N-(2-(5-hydroxy-5-oxopent-1-ynyl)cyclopentene-1-carbonyl)-L-phenylalanine N-(4-nitrophenyl)amide | 1192253-37-4

• 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: N-(2-(5-hydroxy-5-oxopent-1-ynyl)cyclopentene-1-carbonyl)-L-phenylalanine N-(4-nitrophenyl)amide
• CAS: 1192253-37-4
• 化学式: C₂₆H₂₅N₃O₆
• 分子量: 475.501
• InChiKey: AELLDKYZMHJKDI-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  138.64
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-(2-(5-methoxy-5-oxopent-1-ynyl)cyclopentene-1-carbonyl)-L-phenylalanine N-(4-nitrophenyl)amide 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 16.0h， 以22%的产率得到N-(2-(5-hydroxy-5-oxopent-1-ynyl)cyclopentene-1-carbonyl)-L-phenylalanine N-(4-nitrophenyl)amide
  参考文献：
  名称：

  Synthesis of 2-(4-carboxybutenyl)- and 2-(4-carboxybutynyl)-cyclopentene-1-carboxamides

  摘要：

  Syntheses of 2-(4-carboxybut-1-enyl/4-carboxypent-1-ynyl)cyclopentene-1-carboxamides, compounds designed to mimic the phosphoSer-Pro dipeptide motif (the recognition sequence for the prolyl cis-trans isomerase Pin1), have been developed. Stille, Sonogashira and Suzuki couplings were envisaged to join the pentynoic and pentenoic acid side chains to the 2-position of cyclopentene-1-carboxylate esters. The ring- and side-chain carboxylic acids required orthogonal protection for later attachment of a Ph-NH(4-nitrophenyl) unit to the cyclopentene-1-carbonyl. The cyclopentenecarboxylates were unmasked and standard PyBOP peptide coupling afforded the target compounds. Comparisons of two routes using Bur and Me esters are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.085