hydrazide of 1-propyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid | 148237-82-5

• 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: hydrazide of 1-propyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid
• 英文别名: 4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid hydrazide；4-Hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carbohydrazide；4-hydroxy-2-oxo-1-propylquinoline-3-carbohydrazide
• CAS: 148237-82-5
• 化学式: C₁₃H₁₅N₃O₃
• 分子量: 261.28
• InChiKey: KZYDFPNQJHNIQU-UHFFFAOYSA-N

物化性质

• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  hydrazide of 1-propyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid 反应 0.5h， 以80%的产率得到5-Propyl-1,2-dihydro-5H-pyrazolo[4,3-c]quinoline-3,4-dione
  参考文献：
  名称：

  4-Hydroxyquinolones-2

  摘要：

  DOI：

  10.1007/bf00531325
• 作为产物：
  描述：

  ethyl 1-propyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate 在 一水合肼 作用下， 生成 hydrazide of 1-propyl-2-oxo-4-hydroxyquinoline-3-carboxylic acid
  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. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids
  作者：I. V. Ukrainets、A. A. Tkach、Liu Yang Yang

  DOI：10.1007/s10593-009-0198-6

  日期：2008.11

  Two methods of preparation have been proposed and the synthesis has been effected of a large series of beta-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.
• 4-Hydroxy-2-quinolones. 152*. 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline and its biologically active derivatives
  作者：I. V. Ukrainets、A. A. Tkach、Liu Yang Yang

  DOI：10.1007/s10593-009-0246-2

  日期：2009.2

  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.
• 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
• 4-hydroxy-2-quinolones. 41. Reaction of hydrazides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids with ethyl orthoformate
  作者：I. V. Ukrainets、N. A. Jaradat、I. V. Gorlacheva、O. V. Gorokhova、L. V. Sidorenko、A. V. Turov

  DOI：10.1007/bf02283546

  日期：2000.2