1α,2α-cyclomethylene-6-chloro-16β-bromo-17α-hydroxy-4,6-pregnadiene-3,20-dione | 574742-69-1

• 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: 1α,2α-cyclomethylene-6-chloro-16β-bromo-17α-hydroxy-4,6-pregnadiene-3,20-dione
• 英文别名: (1S,2S,3S,5R,11R,12S,14S,15R,16S)-15-acetyl-14-bromo-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
• CAS: 574742-69-1
• 化学式: C₂₂H₂₆BrClO₃
• 分子量: 453.804
• InChiKey: RNSJRGRISJOQLV-BAYUQPBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trifluoroacetic anhydride 、 1α,2α-cyclomethylene-6-chloro-16β-bromo-17α-hydroxy-4,6-pregnadiene-3,20-dione 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以23.7 mg的产率得到16β-bromocyproterone acetate
  参考文献：
  名称：

  The First Syntheses of 16β-Chloro- and 16β-Bromo-cyproterone Acetate

  摘要：

  The first syntheses of 16beta-chloro- and 16beta-bromo-cyproterone acetate is described. The preparation of 16beta-chlorocyproterone acetate was accomplished in eight steps (6.5% overall yield) from commercially available 16-dehydropregnenolone acetate. 16beta-Bromocyproterone acetate was prepared from 16beta-chlorocyproterone acetate with base-induced epoxide formation as the key step.

  DOI：

  10.1081/scc-120018931
• 作为产物：
  描述：

  6α,7α-epoxy-1α,2α-cyclomethylene-16β-chloro-17α-acetoxy-4-pregnene-3,20-dione 在 aluminum oxide 、 溴 、 N,N-dimethylacetamide hydrochloride 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 、 苯 为溶剂， 反应 102.5h， 生成 1α,2α-cyclomethylene-6-chloro-16β-bromo-17α-hydroxy-4,6-pregnadiene-3,20-dione
  参考文献：
  名称：

  The First Syntheses of 16β-Chloro- and 16β-Bromo-cyproterone Acetate

  摘要：

  The first syntheses of 16beta-chloro- and 16beta-bromo-cyproterone acetate is described. The preparation of 16beta-chlorocyproterone acetate was accomplished in eight steps (6.5% overall yield) from commercially available 16-dehydropregnenolone acetate. 16beta-Bromocyproterone acetate was prepared from 16beta-chlorocyproterone acetate with base-induced epoxide formation as the key step.

  DOI：

  10.1081/scc-120018931