4-(2-hydroxybenzoylamino)benzoic acid methyl ester | 805246-74-6

• 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: 4-(2-hydroxybenzoylamino)benzoic acid methyl ester
• 英文别名: Methyl 4-[(2-hydroxybenzoyl)amino]benzoate
• CAS: 805246-74-6
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: RZRSJJXWIDPCKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基苯甲酸甲酯 、 水杨酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(2-hydroxybenzoylamino)benzoic acid methyl ester
  参考文献：
  名称：

  Anion-Triggered Substituent-Dependent Conformational Switching of Salicylanilides. New Hints for Understanding the Inhibitory Mechanism of Salicylanilides

  摘要：

  A series of salicylanilides (1a - h) bearing varied substituents at the 3'- or 4'-position of the anilino moiety (substituent = p-OCH3, p-CH3, m-CH3, H, p-Cl, m-Cl, p-CO2CH3, and p-CN) were synthesized. In acetonitrile all of the substituted salicylanilides 1a - h predominantly adopt the '' closed-ring '' conformation facilitated by a strong intramolecular OH center dot center dot center dot O=C hydrogen bond. In the presence of H2PO4-, the conformation of 1a - h was found to be modulated by the substituent. With our proposed proton-transfer fluorescence probing method, we were able to show that the conformation of 1a - f bearing a not highly electron-withdrawing substituent was switched to the '' open-ring '' form by H2PO4-, whereas 1h bearing a highly electron-withdrawing substituent, p-CN, remained in the '' closed-ring '' conformation. The significance of these findings for understanding, from a molecular structural point of view, the mechanism of salicylanilide-based inhibitors for inhibiting the protein tyrosine kinase epidermal growth factor receptor was discussed.

  DOI：

  10.1021/jo701823d

文献信息

• Anion-Triggered Substituent-Dependent Conformational Switching of Salicylanilides. New Hints for Understanding the Inhibitory Mechanism of Salicylanilides
  作者：Lin Guo、Qiang-Li Wang、Qian-Qian Jiang、Qiu-Ju Jiang、Yun-Bao Jiang

  DOI：10.1021/jo701823d

  日期：2007.12.1

  A series of salicylanilides (1a - h) bearing varied substituents at the 3'- or 4'-position of the anilino moiety (substituent = p-OCH3, p-CH3, m-CH3, H, p-Cl, m-Cl, p-CO2CH3, and p-CN) were synthesized. In acetonitrile all of the substituted salicylanilides 1a - h predominantly adopt the '' closed-ring '' conformation facilitated by a strong intramolecular OH center dot center dot center dot O=C hydrogen bond. In the presence of H2PO4-, the conformation of 1a - h was found to be modulated by the substituent. With our proposed proton-transfer fluorescence probing method, we were able to show that the conformation of 1a - f bearing a not highly electron-withdrawing substituent was switched to the '' open-ring '' form by H2PO4-, whereas 1h bearing a highly electron-withdrawing substituent, p-CN, remained in the '' closed-ring '' conformation. The significance of these findings for understanding, from a molecular structural point of view, the mechanism of salicylanilide-based inhibitors for inhibiting the protein tyrosine kinase epidermal growth factor receptor was discussed.