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【结 构 式】 
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【分子编号】29835 【品名】2-([4-[2-(cyclopropylmethoxy)ethoxy]phenoxy]methyl)oxirane; 4-[2-(cyclopropylmethoxy)ethoxy]phenyl 2-oxiranylmethyl ether 【CA登记号】 |
【 分 子 式 】C15H20O4 【 分 子 量 】264.3214 【元素组成】C 68.16% H 7.63% O 24.21% |
合成路线1
该中间体在本合成路线中的序号：(VI)The alkylation of 4-benzyloxyphenol (I) with 2-(cyclopropylmethoxy)ethyl mesylate (II) by means of NaOCH3 in refluxing methanol gives 4-[2-(cyclopropylmethoxy)-1-ethoxy]phenylmethoxybenzene (III), which is debenzylated by hydrogenolysis with H2 over PdC in methanol yielding 4-[2-(cyclopropylmethoxy)-1-ethoxy]phenol (IV). The treatment of (IV) with epichlorohydrin (V) in aqueous NaOH affords 1-[4-[2-(cyclopropylmethoxy)ethoxyphenoxy]-2,3-epoxy]propane (VI). Finally, this compound is treated with an excess of isopropylamine at room temperature to yield cicloprolol.
| 【1】 Leclerc, G.; Cicloprolol Hydrocloride. Drugs Fut 1985, 10, 12, 975. |
| 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) | 29332 | (6E,10E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acid | C20H34O2 | 详情 | 详情 | |
| (II) | 18956 | 4-(Benzyloxy)phenol; 4-Benzyloxyphenol | 103-16-2 | C13H12O2 | 详情 | 详情 |
| (III) | 29833 | benzyl 4-[2-(cyclopropylmethoxy)ethoxy]phenyl ether; 1-(benzyloxy)-4-[2-(cyclopropylmethoxy)ethoxy]benzene | C19H22O3 | 详情 | 详情 | |
| (IV) | 29834 | 4-[2-(cyclopropylmethoxy)ethoxy]phenol | C12H16O3 | 详情 | 详情 | |
| (V) | 29776 | 1-(chloromethyl)cyclopropane | 5911-08-0 | C4H7Cl | 详情 | 详情 |
| (VI) | 29835 | 2-([4-[2-(cyclopropylmethoxy)ethoxy]phenoxy]methyl)oxirane; 4-[2-(cyclopropylmethoxy)ethoxy]phenyl 2-oxiranylmethyl ether | C15H20O4 | 详情 | 详情 |