(1S^*,2S^*,5R^*,6R^*)-2,5-bis<(tert-butyldimethylsilyl)oxy>-3-ethenylidene-7-oxabicyclo<4.1.0>heptane | 142508-56-3

• 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: (1S^*,2S^*,5R^*,6R^*)-2,5-bis<(tert-butyldimethylsilyl)oxy>-3-ethenylidene-7-oxabicyclo<4.1.0>heptane
• 英文别名: (1S^*,2S^*,5R^*,6R^*)-2,5-bis[(tert-butyldimethylsilyl)oxy]-3-ethenylidene-7-oxabicyclo[4.1.0]heptane
• CAS: 142508-56-3
• 化学式: C₂₀H₃₈O₃Si₂
• 分子量: 382.691
• InChiKey: WJWHYKNEWBZUMF-VSZNYVQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S^*,2R^*,3R^*,5R^*,6R^*)-2,5-bis<(tert-butyldimethylsilyl)oxy>-3-ethynyl-3-(methanesulfinoyl)-7-oxabicyclo<4.1.0>heptane 在 异丙基锂 作用下， 生成 (1S^*,2S^*,5R^*,6R^*)-2,5-bis<(tert-butyldimethylsilyl)oxy>-3-ethenylidene-7-oxabicyclo<4.1.0>heptane 、 (1S^*,2R^*,3R^*,5R^*,6R^*)-2,5-bis<(tert-butyldimethylsilyl)oxy>-3-ethynyl-7-oxabicyclo<4.1.0>heptan-3-ol 、 (1S*,2R*,5R*,6R*)-2,5-bis<(tert-butyldimethylsilyl)oxy>-3-(3-methylbuta-1,3-dienylidene)-7-oxabicyclo<4.1.0>heptane
  参考文献：
  名称：

  Stereospecific synthesis of a novel allenic cyclohexanoid epoxide from the fungus Eutypa lata

  摘要：

  The stereospecific synthesis of the novel allenic cyclohexanoid epoxide 13 is reported. Key steps include Diels-Alder reaction between a 1,4-dioxygenatedbuta-1,3-diene 1 and a ketene equivalent 2 and the coupling of a mixed isopropenyl cuprate with propagylic sulfinate 10.

  DOI：

  10.1021/jo00043a035

文献信息

• Stereospecific synthesis of a novel allenic cyclohexanoid epoxide from the fungus Eutypa lata
  作者：John Gordon、Raffaele Tabacchi

  DOI：10.1021/jo00043a035

  日期：1992.8

  The stereospecific synthesis of the novel allenic cyclohexanoid epoxide 13 is reported. Key steps include Diels-Alder reaction between a 1,4-dioxygenatedbuta-1,3-diene 1 and a ketene equivalent 2 and the coupling of a mixed isopropenyl cuprate with propagylic sulfinate 10.