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【结 构 式】 
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【药物名称】Cioteronel, X-Andron, Cyoctol, CPC-10997, Cyoctol 【化学名称】(±)-2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one 【CA登记号】89672-11-7 (undefined stereoch.) 【 分 子 式 】C16H28O2 【 分 子 量 】252.40036 |
【开发单位】Chantal (Originator), Chi-Fu Trading (Licensee), Kolon Industries (Licensee), Leca (Licensee) 【药理作用】Acne Therapy, DERMATOLOGIC DRUGS, ONCOLYTIC DRUGS, Antiandrogens |
合成路线1
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.
| 【1】 Kasha, W.J. (CBD Corp.); Cycloaliphatic pharmaceutical cpds.. DE 3378265; EP 0107733; WO 8304019 . |
| 【2】 Castaner, R.M.; Castaner, J.; Serradell, M.N.; Cyoctol. Drugs Fut 1987, 12, 11, 1012. |
| 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) | 19539 | 1-chloro-5-methoxyheptane; 5-chloro-1-ethylpentyl methyl ether | C8H17ClO | 详情 | 详情 | |
| (II) | 19540 | chloro(5-methoxyheptyl)magnesium | C8H17ClMgO | 详情 | 详情 | |
| (III) | 19541 | 3-chloro-1-cyclopentene | C5H7Cl | 详情 | 详情 | |
| (IV) | 19542 | 5-(2-cyclopenten-1-yl)-1-ethylpentyl methyl ether; 3-(5-methoxyheptyl)-1-cyclopentene | C13H24O | 详情 | 详情 | |
| (V) | 17829 | 2,2-dichloroacetyl chloride; dichloroacetyl chloride | 79-36-7 | C2HCl3O | 详情 | 详情 |
| (VI) | 19544 | 7,7-dichloro-4-(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one | C15H24Cl2O2 | 详情 | 详情 | |
| (VII) | 19545 | 1,1-dichloro-4-(5-methoxyheptyl)hexahydro-2(1H)-pentalenone | C16H26Cl2O2 | 详情 | 详情 |