3-(2-hydroxyphenyl)butyric acid | 62191-63-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-hydroxyphenyl)butyric acid
• 英文别名: 3-(2-Hydroxyphenyl)butanoic acid
• CAS: 62191-63-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VJZNRJAXRNUAML-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  333.1±17.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyphenyl)butyric acid 在 硝酸 作用下， 生成 β-Methyl-β-(2-hydroxy-3,5-dinitrophenyl)propionsaeure
  参考文献：
  名称：

  ERNST; BAER, Arzneimittel-Forschung/Drug Research, 1964, vol. 14, p. 81 - 84

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-3,4-二氢色烯-2-酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(2-hydroxyphenyl)butyric acid
  参考文献：
  名称：

  N-甲基氨基甲酸酯杀虫剂的微生物代谢。二。邻仲丁基苯基N-甲基氨基甲酸酯的代谢产物的合成。

  摘要：

  合成了邻仲丁基苯基 N-甲基氨基甲酸酯（BPMC）（I）的特征代谢物和预期代谢物。此外，还介绍了测定黑曲霉（Aspergillus niger van Tieghem）主要代谢物邻（2-羟基-1-甲基丙基）苯基 N-甲基氨基甲酸酯构型的初步实验。

  DOI：

  10.1248/cpb.24.1976

文献信息

• GAMMA-AMINO-BUTYRIC ACID DERIVATIVES AS GABAB RECEPTOR LIGANDS
  申请人：Xu Feng

  公开号：US20100267676A1

  公开（公告）日：2010-10-21

  Gamma-amino-butyric acid derivatives that are GABA B receptor ligands, pharmaceutical compositions comprising such derivatives, and methods of using such derivatives and pharmaceutical compositions thereof for treating diseases are disclosed.

  揭示了作为GABAB受体配体的γ-氨基丁酸衍生物、包括这种衍生物的药物组合物，以及使用这种衍生物和药物组合物治疗疾病的方法。
• Progress toward the Total Synthesis of Bacchopetiolone:  Application of a Tandem Aromatic Oxidation/Diels−Alder Reaction
  作者：Amélie Bérubé,、Ioana Drutu、John L. Wood

  DOI：10.1021/ol061737h

  日期：2006.11.1

  A stereoselective synthesis of the bacchopetiolone (1) carbocyclic core using a tandem phenolic oxidation/Diels-Alder reaction is described. [reaction: see text].

  描述了使用串联酚醛氧化/ Diels-Alder反应立体选择性合成bacchopetiolone（1）碳环核。[反应：请参见文字]。
• Enantioselective Cathodic Reduction of 4-Methylcoumarin: Dependence of Selectivity on Reaction Conditions and Investigation of the Mechanism
  作者：Merete Folmer Nielsen、Belen Batanero、Thorsten Löhl、Hans J. Schäfer、Ernst-Ulrich Würthwein、Roland Fröhlich

  DOI：10.1002/chem.19970031216

  日期：1997.12

  AbstractThe cathodic reduction of 4‐methylcoumarin (1) in acidic methanol/water in the presence of yohimbine leads to formation of a mixture of the hydrogenation product 4‐methyl‐3,4‐dihydrocoumarin (2), with an enantiomeric excess (ee) of (R)‐2of 0–67%, and the hydrodimer3. The relative yields of2and3and theeeof2depend on a number of experimental parameters such as pH, supporting electrolyte, working potential, and the concentrations of substrate and yohimbine, as demonstrated by a series of preparative‐scale experiments. In addition, a series of voltammetric and kinetic measurements were carried out to investigate the influence of the individual experimental parameters. Three mechanistic possibilities have been examined, and by combination of the analytical data with the results of the preparative experiments, a single model is put forward which is in accord with the available results. The main features of the mechanistic model can be summarized as follows: 1) under acidic conditions (pH 2–3) the electroactive species is a complex between1and H3O+, the reduction of which leads to an enolic radical; 2) this radical is not reduced at the working potential but tautomerizes into the more easily reduced keto radical or dimerizes; 3) the keto radical is reduced and further protonated; 4) the function of the yohimbineH+is to catalyze the tautomerization and enantioselectively protonate the final carbanion. Additionally, we conclude that the concentration of yohimbine in the immediate vicinity of the electrode is considerably higher than its stoichiometric concentration. Quantum chemical calculations demonstrate thatsiprotonation of the intermediate anion by yohimbineH+to give (R)‐2is energetically favored.
• GAMMA-AMINO-BUTYRIC ACID DERIVATIVES AS GABAb RECEPTOR LIGANDS
  申请人：XenoPort, Inc.

  公开号：EP2419401A2

  公开（公告）日：2012-02-22
• US8344028B2
  申请人：——

  公开号：US8344028B2

  公开（公告）日：2013-01-01