(S)-3-[(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester | 180287-36-9

• 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: (S)-3-[(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-3-[(2S)-2-(1,3-dioxoisoindol-2-yl)propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylate
• CAS: 180287-36-9
• 化学式: C₂₀H₂₃N₃O₆
• 分子量: 401.419
• InChiKey: BCRUIDFHMBZLGU-FZMZJTMJSA-N

物化性质

• 沸点：
  513.3±60.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-[(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 邻苯二甲酰基-L-丙氨酸
  参考文献：
  名称：

  Dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary: Stereoselective synthesis of α-amino acids by Gabriel reaction

  摘要：

  A Highly stereoselective Gabriel reaction via dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary was exploited. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4- carboxylate (2a) with potassium phthalimide at room temperature predominantly afforded tert-butyl (4S)-1-methyl-3-((2S)-2-(phthaloylamino)propionyl)-2- oxoimidazolidine-4-carboxylate ((S,S)-5a) in a good yield which was derived to L-alanine derivative (7) by removal of the chiral auxiliary. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0040-4039(96)00977-x
• 作为产物：
  描述：

  potassium phtalimide 、 tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate 以 various solvent(s) 为溶剂， 反应 12.0h， 以90%的产率得到(S)-3-[(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionyl]-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary: Stereoselective synthesis of α-amino acids by Gabriel reaction

  摘要：

  A Highly stereoselective Gabriel reaction via dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary was exploited. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4- carboxylate (2a) with potassium phthalimide at room temperature predominantly afforded tert-butyl (4S)-1-methyl-3-((2S)-2-(phthaloylamino)propionyl)-2- oxoimidazolidine-4-carboxylate ((S,S)-5a) in a good yield which was derived to L-alanine derivative (7) by removal of the chiral auxiliary. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0040-4039(96)00977-x