4-羟基-1-甲基-2-氧喹啉-3-碳酰肼 | 74693-61-1

• 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
• 中文名称: 4-羟基-1-甲基-2-氧喹啉-3-碳酰肼
• 英文名称: 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid hydrazide
• 英文别名: 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid hydrazide；4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbohydrazide；3-Quinolinecarboxylic acid, 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-, hydrazide；4-hydroxy-1-methyl-2-oxoquinoline-3-carbohydrazide
• CAS: 74693-61-1
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: UJVPTHJMCJYAKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 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：
  95.7
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  4-羟基-1-甲基-2-氧喹啉-3-碳酰肼 反应 0.5h， 以86%的产率得到5-methyl-1,2,4,5-tetrahydropyrazolo<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：

  1,2-二氢-4-羟基-1-甲基-2-氧代-3-喹啉羧酸乙酯 在 肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以10%的产率得到4-羟基-1-甲基-2-氧喹啉-3-碳酰肼
  参考文献：
  名称：

  2-喹诺酮系列的转变

  摘要：

  氯氧化磷处理1-取代-1,2-二氢-4-羟基-2-氧-2-羟基-3-喹啉羧酸酯和4-羟基-1-甲基-3-硝基-2-（1 H）喹啉酮导致形成相应的4-氯-2-喹诺酮。描述了它们与各种碳，氮，氧和硫亲核试剂的反应。

  DOI：

  10.1002/jhet.5570180513

文献信息

• Transformations in the 2-quinolone series
  作者：Gary M. Coppola、Goetz E. Hardtmann

  DOI：10.1002/jhet.5570180513

  日期：1981.8

  The treatment of 1-substituted-1,2-dihydro-4-hydroxy-2-oxo-3-quinoline carboxylic acid esters and 4-hydroxy-1-methyl-3-nitro-2-(1H)quinolinone with phosphorus oxychloride resulted in the formation of the corresponding 4-chloro-2-quinolones. Their reactions with a variety of carbon, nitrogen, oxygen, and sulfur nucleophiles is described.

  氯氧化磷处理1-取代-1,2-二氢-4-羟基-2-氧-2-羟基-3-喹啉羧酸酯和4-羟基-1-甲基-3-硝基-2-（1 H）喹啉酮导致形成相应的4-氯-2-喹诺酮。描述了它们与各种碳，氮，氧和硫亲核试剂的反应。
• 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 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.
• Shridhar, D. R.; Sastry, C. V. Reddy; Mehrotra, A. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 1, p. 59 - 61
  作者：Shridhar, D. R.、Sastry, C. V. Reddy、Mehrotra, A. K.、Nagarajan, R.、Lal, B.、Bhopale, K. K.

  DOI：——

  日期：——
• 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.