3-(quinolin-3-yloxy)benzonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(quinolin-3-yloxy)benzonitrile
• 英文别名: 3-Quinolin-6-yloxybenzonitrile
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: SRTDDIOJSXNNQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-羟基喹啉 、 间溴苯甲腈 在 copper(l) iodide 、 2,2,6,6-四甲基-3,5-庚二酮 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以78%的产率得到3-(quinolin-3-yloxy)benzonitrile
  参考文献：
  名称：

  Cu-Catalyzed N- and O-Arylation of 2-, 3-, and 4-Hydroxypyridines and Hydroxyquinolines

  摘要：

  With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides, and 2-substituted aryl halides. In addition, by using a copper catalyst based on 2,2,6,6-tetramethylheptane-3,5-dione, 4, the first N-arylations of 4-hydroxypyridines and O-arylations of 3-hydroxypyridines with aryl bromides and iodides have been accomplished.

  DOI：

  10.1021/ol062904g

文献信息

• Cu-Catalyzed <i>N</i>- and <i>O</i>-Arylation of 2-, 3-, and 4-Hydroxypyridines and Hydroxyquinolines
  作者：Ryan A. Altman、Stephen L. Buchwald

  DOI：10.1021/ol062904g

  日期：2007.2.1

  With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides, and 2-substituted aryl halides. In addition, by using a copper catalyst based on 2,2,6,6-tetramethylheptane-3,5-dione, 4, the first N-arylations of 4-hydroxypyridines and O-arylations of 3-hydroxypyridines with aryl bromides and iodides have been accomplished.