5-phenyl-5H-dibenzo[b,h][1,6]naphthyridin-6-one | 115120-98-4

• 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: 5-phenyl-5H-dibenzo[b,h][1,6]naphthyridin-6-one
• 英文别名: 5-Phenyl-5H-dibenzo[b,h][1,6]naphthyridin-6-on；5-Phenylquinolino[4,3-b]quinolin-6-one
• CAS: 115120-98-4
• 化学式: C₂₂H₁₄N₂O
• 分子量: 322.366
• InChiKey: WNNBIDFSYFZDLX-UHFFFAOYSA-N

物化性质

• 沸点：
  564.1±32.0 °C(predicted)
• 密度：
  1.314±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• 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：

  4-羟基-1-苯基-1,2-二氢喹啉-2-酮 在 苯胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-phenyl-5H-dibenzo[b,h][1,6]naphthyridin-6-one
  参考文献：
  名称：

  Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones

  摘要：

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.

  DOI：

  10.1002/prac.19933350203

文献信息

• 593. Structure and colour in the indolo(3′ : 2′–3 : 4)quinoline and the 1 : 2-dihydroquinolino(3′ : 2′–3 : 4)quinoline series
  作者：Frederick G. Mann

  DOI：10.1039/jr9490002816

  日期：——
• 683. The structure and properties of certain polycyclic indolo- and quinolino-derivatives. Part XI. Derivatives of 4 : 5: 6: 7-tetrahydro-1-methyl-4-oxo-2 : 3-benzazepine
  作者：John T. Braunholtz、Frederick G. Mann

  DOI：10.1039/jr9580003377

  日期：——
• Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones
  作者：Werner Fiala、Wolfgang Stadlbauer

  DOI：10.1002/prac.19933350203

  日期：——

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.