5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylic acid | 1432283-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylic acid
• CAS: 1432283-10-7
• 化学式: C₆H₅N₅O₂
• 分子量: 179.138
• InChiKey: PHDXYZWXNYIHPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氰基-1H-吡咯-2-甲酸乙酯 在 sodium azide 、 氯化铵 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Dissecting the Complex Recognition Interfaces of Potent Tetrazole- and Pyrrole-Based Anion Binders

  摘要：

  Tetrazoles are potent anion binders. We report here a new family of tetrazole pyrrole amide hosts that arise when a tetrazole is incorporated as a new binding element alongside the well-known amidopyrrole anion-binding scaffold. In addition to reporting three new, modular synthetic routes that can be used to access these structures, we also report that the new hosts are highly potent binders of chloride. Along the way, we carried out studies of a pyrrole ester control compound that, surprisingly, bound anions almost as strongly as did the amide analogues. This led us to investigate further the relative importance of the amide NH in halide binding. We report that, despite the regular appearance of this dose amide NH-Cl contact in calculated and experimental X-ray structures, the amide NH in this family of anion hosts does solution.

  DOI：

  10.1021/jo400372c