1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide | 372083-32-4

• 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-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide
• 英文别名: 1-Butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide；1-butyl-4-hydroxy-2-oxoquinoline-3-carbohydrazide
• CAS: 372083-32-4
• 化学式: C₁₄H₁₇N₃O₃
• 分子量: 275.307
• InChiKey: HYCMBBWEOPQVOW-UHFFFAOYSA-N

物化性质

• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide 、 3-乙酰基-4-羟基喹啉-2(1h)-酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以88%的产率得到1-butyl-4-hydroxy-N-[1-(4-hydroxy-2-oxo-1H-quinolin-3-yl)ethylideneamino]-2-oxoquinoline-3-carboxamide
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 152*. 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline and its biologically active derivatives

  摘要：

  A synthesis and study of the spatial structure of 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline have been carried. 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids [1-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)ethylidene]hydrazides were prepared from this compound by two routes. A comparative analysis of the antitubercular properties of the synthesized compounds and of the closely structurally related N,N'-di(1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)hydrazines has been performed.

  DOI：

  10.1007/s10593-009-0246-2
• 作为产物：
  描述：

  ethyl 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate 在 一水合肼 作用下， 生成 1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide
  参考文献：
  名称：

  4-hydroxy-2-quinolones 165*. 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehydes and their thiosemicarbazones. Synthesis, structure, and biological properties

  摘要：

  Two variants are discussed of the synthesis of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid beta-N-tosylhydrazides which undergo a McFayden-Stevens reaction to give 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehydes in high yields. It was shown that the thiosemicarbazones prepared from them exist in the solid state exclusively in the syn-form while in solution a hydrazone. <-> enhydrazine tautomerism is observed. The results of a study of the antitubercular activity of the synthesized compounds are reported.

  DOI：

  10.1007/s10593-009-0327-2

文献信息

• 4-Hydroxy-2-quinolones 171*. Synthesis, isomerism, and antitubercular activity of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid alkylidenehydrazides
  作者：I. V. Ukrainets、Liu Yangyang、A. A. Tkach、A. V. Turov、O. S. Golovchenko

  DOI：10.1007/s10593-010-0431-3

  日期：2009.11

  Alkylidenehydrazides have been synthesized by the reaction of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazides with lower dialkyl ketones in order to reveal a structure-antitubercular activity relationship. It was shown by H-1 NMR spectroscopy that hydrazones obtained from the unsymmetrical ketone-methyl ethyl ketone-exist primarily in the E-isomer form. It was found that the presence of two aliphatic substituents in the alkylidene fragment of the compounds investigated leads to a marked lowering of antimicobacterial properties.
• 4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides
  作者：I. V. Ukrainets、L. V. Sidorenko、O. S. Golovchenko

  DOI：10.1007/s10593-007-0221-8

  日期：2007.11