(1R,3E,7E,9R,10S,12R,14R)-9-[(tert-butyldimethylsilyl)oxy]-12-hydroperoxy-14-isopropyl-4,8,12-trimethylbicyclo[8.2.2]tetradeca-3,7-dien-11-one | 1207477-89-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3E,7E,9R,10S,12R,14R)-9-[(tert-butyldimethylsilyl)oxy]-12-hydroperoxy-14-isopropyl-4,8,12-trimethylbicyclo[8.2.2]tetradeca-3,7-dien-11-one
• CAS: 1207477-89-1
• 化学式: C₂₆H₄₆O₄Si
• 分子量: 450.734
• InChiKey: WIBJHSIOWHYIEH-BXKFWUOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3E,7E,9R,10S,12R,14R)-9-[(tert-butyldimethylsilyl)oxy]-12-hydroperoxy-14-isopropyl-4,8,12-trimethylbicyclo[8.2.2]tetradeca-3,7-dien-11-one 在 盐酸 作用下， 以 四氯化碳 、 水 为溶剂， 反应 117.0h， 以45%的产率得到(1S,2R,3E,7E,10R,12R)-10-acetyl-2-[(tert-butyldimethylsilyl)oxy]-12-isopropyl-3,7-dimethylcyclododeca-3,7-dienecarboxylic acid
  参考文献：
  名称：

  Enantiospecific Synthesis of the Cubitane Skeleton

  摘要：

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.

  DOI：

  10.1021/ol902854t
• 作为产物：
  描述：

  (1R,3E,7E,9R,10S,12S,14R)-9-[tert-butyl(dimethyl)silyl]oxy-4,8,12-trimethyl-14-propan-2-ylbicyclo[8.2.2]tetradeca-3,7-dien-11-one 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以64%的产率得到(1R,3E,7E,9R,10S,12R,14R)-9-[(tert-butyldimethylsilyl)oxy]-12-hydroperoxy-14-isopropyl-4,8,12-trimethylbicyclo[8.2.2]tetradeca-3,7-dien-11-one
  参考文献：
  名称：

  Enantiospecific Synthesis of the Cubitane Skeleton

  摘要：

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.

  DOI：

  10.1021/ol902854t