(5R,6S,7S,10R)-7-isopropyl-10-methyl-6-trimethylsilyloxyspiro[4.5]decan-2-one | 871228-24-9

• 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: (5R,6S,7S,10R)-7-isopropyl-10-methyl-6-trimethylsilyloxyspiro[4.5]decan-2-one
• 英文别名: (5R,6R,9S,10S)-6-methyl-9-propan-2-yl-10-trimethylsilyloxyspiro[4.5]decan-3-one
• CAS: 871228-24-9
• 化学式: C₁₇H₃₂O₂Si
• 分子量: 296.525
• InChiKey: IARXSGNLYPYGRM-BSWAZPDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R,6S,7S,10R)-7-isopropyl-10-methyl-6-trimethylsilyloxyspiro[4.5]decan-2-one 在 N-甲基吲哚酮 、 cerium(III) chloride 、 四丙基高钌酸铵 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.08h， 生成 (5S,7S,10R)-(+)-7-isopropyl-2,10-dimethylspiro[4.5]dec-1-en-6-one
  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)-6-hydroxy-7-isopropyl-10-methylspiro[4.5]decan-2-one 、 三甲基氯硅烷 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 1.0h， 生成 (5R,6S,7S,10R)-7-isopropyl-10-methyl-6-trimethylsilyloxyspiro[4.5]decan-2-one 、 (5R,6S,7S,10S)-7-isopropyl-10-methyl-6-trimethylsilyloxyspiro[4.5]decan-2-one
  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

文献信息

• Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone
  作者：Gonzalo Blay、Ana M. Collado、Begoña García、José R. Pedro

  DOI：10.1016/j.tet.2005.09.025

  日期：2005.11

  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.