O.[K+].[K+].C1CCOC1.C[O-].[Na+].ClCCl.CN(C)C=O.C(C)N(C(C)C)C(C)C | null | 4 | CCOc1ccc2[nH]c(=O)c(C(=O)OC)c(-c3ccc4c(c3)OCO4)c2c1.COc1ccccc1CCl>C([O-])([O-])=O.[K+].[K+].C1CCOC1.C[O-].[Na+].ClCCl.CN(C)C=O.C(C)N(C(C)C)C(C)C>CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2Cc1ccccc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3aafaa9bc09e4d7e91b49eec25c1596b | CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)O)c(=O)n2Cc1ccccc1OC.CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2Cc1ccccc1OC>>CCOc1ccc2nc(OCc3ccccc3OC)c(C(=O)O)c(-c3ccc4c(c3)OCO4)c2c1 | O1COC2=C1C=CC(=C2)C2=C(C(N(C1=CC=C(C=C21)OCC)CC2=C(C=CC=C2)OC)=O)C(=O)O.O1COC2=C1C=CC(=C2)C2=C(C(N(C1=CC=C(C=C21)OCC)CC2=C(C=CC=C2)OC)=O)C(=O)OC.[OH-].[K+]>>O1COC2=C1C=CC(=C2)C2=C(C(=NC1=CC=C(C=C21)OCC)OCC2=C(C=CC=C2)OC)C(=O)O | COc1ccccc1C[n:8]1[c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:35][c:34]2[c:24](-[c:25]2[cH:26][cH:27][c:28]3[c:29]([cH:30]2)[O:31][CH2:32][O:33]3)[c:20]([C:21](=[O:22])[OH:23])[c:9]1=[O:10].CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19]>>[CH3:1][CH2... | CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)O)c(=O)n2Cc1ccccc1OC.CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2Cc1ccccc1OC | CCOc1ccc2nc(OCc3ccccc3OC)c(C(=O)O)c(-c3ccc4c(c3)OCO4)c2c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | cea3ffee7a800a1fbb53f73f4eeba415dfcf0713f519e40a4bf0949df30e9354 | e6e00eccd20c93f6516a052b248fe94c4455c8eeab86eb83aaffcb64ebfad30a | c1ccc(COc2cc(-c3ccc4c(c3)OCO4)c3ccccc3n2)cc1 | C-C-O-c1:c:c:c2:c(:c:1):c(-c1:c:c:c3:c(:c:1)-O-C-O-3):c(-C(=O)-O-C):c(=O):n:2-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-c1:c:c:c:c:c:1-C-[n;H0;D3;+0:5]1:[c:6](:[c:7]):[c:8]:[c:9]:[c:10](-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[c;H0;D3;+0:14]:1=[O;H0;D1;+0:15]>>[O;D1;H0:12]=[C:11](-[O;D1;H1:13])-[c:10]1:[c:9]:[c:8]:[c:6](:[c:7... | null | [] | null | null | null | null | A solution of 0.5 g of methyl 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carboxylate and 6 ml of 5N KOH in 10 ml of methanol is boiled under reflux for 2 hours. The usual working up results in 4-(1,3-benzodioxol-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxoquinoline-3-carb... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Ether.Ether | Ether | c1ccccc1.c1ccc2ncccc2c1.c1ccc2c(c1)OCO2.c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccc2c(c1)OCO2 | HO- | CO | null | null | CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)O)c(=O)n2Cc1ccccc1OC.CCOc1ccc2c(c1)c(-c1ccc3c(c1)OCO3)c(C(=O)OC)c(=O)n2Cc1ccccc1OC>CO>CCOc1ccc2nc(OCc3ccccc3OC)c(C(=O)O)c(-c3ccc4c(c3)OCO4)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9faac40bc60f4f9481fb3e21ace77f7b | Cc1cc(O)cc(=O)o1.ClCc1ccccc1>>Cc1cc(OCc2ccccc2)cc(=O)o1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Cl.OC1=CC(OC(=C1)C)=O.C1COCCOCCOCCOCCOCCO1>>C(C1=CC=CC=C1)OC1=CC(OC(=C1)C)=O | [CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:13][c:14](=[O:15])[o:16]1.Cl[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14](=[O:15])[o:16]1 | Cc1cc(O)cc(=O)o1.ClCc1ccccc1 | Cc1cc(OCc2ccccc2)cc(=O)o1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=c1cc(OCc2ccccc2)cco1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[#8;a:9]:[c:10]:[c:11]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#8;a:9]:[c:10]:[c:11]:1):[c:4] | null | [] | null | null | 4.5 | HOUR | 124.4 g (0.900 mol) potassium carbonate and 63 ml (0.547 mol) benzyl chloride were added in succession to a solution of 56.7 g (0.450 mol) 4-hydroxy-6-methyl-2H-pyran-2-one and 1.0 g (0.004 mol) 18-crown-6 in 900 ml anhydrous dimethyl-formamide. It was stirred vigorously for 4.5 hours at an internal temperature of 70°-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccocc1.c1ccccc1 | HCl | CN(C=O)C | null | 4.5 | Cc1cc(O)cc(=O)o1.ClCc1ccccc1>CN(C=O)C>Cc1cc(OCc2ccccc2)cc(=O)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1aa3216ef4c4a1fb552fae720596c8e | Cc1cc(OCc2ccccc2)cc(=O)o1.O=Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1>>O=c1cc(OCc2ccccc2)cc(CC(O)c2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1 | C(C)(C)NC(C)C.C(CCC)[Li].Cl.C(C1=CC=CC=C1)OC=1C=C(C=O)C=CC1OCC1=CC=CC=C1.C(C1=CC=CC=C1)OC1=CC(OC(=C1)C)=O.[Cl-].[NH4+]>>C(C1=CC=CC=C1)OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)=O | [O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]([CH3:15])[o:40]1.[CH:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:30]([O:31][CH2:32][c:33]2[cH:34][cH:35][cH:36][cH:37][cH:38]2)[cH:39]1>>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6... | Cc1cc(OCc2ccccc2)cc(=O)o1.O=Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | O=c1cc(OCc2ccccc2)cc(CC(O)c2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 995c7a5cbf37230035b00de18cd91aae550f6b3916b2678b4c13427cfa9d9370 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | O=c1cc(OCc2ccccc2)cc(CCc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5])-[c:8](:[c:9]):[c:10] | 68 | [{"value": 68.0, "product": "C(C1=CC=CC=C1)OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "C(C1=CC=CC=C1)OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | -78 | CELSIUS | 45 | MINUTE | A solution of 10.1 g (14.0 ml, 100 mmol) diisopropylamine in 150 ml tetrahydrofuran was mixed under nitrogen at -78° C. with 41.0 ml (95 mmol) butyllithium (2.3M in n-hexane). It was allowed to reach 0° C. for a short time and immediately cooled again to -78° C. After a dropwise addition of a solution of 19.0 g (88 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccocc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | O1CCCC1 | -78 | 0.75 | Cc1cc(OCc2ccccc2)cc(=O)o1.O=Cc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1>O1CCCC1>O=c1cc(OCc2ccccc2)cc(CC(O)c2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-65ca9c80774841d78cc6437f7406abeb | O=c1cc(OCc2ccccc2)cc(CC(O)c2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1>>O=c1cc(O)cc(CC(O)c2ccc(O)c(O)c2)o1 | C(C1=CC=CC=C1)OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)=O.[H][H]>>OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)O)O)=O | c1ccc(C[O:5][c:4]2[cH:3][c:2](=[O:1])[o:19][c:7]([CH2:8][CH:9]([OH:10])[c:11]3[cH:12][cH:13][c:14]([O:15]Cc4ccccc4)[c:16]([O:17]Cc4ccccc4)[cH:18]3)[cH:6]2)cc1>>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([CH2:8][CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([OH:15])[c:16]([OH:17])[cH:18]2)[o:19]1 | O=c1cc(OCc2ccccc2)cc(CC(O)c2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1 | O=c1cc(O)cc(CC(O)c2ccc(O)c(O)c2)o1 | null | [Ni] | C(C)O | Deprotection | OtherReaction | 329bfe228dff858bb5ec6a65da59966cadb6acb2bd1c2a9dde293efaaf235784 | c285c154f8bc0deded5c4c3d0a24c6fc98572ede850256e8900bb913cdb4dd9a | O=c1cccc(CCc2ccccc2)o1 | C(-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#8;a:5]:[c:6]:[c:7]:1)-c1:c:c:c:c:c:1.[c:8]:[c:9](-[O;H0;D2;+0:10]-C-c1:c:c:c:c:c:1):[c:11](-[O;H0;D2;+0:12]-C-c1:c:c:c:c:c:1):[c:13]>>[OH;D1;+0:10]-[c:9](:[c:8]):[c:11](-[OH;D1;+0:12]):[c:13].[OH;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#8;a:5]:[c:6]:[c:7]:1 | 70 | [{"value": 70.0, "product": "OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 35.6 g (66.6 mmol) 4-benzyloxy-6-[2-[3,4-dibenzyloxyphenyl)-2-hydroxy-ethyl)]-2H-pyran-2-one (VI) was hydrogenated for 6 hours at room temperature under a hydrogen pressure of 44 mbar in 1200 ml ethanol using 10 g W2 Raney nickel. After taking up 4.4 l hydrogen the catalyst was removed by suction filtration and it was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccocc1.c1ccccc1 | Other | [Ni].C(C)O | null | null | O=c1cc(OCc2ccccc2)cc(CC(O)c2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)o1>[Ni].C(C)O>O=c1cc(O)cc(CC(O)c2ccc(O)c(O)c2)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2778a9f71b614c56aa952dc1c3b7fac4 | O=c1cc(O)cc(CC(O)c2ccc(O)c(O)c2)o1>>O=c1cc(O)cc(C=Cc2ccc(O)c(O)c2)o1 | C1(=CC=CC=C1)C.C(=O)OCC.CO.Cl.OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)O)O)=O.O1CCCC1>>OC=1C=C(C=CC1O)C=CC1=CC(=CC(O1)=O)O | O[CH:9]([CH2:8][c:7]1[cH:6][c:4]([OH:5])[cH:3][c:2](=[O:1])[o:18]1)[c:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([OH:16])[cH:17]1>>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([OH:16])[cH:17]2)[o:18]1 | O=c1cc(O)cc(CC(O)c2ccc(O)c(O)c2)o1 | O=c1cc(O)cc(C=Cc2ccc(O)c(O)c2)o1 | null | null | C(=O)O | Functional Group Interconversion | OtherReaction | 24323612d5486e9fd0704523d3a93bd4db9c6e3295677a91ceb1aea86b497d01 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | O=c1cccc(C=Cc2ccccc2)o1 | O-[CH;D3;+0:1](-[CH2;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6])-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[CH;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6]):[c:9] | null | [] | null | null | null | null | 2 ml 3N HCl was added to a suspension of 8.0 g (30 mmol) 4-hydroxy-6-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-2H-pyran-2-one VII and 300 ml tetrahydrofuran. The resulting clear solution was heated for 2-3 hours under reflux until it was no longer possible to detect starting material. (TLC control, mobile solvent: tolue... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccocc1.c1ccccc1 | HO- | C(=O)O | null | null | O=c1cc(O)cc(CC(O)c2ccc(O)c(O)c2)o1>C(=O)O>O=c1cc(O)cc(C=Cc2ccc(O)c(O)c2)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1e6e90adf2744bfa6b435f6c7114ace | c1ccc([S+](c2ccccc2)c2ccccc2)cc1>>c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | ClCCl.ClCCl.[K+].FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.[Cl-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1>>FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(S(=O)(=O)[O-])F.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | [cH:30]1[cH:31][cH:32][c:33]([S+:34]([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:47][cH:48]1>>[cH:30]1[cH:31][cH:32][c:33]([S+:34]([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:47][cH:48]1 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | null | [] | null | null | 30 | MINUTE | To a suspension of perfluorooctanesulfonic acid potassium salt (24.64 g, 46.1 mmol) in water (150 ml) at room temperature under nitrogen was added dropwise triphenylsulfonium chloride (50% aqueous solution, 27.50 g) over 15 minutes. After stirring the suspension for 30 minutes, dichloromethane (75 ml) was added and the... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | O | null | 0.5 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1>O>c1ccc([S+](c2ccccc2)c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36355329f50b4fba91d75f1d3bd8c47f | O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1>>O=S(=O)([O-])c1ccc(C(F)(F)F)cc1 | [Cl-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.ClCCl.FC(C1=CC=C(C=C1)S(=O)(=O)Cl)(F)F.C([O-])([O-])=O.[Na+].[Na+]>>FC(C1=CC=C(C=C1)S(=O)(=O)[O-])(F)F.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | Cl[S:2](=[O:1])(=[O:3])[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1>>[O:1]=[S:2](=[O:3])([O-:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1 | O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1 | O=S(=O)([O-])c1ccc(C(F)(F)F)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | 6c113db978119dd30ec9ac70e3a1ccab457b8adfa2d854ef650cc9d0d938808f | 5664dc87dc3eea7f40384c1c98932c2b6f77a01ae2083f96843fa9d662971745 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[O;-;D1;H0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | A suspension of 4-trifluoromethylbenzenesulfonyl chloride (20.53 g, 83.9 mmol) in water (150 ml) containing sodium carbonate (9.43 g, 88.10 mmol) was heated at reflux for 22 hours. After cooling to room temperature, triphenylsulfonium chloride (50% aqueous solution, 50.00 g) was added over 15 minutes. After stirring th... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | c1ccccc1 | null | O | null | 0.5 | O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1>O>O=S(=O)([O-])c1ccc(C(F)(F)F)cc1 |
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