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【结 构 式】

【分子编号】19545

【品名】1,1-dichloro-4-(5-methoxyheptyl)hexahydro-2(1H)-pentalenone

【CA登记号】

【 分 子 式 】C16H26Cl2O2

【 分 子 量 】321.28664

【元素组成】C 59.81% H 8.16% Cl 22.07% O 9.96%

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:(VII)

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
Extended Information