3β-acetoxy-16α,17β-dibromo-5β-pregnan-20-one

• 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: 3β-acetoxy-16α,17β-dibromo-5β-pregnan-20-one
• 英文别名: [(3S,5R,8R,9S,10S,13S,14S,16R,17S)-17-acetyl-16,17-dibromo-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• 化学式: C₂₃H₃₄Br₂O₃
• 分子量: 518.329
• InChiKey: AAQCXKOOMMJIGZ-QCOXTQDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sarasapogenin 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氯化铵 作用下， 以 四氯化碳 为溶剂， 反应 5.67h， 生成 3β-acetoxy-16α,17β-dibromo-5β-pregnan-20-one
  参考文献：
  名称：

  Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

  摘要：

  Two methods have been developed for efficient conversion of pregna-14,16-dien-20-ones into 14beta-hydroxyandrost-15-en-17-ones. One procedure consists of treatment of the ring-D dienone successively with sodium borohydride and singlet oxygen. The reaction is illustrated by the conversion of pregna-14,16-dien-20-one 1 into 14beta-hydroxyandrost-15-en-17-one 3, via the corresponding allylic alcohol 2. Although this two-step procedure is simple, it provides 3 in relatively low yield, accompanied by a smaller amount of the isomeric 14alpha-hydroxyandrost-15-en-17-one 6. An alternative one-step conversion is achieved by treatment of dienone 1 with a peroxyacid in the presence of a strong protic acid. This process is illustrated by the two-step conversion of dienone I into hydroxy ketone 11 in 51% overall yield (Scheme 5) and by the analogous conversion of dienone 13 into hydroxy ketone 24 in 61% overall yield (Scheme 11).

  DOI：

  10.1021/jo011175+

文献信息

• Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones
  作者：Jennifer D. Fell、Clayton H. Heathcock

  DOI：10.1021/jo011175+

  日期：2002.7.1

  Two methods have been developed for efficient conversion of pregna-14,16-dien-20-ones into 14beta-hydroxyandrost-15-en-17-ones. One procedure consists of treatment of the ring-D dienone successively with sodium borohydride and singlet oxygen. The reaction is illustrated by the conversion of pregna-14,16-dien-20-one 1 into 14beta-hydroxyandrost-15-en-17-one 3, via the corresponding allylic alcohol 2. Although this two-step procedure is simple, it provides 3 in relatively low yield, accompanied by a smaller amount of the isomeric 14alpha-hydroxyandrost-15-en-17-one 6. An alternative one-step conversion is achieved by treatment of dienone 1 with a peroxyacid in the presence of a strong protic acid. This process is illustrated by the two-step conversion of dienone I into hydroxy ketone 11 in 51% overall yield (Scheme 5) and by the analogous conversion of dienone 13 into hydroxy ketone 24 in 61% overall yield (Scheme 11).