(2S,3R)-5-Oxo-3-phenyl-1-p-tolyl-pyrrolidine-2-carboxylic acid

• 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: (2S,3R)-5-Oxo-3-phenyl-1-p-tolyl-pyrrolidine-2-carboxylic acid
• 英文别名: (2S,3R)-1-(4-methylphenyl)-5-oxo-3-phenylpyrrolidine-2-carboxylic acid
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: YKGKBVCFCLJPIQ-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-5-Oxo-3-phenyl-1-p-tolyl-pyrrolidine-2-carboxylic acid 在 sodium bromate 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以80%的产率得到1-(p-tolyl)-3-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  A novel synthetic approach towards N-phenylsuccinimides from γ-lactam-2-carboxylic acid derivatives by reaction with CAN–NaBrO3

  摘要：

  N-Arylsuccinimides have been synthesized by decarboxylative oxidation of N-aryl-gamma-lactam-2-carboxylic acids with the dual oxidant CAN/NaBrO(3) in refluxing acetonitrile-water. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.071

文献信息

• Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a facile entry to N-aryl-formylpyrroles
  作者：Pranab Haldar、Joyram Guin、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2004.12.107

  日期：2005.2

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-arylpyri-olidine-2/3-yl)-methanols in good yields at room temperature using sodium borohydride-iodine. Controlled oxidation and aromatisation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles. (C) 2004 Elsevier Ltd. All rights reserved.
• A novel synthetic approach towards N-phenylsuccinimides from γ-lactam-2-carboxylic acid derivatives by reaction with CAN–NaBrO3
  作者：Gopa Barman、Mahuya Roy、Jayanta. K. Ray

  DOI：10.1016/j.tetlet.2007.12.071

  日期：2008.2

  N-Arylsuccinimides have been synthesized by decarboxylative oxidation of N-aryl-gamma-lactam-2-carboxylic acids with the dual oxidant CAN/NaBrO(3) in refluxing acetonitrile-water. (C) 2008 Elsevier Ltd. All rights reserved.