8-(S-phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1414345-85-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 8-(S-phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 8-(phenylmercapto)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；difluoroboradiaza-s-indacene；BODIPY；dipyrrometheneboron difluoride；2,2-Difluoro-8-phenylsulfanyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1414345-85-9
• 化学式: C₁₅H₁₁BF₂N₂S
• 分子量: 300.14
• InChiKey: IETAESPJFLVADW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二-1H-吡咯-1-基甲酮 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 8-(S-phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  BODIPY-BASED DYES FOR DIGITAL SPATIAL PROTEOMICS

  摘要：

  本公开提供了用于检测/鉴定氨基酸和测序多肽分子的组合物、试剂盒和方法。

  公开号：

  US20230194539A1

文献信息

• Dual emission channels for sensitive discrimination of Cys/Hcy and GSH in plasma and cells
  作者：Yuanlin Zhang、Xiangmin Shao、Yue Wang、Fuchao Pan、Ruixue Kang、Fangfang Peng、Zhentao Huang、Weijuan Zhang、Weili Zhao

  DOI：10.1039/c4cc08687b

  日期：——

  A new selective fluorescent chemosensor for the detection of GSH, Cys/Hcy from dual emission channels.

  一种新的选择性荧光化学传感器，用于检测谷胱甘肽（GSH）、半胱氨酸/半胱氨酸（Cys/Hcy），具有双发射通道。
• Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY
  作者：Robinson I. Roacho、Alejandro Metta-Magaña、Eduardo Peña-Cabrera、Keith Pannell

  DOI：10.1039/c4ob01892c

  日期：——

  Phenylthiol performs a thiol exchange with 8-MeS-BODIPY and activates/substitutes the 3,5 positions forming a tri-thiolated BODIPY.

  苯硫醇与8-MeS-BODIPY进行硫醇交换反应，激活/取代3,5位置，形成三硫代化的BODIPY。
• Formation of 8-RS-BODIPYs via direct substitution of 8-MeS-BODIPY by RSH (R = Et, Pr, Bu, ^tBu, <i>n</i>-C₁₂H₂₅, C₆H₅, <i>p</i>-MeC₆H₄, <i>p</i>-MeOC₆H₄, and 2,6-Me₂C₆H₃)
  作者：Robinson I. Roacho、Alejandro Metta-Magaña、José L. Belmonte-Vázquez、Eduardo Peña-Cabrera、Keith H. Pannell

  DOI：10.1139/cjc-2015-0303

  日期：2016.3

  Reactions between 8-RS-BODIPY (R = Me, 1) and alkyl and aryl thiols were readily accomplished in dichloromethane to provide a synthetic pathway to a range of new 8-organothio-BODIPYs in good yield. The new alkyl 8-RS-BODIPYs (R = Et, 2; Pr, 3; Bu, 4; ^tBu, 5; n-dodecyl, 6) exhibit absorption and emission properties essentially unchanged from those of 1 whereas the arylthio analogs (R = Ph, 7; 2,6-Me₂C₆H₃, 8; p-MeC₆H₄, 9; p-MeOC₆H₄, 10) exhibit no fluorescence with the exception of 7, and then only in hexane. In common with other related 8-substituted BODIPYs, the new 8-alkylthio-BODIPY dyes show decreasing fluorescence intensity as solvent polarity increases. Compounds 2, 3, 7, and 8 were characterized via single-crystal X-ray analysis; the alkyl derivatives 2 and 3 exhibited planar BODIPY cores with co-planar organothio- substituents whereas the aryl derivatives exhibited both BODIPY core deformation and significant twisting about the S–C (8) bond removing co-planarity between the aryl group and the distorted BODIPY core. These deformations coincide with the significantly reduced emission properties.

  8-RS-BODIPY (R = Me, 1)与烷基和芳基硫醇之间的反应在二氯甲烷中很容易完成，从而提供了一种合成新型8-有机硫基-BODIPY的途径，收率良好。新的烷基8-RS-BODIPY（R = Et，2; Pr，3; Bu，4; tBu，5; n-十二烷基，6）的吸收和发射性质与1基本相同，而芳硫基类似物（R = Ph，7; 2,6-Me2C6H3，8; p-MeC6H4，9; p-MeOC6H4，10）除7在己烷中有荧光外，其他均无荧光。与其他相关的8-取代BODIPY一样，新的8-烷基硫基-BODIPY染料在溶剂极性增加时显示出荧光强度降低的特征。化合物2、3、7和8通过单晶X射线分析进行了表征；烷基衍生物2和3表现出平面BODIPY核心和共面有机硫基取代基，而芳基衍生物表现出BODIPY核心变形和S-C（8）键的显着扭曲，消除了芳基团与扭曲的BODIPY核心之间的共面性。这些变形与显着降低的发射性质相一致。
• Compound and color conversion film comprising same
  申请人：LG CHEM, LTD.

  公开号：US11479566B1

  公开（公告）日：2022-10-25

  The present specification relates to a compound, and a color conversion film, a backlight unit, and a display device, including the same.

  本规格说明涉及一种化合物，以及包括该化合物的颜色转换膜、背光装置和显示装置。
• Synthesis of <i>Meso</i>-Halogenated BODIPYs and Access to <i>Meso</i>-Substituted Analogues
  作者：Volker Leen、Peijia Yuan、Lina Wang、Noël Boens、Wim Dehaen

  DOI：10.1021/ol3028225

  日期：2012.12.21

  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.