2-[1(S)-methyl-2-oxo-2-(5-oxo-2(R),3(S)-diphenyl-pyrrolidin-1-yl)-ethyl]-isoindole-1,3-dione | 548488-25-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[1(S)-methyl-2-oxo-2-(5-oxo-2(R),3(S)-diphenyl-pyrrolidin-1-yl)-ethyl]-isoindole-1,3-dione
• 英文别名: 2-[(2S)-1-oxo-1-[(2R,3S)-5-oxo-2,3-diphenylpyrrolidin-1-yl]propan-2-yl]isoindole-1,3-dione
• CAS: 548488-25-1
• 化学式: C₂₇H₂₂N₂O₄
• 分子量: 438.483
• InChiKey: WFRQZFNTBRBOKA-OWSXEPHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1(S)-methyl-2-oxo-2-(5-oxo-2(R),3(S)-diphenyl-pyrrolidin-1-yl)-ethyl]-isoindole-1,3-dione 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到trans-(4S,5R)-diphenyl-pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis, resolution and absolute configuration of trans 4,5-diphenyl-pyrrolidin-2-one: a possible chiral auxiliary

  摘要：

  beta-Lactam (+/-)-N-benzyl-4-phenyl-azetidin-2-one rac-6a was converted into the gamma-lactam (+/-)-traps-4,5-diphenyl-pyrrolidin-2-one rac-5 which was resolved via the preparation of diastereomers with N-phthalyl-L-alanine chloride or D-alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a chiral gamma-lactam in asymmetric induction due to the steric effects of its phenyl groups. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00097-1
• 作为产物：
  描述：

  1-benzyl-4-phenyl-2-azetidinone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.92h， 生成 2-[1(S)-methyl-2-oxo-2-(5-oxo-2(R),3(S)-diphenyl-pyrrolidin-1-yl)-ethyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis, resolution and absolute configuration of trans 4,5-diphenyl-pyrrolidin-2-one: a possible chiral auxiliary

  摘要：

  beta-Lactam (+/-)-N-benzyl-4-phenyl-azetidin-2-one rac-6a was converted into the gamma-lactam (+/-)-traps-4,5-diphenyl-pyrrolidin-2-one rac-5 which was resolved via the preparation of diastereomers with N-phthalyl-L-alanine chloride or D-alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a chiral gamma-lactam in asymmetric induction due to the steric effects of its phenyl groups. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00097-1

文献信息

• Synthesis, resolution and absolute configuration of trans 4,5-diphenyl-pyrrolidin-2-one: a possible chiral auxiliary
  作者：Jaime Escalante、Miguel A. González-Tototzin

  DOI：10.1016/s0957-4166(03)00097-1

  日期：2003.4

  beta-Lactam (+/-)-N-benzyl-4-phenyl-azetidin-2-one rac-6a was converted into the gamma-lactam (+/-)-traps-4,5-diphenyl-pyrrolidin-2-one rac-5 which was resolved via the preparation of diastereomers with N-phthalyl-L-alanine chloride or D-alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a chiral gamma-lactam in asymmetric induction due to the steric effects of its phenyl groups. (C) 2003 Elsevier Science Ltd. All rights reserved.