isopropyl (2S)-1-benzyl-4-oxoprolinate | 154342-92-4

• 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: isopropyl (2S)-1-benzyl-4-oxoprolinate
• 英文别名: propan-2-yl (2S)-1-benzyl-4-oxopyrrolidine-2-carboxylate
• CAS: 154342-92-4
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: MRPGUTMGSHNGFO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl (2S)-1-benzyl-4-oxoprolinate 在 盐酸 、 氯化亚砜 作用下， 以 水 、 异丙醇 为溶剂， 反应 54.0h， 生成 methyl (2S,4S)-4-amino-1-benzyl-4-methoxycarbonylprolinate
  参考文献：
  名称：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues

  摘要：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyprolines, i.e. (2S,4S)-3, (2S,4R)-4, and their corresponding enantiomers, as novel conformationally restricted analogues of glutamic acid, were performed from trans-4-hydroxy-L-proline as a homochiral starting material. The key step was the spirohydantoin ring formation by employing the Bucherer-Bergs reaction of 4-oxoproline derivatives. These structures were determined by NMR studies.

  DOI：

  10.1016/0957-4166(95)00209-8
• 作为产物：
  描述：

  isopropyl (2S,4R)-1-benzyl-4-hydroxyprolinate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 isopropyl (2S)-1-benzyl-4-oxoprolinate
  参考文献：
  名称：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues

  摘要：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyprolines, i.e. (2S,4S)-3, (2S,4R)-4, and their corresponding enantiomers, as novel conformationally restricted analogues of glutamic acid, were performed from trans-4-hydroxy-L-proline as a homochiral starting material. The key step was the spirohydantoin ring formation by employing the Bucherer-Bergs reaction of 4-oxoproline derivatives. These structures were determined by NMR studies.

  DOI：

  10.1016/0957-4166(95)00209-8