N-(3-quinolinyl)-2-furamide | 403666-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(3-quinolinyl)-2-furamide
• 英文别名: N-(quinolin-3-yl)furan-2-carboxamide；N-quinolin-3-ylfuran-2-carboxamide
• CAS: 403666-34-2
• 化学式: C₁₄H₁₀N₂O₂
• mdl: MFCD00442681
• 分子量: 238.246
• InChiKey: NVYKPHJLAKEQBY-UHFFFAOYSA-N

物化性质

• 沸点：
  331.9±17.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠酰胺 、 3-溴喹啉 在 tris-(dibenzylideneacetone)dipalladium(0) potassium phosphate 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以69%的产率得到N-(3-quinolinyl)-2-furamide
  参考文献：
  名称：

  Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands:  A Kinetic, Computational, and Synthetic Investigation

  摘要：

  We present results on the amidation of aryl halides and sulfonates utilizing a monodentate biaryl phosphine-Pd catalyst. Our results are in accord with a previous report that suggests that the formation of K-2-amidate complexes is deleterious to the effectiveness of a catalyst for this transformation and that their formation can be prevented by the use of appropriate bidentate ligands. We now provide data that suggest that the use of certain monodentate ligands can also prevent the formation of the K-2-amidate complexes and thereby generate more stable catalysts for the amination of aryl chlorides. Furthermore, computational studies shed light on the importance of the key feature(s) of the biaryl phosphines (a methyl group ortho to the phosphorus center) that enable the coupling to occur. The use of ligands that possess a methyl group ortho to the phosphorus center allows a variety of aryl and heteroaryl chlorides with various amides to be coupled in high yield.

  DOI：

  10.1021/ja0717414

文献信息

• Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands:  A Kinetic, Computational, and Synthetic Investigation
  作者：Takashi Ikawa、Timothy E. Barder、Mark R. Biscoe、Stephen L. Buchwald

  DOI：10.1021/ja0717414

  日期：2007.10.1

  We present results on the amidation of aryl halides and sulfonates utilizing a monodentate biaryl phosphine-Pd catalyst. Our results are in accord with a previous report that suggests that the formation of K-2-amidate complexes is deleterious to the effectiveness of a catalyst for this transformation and that their formation can be prevented by the use of appropriate bidentate ligands. We now provide data that suggest that the use of certain monodentate ligands can also prevent the formation of the K-2-amidate complexes and thereby generate more stable catalysts for the amination of aryl chlorides. Furthermore, computational studies shed light on the importance of the key feature(s) of the biaryl phosphines (a methyl group ortho to the phosphorus center) that enable the coupling to occur. The use of ligands that possess a methyl group ortho to the phosphorus center allows a variety of aryl and heteroaryl chlorides with various amides to be coupled in high yield.