3-hydroxy-5-(4-methoxyphenyl)-4-phenyl-1-(2H-1,2,4-triazol-3-yl)-1H-pyrrol-2(5H)-one | 1093388-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-hydroxy-5-(4-methoxyphenyl)-4-phenyl-1-(2H-1,2,4-triazol-3-yl)-1H-pyrrol-2(5H)-one
• CAS: 1093388-56-7
• 化学式: C₁₉H₁₆N₄O₃
• 分子量: 348.361
• InChiKey: OLRZLBRHMFMCKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.34
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  7-hydroxy-5-(4-methoxyphenyl)-6-phenyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylic acid 在 溶剂黄146 作用下， 反应 0.67h， 生成 3-hydroxy-5-(4-methoxyphenyl)-4-phenyl-1-(2H-1,2,4-triazol-3-yl)-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity

  摘要：

  The multicomponent reactions of 3-amino-1,2,4-triazoles/5-aminotetrazole with phenylpyruvic acids and aromatic aldehydes were studied using conventional thermal heating, ultrasonification and microwave dielectric heating. Two different reaction pathways for these cyclocondensations occurring under either kinetic or thermodynamic control were established depending on the temperature regime and building block selection. In case of aminotriazoles, an unprecedented reaction pathway leading to 5-aryl-7-hydroxy-6-phenyl-4,5,6,7-tetrahydro [1,2,4]triazolol [1,5-a]pyrimidine-7-carboxylic acids was found and discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.089

文献信息

• Study of the Chemoselectivity of Multicomponent Heterocyclizations Involving 3-Amino-1,2,4-triazole and Pyruvic Acids as Key Reagents, and Biological Activity of the Reaction Products
  作者：Maryna V. Murlykina、Yana I. Sakhno、Sergey M. Desenko、Svetlana V. Shishkina、Oleg V. Shishkin、Dmytro O. Sysoiev、Maryna N. Kornet、Dominique Schols、Jan L. Goeman、Johan Van der Eycken、Erik V. Van der Eycken、Valentin A. Chebanov

  DOI：10.1002/ejoc.201500469

  日期：2015.7

  Three-component reactions involving 3-amino-1,2,4-triazole, aldehydes, including salicylic aldehydes, and pyruvic acids were studied in detail. The reaction pathway and products of the heterocyclizations could be changed by variation of the reaction parameters. The broad antimicrobial activity of the products was also studied. Compound 9d showed specific anti-influenza virus (A/H1N1) activity, with an IC50 of

  详细研究了涉及 3-氨基-1,2,4-三唑、醛（包括水杨醛）和丙酮酸的三组分反应。反应参数的变化可以改变杂环化的反应途径和产物。还研究了产品的广泛抗菌活性。化合物9d表现出特异性抗流感病毒（A/H1N1）活性，IC50为0.57 μ M，CC50 > 100 μ M。