5-cyano-N-(p-tolyl)-1H-pyrrole-2-carboxamide | 1432283-27-6

• 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: 5-cyano-N-(p-tolyl)-1H-pyrrole-2-carboxamide
• 英文别名: 5-cyano-N-(4-methylphenyl)-1H-pyrrole-2-carboxamide
• CAS: 1432283-27-6
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: LAPIOPRWYFVECA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-cyano-N-(p-tolyl)-1H-pyrrole-2-carboxamide 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95%的产率得到N-(4-methylphenyl)-5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxamide
  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
• 作为产物：
  描述：

  2-吡咯甲酸甲酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.0h， 生成 5-cyano-N-(p-tolyl)-1H-pyrrole-2-carboxamide
  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

文献信息

• Dissecting the Complex Recognition Interfaces of Potent Tetrazole- and Pyrrole-Based Anion Binders
  作者：Thomas Pinter、Chakravarthi Simhadri、Fraser Hof

  DOI：10.1021/jo400372c

  日期：2013.5.17

  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.