4-chloro-3-formyl-2-dimethylaminoquinoline | 159112-46-6

• 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: 4-chloro-3-formyl-2-dimethylaminoquinoline
• 英文别名: 4-chloro-2-(dimethylamino)quinoline-3-carbaldehyde
• CAS: 159112-46-6
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: JHSXPIIWKPUUDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-3-formyl-2-dimethylaminoquinoline 在 哌啶 、 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 2.0h， 生成 3-ethoxycarbonyl-5-dimethylaminopyrano<3,2-c>quinolin-2-one
  参考文献：
  名称：

  Synthesis and study the pharmacological activity of derivatives of 5-dimethylaminopyrano[3,2-c]quinolin-2-ones

  摘要：

  DOI：

  10.1007/bf02226521
• 作为产物：
  描述：

  1-(2-azido-phenyl)-ethanone 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 4.0h， 以35%的产率得到4-chloro-3-formyl-2-dimethylaminoquinoline
  参考文献：
  名称：

  A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions

  摘要：

  Studies have been carried out on a new novel method for the synthesis of 2-(N,N-disubstituted)aminoquinoline via intramolecular electrophilic substitution of methyleniminium salts by azide. Treatment of 1-(2-azidophenyl)ethanone with Vilsmeier reagent (DMF/POCl3) gave 4-chloro-2-dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2-dimethylaminoquinoline, whereas 1-(2-azidophenyl)propanone and 1-(2-azidophenyl)butanone give unformylated products 4-chloro-3-methyl-2-dimethylaminoquinoline, 4-chloro-3-methylquinoline and 4-chloro-3-ethyl-2-dimethylaminoquinolin 4-chloro-3-ethylquinoline respectively. The possible mechanisms for the formation of the products are discussed. The effect of the N,N-dimethylamino leaving group has been studied using sterically hindered N-methylformanilide(MFA), N-formylpiperidine(NFP) and N-formylmorpholine(NFM) instead of DMF. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00887-4

文献信息

• A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions
  作者：Ramiya R. Amaresh、Paramasivan T. Perumal

  DOI：10.1016/s0040-4020(98)00887-4

  日期：1998.11

  Studies have been carried out on a new novel method for the synthesis of 2-(N,N-disubstituted)aminoquinoline via intramolecular electrophilic substitution of methyleniminium salts by azide. Treatment of 1-(2-azidophenyl)ethanone with Vilsmeier reagent (DMF/POCl3) gave 4-chloro-2-dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2-dimethylaminoquinoline, whereas 1-(2-azidophenyl)propanone and 1-(2-azidophenyl)butanone give unformylated products 4-chloro-3-methyl-2-dimethylaminoquinoline, 4-chloro-3-methylquinoline and 4-chloro-3-ethyl-2-dimethylaminoquinolin 4-chloro-3-ethylquinoline respectively. The possible mechanisms for the formation of the products are discussed. The effect of the N,N-dimethylamino leaving group has been studied using sterically hindered N-methylformanilide(MFA), N-formylpiperidine(NFP) and N-formylmorpholine(NFM) instead of DMF. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A novel one pot synthesis of 2-dimethylaminoquinoline derivatives from arylazido ketones by cyclization under vilsmeier condition
  作者：Ramiya R. Amaresh、Paramasivan T. Perumal

  DOI：10.1016/s0040-4039(98)00625-x

  日期：1998.5

  1-(2-Azidophenyl)ethanone on treatment with Vilsmeier reagent yields 4-chloro-2-dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2-dimethylaminoquinoline, whereas 1-(2-azidophenyl)propanone and butanone derivatives give the corresponding 4-chloro-3-alkyl-2-dimethylaminoquinolines and 3-alkyl-4-chloroquinolines. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and study the pharmacological activity of derivatives of 5-dimethylaminopyrano[3,2-c]quinolin-2-ones
  作者：I. N. Nesterova、L. M. Alekseeva、N. I. Andreeva、S. M. Golovina、V. G. Granik

  DOI：10.1007/bf02226521

  日期：1995.2