5-methoxycarbonyl-5H-2,4,6-triphenyl-2,5-dihydro-1,2,3-triazine | 132545-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxycarbonyl-5H-2,4,6-triphenyl-2,5-dihydro-1,2,3-triazine
• 英文别名: 5-methoxycarbonyl-2,4,6-triphenyl-2,5-dihydro-1,2,3-triazine；methyl 2,4,6-triphenyl-5H-triazine-5-carboxylate
• CAS: 132545-09-6
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: GFAOUDBZBOUVLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4,5-triphenyl-1,2,3-triazolium 1-phenyl-aminide 以 乙醇 、 丙酮 为溶剂， 反应 192.0h， 生成 5-methoxycarbonyl-5H-2,4,6-triphenyl-2,5-dihydro-1,2,3-triazine
  参考文献：
  名称：

  1,2,3-三嗪系列的新型反应性荧光团

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2006.01.052

文献信息

• 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
  作者：Richard N. Butler、Aoife M. Fahy、Anthony Fox、John C. Stephens、P. McArdle、D. Cunningham、A. Ryder

  DOI：10.1021/jo060752x

  日期：2006.7.1

  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.
• Butler, Richard N.; Cunningham, Desmond; Marren, Elizabeth G., Journal of the Chemical Society. Perkin transactions I, 1990, # 12, p. 3321 - 3326
  作者：Butler, Richard N.、Cunningham, Desmond、Marren, Elizabeth G.、McArdle, Patrick

  DOI：——

  日期：——
• BUTLER, RICHARD N.;CUNNINGHAM, DESMOND;MARREN, ELIZABETH G.;MCARDLE, PATR+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N2, C. 3321-3326
  作者：BUTLER, RICHARD N.、CUNNINGHAM, DESMOND、MARREN, ELIZABETH G.、MCARDLE, PATR+

  DOI：——

  日期：——