5,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide | 473895-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 5,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide
• 英文别名: 5,7-Dibromo-1,3-dioxido-1,2,3,4-benzotetrazine-1,3-diium
• CAS: 473895-50-0
• 化学式: C₆H₂Br₂N₄O₂
• 分子量: 321.915
• InChiKey: HPQCMTGIUPOYQL-UHFFFAOYSA-N

物化性质

• 沸点：
  501.7±46.0 °C(Predicted)
• 密度：
  2.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 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：
  76.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide 在 硫酸 、 硝酸 作用下， 反应 0.5h， 以64%的产率得到5,7-dibromo-8-nitrobenzo-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
• 作为产物：
  描述：

  4,6-dibromo-2-(tert-butyl-NNO-azoxy)aniline 在 五氧化二氮 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以53%的产率得到5,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  Benzo-1,2,3,4-tetrazine 1,3-Dioxides: Synthesis and NMR Study

  摘要：

  DOI：

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

文献信息

• Annulated benzotetrazine 1,3-dioxides 2.* [1,2,5]Oxadiazolo[3,4-f ][1,2,3,4]benzotetrazine 1,3,7-trioxide
  作者：A. Yu. Tyurin、O. Yu. Smirnov、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/s11172-006-0259-2

  日期：2006.2

  Thermolysis of 8-azido-7-nitrobenzotetrazine 1,3-dioxide led to benzotetrazine 1,3-dioxide annulated with the furoxan ring at the C(7)—C(8) bond. Complete assignment of the signals in the 13C NMR spectrum of the compound obtained was performed. Attempted syntheses of benzotetrazine 1,3-dioxides annulated with a furoxan ring at the C(6)—C(7) bond or two furoxan rings at the C(5)—C(6) and C(7)—C(8) bonds were unsuccessful.

  8-叠氮-7-硝基苯并四氮杂环1,3-二氧化物的热裂解导致了在C(7)—C(8)键处与呋喃环相连的苯并四氮杂环1,3-二氧化物的生成。对所获得化合物的13C NMR光谱信号进行了完整的归属。对在C(6)—C(7)键处与呋喃环相连或在C(5)—C(6)和C(7)—C(8)键处与两个呋喃环相连的苯并四氮杂环1,3-二氧化物的合成尝试均未成功。
• ——
  作者：O. Yu. Smirnov、A. M. Churakov、A. Yu. Tyurin、Yu. A. Strelenko、S. L. Ioffe、V. A. Tartakovsky

  DOI：10.1023/a:1021396317258

  日期：——

  Nucleophilic substitution in nitro- and bromobenzo-1,2,3,4-tetrazine 1,3-dioxides (BTDOs) was studied. In most cases, the bromo and nitro groups are replaced by methylamino, dimethylamino, azido, and methoxy groups without opening of the tetrazine ring. It was illustrated with the reactions of dibromo-BTDOs with sodium methoxide that the reactivity of positions 5 to 8 in their benzene ring as regards nucleophilic substitution changes in the following order: 6 > 8 > 7 > 5. The structures of the BTDOs obtained were confirmed by H-1, C-13, and N-14 NMR data.
• Release of Nitrosating Species in the Course of Reduction of Benzo-1,2,3,4-tetrazine 1,3-Dioxides
  作者：Maxim O. Ratnikov、Dmitry L. Lipilin、Aleksandr M. Churakov、Yuri A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1021/ol026437o

  日期：2002.9.1

  The reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides (BTDOs) 1 with Na2S2O4 or SnCl2 is suggested to proceed via intermediate N-nitrosobenzotriazoles 3 to afford benzotriazoles 2. The N-15-labeling experiments exhibit that the N-3 atom of the tetrazine ring is incorporated into the nitroso group of 3 that is ultimately released into solution. It is possible that the biological activity of BTDOs is due to their ability to release nitrosating species, i.e., N-nitrosotriazol 3 or HNO2, in the course of reduction.
• 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.