4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid β-N-tosylhydrazide | 368888-88-4

• 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: 4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid β-N-tosylhydrazide
• 英文别名: 4-hydroxy-N'-[(4-methylphenyl)sulfonyl]-2-oxo-1-propyl-1,2-dihydroquinoline-3-carbohydrazide；4-hydroxy-N'-(4-methylphenyl)sulfonyl-2-oxo-1-propylquinoline-3-carbohydrazide
• CAS: 368888-88-4
• 化学式: C₂₀H₂₁N₃O₅S
• 分子量: 415.47
• InChiKey: CLZBVSUBVGLWFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid β-N-tosylhydrazide 在 sodium carbonate 作用下， 以 乙二醇 为溶剂， 生成 4-Hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carbaldehyde
  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
• 作为产物：
  描述：

  对甲苯磺酰肼 、 ethyl 1-propyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以53%的产率得到4-hydroxy-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid β-N-tosylhydrazide
  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. 169*. synthesis and bromination of 1-allyl-3-(arylamino-methylene)quinoline-2,4-(1h,3h)-diones
  作者：I. V. Ukrainets、Liu Yangyang、N. L. Bereznyakova、A. V. Turov

  DOI：10.1007/s10593-010-0412-6

  日期：2009.10

  Bromination of 1-allyl-substituted 3-(arylaminomethylene)quinoline-2,4-(1H,3H)-diones with one equivalent of molecular bromine in glacial acetic acid and subsequent dilution of the reaction mixture with water is accompanied by halocyclization and hydrolysis to form 2-bromomethyl-5-oxo-1,2 dihydro-5H- oxazolo[3,2-a]quinoline-4-carbaldehyde.
• 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
  作者：I. V. Ukrainets、Liu Yangyang、A. A. Tkach、O. V. Gorokhova、A. V. Turov

  DOI：10.1007/s10593-009-0327-2

  日期：2009.6

  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.