2-(4-methoxyphenyl)-2H-1,2,3-triazole | 68535-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxyphenyl)-2H-1,2,3-triazole
• 英文别名: 2-(4-Methoxyphenyl)-2H-1,2,3-triazole；2-(4-methoxyphenyl)triazole
• CAS: 68535-51-3
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: KTMCIQDKVIHVAY-UHFFFAOYSA-N

物化性质

• 沸点：
  320.5±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-2H-1,2,3-triazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-[1,2,3]三唑-2-基-苯酚
  参考文献：
  名称：

  N-terminal strategy (N1–N4) toward high performance liquid crystal materials

  摘要：

  Liquid crystal materials have a variety of applications in many fields such as display techniques as well as photonics and optics. However, only few design principles have been disclosed on liquid crystal materials with different N-heterocycles as the terminal groups, which hinder the development of the heterocyclic liquid crystals. Here, a strategy of molecular design for N-heterocyclic liquid crystal materials is reported. On the basis of this strategy, a series of convenient N-heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole were applied to synthesize the novel liquid crystals. Most of them have proved to exhibit good mesomorphic behaviors which make them excellent components in the mixture of the LCDs materials. The simple attachment of N-heterocyclic units to the liquid crystal molecules through a mild reaction condition will provide a good prospect for the design of N-heterocyclic liquid crystals. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.013
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-(4-methoxyphenyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  通过分子内N–N键的形成合成2-取代的1,2,3-三唑

  摘要：

  分子内ñ - ñ键的形成导致基于分子内的各种2-芳基-1,2,3-三唑ñ - ñ键的形成进行说明。该反应可能遵循分子内S N 2置换机制，三甲基铵部分是分子内N - N键形成的良好离去基团。

  DOI：

  10.1002/ejoc.201901519

文献信息

• Ruthenium-catalyzed 1,2,3-triazole directed intermolecular C–H amidation of arenes with sulfonyl azides
  作者：Xiaoyu Wang、Chen Zhang、Jue Li、Chong Jiang、Fu Su、Zhen Zhan、Li Hai、Zhonghua Chen、Yong Wu

  DOI：10.1039/c6ra14020c

  日期：——

  Synthesis of 2-(2H-1,2,3-triazole-2-yl)aniline derivatives from 2-aryl-1,2,3-triazoles and sulfonylazides through ruthenium-catalyzed intermolecular C–H amidation is achieved. This reaction provides an environmentally benign protocol for C–N bond formation, producing N2 gas as the sole byproduct. Yet a number of functionalities are well tolerated, obtaining the desired products in moderate to excellent

  通过钌催化的分子间CH键酰胺化反应，可以从2-芳基-1,2,3-三唑和磺酰叠氮化物合成2-（2 H -1,2,3-三唑-2-基）苯胺衍生物。该反应为C–N键的形成提供了一种环境友好的方案，可产生N 2气体作为唯一的副产物。然而，许多功能被很好地耐受，以中等至极好的产量获得了所需的产品。
• 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。
• Palladium-Catalyzed Ortho-Alkoxylation of 2-Aryl-1,2,3-triazoles
  作者：Suping Shi、Chunxiang Kuang

  DOI：10.1021/jo5008306

  日期：2014.7.3

  Palladium-catalyzed alkoxylation of 2-aryl-1,2,3-triazoles was described in the presence of various groups in the aromatic rings. In addition, some other directing groups of heterocycles containing nitrogen were explored.

  描述了在芳族环中存在各种基团的情况下钯催化的2-芳基-1,2,3-三唑的烷氧基化。此外，还研究了其他一些含氮杂环的导向基团。
• Palladium-Catalyzed 2<i>H</i>-1,2,3-Triazole-Directed Oxidative Alkoxylation of Arenes with Alcohols
  作者：Wenjuan Shi、Zhangjie Shi

  DOI：10.1002/cjoc.201400462

  日期：2014.10

  A palladium catalyzed ortho‐alkoxylation of aryl CH bond was accomplished with primary and secondary alcohols as alkoxylation reagents and with triazole as new directing group. This transformation has a good functional group tolerance and is not sensitive to moisture and air.

  钯催化的邻芳基C的-alkoxylation  H键用伯和仲醇烷氧基化作为试剂和与三唑新定向取代基来完成的。这种转变具有良好的官能团耐受性，并且对湿气和空气不敏感。
• Ruthenium‐Catalyzed <i>meta</i> ‐Selective C−H Nitration of Biologically Important Aryltetrazoles
  作者：Jian Chen、Tianle Huang、Xinrui Gong、Zhu‐Jun Yu、Yuesen Shi、Yu‐Hang Yan、Yang Zheng、Xuexin Liu、Guo‐Bo Li、Yong Wu

  DOI：10.1002/adsc.202000475

  日期：2020.7.29

  The first example of tetrazole‐directed meta‐selective C−H nitration is described. This transformation provided a straightforward approach for the synthesis of biologically important m‐nitroaryltetrazoles in moderate to excellent yields with good functional group compatibility. In addition, new metallo‐β‐lactamase inhibitors were obtained by further transformation of the synthesized m‐nitroaryltetrazoles

  四唑引导的第一例的元-选择性C-H硝化进行说明。这种转变提供了一种用于生物学上重要的合成直接的方法米以良好的官能团的相容性优异的产率-nitroaryltetrazoles在适中。此外，通过将合成的进一步转化获得的新金属- β内酰胺酶抑制剂米-nitroaryltetrazoles。