5-hydroxy-5α-cholestan-6-one oxime | 52710-30-2

• 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: 5-hydroxy-5α-cholestan-6-one oxime
• 英文别名: 5-Hydroxy-5α-cholestan-6-on-oxim；6-Hydroxyimino-5-hydroxy-5α-cholestan；(5R,8S,9S,10R,13R,14S,17R)-6-hydroxyimino-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-5-ol
• CAS: 52710-30-2
• 化学式: C₂₇H₄₇NO₂
• 分子量: 417.676
• InChiKey: CMACOCOOQPZYTL-RJGGPJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-5α-cholestan-6-one oxime 在 盐酸 、 氯化亚砜 作用下， 生成 5,6-seco-5-oxo-cholestan-6-oic acid
  参考文献：
  名称：

  703.氮杂类固醇。第六部分 一些α-羟基酮肟的贝克曼重排

  摘要：

  DOI：

  10.1039/jr9630003774

文献信息

• Steroids and Walden inversion. Part LIX. Reactions of some steroid α-hydroxyamines
  作者：C. W. Shoppee、P. Ram、S. K. Roy

  DOI：10.1039/j39660001023

  日期：——

  Reduction of 5-hydroxy-5α-cholestan-4-one oxime and 5-hydroxy-5α-cholestan-6-one oxime with sodium–ethanol and lithium aluminium hydride gives, inter alia, the 4β-, 6α-, and 6β-amino-5-hydroxy-5α-cholestanes, whose deamination is described and briefly discussed. Attempts to dehydrate these α-hydroxy-amines to the related allylic amines were unsuccessful, as also were attempted ammonolyses of 4β-chlorocholest-5-ene

  用钠-乙醇和氢化铝锂还原5-羟基-5α-胆甾烷-4-一肟和5-羟基-5α-胆甾烷-6-一肟，除其他外，得到4β-，6α-和6β-氨基-5-羟基-5α-胆甾烷，其脱氨基作用已描述并作了简要讨论。将这些α-羟基胺脱水为相关的烯丙基胺的尝试均未成功，也尝试了4β-chlorocholest-5-ene和6β-chlorocholest-4-ene的氨解反应。