(5S,8S,9S,10S,11R,13S,14S,17S)-17-acetyl-11-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one | 1071422-97-3

• 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: (5S,8S,9S,10S,11R,13S,14S,17S)-17-acetyl-11-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
• CAS: 1071422-97-3
• 化学式: C₂₇H₄₆O₃Si
• 分子量: 446.746
• InChiKey: YCXINLLYESPUSL-OVZYZVFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S,8S,9S,10S,11R,13S,14S,17S)-17-acetyl-11-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3S,5S,8S,9S,10S,11R,13S,14S,17S)-11-((tert-butyldimethylsilyl)oxy)-17-((S)-1-hydroxyethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  Microwave assisted preparation of C(1)–C(11) oxygen-bridged pregnanes

  摘要：

  1,11-Epoxysteroids may be obtained by an intramolecular remote functionalization using Suarez reagent (diacetoxyiodobenzene/I-2) and irradiation with visible light. We have found that photolysis with visible light may be advantageously replaced by microwave irradiation to prepare 1,11-oxygen bridges resulting in higher yields and shorter reaction times especially in the case of sensitive substrates. Both methodologies were compared on a set of representative 11-alpha-hydroxypregnanes (3, 8, 10 and 11). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.07.016
• 作为产物：
  描述：

  11alpha-羟基-5alpha-孕甾烷-3,20-二酮 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到(5S,8S,9S,10S,11R,13S,14S,17S)-17-acetyl-11-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Microwave assisted preparation of C(1)–C(11) oxygen-bridged pregnanes

  摘要：

  1,11-Epoxysteroids may be obtained by an intramolecular remote functionalization using Suarez reagent (diacetoxyiodobenzene/I-2) and irradiation with visible light. We have found that photolysis with visible light may be advantageously replaced by microwave irradiation to prepare 1,11-oxygen bridges resulting in higher yields and shorter reaction times especially in the case of sensitive substrates. Both methodologies were compared on a set of representative 11-alpha-hydroxypregnanes (3, 8, 10 and 11). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.07.016