7-(trimethylsilylethylethynyl)-4-hydroxymethylcoumarin | 736957-96-3

• 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: 7-(trimethylsilylethylethynyl)-4-hydroxymethylcoumarin
• CAS: 736957-96-3
• 化学式: C₁₅H₁₆O₃Si
• 分子量: 272.376
• InChiKey: XMYSMVAJGDFWBN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.5±45.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-(trimethylsilylethylethynyl)-4-hydroxymethylcoumarin 在 甲醇 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以72%的产率得到7-ethynyl-4-hydroxymethyl-chromen-2-one
  参考文献：
  名称：

  A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction:  Modulation of the Fluorescence Emission via ³(n,π*)−(π,π*) Inversion

  摘要：

  Chemoselective ligation reactions represent a powerful approach for labeling of proteins or small molecules in a biological environment. We report here a fluorogenic probe that is activated by click chemistry, a highly versatile bio-orthogonal and chemoselective ligation reaction which is based on the azide moiety as the functional group. The electron-donating properties of the triazole ring that is formed in the course of the coupling reaction was effectively utilized to modulate the fluorescence output of an electronically coupled coumarin fluorophore. Under physiological conditions the probe is essentially nonfluorescent and undergoes a bright emission enhancement upon ligation with an azide. Time-resolved emission spectroscopy and semiempirical quantum-mechanical calculations suggest that the fluorescence switching is due to an inversion of the energy ordering of the emissive 1(pi,pi*) and nonemissive 3(n,pi*) excited states. The rapid kinetics of the ligation reaction render the probe attractive for a wide range of applications in biology, analytical chemistry, or material science.

  DOI：

  10.1021/ja049684r
• 作为产物：
  描述：

  4-(溴甲基)-7-羟基苯并吡喃-2-酮 在 四(三苯基膦)钯 、 水 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 46.0h， 生成 7-(trimethylsilylethylethynyl)-4-hydroxymethylcoumarin
  参考文献：
  名称：

  A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction:  Modulation of the Fluorescence Emission via ³(n,π*)−(π,π*) Inversion

  摘要：

  Chemoselective ligation reactions represent a powerful approach for labeling of proteins or small molecules in a biological environment. We report here a fluorogenic probe that is activated by click chemistry, a highly versatile bio-orthogonal and chemoselective ligation reaction which is based on the azide moiety as the functional group. The electron-donating properties of the triazole ring that is formed in the course of the coupling reaction was effectively utilized to modulate the fluorescence output of an electronically coupled coumarin fluorophore. Under physiological conditions the probe is essentially nonfluorescent and undergoes a bright emission enhancement upon ligation with an azide. Time-resolved emission spectroscopy and semiempirical quantum-mechanical calculations suggest that the fluorescence switching is due to an inversion of the energy ordering of the emissive 1(pi,pi*) and nonemissive 3(n,pi*) excited states. The rapid kinetics of the ligation reaction render the probe attractive for a wide range of applications in biology, analytical chemistry, or material science.

  DOI：

  10.1021/ja049684r