4-Chloro-3-methyl-2-(4-morpholinyl)quinoline | 218129-59-0

• 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-methyl-2-(4-morpholinyl)quinoline
• 英文别名: 4-(4-chloro-3-methylquinolin-2-yl)morpholine
• CAS: 218129-59-0
• 化学式: C₁₄H₁₅ClN₂O
• 分子量: 262.739
• InChiKey: VWAUBURVFLVCEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲酰吗啉 、 1-(2-azidophenyl)propan-1-one 在 三氯氧磷 作用下， 反应 4.0h， 以18%的产率得到3-甲基-4-氯喹啉
  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