1-methyl-4-(phenylamino)-2(1H)-quinolone | 132911-19-4

• 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: 1-methyl-4-(phenylamino)-2(1H)-quinolone
• 英文别名: 1-methyl-4-phenylamino-2(1H)-quinolone；1-methyl-4-anilino-2(1H)-quinolone；4-Anilino-1-methylquinolin-2-one
• CAS: 132911-19-4
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: BULOXQATASUISD-UHFFFAOYSA-N

物化性质

• 熔点：
  199-201 °C(Solv: methanol (67-56-1))
• 沸点：
  392.0±42.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-噻吩亚甲基)甲烷-1,1-二甲腈 、 1-methyl-4-(phenylamino)-2(1H)-quinolone 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以70%的产率得到2-amino-3-cyano-6-methyl-4-(2'-thienyl)-1-phenyl-4H-pyrido[3,2-c]quinoline-5(1H,6H)-one
  参考文献：
  名称：

  El-Taweel; Ibrahim; Hanna, Bollettino Chimico Farmaceutico, 2001, vol. 140, # 5, p. 287 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 aniline hydrochloride 在 苯胺 作用下， 以95%的产率得到1-methyl-4-(phenylamino)-2(1H)-quinolone
  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

• Roschger, Peter; Stadlbauer, Wolfgang, Liebigs Annalen der Chemie, 1991, # 4, p. 401 - 403
  作者：Roschger, Peter、Stadlbauer, Wolfgang

  DOI：——

  日期：——
• ROSCHGER, PETER;STADLBAUER, WOLFGANG, LIEBIGS ANN. CHEM.,(1991) N, C. 401-403
  作者：ROSCHGER, PETER、STADLBAUER, WOLFGANG

  DOI：——

  日期：——
• El-Taweel; Ibrahim; Hanna, Bollettino Chimico Farmaceutico, 2001, vol. 140, # 5, p. 287 - 296
  作者：El-Taweel、Ibrahim、Hanna

  DOI：——

  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.