N-(2-phenylethynylcyclopentene-1-carbonyl)-L-phenylalanine N-(4-nitrophenyl)amide | 1192253-48-7

• 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: N-(2-phenylethynylcyclopentene-1-carbonyl)-L-phenylalanine N-(4-nitrophenyl)amide
• CAS: 1192253-48-7
• 化学式: C₂₉H₂₅N₃O₄
• 分子量: 479.535
• InChiKey: KNJFGMIXGZTAFM-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101.34
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(phenylethynyl)cyclopentanecarboxylic acid 、 H-Phe-pNA*HCl 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以76%的产率得到N-(2-phenylethynylcyclopentene-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