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【结 构 式】

【分子编号】29833

【品名】benzyl 4-[2-(cyclopropylmethoxy)ethoxy]phenyl ether; 1-(benzyloxy)-4-[2-(cyclopropylmethoxy)ethoxy]benzene

【CA登记号】

【 分 子 式 】C19H22O3

【 分 子 量 】298.38188

【元素组成】C 76.48% H 7.43% O 16.09%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

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
Extended Information