3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine | 270588-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine
• 英文别名: 3-(3,5-Dimethyl-1-pyrazolyl)-6-methoxy-1,2,4,5-tetrazine；3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-s-tetrazine；3-(3,5-dimethylpyrazol-1-yl)-6-methoxy-s-tetrazine；3-(3,5-dimethylpyrazol-1-yl)-6-methoxytetrazine；3-(3,5-Dimethyl-1h-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine；3-(3,5-dimethylpyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine
• CAS: 270588-75-5
• 化学式: C₈H₁₀N₆O
• 分子量: 206.207
• InChiKey: VMHVPONGOUNAJA-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  401.8±48.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine 在 一水合肼 作用下， 以 乙腈 为溶剂， 以100%的产率得到3-hydrazino-6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Selective Nucleophilic Substitutions on Tetrazines

  摘要：

  DOI：

  10.3987/com-03-9875
• 作为产物：
  描述：

  甲醇 、 3,6-二(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪 在 sodium sulfate 作用下， 反应 2.0h， 以67%的产率得到3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine
  参考文献：
  名称：

  s-四嗪的合成和物理化学：哪些是荧光的，为什么？

  摘要：

  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)

  DOI：

  10.1002/ejoc.200900964

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)
• Synthesis of [1,2,4]triazolo[4,3-b]-s-tetrazines with incorporated furazan ring
  作者：A. B. Sheremetev、N. V. Palysaeva、K. Yu. Suponitskii、M. I. Struchkova

  DOI：10.1007/s11172-012-0017-6

  日期：2012.1

  Furazancarboxylic hydrazides can serve as nucleophiles to substitute for one dimethylpyrazole fragment in bis(3,5-dimethylpyrazol-1-yl)-s-tetrazine, giving the corresponding N′-[6-(3,5-dimethylpyrazol-1-yl)-s-tetrazin-3-yl]-4-R-furazan-3-carbohydrazides in good yields. Dehydration of the indicated carbohydrazides in polyphosphoric acid for the first time gave rise to [1,2,4]triazolo[4,3-b]-s-tetrazines containing the furazan ring as a substituent at the triazole ring.

  呋喃甲酰肼可以作为亲核物，替代双(3,5-二甲基吡唑-1-基)-s-四嗪中的一个二甲基吡唑片段，从而得到相应的 N′-[6-(3,5-二甲基吡唑-1-基)-s-四嗪-3-基]-4-R-呋喃-3-肼，产量很高。将上述羧肼在多磷酸中脱水后，首次生成了[1,2,4]三唑并[4,3-b]-s-四嗪，其中含有作为三唑环上取代基的呋喃环。
• Correlation of the Chemical Reactivity of Some Tetrazine Derivatives with Their Reactivity toward Ortho-positronium Atoms and Their LUMO Energies
  作者：Béla Lévay、András Kotschy、Zoltán Novák

  DOI：10.1021/jp0373649

  日期：2004.3.1

  Chemical reaction rate constants of the nucleophilic ortho-positronium (o-Ps) atom with a series of tetrazine derivatives were determined in dimethylformamide (DMF) solutions by positron annihilation lifetime spectroscopy. The observed rate constants are in the range that corresponds to that of the diffusion-controlled reactions. It was shown that this pronounced reactivity of tetrazines toward o-Ps

  通过正电子湮没寿命光谱法在二甲基甲酰胺 (DMF) 溶液中测定了亲核正电子 (o-Ps) 原子与一系列四嗪衍生物的化学反应速率常数。观察到的速率常数在对应于扩散控制反应的范围内。结果表明，四嗪对 o-Ps 的这种显着反应性源于缺电子四嗪核心。正如预期的那样，在四嗪环上引入给电子取代基会降低分子对 o-Ps 的反应性。测量的 o-Ps 反应速率常数与计算的四嗪的 LUMO 能量具有良好的线性相关性。四嗪对 o-Ps 的反应性也与其对经典亲核试剂的反应性密切相关。
• Latosh; Rusinov; Ganebnykh, Russian Journal of Organic Chemistry, 1999, vol. 35, # 9, p. 1363 - 1371
  作者：Latosh、Rusinov、Ganebnykh、Chupakhin

  DOI：——

  日期：——
• Replacement of dimethylpyrazolyl group in 1,2,4,5-tetrazines by aliphatic alcohols and water
  作者：R. I. Ishmetova、N. I. Latosh、I. N. Ganebnykh、N. K. Ignatenko、S. G. Tolshchina、G. L. Rusinov

  DOI：10.1134/s1070428009070197

  日期：2009.7

  Reactions of 3,6-bis(4-R-3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazines and 3-amino-6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazines with aliphatic alcohols and water in the presence of a base involved replacement of the dimethylpyrazolyl group and resulted in the formation of mono- and dialkoxy-1,2,4,5-tetrazines and 6-substituted 3-hydroxy-1,2,4,5-tetrazines. Dissociation constants of the latter were determined by potentiometric titration.