8-(O-methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1414345-89-3

• 英文名称: 8-(O-methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-8-methoxy-4-bora-3a,4a-diaza-s-indacene；8-methoxy 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；8-methoxy-BODIPY
• CAS: 1414345-89-3
• 化学式: C₁₀H₉BF₂N₂O
• 分子量: 222.002
• InChiKey: VFNXHJJOFNMVJN-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：
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• 环数：
  None
• sp3杂化的碳原子比例：
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• 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：

  8-(O-methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 以 乙腈 为溶剂， 反应 76.0h， 生成
  参考文献：
  名称：

  Concentration depending fluorescence of 8-(di-(2-picolyl))aminoBODIPY in solution

  摘要：

  An 8-dipicolylBODIPY derivative has been prepared and its photophysical properties evaluated under different conditions. Two different structures, hemicyanine and cyanine, are observed (depending on the solvent or the solution concentration). The hemicyanine form is not emissive whereas the cyanine form is fluorescent. This behavior is related with the planarity degree of the BODIPY core. The X-ray structure of the compound is reported and it shows that in solid state the hemicyanine form is present. The hemicyanine form seems to be stabilized by aggregation and is the main compound in concentrated solutions whereas the cyanine form is present in diluted solutions that are photochemically transformed into a new compound 3. Both species cyanine and hemicyanine, are able to complex Zn2+ being the complex with the cyanine form of higher stability. The presence of the cation precludes any ulterior transformation from the cyanine form. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.095
• 作为产物：
  描述：

  二-1H-吡咯-1-基甲酮 在 sodium carbonate 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 29.08h， 生成 8-(O-methyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis of Meso-Halogenated BODIPYs and Access to Meso-Substituted Analogues

  摘要：

  8-Halogenated boradiaza-s-indacenes can be efficiently prepared from dipyrrylketones. The new dyes react smoothly with nucleophiles to yield N-, O-, and S-substituted chromophores, as well as transition-metal-catalyzed cross-coupling reactions. The nature of the new substitutent has a strong influence on the spectral properties of the dyes.

  DOI：

  10.1021/ol3028225

文献信息

• 8-Alkoxy- and 8-Aryloxy-BODIPYs: Straightforward Fluorescent Tagging of Alcohols and Phenols
  作者：Juan O. Flores-Rizo、Ixone Esnal、Carlos A. Osorio-Martı́nez、César F. A. Gómez-Durán、Jorge Bañuelos、Iñigo López Arbeloa、Keith H. Pannell、Alejandro J. Metta-Magaña、Eduardo Peña-Cabrera

  DOI：10.1021/jo400417h

  日期：2013.6.21

  We demonstrate herein that both alcohols and phenols can be tagged with a BODIPY (borondipyrromethene) moiety to yield highly fluorescent products. Thus, 8-(methylthio)-BODIPY (1) undergoes an SNAr-type reaction with a host of alcohols and phenols in the presence of a base and a Cu(I) additive. The BODIPY dyes bearing alkoxy or nonfunctionalized phenoxy moieties are characterized by a highly efficient fluorescence emission, regardless of the media, in the blue-green part of the visible region. Complementary to this, the presence of electron-donor groups at the aryl ring leads to an intramolecular charge-transfer process, which quenches the fluorescence mainly in polar media. In addition to simple alcohols and phenols, four natural products (eugenol, menthol, cholesterol, and estrone) were labeled in a simple fashion. X-ray structures of the cholesterol and estrone derivatives are discussed. In fact, the BODIPY bearing cholesterol stands out as a bright fluorescence biological marker.