4-(octadecyloxy)phenyl boronic acid | 221211-68-3

• 英文名称: 4-(octadecyloxy)phenyl boronic acid
• CAS: 221211-68-3
• 化学式: C₂₄H₄₃BO₃
• 分子量: 390.415
• InChiKey: PCRAWCWYDRVBSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  28.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(octadecyloxy)phenyl boronic acid 、 N,N′-(pyridine-2,6-diyl)dibenzenecarboximidamide 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到1-(4-Octadecoxyphenyl)-3,11-diphenyl-2,4,10,12-tetraza-13-azonia-1-boranuidatricyclo[7.3.1.05,13]trideca-2,5(13),6,8,11-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
• 作为产物：
  描述：

  硬脂基溴 在 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丁酮 为溶剂， 反应 24.5h， 生成 4-(octadecyloxy)phenyl boronic acid
  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

• Design and Synthesis of a New Family of Fluorinated Liquid Crystals
  作者：Valentine G. Nenajdenko、Aleksey A. Goldberg、Vasily M. Muzalevskiy、Elizabeth S. Balenkova、Aleksey V. Shastin

  DOI：10.1002/chem.201203315

  日期：2013.2.11

  A convenient and simple three‐step pathway to the new family of CF2CF2S‐bridged alkanes and CF2S‐, CF2O‐bridged alkenes and alkynes was elaborated by using catalytic olefination reaction as a key step of the synthetic sequence. The obtained compounds revealed attractive liquid crystalline characteristics.

  通过使用催化烯化反应作为合成序列的关键步骤，阐述了通往新的CF 2 CF 2 S-桥联烷烃和CF 2 S-，CF 2 O-桥联烯烃和炔烃家族的便捷，简单的三步途径。所获得的化合物显示出有吸引力的液晶特性。
• Suzuki-Miyaura Reaction of Chloroarenes Using Pd(PPh₃)₄ as Catalyst
  作者：Thies Thiemann、Yasuko Tanaka、Soleiman Hisaindee、Maitha Kaabi

  DOI：10.3184/030823410x12624523028293

  日期：2010.1

  The reactivity of a number of chloroarenes was investigated and chloro–nitroarenes were found to undergo facile arylation with Pd(PPh₃)₄ / [Pd(PPh₃)₂Cl₂/n·PPh₃] as catalyst. Furthermore, 4–chlorobenzaldehyde underwent arylation under the conditions, albeit with a higher catalyst loading.

  研究人员对多种氯代烯烃的反应活性进行了调查，发现氯代硝基烯烃在 Pd(PPh3)4 / [Pd(PPh3)2Cl2/n-Ph3] 催化剂的作用下可发生简单的芳基化反应。此外，4-氯苯甲醛也在该条件下发生了芳基化反应，尽管催化剂负载量较高。