(4aR,4bS,5S,6aS,6bR,9aR,10aS,10bS)-9-Bromo-5-hydroxy-4a,6a-dimethyl-6b-[2-(tetrahydro-pyran-2-yloxy)-acetyl]-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-one | 197845-58-2

• 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: (4aR,4bS,5S,6aS,6bR,9aR,10aS,10bS)-9-Bromo-5-hydroxy-4a,6a-dimethyl-6b-[2-(tetrahydro-pyran-2-yloxy)-acetyl]-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-one
• CAS: 197845-58-2
• 化学式: C₂₇H₃₄BrNO₆
• 分子量: 548.474
• InChiKey: JCAFEHZLVJLAAO-NWRFEFTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  94.42
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4aR,4bS,5S,6aS,6bR,9aR,10aS,10bS)-9-Bromo-5-hydroxy-4a,6a-dimethyl-6b-[2-(tetrahydro-pyran-2-yloxy)-acetyl]-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-one 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 120.0h， 生成 (4aR,4bS,5S,6aS,6bR,9aR,10aS,10bS)-5-Hydroxy-6b-(2-hydroxy-acetyl)-9-methoxy-4a,6a-dimethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-one
  参考文献：
  名称：

  Studies towards the synthesis of 16α-carboxyprednisolones. Chemistry of fused bromoisoxazolines

  摘要：

  Bromonitrile-N-oxide adds to the enone 9b/c completely regio-and stereoselectively to form the bromoisoxazoline 10b/c. The latter can be transformed into the nitrile 11, previously hydrolyzed(14) to the target 16 alpha-carbomethoxyprednisolone 4a a potentially locally active antiinflammatory steroid. The methoxyisoxazoline 12, prepared from 10b has proved surprisingly resistant to reductive cleavage of the N-O bond. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00983-6
• 作为产物：
  描述：

  脱氧强的松龙-16-烯 在 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.25h， 生成 (4aR,4bS,5S,6aS,6bR,9aR,10aS,10bS)-9-Bromo-5-hydroxy-4a,6a-dimethyl-6b-[2-(tetrahydro-pyran-2-yloxy)-acetyl]-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-2-one
  参考文献：
  名称：

  Studies towards the synthesis of 16α-carboxyprednisolones. Chemistry of fused bromoisoxazolines

  摘要：

  Bromonitrile-N-oxide adds to the enone 9b/c completely regio-and stereoselectively to form the bromoisoxazoline 10b/c. The latter can be transformed into the nitrile 11, previously hydrolyzed(14) to the target 16 alpha-carbomethoxyprednisolone 4a a potentially locally active antiinflammatory steroid. The methoxyisoxazoline 12, prepared from 10b has proved surprisingly resistant to reductive cleavage of the N-O bond. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00983-6