1-methyl-3-(phenylaminomethylene)-2,4-(1H,3H)-quinolinedione | 59856-28-9

• 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-3-(phenylaminomethylene)-2,4-(1H,3H)-quinolinedione
• 英文别名: 3-anilinomethylene-1-methyl-1H-quinoline-2,4-dione；3-(anilinomethylidene)-1-methylquinoline-2,4-dione
• CAS: 59856-28-9
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: COXZQGYYWPNXKI-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C(Solv: chlorobenzene (108-90-7))
• 沸点：
  420.4±45.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(phenylaminomethylene)-2,4-(1H,3H)-quinolinedione 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以81%的产率得到4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
  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
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 原甲酸三乙酯 、 苯胺 以 乙二醇 为溶剂， 以84%的产率得到1-methyl-3-(phenylaminomethylene)-2,4-(1H,3H)-quinolinedione
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Syntheses of fluorescent dyes. IX. New 4-hydroxycoumarins, 4-hydroxy-2-quinolones, 2<i>H</i>,5<i>H</i>-Pyrano[3,2-<i>c</i>]benzopyran-2,5-diones and 2<i>H</i>,5<i>H</i>-Pyrano[3,2-<i>c</i>]quinoline-2,5-diones
  作者：Andreas Knierzinger、Otto S. Wolfbeis

  DOI：10.1002/jhet.5570170204

  日期：1980.3

  7-Substituted 4-hydroxycoumarins (2a-e) and 4-hydroxy-2-quinolones (2f-i) have been synthesized from the appropriate phenols or anilines and were converted to the enamines 3 using triethoxymethane and aniline. Condensation of 3 with nitriles 4a-h gave substituted 2H,5H-pyrano[3,2-c]benzopyran-2,5-diones (5a-r) or 2H,5H-pyrano[3,2-c]quinoline-2,5-diones (5s-x), which exhibit both spontaneous and stimulated

  由适当的酚或苯胺合成了7位取代的4-羟基香豆素（2a-e）和4-羟基-2-喹诺酮（2f-i），并使用三乙氧基甲烷和苯胺将其转化为烯胺3。3与腈4a-h的缩合反应生成2 H，5 H-吡喃并[3,2- c ]苯并吡喃-2,5-二酮（5a-r）或2 H，5 H-吡喃并[3,2- c ]喹啉-2,5-二酮（5s-x），显示出自发的和受激的荧光，最大值介于418和549 nm之间。7a，b（由2d，e和3-氧代丁酸乙酯合成）的荧光光谱证明了5中的吸电子3取代基的显着影响，与化合物21-r相比，其最大值急剧转变为蓝色。。
• Roschger, Peter; Stadlbauer, Wolfgang, Liebigs Annalen der Chemie, 1991, # 4, p. 401 - 403
  作者：Roschger, Peter、Stadlbauer, Wolfgang

  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.