(3S,7R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | 96443-02-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3S,7R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 英文别名: (3S,7R,8S,9S,10R,13R,14S,17R)-7,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 96443-02-6
• 化学式: C₂₈H₄₈O
• 分子量: 400.689
• InChiKey: XHOOXFKEWFALGT-QCLFCMPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,7R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 在 环己酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以81%的产率得到7β-methyl-cholest-4-en-3-one
  参考文献：
  名称：

  Preparation of 7α- and 7β-methylcholestane derivatives by kinetic separation of the diastereomeric mixture

  摘要：

  7 alpha- and 7 beta-Methyl derivatives of cholest-5-en-3 beta-ol (cholesterol), cholest-4-en-3-one and cholest-4-en-3,6-dione were prepared. Methylation of 3 alpha, 5-cyclo-5 alpha-cholestan-6-one at C-7 was followed by stereoselective reduction with LiAlH4. The key transformation was cycloreversion of the mixture of 7 alpha-methyl-3 alpha, 5-cyclo-5 alpha-cholestan-6 alpha-ol and 7 beta-methyl-3 alpha, 5-cyclo-5 alpha-cholestan-6 beta-ol. The reaction of the latter was much faster under the standard conditions enabling easy separation of the C-7 isomers. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00131-1
• 作为产物：
  描述：

  5-胆甾烯-3β-醇-7-酮 在 Wilkinson's catalyst 氢气 、 sodium hydride 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 生成 (3S,7R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  A stereoselective synthesis of 7β-phenyl and 7β-methylcholesterol

  摘要：

  A stereoselective synthesis of 7beta-phenylcholesterol and 7beta-methylcholesterol is described.Cholesterol is an immensely important biological molecule. Its biosynthesis,1 conversion to steroid hormones2,3 and even its intracellular esterification4 (cholesterol acyltransferase, ACAT) form important areas of research. Cholesterol is metabolized in the body to bile acids in which the rate limiting step is the conversion of cholesterol to 7alpha-hydroxycholesterol by the enzyme 7alpha-hydroxylase. 5 Substituents of cholesterol at the 7 position should metabolically stabilize the molecule. 7Alpha-substituted steroids are conveniently prepared and have shown interesting antiprogestational,6 antiestrogen,7 antiandrogen,8 aldosterone antagonist9 and aromatase8 inhibitory activities. Chemistry for the stereoselective synthesis of 7beta-substituted steroids is relatively less developed.10 In this paper, we report a new stereoselective synthesis of 7beta-phenyl and 7beta-methylcholesterol. Chemistry described here should be applicable to the preparation of other 7beta-substituted steroids.

  DOI：

  10.1016/s0040-4039(00)60344-1

文献信息

• A stereoselective synthesis of 7β-phenyl and 7β-methylcholesterol
  作者：Raman K. Bakshi、Gary H. Rasmusson

  DOI：10.1016/s0040-4039(00)60344-1

  日期：1993.3

  A stereoselective synthesis of 7beta-phenylcholesterol and 7beta-methylcholesterol is described.Cholesterol is an immensely important biological molecule. Its biosynthesis,1 conversion to steroid hormones2,3 and even its intracellular esterification4 (cholesterol acyltransferase, ACAT) form important areas of research. Cholesterol is metabolized in the body to bile acids in which the rate limiting step is the conversion of cholesterol to 7alpha-hydroxycholesterol by the enzyme 7alpha-hydroxylase. 5 Substituents of cholesterol at the 7 position should metabolically stabilize the molecule. 7Alpha-substituted steroids are conveniently prepared and have shown interesting antiprogestational,6 antiestrogen,7 antiandrogen,8 aldosterone antagonist9 and aromatase8 inhibitory activities. Chemistry for the stereoselective synthesis of 7beta-substituted steroids is relatively less developed.10 In this paper, we report a new stereoselective synthesis of 7beta-phenyl and 7beta-methylcholesterol. Chemistry described here should be applicable to the preparation of other 7beta-substituted steroids.
• Preparation of 7α- and 7β-methylcholestane derivatives by kinetic separation of the diastereomeric mixture
  作者：Zenon Łotowski、Jacek W. Morzycki、Rafał R. Siciński

  DOI：10.1016/s0957-4166(98)00131-1

  日期：1998.5

  7 alpha- and 7 beta-Methyl derivatives of cholest-5-en-3 beta-ol (cholesterol), cholest-4-en-3-one and cholest-4-en-3,6-dione were prepared. Methylation of 3 alpha, 5-cyclo-5 alpha-cholestan-6-one at C-7 was followed by stereoselective reduction with LiAlH4. The key transformation was cycloreversion of the mixture of 7 alpha-methyl-3 alpha, 5-cyclo-5 alpha-cholestan-6 alpha-ol and 7 beta-methyl-3 alpha, 5-cyclo-5 alpha-cholestan-6 beta-ol. The reaction of the latter was much faster under the standard conditions enabling easy separation of the C-7 isomers. (C) 1998 Elsevier Science Ltd, All rights reserved.