(5R,6S,7S,9R,10R)-5,6-epoxy-3,3-ethylenedioxy-9-trimethylsilyl-15-noreudesmane | 871228-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (5R,6S,7S,9R,10R)-5,6-epoxy-3,3-ethylenedioxy-9-trimethylsilyl-15-noreudesmane
• 英文别名: [(1'aS,2'S,4'R,4'aR,8'aR)-4'a-methyl-2'-propan-2-ylspiro[1,3-dioxolane-2,7'-2,3,4,5,6,8-hexahydro-1aH-naphtho[4,4a-b]oxirene]-4'-yl]-trimethylsilane
• CAS: 871228-15-8
• 化学式: C₁₉H₃₄O₃Si
• 分子量: 338.563
• InChiKey: UJRURLGWIGFNHZ-OREBXVKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S,7S,9R,10R)-5,6-epoxy-3,3-ethylenedioxy-9-trimethylsilyl-15-noreudesmane 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 (2S,4R,4aR)-2-Isopropyl-4a-methyl-4-trimethylsilanyl-octahydro-naphthalene-1,7-dione 、 (4aR,5R,7S,8S)-8-Hydroxy-7-isopropyl-4a-methyl-5-trimethylsilanyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-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
• 作为产物：
  描述：

  (7S,9R,10R)-3,3-ethylenedioxy-9-trimethylsilyl-15-nor-5-eudesmene 在 Oxone 、 18-冠醚-6 、 碳酸氢钠 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 以89%的产率得到(5R,6S,7S,9R,10R)-5,6-epoxy-3,3-ethylenedioxy-9-trimethylsilyl-15-noreudesmane
  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.