[(1S,4R,5S,6R,7R,8S)-7-(benzenesulfonyl)-5-(4-nitrobenzoyl)oxy-8-(2-trimethylsilylethynyl)-2-oxabicyclo[4.2.0]octan-4-yl] 4-nitrobenzoate | 1256362-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S,4R,5S,6R,7R,8S)-7-(benzenesulfonyl)-5-(4-nitrobenzoyl)oxy-8-(2-trimethylsilylethynyl)-2-oxabicyclo[4.2.0]octan-4-yl] 4-nitrobenzoate
• CAS: 1256362-53-4
• 化学式: C₃₂H₃₀N₂O₁₁SSi
• 分子量: 678.749
• InChiKey: OFGLKIPNOGWYIY-WFNRLYLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (1S,4R,5S,6S,7R,8S)-7-(benzenesulfonyl)-7-[dimethyl(phenyl)silyl]-8-(2-trimethylsilylethynyl)-2-oxabicyclo[4.2.0]octane-4,5-diol 、 4-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以90%的产率得到[(1S,4R,5S,6R,7R,8S)-7-(benzenesulfonyl)-5-(4-nitrobenzoyl)oxy-8-(2-trimethylsilylethynyl)-2-oxabicyclo[4.2.0]octan-4-yl] 4-nitrobenzoate
  参考文献：
  名称：

  Chiral Cyclobutane Synthesis by Exploiting a Heteroatom-Directed Conjugate Addition

  摘要：

  The syntheses of both enantiomers of cyclobutanes B and ent-B are achieved through heteroatom-directed conjugate addition (HADCA) of nucleophiles to the epoxyvinylsulfone-substituted carbohydrates A and ent-A, which provided carbanions that intramolecularly attacked the epoxide with concomitant formation of the cyclobutane ring.

  DOI：

  10.1021/ol102383g

文献信息

• Chiral Cyclobutane Synthesis by Exploiting a Heteroatom-Directed Conjugate Addition
  作者：Kuo-Wei Tsao、Minoru Isobe

  DOI：10.1021/ol102383g

  日期：2010.11.19

  The syntheses of both enantiomers of cyclobutanes B and ent-B are achieved through heteroatom-directed conjugate addition (HADCA) of nucleophiles to the epoxyvinylsulfone-substituted carbohydrates A and ent-A, which provided carbanions that intramolecularly attacked the epoxide with concomitant formation of the cyclobutane ring.