3-bromo-2-(tert-butyl-NNO-azoxy)aniline | 501665-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-bromo-2-(tert-butyl-NNO-azoxy)aniline
• CAS: 501665-35-6
• 化学式: C₁₀H₁₄BrN₃O
• 分子量: 272.145
• InChiKey: KPWJBQZRCAAJEV-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.45
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(tert-butyl-NNO-azoxy)aniline 在 溴 、 sodium acetate 、 五氧化二氮 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 7,8-dibromobenzo-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：

  2,6-二溴苯胺 在 氨 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 20.0~210.0 ℃ 、30.4 MPa 条件下， 反应 28.0h， 生成 3-bromo-2-(tert-butyl-NNO-azoxy)aniline
  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

文献信息

• The tert-butyl-NNO-azoxy group in the synthesis of 1,2,4-benzotriazin-3(4H)-one 1-oxides
  作者：D. L. Lipilin、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/s11172-007-0244-4

  日期：2007.8

  novel route to 1,2,4-benzotriazin-3(4H )-one 1-oxides. This method involves a new reaction, viz., an intramolecular interaction of the tert-butyl-NNO-azoxy group with a C-electrophile (leading to the formation of the N(2)—C(3) bond of the triazine ring) followed by elimination of the tert-butyl group. Complete assignment of the signals in the 1H and 13C NMR spectra of the compounds obtained was performed

  提出了在 20 °C 下用光气处理 2-(叔丁基-NNO-偶氮氧基)苯胺作为制备 1,2,4-苯并三嗪-3(4H )-one 1-氧化物的新途径。该方法涉及一个新反应，即叔丁基-NNO-偶氮氧基与 C-亲电试剂的分子内相互作用（导致三嗪环的 N(2)-C(3) 键的形成）然后消除叔丁基。对所得化合物的 1H 和 13C NMR 光谱中的信号进行了完全分配。