2-chloro-5-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)pyridine | 1427476-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-5-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)pyridine
• 英文别名: 2-Chloro-5-(2-phenyl-4,5-dihydroimidazol-1-yl)pyridine；2-chloro-5-(2-phenyl-4,5-dihydroimidazol-1-yl)pyridine
• CAS: 1427476-03-6
• 化学式: C₁₄H₁₂ClN₃
• 分子量: 257.722
• InChiKey: VIYHHOPDLAPUMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯-5-碘吡啶 、 2-苯基咪唑啉 在 caesium carbonate 、 copper(I) bromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 18.0h， 以40%的产率得到2-chloro-5-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)pyridine
  参考文献：
  名称：

  Copper-Catalyzed N-Arylation of 2-Imidazolines with Aryl Iodides

  摘要：

  The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, "ligand-free" conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.

  DOI：

  10.1021/jo400120r

文献信息

• Copper-Catalyzed <i>N</i>-Arylation of 2-Imidazolines with Aryl Iodides
  作者：Owen A. Davis、Matthew Hughes、James A. Bull

  DOI：10.1021/jo400120r

  日期：2013.4.5

  The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, "ligand-free" conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.