3,6-Bis(4-chloro-3,5-dimethyl-1-pyrazolyl)-1,2,4,5-tetrazine | 270588-84-6

• 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-chloro-3,5-dimethyl-1-pyrazolyl)-1,2,4,5-tetrazine
• 英文别名: 3,6-bis(4-chloro-3,5-dimethylpyrazol-1-yl)-s-tetrazine；3,6-bis(4-chloro-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine
• CAS: 270588-84-6
• 化学式: C₁₂H₁₂Cl₂N₈
• 分子量: 339.187
• InChiKey: IQULWURESQLLIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-chloro-3,5-dimethyl-1-pyrazolyl)-1,2,4,5-tetrazine 以 氯仿 、 乙腈 为溶剂， 反应 0.08h， 生成 1,4-bis(4-chloro-3,5-dimethylpyrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridazine
  参考文献：
  名称：

  [4+2]-Cycloaddition of 3,6-bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines with alkenes

  摘要：

  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.

  DOI：

  10.1007/bf02494688
• 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-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 0.67h， 以81%的产率得到3,6-Bis(4-chloro-3,5-dimethyl-1-pyrazolyl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  [4+2]-Cycloaddition of 3,6-bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines with alkenes

  摘要：

  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.

  DOI：

  10.1007/bf02494688

文献信息

• 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：——
• 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.
• [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.