ethyl 4-formyl-1-(3-methylphenyl)-1H-pyrazole-3-carboxylate | 1156510-02-9

• 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-formyl-1-(3-methylphenyl)-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 4-formyl-1-(M-tolyl)-1H-pyrazole-3-carboxylate；ethyl 4-formyl-1-(3-methylphenyl)pyrazole-3-carboxylate
• CAS: 1156510-02-9
• 化学式: C₁₄H₁₄N₂O₃
• mdl: MFCD11559141
• 分子量: 258.277
• InChiKey: IJXAQVARZPSNSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 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-formyl-1-(3-methylphenyl)-1H-pyrazole-3-carboxylate 在 盐酸 、 水 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2-(3-methylphenyl)-7-oxo-2,7-dihydrothiopyrano[3,4-c]pyrazole-5-carboxylic acid
  参考文献：
  名称：

  2 H-噻吩并[3,4-c]吡唑-7-一衍生物的合成作为新的杂环体系的第一个实例

  摘要：

  摘要结果获得了一系列的4-[（Z）-（4-氧代-2-硫代氧代-1,3-噻唑烷-5-亚甲基）甲基] -1-芳基-1 H-吡唑-3-羧酸乙酯4-甲酰基-1-芳基-1 H-吡唑-3-羧酸乙酯与若丹宁的反应 在NaOH的作用下，制得的吡唑-3-羧酸酯经过再循环形成2-芳基-7-氧代-2,7-二氢硫代吡喃并[3,4- c ]吡唑-5-羧酸，这是新杂环的第一个代表系统。

  DOI：

  10.1134/s1070363220070257
• 作为产物：
  描述：

  ethyl 2-[(3-methylphenyl)hydrazono]propionate 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 5.0h， 以73%的产率得到ethyl 4-formyl-1-(3-methylphenyl)-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

• 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.
• Synthesis of 2H-Thiopirano[3,4-c]pyrazol-7-one Derivatives as the First Example a New Heterocyclic System
  作者：T. I. Chaban、Y. E. Matiichuk、V. S. Matiychuk

  DOI：10.1134/s1070363220070257

  日期：2020.7

  rhodanine. Under the action of NaOH, the prepared pyrazole-3-carboxylates underwent recyclization to form 2-aryl-7-oxo-2,7-dihydrothiopyrano[3,4-c]pyrazole-5-carboxylic acids—the first representatives of new heterocyclic system.

  摘要结果获得了一系列的4-[（Z）-（4-氧代-2-硫代氧代-1,3-噻唑烷-5-亚甲基）甲基] -1-芳基-1 H-吡唑-3-羧酸乙酯4-甲酰基-1-芳基-1 H-吡唑-3-羧酸乙酯与若丹宁的反应 在NaOH的作用下，制得的吡唑-3-羧酸酯经过再循环形成2-芳基-7-氧代-2,7-二氢硫代吡喃并[3,4- c ]吡唑-5-羧酸，这是新杂环的第一个代表系统。