4-(4-hydroxyphenyl)-2-phenyl-2H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-hydroxyphenyl)-2-phenyl-2H-1,2,3-triazole
• 英文别名: 4-(2-Phenyltriazol-4-yl)phenol；4-(2-phenyltriazol-4-yl)phenol
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: CTICJBLHDSADTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-iodo-2-phenyl-2H-[1,2,3]triazole 、 4-羟基苯硼酸 在 sodium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 24.0h， 以98%的产率得到4-(4-hydroxyphenyl)-2-phenyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Deprotometalation–iodolysis and computed CH acidity of 1,2,3- and 1,2,4-triazoles. Application to the synthesis of resveratrol analogues

  摘要：

  1-Aryl-and 2-aryl-1,2,3-triazoles were synthesized by N-arylation of the corresponding azoles using aryl iodides. The deprotometalations of 1-phenyl-1,2,3-triazole and -1,2,4-triazole were performed using a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination and occurred at the most acidic site, affording by iodolysis the 5-substituted derivatives. Dideprotonation was noted from 1-(2-thienyl)-1,2,4-triazole by increasing the amount of base. From 2-phenyl-1,2,3-triazoles, and in particular from 2-(4-trifluoromethoxy) phenyl-1,2,3-triazole, reactions at the 4 position of the triazolyl, but also ortho to the triazolyl on the phenyl group, were observed. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method. 4-Iodo-2-phenyl-1,2,3-triazole and 4-iodo-2-(2-iodophenyl)-1,2,3-triazole were next involved in Suzuki coupling reactions to furnish the corresponding 4-arylated and 4,2'-diarylated derivatives. When evaluated for biological activities, the latter (which are resveratrol analogues) showed moderate antibacterial activity and promising antiproliferative effect against MDA-MB-231 cell line. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.031

文献信息

• Simple and Efficient One‐Pot Synthesis of 2,4‐Diaryl‐1,2,3‐triazoles
  作者：Wen‐Jie Tang、Yong‐Zhou Hu

  DOI：10.1080/00397910600781216

  日期：2006.8.1

  Abstract A general and efficient method for the preparation of 2,4‐diaryl‐1,2,3‐triazoles from α‐hydroxyacetophenones and phenylhydrazines is reported. The essential characteristics of this method include mild reaction conditions, a straightforward workup procedure, and comparatively higher yields.

  摘要 报道了一种从 α-羟基苯乙酮和苯肼制备 2,4-二芳基-1,2,3-三唑的通用且有效的方法。这种方法的基本特征包括温和的反应条件、简单的后处理程序和相对较高的收率。
• Deprotometalation–iodolysis and computed CH acidity of 1,2,3- and 1,2,4-triazoles. Application to the synthesis of resveratrol analogues
  作者：Elisabeth Nagaradja、Ghenia Bentabed-Ababsa、Mathieu Scalabrini、Floris Chevallier、Stéphanie Philippot、Stéphane Fontanay、Raphaël E. Duval、Yury S. Halauko、Oleg A. Ivashkevich、Vadim E. Matulis、Thierry Roisnel、Florence Mongin

  DOI：10.1016/j.bmc.2015.08.031

  日期：2015.10

  1-Aryl-and 2-aryl-1,2,3-triazoles were synthesized by N-arylation of the corresponding azoles using aryl iodides. The deprotometalations of 1-phenyl-1,2,3-triazole and -1,2,4-triazole were performed using a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination and occurred at the most acidic site, affording by iodolysis the 5-substituted derivatives. Dideprotonation was noted from 1-(2-thienyl)-1,2,4-triazole by increasing the amount of base. From 2-phenyl-1,2,3-triazoles, and in particular from 2-(4-trifluoromethoxy) phenyl-1,2,3-triazole, reactions at the 4 position of the triazolyl, but also ortho to the triazolyl on the phenyl group, were observed. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method. 4-Iodo-2-phenyl-1,2,3-triazole and 4-iodo-2-(2-iodophenyl)-1,2,3-triazole were next involved in Suzuki coupling reactions to furnish the corresponding 4-arylated and 4,2'-diarylated derivatives. When evaluated for biological activities, the latter (which are resveratrol analogues) showed moderate antibacterial activity and promising antiproliferative effect against MDA-MB-231 cell line. (C) 2015 Elsevier Ltd. All rights reserved.