(αR,3S,5S)-α-amino-5-carboxy-2-oxo-3-pyrrolidineacetic acid | 1446910-93-5

• 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: (αR,3S,5S)-α-amino-5-carboxy-2-oxo-3-pyrrolidineacetic acid
• 英文别名: 1′,3-diepi-penmacric acid；(2S,4S)-4-[(R)-amino(carboxy)methyl]-5-oxopyrrolidine-2-carboxylic acid
• CAS: 1446910-93-5
• 化学式: C₇H₁₀N₂O₅
• 分子量: 202.167
• InChiKey: QEFCFJFZZLNSPP-YVZJFKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (αR,3S,5S)-5-(methoxycarbonyl)-1-(1,1-dimethylethoxy)carbonyl-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-3-pyrrolidineacetic acid methyl ester 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 以59%的产率得到(αR,3S,5S)-α-amino-5-carboxy-2-oxo-3-pyrrolidineacetic acid
  参考文献：
  名称：

  Total synthesis of penmacric acids via an intermolecular radical addition reaction

  摘要：

  The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-L-proline. Furthermore, 1',3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.006

文献信息

• Total synthesis of penmacric acids via an intermolecular radical addition reaction
  作者：Masafumi Ueda、Ayako Ono、Dai Nakao、Kenji Matsuno、Takeaki Naito、Okiko Miyata

  DOI：10.1016/j.tet.2013.06.006

  日期：2013.8

  The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-L-proline. Furthermore, 1',3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction. (C) 2013 Elsevier Ltd. All rights reserved.