(3S,8R,9S,10R,13S,14S,16S)-16-Bromomethyl-3-hydroxy-10,13,16-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one | 121059-45-8

• 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: (3S,8R,9S,10R,13S,14S,16S)-16-Bromomethyl-3-hydroxy-10,13,16-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
• 英文别名: (3S,8R,9S,10R,13S,14S,16S)-16-(bromomethyl)-3-hydroxy-10,13,16-trimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 121059-45-8
• 化学式: C₂₁H₃₁BrO₂
• 分子量: 395.38
• InChiKey: GBMNDFSMYNWTDS-SXRIAOIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,8R,9S,10R,13S,14S,16S)-16-Bromomethyl-3-hydroxy-10,13,16-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one 生成 Acetic acid (3S,8R,9S,10R,13S,14S,16S)-16-bromomethyl-10,13,16-trimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  SCHNEIDER, GYULA;WOLFLING, JANOS;MESKO, ESZTER;DOMBI, GYORGY, STEROIDS, 51,(1988) N-4, C. 317-327

  摘要：

  DOI：
• 作为产物：
  描述：

  17α-Methyl-16-methylen-androst-5-en-3β,17β-diol 在 N-溴代丁二酰亚胺(NBS) 、 高氯酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以57%的产率得到(3S,8R,9S,10R,13S,14S,16S)-16-Bromomethyl-3-hydroxy-10,13,16-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Steroids 35: Synthesis of 16,16-dimethyl-17β-hydroxysteroids

  摘要：

  The reaction of 16-methylene-17-ketosteroids (Ia), (Ic) and (Ie) with methyl magnesium iodide yields 16-methylene-17 alpha-methyl-17 beta-hydroxysteroids (IIa), (IIb) and (IId). These are subjected to the addition of hypobromous acid and the subsequent anionotropic rearrangement to convert them into 16 alpha-methyl-16 beta-bromomethyl-17-ketosteroids (Va), (Vb) and (Vd). These were reduced with LiA1H4 to obtain 16,16-dimethyl-17 beta-hydroxysteroids (VIa), (VIb) and (VId). Compounds (VIIa) and (VIIe) were selectively deacetylated yielding (VIIb) and (VIId); these were then oxidized and hydrolyzed to convert them into (VIf) and (VIg).

  DOI：

  10.1016/0039-128x(88)90021-9