[4-[[2-chloro-5-[2-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)ethenyl]-7,8-dihydro-6H-xanthen-3-yl]oxymethyl]phenyl]boronic acid | 1392488-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [4-[[2-chloro-5-[2-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)ethenyl]-7,8-dihydro-6H-xanthen-3-yl]oxymethyl]phenyl]boronic acid
• CAS: 1392488-04-8
• 化学式: C₃₄H₃₄BClNO₄
• 分子量: 566.912
• InChiKey: NLKGZMLVKJYNCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.93
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  、 4-溴甲基苯硼酸频哪醇酯 在 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 以65.7%的产率得到[4-[[2-chloro-5-[2-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)ethenyl]-7,8-dihydro-6H-xanthen-3-yl]oxymethyl]phenyl]boronic acid
  参考文献：
  名称：

  A Unique Approach to Development of Near-Infrared Fluorescent Sensors for in Vivo Imaging

  摘要：

  Near-infrared (NIR) fluorescent sensors have emerged as promising molecular tools for imaging biomolecules in living systems. However, NIR fluorescent sensors are very challenging to be developed. Herein, we describe the discovery of a new class of NIR fluorescent dyes represented by 1a/1c/1e, which are superior to the traditional 7-hydroxycoumarin and fluorescein with both absorption and emission in the NIR region while retaining an optically tunable hydroxyl group. Quantum chemical calculations with the B3LYP exchange functional employing 6-31G(d) basis sets provide insights into the optical property distinctions between 1a/1c/1e and their alkoxy derivatives. The unique optical properties of the new type of fluorescent dyes can be exploited as a useful strategy for development of NIH fluorescent sensors. Employing this strategy, two different types of NIR fluorescent sensors, NIR-H2O2 and NIR-thiol, for H2O2 and thiols, respectively, were constructed. These novel sensors respond to H2O2 or thiols with a large turn-on NIR fluorescence signal upon excitation in the NIR region. Furthermore, NIR-H2O2 and NIR-thiol are capable of imaging endogenously produced H2O2 and thiols, respectively, not only in living cells but also in living mice, demonstrating the value of the new NIR fluorescent sensor design strategy. The new type of NIR dyes presented herein may open up new opportunities for the development of NIR fluorescent sensors based on the hydroxyl functionalized reactive sites for biological imaging applications in living animals.

  DOI：

  10.1021/ja305802v