tert-butyl 2-((2-(2-(7-hydroxycoumarin-4-yl)acetamido)ethyl)disulfanyl)ethylcarbamate | 1326716-99-7

• 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: tert-butyl 2-((2-(2-(7-hydroxycoumarin-4-yl)acetamido)ethyl)disulfanyl)ethylcarbamate
• 英文别名: tert-butyl N-[2-[2-[[2-(7-hydroxy-2-oxochromen-4-yl)acetyl]amino]ethyldisulfanyl]ethyl]carbamate
• CAS: 1326716-99-7
• 化学式: C₂₀H₂₆N₂O₆S₂
• 分子量: 454.568
• InChiKey: ZHGQFOMVAIVUTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  165
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-((2-(2-(7-hydroxycoumarin-4-yl)acetamido)ethyl)disulfanyl)ethylcarbamate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 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：

  7-羟基香豆素-4-乙酸 、 T-BOC-胱胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以81%的产率得到tert-butyl 2-((2-(2-(7-hydroxycoumarin-4-yl)acetamido)ethyl)disulfanyl)ethylcarbamate
  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

文献信息

• A Ratiometric Fluorescent Probe for Thiols Based on a Tetrakis(4-hydroxyphenyl)porphyrin–Coumarin Scaffold
  作者：Xiaowei Cao、Weiying Lin、Quanxing Yu

  DOI：10.1021/jo201199k

  日期：2011.9.16

  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.