(2R,3S)-2-benzoyl-3-(4-tert-butylphenyl)oxirane-2-carbonitrile | 1261378-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-2-benzoyl-3-(4-tert-butylphenyl)oxirane-2-carbonitrile
• CAS: 1261378-78-2
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: CHTJTSCZOXFRQN-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-benzoyl-3-(4-(tert-butyl)phenyl)acrylonitrile 在 叔丁基过氧化氢 、 S-Α,Α-双(3,5-二甲基苯基)脯氨醇 作用下， 以 癸烷 、 间二甲苯 为溶剂， 以92%的产率得到(2R,3S)-2-benzoyl-3-(4-tert-butylphenyl)oxirane-2-carbonitrile
  参考文献：
  名称：

  Organocatalytic Stereoselective Epoxidation of Trisubstituted Acrylonitriles

  摘要：

  The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the transisomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).

  DOI：

  10.1021/jo102020a

文献信息

• Organocatalytic Stereoselective Epoxidation of Trisubstituted Acrylonitriles
  作者：Claudia De Fusco、Consiglia Tedesco、Alessandra Lattanzi

  DOI：10.1021/jo102020a

  日期：2011.1.21

  The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the transisomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).