1-(2,6-dimethylphenyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole | 1575814-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,6-dimethylphenyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole
• 英文别名: 1-(2,6-Dimethylphenyl)-4-(4-fluorophenyl)triazole；1-(2,6-dimethylphenyl)-4-(4-fluorophenyl)triazole
• CAS: 1575814-70-8
• 化学式: C₁₆H₁₄FN₃
• 分子量: 267.306
• InChiKey: ARCONCWTDNHLPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯乙炔 、 1,3-二甲基-2-叠氮基苯 在 C₃₉H₄₄ClCuN₂⁽¹⁺⁾ 作用下， 以 neat (no solvent) 为溶剂， 反应 7.0h， 以93%的产率得到1-(2,6-dimethylphenyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  单击化学中异常的N-杂环碳-铜（I）配合物

  摘要：

  AbstractHerein we report the synthesis of a copper(I) chloro complex using an abnormal N‐heterocyclic carbene (aNHC) salt, 1,3‐bis(2,6‐diisopropylphenyl)‐2,4‐diphenylimidazolium. The CuCl(aNHC) complex efficiently catalyzed Huisgen 1,3‐dipolar cycloaddition reactions (click reactions) of azides with alkynes to give 1,4‐substituted 1,2,3‐triazoles in excellent yields at room temperature within short reaction time under solvent‐free conditions. The catalyst successfully activated benzyl azide and phenylacetylene under the low catalyst loading of 0.005 mol% resulting in a nearly quantitative yield of the product at room temperature with the high TON value of 19,800. The catalyst also exhibits high efficiency in the reaction between sterically hindered azides and alkynes under solvent‐free conditions at room temperature. Furthermore, a number of internal alkynes was successfully tested in this copper‐catalyzed cycloaddition reaction for synthesis of 4,5‐disubstituted triazoles.magnified image

  DOI：

  10.1002/adsc.201300343

文献信息

• An Abnormal N-Heterocyclic Carbene-Copper(I) Complex in Click Chemistry
  作者：Samaresh Chandra Sau、Sudipta Raha Roy、Tamal K. Sen、Dinesh Mullangi、Swadhin K. Mandal

  DOI：10.1002/adsc.201300343

  日期：2013.10.11

  AbstractHerein we report the synthesis of a copper(I) chloro complex using an abnormal N‐heterocyclic carbene (aNHC) salt, 1,3‐bis(2,6‐diisopropylphenyl)‐2,4‐diphenylimidazolium. The CuCl(aNHC) complex efficiently catalyzed Huisgen 1,3‐dipolar cycloaddition reactions (click reactions) of azides with alkynes to give 1,4‐substituted 1,2,3‐triazoles in excellent yields at room temperature within short reaction time under solvent‐free conditions. The catalyst successfully activated benzyl azide and phenylacetylene under the low catalyst loading of 0.005 mol% resulting in a nearly quantitative yield of the product at room temperature with the high TON value of 19,800. The catalyst also exhibits high efficiency in the reaction between sterically hindered azides and alkynes under solvent‐free conditions at room temperature. Furthermore, a number of internal alkynes was successfully tested in this copper‐catalyzed cycloaddition reaction for synthesis of 4,5‐disubstituted triazoles.magnified image