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【结 构 式】 
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【药物名称】Bifluranol, BX-341 【化学名称】erythro-4,4'-(1-Ethyl-2-methylethylene)bis[2-fluorophenol] 【CA登记号】34633-34-6 【 分 子 式 】C17H18F2O2 【 分 子 量 】292.32861 |
【开发单位】Biorex Laboratories (Originator) 【药理作用】ONCOLYTIC DRUGS, Antiandrogens |
合成路线1
This compound can be prepared in two different ways: 1) The condensation of 3-chloro-2-pentanone (I) with 2-fluoroanisole (II) by means of concentrated H2SO4 and subsequent heating at 240 C gives 2,3-bis(3-fluoro-4-methoxyphenyl)-2-pentene (III), which is reduced with H2 over Pd/C in anhydrous AcOH to afford 2,3-bis(3-fluoro-4-methoxyphenyl)pentane (IV). Finally, this compound is demethylated by treatment with refluxing aqueous HBr. 2) The Friedel-Kraft's condensation of (II) with 3-chloro-2-pentanol by means of AlCl3 also gives (IV).
| 【1】 Turner, J.C.; Chan, R.P.-K.; US 4051263 . |
| 【2】 Castaner, J.; Hopkins, S.J.; Bifluranol. Drugs Fut 1981, 6, 9, 531. |
| 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) | 37585 | 3-chloro-2-pentanone | C5H9ClO | 详情 | 详情 | |
| (II) | 37586 | 2-fluoroanisole; 1-fluoro-2-methoxybenzene; 2-fluorophenyl methyl ether | 321-28-8 | C7H7FO | 详情 | 详情 |
| (III) | 37587 | 4-[(E)-1-ethyl-2-(3-fluoro-4-methoxyphenyl)-1-propenyl]-2-fluorophenyl methyl ether; 4-[(E)-1-ethyl-2-(3-fluoro-4-methoxyphenyl)-1-propenyl]-2-fluoro-1-methoxybenzene | C19H20F2O2 | 详情 | 详情 | |
| (IV) | 37588 | 4-[1-ethyl-2-(3-fluoro-4-methoxyphenyl)propyl]-2-fluorophenyl methyl ether; 4-[1-ethyl-2-(3-fluoro-4-methoxyphenyl)propyl]-2-fluoro-1-methoxybenzene | C19H22F2O2 | 详情 | 详情 | |
| (V) | 37589 | 3-chloro-2-pentanol | C5H11ClO | 详情 | 详情 |