1,1,2,3-四甲基-1H-苯并[e]吲哚六氟磷酸盐 | 372081-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,1,2,3-四甲基-1H-苯并[e]吲哚六氟磷酸盐
• 中文别名: 1,1,2,3-四甲基-1H-苯并[E]吲哚六氟磷酸盐
• 英文名称: 1,1,2,3-tetramethyl-1H-benzo[e]indol-3-ium hexafluorophosphate
• 英文别名: 1H-benz[e]indolium, 1,1,2,3-tetramethyl hexafluorophosphate；1,1,2,3-Tetramethyl-1H-benzo[e]indolium Hexafluorophosphate；1,1,2,3-tetramethylbenzo[e]indol-3-ium;hexafluorophosphate
• CAS: 372081-65-7
• 化学式: C₁₆H₁₈N*F₆P
• 分子量: 369.29
• InChiKey: OBEJDMPKHNFDIA-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于丙酮

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,2,3-四甲基-1H-苯并[e]吲哚六氟磷酸盐 、 2-(phenylselanyl)benzaldehyde 以 乙醇 为溶剂， 反应 12.0h， 以0.1 g的产率得到(E)-1,1,3-trimethyl-2-(2-(phenylselanyl)styryl)-1H-benzo[e]indol-3-ium
  参考文献：
  名称：

  含半菁的二苯基硒化物嵌入式探针“ HemiSe”，其中SePh2保持降低，可选择性检测活细胞中的超氧化物

  摘要：

  已经开发出一种简单的一步法荧光探针HemiSe合成物，用于检测超氧化物（O 2 .-）。当存在其他竞争性ROS / RNS /金属离子时，探针会特别与O 2 .-发生反应。掺入二苯硒化物以通过光致电子转移（PET）光机制的作用完全淬灭半菁单元的荧光。然而，在加入O 2 .-之后，由于在半花菁的C = C键与O 2 .-通过亲核攻击发生反应，因此潜在的荧光团恢复了荧光。蓝色发射的增加是由于内部的双键反应HemiSe之后，荧光量子产率（Φ）增加到0.45。检出限（LOD）为11.9 n m。时间相关研究表明，HemiSe能够以高灵敏度，高选择性，在宽的pH范围13分钟内检测超氧化物，并通过与确认黄嘌呤/黄嘌呤氧化酶生物化学测定（λ EM = 439纳米）。在RAW 264.7巨噬细胞活细胞中进行的一项研究还表明，HemiSe无毒，可渗透细胞（实验对数P = 2.11）；共聚焦成像结果表明，He

  DOI：

  10.1002/asia.201801339

文献信息

• Solvent-dependent ratiometric fluorescent merocyanine dyes: Spectral properties, interaction with BSA as well as biological applications
  作者：Dengfeng Gao、Anyang Li、Li Guan、Xianghan Zhang、L.Y. Wang

  DOI：10.1016/j.dyepig.2016.02.020

  日期：2016.6

  series of merocyanine dyes with excellent spectral properties were synthesized through changing the heterocyclic base structure for protein labeling and imaging in biological science, such as living cells and living mice. Dyes 7c–7h showed solvent-dependent changes on emission wavelength and fluorescence intensity in water and hydrophobic solvents, which were further analyzed by theoretical calculations

  通过改变生物医学中诸如活细胞和活小鼠的蛋白质标记和成像的杂环碱基结构，合成了一系列具有优异光谱特性的部花青染料。染料7c-7h在水和疏水性溶剂中的发射波长和荧光强度显示出溶剂依赖性的变化，并通过理论计算和吸收光谱对其进行了进一步分析。染料7d与牛血清白蛋白（BSA）的相互作用显示出对溶剂/蛋白质环境的明显比例荧光响应，具有报告蛋白质构象变化的潜力。对细胞毒性和生物成像能力的研究表明，染料7b–7h 表现出低的细胞毒性，并且可以染色活细胞的细胞质，可用于在活体小鼠的应用剂量下具有明亮荧光的成像，这被建议用作生物学中成像的荧光试剂。
• Spiro N-oxidized pyrrolidone-appended hemicyanine: Synthesis, lower pH-sensing and colormetric temperature sensing
  作者：Lanying Wang、Yongqiang Zhang、Mengqi Yan、Zhiwu Fan、Junlong Zhao

  DOI：10.1016/j.dyepig.2020.108261

  日期：2020.10

  especially in acidic and alkaline solvents. Spirocyclic dye 2a displays an excellent pH dependent behavior and responds linearly to extreme acidic conditions in the pH ranges of 1-4. The absorption spectra studies on opening-ring reaction reveal that acid and heat dual stimulation can induce opening-ring of 2a, which exhibits temperature-responsive linear in the range of 25–45 °C, behaving a colorimetric thermometer

  合成了三种新颖的螺-N-氧化吡咯烷酮半胱氨酸衍生物，并通过1 H NMR，13 C NMR，UV-Vis和HRMS进行了表征。通过单晶X射线衍射分析确定了螺环染料2a及其开环产物2aa的分子结构。UV-vis光谱显示出三种螺环衍生物的显着溶剂变色行为，尤其是在酸性和碱性溶剂中。螺环染料2a表现出出色的pH依赖行为，并且在1-4的pH范围内对极端酸性条件线性响应。关于开环反应的吸收光谱研究表明，酸和热的双重刺激可以诱发2a的开环，该开环在25–45°C的范围内表现出温度响应线性，表现为比色温度计。这些特性为2a-c用作刺激反应分子开关提供了可能性。
• Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry
  作者：X.H. Zhang、Q. Liu、H.J. Shi、L.Y. Wang、Y.L. Fu、X.C. Wei、L.F. Yang

  DOI：10.1016/j.dyepig.2013.09.011

  日期：2014.1

  A series of dimethine cyanine dyes, used as fluorescent probes, were synthesized under microwave irradiation, and identified by H-1 NMR, IR, elemental analysis and HRMS. The investigation of their spectral properties in phosphate-buffer saline (PBS) showed that the absorption and emission maxima of the dyes were in the region 370-480 nm and 471-569 nm, respectively. The properties of the dyes as fluorescent probes for living cells imaging and flow cytometry were investigated. The results showed that dyes 1, 2, 8 or 9 could penetrate an intact cell membrane, stained the cell nuclear and exhibited bright fluorescence. Little background interference, low cell cytotoxicity and little photobleaching were showed during the imaging tests. The dyes 1, 8 and 9 could be applied in flow cytometry and dye 1/PI, dye 8/PI or dye 9/PI couple could be proposed as double staining agents to measure sperm cell viability. Thus the dyes represented the cell-permeant fluorescent probes. (C) 2013 Elsevier Ltd. All rights reserved.
• Approach to Introducing Substituent on the Dipole Conjugate Chain: The D−π–A Methine Chain Electrophilic Substitution
  作者：Lanying Wang、Mengqi Yan、Borui Zhang、Junlong Zhao、Wenting Deng、Wenxia Lin、Li Guan

  DOI：10.1021/acs.orglett.7b03345

  日期：2018.1.5

  The D-pi-A methine chain electrophilic substitution reactions for directly introducing some functional groups to the dipole conjugate chain, with mild conditions and good yields, are disclosed. This method is shown to efficiently replace the hydrogen on the D-pi-A methine chain with an electrophile to synthesize methine-substituted Cy3.5 in one step.