6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-1,2,4,5-tetrazin-3-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-1,2,4,5-tetrazin-3-amine
• 英文别名: 6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-1,2,4,5-tetraazin-3-amine；6-(3,5-dimethylpyrazol-1-yl)-N-methyl-1,2,4,5-tetrazin-3-amine
• 化学式: C₈H₁₁N₇
• 分子量: 205.222
• InChiKey: IOIHBANVHKAMNS-UHFFFAOYSA-N

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：
  81.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-1,2,4,5-tetrazin-3-amine 在 硝酸 作用下， 以66%的产率得到6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-N-nitro-1,2,4,5-tetrazin-3-amine
  参考文献：
  名称：

  Synthesis and Properties of Alkylnitramino-1,2,4,5-Tetrazines

  摘要：

  The peculiarities of the nitration reaction under acidic conditions were studied for a series of alkylamino-1,2,4,5-tetrazines. It was found that the extent of N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamine nitration was determined by the concentration of nitric acid and the selection of alkyl substituents at the exocyclic nitrogen atom. A new method was developed for the preparation of unsymmetrically substituted N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamines from N-nitro derivatives of N-alkyl-1,2,4,5-tetrazin-3-amines.

  DOI：

  10.1007/s10593-014-1448-9
• 作为产物：
  描述：

  3,6-二(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪 、 甲胺 以 乙腈 为溶剂， 生成 6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-1,2,4,5-tetrazin-3-amine
  参考文献：
  名称：

  Synthesis and Properties of Alkylnitramino-1,2,4,5-Tetrazines

  摘要：

  The peculiarities of the nitration reaction under acidic conditions were studied for a series of alkylamino-1,2,4,5-tetrazines. It was found that the extent of N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamine nitration was determined by the concentration of nitric acid and the selection of alkyl substituents at the exocyclic nitrogen atom. A new method was developed for the preparation of unsymmetrically substituted N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamines from N-nitro derivatives of N-alkyl-1,2,4,5-tetrazin-3-amines.

  DOI：

  10.1007/s10593-014-1448-9

文献信息

• Synthesis of monosubstituted 1,2,4,5-tetrazines – 3-amino-1,2,4,5-tetrazines
  作者：Gennady F. Rudakov、Yurii A. Moiseenko、Natal’ya А. Spesivtseva

  DOI：10.1007/s10593-017-2127-4

  日期：2017.6

  The substitution of pyrazolyl moiety in 3-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine with N-nucleophiles provided a series of highnitrogen tetrazine derivatives, including 2-nitro-1-(1,2,4,5-tetrazin-3-yl)guanidine, N-(1H-tetrazol-5-yl)-1,2,4,5-tetrazin-3-amine, N-(1,2,4,5-tetrazin-3-yl)-1,2,4,5-tetrazin-3-amine, N,N'-di(1,2,4,5-tetrazin-3-yl)-1,2,4,5-tetrazine-3,6-diamine, N-(1,2,4,5-tetrazin-3-yl)-[1

  用N-亲核试剂取代3-（3,5-二甲基-1 H-吡唑-1-基）-1,2,4,5-四嗪中的吡唑基部分，提供了一系列高氮四嗪衍生物，包括2-硝基-1-（1,2,4,5-四嗪-3-基）胍，N-（1 H-四唑-5-基）-1,2,4,5-四嗪-3-胺，N-（ 1,2,4,5-四嗪-3-基）-1,2,4,5-四嗪-3-胺，N，N'-二（1,2,4,5-四嗪-3-基） -1,2,4,5-四嗪-3,6-二胺，N-（1,2,4,5-四嗪-3-基）-[1,2,4]三唑[4,3- b ] [1,2,4,5]四嗪-6-胺和三四嗪胺。通过差示扫描量热法评估了这些新化合物的热稳定性，并计算了它们的能量特性。
• 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。
• Latosh; Rusinov; Ganebnykh, Russian Journal of Organic Chemistry, 1999, vol. 35, # 9, p. 1363 - 1371
  作者：Latosh、Rusinov、Ganebnykh、Chupakhin

  DOI：——

  日期：——
• Synthesis and Properties of Alkylnitramino-1,2,4,5-Tetrazines
  作者：G. F. Rudakov、T. V. Ustinova、I. B. Kozlov、V. F. Zhilin

  DOI：10.1007/s10593-014-1448-9

  日期：2014.4

  The peculiarities of the nitration reaction under acidic conditions were studied for a series of alkylamino-1,2,4,5-tetrazines. It was found that the extent of N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamine nitration was determined by the concentration of nitric acid and the selection of alkyl substituents at the exocyclic nitrogen atom. A new method was developed for the preparation of unsymmetrically substituted N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamines from N-nitro derivatives of N-alkyl-1,2,4,5-tetrazin-3-amines.