4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole | 62054-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole
• 英文别名: 4-Hexamethylenimino-7-nitrobenzofurazan；4-azepan-1-yl-7-nitro-benzo[1,2,5]oxadiazole；7-(Azepan-1-yl)-4-nitro-2,1,3-benzoxadiazole
• CAS: 62054-63-1
• 化学式: C₁₂H₁₄N₄O₃
• 分子量: 262.268
• InChiKey: QXXDTEHNGZLGFT-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  452.8±55.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole 在 sodium sulfide 作用下， 以 aq. phosphate buffer 为溶剂， 生成 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol
  参考文献：
  名称：

  通过带正电荷的 NBD 胺的硫解作用形成高效 H2S 清除剂

  摘要：

  H 2 S是一种众所周知的有毒气体，也是参与许多生物过程的气态信号分子。能够调节体内H 2 S 水平的先进化学工具有助于了解 H 2 S 生物学及其潜在的治疗效果。为此，我们开发了一系列7-硝基-1,2,3-苯并恶二唑(NBD)胺作为潜在的H 2 S清除剂。硫解反应的动力学研究表明，将带正电荷的基团掺入NBD胺上大大提高了H 2 S特异性硫解反应的速率。我们证明这些反应有效进行， NBD-S8在 37 °C 下的二阶速率常数 ( k 2 ) >116 M -1 s -1。此外，我们证明NBD-S8可以有效清除活细胞中酶促产生的内源性 H 2 S。为了进一步发挥生物学意义，我们证明NBD-S8介导小鼠体内H 2 S的清除。

  DOI：

  10.1039/d0sc01518k
• 作为产物：
  描述：

  环己亚胺 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 以 乙酸乙酯 为溶剂， 生成 4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole
  参考文献：
  名称：

  Photophysical and Dynamic NMR Studies on 4-Amino-7-nitrobenz-2-oxa-1, 3-diazole Derivatives:  Elucidation of the Nonradiative Deactivation Pathway

  摘要：

  A series of 4-aminonitrobenzoxadiazole (NBD) derivatives in which the amino nitrogen is part of a four- to seven-membered heterocyclic ring and a second series of 4-dialkylamino NBD derivatives with different alkyl chain lengths have been prepared and fully characterized and their photophysical properties investigated in an attempt to find out the nonradiative deactivation pathway of the fluorescent state in these systems. It is observed that the fluorescence properties of the NBD derivatives are highly sensitive to the structure of the amino moiety and the polarity of the surrounding media. It is shown that the nonradiative rate constants for the derivatives with large alkyl groups and large ring systems are considerably higher than those for systems with smaller alkyl groups and smaller ring systems. Dynamic NMR experiments have been carried out to probe the internal motion in the systems. The internal rotation around the bond connecting the amino nitrogen and the NBD ring is found to be rather slow in the ground state. The rate for the internal rotation is found to be the highest for the six-membered ring, and this has been interpreted in terms of the partial double bond character of the C-N bond. The results of the experiments seem to indicate that inversion of the amino nitrogen plays the most important role in determining the fluorescence efficiency of the systems.

  DOI：

  10.1021/jp982154v

文献信息

• Latham,D.W.S. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 2216 - 2221
  作者：Latham,D.W.S. et al.

  DOI：——

  日期：——
• Photophysical and Dynamic NMR Studies on 4-Amino-7-nitrobenz-2-oxa-1, 3-diazole Derivatives:  Elucidation of the Nonradiative Deactivation Pathway
  作者：Satyen Saha、Anunay Samanta

  DOI：10.1021/jp982154v

  日期：1998.10.1

  A series of 4-aminonitrobenzoxadiazole (NBD) derivatives in which the amino nitrogen is part of a four- to seven-membered heterocyclic ring and a second series of 4-dialkylamino NBD derivatives with different alkyl chain lengths have been prepared and fully characterized and their photophysical properties investigated in an attempt to find out the nonradiative deactivation pathway of the fluorescent state in these systems. It is observed that the fluorescence properties of the NBD derivatives are highly sensitive to the structure of the amino moiety and the polarity of the surrounding media. It is shown that the nonradiative rate constants for the derivatives with large alkyl groups and large ring systems are considerably higher than those for systems with smaller alkyl groups and smaller ring systems. Dynamic NMR experiments have been carried out to probe the internal motion in the systems. The internal rotation around the bond connecting the amino nitrogen and the NBD ring is found to be rather slow in the ground state. The rate for the internal rotation is found to be the highest for the six-membered ring, and this has been interpreted in terms of the partial double bond character of the C-N bond. The results of the experiments seem to indicate that inversion of the amino nitrogen plays the most important role in determining the fluorescence efficiency of the systems.
• Highly efficient H₂S scavengers <i>via</i> thiolysis of positively-charged NBD amines
  作者：Ismail Ismail、Zhuoyue Chen、Lu Sun、Xiuru Ji、Haishun Ye、Xueying Kang、Haojie Huang、Haibin Song、Sarah G. Bolton、Zhen Xi、Michael D. Pluth、Long Yi

  DOI：10.1039/d0sc01518k

  日期：——

  in vivo are useful for understanding H2S biology as well as its potential therapeutic effects. To this end, we have developed a series of 7-nitro-1,2,3-benzoxadiazole (NBD) amines as potential H2S scavengers. The kinetic studies of thiolysis reactions revealed that incorporation of positively-charged groups onto the NBD amines greatly increased the rate of the H2S-specific thiolysis reaction. We demonstrate

  H 2 S是一种众所周知的有毒气体，也是参与许多生物过程的气态信号分子。能够调节体内H 2 S 水平的先进化学工具有助于了解 H 2 S 生物学及其潜在的治疗效果。为此，我们开发了一系列7-硝基-1,2,3-苯并恶二唑(NBD)胺作为潜在的H 2 S清除剂。硫解反应的动力学研究表明，将带正电荷的基团掺入NBD胺上大大提高了H 2 S特异性硫解反应的速率。我们证明这些反应有效进行， NBD-S8在 37 °C 下的二阶速率常数 ( k 2 ) >116 M -1 s -1。此外，我们证明NBD-S8可以有效清除活细胞中酶促产生的内源性 H 2 S。为了进一步发挥生物学意义，我们证明NBD-S8介导小鼠体内H 2 S的清除。
• 4-Amino derivatives of 7-nitro-2,1,3-benzoxadiazole: the effect of the amino moiety on the structure of fluorophores
  作者：Satyen Saha

  DOI：10.1107/s0108270102000173

  日期：2002.3.15

  The crystal structures of three 4-amino derivatives of 7-nitro-2,1,3-benzoxadiazole with increasing substituent ring size, viz. 7-nitro-4-(pyrrolidin-1-yl)-2,1,3-benzoxadiazole, C10H10N4O3, 7-nitro-4-(piperidin-1-yl)-2,1,3-benzoxadiazole, C11H12N4O3, and 4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole, C12H14N4O3, have been determined in order to understand their photophysical behaviour. All three were found to crystallize in centrosymmetric space groups. There is considerable electron delocalization compared with the parent compound, although the five-membered oxadiazole ring apparently does not participate in this. The length of the C-N bond between the amino N atom and the 7-nitrobenzoxadiazole system is found to be shorter than in similar compounds, as is the C-N-nitro bond. In each structure, the nitro group lies in the plane of the benzoxadiazole unit.