7-nitrobenzo-1,2,3,4-tetrazine 1,3-dioxide | 137887-33-3

• 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: 7-nitrobenzo-1,2,3,4-tetrazine 1,3-dioxide
• 英文别名: 7-Nitrobenzotetrazine-1,3-dioxide；6-nitro-2,4-dioxido-1,2,3,4-benzotetrazine-2,4-diium
• CAS: 137887-33-3
• 化学式: C₆H₃N₅O₄
• 分子量: 209.121
• InChiKey: YWRKENKCBYZNDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 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：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-nitrobenzo-1,2,3,4-tetrazine 1,3-dioxide 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以75%的产率得到7-azidobenzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1021396317258
• 作为产物：
  描述：

  2-氯-5-硝基苯胺 在 磷酸酐 、 ammonium persulfate 、 nitronium tetrafluoborate 、 硫酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 18.0h， 生成 7-nitrobenzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  合成苯并[e][1,2,3,4]四嗪1,3-二氧化物的新方法

  摘要：

  一种合成苯并[e][1,2,3,4]四嗪1,3-二氧化物的新方法包括用磷酸酐或磷处理含有anortho-(叔丁基-NNO-azoxy)基团的N-硝基苯胺五氯化物。该反应应该通过中间重氮氧化物阳离子进行。

  DOI：

  10.1007/bf02494779

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.
• 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.
• ——
  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.
• New approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides
  作者：A. E. Frumkin、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/bf02494779

  日期：2000.3

  3-dioxides involves the treatment ofN-nitroanilines containing anortho-(tert-butyl-NNO-azoxy) group with phosphoric anhydride or phosphorus pentachloride. The reaction is supposed to proceed through an intermediate diazonium oxide cation.

  一种合成苯并[e][1,2,3,4]四嗪1,3-二氧化物的新方法包括用磷酸酐或磷处理含有anortho-(叔丁基-NNO-azoxy)基团的N-硝基苯胺五氯化物。该反应应该通过中间重氮氧化物阳离子进行。