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【结 构 式】 
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【分子编号】30580 【品名】(E)-4-(3,4-dichlorophenyl)-4-phenyl-3-butenoic acid 【CA登记号】 |
【 分 子 式 】C16H12Cl2O2 【 分 子 量 】307.17548 【元素组成】C 62.56% H 3.94% Cl 23.08% O 10.42% |
合成路线1
该中间体在本合成路线中的序号：(VI)The Friedel-Kraft's reaction of benzene (I) and 3,4-dichlorobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3,4-dichlorobenzophenone (III), which is condensed with diethyl succinate (IV) by means of potassium tert-butoxide in tert-butyl alcohol yielding ethyl 3-ethoxycarbonyl-4-(3,4-dichlorophenyl)-4-phenylbut-3-enoate (V). Hydrolysis of (V) with HBr in refluxing acetic acid affords 4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid (VI), which is hydrogenated with H2 over Pd/C in ethyl acetate giving 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid (VII), which is converted into the corresponding acyl chloride (VIII) with refluxing SOCl2. Cyclization of (VIII) with AlCl3 in CS2 yields 4-(3,4-dichlorophenyl)-3,4-dihydro-1-(2H)-naphthalenone (IX), which is treated with methylamine and TiCl4 in THF affording the corresponding Schiff base (X). Finally, this compound is reduced with H2 over Pd/C in THF.
| 【1】 Kraska, A.R.; Welch, W.M. Jr.; Koe, B.K.; Harbert, C.A. (Pfizer Inc.); Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphtalenamine. EP 0030081; JP 1981086137; US 4536518 . |
| 【2】 Castaner, J.; Serradell, M.N.; Sertraline. Drugs Fut 1984, 9, 4, 277. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 13364 | Benzene | 71-43-2 | C6H6 | 详情 | 详情 |
| (II) | 26356 | 3,4-dichlorobenzoyl chloride | 3024-72-4 | C7H3Cl3O | 详情 | 详情 |
| (III) | 30578 | (3,4-dichlorophenyl)(phenyl)methanone | 6284-79-3 | C13H8Cl2O | 详情 | 详情 |
| (IV) | 12313 | diethyl succinate | 123-25-1 | C8H14O4 | 详情 | 详情 |
| (V) | 30579 | diethyl 2-[(Z)-(3,4-dichlorophenyl)(phenyl)methylidene]succinate | C21H20Cl2O4 | 详情 | 详情 | |
| (VI) | 30580 | (E)-4-(3,4-dichlorophenyl)-4-phenyl-3-butenoic acid | C16H12Cl2O2 | 详情 | 详情 | |
| (VII) | 30581 | 4-(3,4-dichlorophenyl)-4-phenylbutyric acid | C16H14Cl2O2 | 详情 | 详情 | |
| (VIII) | 30582 | 4-(3,4-dichlorophenyl)-4-phenylbutanoyl chloride | C16H13Cl3O | 详情 | 详情 | |
| (IX) | 30583 | 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone; 4-(3',4'-Dichlorophenyl)-1-tetralone | 79580-19-3 | C16H12Cl2O | 详情 | 详情 |
| (X) | 30584 | N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-N-methylamine; N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine | C17H15Cl2N | 详情 | 详情 |