| 892505-43-0

• CAS: 892505-43-0
• 化学式: C₁₄H₁₇BF₂N₂S
• 分子量: 294.176
• InChiKey: LLCKZFBRZOJZLA-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  、 2-溴苯基硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 噻吩-2-甲酸亚铜(I) 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到
  参考文献：
  名称：

  Scope and Limitations of the Liebeskind–Srogl Cross-Coupling Reactions Involving the Biellmann BODIPY

  摘要：

  Several new examples of meso-(het)aryIBODIPY were prepared via the Liebeskind-Srogl (L-S) cross-coupling reaction of the Biellmann BODIPYs (1a,b) and aryl- and heteroarylboronic acids in good to excellent yield. It was shown that this reaction could be carried out under microwave heating to shorten reaction times and/or increase the yield. It was illustrated that organostannanes also participate in the L-S reaction to give the corresponding BODIPY analogues in short reaction times and also with good to excellent yields. We analyze the role of the substituent at the sensitive meso position in the photophysical signatures of these compounds. In particular, the rotational motion of the aryl ring and the electron donor ability of the anchored moieties rule the nonradiative pathways and, hence, have a deep impact in the fluorescence efficiency.

  DOI：

  10.1021/acs.joc.5b00731

文献信息

• 8-Alkenylborondipyrromethene dyes. General synthesis, optical properties, and preliminary study of their reactivity
  作者：Ismael J. Arroyo、Rongrong Hu、Ben Zhong Tang、Fabiola I. López、Eduardo Peña-Cabrera

  DOI：10.1016/j.tet.2011.07.067

  日期：2011.9

  prepared using alkenylboronic acids in good to excellent yields (79–97%), and one additional example was prepared from an alkenylstannane in 74% yield. The products display Michael acceptor-like reactivity. The alkenyl fragment quenches the fluorescence of the BODIPY core, which is turned back on by reducing the double bond.

  通过Liebeskind-Srogl交叉偶联，从8-硫甲基取代的BODIPY开始，制备了一系列新的8-链烯基BODIPY染料。使用链烯基硼酸制备了十种衍生物，收率良好至优异（79-97％），另外一个实例是从链烯基锡烷以74％的产率制备。该产品表现出迈克尔受体样的反应性。烯基片段淬灭了BODIPY核心的荧光，通过还原双键将其重新打开。
• Straightforward Synthetic Protocol for the Introduction of Stabilized C Nucleophiles in the BODIPY Core for Advanced Sensing and Photonic Applications
  作者：Brenda D. Gutiérrez-Ramos、Jorge Bañuelos、Teresa Arbeloa、Iñigo López Arbeloa、Paulina E. González-Navarro、Kazimierz Wrobel、Luis Cerdán、Inmaculada García-Moreno、Angel Costela、Eduardo Peña-Cabrera

  DOI：10.1002/chem.201405233

  日期：2015.1.19

  C nucleophiles to the meso position of BODIPY (4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene) is reported. Soft nucleophiles generated by deprotonation of 1,3‐dicarbonyl derivatives smoothly displace the 8‐methylthio group from 8‐(methylthio)BODIPY analogues in the presence of CuI thiophenecarboxylate in stoichiometric amounts at room temperature. Seven highly fluorescent new derivatives are prepared with varying

  据报道，有一个简单的合成方案可以将稳定的1,3-二羰基C亲核体直接掺入BODIPY（4,4-二氟-4-硼3a，4a-二氮杂s-茚并四烯）的内消旋位置。在Cu I存在下，由1,3-二羰基衍生物去质子化生成的软亲核试剂可将8-甲硫基与8-（甲硫基）BODIPY类似物平稳地置换在室温下化学计量的噻吩羧酸盐。在较短的反应时间（5-30分钟）内，制备了七种具有高荧光强度的新衍生物，收率各不相同（20-92％）。新染料的出色的光物理性质使其可以专注于以前从未分析过的被稳定C亲核试剂取代的BODIPY（如pH传感器和液态和固态激光器）进行的应用，突出了本工作中描述的合成方案的相关性。这些染料在绿色光谱区域具有强大的紫外线吸收能力以及高效且稳定的激光发射，这是目前正在进行的具有相关应用的先进光子材料开发面临的最大挑战之一。实际上，只有绿色才能发出光的有机染料
• Novel <i>meso</i>-Polyarylamine-BODIPY Hybrids: Synthesis and Study of Their Optical Properties
  作者：Erik Lager、Jianzhao Liu、Angélica Aguilar-Aguilar、Ben Zhong Tang、Eduardo Peña-Cabrera

  DOI：10.1021/jo802519b

  日期：2009.3.6

  A series of 14 meso-polyarylamine-BODIPY (borondipyrromethene) hybrids of the general structure A were synthesized. Two methods were used to prepare them. The first protocol involved a direct Liebeskind-Srogl cross-coupling of thiomethylbodipys 1-2 with arylaminoboronic acids (4 examples, 75-98%). The second method involves a two-step sequence: a Liebeskind-Srogl reaction to prepare 6 meso-bromoarylbodipys (58-83%) followed by a Suzuki coupling of these Br-containing BODIPYs with arylaminoboronic acids (10 examples, 44-84%). Seven of these derivatives displayed emission in the near-infrared region. The optical properties of compound 18 were rationalized in terms of its crystal structure.
• FormylBODIPYs: Privileged Building Blocks for Multicomponent Reactions. The Case of the Passerini Reaction
  作者：Diana E. Ramírez-Ornelas、Enrique Alvarado-Martínez、Jorge Bañuelos、Iñigo López Arbeloa、Teresa Arbeloa、Héctor M. Mora-Montes、Luis A. Pérez-García、Eduardo Peña-Cabrera

  DOI：10.1021/acs.joc.5b02893

  日期：2016.4.1

  Eleven formyl-containing BODIPY dyes were prepared by means of either the Liebeskind-Srogl cross-coupling reaction or the Vilsmeier reaction. These dyes were used as components in the Passerini reaction to give highly substituted BODIPY dyes. A joined spectroscopic and theoretical characterization of the synthesized compounds was conducted to unravel the impact of the structural rigidity/flexibility on the photophysical signatures. These dyes were tested as fluorescent trackers for phagocytosis. Additionally, they proved to be useful to stain different blood cells with an intense and stable signal at a very low exposure time.