Cioteronel, X-Andron, Cyoctol, CPC-10997, Cyoctol
塞奥罗奈Chemical Name: (?-2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one; (?-4-(5-Methoxyheptyl)hexahydro-2(1H)-pentalenone
CAS No. 89672-11-7 (undefined stereoch.)
项目整合开发状态: Phase III
项目研究机构: Chantal (Originator), Chi-Fu Trading (Licensee), Kolon Industries (Licensee), Leca (Licensee)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Cycloaliphatic pharmaceutical cpds.
文献作者:Kasha,W.J.(CBD Corp.)
参考来源:DE 3378265; EP 0107733; WO 8304019
📄 详细内容
合成路线: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.
参考文献标题:Cyoctol
文献作者:Castar,R.M.; Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1987,12(11),1012
产品链接: CAS No. 89672-11-7››