4-(hydroxymethyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate | 736957-95-2

• 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: 4-(hydroxymethyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate
• 英文别名: [4-(Hydroxymethyl)-2-oxochromen-7-yl] trifluoromethanesulfonate
• CAS: 736957-95-2
• 化学式: C₁₁H₇F₃O₆S
• 分子量: 324.234
• InChiKey: AGFLARKRUVLGIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(hydroxymethyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate 在 甲醇 、 四(三苯基膦)钯 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.25h， 生成 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 水 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 4-(hydroxymethyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate
  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

文献信息

• Practical and Scalable Synthesis of 7-Azetidin-1-yl-4-(hydroxy­methyl)coumarin: An Improved Photoremovable Group
  作者：Pablo Rivera-Fuentes、Giovanni Bassolino、Elias Halabi

  DOI：10.1055/s-0036-1591742

  日期：2018.2

  Published as part of the Bürgenstock Special Section 2017 Future­ Stars in Organic Chemistry Abstract 7-Substituted 4-methylcoumarin derivatives are widely employed as photoprotecting groups in chemistry and biology. We have recently shown that the 7-azetidinylated version of this photocage releases carboxylic acids in aqueous solution more efficiently than the traditionally used 7-diethylamino variant

  作为Bürgenstock专栏2017年有机化学中的未来之星的一部分发布 抽象的 7-取代的4-甲基香豆素衍生物在化学和生物学中被广泛用作光保护基团。我们最近显示，这种光笼的7-氮杂环丁烷基化版本比传统使用的7-二乙氨基变体更有效地在水溶液中释放羧酸。在这里，我们提出了一种稳健且可扩展的途径来制备7-氮杂环丁烷基化的醇（一种对各种离去基团进行光保护的有用前体）及其在制备模型磷酸盐，磺酸盐和氨基甲酸酯衍生物中的用途。 7-取代的4-甲基香豆素衍生物在化学和生物学中被广泛用作光保护基团。我们最近显示，这种光笼的7-氮杂环丁烷基化版本比传统使用的7-二乙氨基变体更有效地在水溶液中释放羧酸。在这里，我们提出了一种稳健且可扩展的途径来制备7-氮杂环丁烷基化的醇（一种对各种离去基团进行光保护的有用前体）及其在制备模型磷酸盐，磺酸盐和氨基甲酸酯衍生物中的用途。