8-(2,4-difluorophenyl)quinoline | 849416-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(2,4-difluorophenyl)quinoline
• CAS: 849416-81-5
• 化学式: C₁₅H₉F₂N
• 分子量: 241.24
• InChiKey: XUVGTJGSAXLLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(2,4-difluorophenyl)quinoline 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 3-(5-methylpyridin-2-yl)benzonitrile 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到8-(2,4-difluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)quinoline
  参考文献：
  名称：

  Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines

  摘要：

  我们报告了一种方便的方法，用于高度位点选择性地对8-芳基喹啉进行硼化反应。在[Ir(OMe)(cod)]2和2-苯基吡啶衍生的配体存在下，使用双(二甲基苯基)二硼烷作为硼化试剂，反应顺利进行。这些反应在许多官能团的高选择性下发生，提供了一系列硼化的8-芳基喹啉，产率从良好到优异，选择性也非常好。这种方法形成的硼化化合物可以通过已知的转化反应转化为各种重要的合成子。

  DOI：

  10.1055/a-1506-3884
• 作为产物：
  描述：

  1-溴-2,4-二氟苯 、 8-喹啉三氟甲烷磺酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 联硼酸频那醇酯 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 24.0h， 以86%的产率得到8-(2,4-difluorophenyl)quinoline
  参考文献：
  名称：

  Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines

  摘要：

  我们报告了一种方便的方法，用于高度位点选择性地对8-芳基喹啉进行硼化反应。在[Ir(OMe)(cod)]2和2-苯基吡啶衍生的配体存在下，使用双(二甲基苯基)二硼烷作为硼化试剂，反应顺利进行。这些反应在许多官能团的高选择性下发生，提供了一系列硼化的8-芳基喹啉，产率从良好到优异，选择性也非常好。这种方法形成的硼化化合物可以通过已知的转化反应转化为各种重要的合成子。

  DOI：

  10.1055/a-1506-3884

文献信息

• Metal Complexes and Their Use as the Emitting Constituent in Electronic Components, in Particular in Electroluminescent Display Devices
  申请人：Stössel Philipp

  公开号：US20090292080A1

  公开（公告）日：2009-11-26

  The present invention describes new metal complexes. Such compounds can be used as functional materials in a variety of different applications which can in the broadest sense be considered part of the electronics industry. The compounds of the invention have the formulae (1) and (1a).

  该发明描述了新的金属配合物。这些化合物可以用作各种不同应用中的功能材料，这些应用可以广义地被认为是电子工业的一部分。该发明的化合物具有式（1）和（1a）。
• Synthesis, Characterization, and Photophysical Properties of Iridium Complexes with an 8-Phenylquinoline Framework. The First Six-Membered Chelated Iridium Complexes for Electroluminance
  作者：Hao-Chun Li、Pi-Tai Chou、Ya-Hui Hu、Yi-Ming Cheng、Rai-Shung Liu

  DOI：10.1021/om049192n

  日期：2005.3.1

  A series of six-membered chelated iridium complexes bearing an 8-phenylquinoline framework have been prepared and characterized with an X-ray diffraction study. The photophysical properties of these complexes were examined with appropriate spectroscopic methods. The results, in combination with ab initio approaches, led us to clearly assign various electronic transition states. One salient feature for these red complexes is the appearance of a dual strong absorption band around 425-500 nm, which incorporates a state mixing between (MLCT)-M-1 and pi-pi* manifolds. These complexes show deep red phosphorescent emissions (650-680 nm), with short lifetimes of 1.7-3.0 mu s and moderate quantum yields of 0.05-0.11 in deaerated CH3CN. The electroluminance performance of these species shows a promising perspective in the OLED display. One representative, Ir[8-(3,5-difluorophenyl)quinoline](2)(acac) (4c), shows a eta(ext) value of 2.04% at J = 20 mA/cm(2) and the maximum brightness is 3427 cd/m(2) (x = 0.68, y = 0.32) with a full width at half-maximum of only 60 nm at 16 V, demonstrating the first six-membered chelated iridium complexes to suit applications in OLED devices.
• Substrate‐Rhodium Cooperativity in Photoinduced <i>ortho</i> ‐Alkynylation of Arenes
  作者：Argha Saha、Animesh Ghosh、Srimanta Guin、Sanjib Panda、Dibya Kanti Mal、Abhirup Majumdar、Munetaka Akita、Debabrata Maiti

  DOI：10.1002/anie.202210492

  日期：2022.10.17

  AbstractIn the realm of metallaphotocatalytic C−H activation strategy, the direct excitation of the transition metal which plays the dual role of light energy harnessing alongside performing the bond breaking and forming is a rare phenomenon. In this context we have developed the first photo‐induced Rh‐catalyzedortho‐alkynylation under ambient conditions without the requirement of silver salt, photocatalyst (PC) or any engineered substrate or catalyst. The transformation functions by the specific cooperative effect of a six‐membered rhodacycle which is the photo‐responsive species. The catalytic system allows the conjugation of arenes with sp3‐rich pharmacophoric fragments. The control experiments as well as the computational studies resolve the mechanistic intricacies for this transformation. An outer sphere electron transfer process from Rh to alkynyl radical is operative for the present photo‐induced transformation over the more common oxidative addition or 1,2‐migratory insertion pathways.
• METALLKOMPLEXE UND DEREN VERWENDUNG ALS DIE EMITTIERENDE KOMPONENTE IN ELEKTRONISCHEN BAUTEILEN, BESONDERS IN ELEKTROLUMINESZENTEN ANZEIGEVORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP1820227A1

  公开（公告）日：2007-08-22
• EP1820227B1
  申请人：——

  公开号：EP1820227B1

  公开（公告）日：2014-05-07