4-氯-2-氧代-1-苯基喹啉-3-甲醛 | 148587-01-3

• 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
• 中文名称: 4-氯-2-氧代-1-苯基喹啉-3-甲醛
• 英文名称: 4-Chloro-2-oxo-1-phenylquinoline-3-carbaldehyde
• CAS: 148587-01-3
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: QZCRKPCOCDDFSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-2-氧代-1-苯基喹啉-3-甲醛 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以97%的产率得到4-Azido-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carbaldehyde
  参考文献：
  名称：

  4-叠氮基-3-肼基烷基喹啉与2-芳基氨基吡唑并[4,3- c ]喹诺酮类的杂环电反应†

  摘要：

  从4-羟基衍生物1经由甲苯磺酸酯3或氯化物5获得的4-叠氮基-3-酰基喹诺酮4与芳基肼6反应，生成4-叠氮基-3-肼基烷基喹啉7。热解7得到闭环产物，其分配给2-芳基氨基吡唑并[4，3- c ]喹诺酮类化合物10。通过差示扫描量热法（DSC）研究了叠氮化物4和7的热分解条件。

  DOI：

  10.1002/jhet.5570370625
• 作为产物：
  描述：

  4-羟基-1-苯基-1,2-二氢喹啉-2-酮 在 三氯氧磷 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-氯-2-氧代-1-苯基喹啉-3-甲醛
  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

• Stadlbauer, Wolfgang; Hojas, Gerhard, Journal of Heterocyclic Chemistry, 2004, vol. 41, # 5, p. 681 - 690
  作者：Stadlbauer, Wolfgang、Hojas, Gerhard

  DOI：——

  日期：——
• Jayashree, A.; Darbarwar, Malleshwar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 7, p. 676 - 678
  作者：Jayashree, A.、Darbarwar, Malleshwar

  DOI：——

  日期：——
• Jayashree, A.; Darbarwar, Malleshwar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 10, p. 1063 - 1065
  作者：Jayashree, A.、Darbarwar, Malleshwar

  DOI：——

  日期：——
• Jayashree, A.; Darbarwar, Malleshwar, Organic Preparations and Procedures International, 1993, vol. 25, # 6, p. 659 - 664
  作者：Jayashree, A.、Darbarwar, Malleshwar

  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.