(4-chlorophenyl)-[2-(4-chlorophenyl)-4,5-diphenyltriazol-1-ium-1-yl]azanide | 159723-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4-chlorophenyl)-[2-(4-chlorophenyl)-4,5-diphenyltriazol-1-ium-1-yl]azanide
• CAS: 159723-99-6
• 化学式: C₂₆H₁₈Cl₂N₄
• 分子量: 457.362
• InChiKey: NWOKGBUULAFLKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)-[2-(4-chlorophenyl)-4,5-diphenyltriazol-1-ium-1-yl]azanide 以79%的产率得到
  参考文献：
  名称：

  Butler Richard N., OShea Donal F., J. Chem. Res. Synop, (1994) N 9, S 350-351

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzil-β-bis-(4-chlor-phenylhydrazon) 在 lead dioxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以65%的产率得到(4-chlorophenyl)-[2-(4-chlorophenyl)-4,5-diphenyltriazol-1-ium-1-yl]azanide
  参考文献：
  名称：

  One-Pot Synthesis of Fluorescent 2,5-Dihydro-1,2,3-triazine Derivatives from a Cascade Rearrangement Sequence in the Reactions of 1,2,3-Triazolium-1-aminide 1,3-Dipoles with Propiolate Esters

  摘要：

  The reactions of 1,2,3-triazolium-1-aminides 1 ( readily available from benzil bishydrazones) with propiolate esters leads to fluorescent 2,5-dihydro-1,2,3-triazine derivatives 2, 3 in one pot. These synthetic reactions can be carried out in acetone, in water, or under solvent-free conditions. The reactions involve a Huisgen cycloaddition followed by a sequence of rearrangements. The final ring-expansion step was blocked by linking a six-methylene hydrocarbon chain between the prospective 1,2,3-triazine C-4 and C-6 atoms, using substrate 8 which gave the fused tricyclic azapropellane product 9 exclusively. X-ray crystal structures were determined for two 2,5-dihydro-1,2,3-triazine derivatives and for compound 9. The UV absorption of the 1,2,3-triazine derivatives showed a dual absorption at ca. 310 and ca. 390 nm with fluorescent emission at ca. 480 and 528 nm ( for excitation at 317 nm). The significant Stokes shift of ca. 200 nm shows the potential for biological fluorescent labeling experiments.

  DOI：

  10.1021/jo060752x

文献信息

• New reactive fluorophores in the 1,2,3-triazine series
  作者：Richard N. Butler、Aoife M. Fahy、Anthony Fox、John C. Stephens、P. McArdle、D. Cunningham、Alan G. Ryder

  DOI：10.1016/j.tetlet.2006.01.052

  日期：2006.3

  A one-pot synthesis of new fluorescent 2,5-dihydro-1,2,3-triazines with reactive functional groups and a large Stokes shift of 200 nm is described.

  一锅合成的新型荧光2,5-二氢-1,2,3-三嗪具有反应性官能团和200nm的大斯托克斯位移的描述。