(exo,exo,exo,endo)-1,2:4,5:7,8:10,11-tetraepoxy-cyclododecane | 522665-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (exo,exo,exo,endo)-1,2:4,5:7,8:10,11-tetraepoxy-cyclododecane
• 英文别名: (1R,3S,5R,7S,9R,11R,13S,15S)-4,8,12,16-tetraoxapentacyclo[13.1.0.03,5.07,9.011,13]hexadecane
• CAS: 522665-80-1
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: AWPQMJFLVGSKMA-ZXEOIRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (exo,exo,exo,endo)-1,2:4,5:7,8:10,11-tetraepoxy-cyclododecane 在 六甲基磷酰三胺 、 三甲基氯硅烷 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以29%的产率得到(+/-)-(1R,2R,4S,5R,7R,8R,10S,11R)-4,5:10,11-diepoxy-8-chloro-13-oxabicyclo[5.5.1]tridecan-2-ol
  参考文献：
  名称：

  Cyclododecatetraene Tetraepoxide:  Highly Diastereofacial Epoxidation of all-(Z)-1,4,7,10-Cyclododecatetraene and Selective Synthesis of Bridged Bis-oxocanes

  摘要：

  Epoxidation of all-(Z)-1,4,7,10-cyclododecatetraene has been investigated with use of m-CPBA and dimethyldioxirane in anhydrous solvent. The diastereo-selectivity of multiple epoxidation steps is complete affording only exo,exo,exo,endo-1,4,7,10-tetraepoxide. To understand this result, the step-by-step epoxidation reaction was investigated and each step was found to be highly regio- and stereoselective. Finally, a Lewis acid-catalyzed ethanolysis or treatment with HBr/KBr of the tetraepoxide gave rearranged diepoxy-oxabicyclo[5.5.1]tridecane (bridged bis-oxo-canes) in which eight stereocenters were controlled.

  DOI：

  10.1021/jo026736r
• 作为产物：
  描述：

  (Z,Z,Z,Z)-1,4,7,10-cyclododecatetraene 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 以98%的产率得到(exo,exo,exo,endo)-1,2:4,5:7,8:10,11-tetraepoxy-cyclododecane
  参考文献：
  名称：

  Cyclododecatetraene Tetraepoxide:  Highly Diastereofacial Epoxidation of all-(Z)-1,4,7,10-Cyclododecatetraene and Selective Synthesis of Bridged Bis-oxocanes

  摘要：

  Epoxidation of all-(Z)-1,4,7,10-cyclododecatetraene has been investigated with use of m-CPBA and dimethyldioxirane in anhydrous solvent. The diastereo-selectivity of multiple epoxidation steps is complete affording only exo,exo,exo,endo-1,4,7,10-tetraepoxide. To understand this result, the step-by-step epoxidation reaction was investigated and each step was found to be highly regio- and stereoselective. Finally, a Lewis acid-catalyzed ethanolysis or treatment with HBr/KBr of the tetraepoxide gave rearranged diepoxy-oxabicyclo[5.5.1]tridecane (bridged bis-oxo-canes) in which eight stereocenters were controlled.

  DOI：

  10.1021/jo026736r