3,6-di(pyrrolidin-1-yl)-1,2,4,5-tetrazine | 117040-53-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,6-di(pyrrolidin-1-yl)-1,2,4,5-tetrazine
• 英文别名: 3,6-bis(pyrrolidino)-1,2,4,5-tetrazine；3,6-bis(pyrrolidin-1-yl)-s-tetrazine；3,6-dipyrrolidin-1-yl-1,2,4,5-tetrazine
• CAS: 117040-53-6
• 化学式: C₁₀H₁₆N₆
• 分子量: 220.277
• InChiKey: DVLFKROZLWVVCL-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C(Solv: water (7732-18-5); acetonitrile (75-05-8))
• 沸点：
  402.4±28.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di(pyrrolidin-1-yl)-1,2,4,5-tetrazine 以 一氟三氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Fischer, Hans; Mueller, Thomas; Umminger, Irmgard, Journal of the Chemical Society. Perkin transactions II, 1988, p. 413 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  四氢吡咯 、 3,6-双（甲硫基）-1,2,4,5-四嗪 反应 48.0h， 以63%的产率得到3,6-di(pyrrolidin-1-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Fischer, Hans; Mueller, Thomas; Umminger, Irmgard, Journal of the Chemical Society. Perkin transactions II, 1988, p. 413 - 422

  摘要：

  DOI：

文献信息

• Synthesis and Physical Chemistry of<i>s</i>-Tetrazines: Which Ones are Fluorescent and Why?
  作者：Yong-Hua Gong、Fabien Miomandre、Rachel Méallet-Renault、Sophie Badré、Laurent Galmiche、Jie Tang、Pierre Audebert、Gilles Clavier

  DOI：10.1002/ejoc.200900964

  日期：2009.12

  New fluorescent tetrazines have been prepared and their electrochemistry and fluorescence efficiency evaluated. The occurrence of fluorescence as well as the wavelength were found to be strongly dependent on the substituents, which have to be electronegative heteroatoms. This has been rationalized through a computational study that showed that the crucial factor is the nature of the HOMO, which determines

  已经制备了新的荧光四嗪并评估了它们的电化学和荧光效率。发现荧光的出现以及波长强烈依赖于取代基，取代基必须是带负电的杂原子。这已通过计算研究得到合理化，该研究表明关键因素是 HOMO 的性质，它决定了荧光的存在与否。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Nucleophilic substitution with amines: dihydro-1,2,4,5-tetrazines are more useful precursors than 1,2,4,5-tetrazines
  作者：Arnaud Cutivet、Emmanuel Leroy、Eric Pasquinet、Didier Poullain

  DOI：10.1016/j.tetlet.2008.02.145

  日期：2008.4

  avoids the up-to-now required oxidation step but also lower reaction times and/or temperatures compared to usual protocols. The efficiency of the reaction was highlighted by a practical synthesis of 3,6-bis(methylamino)-1,2,4,5-tetrazine using aqueous methylamine. Other primary and secondary amines were also found to give disubstitution products when reacted with 3,6-bis(methylsulfanyl)-1,2,4,5-dihydrotetrazine

  描述了直接从3,6-二取代-1,2-二氢-1,2,4,5-四嗪前体直接合成（二）烷基氨基取代的1,2,4,5-四嗪的一步法。一项比较研究表明，与常规方案相比，所描述的方法不仅避免了目前所需的氧化步骤，而且还缩短了反应时间和/或温度。通过使用甲胺水溶液实际合成3,6-双（甲基氨基）-1,2,4,5-四嗪突出了反应的效率。当与3,6-双（甲基硫烷基）-1,2,4,5-二氢四嗪反应时，还发现其他伯胺和仲胺会产生分解性产物。
• Synthesis of 1,2,4,5-tetrazines, symmetrically and unsymmetrically 3,6-disubstituted by N-nucleophiles
  作者：G. L. Rusinov、N. I. Latosh、I. I. Ganebnykh、R. I. Ishmetova、N. K. Ignatenko、O. N. Chupakhin

  DOI：10.1134/s1070428006050198

  日期：2006.5

  6-R-3-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazines with aliphatic, cycloaliphatic, and aromatic amines, and also with NH-heterocycles undergo a nucleophilic substitution of the dimethylpyrazole moiety yielding symmetrically and unsymmetrically substituted 1,2,4,5-tetrazines. In the 3,6-diimidazolyl- and 3,6-dibenzotriazolyl derivatives reactions of nucleophilic substitution of the heterocyclic moiety also occur. In some cases an ipsosubstitution of amino, hydrazino, and azido groups is observed.