ethyl 4-acetyl-1-(2-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate | 1156510-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-acetyl-1-(2-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 4-acetyl-1-(2-chlorophenyl)-5-methylpyrazole-3-carboxylate
• CAS: 1156510-05-2
• 化学式: C₁₅H₁₅ClN₂O₃
• 分子量: 306.749
• InChiKey: BWLINGOKZXYENL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-acetyl-1-(2-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以77%的产率得到2-(2-chlorophenyl)-3,4-dimethyl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-one
  参考文献：
  名称：

  Molecular design of pyrazolo[3,4-d]pyridazines

  摘要：

  Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R(2)(1)-6-R(2)-2-aryl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-ones (R(1), R(2) = H, Me) which were subjected to alkylation and sulfurization.

  DOI：

  10.1134/s1070428008090182
• 作为产物：
  描述：

  ethyl chloro[(2-chlorophenyl)hydrazono]acetate 、 乙酰丙酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以67%的产率得到ethyl 4-acetyl-1-(2-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Molecular design of pyrazolo[3,4-d]pyridazines

  摘要：

  Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R(2)(1)-6-R(2)-2-aryl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-ones (R(1), R(2) = H, Me) which were subjected to alkylation and sulfurization.

  DOI：

  10.1134/s1070428008090182

文献信息

• Synthesis and properties of ethyl 1-aryl-5-methyl-4-[1-(phenylhydrazinylidene)ethyl]-1H-pyrazole-3-carboxylates
  作者：M. A. Potopnyk、V. S. Matiichuk、M. D. Obushak

  DOI：10.1134/s1070428017010110

  日期：2017.1

  Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates reacted with phenylhydrazine to give the corresponding hydrazones, ethyl 1-aryl-5-methyl-4-[1-(phenylhydrazinylidene)ethyl]-1H-pyrazole-3-carboxylates, which were converted to ethyl 1'-aryl-4-formyl-5'-methyl-1-phenyl-1H,1'H-3,4'-bipyrazole-3'-carboxylates by treatment with the Vilsmeier-Haack reagent. No indole derivatives were formed from the same hydrazones under the Fischer reaction conditions, but cyclization to 2-aryl-3,4-dimethyl-6-phenyl-2,6-dihydro-7H- pyrazolo[3,4-d] pyridazin-7-ones was observed.
• Synthesis of 2-Aryl-4-(R-sulfanylmethyl)-3-methyl-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-7-ones
  作者：V. S. Matiichuk、M. A. Potopnyk、N. D. Obushak

  DOI：10.1134/s1070428010100192

  日期：2010.10

  Bromination of ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates gave ethyl 1-aryl-4-(bromoacetyl)-5-methyl-1H-pyrazol-3-carboxylates which were used to alkylate benzenethiol and heterocyclic thiones at the sulfur atom. Reactions of the resulting S-alkylation products with hydrazine or methylhydrazine involved closure of pyridazine ring to afford 2-aryl-3-methyl-4-[phenyl(or hetaryl)sulfanylmethyl]-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-7-ones.
• Molecular design of pyrazolo[3,4-d]pyridazines
  作者：V. S. Matiichuk、M. A. Potopnyk、N. D. Obushak

  DOI：10.1134/s1070428008090182

  日期：2008.9

  Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R(2)(1)-6-R(2)-2-aryl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-ones (R(1), R(2) = H, Me) which were subjected to alkylation and sulfurization.