3β,12β-diacetoxy-5α-pregna-14,16-dien-20R-ol | 444069-12-9

• 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,12β-diacetoxy-5α-pregna-14,16-dien-20R-ol
• 英文别名: [(3S,5S,8R,9S,10S,12R,13S)-12-acetyloxy-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 444069-12-9
• 化学式: C₂₅H₃₆O₅
• 分子量: 416.558
• InChiKey: AVFWOARUXKCVFQ-MYKIIGGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β,12β-diacetoxy-5α-pregna-14,16-dien-20R-ol 在 oxygen 、 rose bengal 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以40%的产率得到[(1R,2R,5S,7S,10S,11S,13R,14S,15R)-13-acetyloxy-15-[(1R)-1-hydroxyethyl]-10,14-dimethyl-16,17-dioxapentacyclo[13.2.2.01,14.02,11.05,10]nonadec-18-en-7-yl] acetate
  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+
• 作为产物：
  描述：

  3β,12β-Diacetoxy-20-oxo-5α-pregnadien-(14,16) 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以62%的产率得到3β,12β-diacetoxy-5α-pregna-14,16-dien-20R-ol
  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+