(3aR,6aS)-5-benzyl-2-methyl-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione | 1217186-44-1

• 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: (3aR,6aS)-5-benzyl-2-methyl-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione
• CAS: 1217186-44-1
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: VEDOXGOCEIAQKN-TXEJJXNPSA-N

物化性质

• 沸点：
  394.4±35.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 N-(甲氧甲基)-N-(三甲基硅甲基)苄胺 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 以81%的产率得到(3aR,6aS)-5-benzyl-2-methyl-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione
  参考文献：
  名称：

  [3+2] Dipolar cycloadditions of an unstabilised azomethine ylide under continuous flow conditions

  摘要：

  The [3+2] dipolar cycloaddition reactions of the unstabilised azomethine ylide precursor benzyl(methoxymethyl)(trimethylsilylmethyl)amine with 12 electron-deficient alkenes in the presence of catalytic trifluoroacetic acid are examined under continuous flow conditions (20-100 degrees C, 10-60 min residence time). The more reactive and hazardous alkenes such as ethyl acrylate, N-methylmaleimide and (E)-2-nitrostyrene afford substituted N-benzylpyrrolidine products in 77-83% yields, whereas less reactive dipolarophiles such as (E)-crotononitrile and ethyl methacrylate give lower yields (59-63%). Under optimised conditions, the reaction with ethyl acrylate is scaled up to afford ethyl N-benzylpyrrol-idine-3-carboxylate (30 g, 87%) in 1 h. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.071

文献信息

• [3+2] Dipolar cycloadditions of an unstabilised azomethine ylide under continuous flow conditions
  作者：Mark Grafton、Andrew C. Mansfield、M. Jonathan Fray

  DOI：10.1016/j.tetlet.2009.12.071

  日期：2010.2

  The [3+2] dipolar cycloaddition reactions of the unstabilised azomethine ylide precursor benzyl(methoxymethyl)(trimethylsilylmethyl)amine with 12 electron-deficient alkenes in the presence of catalytic trifluoroacetic acid are examined under continuous flow conditions (20-100 degrees C, 10-60 min residence time). The more reactive and hazardous alkenes such as ethyl acrylate, N-methylmaleimide and (E)-2-nitrostyrene afford substituted N-benzylpyrrolidine products in 77-83% yields, whereas less reactive dipolarophiles such as (E)-crotononitrile and ethyl methacrylate give lower yields (59-63%). Under optimised conditions, the reaction with ethyl acrylate is scaled up to afford ethyl N-benzylpyrrol-idine-3-carboxylate (30 g, 87%) in 1 h. (C) 2009 Elsevier Ltd. All rights reserved.