dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-533ba5fdbb8c431592ef5123fe96aa69 | c1cc2nonc2cc1CCN1CCC2(CC1)OCCO2>>O=C1CCN(CCc2ccc3nonc3c2)CC1 | N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(OCCO1)CC2.Cl.[OH-].[Na+]>>N1=C2C(=NO1)C=C(C=C2)CCN2CCC(CC2)=O | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]3[n:12][o:13][n:14][c:15]3[cH:16]1)[CH2:17][CH2:18]2>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][c:8]2[cH:9][cH:10][c:11]3[n:12][o:13][n:14][c:15]3[cH:16]2)[CH2:17][CH2:18]1 | c1cc2nonc2cc1CCN1CCC2(CC1)OCCO2 | O=C1CCN(CCc2ccc3nonc3c2)CC1 | null | null | null | Miscellaneous | Ketal hydrolysis to ketone | e1a500d6eaeee849f0995e0019a6dfe1a95ed3b02d3dd703f66c280b12a3ba9a | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCN(CCc2ccc3nonc3c2)CC1 | C1-C-[O;H0;D2;+0:1]-[C;H0;D4;+0:2]2(-O-1)-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-2>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1 | 88 | [{"value": 88.0, "product": "N1=C2C(=NO1)C=C(C=C2)CCN2CCC(CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "N1=C2C(=NO1)C=C(C=C2)CCN2CCC(CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8-[2-(benzofurazan-5-yl)ethyl]1,4-dioxa-8-aza spiro[4.5]decane (20.0 g, 69.1 mmol) in 1N aqueous HCl (200 mL, 200 mmol) was heated to reflux for 1.5 hr. The cooled solution was adjusted to pH 8.5 with 40% aqueous sodium hydroxide and extracted with ethyl acetate (250 mL then 100 mL). The combined extracts... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CC2(CC[NH]1)OCCO2 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2nonc2c1 | HO- | null | null | null | c1cc2nonc2cc1CCN1CCC2(CC1)OCCO2>>O=C1CCN(CCc2ccc3nonc3c2)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a21fa8981c44402c978c9e3b60a57916 | CC(=O)c1cc(S(=O)(=O)O)ccc1O.O=P(Cl)(Cl)Cl>>CC(=O)c1cc(S(=O)(=O)Cl)ccc1O | O=P(Cl)(Cl)Cl.C(C)(=O)C=1C=C(C=CC1O)S(=O)(=O)O.C(C)N(CC)CC.CN(C(C)=O)C>>C(C)(=O)C=1C=C(C=CC1O)S(=O)(=O)Cl | O[S:7]([c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:13]([OH:14])[cH:12][cH:11]1)(=[O:8])=[O:9].O=P(Cl)(Cl)[Cl:10]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([S:7](=[O:8])(=[O:9])[Cl:10])[cH:11][cH:12][c:13]1[OH:14] | CC(=O)c1cc(S(=O)(=O)O)ccc1O.O=P(Cl)(Cl)Cl | CC(=O)c1cc(S(=O)(=O)Cl)ccc1O | null | null | C1CCCS1(=O)=O.C(C)#N | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | c1ccccc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7] | 72 | [{"value": 72.0, "product": "C(C)(=O)C=1C=C(C=CC1O)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 30 | MINUTE | A mixture of 3-acetyl-4-hydroxy-benzenesulfonic acid (3.0 g) (prepared according to T. Pfliegel et. al., Acta Chim. Acad. Sci. Hung., 98(2) 231-240(1978)) in tetramethylenesulfone (6 mL) and acetonitrile (6 mL) under argon was treated with triethylamine (1.94 mL) and N,N-dimethylacetamide (0.32 mL). This was stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccccc1 | HCl | C1CCCS1(=O)=O.C(C)#N | 10 | 0.5 | CC(=O)c1cc(S(=O)(=O)O)ccc1O.O=P(Cl)(Cl)Cl>C1CCCS1(=O)=O.C(C)#N>CC(=O)c1cc(S(=O)(=O)Cl)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fde626f3f44f49ed940d53fb770966eb | CC(=O)c1cc(S(=O)(=O)Cl)ccc1O.CN>>CNS(=O)(=O)c1ccc(O)c(C(C)=O)c1 | CN.C(C)(=O)C=1C=C(C=CC1O)S(=O)(=O)Cl>>CNS(=O)(=O)C1=CC(=C(C=C1)O)C(C)=O | Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([C:12]([CH3:13])=[O:14])[cH:15]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([C:12]([CH3:13])=[O:14])[cH:15]1 | CC(=O)c1cc(S(=O)(=O)Cl)ccc1O.CN | CNS(=O)(=O)c1ccc(O)c(C(C)=O)c1 | null | null | C(C)#N | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 5 | MINUTE | A saturated solution of monomethyl amine in acetonitrile cooled to 0° C. was treated with 3-acetyl-4-hydroxy-benzenesulfonyl chloride. The mixture was stirred 5 min, concentrated .in vacuo to an oil, disolved in ethyl acetate and treated with 1N aqueous HCl. The organic portion was separated, concentrated, filtered thr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(C)#N | null | 0.083333 | CC(=O)c1cc(S(=O)(=O)Cl)ccc1O.CN>C(C)#N>CNS(=O)(=O)c1ccc(O)c(C(C)=O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c78c7f624e5742638633f445aa36dd71 | CNS(=O)(=O)c1ccc(O)c(C(C)=O)c1>>CC(=O)c1cc(S(N)(=O)=O)ccc1O | CN.CNS(=O)(=O)C1=CC(=C(C=C1)O)C(C)=O>>C(C)(=O)C=1C=C(C=CC1O)S(=O)(=O)N | C[NH:8][S:7]([c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:13]([OH:14])[cH:12][cH:11]1)(=[O:9])=[O:10]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11][cH:12][c:13]1[OH:14] | CNS(=O)(=O)c1ccc(O)c(C(C)=O)c1 | CC(=O)c1cc(S(N)(=O)=O)ccc1O | null | null | null | Deprotection | OtherReaction | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1ccccc1 | C-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | The title compound was prepared in a similar manner as for the preparation of N-methyl-3-acetyl-4-hydroxy-benzenesulfonic acid amide, but substituting ammonia for mono methyl amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1 | Other | null | null | null | CNS(=O)(=O)c1ccc(O)c(C(C)=O)c1>>CC(=O)c1cc(S(N)(=O)=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-71eeed9b844b4aeeb9efd514647a519b | N#CC1CCc2ccccc2C1=O.O=C1CCc2cc(Br)ccc2C1>>N#Cc1ccc2c(c1)CCC(=O)C2 | BrC=1C=C2CCC(CC2=CC1)=O.OP(=O)(O)O.BrC1C(C2=CC=CC=C2CC1)=O.C(#N)C1C(C2=CC=CC=C2CC1)=O.[C-]#N.[Na+]>>C(#N)C=1C=C2CCC(CC2=CC1)=O | O=C1c2ccccc2CCC1[C:2]#[N:1].Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11](=[O:12])[CH2:13]2>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11](=[O:12])[CH2:13]2 | N#CC1CCc2ccccc2C1=O.O=C1CCc2cc(Br)ccc2C1 | N#Cc1ccc2c(c1)CCC(=O)C2 | null | null | O.C1(=CC=CC=C1)C.CC#N | C-C Coupling | OtherReaction | 4dbcddd4339f014f13a5c77b5afce971a5c943f20cd349b0a63848fe0ff40795 | 6fc614cab9a280cfa3094baf5e9e9e8ba799786beee319d1462a77b89ba84a1b | O=C1CCc2ccccc2C1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=C1-C(-[C;H0;D2;+0:6]#[N;D1;H0:7])-C-C-c2:c:c:c:c:c:2-1>>[N;D1;H0:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 64 | HOUR | A flame dried 1 liter round bottom flask with argon inlet, digital thermometer, and magnetic stir bar, was charged with a 68% NaCN/alumina mixture (21.22 g, 433 mmol)(NaCN and alumina were ground together in a morter and pestle according to the procedure of Dalton et al. J. Org. Chem., 44, (24) 4443(1979)), and tetraki... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Nitrile | Nitrile | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HBr | O.C1(=CC=CC=C1)C.CC#N | 80 | 64 | N#CC1CCc2ccccc2C1=O.O=C1CCc2cc(Br)ccc2C1>O.C1(=CC=CC=C1)C.CC#N>N#Cc1ccc2c(c1)CCC(=O)C2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e921f8075fbe4ea6afd048375329645b | O=C(O)Cc1ccc(Br)cc1>>O=C1CCc2cc(Br)ccc2C1 | BrC1=CC=C(C=C1)CC(=O)O.C(Cl)Cl.C(C(=O)Cl)(=O)Cl>>BrC=1C=C2CCC(CC2=CC1)=O | O[C:2](=[O:1])[CH2:12][c:11]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[CH2:12]1 | O=C(O)Cc1ccc(Br)cc1 | O=C1CCc2cc(Br)ccc2C1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 3ddaea1c7c620a4fe69840fbaf35984962bf3a7647bbe3b5aee72759a4c57fb5 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1CCc2ccccc2C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](:[c:7]:[c:8])-[C:9]-[C:10]-1 | 88 | [{"value": 88.0, "product": "BrC=1C=C2CCC(CC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 16 | HOUR | A single neck 3 liter round bottom flask under an Ar atmosphere was charged with 4-bromo-phenyl acetic acid (250.0 g, 1.15 m), methylene chloride (1.5 L), and dimethylformamide (0.5 mL). This magnetically stirred solution was cooled to 0° C. and treated dropwise with oxalyl chloride (156 mL, 1.74 m). The reaction was a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | null | CN(C=O)C | 0 | 16 | O=C(O)Cc1ccc(Br)cc1>CN(C=O)C>O=C1CCc2cc(Br)ccc2C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0e4735efef654a35bcd736238a290eb5 | N#CBr.Oc1ccccc1>>N#COc1ccccc1 | C(C)N(CC)CC.O.N#CBr.C1(=CC=CC=C1)O>>C1(=CC=CC=C1)OC#N | Br[C:2]#[N:1].[OH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[N:1]#[C:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | N#CBr.Oc1ccccc1 | N#COc1ccccc1 | null | null | C(Cl)(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 68547639d24a8d0d4becd4eec3119b97229f928b953d4cdf965d8ede06889848 | e3940423b90b64130f6bcdd46f50032c408f6ed90b61b7be1270a05338ca4707 | c1ccccc1 | Br-[C;H0;D2;+0:1]#[N;D1;H0:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 82 | [{"value": 82.0, "product": "C1(=CC=CC=C1)OC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "C1(=CC=CC=C1)OC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | The title compound was prepared by a modification of the procedure described in Organic. Syntheses, 61, 35 (1983). A 3-necked, 2 L R.B. flask, equipped with a 500 ml pressure equalized dropping funnel, a mechanical stirrer and a thermometer, was charged with water and coled in an ice-salt bath. Cyanogen bromide (189.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(Cl)(Cl)(Cl)Cl | null | 0.083333 | N#CBr.Oc1ccccc1>C(Cl)(Cl)(Cl)Cl>N#COc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-029cb54ee0db440182eaf2a51a27ca49 | COc1cc2c(cc1OC)C1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)NCC2=O.O=[N+]([O-])c1ccc(CBr)cc1>>COc1cc2c(cc1OC)C1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)N(Cc1ccc([N+](=O)[O-])cc1)CC2=O | Cl.COC=1C=C2C(CNC3(CCN(CC3)CCC3=CC=C(C=C3)[N+](=O)[O-])C2=CC1OC)=O.[N+](=O)([O-])C1=CC=C(CBr)C=C1>>COC=1C=C2C(CN(C3(CCN(CC3)CCC3=CC=C(C=C3)[N+](=O)[O-])C2=CC1OC)CC1=CC=C(C=C1)[N+](=O)[O-])=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[C:11]1([CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]3)[CH2:26][CH2:27]1)[NH:28][CH2:39][C:40]2=[O:41].Br[CH2:29][c:30]1[cH:31][cH:32][c:33]([N+:34](=[O:35])[O-:36])[cH:37][cH:38]1>>[CH3:1][O:2][c:3... | COc1cc2c(cc1OC)C1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)NCC2=O.O=[N+]([O-])c1ccc(CBr)cc1 | COc1cc2c(cc1OC)C1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)N(Cc1ccc([N+](=O)[O-])cc1)CC2=O | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 332179fcbe7e60ac5b22795ed34b43e3fbba8607c5322571693f64bd5d4b25f9 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CN(Cc2ccccc2)C2(CCN(CCc3ccccc3)CC2)c2ccccc21 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]1(-[C:7])-[NH;D2;+0:8]-[C:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]-1>>[C:5]-[C:6]1(-[C:7])-[c:13]:[c:12]-[C:10](=[O;D1;H0:11])-[C:9]-[N;H0;D3;+0:8]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 6,7-dimethoxy-1'-[2-(4-nitrophenyl)ethyl]-spiro[1,2,3,4-tetrahydro-isoquinoline- 1,4'-piperidin]-4-one hydrochloride (0.33 g) sodium bicarbonate (0.1 g) and p-nitrobenzylbromide (0.25 g) in ethanol were refluxed for 18 hours. The reaction was concentrated and chromotographed on silica (methylene chloride/m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNC21CC[NH]CC1 | c1ccc2c(c1)CC[NH]C21CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CC[NH]C21CC[NH]CC1 | HBr | C(C)O | null | null | COc1cc2c(cc1OC)C1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)NCC2=O.O=[N+]([O-])c1ccc(CBr)cc1>C(C)O>COc1cc2c(cc1OC)C1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)N(Cc1ccc([N+](=O)[O-])cc1)CC2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2a63d696abee4d668b2c02629b6701c1 | CC(Cl)OC(=O)Cl.COc1cc2c(cc1OC)C1(CCN(C)CC1)NCC2=O>>COc1cc2c(cc1OC)C1(CCNCC1)NCC2=O.Cl.Cl | COC=1C=C2C(CNC3(CCN(CC3)C)C2=CC1OC)=O.CN(C1=CC=CC2=CC=CC(=C12)N(C)C)C.ClC(=O)OC(C)Cl>>Cl.Cl.COC=1C=C2C(CNC3(CCNCC3)C2=CC1OC)=O | CC(OC(=O)[Cl:21])[Cl:22].C[N:14]1[CH2:13][CH2:12][C:11]2([c:6]3[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([O:9][CH3:10])[cH:7]3)[C:19](=[O:20])[CH2:18][NH:17]2)[CH2:16][CH2:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[C:11]1([CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)[NH:17][CH2:18][C:19]2=[O:20].[ClH:2... | CC(Cl)OC(=O)Cl.COc1cc2c(cc1OC)C1(CCN(C)CC1)NCC2=O | COc1cc2c(cc1OC)C1(CCNCC1)NCC2=O.Cl.Cl | null | null | ClC(C)Cl | Miscellaneous | OtherReaction | f496ec46a8d9a111edb5476691130a9b19c374da36355b9fec1dc8a00d73d555 | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | O=C1CNC2(CCNCC2)c2ccccc21 | C-C(-[Cl;H0;D1;+0:1])-O-C(=O)-[Cl;H0;D1;+0:2].C-[N;H0;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7]>>[C:5]-[C:4]-[NH;D2;+0:3]-[C:6]-[C:7].[ClH;D0;+0:2].[ClH;D0;+0:1] | null | [] | null | null | null | null | To a solution of 6,7-dimethoxy-1'-methylspiro[1,2,3,4-tetrahydroisoquinoline-1,4'-piperidin]-4-one (Helv. Chem. Acta., 588, Fasc. 1, Nr. 8 (1975)) (1.0 g) and N,N,N',N'-tetramethyl-1,8-napthalenediamine (0.9 g) in dichloroethane at 0° C. under nitrogen was added 1-chloroethyl chloroformate (9.5 ml) and the mixture stir... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccc2c(c1)CCNC21CC[NH]CC1 | c1ccc2c(c1)CCNC21CCNCC1 | c1ccc2c(c1)CCNC21CCNCC1 | HO- | ClC(C)Cl | null | null | CC(Cl)OC(=O)Cl.COc1cc2c(cc1OC)C1(CCN(C)CC1)NCC2=O>ClC(C)Cl>COc1cc2c(cc1OC)C1(CCNCC1)NCC2=O.Cl.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-baf929c61250483a893cc2ec64cc1564 | CC(=O)Cl.CC(=O)N1CCc2ccccc21>>CC(=O)N1CCc2cc(C(C)O)ccc21 | C(C)(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-].C(C)(=O)N1CCC2=CC=CC=C12.[BH4-].[Na+]>>C(C)(=O)N1CCC2=CC(=CC=C12)C(O)C | Cl[C:10]([CH3:11])=[O:12].[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:13][cH:14][c:15]21>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([CH:10]([CH3:11])[OH:12])[cH:13][cH:14][c:15]21 | CC(=O)Cl.CC(=O)N1CCc2ccccc21 | CC(=O)N1CCc2cc(C(C)O)ccc21 | null | null | O.ClCCCl | C-C Coupling | OtherReaction | c6d2cd97d5cb4726e065bb09c16c0309b4ca2f578eca9db13fc5d3007e4d515f | 647ebe07e90ecd5a44f8749d46ed292ac06a1f71bf16845e77953537ff6c8509 | c1ccc2c(c1)CCN2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H0;D1;+0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[CH;D3;+0:1](-[OH;D1;+0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 90 | [{"value": 90.0, "product": "C(C)(=O)N1CCC2=CC(=CC=C12)C(O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "C(C)(=O)N1CCC2=CC(=CC=C12)C(O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-Acetyl-2,3-dihydro-1H-indole (16.1 g, 0.1 mol) in 1,2-dichloroethane (60 ml) was added dropwise to refluxing mixture of acetyl chloride (21.33 ml, 23.55 g, 0.3 mol) and aluminum chloride (40.0 g, 0.3 mol) in 1,2-dichloroethane (40 ml). The mixture was heated under reflux for 2 hours, cooled and poured onto crushed ic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Secondary alcohol | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | O.ClCCCl | null | 1 | CC(=O)Cl.CC(=O)N1CCc2ccccc21>O.ClCCCl>CC(=O)N1CCc2cc(C(C)O)ccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b220a1fa1ec249d1b183fede606be887 | C=Cc1ccc2c(c1)CCN2C(C)=O.O>>CC(=O)N1CCc2cc(CCO)ccc21 | O.O.C[N+](C)(C)[O-].B.O1CCCC1.C(C)(=O)N1CCC2=CC(=CC=C12)C=C.Cl>>C(C)(=O)N1CCC2=CC(=CC=C12)CCO | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([CH:10]=[CH2:11])[cH:13][cH:14][c:15]21.[OH2:12]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([CH2:10][CH2:11][OH:12])[cH:13][cH:14][c:15]21 | C=Cc1ccc2c(c1)CCN2C(C)=O.O | CC(=O)N1CCc2cc(CCO)ccc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 85d75aa1dd362b099b4b39479f03f14b00166a1fb51d9d56b8f6baeb24dcfc65 | a5a4442c0146f1e327c2cfdba212bc8e7bdfa3323799e3415d591a1ff54424ea | c1ccc2c(c1)CCN2 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH2;D0;+0:6]>>[OH;D1;+0:6]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 83.1 | [{"value": 55.0, "product": "C(C)(=O)N1CCC2=CC(=CC=C12)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "C(C)(=O)N1CCC2=CC(=CC=C12)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Borane-tetrahydrofuran complex (1.0M in THF, 20 ml, 20 mmol) was added dropwise to an ice cooled solution of 1-acetyl-2,3-dihydro-5-ethenyl-1H-indole (5.61 g, 30 mmol) in TEF (150 ml). The mixture was stirred at 0° C. for 30 minute then at room temperature for 1 hr. Trimethylamine N-oxide dihydrate (8.88 g, 80 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Primary alcohol | null | null | c1ccc2c(c1)CC[NH]2 | null | O | 0 | 0.5 | C=Cc1ccc2c(c1)CCN2C(C)=O.O>O>CC(=O)N1CCc2cc(CCO)ccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dc5425ac52664f45bee53207c04e56a8 | CS(=O)(=O)Cl.O=C1CCCCCO1>>CC(C)(O)CCCCCOS(C)(=O)=O | C[Mg]Cl.O1C(CCCCC1)=O.Cl.CS(=O)(=O)Cl.O.N1=CC=CC=C1>>CS(=O)(=O)OCCCCCC(C)(O)C | Cl[S:11]([CH3:12])(=[O:13])=[O:14].[C:2]1(=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][S:11]([CH3:12])(=[O:13])=[O:14] | CS(=O)(=O)Cl.O=C1CCCCCO1 | CC(C)(O)CCCCCOS(C)(=O)=O | null | null | ClCCl.C1CCOC1 | Acylation | OtherReaction | 1cf47001c23d63877a00fe08ac974721502899ae4312a922075d829725dc8f78 | 674e2c337c6f56110cdd71dff14cbf99505b23e19b6bf8b966d37880631380f9 | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[O;H0;D2;+0:9]-[C:10]-[C:11]>>[C:5]-[C:6]-[C;H0;D4;+0:7](-[C;D1;H3:12])(-[C;D1;H3:13])-[OH;D1;+0:8].[C:11]-[C:10]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 98 | [{"value": 98.0, "product": "CS(=O)(=O)OCCCCCC(C)(O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Methylmagnesium chloride (2.8M in THF, 21 ml, 60 mmol) was added dropwise to an ice-cooled solution of 2-oxepanone (2.22 ml, 2.28 g, 20 mmol) in THF (20 ml). The mixture was stirred for 1 hour, then water (100 ml) was added dropwise. The pH was adjusted to 7 with aqueous HCl (3N) and the mixture was extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Sulfonyl halide | Mesylate.Tertiary alcohol | C1CCCOCC1 | null | null | null | ClCCl.C1CCOC1 | null | 1 | CS(=O)(=O)Cl.O=C1CCCCCO1>ClCCl.C1CCOC1>CC(C)(O)CCCCCOS(C)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7b01503b061045e3ad4bbf9bbd4cf9a4 | CC(O)CCCCCO.CS(=O)(=O)Cl>>CC(O)CCCCCOS(C)(=O)=O | C(CCCCC(C)O)O.N1=CC=CC=C1.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCCC(C)O | [CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].Cl[S:10]([CH3:11])(=[O:12])=[O:13]>>[CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][S:10]([CH3:11])(=[O:12])=[O:13] | CC(O)CCCCCO.CS(=O)(=O)Cl | CC(O)CCCCCOS(C)(=O)=O | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | 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] | 60 | [{"value": 60.0, "product": "CS(=O)(=O)OCCCCCC(C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "CS(=O)(=O)OCCCCCC(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | (±)-Heptan-1,6-diol (1.06 g, 8 mmol) and pyridine (1.36 ml, 1.33 g, 16.8 mmol) were dissolved in dichloromethane (20 ml) and the mixture was cooled in ice. Methanesulfonyl chloride (0.65 ml, 0.96 g, 8.4 mmol) was added dropwise and the mixture was stirred at room temperature for 18 hours. Dichloromethane (50 ml) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | ClCCl | null | 18 | CC(O)CCCCCO.CS(=O)(=O)Cl>ClCCl>CC(O)CCCCCOS(C)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f8aaccce3b704807855d9507b5581a57 | CS(=O)(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4c(c3)CCN4)CC1)O2>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4c(c3)CCN4NS(C)(=O)=O)CC1)O2 | CS(=O)(=O)Cl.N1CCC2=CC(=CC=C12)CCN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)NS(=O)(=O)C.N1=CC=CC=C1.Cl>>Cl.CS(=O)(=O)NN1CCC2=CC(=CC=C12)CCN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)NS(=O)(=O)C | Cl[S:31]([CH3:32])(=[O:33])=[O:34].[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]4[c:25]([cH:26]3)[CH2:27][CH2:28][NH:29]4)[CH2:35][CH2:36]1)[O:37]2>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7... | CS(=O)(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4c(c3)CCN4)CC1)O2 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4c(c3)CCN4NS(C)(=O)=O)CC1)O2 | null | null | C(C)O | Acylation | OtherReaction | 06c2bdae9852bfb8684e6a6e6b3e555b2a30607acd965d61eb794f4fc43887f1 | f97d6678c95315aa11b104cc9d7bf59a78c8194f3c832310ec8cda71a4927447 | O=C1CC2(CCN(CCc3ccc4c(c3)CCN4)CC2)Oc2ccccc21 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[#7:11]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[c:7]:[c:6]-1:[c:5] | 40 | [{"value": 40.0, "product": "Cl.CS(=O)(=O)NN1CCC2=CC(=CC=C12)CCN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | Methanesulfonyl chloride (55 mg, 0.48 mmol) was added to a suspension of 3,4-dihydro-1'-[2-(2,3-dihydro-1H-indol-5-yl)ethyl]-6-methanesulfonamido-spiro[(2H)-benzopyran-2,4'-piperidine]-4-one (crude, 84% pure, 217 mg, 0.4 mmol) in pyridine (5 ml). The mixture was stirred for 22 hours, then the solvent was evaporated und... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Sulfonamide.Hydrazine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccc2c(c1)CC[NH]2 | null | C(C)O | null | 22 | CS(=O)(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4c(c3)CCN4)CC1)O2>C(C)O>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4c(c3)CCN4NS(C)(=O)=O)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-279cdd14781f41258a183f976b3f293e | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccccc3)CC1)O2.NO>>CS(=O)(=O)Nc1ccc2c(c1)C(=NO)CC1(CCN(CCc3ccccc3)CC1)O2 | CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC3=CC=CC=C3)O2)=O)C1.Cl.NO.N1CCCCC1>>CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC3=CC=CC=C3)O2)=NO)C1 | O=[C:12]1[c:10]2[c:9]([cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]2)[O:30][C:16]2([CH2:15]1)[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][CH2:29]2.[NH2:13][OH:14]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[N:13][OH:14... | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccccc3)CC1)O2.NO | CS(=O)(=O)Nc1ccc2c(c1)C(=NO)CC1(CCN(CCc3ccccc3)CC1)O2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 19f6766c1065b3ee1b1d06e0931ba638b76f588f0353dfdef89817254c5f9179 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C1CC2(CCN(CCc3ccccc3)CC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[O;D1;H1:9]-[N;H0;D2;+0:8]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7] | null | [] | null | null | null | null | In the manner of Example 427, 3,4-dihydro-6-methane-sulfonamido-1'-(2-phenylethyl)-spiro[(2H)-benzopyran-2,4'-piperidine]-4-one was treated with hydroxylamine hydrochloride to give, after chromatography, the piperidine as a solid, m.p. 95°-99° C.
Conditions: See reaction.notes.procedure_details.
Workup: to give | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | HO- | null | null | null | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccccc3)CC1)O2.NO>>CS(=O)(=O)Nc1ccc2c(c1)C(=NO)CC1(CCN(CCc3ccccc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1deef3ab54144803bab9edf9dbee3418 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2>>CS(=O)(=O)Nc1ccc2c(c1)C(O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | Cl.[BH4-].[Na+].N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C.C(O)([O-])=O.[Na+]>>Cl.N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)O)C=C(C=C2)NS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]4[n:25][o:26][n:27][c:28]4[cH:29]3)[CH2:30][CH2:31]1)[O:32]2>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH:12]([OH:1... | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | CS(=O)(=O)Nc1ccc2c(c1)C(O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | null | null | C(C)(=O)OCC.C(C)O | Reduction | Reduction of ketone to secondary alcohol | 2378f558ed07eb081065e42309a5d6dee8dd455c6fabd59d55c3aaf4c2579434 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#8:5]-[c:6]:[c:7]-1:[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[#8:5]-[c:6]:[c:7]-1:[c:8] | 65 | [{"value": 65.0, "product": "Cl.N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)O)C=C(C=C2)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Sodium borohydride (7.5 mg, 0.2 mmol) was added to a stirred suspension of 3,4-dihydro-1'-[2-(benzofurazan-5-yl)ethyl]-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one [prepared as described in Example 94, Step B] (45.6 mg, 0.1 mmol) in ethanol (2 ml). The mixture was stirred for 16 hours, then poure... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccc2nonc2c1 | null | C(C)(=O)OCC.C(C)O | null | 16 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2>C(C)(=O)OCC.C(C)O>CS(=O)(=O)Nc1ccc2c(c1)C(O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7bc9e01d3d47429ba198b10e7b7a6e3c | CC(=O)Nc1ccc(O)c(C(C)=O)c1.O=C1CCN(CCc2ccc3nonc3c2)CC1>>Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | N1=C2C(=NO1)C=C(C=C2)CCN2CCC(CC2)=O.C(C)(=O)C=1C=C(C=CC1O)NC(C)=O.N1CCCC1.Cl>>NC=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC=4C(=NON4)C3)O2)=O)C1 | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]([OH:28])[c:6]([C:8](=[O:9])[CH3:10])[cH:7]1.O=[C:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]3[n:21][o:22][n:23][c:24]3[cH:25]2)[CH2:26][CH2:27]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][C:11]1([CH2:12][CH2:13][N:14]([CH2:15][CH2:1... | CC(=O)Nc1ccc(O)c(C(C)=O)c1.O=C1CCN(CCc2ccc3nonc3c2)CC1 | Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | null | null | CO.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | ab69a3c6b4f5ad630be9851e126d969c65e261f0d4fc324974ff407cf46a3bf2 | 958ab5dc78f09169eace1c16e7e26b50616ed7dec9cadcb081fdea26fcb12d74 | O=C1CC2(CCN(CCc3ccc4nonc4c3)CC2)Oc2ccccc21 | C-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[OH;D1;+0:6]):[c:7](-[C:8](-[CH3;D1;+0:9])=[O;D1;H0:10]):[c:11]:1.O=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[#7:15]-[C:16]-[C:17]-1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[c:7](:[c:11]:1)-[C:8](=[O;D1;H0:10])-[CH2;D2;+0:9]-[C;H0;D4;+0:12]1(-[C:13]-[C:14]-[#7:15]-[C:16]-[C:17]-1)-... | 77.3 | [{"value": 77.0, "product": "NC=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC=4C(=NON4)C3)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "NC=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC=4C(=NON4)C3)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[2-(Benzofurazan-5-yl)ethyl]-4-piperidinone (0.98 g, 4 mmol), N-(3-acetyl-4-hydroxyphenyl)acetamide (0.77 g, 4 mmol) and pyrrolidine (0.33 ml, 0.28 g, 4 mmol) in methanol (20 ml) were heated under reflux for 3 hours, cooled and the solvent was evaporated under reduced pressure. Water (50 ml) and aqueous sodium hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Secondary amide.Aromatic alcohol | Ketone.Ether.Primary amine | C1CC[NH]CC1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccc2nonc2c1 | HO- | CO.C(C)O | null | null | CC(=O)Nc1ccc(O)c(C(C)=O)c1.O=C1CCN(CCc2ccc3nonc3c2)CC1>CO.C(C)O>Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ea8def37ace8456b89df8f614a449e68 | CCOC(=O)CS(=O)(=O)Cl.CCOC(=O)CS(=O)(=O)Cl.Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2>>CCN(c1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2)S(=O)(=O)OC(C)=O | ClS(=O)(=O)CC(=O)OCC.Cl.ClS(=O)(=O)CC(=O)OCC.NC=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC=4C(=NON4)C3)O2)=O)C1.N1=CC=CC=C1.CN(C)C=O.CN(C)C=O.C(O)([O-])=O.[Na+]>>Cl.C(C)(=O)OS(=O)(=O)N(C=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC=4C(=NON4)C3)O2)=O)C1)CC | O=C(CS(=O)(Cl)=[O:33])O[CH2:2][CH3:1].CCO[C:35]([CH2:36][S:31](Cl)(=[O:32])=[O:34])=[O:37].[NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10](=[O:11])[CH2:12][C:13]1([CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]3[cH:20][cH:21][c:22]4[n:23][o:24][n:25][c:26]4[cH:27]3)[CH2:28][CH2:29]1)[O:30]2>>[CH3:1][CH2:2][N:3]([c:4]... | CCOC(=O)CS(=O)(=O)Cl.CCOC(=O)CS(=O)(=O)Cl.Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | CCN(c1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2)S(=O)(=O)OC(C)=O | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 6c521336b66513ed114349b9427a44b6bcd0e1a1e83f3be5cbc6974400db5145 | 900f8cbd5768d3f2ec159ffc6171a9d01dff10c63e7722241735ef1c3655be09 | O=C1CC2(CCN(CCc3ccc4nonc4c3)CC2)Oc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[S;H0;D4;+0:4](-Cl)(=[O;D1;H0:5])=[O;H0;D1;+0:6].Cl-S(=O)(=[O;H0;D1;+0:7])-C-C(=O)-O-[CH2;D2;+0:8]-[C;D1;H3:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:9]-[CH2;D2;+0:8]-[N;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[S;H0;D4;+0:4](=[O;D1;H0:5])(=[O;H0;D1;+0:7])-[O;H0;D2... | 61 | [{"value": 61.0, "product": "Cl.C(C)(=O)OS(=O)(=O)N(C=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC=4C(=NON4)C3)O2)=O)C1)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Ethyl chlorosulfonylacetate (140 mg, 0.75 mmol) in DMF (1 ml) was added dropwise to a stirred solution of 6-amino-3,4-dihydro-1'-[2-(benzofurazan-5-yl)-ethyl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (189 mg, 0.5 mmol) and pyridine (40 mg, 3 mmol) in DMF (5 ml). The mixture was stirred for 4 hours, then additiona... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine.Sulfonyl halide.Sulfonyl halide | Tertiary amine.Sulfamate | null | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccc2nonc2c1 | HCl | C(C)(=O)OCC | null | 4 | CCOC(=O)CS(=O)(=O)Cl.CCOC(=O)CS(=O)(=O)Cl.Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2>C(C)(=O)OCC>CCN(c1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2)S(=O)(=O)OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-940f3abcfaa547b195ac34ce49c1c054 | COc1ccc(O)c(C(C)=O)c1.O=C1CCN(C(=O)c2ccccc2)CC1>>COc1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 | N1CCCC1.OC1=C(C=C(C=C1)OC)C(C)=O.C(C1=CC=CC=C1)(=O)N1CCC(CC1)=O>>C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:26])[c:7]([C:9](=[O:10])[CH3:11])[cH:8]1.O=[C:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][C:12]1([CH2:13][CH2:14][N:15]([C:16](=[O:17])[c:18]3[cH:... | COc1ccc(O)c(C(C)=O)c1.O=C1CCN(C(=O)c2ccccc2)CC1 | COc1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 | null | null | CO | Heteroatom Alkylation and Arylation | spiro-chromanone | 516e17e36e6da47114ec867780566e28862277ef4db6e563ed68fe6015ca5775 | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[O;D1;H0:9]=[C:8]1-[CH2;D2;+0:7]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-1 | 84.1 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Pyrrolidine (8.35 ml, 7.11 g, 0.1 mol) was added to a suspension of 2'-hydroxy-5'-methoxyacetophenone (16.62 g, 0.1 mol) in methanol (100 ml). The mixture was stirred for 10 minutes, then 1-benzoyl-4-piperidone (20.32 g, 0.1 mol) was added and the mixture was heated under reflux for 7 hr. The mixture was cooled and the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CC[NH]CC1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | HO- | CO | null | 0.166667 | COc1ccc(O)c(C(C)=O)c1.O=C1CCN(C(=O)c2ccccc2)CC1>CO>COc1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-69622abc75e54c65b44077afe8a491e3 | COc1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2>>COc1ccc2c(c1)CCC1(CCN(C(=O)c3ccccc3)CC1)O2 | C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)OC.[BH4-].[Na+].C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(CC2)C=C(C=C1)OC | O=[C:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[O:25][C:11]2([CH2:10]1)[CH2:12][CH2:13][N:14]([C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:23][CH2:24]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11]1([CH2:12][CH2:13][N:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:... | COc1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 | COc1ccc2c(c1)CCC1(CCN(C(=O)c3ccccc3)CC1)O2 | null | [Pd] | null | Reduction | OtherReaction | 277703de3ea638a0f32ca6dad92b6f57c2d7ef0794d4dd6fb83f66886a1a8618 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | O=C(c1ccccc1)N1CCC2(CCc3ccccc3O2)CC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7]>>[c:7]:[c:6]1:[c:5]-[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-1 | 54 | [{"value": 54.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(CC2)C=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedures as described in Example 435, 1'-benzoyl-3,4-dihydro-6-methoxyspiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one was reduced with sodium borohydride, dehydrated with p-toluenesulfonic acid and hydrogenated with palladium on carbon (5%) under hydrogen (50 psi) to give the piperidine as a foam (54%).
... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | Other | [Pd] | null | null | COc1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2>[Pd]>COc1ccc2c(c1)CCC1(CCN(C(=O)c3ccccc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-138eaf5f60e2430abbc03f6cbf08f276 | CS(=O)(=O)Nc1ccc2c(c1)CCC1(CCN(C(=O)c3ccccc3)CC1)O2>>CS(=O)(=O)Nc1ccc2c(c1)CCC1(CCNCC1)O2 | C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(CC2)C=C(C=C1)NS(=O)(=O)C.Cl>>Cl.CS(=O)(=O)NC=1C=CC2=C(CCC3(CCNCC3)O2)C1 | O=C(c1ccccc1)[N:17]1[CH2:16][CH2:15][C:14]2([CH2:13][CH2:12][c:10]3[c:9]([cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]3)[O:20]2)[CH2:19][CH2:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][CH2:13][C:14]1([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1)[O:20]2 | CS(=O)(=O)Nc1ccc2c(c1)CCC1(CCN(C(=O)c3ccccc3)CC1)O2 | CS(=O)(=O)Nc1ccc2c(c1)CCC1(CCNCC1)O2 | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | 187457a5bb16742685b958a2fef8efedd4134eccad2aa3d422df824de57b008d | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1ccc2c(c1)CCC1(CCNCC1)O2 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 83 | [{"value": 83.0, "product": "Cl.CS(=O)(=O)NC=1C=CC2=C(CCC3(CCNCC3)O2)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1'-Benzoyl-3,4-dihydro-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine] (5.44 g, 13.6 mmol) was dissolved in methanol (70 ml) and aqueous HCl (6N, 105 ml) was added. The mixture was heated under reflux for 24 hr, then the volume was reduced to 50 ml by distillation. Ethanol (200 ml) was added and the volum... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CCNCC1)O2 | c1ccc2c(c1)CCC1(CCNCC1)O2 | HO- | CO | null | null | CS(=O)(=O)Nc1ccc2c(c1)CCC1(CCN(C(=O)c3ccccc3)CC1)O2>CO>CS(=O)(=O)Nc1ccc2c(c1)CCC1(CCNCC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4ffa9ca4431d46dc85f632b388fbb1f5 | CC(=O)c1cc2c(cc1O)OCO2.O=C1CCN(CCc2ccccc2)CC1>>O=C1CC2(CCN(CCc3ccccc3)CC2)Oc2cc3c(cc21)OCO3 | Cl.N1CCCC1.OC=1C(=CC2=C(OCO2)C1)C(C)=O.C1(=CC=CC=C1)CCN1CCC(CC1)=O>>Cl.C1(=CC=CC=C1)CCN1CCC2(CC1)OC1=C(C(C2)=O)C=C2C(=C1)OCO2 | [O:2]=[C:3]([CH3:4])[c:25]1[c:20]([OH:19])[cH:21][c:22]2[c:23]([cH:24]1)[O:26][CH2:27][O:28]2.O=[C:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[O:2]=[C:3]1[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17][CH2:18... | CC(=O)c1cc2c(cc1O)OCO2.O=C1CCN(CCc2ccccc2)CC1 | O=C1CC2(CCN(CCc3ccccc3)CC2)Oc2cc3c(cc21)OCO3 | null | null | CO.C(C)O | Heteroatom Alkylation and Arylation | spiro-chromanone | f920f0c270aab251ad4336158c49affd8de93e351095a46b6ad9497f3ea5b543 | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CC2(CCN(CCc3ccccc3)CC2)Oc2cc3c(cc21)OCO3 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[O;D1;H0:9]=[C:8]1-[CH2;D2;+0:7]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-1 | 38 | [{"value": 38.0, "product": "Cl.C1(=CC=CC=C1)CCN1CCC2(CC1)OC1=C(C(C2)=O)C=C2C(=C1)OCO2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Pyrrolidine (83 ml, 71 mg, 1 mmol) was added to a mixture of 1-(6-hydroxy-1,3-benzodioxol-5-yl)-ethanone [prepared as described by K. Fukui and M. Nakayama, Bull. Chem: Soc. Jap., 1963, 37, 300.] (180 mg, 1 mmol) in methanol (1 ml). The mixture was stirred for 10 minutes, then 1-(2-phenylethyl)-4-piperidinone (203 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CC[NH]CC1 | c1c2c(cc3c1OCO3)OC1(CC[NH]CC1)CC2 | c1ccccc1.c1c2c(cc3c1OCO3)OC1(CC[NH]CC1)CC2 | HO- | CO.C(C)O | null | 0.166667 | CC(=O)c1cc2c(cc1O)OCO2.O=C1CCN(CCc2ccccc2)CC1>CO.C(C)O>O=C1CC2(CCN(CCc3ccccc3)CC2)Oc2cc3c(cc21)OCO3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-01704057fb1b46e68a95066687aba699 | Nc1cc2c(cc1[N+](=O)[O-])C(=O)CC1(CCN(CCc3ccccc3)CC1)O2>>Nc1cc2c(cc1N)C(=O)CC1(CCN(CCc3ccccc3)CC1)O2 | NC1=CC2=C(C(CC3(CCN(CC3)CCC3=CC=CC=C3)O2)=O)C=C1[N+](=O)[O-].O1C(C=CC=C1)=O>>NC=1C(=CC2=C(C(CC3(CCN(CC3)CCC3=CC=CC=C3)O2)=O)C1)N | O=[N+:8]([O-])[c:7]1[c:2]([NH2:1])[cH:3][c:4]2[c:5]([cH:6]1)[C:9](=[O:10])[CH2:11][C:12]1([CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24][CH2:25]1)[O:26]2>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[NH2:8])[C:9](=[O:10])[CH2:11][C:12]1([CH2:13][CH2:14][N:15]([CH2:16][CH2:17]... | Nc1cc2c(cc1[N+](=O)[O-])C(=O)CC1(CCN(CCc3ccccc3)CC1)O2 | Nc1cc2c(cc1N)C(=O)CC1(CCN(CCc3ccccc3)CC1)O2 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1CC2(CCN(CCc3ccccc3)CC2)Oc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In the manner of Example 462, 7-amino-3,4-dihydro-6-nitro-1'-(2-phenylethyl)-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (1.22 g, 3.2 mmol) was reduced to give, after chromatography, the pyranone as a yellow foam (790 mg, 70%).
Conditions: See reaction.notes.procedure_details.
Workup: to give | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | Other | null | null | null | Nc1cc2c(cc1[N+](=O)[O-])C(=O)CC1(CCN(CCc3ccccc3)CC1)O2>>Nc1cc2c(cc1N)C(=O)CC1(CCN(CCc3ccccc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e0c45232d4d140a19e8b3300f46045d5 | CC(=O)NN1CCC2(CC1)Oc1ccc(S(C)(=O)=O)cc1C(=O)C2C>>CC1C(=O)c2cc(S(C)(=O)=O)ccc2OC12CCNCC2 | C(C)(=O)NN1CCC2(CC1)OC1=C(C(C2C)=O)C=C(C=C1)S(=O)(=O)C.Cl>>Cl.CC1C(C2=C(OC13CCNCC3)C=CC(=C2)S(=O)(=O)C)=O | CC(=O)N[N:19]1[CH2:18][CH2:17][C:16]2([CH:2]([CH3:1])[C:3](=[O:4])[c:5]3[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]3[O:15]2)[CH2:21][CH2:20]1>>[CH3:1][CH:2]1[C:3](=[O:4])[c:5]2[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]2[O:15][C:16]12[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2 | CC(=O)NN1CCC2(CC1)Oc1ccc(S(C)(=O)=O)cc1C(=O)C2C | CC1C(=O)c2cc(S(C)(=O)=O)ccc2OC12CCNCC2 | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | bb3f98cf00075ccee07fc64c544d2a263c56396bce3bfe8a8aaa859e51e79df8 | aa08e79ce1ff03d86f650db890fd3d916ec17d973a6ec07d53d47787a887d3a3 | O=C1CC2(CCNCC2)Oc2ccccc21 | C-C(=O)-N-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | The product of Step B (0.5 g) in CH3OH (15 mL) and 6N HCl (15 mL) was heated at reflux for 10 hours. The reaction was concentrated to dryness. and the residue flushed with ethanol (4 times) and then toluene to yield 0.5 g of the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: at reflux for 10 ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Secondary amine | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CCNCC1)O2 | c1ccc2c(c1)CCC1(CCNCC1)O2 | HO- | CO | null | null | CC(=O)NN1CCC2(CC1)Oc1ccc(S(C)(=O)=O)cc1C(=O)C2C>CO>CC1C(=O)c2cc(S(C)(=O)=O)ccc2OC12CCNCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-533498180d604b9bb47605586215ea6f | CC(=O)N1CCC(=O)CC1.CC(=O)c1cc(O)ccc1O>>CC(=O)N1CCC2(CC1)CC(=O)c1c(O)cccc1O2 | OC1=C(C=C(C=C1)O)C(C)=O.C(C)(=O)N1CCC(CC1)=O>>C(C)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C(=CC=C1)O | O=[C:7]1[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:9][CH2:8]1.[CH3:10][C:11](=[O:12])[c:19]1[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]1[OH:20]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[CH2:10][C:11](=[O:12])[c:13]1[c:14]([OH:15])[cH:16][cH:17][cH:18][c:19]1[O:20]2 | CC(=O)N1CCC(=O)CC1.CC(=O)c1cc(O)ccc1O | CC(=O)N1CCC2(CC1)CC(=O)c1c(O)cccc1O2 | null | null | CCOC(=O)C.CCCCCC | C-C Coupling | OtherReaction | c7faec650ebd34dfa4da7f20c93f00598dc732a71884933584b95f7ad1789470 | ffc8359b37fcff4060656764c3df7f3f28facd464bfb7d1296cff4ae3dfce590 | O=C1CC2(CCNCC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c:12](-[O;D1;H1:13]):[c:14]:[c:15]:[c;H0;D3;+0:16]:1-[OH;D1;+0:17]>>[O;D1;H0:9]=[C;H0;D3;+0:8]1-[CH2;D2;+0:7]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[O;H0;D2;+0:17]-[c;H0;D3;+0:10]2:... | null | [] | null | null | null | null | 2',5'-Dihydroxyacetophenone and 1-acetyl-4-piperidone were condensed according to the method of Example 434 to give the ketone as a yellow solid, m.p. 114°-116° C. (from EtOAc/hexane).
Conditions: See reaction.notes.procedure_details.
Workup: condensed | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CC[NH]CC1.c1ccccc1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HO- | CCOC(=O)C.CCCCCC | null | null | CC(=O)N1CCC(=O)CC1.CC(=O)c1cc(O)ccc1O>CCOC(=O)C.CCCCCC>CC(=O)N1CCC2(CC1)CC(=O)c1c(O)cccc1O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8c23b8e3f3294e6386da0a6c88fc0ae2 | CC(=O)N1CCC2(CC1)CC(=O)c1c(ccc([N+](=O)[O-])c1O)O2.CI>>COc1c([N+](=O)[O-])ccc2c1C(=O)CC1(CCN(C(C)=O)CC1)O2 | CI.C(C)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C(=C(C=C1)[N+](=O)[O-])O.C([O-])([O-])=O.[K+].[K+].CI>>C(C)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C(=C(C=C1)[N+](=O)[O-])OC | [OH:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][N:18]([C:19]([CH3:20])=[O:21])[CH2:22][CH2:23]1)[O:24]2.I[CH3:1]>>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][N:18]([C:19]([CH3:20])... | CC(=O)N1CCC2(CC1)CC(=O)c1c(ccc([N+](=O)[O-])c1O)O2.CI | COc1c([N+](=O)[O-])ccc2c1C(=O)CC1(CCN(C(C)=O)CC1)O2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C1CC2(CCNCC2)Oc2ccccc21 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[CH3;D1;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-[C:3]=[O;D1;H0:2] | 101.7 | [{"value": 101.7, "product": "C(C)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C(=C(C=C1)[N+](=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of 1'-acetyl-3,4-dihydro-5-hydroxy-6-nitro-spiro[2H-1-benzopyran-2,4'-piperidine]-4-one (3.84 g, 12 mmol), potassium carbonate (1.66 g, 12 mmol) and methyl iodide (3.74 ml, 8.51 g, 60 mmol) in DMF (30 ml) was stirred in a sealed vessel at room temperature for 3 days, adding further portions of methyl iodide (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HI | CN(C)C=O | null | 72 | CC(=O)N1CCC2(CC1)CC(=O)c1c(ccc([N+](=O)[O-])c1O)O2.CI>CN(C)C=O>COc1c([N+](=O)[O-])ccc2c1C(=O)CC1(CCN(C(C)=O)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-36f4e07ece4345459e811bf56f018f8b | CC(=O)c1cc(S(C)(=O)=O)ccc1O.O=C1CCN(C(=O)c2ccccc2)CC1>>CS(=O)(=O)c1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 | OC1=C(C=C(C=C1)S(=O)(=O)C)C(C)=O.C(C1=CC=CC=C1)(=O)N1CCC(CC1)=O>>C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)S(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:28])[c:9]([C:11](=[O:12])[CH3:13])[cH:10]1.O=[C:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[CH2:13][C:14]1([CH2:15][CH2:... | CC(=O)c1cc(S(C)(=O)=O)ccc1O.O=C1CCN(C(=O)c2ccccc2)CC1 | CS(=O)(=O)c1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 | null | null | null | Heteroatom Alkylation and Arylation | spiro-chromanone | 516e17e36e6da47114ec867780566e28862277ef4db6e563ed68fe6015ca5775 | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[O;D1;H0:9]=[C:8]1-[CH2;D2;+0:7]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-1 | null | [] | null | null | null | null | 2'-Hydroxy-5'-methanesulfonylacetophenone and 1-benzoyl-4-piperidone were condensed according to the method of Example 434 to give the ketone as a white solid, m.p. 155°-157° C.
Conditions: See reaction.notes.procedure_details.
Workup: condensed | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CC[NH]CC1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | HO- | null | null | null | CC(=O)c1cc(S(C)(=O)=O)ccc1O.O=C1CCN(C(=O)c2ccccc2)CC1>>CS(=O)(=O)c1ccc2c(c1)C(=O)CC1(CCN(C(=O)c3ccccc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-67abe4c548034256ae6714c550d7c0b3 | CC(=O)N1CCC(=O)CC1.CC(=O)c1cc(S(C)(=O)=O)ccc1O>>CC(=O)N1CCC2(CC1)CC(=O)c1cc(S(C)(=O)=O)ccc1O2 | OC1=C(C=C(C=C1)S(=O)(=O)C)C(C)=O.C(C)(=O)N1CCC(CC1)=O>>C(C)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)S(=O)(=O)C | O=[C:7]1[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:9][CH2:8]1.[CH3:10][C:11](=[O:12])[c:13]1[cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][cH:21][c:22]1[OH:23]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[CH2:10][C:11](=[O:12])[c:13]1[cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][... | CC(=O)N1CCC(=O)CC1.CC(=O)c1cc(S(C)(=O)=O)ccc1O | CC(=O)N1CCC2(CC1)CC(=O)c1cc(S(C)(=O)=O)ccc1O2 | null | null | null | Heteroatom Alkylation and Arylation | spiro-chromanone | 516e17e36e6da47114ec867780566e28862277ef4db6e563ed68fe6015ca5775 | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CC2(CCNCC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[O;D1;H0:9]=[C:8]1-[CH2;D2;+0:7]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-1 | null | [] | null | null | null | null | 2'-Hydroxy-5'-methanesulfonylacetophenone and 1-acetyl-4-piperidone were condensed according to the method of Example 434 to give the ketone as a white solid, m.p. 105°-110° C.
Conditions: See reaction.notes.procedure_details.
Workup: condensed | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CC[NH]CC1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HO- | null | null | null | CC(=O)N1CCC(=O)CC1.CC(=O)c1cc(S(C)(=O)=O)ccc1O>>CC(=O)N1CCC2(CC1)CC(=O)c1cc(S(C)(=O)=O)ccc1O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-da0bffbab7c2487da8987ed3d4c2c57a | COc1cc(C(C#N)CCN(C)C)cc(OC)c1OC.[OH-]>>COc1cc(C(CCN(C)C)C(N)=O)cc(OC)c1OC | CN(CCC(C#N)C1=CC(=C(C(=C1)OC)OC)OC)C.[OH-].[K+].C(C)(=O)OCC.Cl>>CN(CCC(C(=O)N)C1=CC(=C(C(=C1)OC)OC)OC)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH2:7][CH2:8][N:9]([CH3:10])[CH3:11])[C:12]#[N:13])[cH:15][c:16]([O:17][CH3:18])[c:19]1[O:20][CH3:21].[OH-:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH2:7][CH2:8][N:9]([CH3:10])[CH3:11])[C:12]([NH2:13])=[O:14])[cH:15][c:16]([O:17][CH3:18])[c:19]1[O:20][CH3:21] | COc1cc(C(C#N)CCN(C)C)cc(OC)c1OC.[OH-] | COc1cc(C(CCN(C)C)C(N)=O)cc(OC)c1OC | null | null | CC(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccccc1 | [C:1]-[C:2](-[c:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[OH-;D0:6]>>[C:1]-[C:2](-[c:3])-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[O;H0;D1;+0:6] | null | [] | null | null | null | null | In 8 ml of 2-methyl-2-propanol was dissolved 0.84 g of 4-dimethylamino-2-(3,4,5-trimethoxyphenyl)butyronitrile, followed by addition of 1.0 g of ground potassium hydroxide. The mixture was refluxed for 1 hour. After cooling the reaction mixture, the insoluble matters were filtered off and the filtrate was concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1 | null | CC(C)(C)O | null | null | COc1cc(C(C#N)CCN(C)C)cc(OC)c1OC.[OH-]>CC(C)(C)O>COc1cc(C(CCN(C)C)C(N)=O)cc(OC)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-96d28e19a0004c299a71babf79972310 | Cl>>Cl | CN(CCN(C(=O)N)C1=CC(=C(C(=C1)OC)OC)OC)C.Cl.O1CCOCC1>>Cl.CN(CCN(C(=O)N)C1=CC(=C(C(=C1)OC)OC)OC)C | [ClH:22]>>[ClH:22] | Cl | Cl | null | null | C(C)OCC.C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | To a solution of 220 mg of 1-(2-dimethylaminoethyl)-1-(3,4,5-trimethoxyphenyl)urea in a mixture of ethanol (3 ml) and diethyl ether (15 ml) was added 4N-HCl-dioxane dropwise with stirring. The resulting crystals were collected by filtration and dried under reduced pressure to provide 230 mg of 1-(2-dimethylaminoethyl)-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)OCC.C(C)O | null | null | Cl>C(C)OCC.C(C)O>Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1c84086202784fc89c92c1c5f9566eb6 | CC1CO1.CN(C)CCNCCN(C)C>>CC(O)CN(CCN(C)C)CCN(C)C | CN(CCNCCN(C)C)C.C1C(C)O1>>CN(CCN(CCN(C)C)CC(C)O)C | [CH3:1][CH:2]1[O:3][CH2:4]1.[NH:5]([CH2:6][CH2:7][N:8]([CH3:9])[CH3:10])[CH2:11][CH2:12][N:13]([CH3:14])[CH3:15]>>[CH3:1][CH:2]([OH:3])[CH2:4][N:5]([CH2:6][CH2:7][N:8]([CH3:9])[CH3:10])[CH2:11][CH2:12][N:13]([CH3:14])[CH3:15] | CC1CO1.CN(C)CCNCCN(C)C | CC(O)CN(CCN(C)C)CCN(C)C | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | null | [C;D1;H3:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:3]-[C:2](-[C;D1;H3:1])-[OH;D1;+0:4] | null | [] | 120 | CELSIUS | 22 | HOUR | N,N,N",N"-Tetramethyldiethylenetriamine (TMDETA, 24.96 g, 157.2 mmole) and propylene oxide (PO, 9.1 g, 157.0 mmole) were charged to a 50 mL autoclave. The reactor was sealed, the contained air was replaced with nitrogen, the reactor was pressured to 100 psi (689 kPa) with nitrogen, and the contents were heated to 120° ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | null | null | null | 120 | 22 | CC1CO1.CN(C)CCNCCN(C)C>>CC(O)CN(CCN(C)C)CCN(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a65d0fc87e374b819e92f28178044fe3 | COc1ccccc1F.O=C(Cl)Cc1ccccc1>>COc1ccc(C(=O)Cc2ccccc2)cc1F | C1(=CC=CC=C1)CC(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-].FC1=C(C=CC=C1)OC>>FC=1C=C(C=CC1OC)C(CC1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:16][c:17]1[F:18].Cl[C:7](=[O:8])[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][c:17]1[F:18] | COc1ccccc1F.O=C(Cl)Cc1ccccc1 | COc1ccc(C(=O)Cc2ccccc2)cc1F | null | null | C(Cl)(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | 0 | CELSIUS | 1 | HOUR | In a 500 mL, 3-neck round-bottom flask, equipped with a pressure equalizing dropping funnel, thermometer, gas inlet tube and provisions for magnetic stirring, a suspension of aluminum chloride (9.4 g, 70.5 mmol) in a solution of 2-fluoroanisole (6.6 mL, 58.8 mmol) and anhydrous chloroform (200 mL) was cooled to 0° C. u... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | 0 | 1 | COc1ccccc1F.O=C(Cl)Cc1ccccc1>C(Cl)(Cl)Cl>COc1ccc(C(=O)Cc2ccccc2)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bed66c73f44b4b089ca7e6cc6beaf44c | COc1ccc(C(=O)Cc2ccccc2)cc1F.NO>>COc1ccc(C(Cc2ccccc2)=NO)cc1F | O.Cl.NO.[OH-].[K+].FC=1C=C(C=CC1OC)C(CC1=CC=CC=C1)=O>>FC=1C=C(C=CC1OC)C(CC1=CC=CC=C1)=NO | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:18]([F:19])[cH:17]1)[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[NH2:15][OH:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)=[N:15][OH:16])[cH:17][c:18]1[F:19] | COc1ccc(C(=O)Cc2ccccc2)cc1F.NO | COc1ccc(C(Cc2ccccc2)=NO)cc1F | null | null | C1(=CC=CC=C1)C.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(Cc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[O;D1;H1:8]-[N;H0;D2;+0:7]=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Hydroxylamine hydrochloride (3.7 g, 53.2 mmol) and potassium hydroxide (2.98 g, 53.2 mmol) were suspended in absolute ethanol (25 mL) and vigorously stirred in a 250-mL round-bottom flask equipped with a magnetic stirring bar under a dry nitrogen blanket for 30 minutes. To this, a suspension of 1-(3-fluoro-4-methoxyphe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.C(C)O | null | null | COc1ccc(C(=O)Cc2ccccc2)cc1F.NO>C1(=CC=CC=C1)C.C(C)O>COc1ccc(C(Cc2ccccc2)=NO)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-98a359504ad54ef6acbe8114391b9bf1 | COc1ccc(C(Cc2ccccc2)=NO)cc1F.O=C1CCC(=O)O1>>COc1ccc(-c2noc(C(C)C(=O)O)c2-c2ccccc2)cc1F | S(O)(O)(=O)=O.FC=1C=C(C=CC1OC)C(CC1=CC=CC=C1)=NO.C(CCC)[Li].C1(CCC(=O)O1)=O>>FC=1C=C(C=CC1OC)C1=NOC(=C1C1=CC=CC=C1)C(C(=O)O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[N:8][OH:9])[CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][c:24]1[F:25].O=[C:10]1[CH2:12][CH2:11][C:13](=[O:14])[O:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]([CH3:12])[C:13](=[O:14])[OH:15])[c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21]... | COc1ccc(C(Cc2ccccc2)=NO)cc1F.O=C1CCC(=O)O1 | COc1ccc(-c2noc(C(C)C(=O)O)c2-c2ccccc2)cc1F | null | null | O.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | a73dd3aece077ba6586aea3fa2bb8eabaa0c312b95d4966e87e48a13f37aca8d | e031ca3b0905cab57446043f3b283894164797b30d6c5dfd9e1fe2bcd3c1af9c | c1ccc(-c2conc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.[OH;D1;+0:7]-[N;H0;D2;+0:8]=[C;H0;D3;+0:9](-[CH2;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15])-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[CH3;D1;+0:2]-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[c;H0;D3;+0:1]1:[o;H0;... | null | [] | -20 | CELSIUS | 1 | HOUR | A dry, 250 mL 3-neck round-bottom flask, equipped with a thermometer, magnetic stirring bar, reflux condenser and rubber septum was charged with 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one oxime from Step 2 (2.00 g, 7.71 mmol) and anhydrous THF (80 mL) under a nitrogen blanket. The solution was cooled to -20° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Oxime | Carboxylic acid | C1CCOC1 | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccccc1 | HO- | O.C1CCOC1 | -20 | 1 | COc1ccc(C(Cc2ccccc2)=NO)cc1F.O=C1CCC(=O)O1>O.C1CCOC1>COc1ccc(-c2noc(C(C)C(=O)O)c2-c2ccccc2)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b3d329596859467ba60b3b11d14e4b7b | CC(C(=O)O)c1onc(-c2ccccc2)c1-c1ccccc1.CCO.N.O=S(=O)(O)Cl>>CCOC(=O)C(C)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 | ClS(=O)(=O)O.C1(=CC=CC=C1)C1=NOC(=C1C1=CC=CC=C1)C(C(=O)O)C.S(O)(O)(=O)=O.C(C)O.N>>NS(=O)(=O)C1=CC=C(C=C1)C=1C(=NOC1C(C(=O)OCC)C)C1=CC=CC=C1 | O[C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[o:9][n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1-[c:19]1[cH:20][cH:21][cH:22][cH:27][cH:28]1.[CH3:1][CH2:2][OH:3].[NH3:24].O=[S:23](Cl)(=[O:25])[OH:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[o:9][n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH... | CC(C(=O)O)c1onc(-c2ccccc2)c1-c1ccccc1.CCO.N.O=S(=O)(O)Cl | CCOC(=O)C(C)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 | null | null | null | Protection | OtherReaction | 2acf0430d2fb9cf866e357c6e0829a52dce85a6a97132df1ea344acd5b1587ba | b4985a30efea66812d0bb5c9181f8cfb3bf29719f9ac7f3116824efdfd7a870a | c1ccc(-c2conc2-c2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](=O)(=[O;D1;H0:2])-[OH;D1;+0:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6](-[C;D1;H3:7])-[c:8]:[#8;a:9]:[#7;a:10].[c:11]:[c:12]:[cH;D2;+0:13]:[c:14]:[c:15].[C;D1;H3:16]-[C:17]-[OH;D1;+0:18].[NH3;D0;+0:19]>>[#7;a:10]:[#8;a:9]:[c:8]-[C:6](-[C;D1;H3:7])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:18]-[C:17]-[C;D1;... | 60 | [{"value": 60.0, "product": "NS(=O)(=O)C1=CC=C(C=C1)C=1C(=NOC1C(C(=O)OCC)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of [3,4-diphenylisoxazol-5-yl]propanoic acid was treated with ethanol in the presence of a catalytic amount of sulfuric acid to prepare the corresponding ethyl ester which was immediately treated with chlorosulfonic acid followed by ammonia according to the procedure from Example 2, Step 4. The crude sulfona... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Sulfonamide.Ester | c1ccccc1 | c1ccccc1 | c1cnoc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C(=O)O)c1onc(-c2ccccc2)c1-c1ccccc1.CCO.N.O=S(=O)(O)Cl>>CCOC(=O)C(C)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e85dfcfdecae461d93dac45081928234 | CCOC(=O)C(C)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1>>CC(C(=O)O)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 | ClCCl.NS(=O)(=O)C1=CC=C(C=C1)C=1C(=NOC1C(C(=O)OCC)C)C1=CC=CC=C1.[OH-].[Na+].O>>NS(=O)(=O)C1=CC=C(C=C1)C=1C(=NOC1C(C(=O)O)C)C1=CC=CC=C1 | CC[O:5][C:3]([CH:2]([CH3:1])[c:6]1[o:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]1-[c:17]1[cH:18][cH:19][c:20]([S:21]([NH2:22])(=[O:23])=[O:24])[cH:25][cH:26]1)=[O:4]>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[o:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]1-[c:17]1[cH:18][cH:19][c... | CCOC(=O)C(C)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 | CC(C(=O)O)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 | null | null | O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2conc2-c2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 73.2 | [{"value": 73.0, "product": "NS(=O)(=O)C1=CC=C(C=C1)C=1C(=NOC1C(C(=O)O)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "NS(=O)(=O)C1=CC=C(C=C1)C=1C(=NOC1C(C(=O)O)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Ethyl [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]propanoate from Step 2 (198 mg, 0.495 mmol) and aqueous sodium hydroxide (10%, 0.30 mL) were dissolved in dioxane (15 mL). The solution was heated to reflux and held for 16 hours. Upon cooling to room temperature, water (20 mL) was added, and the solution was ext... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnoc1.c1ccccc1.c1ccccc1 | Other | O1CCOCC1 | null | 16 | CCOC(=O)C(C)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1>O1CCOCC1>CC(C(=O)O)c1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bc64539ec5d3425eb46cfe4ea0cfac4d | CC(=O)OC(C)=O.COc1ccc(C(Cc2ccccc2)=NO)cc1F>>COc1ccc(C2=NOC(C)(O)C2c2ccccc2)cc1F | Cl.C(CCC)[Li].FC=1C=C(C=CC1OC)C(CC1=CC=CC=C1)=NO.C(C)(=O)OC(C)=O>>FC=1C=C(C=CC1OC)C1=NOC(C1C1=CC=CC=C1)(C)O | CC(=O)O[C:10]([CH3:11])=[O:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[N:8][OH:9])[CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[F:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][O:9][C:10]([CH3:11])([OH:12])[CH:13]2[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[F:22] | CC(=O)OC(C)=O.COc1ccc(C(Cc2ccccc2)=NO)cc1F | COc1ccc(C2=NOC(C)(O)C2c2ccccc2)cc1F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8dcc1140e1a2a1a7a1cc4280225d32d27843734e2b9a7934f1c7f381fb482949 | 29f8bded40fe350afea3bc544ca1772ed28ec13d06c729ac3e84f1b19f2cb803 | c1ccc(C2=NOCC2c2ccccc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H0;D1;+0:3].[OH;D1;+0:4]-[#7:5]=[C:6](-[c:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[OH;D1;+0:3])-[O;H0;D2;+0:4]-[#7:5]=[C:6](-[c:7])-[CH;D3;+0:8]-1-[c:9](:[c:10]):[c:11] | 33.9 | [{"value": 33.9, "product": "FC=1C=C(C=CC1OC)C1=NOC(C1C1=CC=CC=C1)(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 1 | HOUR | A dry, 250 mL 3-neck round-bottom flask, equipped with a thermometer, magnetic stirring bar, reflux condenser and rubber septum was charged with 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one oxime (from Example 2, Step 2) (2.50 g, 9.64 mmol) and anhydrous THF (100 mL) under a nitrogen blanket. The solution was cool... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Oxime | Tertiary alcohol | null | C1=NOCC1 | c1ccccc1.C1=NOCC1.c1ccccc1 | HO- | C1CCOC1 | -20 | 1 | CC(=O)OC(C)=O.COc1ccc(C(Cc2ccccc2)=NO)cc1F>C1CCOC1>COc1ccc(C2=NOC(C)(O)C2c2ccccc2)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3e70e1681d8b42a7ba9dcb842baf38bc | CC(=O)OC(C)=O.CSc1ccc(CC(=NO)c2ccccc2)cc1>>CSc1ccc(-c2c(-c3ccccc3)noc2C)cc1 | C1(=CC=CC=C1)C(CC1=CC=C(C=C1)SC)=NO.C(C)(=O)OC(C)=O>>CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)SC | CC(=O)O[C:17](=O)[CH3:18].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)=[N:15][OH:16])[cH:19][cH:20]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[n:15][o:16][c:17]2[CH3:18])[cH:19][cH:20]1 | CC(=O)OC(C)=O.CSc1ccc(CC(=NO)c2ccccc2)cc1 | CSc1ccc(-c2c(-c3ccccc3)noc2C)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6e90b2cff34a94737f5a3ac6e9191c7ff578ee46b13d91424e83f41eb68e817c | fe3e6762590177c290f284bf0a605cc085e349c79dc32d2c64aa22c2fd6d1a4d | c1ccc(-c2conc2-c2ccccc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[OH;D1;+0:3]-[N;H0;D2;+0:4]=[C;H0;D3;+0:5](-[CH2;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[o;H0;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c;H0;D3;... | 48 | [{"value": 48.0, "product": "CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Methyl-4-[4-(methylthio)phenyl]-3-phenylisoxazole was prepared in 48% yield from the reaction of 1-phenyl-2-[4-(methylthio)phenyl]-ethan-1-one oxime (Step 2) and acetic anhydride according to the procedure outlined in Example 4, Step 1: Mass Spectrum: MH+=282. High resolution mass spectrum Calc'd. for C17H15NOS: 281.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Oxime | null | null | c1cnoc1 | c1ccccc1.c1ccccc1.c1cnoc1 | HO- | null | null | null | CC(=O)OC(C)=O.CSc1ccc(CC(=NO)c2ccccc2)cc1>>CSc1ccc(-c2c(-c3ccccc3)noc2C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c7186848cae949309298fd0992bb7fbd | CSc1ccc(-c2c(-c3ccccc3)noc2C)cc1>>Cc1onc(-c2ccccc2)c1-c1ccc(S(C)(=O)=O)cc1 | O.OOS(=O)[O-].[K+].O.CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)SC.CO>>CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)C | [CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]1-[c:13]1[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:21][cH:22]1>>[CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]1-[c:13]1[cH:14][cH:15][c:16]([S:17]([CH3:18])(=[O:19])=[O:20])[cH:21][cH:22]1 | CSc1ccc(-c2c(-c3ccccc3)noc2C)cc1 | Cc1onc(-c2ccccc2)c1-c1ccc(S(C)(=O)=O)cc1 | null | null | null | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(-c2conc2-c2ccccc2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:3](:[c:4]):[c:5] | 29 | [{"value": 29.0, "product": "CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5-Methyl-4-[4-(methylthio)phenyl]-3-phenylisoxazole from Step 3 (100 mg, 0.355 mmol) was dissolved in methanol (20 mL). Oxone® (0.765 g, 1.24 mmol) and water (2 mL) were added, and the suspension was stirred at room temperature for 2 hours. Water was added (30 mL) and the resulting suspension was cooled to 0° C. and he... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cnoc1.c1ccccc1.c1ccccc1 | null | null | null | 2 | CSc1ccc(-c2c(-c3ccccc3)noc2C)cc1>>Cc1onc(-c2ccccc2)c1-c1ccc(S(C)(=O)=O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-68b1442a02a241839e065e5997471261 | COc1ccccc1F.CSc1ccc(CC(=O)Cl)cc1>>COc1ccc(C(=O)Cc2ccc(SC)cc2)cc1F | FC1=C(C=CC=C1)OC.CSC1=CC=C(C=C1)CC(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>FC=1C=C(C=CC1OC)C(CC1=CC=C(C=C1)SC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:18][c:19]1[F:20].Cl[C:7](=[O:8])[CH2:9][c:10]1[cH:11][cH:12][c:13]([S:14][CH3:15])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][c:13]([S:14][CH3:15])[cH:16][cH:17]2)[cH:18][c:19]1[F:20] | COc1ccccc1F.CSc1ccc(CC(=O)Cl)cc1 | COc1ccc(C(=O)Cc2ccc(SC)cc2)cc1F | null | null | null | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | 1-(3-Fluoro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one was prepared by Friedel Crafts acylation of 2-fluoroanisole with 4-(methylthio)phenylacetyl chloride in the presence of aluminum chloride: 1H NMR (CDCl3 /300 MHz) δ 7.80-7.70 (m, 2H), 7.24-7.15 (m, 4H), 6.98 (t, J=8.26 Hz), 4.17 (s, 2H), 3.95 (s, 3H), 2.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1F.CSc1ccc(CC(=O)Cl)cc1>>COc1ccc(C(=O)Cc2ccc(SC)cc2)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-979aef270da64f279b75cd871426c7dd | CC(=O)OC(C)=O.COc1ccc(C(Cc2ccc(SC)cc2)=NO)cc1F>>COc1ccc(-c2noc(C)c2-c2ccc(SC)cc2)cc1F | FC=1C=C(C=CC1OC)C(CC1=CC=C(C=C1)SC)=NO.C(C)(=O)OC(C)=O>>FC=1C=C(C=CC1OC)C1=NOC(=C1C1=CC=C(C=C1)SC)C | CC(=O)O[C:10](=O)[CH3:11].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[N:8][OH:9])[CH2:12][c:13]2[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]2)[cH:21][c:22]1[F:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH3:11])[c:12]2-[c:13]2[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]2)[cH:21][c:22]1... | CC(=O)OC(C)=O.COc1ccc(C(Cc2ccc(SC)cc2)=NO)cc1F | COc1ccc(-c2noc(C)c2-c2ccc(SC)cc2)cc1F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6e90b2cff34a94737f5a3ac6e9191c7ff578ee46b13d91424e83f41eb68e817c | fe3e6762590177c290f284bf0a605cc085e349c79dc32d2c64aa22c2fd6d1a4d | c1ccc(-c2conc2-c2ccccc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[OH;D1;+0:3]-[N;H0;D2;+0:4]=[C;H0;D3;+0:5](-[CH2;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[o;H0;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c;H0;D3;... | 30 | [{"value": 30.0, "product": "FC=1C=C(C=CC1OC)C1=NOC(=C1C1=CC=C(C=C1)SC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Fluoro-4-methoxyphenyl)-5-methyl-4-[4-(methylthio)phenyl]isoxazole was prepared in 30% yield from 1-(3-fluoro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one oxime from Step 2 and acetic anhydride by the procedure described in Example 4, Step 1 and used directly in the next step.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Oxime | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COc1ccc(C(Cc2ccc(SC)cc2)=NO)cc1F>>COc1ccc(-c2noc(C)c2-c2ccc(SC)cc2)cc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-910b64cf7107460095428f271d09d2fa | CC(=O)Cl.COc1ccccc1Cl>>COc1ccc(C(C)=O)cc1Cl | C(C)(=O)Cl.ClC1=C(C=CC=C1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C(C)O>>CC(=O)C1=CC(=C(C=C1)OC)Cl | Cl[C:7]([CH3:8])=[O:9].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:10][c:11]1[Cl:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([CH3:8])=[O:9])[cH:10][c:11]1[Cl:12] | CC(=O)Cl.COc1ccccc1Cl | COc1ccc(C(C)=O)cc1Cl | null | null | O.C(Cl)(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | 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] | 76 | [{"value": 76.0, "product": "CC(=O)C1=CC(=C(C=C1)OC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A 5 L round bottomed flask equipped with mechanical stirrer, reflux condenser, constant pressure addition funnel and nitrogen inlet was charged with anhydrous aluminum chloride (281 g, 2.104 mol) and 1 L of ethanol-free chloroform. The solution was maintained at 0° C. with an ice bath while a solution of acetyl chlorid... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O.C(Cl)(Cl)Cl | null | 16 | CC(=O)Cl.COc1ccccc1Cl>O.C(Cl)(Cl)Cl>COc1ccc(C(C)=O)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-29511ae2d0534e249202953b5536c36e | COc1ccc(C(=O)Cc2ccc(SC)cc2)cc1Cl.NO>>COc1ccc(C(Cc2ccc(SC)cc2)=NO)cc1Cl | ClC=1C=C(C=CC1OC)C(CC1=CC=C(C=C1)SC)=O.NO>>ClC=1C=C(C=CC1OC)C(CC1=CC=C(C=C1)SC)=NO | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]([Cl:21])[cH:19]1)[CH2:8][c:9]1[cH:10][cH:11][c:12]([S:13][CH3:14])[cH:15][cH:16]1.[NH2:17][OH:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([S:13][CH3:14])[cH:15][cH:16]2)=[N:17][OH:18])[cH:19][c:20]1[Cl:21] | COc1ccc(C(=O)Cc2ccc(SC)cc2)cc1Cl.NO | COc1ccc(C(Cc2ccc(SC)cc2)=NO)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(Cc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[O;D1;H1:8]-[N;H0;D2;+0:7]=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6] | 41 | [{"value": 41.0, "product": "ClC=1C=C(C=CC1OC)C(CC1=CC=C(C=C1)SC)=NO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(3-Chloro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one oxime was prepared in 41% yield from the reaction of 1-(3 chloro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one from Step 4 with hydroxylamine by the method outlined in Example 1, Step 1: 1H NMR (CDCl3 /300 MHz) δ 7.69 (d, J=2.22 Hz, 1H), 7.47 (dd... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1ccc(C(=O)Cc2ccc(SC)cc2)cc1Cl.NO>>COc1ccc(C(Cc2ccc(SC)cc2)=NO)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-685ec2226bcb42d28fd7ce5dc2b140b9 | COc1ccc(-c2noc(C)c2-c2ccc(S(C)(=O)=O)cc2)cc1Cl>>COc1ccc(-c2noc(C)c2-c2ccc(SC)cc2)cc1Cl | OOS(=O)[O-].[K+].ClC=1C=C(C=CC1OC)C(CC1=CC=C(C=C1)SC)=NO.C(C)(=O)OC(C)=O.ClC=1C=C(C=CC1OC)C1=NOC(=C1C1=CC=C(C=C1)S(=O)(=O)C)C>>ClC=1C=C(C=CC1OC)C1=NOC(=C1C1=CC=C(C=C1)SC)C | O=[S:17](=O)([c:16]1[cH:15][cH:14][c:13](-[c:12]2[c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:22]([Cl:23])[cH:21]3)[n:8][o:9][c:10]2[CH3:11])[cH:20][cH:19]1)[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH3:11])[c:12]2-[c:13]2[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]2)[cH:21][c:22]1[... | COc1ccc(-c2noc(C)c2-c2ccc(S(C)(=O)=O)cc2)cc1Cl | COc1ccc(-c2noc(C)c2-c2ccc(SC)cc2)cc1Cl | null | null | null | Reduction | OtherReaction | 0517548dff678b0d6f5fc405b7a81380838a19b621aa4d2114f0e4e265d45db0 | f1f027a7efd4c0d9bc26319b1a5badbb8108690042954240f04853270d103169 | c1ccc(-c2conc2-c2ccccc2)cc1 | O=[S;H0;D4;+0:1](=O)(-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:2]-[S;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | 26 | [{"value": 26.0, "product": "ClC=1C=C(C=CC1OC)C1=NOC(=C1C1=CC=C(C=C1)SC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Chloro-4-methoxyphenyl)-5-methyl-4-[4-(methylthio)phenyl]isoxazole was prepared in 26% yield from 1-(3-chloro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one oxime from Step 5 and acetic anhydride by the method described in Example 4, Step 1 and then oxidized to 3-(3-chloro-4 methoxyphenyl)-5-methyl-4-[4-met... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Monosulfide | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | Other | null | null | null | COc1ccc(-c2noc(C)c2-c2ccc(S(C)(=O)=O)cc2)cc1Cl>>COc1ccc(-c2noc(C)c2-c2ccc(SC)cc2)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2d606d6d3667474d86be1b3b1f0f8478 | CCO[Si](C)(C)[Si](C)(OCC)OCC>>CCO[Si](C)(C)[Si](C)(C)OCC | C[Li].[SiH3][SiH3].C[Li].C[Si]([Si](OCC)(OCC)C)(OCC)C>>C[Si]([Si](OCC)(C)C)(OCC)C | CCO[Si:7]([Si:4]([O:3][CH2:2][CH3:1])([CH3:5])[CH3:6])([CH3:8])[O:10][CH2:11][CH3:12]>>[CH3:1][CH2:2][O:3][Si:4]([CH3:5])([CH3:6])[Si:7]([CH3:8])([CH3:9])[O:10][CH2:11][CH3:12] | CCO[Si](C)(C)[Si](C)(OCC)OCC | CCO[Si](C)(C)[Si](C)(C)OCC | null | null | null | Functional Group Interconversion | OtherReaction | 2a094323228e6c897bc4d3422b60e2e1f170cc555516918c0a4ca831bb19d92a | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | null | C-C-O-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[#8:3]-[C:4])-[#14:5](-[#8:6])(-[C;D1;H3:7])-[C;D1;H3:8]>>[#8:6]-[#14:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:9])-[#8:3]-[C:4] | null | [] | null | null | null | null | In the same manner as in Example 1, change of the average molecular weight of the resulting polysilanes was examined by changing the amount of methyl lithium to be used as a reaction starting compound. The results including those of Example 1 and the yields and properties of the products are shown in Table 1. In Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | null | null | null | HO- | null | null | null | CCO[Si](C)(C)[Si](C)(OCC)OCC>>CCO[Si](C)(C)[Si](C)(C)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-da8af5adbeb644219123efaf215caaa5 | C1CO1.CC(C)c1cccc(C(C)C)c1Br>>CC(C)c1cccc(C(C)C)c1C(C)O | C(C)(C)C1=C(C(=CC=C1)C(C)C)Br.C1CO1.[NH4+].[Cl-]>>C(C)(C)C1=C(C(=CC=C1)C(C)C)C(C)O | [CH2:13]1[CH2:14][O:15]1.Br[c:12]1[c:4]([CH:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][c:8]1[CH:9]([CH3:10])[CH3:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[CH:13]([CH3:14])[OH:15] | C1CO1.CC(C)c1cccc(C(C)C)c1Br | CC(C)c1cccc(C(C)C)c1C(C)O | null | null | CCOCC | C-C Coupling | OtherReaction | fe9b1026862bafa5af476ea37b65f4571fe973f56d02ac2e70c4fc844fb9c746 | 79fd712a2a6d6b4abbd49e003e84f4018bdf16c930e348b877ef642996ef6e0f | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C:3]):[c:4]):[c:5](-[C:6]):[c:7].[CH2;D2;+0:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[CH;D3;+0:8](-[CH3;D1;+0:9])-[OH;D1;+0:10]):[c:5](-[C:6]):[c:7] | null | [] | null | null | 4 | HOUR | 2,6 diisopropylbromobenzene (see J. Org. Chem., 42(14):2426-2431 (1977) for preparation) (30 g, 124.4 mmol) was added to a suspension of Li powder (1.9 g, 273.6 mmol) in ether (100 nIL) heated under reflux, the heating was continued for another 4 hours, cooled, and the mixture was poured into ethylene oxide which was p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Secondary alcohol | C1CO1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CCOCC | null | 4 | C1CO1.CC(C)c1cccc(C(C)C)c1Br>CCOCC>CC(C)c1cccc(C(C)C)c1C(C)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3b4d52e0b1ee4171bff7d7d670e8bc53 | CC(C)c1cc(C(C)C)c(OS(N)(=O)=O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1cccc(C(C)C)c1CC(=O)c1c(C(C)C)cc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.S(N)(OC1=C(C=CC=C1C(C)C)C(C)C)(=O)=O.S(N)(OC1=C(C=C(C=C1C(C)C)C(C)C)C(C)C)(=O)=O>>CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1C(C)C)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cc([CH:18]([CH3:19])[CH3:20])cc(C(C)C)c1OS(N)(=O)=O.[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[CH2:13][C:14](=[O:15])[c:16]1[cH:17][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[c:26]([O:27][S:28]([NH2:29])(=[O:30])=[O:31])[c:32]1[CH:33]([CH3:34])[CH3:35]>>[CH3:1][CH:2]([CH3:3... | CC(C)c1cc(C(C)C)c(OS(N)(=O)=O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)c1c(C(C)C)cc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | null | null | null | C-C Coupling | OtherReaction | 45b817a4287e0fef1be551660a429f9db14891b95a5baac89000f1e7647c46bc | 6c3a27bb1961729917346e56bc75269d7c337cb0b436676503bcbe5e4be876cc | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c(-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):c:c(-C(-C)-C):c:1-O-S(-N)(=O)=O.[C:4]-[C:5](=[O;D1;H0:6])-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:4]-[C:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c;H0;D3;+0:9](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:10]:[c:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisoproplyphenyl sulfamate was replaced with 2,4,6-triisoproplyphenyl sulfamate, mp 152°-155° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(OS(N)(=O)=O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1cccc(C(C)C)c1CC(=O)c1c(C(C)C)cc(C(C)C)c(OS(N)(=O)=O)c1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e954e282dfa64573998a8376e668ca24 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(Cl)CC12CC3CC(CC(C3)C1)C2>>CC(C)c1ccc(C(=O)CC23CC4CC(CC(C4)C2)C3)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)Cl.C12(CC3CC(CC(C1)C3)C2)CC(=O)Cl>>C12(CC3CC(CC(C1)C3)C2)CC(=O)C=2C(=C(C(=CC2)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:10][C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:25]([O:26][S:27]([NH2:28])(=[O:29])=[O:30])[c:21]1[CH:22]([CH3:23])[CH3:24])=[O:9].O=C(Cl)C[C:11]12[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:18]3)[CH2:19]1)[CH2:20]2>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9]... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(Cl)CC12CC3CC(CC(C3)C1)C2 | CC(C)c1ccc(C(=O)CC23CC4CC(CC(C4)C2)C3)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 31782f217739c9a69b51f7c13b274cfd96d4d55f6c0de6869f50c6208e37202b | 69b26536428ec591912ffb144c8cdb749a38c5b256e3343c17966363adac93a6 | O=C(CC12CC3CC(CC(C3)C1)C2)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-C(=O)-C-[C;H0;D4;+0:5](-[C:6]-[C:7])(-[C:8]-[C:9])-[C:10]-[C:11]>>[C:7]-[C:6]-[C;H0;D4;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4])(-[C:8]-[C:9])-[C:10]-[C:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetyl chloride was replaced with adamantaneacetyl chloride; 1HNMR(CDCl3):1.21 (d, 12H), 1.6-2.0 (m, 15H), 2.15 (s, 2H), 3.4 (m, 2H), 7.15-7.25 (m, 3H) ppm.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone | c1ccccc1.C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | c1ccccc1.C1C2CC3CC1CC(C2)C3 | HCl | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(Cl)CC12CC3CC(CC(C3)C1)C2>>CC(C)c1ccc(C(=O)CC23CC4CC(CC(C4)C2)C3)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bce51b72e30d439bbb1868b775a9fdee | CC(C)c1cc(C(C)C)c(C(=O)Cl)c(C(C)C)c1>>CC(C)c1cc(C(C)C)c(CO)c(C(C)C)c1 | C(C)(C)C1=C(C(=O)Cl)C(=CC(=C1)C(C)C)C(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S(=O)(=O)[O-].[Na+].[Na+]>>C(C)(C)C1=C(CO)C(=CC(=C1)C(C)C)C(C)C | Cl[C:11]([c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:17][c:13]1[CH:14]([CH3:15])[CH3:16])=[O:12]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([CH2:11][OH:12])[c:13]([CH:14]([CH3:15])[CH3:16])[cH:17]1 | CC(C)c1cc(C(C)C)c(C(=O)Cl)c(C(C)C)c1 | CC(C)c1cc(C(C)C)c(CO)c(C(C)C)c1 | null | null | CCOCC | Reduction | OtherReaction | 8431f374ce9ad2153ebbb58bf5a136b25334289c181ba9f7fc40a3ace75a4f68 | f36a544110316fc8e65c8ad2277021c19b4b9c72a75d9a07732094de73e7ab4f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of commercially available 2,4,6-triiso-propylbenzoyl chloride (35 g, 131.2 mmol) in 400 mL ether was added slowly to a suspension of lithium aluminum hydride (LAH) (4.89 g, 131.2 mmol) in ether (300 mL) at -15° C. The mixture was slowly warmed to room temperature over 18 hours. Saturated Na2SO4 solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Primary alcohol | null | null | c1ccccc1 | Other | CCOCC | null | null | CC(C)c1cc(C(C)C)c(C(=O)Cl)c(C(C)C)c1>CCOCC>CC(C)c1cc(C(C)C)c(CO)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9d7460f0cb01456c9721e72993467fc8 | BrP(Br)Br.CC(C)c1cc(C(C)C)c(CO)c(C(C)C)c1>>CC(C)c1cc(C(C)C)c(CBr)c(C(C)C)c1 | P(Br)(Br)Br.C(C)(C)C1=C(CO)C(=CC(=C1)C(C)C)C(C)C.CCO>>C(C)(C)C1=C(CBr)C(=CC(=C1)C(C)C)C(C)C | BrP(Br)[Br:12].O[CH2:11][c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:17][c:13]1[CH:14]([CH3:15])[CH3:16]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([CH2:11][Br:12])[c:13]([CH:14]([CH3:15])[CH3:16])[cH:17]1 | BrP(Br)Br.CC(C)c1cc(C(C)C)c(CO)c(C(C)C)c1 | CC(C)c1cc(C(C)C)c(CBr)c(C(C)C)c1 | null | null | CCOCC | Functional Group Interconversion | PBr3 and alcohol to alkyl bromide | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | A solution of PBr3 (2.7 9, 10 mmol) in ether (10 mL) was added slowly to a solution of 2,4,6-triisopropylbenzyl alcohol (4.68 9, 20 mmol) in 20 mL of ether at room temperature. The mixture was stirred for 1 hour, 5 mL of absolute EtOH was added, and stirring was continued for another 0.5 hour. The solvent was removed a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | CCOCC | null | 1 | BrP(Br)Br.CC(C)c1cc(C(C)C)c(CO)c(C(C)C)c1>CCOCC>CC(C)c1cc(C(C)C)c(CBr)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-59aa947432e84f2dacbc8cc686c3b4b5 | CC(C)c1cc(C(C)C)c(CBr)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1OS(=O)(=O)N=C=O>>CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | C(C)(C)C1=C(CBr)C(=CC(=C1)C(C)C)C(C)C.[NH4+].[Cl-].CCOC(=O)C.C(C)(C)C1=C(OS(=O)(=O)N=C=O)C(=CC=C1)C(C)C>>CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | Br[CH2:11][c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:35][c:31]1[CH:32]([CH3:33])[CH3:34].[C:12](=[O:13])=[N:24][S:23]([O:22][c:21]1[c:17]([CH:18]([CH3:19])[CH3:20])[cH:16][cH:15][cH:14][c:27]1[CH:28]([CH3:29])[CH3:30])(=[O:25])=[O:26]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:... | CC(C)c1cc(C(C)C)c(CBr)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1OS(=O)(=O)N=C=O | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 79c88f76a5ce8d3c7e3ae250f2796cf7d0134ab1c118964408e6e97cddfe8099 | f2be04f046601e1454eef93d9455cc4b2394b63384599d5fe756febe49eafb21 | O=C(Cc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6](:[c:7]-[#8:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[C:5]-[c:6](:[c:7]-[#8:8]-[#16:9](-[NH2;D1;+0:12])(=[O;D1;H0:10])=[O;D1;H0:11]):[c;H0;D3;+0:15](-[C;H0;D3;+0:13](=[O;D1;H0:14])-[CH2;D2;+0:1]-[c... | 67 | [{"value": 67.0, "product": "CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 2,4,6-triisopropylbenzyl bromide (12 g, 40.4 retool) in dry THF (160 nIL) was added to a suspension of Mg powder (1.96 g, 80.8 retool) (4 hours) in THF (20 mL) heated under reflux. 2,6-Diisopropylphenoxysulfonyl isocyanate (ROSO2NCO) (see Phos. and Sulf., 19:167 (1984) for preparation) (11.45 g, 40.4 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Sulfonamide.Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | C1CCOC1 | null | 2 | CC(C)c1cc(C(C)C)c(CBr)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1OS(=O)(=O)N=C=O>C1CCOC1>CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-82d527b28f674730844aadda2b4b4560 | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.[Cl][Mg][CH2]c1ccccc1>>CC(C)c1ccc(C(=O)Cc2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C[Mg]Br)C(=CC(=C1)C(C)C)C(C)C.C(C1=CC=CC=C1)[Mg]Cl>>C1(=CC=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cc(C(C)C)c([CH2:10][C:8]([c:7]2[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:21]([O:22][S:23]([NH2:24])(=[O:25])=[O:26])[c:17]2[CH:18]([CH3:19])[CH3:20])=[O:9])c(C(C)C)c1.[Cl][Mg][CH2][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:1... | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.[Cl][Mg][CH2]c1ccccc1 | CC(C)c1ccc(C(=O)Cc2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | e27da2e34f4a0d2455cc704f5ddd4540bff63a0764794ca1a20632f775b28b34 | 135f2ea95ad9a9b731f59e3aadf4d42e0f9aa41135665e9340592661a7692c1c | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]):c(-C(-C)-C):c:1.[Cl]-[Mg]-[CH2]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9] | null | [] | null | null | null | null | This compound was prepared in the same manner as the title compound of Example 5, except that 2,4,6-triisopropylbenzyl magnesium bromide was replaced with benzylmagnesium chloride (commercially available), mp 150°-152° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl.Mg | null | null | null | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.[Cl][Mg][CH2]c1ccccc1>>CC(C)c1ccc(C(=O)Cc2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b614b1304e3745119fb370774d616c34 | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1OS(=O)(=O)N=C=O>>CC(C)c1cc(C(C)C)c(CC(=O)c2c(C(C)C)cc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(OS(=O)(=O)N=C=O)C(=CC=C1)C(C)C.C(C)(C)C1=C(OS(=O)(=O)N=C=O)C(=CC(=C1)C(C)C)C(C)C>>CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CC(=O)C=1C(=C(C(=CC1C(C)C)C(C)C)OS(N)(=O)=O)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([CH2:11][C:12](=[O:13])[c:14]2[cH:15][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[c:24]([O:25][S:26]([NH2:27])(=[O:28])=[O:29])[c:30]2[CH:31]([CH3:32])[CH3:33])[c:34]([CH:35]([CH3:36])[CH3:37])[cH:38]1.CC(C)c1cccc([CH:16]([CH3:17])[CH3:18])c1OS(=O)(=O)N=... | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1OS(=O)(=O)N=C=O | CC(C)c1cc(C(C)C)c(CC(=O)c2c(C(C)C)cc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | null | null | null | C-C Coupling | OtherReaction | dfcd40a9c5cb19499df15f0c9c649178fafd01980f887df2bfb8cee38e86c022 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):c:1-O-S(=O)(=O)-N=C=O.[C:4]-[C:5](=[O;D1;H0:6])-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:4]-[C:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c;H0;D3;+0:9](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]):[c:10]:[c:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as the title compound of Example 5, except that 2,6-diisopropylphenoxy sulfonyl isocyanate was replaced with 2,4,6-triisopropylphenoxy sulfonyl isocyanate, mp 178°-180° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1OS(=O)(=O)N=C=O>>CC(C)c1cc(C(C)C)c(CC(=O)c2c(C(C)C)cc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c09943d57a0e41e9be3779e433d8d863 | CC(C)c1cc(C(C)C)c(CS(N)(=O)=O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)Cl>>CC(C)c1cc(C(C)C)c(CS(=O)(=O)NC(=O)Cc2c(C(C)C)cccc2C(C)C)c(C(C)C)c1 | C(C)(C)C1=C(CS(=O)(=O)N)C(=CC(=C1)C(C)C)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)Cl.CCN(CC)CC>>CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)NS(=O)(=O)CC1=C(C=C(C=C1C(C)C)C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([CH2:11][S:12](=[O:13])(=[O:14])[NH2:15])[c:31]([CH:32]([CH3:33])[CH3:34])[cH:35]1.Cl[C:16](=[O:17])[CH2:18][c:19]1[c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25][cH:26][c:27]1[CH:28]([CH3:29])[CH3:30]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7](... | CC(C)c1cc(C(C)C)c(CS(N)(=O)=O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)Cl | CC(C)c1cc(C(C)C)c(CS(=O)(=O)NC(=O)Cc2c(C(C)C)cccc2C(C)C)c(C(C)C)c1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 403eb34e708e50f7077a9da490b1654c837258ce901614ddd1204eb6f2a10a27 | 37dfa12f19cd8cec29206fb8a18b7504935d92bc326a2084e9ef8a13076d3b87 | O=C(Cc1ccccc1)NS(=O)(=O)Cc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]-[#16:6](-[NH2;D1;+0:7])(=[O;D1;H0:8])=[O;D1;H0:9]>>[C:5]-[#16:6](=[O;D1;H0:8])(=[O;D1;H0:9])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 12.1 | [{"value": 12.0, "product": "CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)NS(=O)(=O)CC1=C(C=C(C=C1C(C)C)C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.1, "product": "CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)NS(=O)(=O)CC1=C(C=C(C=C1C(C)C)C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,4,6 - triisopropylbenzylsulfonamide (100 mg, 0.33 mmol), 2,6-diisopropylphenylacetyl chloride (75 mg, 0.34 mmol), and Et3N (47 μL, 0.34 mmol) in 10 mL THF was stirred at room temperature overnight. The solvent was evaporated and the residue was distributed between ethyl acetate and 0.1N HCl, the organic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | null | CC(C)c1cc(C(C)C)c(CS(N)(=O)=O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)Cl>C1CCOC1>CC(C)c1cc(C(C)C)c(CS(=O)(=O)NC(=O)Cc2c(C(C)C)cccc2C(C)C)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b76055632cb84b10898976d597001a24 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCCCCCCCCC(=O)Cl>>CCCCCCCCCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)Cl.C(CCCCCCCCC)(=O)Cl>>C(CCCCCCCCC)(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[c:19]([O:20][S:21]([NH2:22])(=[O:23])=[O:24])[c:25]1[CH:26]([CH3:27])[CH3:28].O=C(Cl)C[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCCCCCCCCC(=O)Cl | CCCCCCCCCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | null | null | null | C-C Coupling | OtherReaction | b399da0096243e591910b10ed47444190c0d072e2e69551181f2dfe786acc1a1 | 69b26536428ec591912ffb144c8cdb749a38c5b256e3343c17966363adac93a6 | c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-C(=O)-C-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetyl chloride was replaced with decanoyl chloride, mp 92°-94° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone | c1ccccc1 | null | c1ccccc1 | HCl | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCCCCCCCCC(=O)Cl>>CCCCCCCCCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-da21a9c6d82f48ab97c409c1bf4b6c10 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)Cl.C(CCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCC)(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[c:21]([O:22][S:23]([NH2:24])(=[O:25])=[O:26])[c:27]1[CH:28]([CH3:29])[CH3:30].O=C(Cl)C[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCCCCCCCCCCC(=O)Cl | CCCCCCCCCCCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | null | null | null | C-C Coupling | OtherReaction | b399da0096243e591910b10ed47444190c0d072e2e69551181f2dfe786acc1a1 | 69b26536428ec591912ffb144c8cdb749a38c5b256e3343c17966363adac93a6 | c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-C(=O)-C-[CH2;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[CH2;D2;+0:5]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetyl chloride was replaced with dodecanoyl chloride; 1H NMR (DMSO-26):δ 7.09 (s, 3H), 3.65 (heptet, 2H), 2.05 (t, 2H), 1.48--1.15 (m, 18H); 1.10 (d, 6H), 0.86 (t, 3H) ppm.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone | c1ccccc1 | null | c1ccccc1 | HCl | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9878b200813744d5a089be18d9e692d3 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)CC(c1ccccc1)c1ccccc1>>CC(C)c1ccc(C(=O)CC(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1(=CC=CC=C1)C(CC(=O)O)C1=CC=CC=C1>>O=C(CC(C1=CC=CC=C1)C1=CC=CC=C1)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:28]([O:29][S:30]([NH2:31])(=[O:32])=[O:33])[c:24]1[CH:25]([CH3:26])[CH3:27].O[C:8](=[O:9])[CH2:10][CH:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)CC(c1ccccc1)c1ccccc1 | CC(C)c1ccc(C(=O)CC(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(CC(c1ccccc1)c1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 3,3-diphenylpropionic acid, mp 149°-152° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)CC(c1ccccc1)c1ccccc1>>CC(C)c1ccc(C(=O)CC(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9a8b83031a6a4f9d821ddccd1fc2046e | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1c(Cl)cccc1Cl>>CC(C)c1ccc(C(=O)Cc2c(Cl)cccc2Cl)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.ClC1=C(C(=CC=C1)Cl)CC(=O)O>>ClC1=C(C(=CC=C1)Cl)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:10][C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:23]([O:24][S:25]([NH2:26])(=[O:27])=[O:28])[c:19]1[CH:20]([CH3:21])[CH3:22])=[O:9].O=C(O)C[c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][c:11]2[c:12]([Cl:13... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1c(Cl)cccc1Cl | CC(C)c1ccc(C(=O)Cc2c(Cl)cccc2Cl)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O-C(=O)-C-[c;H0;D3;+0:5](:[c:6](-[Cl;D1;H0:7]):[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:7]-[c:6](:[c:8]):[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]):[c:9](-[Cl;D1;H0:10]):[c:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 2,6-dichlorophenylacetic acid, mp 203°-205° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1c(Cl)cccc1Cl>>CC(C)c1ccc(C(=O)Cc2c(Cl)cccc2Cl)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b1a0f5d6526b462fa06c1340d84034a8 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)[C@@H]1C[C@H]1c1ccccc1>>CC(C)c1ccc(C(=O)[C@@H]2C[C@H]2c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1(=CC=CC=C1)[C@H]1[C@@H](C1)C(=O)O>>C1(=CC=CC=C1)[C@H]1[C@@H](C1)C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:23]([O:24][S:25]([NH2:26])(=[O:27])=[O:28])[c:19]1[CH:20]([CH3:21])[CH3:22].O[C:8](=[O:9])[C@@H:10]1[CH2:11][C@H:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[C@@H:10]2[CH2:11][C@H:... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)[C@@H]1C[C@H]1c1ccccc1 | CC(C)c1ccc(C(=O)[C@@H]2C[C@H]2c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)[C@@H]1C[C@H]1c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-1>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-1):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with trans-2-phenylcyclopropylcarboxylic acid, mp 166°-168° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)[C@@H]1C[C@H]1c1ccccc1>>CC(C)c1ccc(C(=O)[C@@H]2C[C@H]2c2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e2229a72666645d38244e073b8a88481 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1ccc(OC)c(CC(=O)Cl)c1>>COc1ccc(OC)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c1 | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)Cl.COC1=C(C=C(C=C1)OC)CC(=O)Cl>>COC1=C(C=C(C=C1)OC)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[c:20]([O:21][S:22]([NH2:23])(=[O:24])=[O:25])[c:26]1[CH:27]([CH3:28])[CH3:29].O=C(Cl)C[c:9]1[c:6]([O:7][CH3:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([CH2:10][C:11](... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1ccc(OC)c(CC(=O)Cl)c1 | COc1ccc(OC)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c1 | null | null | null | C-C Coupling | OtherReaction | 966e4fee9e57725371b772115d38bc42a284d08321d8e21209a7eb63eb4fcd19 | 69b26536428ec591912ffb144c8cdb749a38c5b256e3343c17966363adac93a6 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].Cl-C(=O)-C-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[#8:9]):[c:10]>>[#8:9]-[c:8](:[c:10]):[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]):[c:6]:[c:7] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetyl chloride was replaced with 2,5-dimethoxyphenylacetyl chloride, mp 150°-152° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1ccc(OC)c(CC(=O)Cl)c1>>COc1ccc(OC)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-19809ad545844ab1a8918acd129c31e2 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1cc(OC)c(CC(=O)O)c(OC)c1>>COc1cc(OC)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(OC)c1 | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.COC1=C(C(=CC(=C1)OC)OC)CC(=O)O>>COC1=C(C(=CC(=C1)OC)OC)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[c:19]([O:20][S:21]([NH2:22])(=[O:23])=[O:24])[c:25]1[CH:26]([CH3:27])[CH3:28].O=C(O)C[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:32][c:29]1[O:30][CH3:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH2:9][C... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1cc(OC)c(CC(=O)O)c(OC)c1 | COc1cc(OC)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(OC)c1 | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O-C(=O)-C-[c;H0;D3;+0:5](:[c:6](-[#8:7]):[c:8]):[c:9](-[#8:10]):[c:11]>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]):[c:9](-[#8:10]):[c:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 2,4,6-trimethoxyphenylacetic acid, mp 159°-163° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1cc(OC)c(CC(=O)O)c(OC)c1>>COc1cc(OC)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(OC)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0d049afbc8f14ed7b6fd109189e0aa58 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.Cc1cc(C)c(CC(=O)O)c(C)c1>>Cc1cc(C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C)c1 | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.CC1=C(C(=CC(=C1)C)C)CC(=O)O>>CC1=C(C(=CC(=C1)C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)[c:6]1[CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[c:17]([O:18][S:19]([NH2:20])(=[O:21])=[O:22])[c:23]1[CH:24]([CH3:25])[CH3:26].O=C(O)Cc1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:29][c:27]1[CH3:28]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][C:8](=[O:9])[c:10]2[cH:11][cH... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.Cc1cc(C)c(CC(=O)O)c(C)c1 | Cc1cc(C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C)c1 | null | null | null | Miscellaneous | OtherReaction | 8af86c4eb36c660a456c3b64a059e91e5119d1a302847b8c8e25e7542d4ffeeb | 2464b583d940c451c00c1488740fdde63610bb85f8f9a614db893662c6ccb8a2 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):[c;H0;D3;+0:1]:1-[C:2]-[C:3](=[O;D1;H0:4])-[c:5].O-C(=O)-C-c1:[c;H0;D3;+0:6](-[C;D1;H3:7]):[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:1-[C;D1;H3:12]>>[C;D1;H3:7]-[c;H0;D3;+0:6]1:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11](-[C;D1;H3:12]):[c;H0;D3;+0:1]:1-[C:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 2,4,6-trimethylphenylacetic acid, mp 159°-161° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.Cc1cc(C)c(CC(=O)O)c(C)c1>>Cc1cc(C)c(CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ea0d8d5fe0e647f89b215f3a75b08577 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1cccs1>>CC(C)c1ccc(C(=O)Cc2cccs2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.S1C(=CC=C1)CC(=O)O>>S1C(=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:20]([O:21][S:22]([NH2:23])(=[O:24])=[O:25])[c:16]1[CH:17]([CH3:18])[CH3:19].O[C:8](=[O:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][s:15]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:13][cH:14][s:15]2)[c:16]... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1cccs1 | CC(C)c1ccc(C(=O)Cc2cccs2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1cccs1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[c:10]:[#16;a:11]>>[#16;a:11]:[c:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 2-thiopheneacetic acid, mp 133°-136° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1cccs1>>CC(C)c1ccc(C(=O)Cc2cccs2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1ce273fb23af45c1a588f588052dcb3f | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1ccsc1>>CC(C)c1ccc(C(=O)Cc2ccsc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.S1C=C(C=C1)CC(=O)O>>S1C=C(C=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:20]([O:21][S:22]([NH2:23])(=[O:24])=[O:25])[c:16]1[CH:17]([CH3:18])[CH3:19].O[C:8](=[O:9])[CH2:10][c:11]1[cH:12][cH:13][s:14][cH:15]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:13][s:14][cH:15]2)[c:16]... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1ccsc1 | CC(C)c1ccc(C(=O)Cc2ccsc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1ccsc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[c:10]:[c:11]:[#16;a:12]>>[#16;a:12]:[c:11]:[c:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared in the same manner as 5 for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 3-thiopheneacetic acid, mp 136°-138° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1ccsc1>>CC(C)c1ccc(C(=O)Cc2ccsc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-88f9f92210aa4b5c86549ac389be44f2 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1ccccc1CC(=O)O>>COc1ccccc1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.COC1=C(C=CC=C1)CC(=O)O>>COC1=C(C=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[c:19]([O:20][S:21]([NH2:22])(=[O:23])=[O:24])[c:25]1[CH:26]([CH3:27])[CH3:28].O=C(O)C[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][C:10](=[O:11])[c:12]1[cH:13][c... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1ccccc1CC(=O)O | COc1ccccc1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O-C(=O)-C-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[#8:9]):[c:10]>>[#8:9]-[c:8](:[c:10]):[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]):[c:6]:[c:7] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 2-methoxyphenylacetic acid, mp 159°-161° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.COc1ccccc1CC(=O)O>>COc1ccccc1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-499982a4b04547d4972e2ae6e3a13543 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(=O)c1ccccc1>>CC(C)c1ccc(C(=O)C(=O)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C(C1=CC=CC=C1)(=O)C(=O)O>>O=C(C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C)C1=CC=CC=C1 | CC(C)c1cccc(C(C)C)c1C[C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:22]([O:23][S:24]([NH2:25])(=[O:26])=[O:27])[c:18]1[CH:19]([CH3:20])[CH3:21])=[O:9].O=C(O)[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(=O)c1ccccc1 | CC(C)c1ccc(C(=O)C(=O)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 30751afd355380efe6c3d1236ad74ac6a1fceab5f2f64b0b0446f3787e737bbd | aef935df5383b0b345ee1db59a00fa855d9875a401b4c26871f2c4a2111cfc51 | O=C(C(=O)c1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-C(=O)-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with benzoylformic acid, mp 106°-109° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ketone | Ketone.Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(=O)c1ccccc1>>CC(C)c1ccc(C(=O)C(=O)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7dcd9edec46e48cb871afa158b778266 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1ccccc1C(F)(F)F>>CC(C)c1ccc(C(=O)Cc2ccccc2C(F)(F)F)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.FC(C1=C(C=CC=C1)CC(=O)O)(F)F>>FC(C1=C(C=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C)(F)F | CC(C)c1cccc(C(C)C)c1C[C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:25]([O:26][S:27]([NH2:28])(=[O:29])=[O:30])[c:21]1[CH:22]([CH3:23])[CH3:24])=[O:9].O=C(O)[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([F:18])([F:19])[F:20]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][c:11]2... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1ccccc1C(F)(F)F | CC(C)c1ccc(C(=O)Cc2ccccc2C(F)(F)F)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 2993f843cf60c11e9042e35f393787eaa0fda8934ce7f17704dcc66aa32ff121 | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-C(=O)-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 2-trifluoromethylphenylacetic acid, mp 144°-149° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)Cc1ccccc1C(F)(F)F>>CC(C)c1ccc(C(=O)Cc2ccccc2C(F)(F)F)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c21d464dc0f844728a03ccf71ba05932 | CC(C(=O)O)c1ccccc1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1ccc(C(=O)C(C)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1(=CC=CC=C1)C(C(=O)O)C>>O=C(C(C)C1=CC=CC=C1)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | O=C(O)[CH:10]([CH3:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.CC(C)c1cccc(C(C)C)c1C[C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:22]([O:23][S:24]([NH2:25])(=[O:26])=[O:27])[c:18]1[CH:19]([CH3:20])[CH3:21])=[O:9]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH:10]([CH3:11])[c:12]2[cH:13][c... | CC(C(=O)O)c1ccccc1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)c1ccc(C(=O)C(C)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 2993f843cf60c11e9042e35f393787eaa0fda8934ce7f17704dcc66aa32ff121 | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-C(=O)-[CH;D3;+0:6](-[C;D1;H3:7])-[c:8](:[c:9]):[c:10]>>[C;D1;H3:7]-[CH;D3;+0:6](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with α-phenylpropionic acid, mp 142°-144° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C(=O)O)c1ccccc1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1ccc(C(=O)C(C)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c9315d6dce004175a74bb11b068e805f | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(c1ccccc1)c1ccccc1>>CC(C)c1ccc(C(=O)C(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1(=CC=CC=C1)C(C(=O)O)C1=CC=CC=C1>>C1(=CC=CC=C1)C(C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C)C1=CC=CC=C1 | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:27]([O:28][S:29]([NH2:30])(=[O:31])=[O:32])[c:23]1[CH:24]([CH3:25])[CH3:26].O[C:8](=[O:9])[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(c1ccccc1)c1ccccc1 | CC(C)c1ccc(C(=O)C(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C(c1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[c:10])-[c:11]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[c:10])-[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with diphenylacetic acid, mp 164°-166° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(c1ccccc1)c1ccccc1>>CC(C)c1ccc(C(=O)C(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3f12480c17dd4016a90f05216d96da1a | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1CCc2ccccc2C1>>CC(C)c1ccc(C(=O)C2CCc3ccccc3C2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1C(CCC2=CC=CC=C12)C(=O)O>>C1C(CCC2=CC=CC=C12)C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:24]([O:25][S:26]([NH2:27])(=[O:28])=[O:29])[c:20]1[CH:21]([CH3:22])[CH3:23].O[C:8](=[O:9])[CH:10]1[CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[CH2:19]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH:10]2[CH2:11][C... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1CCc2ccccc2C1 | CC(C)c1ccc(C(=O)C2CCc3ccccc3C2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C1CCc2ccccc2C1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])-[C:11]>>[C:10]-[C:9](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6])-[C:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 1,2,3,4-tetrahydro-2-naphthoic acid, mp 137°-139° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1CCc2ccccc2C1>>CC(C)c1ccc(C(=O)C2CCc3ccccc3C2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e5b86a70ae3141339209eae007af8d76 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1(c2ccccc2)CCCC1>>CC(C)c1ccc(C(=O)C2(c3ccccc3)CCCC2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1(=CC=CC=C1)C1(CCCC1)C(=O)O>>C1(=CC=CC=C1)C1(CCCC1)C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:25]([O:26][S:27]([NH2:28])(=[O:29])=[O:30])[c:21]1[CH:22]([CH3:23])[CH3:24].O[C:8](=[O:9])[C:10]1([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[C:10]2(... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1(c2ccccc2)CCCC1 | CC(C)c1ccc(C(=O)C2(c3ccccc3)CCCC2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C1(c2ccccc2)CCCC1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[c:10])(-[C:11])-[C:12]>>[C:11]-[C:9](-[c:10])(-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6])-[C:12] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 1-phenyl-1-cyclopentanecarboxylic acid, mp 149°-152° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1(c2ccccc2)CCCC1>>CC(C)c1ccc(C(=O)C2(c3ccccc3)CCCC2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f822be853af245309d397e2f2022d04e | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCC(C(=O)Cl)c1ccccc1>>CCC(C(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C)c1ccccc1 | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)Cl.C1(=CC=CC=C1)C(C(=O)Cl)CC>>O=C(C(CC)C1=CC=CC=C1)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1C[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]([CH3:11])[CH3:12])[c:13]([O:14][S:15]([NH2:16])(=[O:17])=[O:18])[c:19]1[CH:20]([CH3:21])[CH3:22].O=C(Cl)[CH:3]([CH2:2][CH3:1])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][CH2:2][CH:3]([C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]([CH3:11])[CH3:12]... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCC(C(=O)Cl)c1ccccc1 | CCC(C(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | b399da0096243e591910b10ed47444190c0d072e2e69551181f2dfe786acc1a1 | 69b26536428ec591912ffb144c8cdb749a38c5b256e3343c17966363adac93a6 | O=C(Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].Cl-C(=O)-[CH;D3;+0:6](-[C:7]-[C;D1;H3:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H3:8]-[C:7]-[CH;D3;+0:6](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetyl chloride was replaced with 2-phenylbutyryl chloride, mp 142°-145° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.CCC(C(=O)Cl)c1ccccc1>>CCC(C(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-11b231f88dd74258a5a546bd364b2e76 | CC(C)c1cccc(C(C)C)c1CC(=O)O.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1ccc(C(=O)C(c2ccccc2)C2CCCCC2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O>>C1(CCCCC1)C(C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C)C1=CC=CC=C1 | CC(C)[c:11]1[cH:12][cH:13][cH:14][c:15](C(C)C)[c:16]1CC(=O)O.CC(C)[c:18]1[c:17]([CH2:10][C:8]([c:7]2[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:27]([O:28][S:29]([NH2:30])(=[O:31])=[O:32])[c:23]2[CH:24]([CH3:25])[CH3:26])=[O:9])[c:22](C(C)C)[cH:21][cH:20][cH:19]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:... | CC(C)c1cccc(C(C)C)c1CC(=O)O.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)c1ccc(C(=O)C(c2ccccc2)C2CCCCC2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 6291a98db33e6b1745d6ec4a8eec18cf072e3586ae3f47435292354eaf5347df | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C(c1ccccc1)C1CCCCC1 | C-C(-C)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-C(-C)-C):[c;H0;D3;+0:6]:1-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10].C-C(-C)-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-C(-C)-C):[c;H0;D3;+0:16]:1-C-C(-O)=O>>[O;D1;H0:9]=[C:8](-[c:10])-[CH;D3;+0:7](-[CH;D3;+0:6]1-[CH2;D2;+0:1]-[CH2... | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with α-phenylcyclohexanecarboxylic acid, mp 127°-137° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1.C1CCCCC1 | c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)O.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1ccc(C(=O)C(c2ccccc2)C2CCCCC2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-37e055692ee34baba829e58cebf17d0b | CC(C(=O)O)(c1ccccc1)c1ccccc1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1ccc(C(=O)C(C)(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1(=CC=CC=C1)C(C(=O)O)(C)C1=CC=CC=C1>>O=C(C(C)(C1=CC=CC=C1)C1=CC=CC=C1)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | O=C(O)[C:10]([CH3:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.CC(C)c1cccc(C(C)C)c1C[C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:28]([O:29][S:30]([NH2:31])(=[O:32])=[O:33])[c:24]1[CH:25]([CH3:26])[CH3:27])=[O:9]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C... | CC(C(=O)O)(c1ccccc1)c1ccccc1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)c1ccc(C(=O)C(C)(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 2993f843cf60c11e9042e35f393787eaa0fda8934ce7f17704dcc66aa32ff121 | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C(c1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-C(=O)-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]>>[C;D1;H3:7]-[C;H0;D4;+0:6](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6 - diisopropylphenylacetic acid was replaced with 2,2-diphenylpropionic acid, mp 140°-145° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C(=O)O)(c1ccccc1)c1ccccc1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1ccc(C(=O)C(C)(c2ccccc2)c2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6573c7b6e8654db6a34f0eba322536af | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1>>CC(C)c1ccc(C(=O)C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.ClC1=CC=C(C=C1)C(C(=O)O)C1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)C(C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C)C1=CC=C(C=C1)Cl | CC(C)c1cccc(C(C)C)c1C[C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:29]([O:30][S:31]([NH2:32])(=[O:33])=[O:34])[c:25]1[CH:26]([CH3:27])[CH3:28])=[O:9].O=C(O)[CH:10]([c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1 | CC(C)c1ccc(C(=O)C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 2993f843cf60c11e9042e35f393787eaa0fda8934ce7f17704dcc66aa32ff121 | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C(c1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-C(=O)-[CH;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with bis(4-chlorophenyl)acetic acid, mp 175°-176° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1>>CC(C)c1ccc(C(=O)C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-db7cee2379d644998847954b6b5d4f68 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1c2ccccc2-c2ccccc21>>CC(C)c1ccc(C(=O)C2c3ccccc3-c3ccccc32)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C1=CC=CC=2C3=CC=CC=C3C(C12)C(=O)O>>C1=CC=CC=2C3=CC=CC=C3C(C12)C(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1[CH2:10][C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:27]([O:28][S:29]([NH2:30])(=[O:31])=[O:32])[c:23]1[CH:24]([CH3:25])[CH3:26])=[O:9].O=C(O)C1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1c2ccccc2-c2ccccc21 | CC(C)c1ccc(C(=O)C2c3ccccc3-c3ccccc32)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | 980da68534a491de78eadde070690cc0c272e4cb9f64dc077c758cb108e5ca1d | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(c1ccccc1)C1c2ccccc2-c2ccccc21 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O-C(=O)-C1-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](:[c:9])-[c:10](:[c:11]):[c;H0;D3;+0:12]-1:[c:13]:[c:14]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D3;+0:1]1-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](:[c:9])-[c:10](:[c:11]):[c;H0;D3;+0:12]-1:[c:13]:[c:14] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 9-fluorenecarboxylic acid, mp 146°-147° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)C1c2ccccc2-c2ccccc21>>CC(C)c1ccc(C(=O)C2c3ccccc3-c3ccccc32)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2222affdb6d94a64842eaa0485f2dac7 | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)CCc1ccccc1>>CC(C)c1ccc(C(=O)CCc2ccccc2)c(C(C)C)c1OS(N)(=O)=O | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.C(CCC1=CC=CC=C1)(=O)O>>O=C(CCC1=CC=CC=C1)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | CC(C)c1cccc(C(C)C)c1CC(=O)[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:22]([O:23][S:24]([NH2:25])(=[O:26])=[O:27])[c:18]1[CH:19]([CH3:20])[CH3:21].O[C:8](=[O:9])[CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][CH2:11][c:12]2[cH:13][cH:... | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)CCc1ccccc1 | CC(C)c1ccc(C(=O)CCc2ccccc2)c(C(C)C)c1OS(N)(=O)=O | null | null | null | C-C Coupling | OtherReaction | db58d321fc5be7f3584d09bbf1cc1b2f4b58d23174ea1e3813cd262ad613aecb | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(CCc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with hydrocinnamic acid, mp 121°-124° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C.O=C(O)CCc1ccccc1>>CC(C)c1ccc(C(=O)CCc2ccccc2)c(C(C)C)c1OS(N)(=O)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a415a2aa4c31427b970172b8ba449f65 | C=CC(=O)OC.CC(C)c1cc(C(C)C)c(Br)c(C(C)C)c1.CCOC(C)=O>>COC(=O)CC=Cc1c(C(C)C)cc(C(C)C)cc1C(C)C | C(C=C)(=O)OC.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)Br.C(C)(=O)OCC>>CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C=CCC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Br[c:7]1[c:9]([CH:10]([CH3:11])[CH3:12])[cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][c:19]1[CH:20]([CH3:21])[CH3:22].CCOC(=O)[CH3:8]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]=[CH:7][c:8]1[c:9]([CH:10]([CH3:11])[CH3:12])[cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][c:19]1[CH:20... | C=CC(=O)OC.CC(C)c1cc(C(C)C)c(Br)c(C(C)C)c1.CCOC(C)=O | COC(=O)CC=Cc1c(C(C)C)cc(C(C)C)cc1C(C)C | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC.CN(C=O)C | C-C Coupling | OtherReaction | 9ffbab6fbeb0a60929aed252e5827790e30d9a71f06ff1d6d751f1b39529e73a | fb7dc410e7db7c955d230d6eb0fa532a6968cc5c3592ec3c03c25e1fc0a3f0df | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c;H0;D3;+0:2](-[C:3](-[C;D1;H3:4])-[C;D1;H3:5]):[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[C:10](-[C;D1;H3:11])-[C;D1;H3:12].C-C-O-C(=O)-[CH3;D1;+0:13].[C;D1;H3:14]-[#8:15]-[C:16](=[O;D1;H0:17])-[CH;D2;+0:18]=[CH2;D1;+0:19]>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[c;H0;D3;+0:2... | null | [] | null | null | 6 | HOUR | A mixture of methyl acrylate (15.9 mL, 176 mmol) and bis (triphenylphosphine) palladium (II) chloride (0.99 g, 1.4 mmol) in 125 mL dimethylformamide and 125 mL triethylamine was heated to reflux for 1 hour and then 2,4,6 -triisopropylbromobenzene (10.0 g, 35 mmol) was added. Reflux was continued for 6 hours and then st... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Vinyl | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.CN(C=O)C | null | 6 | C=CC(=O)OC.CC(C)c1cc(C(C)C)c(Br)c(C(C)C)c1.CCOC(C)=O>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.CN(C=O)C>COC(=O)CC=Cc1c(C(C)C)cc(C(C)C)cc1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-31bb48e3aefa493c969c0a88c7fc3f77 | COC(=O)CC=Cc1c(C(C)C)cc(C(C)C)cc1C(C)C>>CC(C)c1cc(C(C)C)c(C=CCC(=O)O)c(C(C)C)c1 | [OH-].[Na+].CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C=CCC(=O)OC>>CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C=CCC(=O)O | C[O:16][C:14]([CH2:13][CH:12]=[CH:11][c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:21][c:17]1[CH:18]([CH3:19])[CH3:20])=[O:15]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([CH:11]=[CH:12][CH2:13][C:14](=[O:15])[OH:16])[c:17]([CH:18]([CH3:19])[CH3:20])[cH:21]1 | COC(=O)CC=Cc1c(C(C)C)cc(C(C)C)cc1C(C)C | CC(C)c1cc(C(C)C)c(C=CCC(=O)O)c(C(C)C)c1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]=[C:6]>>[C:6]=[C:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 88.7 | [{"value": 88.7, "product": "CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C=CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Sodium hydroxide (0.23 g, 5.7 mmol) was added to a solution of 3-[2,4,6-tris (1-methylethyl)phenyl]-2-propenyl carboxylic acid, methyl ester (1.5 g, 5.2 mmol) in 100 mL methanol and 10 mL water. Stirred at room temperature for 48 hours and concentrated to dryness. Partitioned the residue between water and diethyl ether... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O.CO | null | 48 | COC(=O)CC=Cc1c(C(C)C)cc(C(C)C)cc1C(C)C>O.CO>CC(C)c1cc(C(C)C)c(C=CCC(=O)O)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5f2251d192ef4cac9dbfd2f584ab989b | CC(C)c1cc(C(C)C)c(C=CCC(=O)O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1cc(C(C)C)c(C=CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C=CCC(=O)O>>O=C(C=CC1=C(C=C(C=C1C(C)C)C(C)C)C(C)C)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C | O=C(O)CC=[CH:11][c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:36][c:32]1[CH:33]([CH3:34])[CH3:35].CC(C)c1cccc(C(C)C)c1[CH2:12][C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[c:22]([O:23][S:24]([NH2:25])(=[O:26])=[O:27])[c:28]1[CH:29]([CH3:30])[CH3:31]>>[CH3:1][CH:2]([C... | CC(C)c1cc(C(C)C)c(C=CCC(=O)O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)c1cc(C(C)C)c(C=CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | null | null | null | C-C Coupling | OtherReaction | 2993f843cf60c11e9042e35f393787eaa0fda8934ce7f17704dcc66aa32ff121 | daa0e318da6948e2bc1760314ca4772f970698227d2c3a9c9ca11760065d3796 | O=C(C=Cc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O-C(=O)-C-C=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 3-[2,4,6-tris(1-methylethyl)phenyl]-2-propenyl carboxylic acid, mp 144°-148° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(C=CCC(=O)O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1cc(C(C)C)c(C=CC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2cb2b66397b5430594af21c6ef05e256 | COC(=O)CCc1c(C(C)C)cc(C(C)C)cc1C(C)C>>CC(C)c1cc(C(C)C)c(CCC(=O)O)c(C(C)C)c1 | CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CCC(=O)OC.[OH-].[Na+]>>CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CCC(=O)O | C[O:15][C:13]([CH2:12][CH2:11][c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:20][c:16]1[CH:17]([CH3:18])[CH3:19])=[O:14]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([CH2:11][CH2:12][C:13](=[O:14])[OH:15])[c:16]([CH:17]([CH3:18])[CH3:19])[cH:20]1 | COC(=O)CCc1c(C(C)C)cc(C(C)C)cc1C(C)C | CC(C)c1cc(C(C)C)c(CCC(=O)O)c(C(C)C)c1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 92.7 | [{"value": 92.7, "product": "CC(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 3-[2,4,6-Tris(1-methylethyl)phenyl]propionic acid, methyl ester (2.12 g, 7.3 mmol) was dissolved in 100 mL methanol and 10 mL water. Sodium hydroxide (0.32 g, 8.0 mmol) was added and the resulting solution was stirred at room temperature for 4 hours. Concentrated in vacuo and partitioned the residue between water and d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O.CO | null | 4 | COC(=O)CCc1c(C(C)C)cc(C(C)C)cc1C(C)C>O.CO>CC(C)c1cc(C(C)C)c(CCC(=O)O)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-983d29117b79435da886a62cf097c7b9 | CC(=O)O.CC(C)c1cc(C(C)C)cc(C(C)C)c1.O=CC(=O)O>>CC(=O)OC(C(=O)O)c1c(C(C)C)cc(C(C)C)cc1C(C)C | C(C=O)(=O)O.C(C)(C)C1=CC(=CC(=C1)C(C)C)C(C)C.C(C)(=O)O>>C(C)(=O)OC(C(=O)O)C1=C(C=C(C=C1C(C)C)C(C)C)C(C)C | [CH3:1][C:2](=[O:3])[OH:4].[cH:9]1[c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][c:20]1[CH:21]([CH3:22])[CH3:23].O=[CH:5][C:6](=[O:7])[OH:8]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][c:20]... | CC(=O)O.CC(C)c1cc(C(C)C)cc(C(C)C)c1.O=CC(=O)O | CC(=O)OC(C(=O)O)c1c(C(C)C)cc(C(C)C)cc1C(C)C | null | null | S(O)(O)(=O)=O | Heteroatom Alkylation and Arylation | OtherReaction | 535cf401e9752d0db2ddd1532ebc568b6e775c4bb46ef03379aa273ae3b62c1f | 257772586559b287f7edfe2e31e33da82c0eb855c0e003f9c513b9c9c7617cfa | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8].[C:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13](-[C:14]):[c:15]>>[C:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH;D3;+0:1](-[O;H0;D2;+0:8]-[C:6](-[C;D1;H3:5])=[O;D1;H0:7])-[C:2](=[O;D1;H0:3])-[O;D1;H1:4]):[c:13](-[C:14]):[c:15] | null | [] | null | null | 16 | HOUR | Glyoxylic acid (1.99 g, 27 mmol) and 1,3,5-triiso-propylbenzene (5.0 g, 24.5 mmol) were mixed in 30 mL glacial acetic acid and 2 mL concentrated sulfuric acid. The resulting solution was heated to reflux for 5 hours and then stirred at room temperature for 16 hours. The reaction mixture was poured into 100 g ice and th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 16 | CC(=O)O.CC(C)c1cc(C(C)C)cc(C(C)C)c1.O=CC(=O)O>S(O)(O)(=O)=O>CC(=O)OC(C(=O)O)c1c(C(C)C)cc(C(C)C)cc1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-25e0b70a444549a7a273b565e9ce509e | CC(C)c1cc(C(C)C)c(O)c(C(C)C)c1.O=C(O)CBr>>CC(C)c1cc(C(C)C)c(OCC(=O)O)c(C(C)C)c1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)O.[H-].[Na+].BrCC(=O)O>>CC(C)C1=C(OCC(=O)O)C(=CC(=C1)C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([OH:11])[c:16]([CH:17]([CH3:18])[CH3:19])[cH:20]1.Br[CH2:12][C:13](=[O:14])[OH:15]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([O:11][CH2:12][C:13](=[O:14])[OH:15])[c:16]([CH:17]([CH3:18])[CH3:19])[cH:20]1 | CC(C)c1cc(C(C)C)c(O)c(C(C)C)c1.O=C(O)CBr | CC(C)c1cc(C(C)C)c(OCC(=O)O)c(C(C)C)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 61.9 | [{"value": 61.9, "product": "CC(C)C1=C(OCC(=O)O)C(=CC(=C1)C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 2,4,6-triisopropylphenol (4.0 g, 18 mmol) in 50 mL tetrahydrofuran was added dropwise to a suspension of sodium hydride (1.52 g, 38 mmol) in 25 mL tetrahydrofuran. The resulting pale green suspension was stirred for 30 minutes before a solution of bromoacetic acid (2.52 g, 18 mmol) in 50 mL tetrahydrofura... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | O1CCCC1 | null | 16 | CC(C)c1cc(C(C)C)c(O)c(C(C)C)c1.O=C(O)CBr>O1CCCC1>CC(C)c1cc(C(C)C)c(OCC(=O)O)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3c4498248fcb4b01a4ddd90bff01e0d6 | CC(C)c1cc(C(C)C)c(OCC(=O)O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1cc(C(C)C)c(OCC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | CC(C)C1=C(C(=CC=C1)C(C)C)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C.C(C)(C)C1=C(C(=CC=C1)C(C)C)CC(=O)O.CC(C)C1=C(OCC(=O)O)C(=CC(=C1)C(C)C)C(C)C>>CC(C)C1=C(OCC(=O)C=2C(=C(C(=CC2)C(C)C)OS(N)(=O)=O)C(C)C)C(=CC(=C1)C(C)C)C(C)C | O=C(O)[CH2:12][O:11][c:10]1[c:6]([CH:7]([CH3:8])[CH3:9])[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:36][c:32]1[CH:33]([CH3:34])[CH3:35].CC(C)c1cccc(C(C)C)c1C[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[c:22]([O:23][S:24]([NH2:25])(=[O:26])=[O:27])[c:28]1[CH:29]([CH3:30])[CH3:31]>>[CH3:1][CH:2]([CH3:... | CC(C)c1cc(C(C)C)c(OCC(=O)O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)c1cc(C(C)C)c(OCC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 | null | null | null | C-C Coupling | OtherReaction | c4aefcd6aaf640ef3cd1efd20867bca20dd14111986777e1aec1c930d9ee8112 | 4e82d9c84fbd73776bc3be24ff6ef66af9927bef00daef7fdc5f3870cde64505 | O=C(COc1ccccc1)c1ccccc1 | C-C(-C)-c1:c:c:c:c(-C(-C)-C):c:1-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O-C(=O)-[CH2;D2;+0:6]-[#8:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:6]-[#8:7]-[c:8])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with [2,4,6-tris(1-methylethyl)phenoxy]acetic acid, mp 126°-128° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ether | Ketone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(OCC(=O)O)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1CC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C>>CC(C)c1cc(C(C)C)c(OCC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c90de5a21e584d9293ad7c521d8cc0db | CC(C)c1cc(C(C)C)c(OCC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1O>>CC(C)c1cccc(C(C)C)c1OCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | CC(C)C1=C(OCC(=O)C=2C(=C(C(=CC2)C(C)C)OS(N)(=O)=O)C(C)C)C(=CC(=C1)C(C)C)C(C)C.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)O.C(C)(C)C1=C(C(=CC=C1)C(C)C)O>>CC(C)C1=C(OCC(=O)C=2C(=C(C(=CC2)C(C)C)OS(N)(=O)=O)C(C)C)C(=CC=C1)C(C)C | CC(C)c1cc(C(C)C)[c:12]([O:13][CH2:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[c:24]([O:25][S:26]([NH2:27])(=[O:28])=[O:29])[c:30]2[CH:31]([CH3:32])[CH3:33])[c:8]([CH:9]([CH3:10])[CH3:11])c1.CC(C)c1c(O)[c:4]([CH:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6]... | CC(C)c1cc(C(C)C)c(OCC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1O | CC(C)c1cccc(C(C)C)c1OCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C | null | null | null | Miscellaneous | OtherReaction | 52c37c404715c2e00455f50f49a8ba9f76dbd7b2a47ae63c4ba064feafcb067f | 572181661086268a13b983224df961498cb5d227095f61722dfebbb3c0db87a1 | O=C(COc1ccccc1)c1ccccc1 | C-C(-C)-c1:[cH;D2;+0:1]:[c:2]:[c:3]:[c;H0;D3;+0:4](-[C:5](-[C;D1;H3:6])-[C;D1;H3:7]):c:1-O.C-C(-C)-c1:c:[c;H0;D3;+0:8](-[C:9](-[C;D1;H3:10])-[C;D1;H3:11]):[c;H0;D3;+0:12](-[#8:13]-[C:14]-[C:15]=[O;D1;H0:16]):c(-C(-C)-C):c:1>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])-[c;H0;D3;+0:8]1:[cH;D2;+0:1]:[c:2]:[c:3]:[c;H0;D3;+0:4](-[C:5... | null | [] | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 46, except that 2,4,6 - triisopropylphenol was replaced with 2,6-diisopropylphenol, mp 108°-110° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(OCC(=O)c2ccc(C(C)C)c(OS(N)(=O)=O)c2C(C)C)c(C(C)C)c1.CC(C)c1cccc(C(C)C)c1O>>CC(C)c1cccc(C(C)C)c1OCC(=O)c1ccc(C(C)C)c(OS(N)(=O)=O)c1C(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0a967e5e88454d92891b438873ad9c10 | N#CCBr.O=CC(c1ccccc1)c1ccccc1>>N#CCC(C=O)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(C=O)C1=CC=CC=C1.[H-].[Na+].BrCC#N>>C1(=CC=CC=C1)C(CC#N)(C=O)C1=CC=CC=C1 | Br[CH2:3][C:2]#[N:1].[CH:4]([CH:5]=[O:6])([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[N:1]#[C:2][CH2:3][C:4]([CH:5]=[O:6])([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | N#CCBr.O=CC(c1ccccc1)c1ccccc1 | N#CCC(C=O)(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | c0aac6eb308ce10cc64a9c0760acaf7c2314b63a36e8973be08decba508160c4 | d0010aaaebf375b0313372a9cac9506fb7ded9ab1b5a4461babbcb1ac1f9a08e | c1ccc(Cc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[O;D1;H0:4]=[C:5]-[CH;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:6](-[C:5]=[O;D1;H0:4])(-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | To a solution of diphenylacetoaldehyde (1 g) in tetrahydrofuran (10 ml) was added a suspension of 60% sodium hydride (0.25 g) in tetrahydrofuran (5 ml) carefully dropwise under ice-cooling and stirring. After completion of dropwise addition, the mixture was further stirred for 20 minutes. Then, bromoacetonitrile (0.41 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | Aldehyde | null | null | c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | null | N#CCBr.O=CC(c1ccccc1)c1ccccc1>O1CCCC1>N#CCC(C=O)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-559dde09b3ed44a1952c44f127de01bf | C=CC#N.O=CC(c1ccccc1)c1ccccc1>>N#CCCC(C=O)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(C=O)C1=CC=CC=C1.C(C=C)#N.N12CCCCCC2=NCCC1>>C1(=CC=CC=C1)C(CCC#N)(C=O)C1=CC=CC=C1 | [N:1]#[C:2][CH:3]=[CH2:4].[CH:5]([CH:6]=[O:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[N:1]#[C:2][CH2:3][CH2:4][C:5]([CH:6]=[O:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | C=CC#N.O=CC(c1ccccc1)c1ccccc1 | N#CCCC(C=O)(c1ccccc1)c1ccccc1 | null | null | C(C)(C)O | C-C Coupling | OtherReaction | 6ad2788b9ed96071c4729c9c54a7a5a8e6818443a6c9918e9c3abf718d348f7f | d7a27cd283d7e68f3118872bb42bca1ff19b94407028c02d8ce8f28c38464ed0 | c1ccc(Cc2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[O;D1;H0:5]=[C:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]>>[N;D1;H0:4]#[C:3]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:7](-[C:6]=[O;D1;H0:5])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13] | null | [] | 70 | CELSIUS | null | null | Diphenylacetaldehyde (25.6 g), acrylonitrile (12.5 ml), and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU:2.5 g) were stirred in isopropyl alcohol (250 ml) with warming at 70° C. for 6 hours. The reaction mixture was concentrated to dryness and the group was purified by silica gel column chromatography. The crude crystal cro... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Vinyl | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | C(C)(C)O | 70 | null | C=CC#N.O=CC(c1ccccc1)c1ccccc1>C(C)(C)O>N#CCCC(C=O)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e7d11e1675474553aba3f131664ab749 | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.N#CCC(C=O)(c1ccccc1)c1ccccc1>>CCOC(=O)C=CC(CC#N)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(CC#N)(C=O)C1=CC=CC=C1.C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)CC(C=CC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1 | c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1.O=[CH:7][C:8]([CH2:9][C:10]#[N:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][C:8]([CH2:9][C:10]#[N:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1... | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.N#CCC(C=O)(c1ccccc1)c1ccccc1 | CCOC(=O)C=CC(CC#N)(c1ccccc1)c1ccccc1 | null | null | C(Cl)(Cl)Cl | C-C Coupling | Wittig reaction with triphenylphosphorane | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(Cc2ccccc2)cc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])(-[c:4])-[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=[CH;D2;+0:1]-[C:2](-[C:3])(-[c:4])-[c:5] | 63.5 | [{"value": 63.5, "product": "C(#N)CC(C=CC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,3-Diphenyl-3-formylpropionitrile (0.85 g) and (carbethoxymethylene)triphenylphosphorane (1.46 g) were heated in chloroform (20 ml) on reflux for 7 hours. The reaction mixture was then concentrated to dryness and the group was purified by silica gel column chromatography to provide the title compound (0.7 g) as colorl... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.N#CCC(C=O)(c1ccccc1)c1ccccc1>C(Cl)(Cl)Cl>CCOC(=O)C=CC(CC#N)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-58636e593d6041a8ad292a9becfec4cf | Clc1ccccc1.N#CC(O)c1ccccc1>>N#CC(c1ccccc1)c1ccc(Cl)cc1 | C(C(O)C1=CC=CC=C1)#N.ClC1=CC=CC=C1.S(O)(O)(=O)=O>>ClC1=CC=C(C=C1)C(C#N)C1=CC=CC=C1 | [cH:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1.O[CH:3]([C:2]#[N:1])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[N:1]#[C:2][CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | Clc1ccccc1.N#CC(O)c1ccccc1 | N#CC(c1ccccc1)c1ccc(Cl)cc1 | null | null | null | C-C Coupling | OtherReaction | 353f6f3410bb939815e396d07868f2feb4b967c7c280d70099400ec8589322b5 | 7ccf8a4ec454d6cc03ce1e3efafa301b3c51d9e9635279e99312f4bc816939b8 | c1ccc(Cc2ccccc2)cc1 | O-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]>>[N;D1;H0:3]#[C:2]-[CH;D3;+0:1](-[c:4](:[c:5]):[c:6])-[c;H0;D3;+0:9](:[c:8]:[c:7]):[c:10]:[c:11] | 42.1 | [{"value": 42.1, "product": "ClC1=CC=C(C=C1)C(C#N)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a mixture of mandelonitrile (5 g) and chlorobenzene (15.7 g) was added sulfuric acid (9.8 ml) dropwise while the temperature of the mixture was maintained at 5°-10° C. After completion of dropwise addition, the mixture was stirred for another 1.5 hours. This reaction mixture was poured in ice-water and the syrup tha... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | 1.5 | Clc1ccccc1.N#CC(O)c1ccccc1>>N#CC(c1ccccc1)c1ccc(Cl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-45500bc5d2b740f7ad9d689e7536b18c | C=CC(=O)OCC.N#CC(c1ccccc1)c1ccccc1>>CCOC(=O)CCC(C#N)(c1ccccc1)c1ccccc1 | Cl.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1.C1CCC2=NCCCN2CC1.C(C=C)(=O)OCC>>C(#N)C(CCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[CH:8]([C:9]#[N:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8]([C:9]#[N:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | C=CC(=O)OCC.N#CC(c1ccccc1)c1ccccc1 | CCOC(=O)CCC(C#N)(c1ccccc1)c1ccccc1 | null | null | C(C)O | C-C Coupling | OtherReaction | 0dd663798644045f05735aa65d7d5f75deb9b4c6f9a5f9f12e7ba5a1fd833777 | 023be09df8c91ecd324bf8ccf8de227215e242fba7ad84123c19b6afa1463de0 | c1ccc(Cc2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[N;D1;H0:7]#[C:8]-[CH;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C;H0;D4;+0:9](-[C:8]#[N;D1;H0:7])(-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15] | null | [] | 80 | CELSIUS | 16 | HOUR | To a solution of diphenylacetonitrile (28 g) in ethanol (100 ml) were added DBU (6 ml) and ethyl acrylate (30 ml), and the mixture was heated and stirred at 80° C. for 16 hours. After cooling, 2N-hydrochloric acid (200 ml) was added and the mixture was extracted with isopropyl ether. The organic layer was washed with w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester | null | null | c1ccccc1.c1ccccc1 | null | C(C)O | 80 | 16 | C=CC(=O)OCC.N#CC(c1ccccc1)c1ccccc1>C(C)O>CCOC(=O)CCC(C#N)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-93d6f4d190a449699491ef1331779bbf | CCOC(=O)CCCBr.N#CC(c1ccccc1)c1ccccc1>>CCOC(=O)CCCC(C#N)(c1ccccc1)c1ccccc1 | BrCCCC(=O)OCC.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1.[H-].[Na+]>>C(#N)C(CCCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1 | Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH:9]([C:10]#[N:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][C:9]([C:10]#[N:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22]... | CCOC(=O)CCCBr.N#CC(c1ccccc1)c1ccccc1 | CCOC(=O)CCCC(C#N)(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(Cc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[N;D1;H0:7]#[C:8]-[CH;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:9](-[C:8]#[N;D1;H0:7])(-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15] | null | [] | null | null | 20 | MINUTE | To a stirring solution of diphenylacetonitrile (1-g) in tetrahydrofuran (10 ml) was added 60% sodium hydride (0.25 g) in small portions under ice-cooling. After completion of dropwise addition, the mixture was stirred for 20 minutes. Then, ethyl 4-bromobutyrate (0.94 ml) was added dropwise under ice-cooling and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | 0.333333 | CCOC(=O)CCCBr.N#CC(c1ccccc1)c1ccccc1>O1CCCC1>CCOC(=O)CCCC(C#N)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eaada865db324bc28dcbc45995d18d6d | CCOC(=O)C=CC(CC#N)(c1ccccc1)c1ccccc1>>CCOC(=O)CCC(CC#N)(c1ccccc1)c1ccccc1 | C(#N)CC(C=CC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)CC(CCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][C:8]([CH2:9][C:10]#[N:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C:8]([CH2:9][C:10]#[N:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:2... | CCOC(=O)C=CC(CC#N)(c1ccccc1)c1ccccc1 | CCOC(=O)CCC(CC#N)(c1ccccc1)c1ccccc1 | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc(Cc2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7](-[C:8])(-[c:9])-[c:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7](-[C:8])(-[c:9])-[c:10] | 85.2 | [{"value": 85.2, "product": "C(#N)CC(CCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 5-cyano-4,4-diphenyl-2-pentenoate (0.7 g) in ethanol (20 ml) was added 10% palladium-on-carbon (0.24 g), and the mixture was subjected to catalytic hydrogenation at atmospheric pressure and temperature. The catalyst in the reaction mixture was filtered off and the filtrate was concentrated to dry... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)O | null | null | CCOC(=O)C=CC(CC#N)(c1ccccc1)c1ccccc1>[Pd].C(C)O>CCOC(=O)CCC(CC#N)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cc804ed094964e088cdc53d7d375a905 | CCOC(=O)CCC(C#N)(c1ccccc1)c1ccccc1>>NCC(CCCO)(c1ccccc1)c1ccccc1 | C(#N)C(CCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>NCC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1 | CCO[C:6]([CH2:5][CH2:4][C:3]([C:2]#[N:1])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[O:7]>>[NH2:1][CH2:2][C:3]([CH2:4][CH2:5][CH2:6][OH:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CCOC(=O)CCC(C#N)(c1ccccc1)c1ccccc1 | NCC(CCCO)(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | Reduction | OtherReaction | 2e8ace5b6fedb2e54ca712aebb097c3ccaacb1aba06a689dfa332c1fa5ca663b | 9e7321559a8b8ba368a708f05d9c450b081c6d597670bad9a30dfe57b011f79f | c1ccc(Cc2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]-[C:5](-[c:6])(-[c:7])-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[NH2;D1;+0:9]-[CH2;D2;+0:8]-[C:5](-[c:6])(-[c:7])-[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 78.5 | [{"value": 78.5, "product": "NCC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | To a stirred solution of ethyl 4-cyano-4,4-diphenylbutyrate (1.2 g) in tetrahydrofuran (30 ml) was added lithium aluminum hydride (0.44 g) in small portion under ice-cooling. After completion of dropwise addition, the mixture was heated and stirred at 60° C. for 3 hours. The reaction mixture was then cooled with ice ag... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Primary alcohol.Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | 60 | 3 | CCOC(=O)CCC(C#N)(c1ccccc1)c1ccccc1>O1CCCC1>NCC(CCCO)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-11164e2e6e7e43489e2df2d0327da2ec | CC(=O)OC(C)=O.NCC(CCCO)(c1ccccc1)c1ccccc1>>O=CNCC(CCCO)(c1ccccc1)c1ccccc1 | NCC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OC(C)=O>>C(=O)NCC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1 | CC(=O)O[C:2](C)=[O:1].[NH2:3][CH2:4][C:5]([CH2:6][CH2:7][CH2:8][OH:9])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[CH:2][NH:3][CH2:4][C:5]([CH2:6][CH2:7][CH2:8][OH:9])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CC(=O)OC(C)=O.NCC(CCCO)(c1ccccc1)c1ccccc1 | O=CNCC(CCCO)(c1ccccc1)c1ccccc1 | null | null | C(=O)O | Acylation | OtherReaction | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(Cc2ccccc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[NH;D2;+0:5]-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | 4 | HOUR | In formic acid (80 ml) was dissolved 5-amino-4,4-diphenylpentanol (10 g) followed by addition of acetic anhydride (13 ml) and the mixture was stirred at room temperature for 4 hours. This reaction mixture was concentrated to dryness and the group was partitioned into chloroform and water. The water layer was made basic... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(=O)O | null | 4 | CC(=O)OC(C)=O.NCC(CCCO)(c1ccccc1)c1ccccc1>C(=O)O>O=CNCC(CCCO)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d9dc45b335d749a78c3c25428ee98f44 | CCOC(=O)CCC(CC#N)(c1ccccc1)c1ccccc1>>N#CCC(CCCO)(c1ccccc1)c1ccccc1 | C(#N)CC(CCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>C(#N)CC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1 | CCO[C:7]([CH2:6][CH2:5][C:4]([CH2:3][C:2]#[N:1])([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:8]>>[N:1]#[C:2][CH2:3][C:4]([CH2:5][CH2:6][CH2:7][OH:8])([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | CCOC(=O)CCC(CC#N)(c1ccccc1)c1ccccc1 | N#CCC(CCCO)(c1ccccc1)c1ccccc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Cc2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 75.3 | [{"value": 75.3, "product": "C(#N)CC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred solution of ethyl 5-cyano-4,4-diphenylpentanoate (2 g) in tetrahydrofuran (25 ml) was added lithium aluminum hydride (0.37 g) in small portions under ice-cooling. After completion of addition, the mixture was further stirred for 30 minutes. While the reaction mixture was stirred under ice-cooling, water (0... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | CCOC(=O)CCC(CC#N)(c1ccccc1)c1ccccc1>O1CCCC1>N#CCC(CCCO)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c3f6e8f485644f5ca4e7f158571808af | II.N#CCC(CCCO)(c1ccccc1)c1ccccc1>>N#CCC(CCCI)(c1ccccc1)c1ccccc1 | C(#N)CC(CCCO)(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.II>>C1(=CC=CC=C1)C(CC#N)(CCCI)C1=CC=CC=C1 | I[I:8].O[CH2:7][CH2:6][CH2:5][C:4]([CH2:3][C:2]#[N:1])([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[N:1]#[C:2][CH2:3][C:4]([CH2:5][CH2:6][CH2:7][I:8])([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | II.N#CCC(CCCO)(c1ccccc1)c1ccccc1 | N#CCC(CCCI)(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(Cc2ccccc2)cc1 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[I;H0;D1;+0:1] | 81.6 | [{"value": 81.6, "product": "C1(=CC=CC=C1)C(CC#N)(CCCI)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of triphenylphosphine (1.68 g) in methylene chloride (30 ml) and imidazole (0.44 g) was added iodine (1.62 g). To this mixture was added a solution of 5-cyano-4,4-diphenylpentanol (1.3 g) in methylene chloride (5 ml) dropwise. After completion of dropwise addition, the mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1ccccc1 | HI | C(Cl)Cl | null | 8 | II.N#CCC(CCCO)(c1ccccc1)c1ccccc1>C(Cl)Cl>N#CCC(CCCI)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c45ce467eda245a8a90c7c579be52209 | CCOC(=O)CCC(CCC#N)(c1ccccc1)c1ccccc1>>N#CCCC(CCC(=O)O)(c1ccccc1)c1ccccc1 | C(#N)CCC(CCC(=O)OCC)(C1=CC=CC=C1)C1=CC=CC=C1.[OH-].[Na+]>>C(#N)CCC(CCC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1 | CC[O:10][C:8]([CH2:7][CH2:6][C:5]([CH2:4][CH2:3][C:2]#[N:1])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)=[O:9]>>[N:1]#[C:2][CH2:3][CH2:4][C:5]([CH2:6][CH2:7][C:8](=[O:9])[OH:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CCOC(=O)CCC(CCC#N)(c1ccccc1)c1ccccc1 | N#CCCC(CCC(=O)O)(c1ccccc1)c1ccccc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 94.5 | [{"value": 94.5, "product": "C(#N)CCC(CCC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of ethyl 6-cyano-4,4-diphenylhexanoate (25.5 g) in ethanol (400 ml) was added 1N-aqueous sodium hydroxide solution (120 ml) and the mixture was heated and stirred at 60° C. for 1 hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the group was made aci... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | 60 | 1 | CCOC(=O)CCC(CCC#N)(c1ccccc1)c1ccccc1>C(C)O>N#CCCC(CCC(=O)O)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8cac3f5cbcd64aff969a030ee656e03d | COc1ccc2c(c1)CCC1(CCCCN1)C2.N#CCC(CCCI)(c1ccccc1)c1ccccc1>>COc1ccc2c(c1)CCC1(CCCCN1CCCC(CC#N)(c1ccccc1)c1ccccc1)C2 | C1(=CC=CC=C1)C(CC#N)(CCCI)C1=CC=CC=C1.Cl.COC=1C=C2CCC3(NCCCC3)CC2=CC1.C(C)N(CC)CC.C([O-])([O-])=O.[K+].[K+]>>Cl.COC=1C=C2CCC3(N(CCCC3)CCCC(CC#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][NH:16]1)[CH2:36]2.I[CH2:17][CH2:18][CH2:19][C:20]([CH2:21][C:22]#[N:23])([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C... | COc1ccc2c(c1)CCC1(CCCCN1)C2.N#CCC(CCCI)(c1ccccc1)c1ccccc1 | COc1ccc2c(c1)CCC1(CCCCN1CCCC(CC#N)(c1ccccc1)c1ccccc1)C2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e76537564b204757c56ea9f15d9563556e48d483b30b2e91436650a0999d405b | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C(CCCN2CCCCC23CCc2ccccc2C3)c2ccccc2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](-[C:6])(-[C:7])-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:4]-[C:5](-[C:6])(-[C:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9]-[C:10] | 34 | [{"value": 34.0, "product": "Cl.COC=1C=C2CCC3(N(CCCC3)CCCC(CC#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,3-Diphenyl-6-iodohexanenitrile (1.5 g), 3,4-dihydro-6-methoxyspiro[naphthalene-2(1H),2'-piperidine]hydrochloride (1.39 g), triethylamine (0.53 g), and potassium carbonate (0.72 g) were stirred in acetonitrile (25 ml) at 70° C. overnight. The insoluble matter in the reaction mixture was filtered off and the filtrate w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCC[NH]1)C2 | c1ccc2c(c1)CCC1(CCCC[NH]1)C2.c1ccccc1.c1ccccc1 | HI | C(C)#N | null | null | COc1ccc2c(c1)CCC1(CCCCN1)C2.N#CCC(CCCI)(c1ccccc1)c1ccccc1>C(C)#N>COc1ccc2c(c1)CCC1(CCCCN1CCCC(CC#N)(c1ccccc1)c1ccccc1)C2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-94dea17c11d546a38a349bc82e649588 | ICCc1ccccc1.N#CC1CCCCN1C(=O)c1ccccc1>>N#CC1(CCc2ccccc2)CCCCN1C(=O)c1ccccc1 | C(C)(C)[N-]C(C)C.[Li+].C(C1=CC=CC=C1)(=O)N1C(CCCC1)C#N.C(CC1=CC=CC=C1)I>>C(C1=CC=CC=C1)(=O)N1C(CCCC1)(C#N)CCC1=CC=CC=C1 | I[CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[N:1]#[C:2][CH:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[N:1]#[C:2][C:3]1([CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:17](=[O:18])[c:19]1[cH:20][cH:21][... | ICCc1ccccc1.N#CC1CCCCN1C(=O)c1ccccc1 | N#CC1(CCc2ccccc2)CCCCN1C(=O)c1ccccc1 | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | 065782c188f5a2ceb233aebe918fea20e0b11b0731bb1fe7f5a07eb4dfd9cf38 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=C(c1ccccc1)N1CCCCC1CCc1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[CH;D3;+0:6](-[C:7]#[N;D1;H0:8])-[#7:9](-[C:10](=[O;D1;H0:11])-[c:12])-[C:13]>>[C:4]-[C:5]-[C;H0;D4;+0:6](-[C:7]#[N;D1;H0:8])(-[CH2;D2;+0:1]-[C:2]-[c:3])-[#7:9](-[C:10](=[O;D1;H0:11])-[c:12])-[C:13] | null | [] | 0 | CELSIUS | 30 | MINUTE | To 200 ml of a solution of lithium diisopropylamide (140 mmol) in tetrahydrofuran was added 15 g of solid 1-benzoyl-2-piperidinecarbonitrile at -78° C. and the mixture was stirred for 30 minutes. Then, 100 ml of a solution of 33.2 g of phenethyl iodide in tetrahydrofuran was added dropwise at -78° C. After completion o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HI | O1CCCC1.O | 0 | 0.5 | ICCc1ccccc1.N#CC1CCCCN1C(=O)c1ccccc1>O1CCCC1.O>N#CC1(CCc2ccccc2)CCCCN1C(=O)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-44fe0f9082374e0698078619b2803762 | N#CC1(CCc2ccccc2)CCCCN1C(=O)c1ccccc1.[Cl-]>>Cl.O=C1c2ccccc2CCC12CCCCN2 | [Cl-].[Al+3].[Cl-].[Cl-].C(C1=CC=CC=C1)(=O)N1C(CCCC1)(C#N)CCC1=CC=CC=C1.[OH-].[Na+]>>Cl.N1C2(CCCC1)C(C1=CC=CC=C1CC2)=O | N#[C:3][C:12]1([CH2:11][CH2:10][c:9]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1C(c1ccccc1)=[O:2].[Cl-:1]>>[ClH:1].[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10][CH2:11][C:12]12[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]2 | N#CC1(CCc2ccccc2)CCCCN1C(=O)c1ccccc1.[Cl-] | Cl.O=C1c2ccccc2CCC12CCCCN2 | null | null | ClCCCl | C-C Coupling | OtherReaction | 23ced2ae8f1bf65d2a9cc880b25773b448f36823374393ce0466fa5dfed9edfe | 5188a30dd54d4fbf48b01bbe3063a817b33c3e7b24a4df48d49add2503a98e95 | O=C1c2ccccc2CCC12CCCCN2 | N#[C;H0;D2;+0:1]-[C:2](-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])(-[C:10])-[N;H0;D3;+0:11](-C(=[O;H0;D1;+0:12])-c1:c:c:c:c:c:1)-[C:13]-[C:14].[Cl-;H0;D0:15]>>[C:10]-[C:2]1(-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9])-[C;H0;D3;+0:1]-1=[O;H0;D1;+0:12])-[NH;D2;+0:11]-[C:13]-[C:14].[ClH;D0;+0:15] | null | [] | null | null | null | null | In 250 ml of 1,2-dichloroethane was dissolved 7.64 g of 1-benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile. To this solution was added 8.0 g of aluminum chloride and the mixture was refluxed for 6 hours. The reaction mixture was then cooled and poured cautiously into 10% aqueous sodium hydroxide and extracted with me... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary amide | Ketone.Secondary amine | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccc2c(c1)CCC1(CCCCN1)C2 | c1ccc2c(c1)CCC1(CCCCN1)C2 | Other | ClCCCl | null | null | N#CC1(CCc2ccccc2)CCCCN1C(=O)c1ccccc1.[Cl-]>ClCCCl>Cl.O=C1c2ccccc2CCC12CCCCN2 |
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