3,6-bis(4-bromo-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine | 270588-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 3,6-bis(4-bromo-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine
• 英文别名: 3,6-bis(4-bromo-3,5-dimethylpyrazol-1-yl)-s-tetrazine；3,6-Bis(3,5-dimethyl-4-bromopyrazol-1-yl)-1,2,4,5-tetrazine
• CAS: 270588-85-7
• 化学式: C₁₂H₁₂Br₂N₈
• 分子量: 428.089
• InChiKey: PEEQUTCEQRCZAX-UHFFFAOYSA-N

物化性质

• 沸点：
  615.8±65.0 °C(Predicted)
• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-bis(4-bromo-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine 在 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到potassium-6-(2-bromo-3,5-dimethylpyrazol-1-yl)tetrazin-3-olate
  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：

  3,6-二(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 0.03h， 以91%的产率得到3,6-bis(4-bromo-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Synthesis of [1,2,4]triazolo[4,3-b]-s-tetrazines with incorporated furazan ring

  摘要：

  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。

  DOI：

  10.1007/s11172-012-0017-6

文献信息

• Synthesis and reactions of 7-phenylimidazo[1,2-b][1,2,4,5]tetrazines with nucleophiles
  作者：I. N. Ganebnykh、R. I. Ishmetova、S. G. Tolshchina、A. V. Korotina、D. S. Filatov、P. A. Slepukhin、G. L. Rusinov

  DOI：10.1007/s11172-018-2281-6

  日期：2018.9

  A series of novel 3-substituted 7-phenylimidazo[1,2-b][1,2,4,5]tetrazines was synthesized via the reaction of 3-R-amino-1,2,4,5-tetrazines with 2-aminoacetophenone. The structural features and possibilities of modification of 7-phenylimidazotetrazine system in the reactions with nucleophiles were studied.

  3-R-氨基-1,2,4,5-四嗪与2-R-氨基-1,2,4,5-四嗪反应合成了一系列新型3-取代7-苯基咪唑并[1,2-b][1,2,4,5]四嗪。 -氨基苯乙酮。研究了7-苯基咪唑四嗪体系在与亲核试剂反应中的结构特征和改性的可能性。
• HETARYL DISPLACEMENT IN 3,6-DISUBSTITUTED 1,2,4,5-TETRAZINES WITH ANHYDRO BASES OF N-METHYLQUINALDINIUMS
  作者：Gennady L. Rusinov、Rashida I. Ishmetova、Ilya N. Ganebnykh、Oleg N. Chupakhin

  DOI：10.1515/hc.2006.12.2.99

  日期：2006.1
• Latosh; Rusinov; Ganebnykh, Russian Journal of Organic Chemistry, 1999, vol. 35, # 9, p. 1363 - 1371
  作者：Latosh、Rusinov、Ganebnykh、Chupakhin

  DOI：——

  日期：——
• [4+2]-Cycloaddition of 3,6-bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines with alkenes
  作者：G. L. Rusinov、R. I. Ishmetova、N. I. Latosh、I. N. Ganebnych、O. N. Chupakhin、V. A. Potemkin

  DOI：10.1007/bf02494688

  日期：2000.2

  A number of 1,4-dihydropyridazines and pyridazines were prepared by the Diels-Alder reaction with an inverse electron demand from cyclic heterodiene systems, 3,6-bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines, and some enamines as well as from 4-vinylpyridine. butyl vinyl ether, phenylacetylene, and acrylamide. The reaction of 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine with styrene afforded 4,5-dihydropyridazine, which was readily oxidized by atmospheric oxygen to form the corresponding pyridazine. Electron-withdrawing substituents (Br or Cl) in the pyrazole rings accelerate [4+2]-cycloaddition. When heated, 1,4-dihydropyridazines, which were synthesized from tetrazines and enamines, eliminated amine to give pyridazines. The reactivities of tetrazines were evaluated by quantum-chemical methods.
• Reactions of 3,6-Bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines with Indole and 1,3,3-Trimethyl-2-methyleneindoline
  作者：Gennady L. Rusinov、Rashida I. Ishmetova、Nina K. Ignatenko、Ilya N. Ganebnykh、Svetlana G. Tolshchina、Pavel A. Slepukhin

  DOI：10.3987/com-11-12165

  日期：——

  It has been found that 3,6-bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines react with indole and 1,3,3-trimethyl-2-methyleneindoline to give pyridazines as [4+2]cycloaddition products. 1,3,3-Trimethyl-2-methyleneindoline has been shown to act as C-nucleophile in the substitution of pyrazolyl group as well as in the reactions of tetrazine ring expansion in [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine derivatives.