1,3-diphenyl-5-vinyl-1,2,4-triazole | 115591-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-diphenyl-5-vinyl-1,2,4-triazole
• 英文别名: 1,3-diphenyl-5-vinyl-1H-1,2,4-triazole；1H-1,2,4-Triazole, 5-ethenyl-1,3-diphenyl-；5-ethenyl-1,3-diphenyl-1,2,4-triazole
• CAS: 115591-23-6
• 化学式: C₁₆H₁₃N₃
• 分子量: 247.299
• InChiKey: JGDZCNWXTIDCSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  1,3-diphenyl-5-vinyl-1,2,4-triazole 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 生成 5-乙基-1,3-二苯基-1,2,4-三唑
  参考文献：
  名称：

  Formation of 1,2,4-triazoles by cation radical-induced oxidative addition of arylhydrazones of benzaldehyde and butyraldehyde to nitriles

  摘要：

  DOI：

  10.1021/jo00253a029
• 作为产物：
  描述：

  α-chlorobenzaldehyde phenylhydrazone 在 TEA 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1,3-diphenyl-5-vinyl-1,2,4-triazole
  参考文献：
  名称：

  Cyclization of 1,2,4-triazenes to 1,2,4-triazoles using oxidizing reagents—NaClO, Ca(ClO)2, Dess–Martin periodinane and Ley's TPAP/NMO

  摘要：

  A simple and efficient approach to 1,3,5-trisubstituted 1,2,4-triazoles via cyclization of 1,2,4-triazenes employing commonly used oxidizing agents such as NaClO, Ca(ClO)(2), Dess-Martin periodinane and Ley's oxidizing agent (TPAP/NMO) is described. The reaction proceeds under mild conditions and is compatible with various functional groups. Extension of this approach to prepare triazoles on solid support has also been investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00976-0

文献信息

• From imidates to vinyl-1,2,4-triazoles: Synthesis, mechanistic aspects and first issues of their reactivity
  作者：Safa Azzouni、Abderrahmen Abdelli、Anne Gaucher、Youssef Arfaoui、Mohamed Lotfi Efrit、Damien Prim

  DOI：10.1016/j.tet.2018.10.050

  日期：2018.12

  The method reveals selective towards 5-vinyl-1,2,4-triazoles avoiding the potential formation of seven- and five-membered side-products as supported by theoretical calculations and NMR experiments. First lines of Pd-catalyzed arylation of the vinyl fragment towards 5-styryl-1,2,4-triazoles and Cu-catalyzed arylation at the N(1) site are finally described.

  各种取代的酰基酰亚胺与肼衍生物的反应代表了向5-乙烯基-1，2，4-三唑衍生物的有效且易于设定的合成入口。三唑环的结构允许在五元杂环的N（1），C（3）和C（5）位置以高至高收率安装各种取代基组合。该方法揭示了对5-乙烯基-1,2,4-三唑的选择性，避免了理论计算和NMR实验支持的七元和五元副产物的潜在形成。最后描述了在N（1）位点上Pd催化的乙烯基片段朝5-styryl-1,2,4-三唑的芳基化和Cu催化的芳基化的第一行。
• Orthogonal arylations of 5-vinyl-1,2,4-triazoles
  作者：Safa Azzouni、Anne Gaucher、Damien Prim、Mohamed Lotfi Efrit

  DOI：10.1016/j.tet.2020.130954

  日期：2020.2

  described using selective orthogonal arylation sequences. Ligand free Pd-catalyzed arylation allowed installing various (het)aryl units exclusively at the vinyl fragment of N1 substituted or N1-H precursors. Successful double arylations starting from ortho, meta and para bisiodobenzenes led to extended bistriazolyl derivatives. In contrast, Cu-catalyzed arylation using pyridylmethylamine as the ligand

  使用选择性正交芳基化序列描述了1,3,5-三取代的1,2,4-三唑的制备。不含配体的Pd催化的芳基化反应可仅在N1取代或N1-H前体的乙烯基片段上安装各种（杂）芳基单元。从邻，间和对二碘代苯开始的成功双芳基化导致扩展的双三唑基衍生物。相反，使用吡啶基甲胺作为配体的Cu催化的芳基化反应导致N1芳基化的三唑保持乙烯基部分完整。芳构化过程与邻，间和对位的给电子基团相容位置和容许的吸电子基团程度较小。该策略是通用的，并在三唑核心扩散分子多样性。
• An electrochemical multicomponent [3 + 1 + 1] annulations to synthesize polysubstituted 1,2,4-triazoles
  作者：Zhiheng Zhao、Yonghui He、Ming Li、Jiazhe Xu、Xiangguang Li、Lizhu Zhang、Lijun Gu

  DOI：10.1016/j.tet.2021.132111

  日期：2021.5
• An Improved Synthesis of 1,2,4-Triazoles using Ag2CO3
  作者：K Paulvannan、Tao Chen、Ron Hale

  DOI：10.1016/s0040-4020(00)00726-2

  日期：2000.10

  An improved synthesis of 1,3,5-trisubstituted 1,2,4-triazoles via Ag2CO3 mediated cyclization of triazenes has been developed. This approach is flexible and compatible with a wide range of functional groups. The reaction was complete within 3 h and the products were isolated in moderate to high yields. The influence of the beta-substituents of the amines on the triazole formation was also studied. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SHINE, HENRY J.;MANSURUL, HOQUE A. K. M., J. ORG. CHEM., 53,(1988) N 18, C. 4349-4353
  作者：SHINE, HENRY J.、MANSURUL, HOQUE A. K. M.

  DOI：——

  日期：——