5-methyl-2H-pyrazole-3,4-dione 4-[(4-chloro-phenyl)-hydrazone] | 65855-07-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-methyl-2H-pyrazole-3,4-dione 4-[(4-chloro-phenyl)-hydrazone]
• 英文别名: 4-[2-(4-chlorophenyl)hydrazinyl]-5-methylpyrazol-3-one
• CAS: 65855-07-4
• 化学式: C₁₀H₉ClN₄O
• mdl: MFCD01100110
• 分子量: 236.661
• InChiKey: CRYHRTAQLCEOEN-UHFFFAOYSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.85
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-methyl-2H-pyrazole-3,4-dione 4-[(4-chloro-phenyl)-hydrazone] 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以93%的产率得到4-(4-chlorophenylazo)-5-methyl-2,4-dihydropyrazole-3-thione
  参考文献：
  名称：

  Reactions of 5-mercaptoazoles and pyridine-2-thiones with acetylenic esters. Selectivity of the formation of novel fused thiazin-4-ones and thiazolidin-4-ones

  摘要：

  对乙酰二羧酸二甲酯（DMAD）和丙炔酸甲酯与 5-巯基唑和吡啶-2-硫酮的反应进行了系统研究，结果发现：6a,b、吡唑并[1,5-b]噻嗪-4-酮 15a-f、咪唑并[1,5-b]噻唑-4-酮 7a,b 和噻唑并[3,2-a]吡啶 21a-c。已经确定了起始 "环状 "硫代酰胺环的大小对反应产物中融合环大小的影响。在 5-巯基偶氮唑的反应中，优先形成的是六元噻嗪环。相反，五元噻唑烷环是在吡啶-2-硫酮的反应中形成的。在这两种情况下，产物都是一个与六元杂环融合的五元环。

  DOI：

  10.1039/b207854f
• 作为产物：
  描述：

  ethyl 2-(4-chlorophenylhydrazono)-3-oxobutyrate 在 aluminum oxide 、 一水合肼 、 N,N-二甲基甲酰胺 作用下， 反应 0.03h， 生成 5-methyl-2H-pyrazole-3,4-dione 4-[(4-chloro-phenyl)-hydrazone]
  参考文献：
  名称：

  Synthesis of novel mannich bases containing Pyrazolones and indole systems

  摘要：

  Novel mannich bases 7 a-h were synthesized the condensation reaction between 3-Methyl-5-oxo-4-(4'-phenyl hydrazono)-4,5-dihydro-pyrazol-1-yl]acetic acid hydrazide 4 With Isatin yielded the corresponding [3-Methyl-5-oxo-4-(4'-substituted aryl hydrazono)-4,5-dihydro-pyrazol-1-yl]-acetic acid(2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazide 6, this was subjected to mannich reaction with cyclic secondary amines in the presence of formaldehyde in DMF to give corresponding hydrazide 7 in excellent yields. The structures of these newly synthesized compounds were characterized by (1)H-NMR, Mass, IR and elemental analysis.

  DOI：

  10.1515/hc.2009.15.6.443

文献信息

• Synthesis of novel mannich bases containing Pyrazolones and indole systems
  作者：L.K. Ravindranath、K. Srikanth、M. Dastagiri Ready、S. D. Ishrath Begum

  DOI：10.1515/hc.2009.15.6.443

  日期：2009.1

  Novel mannich bases 7 a-h were synthesized the condensation reaction between 3-Methyl-5-oxo-4-(4'-phenyl hydrazono)-4,5-dihydro-pyrazol-1-yl]acetic acid hydrazide 4 With Isatin yielded the corresponding [3-Methyl-5-oxo-4-(4'-substituted aryl hydrazono)-4,5-dihydro-pyrazol-1-yl]-acetic acid(2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazide 6, this was subjected to mannich reaction with cyclic secondary amines in the presence of formaldehyde in DMF to give corresponding hydrazide 7 in excellent yields. The structures of these newly synthesized compounds were characterized by (1)H-NMR, Mass, IR and elemental analysis.
• Reactions of 5-mercaptoazoles and pyridine-2-thiones with acetylenic esters. Selectivity of the formation of novel fused thiazin-4-ones and thiazolidin-4-ones
  作者：Vasiliy A. Bakulev、Vera S. Berseneva、Natalia P. Belskaia、Yury Yu. Morzherin、Andreiy Zaitsev、Wim Dehaen、Ingrid Luyten、Suzanne Toppet

  DOI：10.1039/b207854f

  日期：2003.12.19

  A systematic study of the reactions of dimethyl acetylenedicarboxylate (DMAD) and methyl propynoate with 5-mercaptoazoles and pyridine-2-thiones has been carried out and as a result, a number of novel imidazo[1,5-b]thiazin-4-ones 6a,b, pyrazolo[1,5-b] thiazin-4-ones 15a–f, imidazo[1,5-b]thiazol-4-ones 7a,b and thiazolo[3,2-a]pyridines 21a–c have been prepared. The influence of the size of the ring of the starting “cyclic” thioamides on the size of the fused ring in the reaction products has been established. The preferred formation of a six-membered thiazine ring took place in the reactions of 5-mercaptoazoles. In contrast, the five membered thiazolidine ring is formed in reactions of pyridine-2-thiones. In both cases the product is a five-membered ring fused to a six-membered heterocycle.

  对乙酰二羧酸二甲酯（DMAD）和丙炔酸甲酯与 5-巯基唑和吡啶-2-硫酮的反应进行了系统研究，结果发现：6a,b、吡唑并[1,5-b]噻嗪-4-酮 15a-f、咪唑并[1,5-b]噻唑-4-酮 7a,b 和噻唑并[3,2-a]吡啶 21a-c。已经确定了起始 "环状 "硫代酰胺环的大小对反应产物中融合环大小的影响。在 5-巯基偶氮唑的反应中，优先形成的是六元噻嗪环。相反，五元噻唑烷环是在吡啶-2-硫酮的反应中形成的。在这两种情况下，产物都是一个与六元杂环融合的五元环。