| 1392488-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 1392488-00-4
• 化学式: C₂₇H₂₈NO₂
• 分子量: 398.525
• InChiKey: INYIMDPFSLHFMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以148 mg的产率得到2-[2-(6-hydroxy-2,3-dihydro-1H-xanthen-4-yl)-vinyl]-1,3,3-trimethyl-3H-indolium
  参考文献：
  名称：

  荧光颗粒酶 A 底物可实现适应性免疫细胞活性的实时成像

  摘要：

  我们描述了颗粒酶 A 的近红外荧光底物，在生理水平上具有快速响应和酶敏感性。我们证明这些探针可用于与癌细胞共培养和离体组织中的 CTL 和 NK 细胞的实时成像，为监测肿瘤微环境中免疫系统的功能开辟了新途径。

  DOI：

  10.1002/anie.202216142
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 乙酸酐 、 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  De novo synthesis of phenolic dihydroxanthene near-infrared emitting fluorophores

  摘要：

  我们报告了一种灵活的de novo合成方法，通过一锅式串联反应，产率可达60-70%。

  DOI：

  10.1039/c5ob01223f

文献信息

• A Unique Approach to Development of Near-Infrared Fluorescent Sensors for in Vivo Imaging
  作者：Lin Yuan、Weiying Lin、Sheng Zhao、Wensha Gao、Bin Chen、Longwei He、Sasa Zhu

  DOI：10.1021/ja305802v

  日期：2012.8.15

  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.