3,6-二甲基-1,2,4,5-四嗪烷 | 1743-05-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3,6-二甲基-1,2,4,5-四嗪烷
• 英文名称: 3,6-dimethylhexahydro-1,2,4,5-tetrazine
• 英文别名: 3,6-dimethyl-hexahydro-s-tetrazine；3,6-dimethyl-[1,2,4,5]tetrazinane；3,6-dimethyl-hexahydro-[1,2,4,5]tetrazine；3,6-Dimethyl-hexahydro-[1,2,4,5]tetrazin；3,6-Dimethyl-hexahydro-1,2,4,5-tetrazin；1,4-Dimethylhexahydro-s-tetrazin；3,6-Dimethyl-1,2,4,5-tetrazinane
• CAS: 1743-05-1
• 化学式: C₄H₁₂N₄
• 分子量: 116.166
• InChiKey: NKTSKXSUDLXBJV-UHFFFAOYSA-N

物化性质

• 沸点：
  155.9±20.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-二甲基-1,2,4,5-四嗪烷 在 5%-palladium/activated carbon 、 氧气 、 sodium hydroxide 作用下， 以17.39 g的产率得到3,6-二甲基-1,6-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  3,6-二甲基-1,2,4,5-四嗪-1,4-二二羧酸酰胺衍生物的合成，结构分析和抗肿瘤评估

  摘要：

  合成了3,6-二甲基-1,2,4,5-四嗪-1,4-二羧酸酰胺衍生物，并通过单晶X射线衍射确认了其结构。该反应产生的是1,4-二羧酸酰胺衍生物，而不是1,2-二羧酸酰胺衍生物。他们对SGC-7901，HO-8910，MCF-7和A-549细胞的体外抗肿瘤活性进行了评估。结果表明，在低微摩尔范围内，几种化合物具有细胞毒性。一种化合物（IC 50 = 0.57μ中号）在体内进一步评估对在BALB / CA裸鼠的A-549异种移植物; 通过腹膜内（ip）给予40 mg kg -1体重，可抑制76.4％的肿瘤重量。此外，还评估了其急性毒性，并通过了ip LD 50评估。小鼠中的值是325mg kg -1。

  DOI：

  10.1002/cmdc.201200109
• 作为产物：
  描述：

  乙醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 3,6-二甲基-1,2,4,5-四嗪烷
  参考文献：
  名称：

  3,6-二烷基-1,6-二氢-s-四嗪的简便制备

  摘要：

  摘要 1,6-二氢-s-四嗪类化合物 1，在杂环的 3-位和 6-位具有多种取代基，已被合成，由于它们的同芳香性和潜在的反应性，已经引起了越来越多的关注。更多的兴趣 (Sauer, J. 1,2,4,5-Tetraazines. In Comprehensive Heterocyclic Chemistry II; Boultou, AJ, Ed.; Elsevier: Oxford, UK, 1996; Vol. 6, 901; Neunhoeffer, H In Comprehensive Heterocyclic化学 I；Katritzky, A., Ed.；Pergamon Press Ltd.：德意志联邦共和国，1984；第 3 卷，545）。

  DOI：

  10.1081/scc-120022164

文献信息

• Synthesis and Structure Analysis of <i>N</i>¹,<i>N</i>⁴,3,6-Tetramethyl-<i>N</i>¹,<i>N</i>⁴-Diphenyl-1,4-Dihydro-1,2,4,5-Tetrazine-1,4-Dicarboxamide
  作者：Guo-Wu Rao、Qi Li、Zhen-Guo Zhao

  DOI：10.3184/174751912x13305517249355

  日期：2012.3

  N¹, N⁴,3,6-Tetramethyl- N¹, N⁴-diphenyl-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxamide was prepared from 3,6-dimethyl-1,6-dihydro-1,2,4,5-tetrazine, bis(trichloromethyl) carbonate and N-methylaniline. Its structure was confirmed by single-crystal X-ray diffraction. This reaction yields the title compound rather than N¹, N²,3,6-tetramethyl- N¹, N²-diphenyl-1,2-dihydro-1,2,4,5-tetrazine-1,2- dicarboxamide. The central tetrazine ring of the title compound exhibits a boat conformation and is therefore not homoaromatic.

  N1,N4,3,6-四甲基-N1,N4-二苯基-1,4-二氢-1,2,4,5-四嗪-1,4-二甲酰胺由 3,6-二甲基-1,6-二氢-1,2,4,5-四嗪、碳酸二（三氯甲基）酯和 N-甲基苯胺制备而成。单晶 X 射线衍射证实了其结构。该反应生成的是标题化合物，而不是 N1，N2，3，6-四甲基-N1，N2-二苯基-1，2-二氢-1，2，4，5-四嗪-1，2-二甲酰胺。标题化合物的中心四嗪环呈现舟形构象，因此不是均芳香族。
• Synthesis and Structure Analysis of<i>N</i>¹,<i>N</i>⁴-di-<i>tert</i>-Butyl-3,6-Dimethyl-1,4-Dihydro-1,2,4,5-Tetrazine-1,4-Dicarboxamide
  作者：Guo-Wu Rao、Jia-Bin Ni、Qi Li

  DOI：10.3184/174751912x13305927311260

  日期：2012.3

  N¹, N⁴-Di- tert-butyl-3,6-dimethyl-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxamide was prepared from 3,6-dimethyl-1,6-dihydro-1,2,4,5-tetrazine, and its structure was confirmed by single-crystal X-ray diffraction. This reaction yields the 1,4-dicarboxamide derivative rather than the 1,2-dicarboxamide derivative. The central six-member ring of the title compound has a boat conformation and therefore, is not homoaromatic.

  以 3,6-二甲基-1,6-二氢-1,2,4,5-四嗪为原料，制备了 N1, N4-二叔丁基-3,6-二甲基-1,4-二氢-1,2,4,5-四嗪-1,4-二甲酰胺，并通过单晶 X 射线衍射证实了其结构。该反应生成的是 1,4-二甲酰胺衍生物，而不是 1,2-二甲酰胺衍生物。标题化合物的中心六元环具有舟形构象，因此不是同芳香族。
• Convenient Preparation of 3,6-Dialkyl-1,6-dihydro-<i>s</i>-tetrazines
  作者：Yaquan Sun、Weixiao Hu、Qing Yuan

  DOI：10.1081/scc-120022164

  日期：2003.1.8

  as 1, with a large variety of substituents in the 3- and 6-position of the heterocycle, have been synthesized, and due to their homoaromaticities and their potential reactivities, have aroused more and more interests (Sauer, J. 1,2,4,5-Tetrazines. In Comprehensive Heterocyclic Chemistry II; Boultou, A.J., Ed.; Elsevier: Oxford, UK, 1996; Vol. 6, 901; Neunhoeffer, H In Comprehensive Heterocyclic Chemistry

  摘要 1,6-二氢-s-四嗪类化合物 1，在杂环的 3-位和 6-位具有多种取代基，已被合成，由于它们的同芳香性和潜在的反应性，已经引起了越来越多的关注。更多的兴趣 (Sauer, J. 1,2,4,5-Tetraazines. In Comprehensive Heterocyclic Chemistry II; Boultou, AJ, Ed.; Elsevier: Oxford, UK, 1996; Vol. 6, 901; Neunhoeffer, H In Comprehensive Heterocyclic化学 I；Katritzky, A., Ed.；Pergamon Press Ltd.：德意志联邦共和国，1984；第 3 卷，545）。
• Die Bildung von Hexahydro-1,2,4,5-tetrazinderivaten bei der Reaktion von Aldehyden mit Hydrazin
  作者：W. Skorianetz、E. Sz. Kováts

  DOI：10.1002/hlca.19700530206

  日期：——

  The cristalline reaction products of acetaldehyde and some of its higher straight chain homologues with one equivalent of hydrazine are shown to be 3, 6-dialkyl-hexahydro-1, 2, 4, 5-tetrazines (1) which can be oxidized to the corresponding 3, 6-dialkyl-1, 2, 4, 5-tetrazines.

  乙醛及其一些高级直链同系物与一当量肼的结晶反应产物显示为3，6-二烷基-六氢-1，2，4，5，5-四嗪（1），可以被氧化为相应的3，6-二烷基-1，2，4，4，5-四嗪。
• Synthesis and antitumor activity of s -tetrazine derivatives
  作者：Wei-Xiao Hu、Guo-Wu Rao、Ya-Quan Sun

  DOI：10.1016/j.bmcl.2003.12.056

  日期：2004.3

  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.