2-(4'-hydroxy-1,1'-(2-biphenyl))-4-(4-hydroxyphenyl)-2H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4'-hydroxy-1,1'-(2-biphenyl))-4-(4-hydroxyphenyl)-2H-1,2,3-triazole
• 英文别名: 4-[2-[4-(4-Hydroxyphenyl)triazol-2-yl]phenyl]phenol；4-[2-[4-(4-hydroxyphenyl)triazol-2-yl]phenyl]phenol
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: YYCMMLUOMFMWGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-iodo-2-(2-iodophenyl)-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92%的产率得到2-(4'-hydroxy-1,1'-(2-biphenyl))-4-(4-hydroxyphenyl)-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

• 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.