7-bromo-5,5-difluoro-10-(p-tolyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide | 1222084-14-1

• 英文名称: 7-bromo-5,5-difluoro-10-(p-tolyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
• 英文别名: 3-bromo-4,4-difluoro-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene
• CAS: 1222084-14-1
• 化学式: C₁₆H₁₂BBrF₂N₂
• 分子量: 360.996
• InChiKey: DWAOHMAKLHBNOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  7-bromo-5,5-difluoro-10-(p-tolyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 14.5h， 生成 5,5-difluoro-7-(4-(1-hydroxyl cyclopentyl)-1H-1,2,3-triazol-1-yl)-10-(p-tolyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
  参考文献：
  名称：

  BODIPY based ‘click on’ fluorogenic dyes: application in live cell imaging

  摘要：

  The design, synthesis, and photophysical properties of new BODIPY-based fluorogenic 'click on' dyes are reported. CuAAC reaction of non-fluorescent BODIPY azide with a series of non-fluorescent alkyne molecules resulted in fluorescent triazoles which displayed up to 532-fold enhancement of fluorescence in the red region. Imaging studies confirmed the general trend of cell permeability and a cholesterol linked derivative exhibited selective localization into intracellular membranes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.003
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以457 mg的产率得到7-bromo-5,5-difluoro-10-(p-tolyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
  参考文献：
  名称：

  Synthesis of boron-dipyrromethene–ferrocene conjugates

  摘要：

  Synthesis, spectral, electrochemical and photophysical properties of four BODIPY-ferrocene conjugates in which one or two ferrocenyl groups were covalently connected either directly to boron-dipyrromethene framework or to meso-phenyl group of boron-dipyrromethene unit are described. The BODIPY-ferrocene conjugates were prepared by adopting different synthetic routes. The absorption studies indicated the presence of charge transfer band in BODIPY-ferrocene conjugates in which the ferrocenyl group(s) were directly connected to boron-dipyrromethene framework. The electrochemical studies on conjugates indicated that ferrocenyl group was difficult to oxidize whereas boron-dipyrromethene unit was easier to reduce. The conjugates were non-fluorescent due to electron transfer from ferrocene to boron-dipyrromethene unit. However, when ferrocene was oxidized to ferrocenium ion with an oxidizing agent, the conjugates exhibited fluorescence with decent quantum yields (0.17-0.31) and lifetimes (3.8-5.2 ns). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.01.009

文献信息

• Negishi reaction in BODIPY dyes. Unprecedented alkylation by palladium-catalyzed C–C coupling in boron dipyrromethene derivatives
  作者：Gonzalo Duran-Sampedro、Eduardo Palao、Antonia R. Agarrabeitia、Santiago de la Moya、Noël Boens、María J. Ortiz

  DOI：10.1039/c4ra00651h

  日期：——

  Negishi reactions of 3-halogen and 3,5-dihalogen substituted BODIPYs with different organozinc reagents are reported as the first examples of this valuable palladium-catalyzed C–C coupling reaction into the family of the BODIPY dyes. It is demonstrated that the Negishi coupling is especially useful for obtaining interesting alkylated BODIPYs, including synthetically-valuable asymmetrically-3,5-disubstituted

  3卤素和3,5-二卤素取代的BODIPY与不同的有机锌试剂的Negishi反应据报道是这种有价值的钯催化的C–C偶联反应进入BODIPY染料家族的第一个例子。已经证明，Negishi偶联对于获得令人感兴趣的烷基化的BODIPY特别有用，包​​括合成上有价值的不对称的3，5-二取代的BODIPY。
• Synthesis, structure, spectral, electrochemical and sensing properties of 3-amino boron-dipyrromethene and its derivatives
  作者：Emandi Ganapathi、Sheri Madhu、Tamal Chatterjee、Rajesh Gonnade、Mangalampalli Ravikanth

  DOI：10.1016/j.dyepig.2013.10.038

  日期：2014.3

  We report the synthesis of 3-amino boron-dipyrromethene (3-amino BODIPY) by treating 3-bromo boron-dipyrromethene (3-bromo BODIPY) initially with sodium azide in acetonitrile followed by triphenylphosphine(PPh3)/H2O in tetrahydrofuran in three steps under mild reaction conditions. In this reaction, 3-azido BODIPY which formed in the first step was not isolated but the 3-iminophosphorane BODIPY which

  我们报告的合成方法是先用叠氮化钠在乙腈中，然后用三苯膦（PPh 3）/ H 2 O在四氢呋喃中处理3-溴硼二吡咯亚甲基（3-溴BODIPY）来合成3-氨基硼二吡咯亚甲基（3-氨基BODIPY）。在温和的反应条件下分三步进行。在该反应中，没有分离出第一步中形成的3-叠氮基BODIPY，而是分离出了第二步中形成的3-亚氨基膦基BODIPY，并进行结晶学表征。通过多种光谱和X射线分析技术对3-氨基BODIPY进行了表征。为了测试BODIPY核心上胺官能团的反应性，我们制备了1-（中观-茴香基BODIPY）-3-苯基脲/硫脲衍生物在简单的反应条件下。我们的研究表明，1-（内消旋-anisyl BODIPY）-3-苯基硫脲可以作为特定chemodosimetric传感器充当对Hg 2+离子和1-（内消旋-anisyl BODIPY）-3-苯基脲，为与F比色和比例传感器-离子。