7α-methyl-4-cholesten-3-one | 64305-64-2

• 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: 7α-methyl-4-cholesten-3-one
• 英文别名: (7R,8S,9S,10R,13R,14S,17R)-7,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 64305-64-2
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: MZANIZZWZOMIRD-KBCVDXQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙二醇 、 7α-methyl-4-cholesten-3-one 在 对甲苯磺酸 作用下， 反应 3.5h， 以80 mg的产率得到
  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：

  (3S,7S,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113 mg的产率得到7α-methyl-4-cholesten-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

文献信息

• Process for the preparation of 4-androstene-3,17-dione derivatives
  申请人：Schering Aktiengesellschaft

  公开号：US04100027A1

  公开（公告）日：1978-07-11

  A process for the preparation of 4-androstene-3,17-dione derivatives of the formula ##STR1## wherein X is 6,7-methylene or fluoro, chloro, or methyl in the 6- or 7-position, comprises fermenting a sterol of the formula ##STR2## wherein X is as above and R.sub.1 is a hydrocarbon residue of 8-10 carbon atoms with a microorganism culture capable of degrading the side chain of a sterol.

  一种制备4-雄烯-3,17-二酮衍生物的方法，其化学式为##STR1##其中X为6,7-亚甲基或6-位或7-位为氟、氯或甲基，包括利用一种能降解甾醇侧链的微生物培养物发酵具有化学式##STR2##其中X如上所述，R.sub.1为8-10个碳原子的烃基残基。
• US4100027A
  申请人：——

  公开号：US4100027A

  公开（公告）日：1978-07-11
• 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.