(8R,9S,10S,13S,14S,17S)-17-Methoxymethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one | 132617-24-4

• 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: (8R,9S,10S,13S,14S,17S)-17-Methoxymethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
• 英文别名: (8R,9S,10S,13S,14S,17S)-17-(methoxymethoxy)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 132617-24-4
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: NIKXNNOMGOIMAM-AEBCAVJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,10S,13S,14S,17S)-17-Methoxymethoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 17β-(methoxymethoxy)androstane-3β-carbonitrile
  参考文献：
  名称：

  Cyano phosphate: an efficient intermediate for the chemoselective conversion of carbonyl compounds to nitriles

  摘要：

  Cyanohydrin diethyl phosphates, readily obtained from various ketones and aldehydes by reaction with diethyl phosphorocyanidate and lithium cyanide, reacted chemoselectively with samarium(II) iodide in THF to give the corresponding nitriles in excellent yields. This method was also found applicable to alpha,beta-unsaturated carbonyl compounds via cyano phosphates to give beta,gamma-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds.

  DOI：

  10.1021/jo00005a031

文献信息

• Cyano phosphate: an efficient intermediate for the chemoselective conversion of carbonyl compounds to nitriles
  作者：Ryuji Yoneda、Shinya Harusawa、Takushi Kurihara

  DOI：10.1021/jo00005a031

  日期：1991.3

  Cyanohydrin diethyl phosphates, readily obtained from various ketones and aldehydes by reaction with diethyl phosphorocyanidate and lithium cyanide, reacted chemoselectively with samarium(II) iodide in THF to give the corresponding nitriles in excellent yields. This method was also found applicable to alpha,beta-unsaturated carbonyl compounds via cyano phosphates to give beta,gamma-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds.