| 1392487-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• CAS: 1392487-97-6
• 化学式: C₃₃H₃₈ClN₂
• 分子量: 498.131
• InChiKey: KUKHEAOKPGURDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  6.25
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  、 间苯二酚 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 以59.5%的产率得到5-[2-(1,3,3-trimethylindol-2-ylidene)ethylidene]-7,8-dihydro-6H-xanthen-3-one
  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