ethyl 4-acetyl-1-(4-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate | 63514-82-9

• 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-acetyl-1-(4-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate
• 英文别名: 4-acetyl-1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；ethyl 4-acetyl-1-(4-chlorophenyl)-5-methylpyrazole-3-carboxylate
• CAS: 63514-82-9
• 化学式: C₁₅H₁₅ClN₂O₃
• mdl: MFCD06809098
• 分子量: 306.749
• InChiKey: UJYFUYAQSSKJNG-UHFFFAOYSA-N

物化性质

• 熔点：
  91 °C(Solv: ethanol (64-17-5))
• 沸点：
  449.3±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

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-(4-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79%的产率得到2-p-Chlorphenyl-3,4-dimethylpyrazolo<3,4-d>pyridazin-6H-7-on
  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：

  乙酰丙酮 、 (Z)-ethyl 2-chloro-2-(2-(4-chlorophenyl)hydrazono)acetate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以57%的产率得到ethyl 4-acetyl-1-(4-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

• Convenient and Efficient Method for Synthesis of Bis-Hetaryl Ketones and Evaluation of Their Antimicrobial Activity
  作者：Abdou O. Abdelhamid、Sobhi M. Gomha、Waleed A. M. A. El-Enany

  DOI：10.1002/jhet.3415

  日期：2019.2

  Sodium 1‐aryl‐3‐(3‐(ethoxycarbonyl)‐5‐methyl‐1H‐pyrazol‐4‐yl)‐3‐oxoprop‐1‐en‐1‐olate was used as precursor for the preparation of some novel derivatives of various fused azolotriazine ring systems via coupling reactions with hetaryldiazonium salts. Hydrazinolysis of the latter products yielded the corresponding pyrazolopyridazine derivatives. The structures of the products were established by their

  1-芳基-3-（3-（乙氧基羰基）-5-甲基-1 H-吡唑-4-基）-3-氧代丙-1-烯-1-油酸钠被用作制备某些新型衍生物的前体通过与杂芳基重氮盐的偶联反应制备各种稠合的三唑三嗪环系统。后一种产物的水合肼解反应产生相应的吡唑并哒嗪衍生物。产品的结构是通过其光谱数据和元素分析确定的。还评估了一些新产品的抗菌和抗真菌活性。
• In Situ Generation of Nitrilimines from Aryldiazonium Salts and Diazo Esters: Synthesis of Fully Substituted Pyrazoles under Room Temperature
  作者：Ying Shao、Hao Zheng、Junfeng Qian、Xiaobing Wan

  DOI：10.1021/acs.orglett.8b00750

  日期：2018.4.20

  A novel one-pot synthesis for fully substituted pyrazoles has been well developed via the in situ generation of nitrilimines from aryldiazonium salts and diazo esters and a subsequent cycloaddition with 1,3-dicarbonyl compounds. High yields, mild conditions, wide substrate scope, and operational simplicity are the significant advantages of this methodology.

  通过从芳基重氮盐和重氮酯原位生成腈亚胺以及随后与1,3-二羰基化合物进行环加成反应，已开发出一种完全取代的吡唑的新型一锅合成方法。高产率，温和的条件，广泛的底物范围和操作简便性是该方法的显着优势。
• Efficient Synthesis and Antimicrobial Evaluation of New Azolopyrimidines‐Bearing Pyrazole Moiety
  作者：Abdou O. Abdelhamid、Sobhi M. Gomha、Waleed A. M. A. El‐Enany

  DOI：10.1002/jhet.3638

  日期：2019.9

  enone derivatives was used as a precursor for synthesis of various fused azolopyrimidine ring systems as pyrazolopyrimidines, triazolopyrimidines, and pyrimidobenzimidazoles following many procedures. The identity of the prepared compounds was elucidated by their spectral data and elemental analyses. The in vitro antimicrobial activity of 13 new compounds was evaluated, and many derivatives showed

  使用3-羟基-1-（1-芳基-5-甲基吡唑基）丙烯酮衍生物的钠盐作为前体，可以按照许多步骤合成各种稠合的偶氮嘧啶环系统，如吡唑并嘧啶，三唑并嘧啶和嘧啶并苯并咪唑。通过其光谱数据和元素分析阐明了所制备化合物的身份。在体外的13种新的化合物的抗微生物活性进行了评价，并且许多衍生物显示出优良至适中的活性。
• 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 and Anticancer Activity of 2-Aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione and 2-Aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones
  作者：T. I. Chaban、Y. E. Matiichuk、V. Ya. Horishny、I. G. Chaban、V. S. Matiychuk

  DOI：10.1134/s1070428020050139

  日期：2020.5

  The reactions of ethyl 1-aryl-4-(2-bromoacetyl)-5-methyl-1H-pyrazolocarboxylates withortho-hydroxybenzonitrile and 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile gave previously unknown 2-aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones and 2-aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones, respectively. It was found that this reaction occurred as a tandem process. The synthesized compounds were sceened for anticancer activity and exhibited moderate activity against the most part of malignant cancer cells.