5,7-dinitrobenzo-1,2,3,4-tetrazine 1,3-dioxide

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5,7-dinitrobenzo-1,2,3,4-tetrazine 1,3-dioxide
• 英文别名: 5,7-Dinitrobenzotetrazine-1,3-dioxide；5,7-dinitro-1,3-dioxido-1,2,3,4-benzotetrazine-1,3-diium
• 化学式: C₆H₂N₆O₆
• 分子量: 254.118
• InChiKey: BCTCWTNTQNGYDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzo-1,2,3,4-tetrazine 1,3-dioxide 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以55%的产率得到5,7-dinitrobenzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  摘要：

  Benzo-1,2,3,4-tetrazine 1,3-dioxide (BTDO) and its derivatives were nitrated with HNO3/H2SO4 or HNO3/oleum and brominated with dibromoisocyanuric acid in CF3CO2H/H2SO4 (5 : 1) or H2SO4. The reactivity of positions in the benzene ring of this heterocyclic system as regards electrophilic substitution was found to change in the following order: 5 approximate to 7 > 8 > 6. Mono- and dinitro-BTDOs and mono- and polybromo-BTDOs were synthesized. Their structures were confirmed by H-1, C-13, and N-14 NMR spectra.

  DOI：

  10.1023/a:1021344300420

文献信息

• Benzo-1,2,3,4-tetrazine 1,3-Dioxides: Synthesis and NMR Study
  作者：Aleksandr M. Churakov、Oleg Yu. Smirnov、Sema L. Ioffe、Yuri A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1002/1099-0690(200207)2002:14<2342::aid-ejoc2342>3.0.co;2-h

  日期：2002.7
• ——
  作者：O. Yu. Smirnov、A. M. Churakov、Yu. A. Strelenko、S. L. Ioffe、V. A. Tartakovsky

  DOI：10.1023/a:1021344300420

  日期：——

  Benzo-1,2,3,4-tetrazine 1,3-dioxide (BTDO) and its derivatives were nitrated with HNO3/H2SO4 or HNO3/oleum and brominated with dibromoisocyanuric acid in CF3CO2H/H2SO4 (5 : 1) or H2SO4. The reactivity of positions in the benzene ring of this heterocyclic system as regards electrophilic substitution was found to change in the following order: 5 approximate to 7 > 8 > 6. Mono- and dinitro-BTDOs and mono- and polybromo-BTDOs were synthesized. Their structures were confirmed by H-1, C-13, and N-14 NMR spectra.