5-methoxybiphenyl-4-carbonitrile | 408339-01-5

• 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: 5-methoxybiphenyl-4-carbonitrile
• 英文别名: 3-methoxy-[1,1'-biphenyl]-4-carbonitrile；2-methoxy-4-phenylbenzonitrile；4-cyano-3-methoxybiphenyl；3-methoxy-biphenyl-4-carbonitrile
• CAS: 408339-01-5
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: DZVBZHBSBZRLES-UHFFFAOYSA-N

物化性质

• 熔点：
  86.5-87.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  374.5±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxybiphenyl-4-carbonitrile 在 三氯化铝 、 乙醚 作用下， 生成 1-(3-hydroxy-biphenyl-4-yl)-propan-1-one
  参考文献：
  名称：

  Synthesis and Fungistatic Activity of Some 3-Hydroxybiphenyl Derivatives

  摘要：

  DOI：

  10.1021/ja01638a021
• 作为产物：
  描述：

  4-溴-3-硝基联苯 在 CuCN 作用下， 生成 5-methoxybiphenyl-4-carbonitrile
  参考文献：
  名称：

  Synthesis and Fungistatic Activity of Some 3-Hydroxybiphenyl Derivatives

  摘要：

  DOI：

  10.1021/ja01638a021

文献信息

• Metal-Free Etherification of Aryl Methyl Ether Derivatives by C–OMe Bond Cleavage
  作者：Xueqiang Wang、Chenchen Li、Xia Wang、Qingli Wang、Xiu-Qin Dong、Abing Duan、Wanxiang Zhao

  DOI：10.1021/acs.orglett.8b01696

  日期：2018.7.20

  A general and efficient protocol was developed for the synthesis of aryl alkyl ethers through metal-free C–OMe bond cleavage under mild reaction conditions. This process displays a wide scope of methoxyarenes and alcohols, including primary, secondary, and tertiary alcohols, as well as natural products, pharmaceuticals, and biologically active alcohols. DFT calculations and experimental results simultaneously

  为在温和的反应条件下通过无金属的C-OMe键裂解合成芳基烷基醚，开发了一种通用而有效的方案。该方法显示出广泛的甲氧基芳烃和醇，包括伯，仲和叔醇，以及天然产物，药物和生物活性醇。DFT计算和实验结果同时证实，钾离子通过与腈的结合在甲氧基的活化中起关键作用，并为S N Ar机制提供了支持。
• The Hiyama Cross‐Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents
  作者：Shun Ichii、Go Hamasaka、Yasuhiro Uozumi

  DOI：10.1002/asia.201901155

  日期：2019.11.4

  A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS

  负载量为5 mol ppm的钯NNC-钳子络合物有效地催化了芳基溴化物与丙二醇中的芳基（三烷氧基）硅烷的Hiyama偶联反应，从而以优异的收率得到了相应的联芳基。该方法应用于阿达帕林和联芳基型液晶化合物的合成，以及右美沙芬和诺氟沙星的衍生化。反应混合物的ESI-MS和NMR分析表明原位形成五配位螺硅酸酯中间体。初步的理论研究表明，原位形成的乙二醇衍生的硅酸盐中间体在过渡金属化步骤中是反应性很强的硅试剂。
• Electrochemical C−H Cyanation of Electron-Rich (Hetero)Arenes
  作者：Davit Hayrapetyan、Raja K. Rit、Markus Kratz、Kristina Tschulik、Lukas J. Gooßen

  DOI：10.1002/chem.201802247

  日期：2018.8.6

  straightforward method for the electrochemical C−H cyanation of arenes and heteroarenes that proceeds at room temperature in MeOH, with NaCN as the reagent in a simple, open, undivided electrochemical cell is reported. The platinum electrodes are passivated by adsorbed cyanide, which allows conversion of an exceptionally broad range of electron‐rich substrates all the way down to dialkyl arenes. The cyanide electrolyte

  据报道，芳烃和杂芳烃的CH-H氰化的直接方法是在室温下于MeOH中进行，NaCN作为试剂在简单，开放，不分隔的电化学池中进行。铂电极被吸附的氰化物钝化，从而可以将范围广泛的富电子底物一直转化为二烷基芳烃。氰化物电解质可以补充HCN，为无盐工业CH氰化打开了机会。
• Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C–H bonds
  作者：Kazuhiro Okamoto、Masahito Watanabe、Masahito Murai、Ryo Hatano、Kouichi Ohe

  DOI：10.1039/c2cc18008a

  日期：——

  A gallium-catalysed, direct cyanation reaction of aromatic and heteroaromatic C-H bonds with cyanogen bromide was developed as a practical synthetic method for the preparation of aromatic nitriles.

  开发了一种镓催化的芳香族和杂芳香族CH键与溴化氰的直接氰化反应，作为制备芳香腈的一种实用合成方法。
• Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols
  作者：Shuai Li、Xia Wang、Xin-Ge Yang、Gui-Quan Yu、Xue-Qiang Wang

  DOI：10.1055/s-0037-1611898

  日期：2019.9

  A transition-metal-free etherification protocol that is capable of synthesizing deuterated ethers is described. A wide range of aryl alkyl ethers and thioethers were suitable for this transformation owing to the mild reaction conditions. Besides, a series of sterically bulky deuterated alcohols were successfully incorporated into cyano-substituted arenes. The results of mechanistic studies suggested

  描述了一种能够合成氘化醚的无过渡金属醚化协议。由于反应条件温和，各种芳基烷基醚和硫醚适用于这种转化。此外，一系列空间庞大的氘代醇成功地掺入氰基取代的芳烃中。机理研究结果表明该反应可能通过亲核芳香取代途径发生。