ethyl 4-(bromoacetyl)-5-methyl-1-(4-chlorophenyl)-1H-pyrazole-3-carboxylate | 1260400-18-7

• 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-(bromoacetyl)-5-methyl-1-(4-chlorophenyl)-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 4-(bromoacetyl)-1-(4-chlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate；Ethyl 4-(bromoacetyl)-1-(4-chlorophenyl)-5-methyl-1h-pyrazole-3-carboxylate；ethyl 4-(2-bromoacetyl)-1-(4-chlorophenyl)-5-methylpyrazole-3-carboxylate
• CAS: 1260400-18-7
• 化学式: C₁₅H₁₄BrClN₂O₃
• 分子量: 385.645
• InChiKey: WLQKJMOSQTVZLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 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：

  邻羟基苯甲腈 、 ethyl 4-(bromoacetyl)-5-methyl-1-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以76%的产率得到3-methyl-2-(4-chlorophenyl)benzofuro[3,2-b]-pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione
  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：

  ethyl 4-acetyl-1-(4-chlorophenyl)-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95%的产率得到ethyl 4-(bromoacetyl)-5-methyl-1-(4-chlorophenyl)-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

文献信息

• 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.