2-((3S,5S,8R,9S,10S,13S,14S,17R)-10,13-dimethyl-3-(triisopropylsilyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propan-1-ol | 1298132-53-2

• 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: 2-((3S,5S,8R,9S,10S,13S,14S,17R)-10,13-dimethyl-3-(triisopropylsilyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propan-1-ol
• 英文别名: 2-[(3S,5S,8R,9S,10S,13S,14S,17R)-10,13-dimethyl-3-tri(propan-2-yl)silyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-ol
• CAS: 1298132-53-2
• 化学式: C₃₁H₅₈O₂Si
• 分子量: 490.886
• InChiKey: UYGFTYGBRAXONT-HCDPPBQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (((3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-(prop-1-en-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)triisopropylsilane 在 palladium 10% on activated carbon 、 氢气 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 生成 2-((3S,5S,8R,9S,10S,13S,14S,17R)-10,13-dimethyl-3-(triisopropylsilyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propan-1-ol
  参考文献：
  名称：

  Regioselective Semihydrogenation of Dienes

  摘要：

  A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.

  DOI：

  10.1021/jo200262r

文献信息

• Regioselective Semihydrogenation of Dienes
  作者：Thomas J. A. Graham、Thomas H. Poole、Charles N. Reese、Brian C. Goess

  DOI：10.1021/jo200262r

  日期：2011.5.20

  A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.