2-(2-(9-(2-carboxyphenyl)-2,3,6,7,11,12-hexahydro-1H,5H,10H-chromeno[2,3-f]pyrido[3,2,1-ij]quinolin-13-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium perchlorate | 1354688-45-1

• 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: 2-(2-(9-(2-carboxyphenyl)-2,3,6,7,11,12-hexahydro-1H,5H,10H-chromeno[2,3-f]pyrido[3,2,1-ij]quinolin-13-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium perchlorate
• CAS: 1354688-45-1
• 化学式: C₃₉H₃₉N₂O₃*ClO₄
• 分子量: 683.201
• InChiKey: PEAKFTUAVWTMBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  49.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  145.02
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(2-(9-(2-carboxyphenyl)-2,3,6,7,11,12-hexahydro-1H,5H,10H-chromeno[2,3-f]pyrido[3,2,1-ij]quinolin-13-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium perchlorate 、 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  A ratiometric fluorescent molecular probe for visualization of mitochondrial temperature in living cells

  摘要：

  线粒体热力学是理解与稳态和能量平衡相关的细胞活动的关键。

  DOI：

  10.1039/c4cc10349a
• 作为产物：
  描述：

  8-羟基久洛里定 在 硫酸 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 9.5h， 生成 2-(2-(9-(2-carboxyphenyl)-2,3,6,7,11,12-hexahydro-1H,5H,10H-chromeno[2,3-f]pyrido[3,2,1-ij]quinolin-13-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium perchlorate
  参考文献：
  名称：

  A ratiometric fluorescent molecular probe for visualization of mitochondrial temperature in living cells

  摘要：

  线粒体热力学是理解与稳态和能量平衡相关的细胞活动的关键。

  DOI：

  10.1039/c4cc10349a

文献信息

• A Unique Class of Near-Infrared Functional Fluorescent Dyes with Carboxylic-Acid-Modulated Fluorescence ON/OFF Switching: Rational Design, Synthesis, Optical Properties, Theoretical Calculations, and Applications for Fluorescence Imaging in Living Animals
  作者：Lin Yuan、Weiying Lin、Yueting Yang、Hua Chen

  DOI：10.1021/ja209292b

  日期：2012.1.18

  Fluorescence imaging is one of the most powerful techniques for monitoring biomolecules in living systems. Fluorescent sensors with absorption and emission in the near-infrared (NIR) region are favorable for biological imaging . applications in living animals, as NIR light leads to minimum photodamage, deep tissue penetration, and minimum background autofluorescence interference. Herein, we have introduced a new strategy to design NIR functional dyes with the carboxylic-acid-controlled fluorescence on off switching mechanism by the spirocyclization. Based on the design strategy, we have developed a series of Changsha (CS1-6) NIR fluorophores, a unique new class of NIR functional fluorescent dyes, bearing excellent photophysical properties including large absorption extinction coefficients, high fluorescence quantum yields, high brightness, good photostability, and sufficient chemical stability. Significantly, the new CS1-6 NIR dyes are superior to the traditional rhodamine dyes with both absorption and emission in the NIR region while retaining the rhodamine-like fluorescence ON-OFF switching mechanism. In addition, we have performed quantum chemical calculations with the B3LYP exchange functional employing 6-31G* basis sets to shed light on the structure-optical properties of the new CS1-6 NIR dyes. Furthermore, using CS2 as a platform, we further constructed the novel NIR fluorescent TURN-ON sensor 7, which is capable of imaging endogenously produced HCIO in the living animals, demonstrating the value of our new CS NIR functional fluorescent dyes. We expect that the design strategy may be extended for development of a wide variety of NIR functional dyes with a suitable fluorescence-controlled mechanism for many useful applications in biological studies.