(5S,6S,7S,10R)-7-isopropyl-2,10-dimethyl-6-trimethylsilyloxyspiro[4.5]dec-1-ene | 871228-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S,6S,7S,10R)-7-isopropyl-2,10-dimethyl-6-trimethylsilyloxyspiro[4.5]dec-1-ene
• CAS: 871228-27-2
• 化学式: C₁₈H₃₄OSi
• 分子量: 294.553
• InChiKey: AJVJDOIUVRZUIS-VSZNYVQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (5S,6S,7S,10R)-7-isopropyl-2,10-dimethyl-6-trimethylsilyloxyspiro[4.5]dec-1-ene 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以91%的产率得到(-)-axenol
  参考文献：
  名称：

  Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone

  摘要：

  The synthesis of the spirocyclic sesquiterpenes (-)-gleenol and (-)-axenol in enantiomerically pure form has been achieved starting from R-(-)-carvone. The key step is the silicon guided acid-promoted rearrangement of a 9-trimethylsilyl-5,6-epoxy-noreudesmane prepared from 3-tiimethylsilyldihydrocarvone in several steps involving Robinson annulation, enone deconjugation and epoxidation. Acid treatment of the epoxy-noreudesmane gave a norspiroaxane as the main product, which was used as intermediate for the synthesis of two naturally occurring sesquiterpenes gleenol and axenol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.025
• 作为产物：
  描述：

  (5R,6S,7S,10R)-7-isopropyl-10-methyl-6-trimethylsilyloxyspiro[4.5]decan-2-one 在 cerium(III) chloride 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 生成 (5S,6S,7S,10R)-7-isopropyl-2,10-dimethyl-6-trimethylsilyloxyspiro[4.5]dec-1-ene
  参考文献：
  名称：

  Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone

  摘要：

  The synthesis of the spirocyclic sesquiterpenes (-)-gleenol and (-)-axenol in enantiomerically pure form has been achieved starting from R-(-)-carvone. The key step is the silicon guided acid-promoted rearrangement of a 9-trimethylsilyl-5,6-epoxy-noreudesmane prepared from 3-tiimethylsilyldihydrocarvone in several steps involving Robinson annulation, enone deconjugation and epoxidation. Acid treatment of the epoxy-noreudesmane gave a norspiroaxane as the main product, which was used as intermediate for the synthesis of two naturally occurring sesquiterpenes gleenol and axenol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.025