3-phenyl-5-chloro-2-pyridone | 24228-17-9

• 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: 3-phenyl-5-chloro-2-pyridone
• 英文别名: 5-Chloro-3-phenylpyridin-2(1H)-one；5-chloro-3-phenyl-1H-pyridin-2-one
• CAS: 24228-17-9
• 化学式: C₁₁H₈ClNO
• 分子量: 205.644
• InChiKey: ANKOMKSSHMCFGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  392.8±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙酸乙酯 、 (Z)-N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate 在 potassium tert-butylate 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 9.75h， 以43%的产率得到3-phenyl-5-chloro-2-pyridone
  参考文献：
  名称：

  A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

  摘要：

  A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the beta -positisn. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

  DOI：

  10.1021/jo0155198

文献信息

• A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters
  作者：Jean-François Marcoux、Félix-Antoine Marcotte、Jimmy Wu、Peter G. Dormer、Ian W. Davies、David Hughes、Paul J. Reider

  DOI：10.1021/jo0155198

  日期：2001.6.1

  A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the beta -positisn. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.