(3aR,6R,6aS)-2-ethyl-5,6-diphenylperhydropyrrolo[3,4-c]pyrrole-1,3,4-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aR,6R,6aS)-2-ethyl-5,6-diphenylperhydropyrrolo[3,4-c]pyrrole-1,3,4-trione
• 英文别名: (3aS,6S,6aR)-2-ethyl-5,6-diphenyl-6,6a-dihydro-3aH-pyrrolo[3,4-c]pyrrole-1,3,4-trione
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: WSDSPIPZIVIJLW-BRWVUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-乙基马来酰亚胺 、 二溴二氟甲烷 、 (E)-N-benzylidenebenzenamine 在 增效醚 、 四丁基溴化铵 、 水 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到(3aR,6S,6aS)-2-ethyl-5,6-diphenylperhydropyrrolo[3,4-c]pyrrole-1,3,4-trione
  参考文献：
  名称：

  摘要：

  Difluoro(iminio)methanides generated by the action of difluorocarbene on Schiff bases react with derivatives of maleic and fumaric acids, following the 1,3-dipolar cycloaddition pattern to give 2,2-difluoropyrrolidines which were detected by gas chromatography-mass spectrometry. The final products are stereoisomeric substituted 2-pyrrolidinones formed by hydrolysis of difluoropyrrolidines and their dehydrofluorination products, 2-fluoro-4,5-dihydropyrroles. The observed stereoselectivity of the cycloaddition suggests Z configuration of intermediate ylide and both endo- and exo-approach to the dipolarophile in the transition state corresponding to cycloaddition.

  DOI：

  10.1023/a:1019659021891

文献信息

• ——
  作者：M. S. Novikov、A. F. Khlebnikov、E. S. Sidorina、A. E. Masalev、J. Kopf、R. R. Kostikov

  DOI：10.1023/a:1019659021891

  日期：——

  Difluoro(iminio)methanides generated by the action of difluorocarbene on Schiff bases react with derivatives of maleic and fumaric acids, following the 1,3-dipolar cycloaddition pattern to give 2,2-difluoropyrrolidines which were detected by gas chromatography-mass spectrometry. The final products are stereoisomeric substituted 2-pyrrolidinones formed by hydrolysis of difluoropyrrolidines and their dehydrofluorination products, 2-fluoro-4,5-dihydropyrroles. The observed stereoselectivity of the cycloaddition suggests Z configuration of intermediate ylide and both endo- and exo-approach to the dipolarophile in the transition state corresponding to cycloaddition.