|
【结 构 式】 
|
【分子编号】39111 【品名】(4-Hydroxyphenyl)[2-(4-methoxyphenyl)-3,4-dihydro-1-naphthalenyl]methanone; 3,4-Dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-hydroxyphenyl ketone 【CA登记号】 |
【 分 子 式 】C24H20O3 【 分 子 量 】356.421 【元素组成】C 80.88% H 5.66% O 13.47% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation beta-tetralone (I) with phenyl 4-methoxybenzoate (II) by means of NaNH2 in THF gives 3,4-dihydro-1-(4-methoxybenzoyl)-2(1H)-naphthalenone (III), which is then submitted to a Grignard reaction with 4-methoxyphenylmagnesium bromide (IV) in hot THF yielding 3,4-dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-methoxyphenyl ketone (V). The cleavage of one methoxy group of (V) with sodium ethylmercaptide (A) in dry DMF affords 3,4-dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-hydroxyphenyl ketone (VI), which is finally condensed with N-(2-chloroethyl)pyrrolidine (VII) by means of K2CO3 in refluxing 2-butanone.
| 【1】 Jones, C.D.; et al.; Synthesis and antiestrogenic activity of [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)ethoxyphenyl]methanone]methane sulfonic acid salt. J Med Chem 1979, 22, 8, 962-966. |
| 【2】 Castaner, J.; Hillier, K.; Trioxifene mesylate. Drugs Fut 1980, 5, 5, 259. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 39110 | Sodium 1-ethanethiolate; Sodium ethylmercaptide | 811-51-8 | C2H5NaS | 详情 | 详情 |
| (I) | 39106 | 3,4-Dihydro-2(1H)-naphthalenone; beta-Tetralone | 530-93-8 | C10H10O | 详情 | 详情 |
| (II) | 39107 | Phenyl 4-methoxybenzoate | C14H12O3 | 详情 | 详情 | |
| (III) | 39108 | 1-(4-Methoxybenzoyl)-3,4-dihydro-2(1H)-naphthalenone; 3,4-Dihydro-1-(4-methoxybenzoyl)-2(1H)-naphthalenone | C18H16O3 | 详情 | 详情 | |
| (IV) | 37674 | Bromo(4-methoxyphenyl)magnesium; 4-Methoxyphenylmagnesium bromide | 352-13-6 | C7H7BrMgO | 详情 | 详情 |
| (V) | 39109 | (4-Methoxyphenyl)[2-(4-methoxyphenyl)-3,4-dihydro-1-naphthalenyl]methanone; 3,4-Dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-methoxyphenyl ketone | C25H22O3 | 详情 | 详情 | |
| (VI) | 39111 | (4-Hydroxyphenyl)[2-(4-methoxyphenyl)-3,4-dihydro-1-naphthalenyl]methanone; 3,4-Dihydro-2-(4-methoxyphenyl)-1-naphthyl-4-hydroxyphenyl ketone | C24H20O3 | 详情 | 详情 | |
| (VII) | 33922 | 1-(2-Chloroethyl)pyrrolidine; N-(2-Chloroethyl)pyrrolidine | C6H12ClN | 详情 | 详情 |