5-chloro-4,4-difluoro-3-methoxyl-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene | 877616-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-4,4-difluoro-3-methoxyl-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 3-chloro-5-methoxide-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)；3-chloro-5-methoxy-8-(4-tolyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；3-methoxy-5-chloro-4,4-difluoro-4-bora-8-(4-methylphenyl)-3a,4a-diaza-s-indacene；3-chloro-5-methoxide-BODIPY；4-Chloro-2,2-difluoro-12-methoxy-8-(4-methylphenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene；4-chloro-2,2-difluoro-12-methoxy-8-(4-methylphenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 877616-00-7
• 化学式: C₁₇H₁₄BClF₂N₂O
• 分子量: 346.572
• InChiKey: JJORRJUQPGZJRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-4,4-difluoro-3-methoxyl-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene 、 二甲基吡啶胺 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以57%的产率得到5-N-di(2-picolyl)amine-4,4-difluoro-3-methoxyl-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  基于BODIPY的高铜选择性比率荧光传感器

  摘要：

  一个新的比率荧光传感器（1）对Cu 2+基于4,4-二氟-4-硼-3a，4a-二氮杂-小号-indacene（BODIPY）与二（2-吡啶甲基）胺（DPA）作为离子识别亚基已经合成并进行了这项工作进行了研究。1对不同金属离子的结合能力，例如碱金属和碱土金属离子（Na +，K +，Mg 2 +，Ca 2+）和其他金属离子（Ba 2 +，Zn 2 +，Cd 2 +，Fe 2+，Fe 3+，Pb 2 +，Ni 2 +，Co 2 +，Hg 2+，Ag +）已通过紫外可见光谱和荧光光谱法进行了检查。图1显示了在所有测试金属离子中对Cu 2+的高选择性，并且在可见光激发波长下激发时I 582 / I 558中的荧光增强了约10倍。1和Cu 2+的结合模式是通过研究Job图，荧光滴定法的非线性拟合和ESI质量确定的1：1化学计量。

  DOI：

  10.1002/cjoc.201200260
• 作为产物：
  描述：

  5-(4-methylphenyl)dipyrromethane 在 N-氯代丁二酰亚胺 、 三氟化硼乙醚 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 5-chloro-4,4-difluoro-3-methoxyl-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  A BODIPY analogue from the tautomerization of sodium 3-oxide BODIPY

  摘要：

  The introduction of hydroxy group to the 3- or 5-position of 4,4-difluoro-4-bora-3a,4a-diazaindacene (BODIPY) results in unexpected tautomerization to BDPONa with interesting structural and photophysical properties. The core of BDPONa is an anion with sodium cation as counter-ion. BDPONa displays strong fluorescence in organic solvents. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.04.018

文献信息

• Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution
  作者：Taoufik Rohand、Mukulesh Baruah、Wenwu Qin、Noël Boens、Wim Dehaen

  DOI：10.1039/b512756d

  日期：——

  The BODIPY chromophore can be easily modified by nucleophilic mono- or disubstitution of 3,5-dichloroBODIPY with O-, N-, S- and C-nucleophiles. Absorption and fluorescence spectral data of the new BODIPY derivatives are also reported.

  BODIPY色基可以通过对3,5-二氯BODIPY进行O-、N-、S-和C-亲核试剂的单取代或双取代进行简单修改。新BODIPY衍生物的吸收和荧光光谱数据也被报道。
• Boron Dipyrromethene Analogs with Phenyl, Styryl, and Ethynylphenyl Substituents:  Synthesis, Photophysics, Electrochemistry, and Quantum-Chemical Calculations
  作者：Wenwu Qin、Taoufik Rohand、Wim Dehaen、John N. Clifford、Kris Driesen、David Beljonne、Bernard Van Averbeke、Mark Van der Auweraer、Noël Boens

  DOI：10.1021/jp073547+

  日期：2007.9.1

  induced by substitution. The fluorescence quantum yields of the ethenylaryl and ethynylaryl analogs are significantly higher that those of the aryl-substituted dyes. The 3,5-diethynylaryl dye has the highest fluorescence quantum yield (approximately 1.0) and longest lifetime (around 6.5 ns) among the BODIPY dyes studied. The differences in the photophysical properties of the dyes are also reflected in their

  通过钯与适当的3,5-dichloroBODIPY衍生物进行偶联反应，合成了七个在3-（或3,5-）位置带有一个或两个苯基，乙烯基苯基和乙炔基苯基取代基的七氟硼氮杂茚并七基荧光化合物。通过UV / vis吸收，稳态和时间分辨，研究了3-（或3,5-）位置上的各种取代基对光谱和光物理性质的影响，作为溶剂的函数荧光法和理论建模。相对于相关的不对称3,5-二取代的染料，对称的3,5-二取代的染料的发射最大值移至更长的波长（30至60 nm）。苯乙烯基取代基的引入在吸收光谱和发射光谱中引起最大的红移。与芳基取代的基团相比，具有乙炔基芳基的BODIPY衍生物也将光谱最大值移至更长的波长，但程度低于苯乙烯基化合物。量子化学计算证实了这些趋势，并为由取代引起的光谱移动提供了理论依据。乙烯基芳基和乙炔基芳基类似物的荧光量子产率显着高于芳基取代的染料的荧光量子产率。在所研究的BODIPY染料中，3,5-二乙
• Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes
  作者：Eduard Fron、Eduardo Coutiño-Gonzalez、Lesley Pandey、Michel Sliwa、Mark Van der Auweraer、Frans C. De Schryver、Joice Thomas、Zeyuan Dong、Volker Leen、Mario Smet、Wim Dehaen、Tom Vosch

  DOI：10.1039/b900786e

  日期：——

  Synthetic details and stationary and time-resolved photophysical properties of five BODIPY derivatives containing chalcogen atoms are presented. The photophysical data are compared to those of a chlorine atom containing BODIPY, acting as a reference. A strong impact in the HOMO–LUMO transition energy is achieved via nucleophilic substitution with chalcogen based units. Going from oxygen to tellurium a bathochromic shift in both absorption and emission spectra from the green to the near infrared region was observed. By employing fluorescence single photon timing experiments in two solvents of different polarity, the excited state dynamics and their solvent dependence indicate the presence of a mechanism involving a photoinduced charge transfer that dramatically affects the optical radiative processes of these derivatives.

  本文介绍了五种含有查尔根原子的 BODIPY 衍生物的合成细节、静态和时间分辨光物理性质。光物理数据与作为参照物的含有氯原子的 BODIPY 的光物理数据进行了比较。通过亲核取代查尔根单元，对 HOMO-LUMO 转换能产生了强烈的影响。从氧气到碲，吸收光谱和发射光谱都发生了从绿色到近红外区域的浴色转变。通过在两种不同极性的溶剂中进行荧光单光子定时实验，激发态动力学及其与溶剂的相关性表明，存在着一种涉及光诱导电荷转移的机制，这种机制极大地影响了这些衍生物的光学辐射过程。
• BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine
  作者：Li-Ya Niu、Ying-Shi Guan、Yu-Zhe Chen、Li-Zhu Wu、Chen-Ho Tung、Qing-Zheng Yang

  DOI：10.1021/ja309079f

  日期：2012.11.21

  We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.
• A BODIPY analogue from the tautomerization of sodium 3-oxide BODIPY
  作者：Peng-Zhong Chen、Hai-Rong Zheng、Li-Ya Niu、Yu-Zhe Chen、Li-Zhu Wu、Chen-Ho Tung、Qing-Zheng Yang

  DOI：10.1016/j.cclet.2015.04.018

  日期：2015.6

  The introduction of hydroxy group to the 3- or 5-position of 4,4-difluoro-4-bora-3a,4a-diazaindacene (BODIPY) results in unexpected tautomerization to BDPONa with interesting structural and photophysical properties. The core of BDPONa is an anion with sodium cation as counter-ion. BDPONa displays strong fluorescence in organic solvents. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.