(E,E)-1,4-dimethoxy-2,5-bis(4-hydroxy)styrylbenzene | 170661-05-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-1,4-dimethoxy-2,5-bis(4-hydroxy)styrylbenzene
• 英文别名: 1,4-bis[(E)-2-(4-hydroxyphenyl)ethenyl]-2,5-dimethoxybenzene；4-[(E)-2-[4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,5-dimethoxyphenyl]ethenyl]phenol
• CAS: 170661-05-9
• 化学式: C₂₄H₂₂O₄
• 分子量: 374.436
• InChiKey: KNEVEDWUZHSSBG-LQIBPGRFSA-N

物化性质

• 沸点：
  589.1±38.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-双(氯甲基)-2,5-二甲氧基苯 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 48.0h， 生成 (E,E)-1,4-dimethoxy-2,5-bis(4-hydroxy)styrylbenzene
  参考文献：
  名称：

  Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands

  摘要：

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential A beta imaging agents. To further explore their potency as F-19 MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-beta binding characteristics. The compounds showed a high affinity for Ab plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem F-19 NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.02.054

文献信息

• Phenylenevinylene oligomers by Mizoroki-Heck cross coupling reaction. Structural and optoelectronic characterization
  作者：Sandra E. Estrada、Cristian Ochoa-Puentes、Cesar A. Sierra

  DOI：10.1016/j.molstruc.2016.12.032

  日期：2017.4

  spectroscopies. The results showed that, with only one exception, the ED and EW groups at the ends of OPV systems lead to a bathochromic shift. This effect is intensified with the introduction of methoxy groups on the central ring. Consistent with these, the HOMO-LUMO gaps (ΔE) decreases as the strength of ED and EW substituents increases. The ED and EW substituents also lead to a decrease in the Φ f values

  摘要 为了研究分子结构对全反式亚苯基亚乙烯基低聚物 (OPV) 光学性质的影响，16 种 1,4-二苯乙烯基苯衍生物（ 1a-i 和 2a-g ）具有不同的给电子（ED）功能。 ) 和吸电子 (EW) 基团通过 Mizoroki-Heck 交叉偶联反应以中等至良好的产率（40-95%）合成。所实施的方法，经过我们小组先前报道的小改动，可以获得所需的乙烯基构型以及一种新型 OPV 化合物 (1h)。在通过几种技术（例如 FTIR、 1 H、 13 C 和固态核磁共振）进行结构表征后，特别强调通过紫外-可见光和荧光光谱研究它们的光学特性。结果表明，除了一个例外，OPV 系统末端的 ED 和 EW 组导致红移。随着在中心环上引入甲氧基，这种效果得到加强。与这些一致，HOMO-LUMO 间隙（ΔE）随着 ED 和 EW 取代基强度的增加而减小。ED 和 EW 取代基也会导致 Φ f 值降低。这种在
• Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands
  作者：Rob J.A. Nabuurs、Varsha V. Kapoerchan、Athanasios Metaxas、Sanne de Jongh、Maaike de Backer、Mick M. Welling、Wim Jiskoot、Albert D. Windhorst、Hermen S. Overkleeft、Mark A. van Buchem、Mark Overhand、Louise van der Weerd

  DOI：10.1016/j.bmc.2014.02.054

  日期：2014.4

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential A beta imaging agents. To further explore their potency as F-19 MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-beta binding characteristics. The compounds showed a high affinity for Ab plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem F-19 NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain. (C) 2014 Published by Elsevier Ltd.