2-(4-biphenylmethyl)phenol | 496863-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-biphenylmethyl)phenol
• 英文别名: 2-([1,1'-biphenyl]-4-ylmethyl)phenol；2-[(4-Phenylphenyl)methyl]phenol
• CAS: 496863-23-1
• 化学式: C₁₉H₁₆O
• 分子量: 260.335
• InChiKey: AQIFOHWBQOJPLB-UHFFFAOYSA-N

物化性质

• 沸点：
  428.2±24.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-biphenylmethyl)phenol 在 二氯双(三邻甲苯膦)合钯(II) 、 四丁基溴化铵 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 ethyl 2-(1,1'-biphenyl-3-(4-biphenylmethyl)-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate
  参考文献：
  名称：

  4,4′-Unsymmetrically substituted 3,3′-biphenyl alpha helical proteomimetics as potential coactivator binding inhibitors

  摘要：

  A series of unsymmetrically substituted biphenyl compounds was designed as alpha helical proteomimetics with the aim of inhibiting the binding of coactivator proteins to the nuclear hormone receptor coactivator binding domain. These compounds were synthesized in good overall yields in seven steps starting from 2-bromoanisole. The final products were evaluated using cotransfection reporter gene assays and mammalian two-hybrid competitive inhibition assays to demonstrate their effectiveness as competitive binding inhibitors. The results from this study indicate that these proteomimetics possess the ability to inhibit coactivator-receptor interactions, but via a mixed mode of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.051
• 作为产物：
  描述：

  2-溴苯甲醚 在 三乙基硅烷 、 碘 、 三溴化硼 、 碳酸氢钠 、 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.17h， 生成 2-(4-biphenylmethyl)phenol
  参考文献：
  名称：

  4,4′-Unsymmetrically substituted 3,3′-biphenyl alpha helical proteomimetics as potential coactivator binding inhibitors

  摘要：

  A series of unsymmetrically substituted biphenyl compounds was designed as alpha helical proteomimetics with the aim of inhibiting the binding of coactivator proteins to the nuclear hormone receptor coactivator binding domain. These compounds were synthesized in good overall yields in seven steps starting from 2-bromoanisole. The final products were evaluated using cotransfection reporter gene assays and mammalian two-hybrid competitive inhibition assays to demonstrate their effectiveness as competitive binding inhibitors. The results from this study indicate that these proteomimetics possess the ability to inhibit coactivator-receptor interactions, but via a mixed mode of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.051

文献信息

• Metal-Free C–O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
  作者：Luis Bering、Kirujan Jeyakumar、Andrey P. Antonchick

  DOI：10.1021/acs.orglett.8b01495

  日期：2018.7.6

  conditions enabled a catalytic and metal-free Friedel–Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel–Crafts reaction.

  描述了使用硝鎓盐作为催化剂的苄基苯基醚的无金属催化的分子内重排。优化的反应条件使苄基醇能够进行无金属催化的Friedel-Crafts烷基化反应，从而产生水作为化学计量副产物。展示了方法和在药物合成中的应用的综合范围（> 50个示例）。机理研究表明，路易斯酸基机理可用于无金属的Friedel-Crafts反应。
• 10.1039/d4cy00429a
  作者：Biswas, Subir、Barman, Dipankar、Dutta, Priyanka、Gour, Nand K.、Lee, Seonghwan、Kim, Donguk、Park, Young-Bin、Bora, Tonmoy J.、Devi, Arpita、Khanam, Salma A.、Saikia, Lakshi、Karunakar, Galla V.、Zaki, Magdi E. A.、Bania, Kusum K.

  DOI：10.1039/d4cy00429a

  日期：——

  of naphthols proceeded very well at room temperature. Density functional theory (DFT) calculation on the stability of benzyl carbocation and the reaction mechanism clearly highlighted the role of the supported catalyst and its impact on the catalytic reaction. Fee radical trapping experiment supported by mass spectroscopy analysis suggested the involvement of 2-naphthyloxy radicals in selective [1,1′-binaphthalene]-2

  苯酚与伯芳香醇的苄基化以及萘酚与过氧化氢 (H 2 O 2 ) 的氧化 C-C 偶联生成联芳基衍生物长期以来一直给有机化学家带来挑战。目前的工作使用负载在沸石-NaY 基质上的钌 (Ru) 基催化剂解决了与这些反应相关的局限性。对三种不同类型的钌催化剂的详细研究提供了这样的信息：用高价钌物质产生强路易斯酸位点，在苯酚的苄基化反应中具有高产率和高邻位选择性。然而，低价Ru(0)物种的存在对催化过程产生负面影响。在 H 2 O 2存在下，2-萘酚的氧化 C-C 偶联反应快速进行，仅产生产物 BINOL。使用相同的 Ru 催化剂，苯酚的苄基化反应在 100 °C 下发生，而萘酚的 C-C 偶联在室温下进行得很好。对苄基碳正离子稳定性和反应机理的密度泛函理论（DFT）计算清楚地突出了负载型催化剂的作用及其对催化反应的影响。质谱分析支持的自由基捕获实验表明，2-萘氧基自由基参与了选择性[1,1'-联萘]-2
• 4,4′-Unsymmetrically substituted 3,3′-biphenyl alpha helical proteomimetics as potential coactivator binding inhibitors
  作者：Patrick T. Weiser、Ching-Yi Chang、Donald P. McDonnell、Robert N. Hanson

  DOI：10.1016/j.bmc.2013.10.051

  日期：2014.1

  A series of unsymmetrically substituted biphenyl compounds was designed as alpha helical proteomimetics with the aim of inhibiting the binding of coactivator proteins to the nuclear hormone receptor coactivator binding domain. These compounds were synthesized in good overall yields in seven steps starting from 2-bromoanisole. The final products were evaluated using cotransfection reporter gene assays and mammalian two-hybrid competitive inhibition assays to demonstrate their effectiveness as competitive binding inhibitors. The results from this study indicate that these proteomimetics possess the ability to inhibit coactivator-receptor interactions, but via a mixed mode of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.