3,6-Bis-(p-tolyl)-1,2-dihydro-1,2,4,5-tetrazin | 53460-56-3

• 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-Bis-(p-tolyl)-1,2-dihydro-1,2,4,5-tetrazin
• 英文别名: 3,6-Di-(4-methylphenyl)-1,2-dihydro-1,2,4,5-tetrazin；3,6-di-p-tolyl-1,2-dihydro-[1,2,4,5]tetrazine；3,6-Di-p-tolyl-1,2-dihydro-[1,2,4,5]tetrazin；3,6-bis(4-methylphenyl)-1,4-dihydro-1,2,4,5-tetrazine
• CAS: 53460-56-3
• 化学式: C₁₆H₁₆N₄
• 分子量: 264.33
• InChiKey: KKDMVDGPYAFDAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-Bis-(p-tolyl)-1,2-dihydro-1,2,4,5-tetrazin 在 溶剂黄146 、 sodium nitrite 作用下， 以38%的产率得到3,6-di-p-tolyl-[1,2,4,5]tetrazine
  参考文献：
  名称：

  Synthesis and antitumor activity of s -tetrazine derivatives

  摘要：

  Fifty-five compounds of s-tetrazine derivative including hexahydro-, 1,6-dihydro, 1,4-dihydro-, 1,2-dihydro- and aromatic s-tetrazine were prepared. Their antitumor activities were evaluated in vitro by MTT method for P-388 cell and SRB method for A-549 cell. The results show that there are 9 compounds which in 10(-6) muM have more than 50% inhibition rate to A-549 cancer cell growth, and 7 compounds in 10(-6) muM have more than 50% inhibition rate to P-388 cancer cell growth. The IC50 of compound 3q for P-388, Bel-7402, MCF-7 and A-549 are 0.6 muM, 0.6 muM, 0.5 muM and 0.7 muM, respectively. So s-tetrazine derivative is a kind of compound which possesses potential antitumor activities and is worth to research further. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.056
• 作为产物：
  描述：

  4-甲基苯甲脒盐酸盐 在 盐酸 、 氢氧化钾 、 硫酸肼 作用下， 生成 3,6-Bis-(p-tolyl)-1,2-dihydro-1,2,4,5-tetrazin
  参考文献：
  名称：

  Pinner, Justus Liebigs Annalen der Chemie, 1897, vol. 298, p. 30

  摘要：

  DOI：

文献信息

• First representatives of <i>C</i>-glycosyl 1,2,4,5-tetrazines: synthesis of 3-β-<scp>d</scp>-glucopyranosyl 1,2,4,5-tetrazines and their transformation into 3-β-<scp>d</scp>-glucopyranosyl pyridazines
  作者：Éva Bokor、Dóra T. Kecskés、Ferenc Gombás、Alexandra Fehér、Eszter Kardos、Akram Dabian、Zsófia Vonza、Eszter Szennyes、László Somsák

  DOI：10.1039/d2nj03920f

  日期：——

  applications e.g. in heterocyclic syntheses and recently in bioorthogonal chemistry. C-Glycopyranosyl tetrazines are unknown in the literature, therefore, we have started to study their synthesis. In this paper ring closing reactions leading to s-tetrazines have been investigated with suitable β-D-glucopyranosyl precursors and the feasible transformations have been identified. In addition, the obtained

  1,2,4,5-四嗪（s-四嗪）是一类早已为人所知的化合物，具有许多应用，例如杂环合成和最近的生物正交化学。C- Glycopyranosyl四嗪在文献中是未知的，因此，我们已经开始研究它们的合成。在本文中，已经用合适的 β- D-吡喃葡萄糖基前体研究了导致s-四嗪的闭环反应，并确定了可行的转化。此外，获得的C-吡喃葡萄糖基四嗪的基本保护基相容性及其在反电子需求 Diels-Alder 环加成对各种C-吡喃葡萄糖基哒嗪已被证实。
• Mueller; Herrdegen, Journal fur praktische Chemie (Leipzig 1954), 1921, vol. <2> 102, p. 132
  作者：Mueller、Herrdegen

  DOI：——

  日期：——
• Wuyts; Lacourt, Bulletin des Societes Chimiques Belges, 1936, vol. 45, p. 685,692
  作者：Wuyts、Lacourt

  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.