(1R,2S,3S,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid diethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3S,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid diethyl ester
• 英文别名: diethyl (1R,2S,3S,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylate
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: CMGXETSNEFQLLJ-USZNOCQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环己二烯 、 富马酸二乙酯 在 triflimide activated chiral oxazaborolidine 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以90%的产率得到(1R,2S,3S,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition

  摘要：

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.

  DOI：

  10.1021/ja035393r

文献信息

• Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition
  作者：Do Hyun Ryu、E. J. Corey

  DOI：10.1021/ja035393r

  日期：2003.5.1

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.