4-((7-amino-5-(4-chlorophenyl)-6-cyano-2-hydroxypyrazolo[1,5-a]pyrimidin-3-yl)diazenyl)benzenesulfonamide | 1567848-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-((7-amino-5-(4-chlorophenyl)-6-cyano-2-hydroxypyrazolo[1,5-a]pyrimidin-3-yl)diazenyl)benzenesulfonamide
• CAS: 1567848-34-3
• 化学式: C₁₉H₁₃ClN₈O₃S
• 分子量: 468.883
• InChiKey: JZWRJFYMMIDFFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  185.11
• 氢给体数：
  3.0
• 氢受体数：
  10.0

文献信息

• Chemoselective Three Component Reactions of 3-Aminopyrazoles, Aldehydes and Malononitrile: Optimize the Structures and Compute the Energies of Possible Tautomers
  作者：Hassan Sheibani、Vahid Saheb、Marjan Rezaei、Mahboobeh Zahedifar

  DOI：10.2174/15701786113106660066

  日期：2014.1.31

  A chemoselective synthesis of 7-amino-5-aryl-2-hydroxy-3-(aryldiazenylpyrazolo[1,5-a]pyrimidine-6- carbonitriles and 4-((7-amino-6-cyano-2-hydroxy-5-arylpyrazolo[1,5-a]pyrimidine-3-yl)diazenyl)benzenesulfonamides through three-component reaction of 3-aminopyrazoles, aldehydes and malononitrile in the presence of base catalysts such as sodium acetate, pyridine and high surface area MgO is reported. 3-Amino pyrazoles were prepared by refluxing of ethyl(arylazo) cyanoacetates with hydrazine hydrate in ethanol. Structures of the new compounds were established by their spectral data and theoretical results. Density Functional Theory (DFT) calculations have been performed to optimize the structure of products. The theoretical results are in good agreement with experimental findings. The theoretical results are compared with the experimetal data. DFT calculations reveal that the enol form of 6 is the most stable molecule.

  通过 3-氨基吡唑、醛类和丙二腈三组分反应，化学选择性合成 7-氨基-5-芳基-2-羟基-3-(芳基偶氮基吡唑并[1,5-a]嘧啶-6-甲腈)和 4-((7-氨基-6-氰基-2-羟基-5-芳基吡唑并[1.5-a]嘧啶-3-基)偶氮基)苯磺酰胺、3-氨基吡唑、醛类和丙二腈在醋酸钠、吡啶和高比表面积氧化镁等碱催化剂存在下通过三组分反应制备的苯磺酰胺。3-Amino 吡唑是通过乙基（芳基偶氮）氰乙酸酯与水合肼在乙醇中的回流反应制备的。通过光谱数据和理论结果确定了新化合物的结构。为了优化产品的结构，还进行了密度泛函理论（DFT）计算。理论结果与实验结果十分吻合。理论结果与实验数据进行了比较。DFT 计算显示，6 的烯醇形式是最稳定的分子。