N-(2-((2-aminoethyl)disulfanyl)ethyl)-2-(7-hydroxycoumarin-4-yl)acetamide | 1326717-00-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(2-((2-aminoethyl)disulfanyl)ethyl)-2-(7-hydroxycoumarin-4-yl)acetamide
• 英文别名: N-[2-(2-aminoethyldisulfanyl)ethyl]-2-(7-hydroxy-2-oxochromen-4-yl)acetamide
• CAS: 1326717-00-3
• 化学式: C₁₅H₁₈N₂O₄S₂
• 分子量: 354.451
• InChiKey: QKMKXWQOWSRXJA-UHFFFAOYSA-N

物化性质

• 沸点：
  666.1±55.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-((2-aminoethyl)disulfanyl)ethyl)-2-(7-hydroxycoumarin-4-yl)acetamide 、 2-(4-(20,15,10-tris(4-hydroxyphenyl)porphyrin-5-yl)phenoxy)acetic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以68%的产率得到2-(4-(20,15,10-tris(4-hydroxyphenyl)porphyrin-5-yl)phenoxy)-N-(2-((2-(2-(7-hydroxycoumarin-4-yl)acetamido)ethyl)disulfanyl)ethyl)acetamide
  参考文献：
  名称：

  A Ratiometric Fluorescent Probe for Thiols Based on a Tetrakis(4-hydroxyphenyl)porphyrin–Coumarin Scaffold

  摘要：

  In this work, we have designed and synthesized the compound Ratio-HPSSC, based on a tetrakis(4-hydroxyphenyl)porphyrin coumarin scaffold, as a new ratiometric fluorescent probe for thiols. The ratiometric probe Ratio-HPSSC is highly selective and sensitive to thiols. Importantly, the novel ratiometric probe exhibited a remarkable change in emission color from red to blue. This key feature allows Ratio-HPSSC to be employed for thiol detection by simple visual inspection. Furthermore, we have demonstrated that Ratio-HPSSC is suitable for ratiometric fluorescence imaging of thiols in living cells. We believe that the new ratiometric probe will find interesting applications in chemistry, biology, and medicine.

  DOI：

  10.1021/jo201199k
• 作为产物：
  描述：

  tert-butyl 2-((2-(2-(7-hydroxycoumarin-4-yl)acetamido)ethyl)disulfanyl)ethylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以87%的产率得到N-(2-((2-aminoethyl)disulfanyl)ethyl)-2-(7-hydroxycoumarin-4-yl)acetamide
  参考文献：
  名称：

  A Ratiometric Fluorescent Probe for Thiols Based on a Tetrakis(4-hydroxyphenyl)porphyrin–Coumarin Scaffold

  摘要：

  In this work, we have designed and synthesized the compound Ratio-HPSSC, based on a tetrakis(4-hydroxyphenyl)porphyrin coumarin scaffold, as a new ratiometric fluorescent probe for thiols. The ratiometric probe Ratio-HPSSC is highly selective and sensitive to thiols. Importantly, the novel ratiometric probe exhibited a remarkable change in emission color from red to blue. This key feature allows Ratio-HPSSC to be employed for thiol detection by simple visual inspection. Furthermore, we have demonstrated that Ratio-HPSSC is suitable for ratiometric fluorescence imaging of thiols in living cells. We believe that the new ratiometric probe will find interesting applications in chemistry, biology, and medicine.

  DOI：

  10.1021/jo201199k