1-phenyl-5-(2,4-dichlorophenyl)-pyrazole-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-5-(2,4-dichlorophenyl)-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate；Ethyl 5-(2,4-dichlorophenyl)-1-phenylpyrazole-3-carboxylate；ethyl 5-(2,4-dichlorophenyl)-1-phenylpyrazole-3-carboxylate
• 化学式: C₁₈H₁₄Cl₂N₂O₂
• 分子量: 361.227
• InChiKey: DSIXXSHUCSJHOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲酰氯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 3.0h， 生成 1-phenyl-5-(2,4-dichlorophenyl)-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  N-甲氧基-N-甲基-β-烯氨基酮酸酯的合成：用于杂环化合物的区域选择性合成的新的合成前体。

  摘要：

  [结构：见正文]温氏酰胺与丙酸乙酯的乙炔锂或乙炔酸钠按迄今未开发的酰基取代共轭物加成序列反应，制得（E）-N-甲氧基-N-甲基-β-烯氨基酮酸酯。这种方法通过微波辅助反应中与肼的区域选择性环缩合，为稠密官能化的杂环化合物（包括吡唑）提供了多样化的入口。

  DOI：

  10.1021/ol0611088

文献信息

• Synthesis and Biological Evaluation of vicinal-Diaryl Pyrazole Ethyl Carboxylate Analogs as Antiproliferative Agent against Pancreatic Cancer
  作者：Sandeep Singh、Rajeev Kumar Sharma、Aishwarya Singh、Manoj Garg、R. Ramajayam

  DOI：10.14233/ajchem.2024.31173

  日期：——

  vicinal Diaryl scaffold possessing various heterocycles displayed versatile pharmacological activities ranging from antibacterial to antiviral. Herein, the synthesis of novel vicinal diaryl pyrazole ethyl carboxylate analogs as central ring and evaluated for their antiproliferative activity against pancreatic cancer line, PANC-1. Among the synthesized 27 compounds, six compounds displayed the IC50 value for antiproliferative activity in single digit micromolar. The cytotoxicity results of the synthesized compounds especially compound 25 (IC50 = 4.8 µM) confirms that these analogs may require further investigation.
• Synthesis of <i>N</i>-Methoxy-<i>N</i>-methyl-β-enaminoketoesters:  New Synthetic Precursors for the Regioselective Synthesis of Heterocyclic Compounds
  作者：Tobias Persson、John Nielsen

  DOI：10.1021/ol0611088

  日期：2006.7.1

  Weinreb amides react with the lithium or sodium acetylide of ethyl propynoate in a hitherto unexplored acyl substitution-conjugate addition sequence to furnish (E)-N-methoxy-N-methyl-beta-enaminoketoesters. This approach provides a diverse entry to densely functionalized heterocyclic compounds, including pyrazoles through regioselective cyclocondensations with hydrazines in a microwave-assisted reaction

  [结构：见正文]温氏酰胺与丙酸乙酯的乙炔锂或乙炔酸钠按迄今未开发的酰基取代共轭物加成序列反应，制得（E）-N-甲氧基-N-甲基-β-烯氨基酮酸酯。这种方法通过微波辅助反应中与肼的区域选择性环缩合，为稠密官能化的杂环化合物（包括吡唑）提供了多样化的入口。