4-nitro-7-phenylsulphonylbenzofurazan | 53619-71-9

• 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-nitro-7-phenylsulphonylbenzofurazan
• 英文别名: 4-(Benzenesulfonyl)-7-nitro-2,1,3-benzoxadiazole
• CAS: 53619-71-9
• 化学式: C₁₂H₇N₃O₅S
• 分子量: 305.271
• InChiKey: AISIRVKTYOBQGY-UHFFFAOYSA-N

物化性质

• 沸点：
  540.8±60.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-nitro-7-phenylsulphonylbenzofurazan 在 sodium 作用下， 反应 0.33h， 生成 4-methoxy-7-phenylsulphonylbenzofurazan
  参考文献：
  名称：

  Belton, James G.; McElhinney, R Stanley, Journal of the Chemical Society. Perkin transactions I, 1988, p. 145 - 150

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-nitro-7-phenylsulphonylbenzofurazan
  参考文献：
  名称：

  The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1,2,5]oxadiazole dyes

  摘要：

  The different oxidation states of sulphur atom play a significant role on functional materials. In this work, a aryl-thioether and its sulphone substituted benzo[c][1,2,5]oxadiazole dyes were synthesized and utilized to determine thiol-containing amino acids. The result of selectivity experiments showed they detected the cysteine and homocysteine under physiological condition with negligible interference from other amino acids. In comparison to the thioether dye, the sulphone-based dye exhibited much faster response time for Cys and Hcy. However, the sulphone restricted its thiol-reactivity and bioimaging performance in living cells. By reducing the oxidation state of sulphur atom, we amazedly found that the sulfoxide-based dye still maintained high selectivity ultrafast response time for Cys/Hcy under physiological condition. It was worth mentioning that it also had high reactivity and good bioimaging performance that sulfone compounds did not have. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2020.02.047

文献信息

• BELTON, JAMES G.;MCELHINNEY, R. STANLEY, J. CHEM. SOC. PERKIN TRANS.,(1988) N 2, 145-150
  作者：BELTON, JAMES G.、MCELHINNEY, R. STANLEY

  DOI：——

  日期：——
• The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1,2,5]oxadiazole dyes
  作者：Dongyang Li、Weijie Chen、Sheng Hua Liu、Xiaoqiang Chen、Jun Yin

  DOI：10.1016/j.cclet.2020.02.047

  日期：2020.11

  The different oxidation states of sulphur atom play a significant role on functional materials. In this work, a aryl-thioether and its sulphone substituted benzo[c][1,2,5]oxadiazole dyes were synthesized and utilized to determine thiol-containing amino acids. The result of selectivity experiments showed they detected the cysteine and homocysteine under physiological condition with negligible interference from other amino acids. In comparison to the thioether dye, the sulphone-based dye exhibited much faster response time for Cys and Hcy. However, the sulphone restricted its thiol-reactivity and bioimaging performance in living cells. By reducing the oxidation state of sulphur atom, we amazedly found that the sulfoxide-based dye still maintained high selectivity ultrafast response time for Cys/Hcy under physiological condition. It was worth mentioning that it also had high reactivity and good bioimaging performance that sulfone compounds did not have. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Belton, James G.; McElhinney, R Stanley, Journal of the Chemical Society. Perkin transactions I, 1988, p. 145 - 150
  作者：Belton, James G.、McElhinney, R Stanley

  DOI：——

  日期：——