1,3,5-三溴-2-苯基甲氧基苯 | 88486-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,3,5-三溴-2-苯基甲氧基苯
• 中文别名: 2-(苄氧基)-1,3,5-三溴苯
• 英文名称: 2-benzyloxy-1,3,5-tribromobenzene
• 英文别名: benzyl-(2,4,6-tribromo-phenyl)-ether；Benzyl-(2,4,6-tribrom-phenyl)-aether；2-(Benzyloxy)-1,3,5-tribromobenzene；1,3,5-tribromo-2-phenylmethoxybenzene
• CAS: 88486-72-0
• 化学式: C₁₃H₉Br₃O
• 分子量: 420.926
• InChiKey: AVIFETXUEKGOSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P273,P305+P351+P338
• 危险性描述：
  H315,H319,H335,H413

反应信息

• 作为反应物：
  描述：

  1,3,5-三溴-2-苯基甲氧基苯 在 硝酸 作用下， 生成 (4-nitro-benzyl)-(2,4,6-tribromo-phenyl)-ether
  参考文献：
  名称：

  Holmes; Ingold, Journal of the Chemical Society, 1925, vol. 127, p. 1810

  摘要：

  DOI：
• 作为产物：
  描述：

  溴甲苯 、 三溴苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以97%的产率得到1,3,5-三溴-2-苯基甲氧基苯
  参考文献：
  名称：

  Toward Optimization of the Linker Substructure Common to Transthyretin Amyloidogenesis Inhibitors Using Biochemical and Structural Studies

  摘要：

  To develop potent and highly selective transthyretin (TTR) amyloidogenesis inhibitors, it is useful to systematically optimize the three substructural elements that compose a typical TTR kinetic stabilizer: the two aryl rings and the linker joining them. Herein, we evaluated 40 bisaryl molecules based on 10 unique linker substructures to determine how these linkages influence inhibitor potency and selectivity. These linkers connect one unsubstituted aromatic ring to either a 3,5-X 2 or a 3,5-X 2-4-OH phenyl substructure (X = Br or CH 3). Coconsideration of amyloid inhibition and ex vivo plasma TTR binding selectivity data reveal that direct connection of the two aryls or linkage through nonpolar E-olefin or -CH 2CH 2- substructures generates the most potent and selective TTR amyloidogenesis inhibitors exhibiting minimal undesirable binding to the thyroid hormone nuclear receptor or the COX-1 enzyme. Five high-resolution TTR.inhibitor crystal structures (1.4-1.8 A) provide insight into why such linkers afford inhibitors with greater potency and selectivity.

  DOI：

  10.1021/jm800435s

文献信息

• Okawara et al., Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1955, vol. 58, p. 924,925
  作者：Okawara et al.

  DOI：——

  日期：——
• Toward Optimization of the Linker Substructure Common to Transthyretin Amyloidogenesis Inhibitors Using Biochemical and Structural Studies
  作者：Steven M. Johnson、Stephen Connelly、Ian A. Wilson、Jeffery W. Kelly

  DOI：10.1021/jm800435s

  日期：2008.10.23

  To develop potent and highly selective transthyretin (TTR) amyloidogenesis inhibitors, it is useful to systematically optimize the three substructural elements that compose a typical TTR kinetic stabilizer: the two aryl rings and the linker joining them. Herein, we evaluated 40 bisaryl molecules based on 10 unique linker substructures to determine how these linkages influence inhibitor potency and selectivity. These linkers connect one unsubstituted aromatic ring to either a 3,5-X 2 or a 3,5-X 2-4-OH phenyl substructure (X = Br or CH 3). Coconsideration of amyloid inhibition and ex vivo plasma TTR binding selectivity data reveal that direct connection of the two aryls or linkage through nonpolar E-olefin or -CH 2CH 2- substructures generates the most potent and selective TTR amyloidogenesis inhibitors exhibiting minimal undesirable binding to the thyroid hormone nuclear receptor or the COX-1 enzyme. Five high-resolution TTR.inhibitor crystal structures (1.4-1.8 A) provide insight into why such linkers afford inhibitors with greater potency and selectivity.
• Auwers, Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 93
  作者：Auwers

  DOI：——

  日期：——
• Holmes; Ingold, Journal of the Chemical Society, 1925, vol. 127, p. 1810
  作者：Holmes、Ingold

  DOI：——

  日期：——
• Rational Design of Chelated Aluminum Complexes toward Highly Efficient and Thermally Stable Electron-Transporting Materials
  作者：Na Lin、Juan Qiao、Lian Duan、Jie Xue、Liduo Wang

  DOI：10.1021/cm5011604

  日期：2014.6.24

  Two novel chelated aluminum complexes, bis(2-methyl-8-quinolinato)(2,6-di(pyridin-3-yl)phenolato)Al(III) (BPyAlq) and bis(2-methyl-8-quinolinato)(2,4,w6-tri-(pyridin-3-yl)phenolato)Al(III) (TPyAlq), have been designed and synthesized by introducing the electron-withdrawing pyridine moieties into the ancillary ligand. Their single-crystal and molecular structures, thermal and photophysical properties, and electron-transporting (ET) capabilities were systematically investigated in comparison with the parent complex bis(2-methyl-8-quinolinato)(4-phenyl-phenolato)Al(III) (BAlq). The introduction of the pyridine moieties helps to not only greatly lower the LUMO and HOMO energy levels but also bring about extra strong intra- and intermolecular interactions, thus significantly improving the electron-injection (El) and ET capabilities of the involved materials. BPyAlq and TPyAlq exhibited significantly higher glass-transition temperatures (106 and 141 degrees C) than BAlq (92 degrees C). The electron-only devices based on 0, BPyAlq or TPyAlq showed more than 2 orders of magnitude higher current density than that of BAlq, indicating much higher ET/EI capabilities. Their excellent ET/Ei properties were investigated via the phosphorescent OLEDs using fac-tris(2-phenylpyridine)iridium as the green emitter. The devices with BPyAlq and TPyAlq as an electron-transporting layer (ETL) demonstrated superior performance compared to those using BAlq, remarkably lowering the drive voltage and improving efficiencies. In particular, the green PhOLEDs with BPyAlq as an ETL exhibited the maximum current and external quantum efficiency of 59.8 cd A(-1), 17.3% with small efficiency roll-off.