benzo-1,2,3,4-tetrazine 1,3-dioxide | 128767-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: benzo-1,2,3,4-tetrazine 1,3-dioxide
• 英文别名: Benzotetrazine-1,3-dioxide；2,4-dioxido-1,2,3,4-benzotetrazine-2,4-diium
• CAS: 128767-05-5
• 化学式: C₆H₄N₄O₂
• 分子量: 164.123
• InChiKey: OEOUFKMXEJIZNW-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  407.6±28.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 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：

  benzo-1,2,3,4-tetrazine 1,3-dioxide 在 tin(ll) chloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以97%的产率得到T406石油添加剂
  参考文献：
  名称：

  Release of Nitrosating Species in the Course of Reduction of Benzo-1,2,3,4-tetrazine 1,3-Dioxides

  摘要：

  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.

  DOI：

  10.1021/ol026437o
• 作为产物：
  描述：

  1-amino-2-(tert-butylazoxy)benzene 在 吡啶 、 nitrosonium tetrafluoroborate 、 间氯过氧苯甲酸 作用下， 生成 benzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  1,2,3,4-tetrazine 1,3-dioxides ? A new class of heterocyclic compounds

  摘要：

  DOI：

  10.1007/bf00959610

文献信息

• Generation of oxodiazonium ions 2. Synthesis of benzotetrazine-1,3-dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines
  作者：M. S. Klenov、V. P. Zelenov、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/s11172-011-0310-9

  日期：2011.10

  A new method for the synthesis of benzotetrazine-1,3-dioxides was developed, which involves the reaction of 2-(tert-butyl-NNO-azoxy)-N-nitroanilines with the Ac2O/H2SO4 system. This method was also used for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-5-oxide from 3-nitramino-4-phenylfurazan. The suggested mechanism of these reactions involves the formation of the intermediate oxodiazonium ion, resulting from acetylation of the oxygen atom of the nitramine group, followed by protonation and ionic dissociation. Then the oxodiazonium ion enters the intramolecular reaction with the neighboring tert-butyl-NNO-azoxy or phenyl group to form the corresponding heterocyclic systems.

  开发了一种合成苯并四嗪-1,3-二氧化物的新方法，该方法涉及 2-（叔丁基-NNO-氮氧）-N-硝基苯胺与 Ac2O/H2SO4 系统的反应。这种方法还被用于从 3-硝基氨基-4-苯基呋咱合成 [1,2,5]噁二唑并[3,4-c]噌啉-5-氧化物。这些反应的机理是，硝胺基团的氧原子乙酰化后形成中间体氧二氮离子，然后质子化和离子解离。然后，氧二氮离子与邻近的叔丁基-NNO-氮氧基或苯基发生分子内反应，形成相应的杂环系统。
• Generation of oxodiazonium ions 4. Nitramine O-alkyl derivatives in the synthesis of benzotetrazine-1,3-dioxides
  作者：M. S. Klenov、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/s11172-011-0312-7

  日期：2011.10

  A new method for the synthesis of benzotetrazine-1,3-dioxides was developed from the 2-(tert-butyl-NNO-azoxy)-N-nitroaniline O-alkyl derivatives upon the action of strong acids (H2SO4, MeSO3H, CF3CO2H) or BF3·Et2O. A mechanism suggested for these reactions includes transformation of the N=N(O)OR group (R = Me, Pri) to the oxodiazonium ion (N=N=O)+, which intramolecularly reacts with the neighboring tert-butyl-NNO-azoxy group, furnishing the tetrazine-1,3-dioxide ring.

  在强酸（H2SO4、MeSO3H、CF3CO2H）或 BF3-Et2O 的作用下，从 2-（叔丁基-NNO-氮氧）-N-硝基苯胺 O-烷基衍生物中开发出一种合成苯并四嗪-1,3-二氧 化物的新方法。这些反应的机理包括：N=N(O)OR 基团（R=Me，Pri）转变成氧二氮离子（N=N=O）+，后者与邻近的叔丁基-NNO-氮氧基团发生分子内反应，生成四嗪-1,3-二氧化物环。
• 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。
• ——
  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.
• 1,2,3,4-tetrazine 1,3-dioxides ? A new class of heterocyclic compounds
  作者：A. M. Churakov、S. L. Ioffe、Yu. A. Strelenko、V. A. Tartakovskii

  DOI：10.1007/bf00959610

  日期：1990.3