nitrobenzoxadiazole-DMSO | 1433738-28-3

• 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: nitrobenzoxadiazole-DMSO
• CAS: 1433738-28-3
• 化学式: C₈H₈N₄O₄S
• 分子量: 256.242
• InChiKey: NAQVIGHDDKGOGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111.49
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 sodium azide 、 copper dichloride 作用下， 以 水 、 丙酮 为溶剂， 反应 24.25h， 生成 nitrobenzoxadiazole-DMSO 、 4-amino-7-nitro-2,1,3-benzoxadiazole
  参考文献：
  名称：

  An unexpected copper catalyzed ‘reduction’ of an arylazide to amine through the formation of a nitrene intermediate

  摘要：

  Azido nitrobenzoxadiazole (NBD) was observed to undergo a 'reduction' reaction in the absence of an obvious reducing agent, leading to amine formation. In the presence of an excess amount of DMSO, a sulfoxide conjugate was also formed. The ratio of these two products was both temperature- and solvent-dependent, with the addition of water significantly enhancing the ratio of the 'reduction' product. Two intermediates of the azido-NBD reaction in DMSO were trapped and characterized by low-temperature EPR spectroscopy. One was an organic free radical (S=1/2) and another was a triplet nitrene (S=1) species. A mechanism was proposed based on the characterized free radical and triplet intermediates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.091