3,6-Di-(4-bromphenyl)-1,2-dihydro-1,2,4,5-tetrazin | 68614-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-Di-(4-bromphenyl)-1,2-dihydro-1,2,4,5-tetrazin
• 英文别名: 3,6-Bis-(p-brom-phenyl)-1,2-dihydro-1,2,4,5-tetrazin；3,6-bis-(4-bromo-phenyl)-1,2-dihydro-[1,2,4,5]tetrazine；3,6-Bis-(4-brom-phenyl)-1,2-dihydro-[1,2,4,5]tetrazin；3,6-bis(4-bromophenyl)-1,4-dihydro-1,2,4,5-tetrazine
• CAS: 68614-69-7
• 化学式: C₁₄H₁₀Br₂N₄
• 分子量: 394.068
• InChiKey: YLHLRHDTSTZIOP-UHFFFAOYSA-N

物化性质

• 熔点：
  310 °C(Solv: butyl acetate (123-86-4))
• 沸点：
  441.8±55.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-Di-(4-bromphenyl)-1,2-dihydro-1,2,4,5-tetrazin 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Stolle; Weindel, Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 74, p. 11

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-4-bromo-N-((Z)-(4-bromophenyl)chloromethylene)benzohydrazonoyl chloride 在 乙醚 、 一水合肼 作用下， 生成 3,6-Di-(4-bromphenyl)-1,2-dihydro-1,2,4,5-tetrazin
  参考文献：
  名称：

  Stolle; Weindel, Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 74, p. 11

  摘要：

  DOI：

文献信息

• Triphenylamine/tetrazine based π-conjugated systems as molecular donors for organic solar cells
  作者：Cassandre Quinton、Valérie Alain-Rizzo、Cécile Dumas-Verdes、Gilles Clavier、Laurence Vignau、Pierre Audebert

  DOI：10.1039/c5nj02097b

  日期：——

  Conjugated systems built by connecting one electron-donor triphenylamine to an electron-withdrawing tetrazine have been prepared using various linkers.

  使用不同的连接剂，将一个电子给体三苯胺连接到一个电子受体四唑，构建了共轭系统。
• Novel s-tetrazine-based dyes with enhanced two-photon absorption cross-section
  作者：Cassandre Quinton、San-Hui Chi、Cécile Dumas-Verdes、Pierre Audebert、Gilles Clavier、Joseph W. Perry、Valérie Alain-Rizzo

  DOI：10.1039/c5tc00531k

  日期：——

  properties, including one-photon absorption and two-photon absorption (2PA), were investigated with special attention to structure–property relationships. Large 2PA cross-sections (>800 GM) of these tetrazine dyes were evaluated by open aperture z-scan and non-degenerate 2PA techniques. The strong 2PA of these molecules is attributed to the extended π system and to the enhanced intramolecular charge transfer

  本文报道了一系列新型的基于四嗪的D–π–A–π–D和D–π–A型染料的合成以及线性和非线性吸收特性。在这些衍生物中，中央四嗪核通过一个或两个末端三苯胺部分连接各种π共轭间隔基。这些化合物可通过Stille或Suzuki-Miyaura交叉偶联有效地合成，这是关键步骤。研究了它们的光物理性质，包括一光子吸收和二光子吸收（2PA），并特别注意其结构与性质之间的关系。这些四嗪染料的大2PA横截面（> 800 GM）通过开孔z扫描和非简并2PA技术进行评估。这些分子的强2PA归因于扩展的π系统和三苯胺供体与中心四嗪受体之间分子内电荷转移的增强。
• Santus, Maria, Acta Poloniae Pharmaceutica, 1993, vol. 50, # 2.3, p. 183 - 188
  作者：Santus, Maria

  DOI：——

  日期：——
• Stolle, Journal fur praktische Chemie (Leipzig 1954), 1907, vol. <2> 75, p. 416
  作者：Stolle

  DOI：——

  日期：——
• Diazocinones:  Synthesis and Conformational Analysis
  作者：Lori I. Robins、Richard D. Carpenter、James C. Fettinger、Makhluf J. Haddadin、Dino S. Tinti、Mark J. Kurth

  DOI：10.1021/jo052577a

  日期：2006.3.1

  1,2,4,5-Tetrazines (prepared from aryl nitriles) condense with isoxazolylcyclobutanones (prepared from 3-benzenesulfonyl-3-vinylcyclobutanol) in methanolic KOH to give conformationally restricted 6-isoxazol-5-yl-6,7-dihydro-5H-[1,2]diazocin-4-ones. The solution H-1 NMR spectra of dihydrodiazocinone la with phenyl moieties at C3 and C8 reveal two conformations of the eight-membered heterocycle that are non-interconverting on the NMR time scale at ambient temperature. The kinetics of the conversion process, followed by H-1 NMR between 21 and 70 degrees C in DMSO Solution. yield an activation energy of similar to 21 kcal/mol relative to the kinetic conformer and show an equilibrated ratio of similar to 5:1 of the thermodynamic to the kinetic conformers. The electronic structure calculations on a model dihydrodiazocinone predict geometries for the two conformations. One of these geometries agrees with the X-ray crystallographic analysis of the thermodynamic conformation of 1a.