ethyl 4-acetyl-1-(4-bromophenyl)-5-methyl-1H-pyrazole-3-carboxylate | 96734-86-0

• 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-bromophenyl)-5-methyl-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 4-acetyl-1-(4-bromophenyl)-5-methylpyrazole-3-carboxylate
• CAS: 96734-86-0
• 化学式: C₁₅H₁₅BrN₂O₃
• 分子量: 351.2
• InChiKey: FGTLYZTZFGFYQD-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-(4-bromophenyl)-5-methyl-1H-pyrazole-3-carboxylate 在 硫酸 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以77%的产率得到ethyl 4-(bromoacetyl)-1-(4-bromophenyl)-5-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070428020050139
• 作为产物：
  描述：

  4-溴苯胺 在 盐酸 、 sodium ethanolate 、 sodium acetate 、 sodium nitrite 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 18.0h， 生成 ethyl 4-acetyl-1-(4-bromophenyl)-5-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Bernard; Cocco; Maccioni, Farmaco, Edizione Scientifica, 1985, vol. 40, # 4, p. 259 - 271

  摘要：

  DOI：

文献信息

• 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。
• Albar, Hassan A., Journal of Chemical Research, Miniprint, 1999, # 3, p. 872 - 889
  作者：Albar, Hassan A.

  DOI：——

  日期：——
• Albar, Hassan A., Journal of Chemical Research, Miniprint, 1996, # 7, p. 1756 - 1764
  作者：Albar, Hassan A.

  DOI：——

  日期：——
• 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.
• Patel; Fernandes; Vyas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 10, p. 966 - 969
  作者：Patel、Fernandes、Vyas

  DOI：——

  日期：——