4-(Naphthalen-1-yl)-5-(trimethylsilyl)-2H-1,2,3-triazole | 84645-35-2

• 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-(Naphthalen-1-yl)-5-(trimethylsilyl)-2H-1,2,3-triazole
• 英文别名: trimethyl-(5-naphthalen-1-yl-2H-triazol-4-yl)silane
• CAS: 84645-35-2
• 化学式: C₁₅H₁₇N₃Si
• 分子量: 267.406
• InChiKey: PTZKCFCWFOTERD-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  427.9±33.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(Naphthalen-1-yl)-5-(trimethylsilyl)-2H-1,2,3-triazole 、 phenyl(2,4,6-trimethoxyphenyl)iodonium trifluoroacetate 在 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到4-(naphthalen-1-yl)-2-phenyl-5-(trimethylsilyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts

  摘要：

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.

  DOI：

  10.1021/acs.orglett.9b02140
• 作为产物：
  描述：

  1-(1-萘基)-2-(三甲基硅基)乙炔 在 叠氮基三甲基硅烷 作用下， 以62%的产率得到4-(Naphthalen-1-yl)-5-(trimethylsilyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts

  摘要：

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.

  DOI：

  10.1021/acs.orglett.9b02140

文献信息

• Catalyst and solvent free microwave-assisted synthesis of substituted 1,2,3-triazoles
  作者：Sahar Roshandel、Suresh C. Suri、Jacob C. Marcischak、Golam Rasul、G. K. Surya Prakash

  DOI：10.1039/c8gc01516c

  日期：——

  report a microwave-assisted catalyst and solvent free synthesis of 1,2,3-triazoles through the cycloaddition of trimethylsilylazide and acetylenes. Utilization of a thermally stable azide source, elimination of a metal catalyst, solvent or any additives, and a convenient isolation procedure result in an overall greener approach to access 1,2,3-triazoles on a practical scale with good to excellent yields

  我们报告了通过三甲基甲硅烷基叠氮化物和乙炔的环加成反应的微波辅助催化剂和1,2,3-三唑的无溶剂合成。利用热稳定的叠氮化物源，消除金属催化剂，溶剂或任何添加剂以及方便的分离程序，可以从整体上以更绿色的方式实际获得1,2,3-三唑，并具有良好或优异的收率（55）。 –99％）。
• Aoyama, Toyohiko; Sudo, Kimio; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 10, p. 3849 - 3851
  作者：Aoyama, Toyohiko、Sudo, Kimio、Shioiri, Takayuki

  DOI：——

  日期：——
• AOYAMA, TOYOHIKO;SUDO, KIMIO;SHIOIRI, TAKAYUKI, CHEM. AND PHARM. BULL., 1982, 30, N 10, 3849-3851
  作者：AOYAMA, TOYOHIKO、SUDO, KIMIO、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——
• Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts
  作者：Sahar Roshandel、Maiko J. Lunn、Golam Rasul、Daniel Sylvinson Muthiah Ravinson、Suresh C. Suri、G. K. Surya Prakash

  DOI：10.1021/acs.orglett.9b02140

  日期：2019.8.16

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.