(R)-N,N-dimethyl-2-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamide | 1111659-11-0

• 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: (R)-N,N-dimethyl-2-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamide
• 英文别名: (2R)-N,N-dimethyl-2-[[4-(trifluoromethyl)phenyl]methyl]pyrrolidine-2-carboxamide
• CAS: 1111659-11-0
• 化学式: C₁₅H₁₉F₃N₂O
• 分子量: 300.324
• InChiKey: CALGOSVKFCURQQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-N,N-dimethyl-1-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamide 在 三溴化硼 、 三乙胺 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(R)-N,N-dimethyl-2-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Asymmetric Lewis Acid Mediated [1,2]-Rearrangement of Proline-Derived Ammonium Ylides

  摘要：

  The first example of asymmetric Lewis acid mediated [1,2]-rearrangement of N-benzylic proline amides to form quaternary proline derivatives is reported. The presented reaction is shown to proceed with remarkable high C-N-C chirality transfer. Various quaternary proline derivatives have been prepared in good to excellent yields and high enantiomeric purity.

  DOI：

  10.1021/ol8028803

文献信息

• Asymmetric Lewis Acid Mediated [1,2]-Rearrangement of Proline-Derived Ammonium Ylides
  作者：Pavel Tuzina、Peter Somfai

  DOI：10.1021/ol8028803

  日期：2009.2.19

  The first example of asymmetric Lewis acid mediated [1,2]-rearrangement of N-benzylic proline amides to form quaternary proline derivatives is reported. The presented reaction is shown to proceed with remarkable high C-N-C chirality transfer. Various quaternary proline derivatives have been prepared in good to excellent yields and high enantiomeric purity.