4-iodo-2-phenyl-2H-[1,2,3]triazole | 959072-08-3

• 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-iodo-2-phenyl-2H-[1,2,3]triazole
• 英文别名: 4-iodo-2-phenyl-2H-1,2,3-triazole；2-Phenyl-4-iodo-1,2,3-triazole；4-iodo-2-phenyltriazole
• CAS: 959072-08-3
• 化学式: C₈H₆IN₃
• 分子量: 271.06
• InChiKey: XVUXIODMXXNUMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-苯基-2H- 1,2,3-三氮唑 在 dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以56%的产率得到4-iodo-2-(2-iodophenyl)-2H-[1,2,3]triazole
  参考文献：
  名称：

  Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

  摘要：

  通过环化相应的glyoxal arylsazone（由商业化的aryldrazine生成）合成了2-芳基-1,2,3-三氮唑。尝试使用不同的2,2,6,6-四甲基哌啶基混合锂-金属（Zn、Cd、Cu、Co、Fe）组合进行2-苯基-1,2,3-三氮唑的去质子金属化，在Zn、Cd和Cu的情况下得到了结果。接着选择锂-锌组合，将去质子化-碘化序列应用于所有合成的2-芳基-1,2,3-三氮唑。借助DFT B3LYP方法在THF溶液中测定的底物CH酸度，对结果进行了分析。

  DOI：

  10.1039/c2ob25554e

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.
• Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles
  作者：Floris Chevallier、Thomas Blin、Elisabeth Nagaradja、Frédéric Lassagne、Thierry Roisnel、Yury S. Halauko、Vadim E. Matulis、Oleg A. Ivashkevich、Florence Mongin

  DOI：10.1039/c2ob25554e

  日期：——

  2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium–metal (Zn, Cd, Cu, Co, Fe) combinations, giving results in the case of Zn, Cd, and Cu. The lithium–zinc combination was next selected to apply the deprotonation–iodination sequence to all the 2-aryl-1,2,3-triazoles synthesized. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method.

  通过环化相应的glyoxal arylsazone（由商业化的aryldrazine生成）合成了2-芳基-1,2,3-三氮唑。尝试使用不同的2,2,6,6-四甲基哌啶基混合锂-金属（Zn、Cd、Cu、Co、Fe）组合进行2-苯基-1,2,3-三氮唑的去质子金属化，在Zn、Cd和Cu的情况下得到了结果。接着选择锂-锌组合，将去质子化-碘化序列应用于所有合成的2-芳基-1,2,3-三氮唑。借助DFT B3LYP方法在THF溶液中测定的底物CH酸度，对结果进行了分析。