• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】18719

【品名】3-Methoxy-5-(1-naphthyl)-1-octyl-2-cyclohexen-1-ol bromomagnesium salt

【CA登记号】

【 分 子 式 】C25H33BrMgO2

【 分 子 量 】469.74482

【元素组成】C 63.92% H 7.08% Br 17.01% Mg 5.17% O 6.81%

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)

Treatment of 5-(1-naphthyl)cyclohexane-1,3-dione (I) with 2,2-dimethoxypropane and MeOH in the presence of p-toluenesulfonic acid provided enol ether (II). Condensation of (II) with n-octylmagnesium bromide in cold THF, followed by acidic treatment of intermediate (III) yielded enone (IV). The subsequent oxidative cleavage of (IV) with NaIO4 and a catalytic amount of ruthenium oxide gave ketoacid (V), which was converted into the oxime (VI) on treatment with hydroxylamine. Reduction of oxime (VI) with NaBH4 in AcOH gave the hydroxylamine (VII). Then, cyclization to the piperidone acid in the presence of silica gel in refluxing benzene, followed by chromatographic separation of the cis isomer, provided the target compound.

1 Honn, K.V.; Johnson, C.R.; Chen, Y.-F.; Shimoji, K.; Marnett, L.J. (Vanderbilt University; Wayne State University); Cyclic hydroxamic acids. US 5234933; WO 9308803 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10722 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane 77-76-9 C5H12O2 详情 详情
(I) 18717 3-hydroxy-5-(1-naphthyl)-2-cyclohexen-1-one C16H14O2 详情 详情
(II) 18718 3-methoxy-5-(1-naphthyl)-2-cyclohexen-1-one C17H16O2 详情 详情
(III) 18719 3-Methoxy-5-(1-naphthyl)-1-octyl-2-cyclohexen-1-ol bromomagnesium salt C25H33BrMgO2 详情 详情
(IV) 18720 5-(1-naphthyl)-3-octyl-2-cyclohexen-1-one C24H30O 详情 详情
(V) 18721 3-(1-naphthyl)-5-oxotridecanoic acid C23H30O3 详情 详情
(VI) 18722 5-(hydroxyimino)-3-(1-naphthyl)tridecanoic acid C23H31NO3 详情 详情
(VII) 18723 5-(hydroxyamino)-3-(1-naphthyl)tridecanoic acid C23H33NO3 详情 详情
Extended Information