4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid chloride | 543699-85-0

• 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-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid chloride
• 英文别名: 4-methyl-2-oxo-1H-quinoline-3-carbonyl chloride
• CAS: 543699-85-0
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: AMZAKDXJWLQNDK-UHFFFAOYSA-N

物化性质

• 沸点：
  416.8±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid chloride 、 4-氯苯乙胺 在 三乙胺 作用下， 以 丙酮 为溶剂， 生成 N-[2-(4-chlorophenyl)ethyl]-4-methyl-2-oxo-1H-quinoline-3-carboxamide
  参考文献：
  名称：

  4-羟基-2-喹诺酮类140. 4-甲基-2-氧代-1,2-二氢喹啉-3-羧酸的芳基烷基酰胺的合成和利尿活性

  摘要：

  The interaction of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid with thionyl chloride in oxygen-containing solvents leads to the formation of a significant amount of colored side products, consequently it was proposed the reaction be carried out in carbon tetrachloride. The synthesis of a series of amides was effected by the amidation of the obtained acid chloride with appropriate primary arylalkylamines. Results are presented of a study of the effect of the synthesized compounds on the urine-excreting function of the kidney.

  DOI：

  10.1007/s10593-008-0009-5
• 作为产物：
  描述：

  ethyl 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 在 sodium hydroxide 、 氯化亚砜 、 水 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid chloride
  参考文献：
  名称：

  4-hydroxy-2-quinolones. 96. Synthesis and properties of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

  摘要：

  DOI：

  10.1007/s10593-006-0160-9

文献信息

• Quinolone–benzylpiperidine derivatives as novel acetylcholinesterase inhibitor and antioxidant hybrids for Alzheimer Disease
  作者：Marc Pudlo、Vincent Luzet、Lhassane Ismaïli、Isabelle Tomassoli、Anne Iutzeler、Bernard Refouvelet

  DOI：10.1016/j.bmc.2014.02.046

  日期：2014.4

  Design, synthesis and evaluation of new acetylcholinesterase inhibitors by combining quinolinecarboxamide to a benzylpiperidine moiety are described. Then, a series of hybrids have been developed by introducing radical scavengers. Molecular modeling was performed and structure activity relationships are discussed. Among the series, most potent compounds show effective AchE inhibitions, high selectivities over butyrylcholinesterase and high radical scavenging activities. On the basis of this work, the ability of quinolone derivatives to serve in the design of N-benzylpiperidine linked multipotent molecules for the treatment of Alzheimer Disease has been established. (C) 2014 Elsevier Ltd. All rights reserved.
• 4-Hydroxy-2-quinolones 150*. Efficient synthesis, structure, and biological activities of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides
  作者：I. V. Ukrainets、N. L. Bereznyakova、V. A. Parshikov、O. V. Gorokhova

  DOI：10.1007/s10593-009-0209-7

  日期：2008.12

  A simple and efficient method for preparing 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides is proposed. The results of a study of the diuretic activity of the compounds synthesized are reported.