Cioteronel, X-Andron, Cyoctol, CPC-10997, Cyoctol-药物合成数据库

【药物名称】Cioteronel, X-Andron, Cyoctol, CPC-10997, Cyoctol

化学结构式(Chemical Structure):

参考文献No.	38876
标题:	Cycloaliphatic pharmaceutical cpds.
作者:	Kasha, W.J. (CBD Corp.)
来源:	DE 3378265; EP 0107733; WO 8304019

合成路线图解说明: The reaction of 5-methoxyheptyl chloride (I) with magnesium in THF gives the corresponding Grignard reagent (II), which is condensed with 3-chlorocyclopentene (III) in refluxing THF to yield 3-(5-methoxy-1-heptyl)cyclopentene (IV). The cyclization of (IV) with dichloroacetyl chloride (V) by means of triethylamine in refluxing hexane affords 2-(5-methoxy-1-heptyl)-6,6-dichlorobicyclo[3.2.0]heptan-7-one (VI), which is submitted to a ring expansion with diazometane in ether giving 2-(5-methoxy-1-heptyl-6,6-dichlorobicyclo[3.3.0]octan-7-one (VII). Finally, this compound is dechlorinated with Zn in acetic acid.

参考文献No.	79465
标题:	Cyoctol
作者:	Casta馿r, R.M.; Casta馿r, J.; Serradell, M.N.
来源:	Drugs Fut 1987,12(11),1012

合成路线图解说明: The reaction of 5-methoxyheptyl chloride (I) with magnesium in THF gives the corresponding Grignard reagent (II), which is condensed with 3-chlorocyclopentene (III) in refluxing THF to yield 3-(5-methoxy-1-heptyl)cyclopentene (IV). The cyclization of (IV) with dichloroacetyl chloride (V) by means of triethylamine in refluxing hexane affords 2-(5-methoxy-1-heptyl)-6,6-dichlorobicyclo[3.2.0]heptan-7-one (VI), which is submitted to a ring expansion with diazometane in ether giving 2-(5-methoxy-1-heptyl-6,6-dichlorobicyclo[3.3.0]octan-7-one (VII). Finally, this compound is dechlorinated with Zn in acetic acid.