(4aS,4bR,5S,6aS,6bR,8aR,9aS,9bS)-4b-Fluoro-5-hydroxy-6b-mercapto-4a,6a,8a-trimethyl-4a,4b,5,6,6a,6b,8a,9,9a,9b,10,11-dodecahydro-8-oxa-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-2,7-dione | 214975-04-9

• 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: (4aS,4bR,5S,6aS,6bR,8aR,9aS,9bS)-4b-Fluoro-5-hydroxy-6b-mercapto-4a,6a,8a-trimethyl-4a,4b,5,6,6a,6b,8a,9,9a,9b,10,11-dodecahydro-8-oxa-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-2,7-dione
• 英文别名: (1S,2S,4R,7R,8S,10S,11R,12S)-11-fluoro-10-hydroxy-4,8,12-trimethyl-7-sulfanyl-5-oxapentacyclo[9.8.0.02,8.04,7.012,17]nonadeca-13,16-diene-6,15-dione
• CAS: 214975-04-9
• 化学式: C₂₁H₂₅FO₄S
• 分子量: 392.492
• InChiKey: JOOGKDOUCAFXLQ-PXECCSRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4aS,4bR,5S,6aS,6bR,8aR,9aS,9bS)-4b-Fluoro-5-hydroxy-6b-mercapto-4a,6a,8a-trimethyl-4a,4b,5,6,6a,6b,8a,9,9a,9b,10,11-dodecahydro-8-oxa-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-2,7-dione 在 碘 、 碳酸氢钠 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.5h， 以58%的产率得到(1S,2S,4R,7R,8S,10S,11R,12S)-11-fluoro-7-[[(1S,2S,4R,7R,8S,10S,11R,12S)-11-fluoro-10-hydroxy-4,8,12-trimethyl-6,15-dioxo-5-oxapentacyclo[9.8.0.02,8.04,7.012,17]nonadeca-13,16-dien-7-yl]disulfanyl]-10-hydroxy-4,8,12-trimethyl-5-oxapentacyclo[9.8.0.02,8.04,7.012,17]nonadeca-13,16-diene-6,15-dione
  参考文献：
  名称：

  Rearrangement of a 16α,17α-Epoxy-16β-methylandrostane-17β-carbothioic Acid to a 17β-Mercapto-16β-methylandrostane-17α,16α-carbolactone

  摘要：

  The 16 alpha,17 alpha-epoxy-16 beta-methylandrostane-17 beta-carbothioic acid 2b rearranges in solution at ambient temperature to the 17 beta-mercapto-16 beta-methylandrostane-17 alpha,16 alpha-carbolactone 6a, possibly via the spirocyclic alpha-thiolactone 5.

  DOI：

  10.1021/jo9812375
• 作为产物：
  描述：

  16a,17α-epoxy-9α-fluoro-11β-hydroxy-16β-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid 在 三氟乙酸 作用下， 反应 3.0h， 以50%的产率得到(4aS,4bR,5S,6aS,6bR,8aR,9aS,9bS)-4b-Fluoro-5-hydroxy-6b-mercapto-4a,6a,8a-trimethyl-4a,4b,5,6,6a,6b,8a,9,9a,9b,10,11-dodecahydro-8-oxa-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-2,7-dione
  参考文献：
  名称：

  Rearrangement of a 16α,17α-Epoxy-16β-methylandrostane-17β-carbothioic Acid to a 17β-Mercapto-16β-methylandrostane-17α,16α-carbolactone

  摘要：

  The 16 alpha,17 alpha-epoxy-16 beta-methylandrostane-17 beta-carbothioic acid 2b rearranges in solution at ambient temperature to the 17 beta-mercapto-16 beta-methylandrostane-17 alpha,16 alpha-carbolactone 6a, possibly via the spirocyclic alpha-thiolactone 5.

  DOI：

  10.1021/jo9812375