(E)-4-hydroxy-3-phenylbut-2-enoic acid | 99389-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-hydroxy-3-phenylbut-2-enoic acid
• CAS: 99389-53-4
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: OQRQZZOPYZIHSP-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯基-2H-呋喃-5-酮 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以46%的产率得到(E)-4-hydroxy-3-phenylbut-2-enoic acid
  参考文献：
  名称：

  Analogs of .gamma.-hydroxybutyric acid. Synthesis and binding studies

  摘要：

  Substituted 4-hydroxybutyric (GHB) or trans-4-hydroxycrotonic acids (T-HCA) and structurally related compounds were synthesized and submitted to [3H]GHB binding. Structure-activity relationships studies highlighted for [3H]GHB binding (a) the necessity of a nonlactonic, relatively extended conformation of the gamma-hydroxybutyric chain, (b) the existence of some bulk tolerance in the vicinity of the hydroxyl group, and (c) the high sensitivity toward isosteric replacements of the carboxyl or the hydroxyl groups. T-HCA has been recently identified as a naturally occurring substance in the central nervous system (CNS) and shows a better affinity than GHB. Our findings are in favor of the presence in the CNS of specific GHB binding sites, which are different from the GABA and the picrotoxin binding sites, and for which T-HCA may be an endogenous ligand.

  DOI：

  10.1021/jm00400a001

文献信息

• BOURGUIGNON, JEAN-JACQUES;SCHOENFELDER, ANGELE;SCHMITT, MARTINE;WERMUTH, +, J. MED. CHEM., 31,(1988) N 5, C. 893-897
  作者：BOURGUIGNON, JEAN-JACQUES、SCHOENFELDER, ANGELE、SCHMITT, MARTINE、WERMUTH, +

  DOI：——

  日期：——
• METHODS OF DETECTION USING X-RAY FLUORESCENCE
  申请人：Icagen, Inc.

  公开号：EP3681504A1

  公开（公告）日：2020-07-22
• [EN] METHODS OF DETECTION USING X-RAY FLUORESCENCE<br/>[FR] PROCÉDÉS DE DÉTECTION UTILISANT LA FLUORESCENCE X
  申请人：ICAGEN INC

  公开号：WO2019055754A1

  公开（公告）日：2019-03-21

  The present invention relates, in part, to methods of using X-ray fluorescence (XRF) spectrometry for analyzing (e.g., measuring) the binding of a soluble target to an insoluble material.
• Analogs of .gamma.-hydroxybutyric acid. Synthesis and binding studies
  作者：Jean Jacques Bourguignon、Angele Schoenfelder、Martine Schmitt、Camille Georges Wermuth、Viviane Hechler、Brigitte Charlier、Michel Maitre

  DOI：10.1021/jm00400a001

  日期：1988.5

  Substituted 4-hydroxybutyric (GHB) or trans-4-hydroxycrotonic acids (T-HCA) and structurally related compounds were synthesized and submitted to [3H]GHB binding. Structure-activity relationships studies highlighted for [3H]GHB binding (a) the necessity of a nonlactonic, relatively extended conformation of the gamma-hydroxybutyric chain, (b) the existence of some bulk tolerance in the vicinity of the hydroxyl group, and (c) the high sensitivity toward isosteric replacements of the carboxyl or the hydroxyl groups. T-HCA has been recently identified as a naturally occurring substance in the central nervous system (CNS) and shows a better affinity than GHB. Our findings are in favor of the presence in the CNS of specific GHB binding sites, which are different from the GABA and the picrotoxin binding sites, and for which T-HCA may be an endogenous ligand.