(2S,4R)-4-(2-Phenoxy-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester | 113490-67-8

• 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,4R)-4-(2-Phenoxy-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• CAS: 113490-67-8
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: LAUNTDMTFAAYBN-MOPGFXCFSA-N

物化性质

• 沸点：
  580.8±50.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-(2-Phenoxy-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 在 palladium on activated charcoal 氯化亚砜 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 L-Proline, 4-(2-phenoxyethoxy)-, methyl ester, trans-
  参考文献：
  名称：

  Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines

  摘要：

  The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described. These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition. The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril. The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.

  DOI：

  10.1021/jm00399a033
• 作为产物：
  描述：

  Cbz-L-羟脯氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以27%的产率得到(2S,4R)-4-(2-Phenoxy-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
  参考文献：
  名称：

  Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines

  摘要：

  The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described. These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition. The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril. The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.

  DOI：

  10.1021/jm00399a033