1-Fluoro-3,11-bis(4-methylphenyl)-2,12-dioxa-4,10-diaza-13-azonia-1-boranuidatricyclo[7.3.1.05,13]trideca-3,5(13),6,8,10-pentaene | 1430837-32-3

• 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: 1-Fluoro-3,11-bis(4-methylphenyl)-2,12-dioxa-4,10-diaza-13-azonia-1-boranuidatricyclo[7.3.1.05,13]trideca-3,5(13),6,8,10-pentaene
• 英文别名: 1-fluoro-3,11-bis(4-methylphenyl)-2,12-dioxa-4,10-diaza-13-azonia-1-boranuidatricyclo[7.3.1.05,13]trideca-3,5(13),6,8,10-pentaene
• CAS: 1430837-32-3
• 化学式: C₂₁H₁₇BFN₃O₂
• 分子量: 373.194
• InChiKey: FPBUSDQDYXZNAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N'-bis(4-methylbenzoyl)-2,6-diaminopyridine 、 三氟化硼乙醚 以 甲苯 为溶剂， 反应 5.0h， 以85%的产率得到1-Fluoro-3,11-bis(4-methylphenyl)-2,12-dioxa-4,10-diaza-13-azonia-1-boranuidatricyclo[7.3.1.05,13]trideca-3,5(13),6,8,10-pentaene
  参考文献：
  名称：

  Fluorescent Modular Boron Systems Based on NNN- and ONO-Tridentate Ligands: Self-Assembly and Cell Imaging

  摘要：

  We have synthesized a series of new fluorescent boron systems 1a-c and 2a-d based on nitrogen (NNN) or nitrogen and oxygen (ONO)-containing tridentate ligands. These novel dyes are characterized by high thermal and chemical stability. They show large Stokes shifts (mostly above 3200 cm(-1)) and quantum yields in solution and in the solid state up to 40%. The easy, modular synthesis facilitates the convenient variation of the axial substituent on the central boron atom, allowing the functionalization of this dye for biochemical use. Introducing a long alkyl chain with a phenyl spacer at this axial position enables the self-assembly of the boron compound 2d to form a fluorescent vesicle, which is able to encapsulate small molecules such as sulforhodamine. Additionally, boron compound 2d was found to serve as a dye for cell imaging since it has the capability of binding to the nuclear membranes of HeLa cells. With phospholipids such as DOPC, giant unilamelar vesicles (GUV) are formed. These results demonstrate the wide applicability of this new boron system in supramolecular and medicinal chemistry.

  DOI：

  10.1021/jo4003745

文献信息

• Fluorescent Modular Boron Systems Based on NNN- and ONO-Tridentate Ligands: Self-Assembly and Cell Imaging
  作者：Christoph Glotzbach、Ulrike Kauscher、Jens Voskuhl、N. Seda Kehr、Marc C. A. Stuart、Roland Fröhlich、Hans J. Galla、Bart Jan Ravoo、Kazuhiko Nagura、Shohei Saito、Shigehiro Yamaguchi、Ernst-Ulrich Würthwein

  DOI：10.1021/jo4003745

  日期：2013.5.3

  We have synthesized a series of new fluorescent boron systems 1a-c and 2a-d based on nitrogen (NNN) or nitrogen and oxygen (ONO)-containing tridentate ligands. These novel dyes are characterized by high thermal and chemical stability. They show large Stokes shifts (mostly above 3200 cm(-1)) and quantum yields in solution and in the solid state up to 40%. The easy, modular synthesis facilitates the convenient variation of the axial substituent on the central boron atom, allowing the functionalization of this dye for biochemical use. Introducing a long alkyl chain with a phenyl spacer at this axial position enables the self-assembly of the boron compound 2d to form a fluorescent vesicle, which is able to encapsulate small molecules such as sulforhodamine. Additionally, boron compound 2d was found to serve as a dye for cell imaging since it has the capability of binding to the nuclear membranes of HeLa cells. With phospholipids such as DOPC, giant unilamelar vesicles (GUV) are formed. These results demonstrate the wide applicability of this new boron system in supramolecular and medicinal chemistry.