5-methoxy-1,1'-biphenyl-2-carbonitrile | 500309-63-7

• 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-methoxy-1,1'-biphenyl-2-carbonitrile
• 英文别名: 5-methoxylbiphenyl-2-carbonitrile；5-methoxybiphenyl-2-carbonitrile；4-methoxy-4-phenyl-benzonitrile；5-methoxy-biphenyl-2-carbonitrile；5-Methoxy-biphenyl-2-carbonitril；4-Methoxy-2-phenyl-benzoesaeurenitril；4-Methoxy-2-phenylbenzonitrile
• CAS: 500309-63-7
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: ONSUJXJOSYUILA-UHFFFAOYSA-N

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-methoxy-1,1'-biphenyl-2-carbonitrile 在 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 生成 5-methoxy-[1,1′-biphenyl]-2-carboxylic acid
  参考文献：
  名称：

  半合成青霉素。I.2-联苯苄青霉素。

  摘要：

  DOI：

  10.1021/jm00333a001
• 作为产物：
  描述：

  2-phenyl-4-nitrobromobenzene 在 吡啶 、 甲醇 、 sodium methylate 、 copper(II) sulfate 作用下， 生成 5-methoxy-1,1'-biphenyl-2-carbonitrile
  参考文献：
  名称：

  Aromatic Cyclodehydration. XXVI.¹ 3-Hydroxy-9-(p-hydroxyphenyl)-10-ethylphenanthrene, an Estrogen Analog

  摘要：

  DOI：

  10.1021/ja01139a043

文献信息

• 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。
• Metal-Free Directed<i>ortho</i>C-H Iodination: Synthesis of 2′-Iodobiaryl-2-carbonitriles
  作者：Satinath Sarkar、Manoranjan Jana、Tadigoppula Narender

  DOI：10.1002/ejoc.201300584

  日期：2013.10

  developed. A series of 2′-iodobiaryl-2-carbonitriles were synthesized from substituted biphenylcarbonitriles and naphthylbenzonitriles in reasonably good yields by using bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4, Barluenga's reagent) and HBF4·OEt2. The biaryl-2-carbonitriles are useful precursors for the synthesis of benzocyclic ketones.

  开发了联芳基-2-腈的无金属定向邻位 C-H 碘化。使用双（吡啶）碘鎓（I）四氟硼酸盐（IPy2BF4，Barluenga 试剂）和 HBF4·OEt2，从取代的联苯甲腈和萘基苄腈合成了一系列 2'-碘联二芳基-2-甲腈，收率相当好。联芳基-2-腈是合成苯环酮的有用前体。
• Synthesis of Biphenyl-2-carbonitrile Derivatives via a Palladium-Catalyzed sp² C−H Bond Activation Using Cyano as a Directing Group
  作者：Wu Li、Zhipeng Xu、Peipei Sun、Xiaoqing Jiang、Min Fang

  DOI：10.1021/ol103075n

  日期：2011.3.18

  Pd-II-catalyzed aromatic C-H bond activation using cyano as a directing group was carried out in TFA medium. Biphenyl-2-carbonitrile derivatives were therefore synthesized from aryl nitriles and aryl halides in moderate to good yields.
• Synthesis and Fungistatic Activity of Some 3-Hydroxybiphenyl Derivatives
  作者：Charles K. Bradsher、Frances C. Brown、Hardin K. Porter

  DOI：10.1021/ja01638a021

  日期：1954.5