1-(quinolin-3-yl)pyridin-2(1H)-one

• 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: 1-(quinolin-3-yl)pyridin-2(1H)-one
• 英文别名: 1-Quinolin-3-ylpyridin-2-one
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: YPVCVYIREYPFLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-羟基吡啶 、 3-溴喹啉 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以90%的产率得到1-(quinolin-3-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  A Facile Copper-Catalyzed Ullmann Condensation: N-Arylation of Heterocyclic Compounds Containing an -NHCO- Moiety.

  摘要：

  N-芳基杂环化合物通过使用商业可得的铜催化剂（催化量为1-10摩尔%）从芳基卤化物和含有-NHCO-基团的杂环化合物合成，产率令人满意。此催化反应适用于N-芳基-2-吡啶酮、-2-吡咔啉酮、-1(2H)-异喹啉酮、-1(2H)-邻苯二氮䓬酮、-4(3H)-喹唑啉酮和-1, 2, 3-苯并三嗪-4(3H)-酮衍生物的合成。

  DOI：

  10.1248/cpb.45.719

文献信息

• A Facile Copper-Catalyzed Ullmann Condensation: N-Arylation of Heterocyclic Compounds Containing an -NHCO- Moiety.
  作者：Masakatsu SUGHARA、Tatsuzo UKITA

  DOI：10.1248/cpb.45.719

  日期：——

  N-Aryl heterocyclic compounds were synthesized from aryl halides and heterocyclic compounds containing an -NHCO- moiety by using a catalytic amount (1-10 mol%) of a commercially available copper catalyst in satisfactory yields. This catalytic reaction was applicable to the synthesis of N-aryl-2-pyridone, -2-pyrrolidone, -1(2H)-isoquinolone, -1(2H)-phthalazinone, -4(3H)-quinazolinone and -1, 2, 3-benzotriazin-4(3H)-one derivatives.

  N-芳基杂环化合物通过使用商业可得的铜催化剂（催化量为1-10摩尔%）从芳基卤化物和含有-NHCO-基团的杂环化合物合成，产率令人满意。此催化反应适用于N-芳基-2-吡啶酮、-2-吡咔啉酮、-1(2H)-异喹啉酮、-1(2H)-邻苯二氮䓬酮、-4(3H)-喹唑啉酮和-1, 2, 3-苯并三嗪-4(3H)-酮衍生物的合成。
• 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.