1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-carboxylic acid | 725265-84-9

• 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: 1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-carboxylic acid
• 英文别名: 2-(4-phenylbutanoyl)-cyclopent-2-ene-carboxylic acid L-proline amide；(2S)-1-[2-(4-phenylbutanoyl)cyclopent-2-ene-1-carbonyl]pyrrolidine-2-carboxylic acid
• CAS: 725265-84-9
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: UOSDDHMHDJZIES-ZVAWYAOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-carboxylic acid 在 氯甲酸乙酯 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-nitrile
  参考文献：
  名称：

  A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors

  摘要：

  With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.

  DOI：

  10.1021/jm049503w
• 作为产物：
  描述：

  1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以94%的产率得到1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-carboxylic acid
  参考文献：
  名称：

  A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors

  摘要：

  With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.

  DOI：

  10.1021/jm049503w