5,7-二溴-8-苄氧基喹啉 | 84165-50-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 5,7-二溴-8-苄氧基喹啉
• 英文名称: 8-benzyloxy-5,7-dibromoquinoline
• 英文别名: 5,7-dibromo-8-benzyloxyquinoline；8-(Benzyloxy)-5,7-dibromoquinoline；5,7-dibromo-8-phenylmethoxyquinoline
• CAS: 84165-50-4
• 化学式: C₁₆H₁₁Br₂NO
• 分子量: 393.077
• InChiKey: GLRLAIQRBWDBGX-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C(Solv: ethanol (64-17-5))
• 沸点：
  481.2±40.0 °C(Predicted)
• 密度：
  1.680±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，干燥

制备方法与用途

该化合物8-苄氧基-5,7-二溴喹啉主要用于科研领域。

反应信息

• 作为反应物：
  描述：

  5,7-二溴-8-苄氧基喹啉 在 tris(triphenylphosphano)palladium 、 1,4-环己二烯 、 palladium on activated charcoal 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  Synthesis, characterization and DFT calculation of 4-fluorophenyl substituted tris(8-hydroxyquinoline)aluminum(III) complexes

  摘要：

  New 4-fluorophenyl substituted 8-hydroxyquinoline derivatives, 5-(4-fluorophenyl)quinolin-8-ol and 5,7-bis(4-fluorophenyl)quinolin-8-ol, were synthesized and characterized by spectroscopic methods. The aluminum complexes of 5-(4-fluorophenyl)quinolin-8-ol (AlQF) and of 5,7-bis(4-fluorophenyl)quinolin-8-ol (AlQF2) exhibit strong fluorescence emission centered at 525 nm and 530 nm respectively. The quantum yield of both complexes were enhanced compared to the parent tris(8-hydroxyquinolinato)aluminum(III) complex. Electronic structures and photophysical properties of the new complexes were investigated theoretically by ab initio and density functional theory (DFT) and time dependent DFT (TD-DFT). Geometries of the ground state (S-0) and the first excited state (S-1) of the new complexes were optimized at the B3LYP/6-31G(d) functional and configuration interaction singles (CIS) method respectively. The aryl substituents were found to contribute significantly to the frontier molecular orbitals (FMOs). We have observed that in both cases the lowest occupied molecular orbital (LUMO) energy decreases while the energy of the highest occupied molecular orbital is slightly increased. The most significant increase was observed for AlQF2. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.08.055
• 作为产物：
  描述：

  8-羟基喹啉 在 溴 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 10.33h， 生成 5,7-二溴-8-苄氧基喹啉
  参考文献：
  名称：

  Synthesis, characterization and electronic effects investigations of new 5,7-disubstituted tris(8-quinolinolate)Al(III) complexes

  摘要：

  Eight 5,7-diaryl-8-hydroxyquinoline ligands were synthesized and characterized by H-1, C-13 NMR spectroscopy and mass spectrometry. The electron-donating and electron-withdrawing aryl groups were attached to the 5- and 7-positions of the quinolinolate ring via Suzuki coupling reaction. The aluminum complexes of these ligands exhibited successful tuning in the emission color, covering a large segment of the visible spectrum. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.12.007

文献信息

• Improved Preparation of 4,6,6-Trimethyl-1,3,2-dioxaborinane and Its Use in a Simple [PdCl₂(TPP)₂]-Catalyzed Borylation of Aryl Bromides and Iodides
  作者：Nageswaran PraveenGanesh、Pierre Yves Chavant

  DOI：10.1002/ejoc.200800526

  日期：2008.9

  We describe a convenient preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane (MethylPentaneDiolBorane, MPBH) and demonstrate that it is an excellent reagent for the [PdCl2(PPh3)2]-catalyzed borylation of aryl bromides and iodides. The corresponding boronic esters undergo rapid Suzuki coupling reactions in the presence of cesium fluoride. Thus, MPBH is an excellent alternative to pinacolborane for Pd-catalyzed

  我们描述了 4,6,6-三甲基-1,3,2-二氧硼烷（MethylPentaneDiolBorane，MPBH）的方便制备，并证明它是 [PdCl2(PPh3)2]-催化芳基溴化物和碘化物。在氟化铯存在下，相应的硼酸酯会发生快速的 Suzuki 偶联反应。因此，对于 Pd 催化的硼化和交叉偶联反应，MPBH 是频哪醇硼烷的绝佳替代品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Luminescent Tungsten(VI) Complexes: Photophysics and Applicability to Organic Light-Emitting Diodes and Photocatalysis
  作者：Kwan-Ting Yeung、Wai-Pong To、Chenyue Sun、Gang Cheng、Chensheng Ma、Glenna So Ming Tong、Chen Yang、Chi-Ming Che

  DOI：10.1002/anie.201608240

  日期：2017.1.2

  phosphorescence (red) of comparable intensity, which could be used for ratiometric luminescent sensing. Solution‐processed organic light‐emitting diodes (OLEDs) based on 1 d showed a stable yellow emission with an external quantum efficiency (EQE) and luminance up to 4.79 % and 1400 cd m−2 respectively. These tungsten(VI) complexes were also applied in light‐induced aerobic oxidation reactions.

  描述了两个系列的空气稳定的发光钨（VI）配合物的合成，激发态动力学及其应用。这些钨（VI）络合物在固态和溶液中显示磷光，在室温下薄膜的发射量子产率高达22％（在mCP中为5％）。包含5,7-二苯基-8-羟基喹啉酸酯配体的复合物2 c显示出强度相当的快速荧光（蓝绿色）和磷光（红色），可用于比率式发光传感。基于1 d的溶液处理有机发光二极管（OLED）显示稳定的黄色发射，具有外部量子效率（EQE），亮度高达4.79％和1400 cd m -2分别。这些钨（VI）配合物也用于光诱导的需氧氧化反应。
• Molecular fluorescent pH-probes based on 8-hydroxyquinoline
  作者：Stefan Kappaun、Tanja Sović、Franz Stelzer、Alexander Pogantsch、Egbert Zojer、Christian Slugovc

  DOI：10.1039/b600912c

  日期：——

  Three 5,7-π-extended 8-benzyloxyquinolines, namely 5,7-diphenyl-, 5,7-bis(biphenyl-4-yl)- and 5,7-bis(4-dibenzothiophenyl)-8-benzyloxyquinoline were prepared and investigated as fluorescent pH-probes in nonaqueous solution. Absorption and photoluminescence spectra of the introduced compounds also including the starting material 8-benzyloxy-5,7-dibromoquinoline as well as their N-protonated counterparts were recorded and the results were rationalized by quantum-chemical calculations. A pronounced red shift of the emission occurred upon protonation of the non halogenated derivatives, while the dibromo-derivative is hardly emissive and is virtually not protonated under the conditions used. The diphenyl- and the bis(biphenyl)-derivative especially show promising photoluminescence quantum yields both in the parent and the protonated state making them candidates for the active component in pH sensing applications.

  制备并研究了三种 5,7-π 延伸的 8-苄氧基喹啉，即 5,7-二苯基、5,7-双（联苯-4-基）和 5,7-双（4-二苯并噻吩基）-8-苄氧基喹啉，作为非水溶液中的荧光 pH 探针。研究人员记录了所引入化合物（也包括起始材料 8-苄氧基-5,7-二溴喹啉）及其 N-质子化对应物的吸收光谱和光致发光光谱，并通过量子化学计算对结果进行了合理解释。非卤代衍生物质子化时，发射发生了明显的红移，而二溴衍生物几乎不发射，在所用条件下几乎不质子化。尤其是二苯基和双（联苯）衍生物在母体和质子化状态下都显示出良好的光致发光量子产率，使它们成为 pH 值传感应用中的候选活性成分。
• Perfluoroalkylated lignin as a catalyst support with varying phase behavior
  申请人：Brizius Glen Leon

  公开号：US09221040B2

  公开（公告）日：2015-12-29

  Multi-phase biopolymer catalyst support systems, methods of synthesizing a biopolymer material for use in a multi-phase biopolymer catalyst support system, and methods for catalyzing reactions with a multi-phase biopolymer catalyst support system are described.

  描述了多相生物聚合物催化剂支撑系统、用于多相生物聚合物催化剂支撑系统的生物聚合物材料合成方法，以及使用多相生物聚合物催化剂支撑系统催化反应的方法。
• The Use of Phase-Transfer Catalysis for the Synthesis of Phenyl and 8-Quinolinyl Ethers
  作者：WANG Chin-Hsien、LIU Xiang-Te、CHAO Xiao-Hun

  DOI：10.1055/s-1982-29976

  日期：——