(2S,4S)-4-amino-1-benzyl-4-carboxyproline | 171336-75-7

• 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,4S)-4-amino-1-benzyl-4-carboxyproline
• 英文别名: (2S,4S)-4-amino-1-benzylpyrrolidine-2,4-dicarboxylic acid
• CAS: 171336-75-7
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: LYCSUAGKQMUTBR-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-amino-1-benzyl-4-carboxyproline 在 palladium hydroxide - carbon 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以83%的产率得到(2S,4S)-4-amino-4-carboxyproline
  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：

  (2S,4R)-1-benzyl-4-hydroxyproline methyl ester 在 盐酸 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 48.5h， 生成 (2S,4S)-4-amino-1-benzyl-4-carboxyproline
  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

文献信息

• Synthesis and metabotropic glutamate receptor antagonist activity of N1-substituted analogs of 2R,4R-4-aminopyrrolidine-2,4-dicarboxylic acid
  作者：Matthew J Valli、Darryle D Schoepp、Rebecca A Wright、Bryan G Johnson、Ann E Kingston、Rosemarie Tomlinson、James A Monn

  DOI：10.1016/s0960-894x(98)00352-7

  日期：1998.8

  4R-APDC) has been prepared as constrained analogs of gamma-substituted glutamic acids and examined for their effects at recombinant metabotropic glutamate receptor (mGluR) subtypes in vitro. Appropriate substitution of the N1 position of 2R,4R-APDC resulted in the identification of a number of selective group II mGluR antagonists.

  制备了一系列（2R，4R）-4-氨基吡咯烷-2,4-二羧酸（2R，4R-APDC）的N1取代衍生物作为γ-取代谷氨酸的约束类似物，并研究了它们在重组代谢型中的作用体外谷氨酸受体（mGluR）亚型。适当替换2R，4R-APDC的N1位置导致鉴定出许多选择性的II类mGluR拮抗剂。
• Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues
  作者：Ken-ichi Tanaka、Hiroyuki Sawanishi

  DOI：10.1016/0957-4166(95)00209-8

  日期：1995.7

  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.