(E)-3,5-dibromo-1-styrylbenzene | 1070240-19-5

• 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)-3,5-dibromo-1-styrylbenzene
• 英文别名: 1,3-dibromo-5-[(E)-2-phenylethenyl]benzene
• CAS: 1070240-19-5
• 化学式: C₁₄H₁₀Br₂
• 分子量: 338.041
• InChiKey: QJCUQPWBTMQSOI-VOTSOKGWSA-N

物化性质

• 沸点：
  387.9±31.0 °C(Predicted)
• 密度：
  1.648±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-3,5-dibromo-1-styrylbenzene 在 palladium 10% on activated carbon 、 氢气 、 zinc dibromide 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以46%的产率得到1,3-dibromo-5-phenethylbenzene
  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
• 作为产物：
  描述：

  3,5-二溴苯甲醛 、 溴甲苯 在 亚磷酸三乙酯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.5h， 以14%的产率得到(E)-3,5-dibromo-1-styrylbenzene
  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

• Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C–H Activation
  作者：Xiaofan Jia、Lucas I. Frye、Weihao Zhu、Shunyan Gu、T. Brent Gunnoe

  DOI：10.1021/jacs.0c03935

  日期：2020.6.10

  Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we

  芳烃烯基化通常通过后期过渡金属介导的 C(sp2)-C(sp2) 交叉偶联实现，但该策略通常需要预官能化底物（例如，具有卤化物或拟卤化物）和/或在芳烃。过渡金属介导的芳烃 CH 活化和烯基化提供了一种功能化芳烃底物的替代方法。在此，我们报告了由芳烃和苯乙烯进行铑催化氧化芳烃烯基化以制备二苯乙烯和二苯乙烯衍生物。芳烃和烯烃上的几个官能团（包括氟化物、氯化物、三氟甲基、酯、硝基、乙酸酯、氰化物和醚基团）的反应是成功的。单取代芳烃的反应对间位和对位的烯基化具有选择性，通常具有大约 2 个：1 选择性，分别。白藜芦醇和 (E)-1,2,3-三甲氧基-5-(4-甲氧基苯乙烯基)苯 (DMU-212) 是通过这种单步方法以高产率合成的。与钯催化的比较表明，铑催化对单取代芳烃的间位官能化具有更高的选择性，并且Rh催化对卤素基团的耐受性更好。
• Design of cyclometallated 5-π-delocalized donor-1,3-di(2-pyridyl)benzene platinum(II) complexes with second-order nonlinear optical properties
  作者：Nicolò Baggi、Eleonora Garoni、Alessia Colombo、Claudia Dragonetti、Stefania Righetto、Dominique Roberto、Julien Boixel、Véronique Guerchais、Simona Fantacci

  DOI：10.1016/j.poly.2017.11.051

  日期：2018.2

  The effect on the second-order nonlinear optical properties of the nature of the π-delocalized moiety in the position 5 of a 1,3-di(2-pyridyl)benzene cyclometallated to a platinum(II) center was investigated. The influence of the substitution of a double bond with a triple bond as bridge between a triphenylamino group and the cyclometallated phenyl ring was studied and turned out to be negligible.

  研究了在环化成铂（II）中心的1,3-二（2-吡啶基）苯的5位上的π-离域部分的性质对二级非线性光学性质的影响。研究了用三键取代双键作为三苯基氨基基团与环金属化苯环之间的桥的影响，结果可忽略不计。值得注意的是，这种新型的易于制备的具有环金属化的5-苯乙烯基-1,3-二（2-吡啶基）苯的铂（II）配合物具有良好的二阶NLO响应，这是通过EFISH技术在溶液中测定的。它是光子学中应用的一个很好的候选者。
• 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.