(2S,3S)-1-methyl-5-oxo-2-phenyl-N[(1R)-1-phenylethyl]tetrahydro-1H-pyrrolidine-3-carboxylamide | 1020073-53-3

• 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: (2S,3S)-1-methyl-5-oxo-2-phenyl-N[(1R)-1-phenylethyl]tetrahydro-1H-pyrrolidine-3-carboxylamide
• 英文别名: (2S,3S)-1-methyl-5-oxo-2-phenyl-N-[(1R)-1-phenylethyl]pyrrolidine-3-carboxamide
• CAS: 1020073-53-3
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: GDCXISZVMIVASQ-DKSSEZFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2RS,3RS)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrole-3-carboxylic acid 、 α-苯乙胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以39%的产率得到(2S,3S)-1-methyl-5-oxo-2-phenyl-N[(1R)-1-phenylethyl]tetrahydro-1H-pyrrolidine-3-carboxylamide
  参考文献：
  名称：

  Enantiomers of (2R∗,3R∗)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid as novel chiral resolving agents

  摘要：

  A series of (2R*,3R*)-1-methyl-5-oxo-2-aryltetrahydro-1H-pyrrolidine-3-carboxylic acids were prepared and their structures were proven with X-ray crystallography. Racemic acid 5 has been resolved into enantiomers (2S,3S)-5 and (2R,3R)-5 by the formation of diastereomeric salts with brucine 9 and strychnidine 10, respectively. The ability of these enantiomers to serve as chiral discriminating agents was demonstrated by the chromatographic separation of diastereomeric amides and esters. Also, some preliminary results on the enantioselective reduction of prochiral imines with sodium borohydride modified by (2R,3R)-5 were collected. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.014

文献信息

• Enantiomers of (2R∗,3R∗)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid as novel chiral resolving agents
  作者：Katarzyna Piwowarczyk、Anna Zawadzka、Piotr Roszkowski、Joanna Szawkało、Andrzej Leniewski、Jan K. Maurin、Darius Kranz、Zbigniew Czarnocki

  DOI：10.1016/j.tetasy.2008.01.014

  日期：2008.2

  A series of (2R*,3R*)-1-methyl-5-oxo-2-aryltetrahydro-1H-pyrrolidine-3-carboxylic acids were prepared and their structures were proven with X-ray crystallography. Racemic acid 5 has been resolved into enantiomers (2S,3S)-5 and (2R,3R)-5 by the formation of diastereomeric salts with brucine 9 and strychnidine 10, respectively. The ability of these enantiomers to serve as chiral discriminating agents was demonstrated by the chromatographic separation of diastereomeric amides and esters. Also, some preliminary results on the enantioselective reduction of prochiral imines with sodium borohydride modified by (2R,3R)-5 were collected. (C) 2008 Elsevier Ltd. All rights reserved.