(R)-Methyl 2-(4-chloro-2-methylphenoxy)butanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-Methyl 2-(4-chloro-2-methylphenoxy)butanoate
• 英文别名: methyl (2R)-2-(4-chloro-2-methylphenoxy)butanoate
• 化学式: C₁₂H₁₅ClO₃
• 分子量: 242.702
• InChiKey: AJZGQNQDRVDNMO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-Methyl 2-(4-chloro-2-methylphenoxy)butanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以53%的产率得到(R)-2-(4-Chloro-2-methylphenoxy)butanoic acid
  参考文献：
  名称：

  Carboxylic acids and skeletal muscle chloride channel conductance: effects on the biological activity induced by the introduction of methyl groups on the aromatic ring of chiral α-(4-chloro-phenoxy)alkanoic acids

  摘要：

  One or two methyl groups have been introduced on the aromatic ring of two chiral clofibric acid analogs, 2-(4-chloro-phenoxy)propanoic and 2-(4-chloro-phenoxy)butanoic acids. The biological activity of the derivatives obtained (3-6) has been evaluated on the skeletal muscle chloride conductance (gCl). The results confirm the hypothesis of two different sites modulating chloride channel function, an excitatory site that increases channel activity and an inhibitory site that produces a channel block. In fact, this chemical modification strongly reduces the blocking activity of the (R)-and (S)-enantiomers in comparison with the parent compounds, but does not markedly affect the ability of the (R)-enantiomers to increase chloride channel conductance. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01041-2
• 作为产物：
  描述：

  (S)-2-羟基丁酸甲酯 、 4-氯-2-甲基苯酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以24%的产率得到(R)-Methyl 2-(4-chloro-2-methylphenoxy)butanoate
  参考文献：
  名称：

  Carboxylic acids and skeletal muscle chloride channel conductance: effects on the biological activity induced by the introduction of methyl groups on the aromatic ring of chiral α-(4-chloro-phenoxy)alkanoic acids

  摘要：

  One or two methyl groups have been introduced on the aromatic ring of two chiral clofibric acid analogs, 2-(4-chloro-phenoxy)propanoic and 2-(4-chloro-phenoxy)butanoic acids. The biological activity of the derivatives obtained (3-6) has been evaluated on the skeletal muscle chloride conductance (gCl). The results confirm the hypothesis of two different sites modulating chloride channel function, an excitatory site that increases channel activity and an inhibitory site that produces a channel block. In fact, this chemical modification strongly reduces the blocking activity of the (R)-and (S)-enantiomers in comparison with the parent compounds, but does not markedly affect the ability of the (R)-enantiomers to increase chloride channel conductance. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01041-2

文献信息

• Carboxylic acids and skeletal muscle chloride channel conductance: effects on the biological activity induced by the introduction of methyl groups on the aromatic ring of chiral α-(4-chloro-phenoxy)alkanoic acids
  作者：Savina Ferorelli、Fulvio Loiodice、Vincenzo Tortorella、Diana Conte-Camerino、Anna Maria De Luca

  DOI：10.1016/s0014-827x(01)01041-2

  日期：2001.4

  One or two methyl groups have been introduced on the aromatic ring of two chiral clofibric acid analogs, 2-(4-chloro-phenoxy)propanoic and 2-(4-chloro-phenoxy)butanoic acids. The biological activity of the derivatives obtained (3-6) has been evaluated on the skeletal muscle chloride conductance (gCl). The results confirm the hypothesis of two different sites modulating chloride channel function, an excitatory site that increases channel activity and an inhibitory site that produces a channel block. In fact, this chemical modification strongly reduces the blocking activity of the (R)-and (S)-enantiomers in comparison with the parent compounds, but does not markedly affect the ability of the (R)-enantiomers to increase chloride channel conductance. (C) 2001 Elsevier Science S.A. All rights reserved.