5-methyl-4'-chlorobiphenyl-2-carbonitrile | 1268823-49-9

• 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-methyl-4'-chlorobiphenyl-2-carbonitrile
• 英文别名: 4'-chloro-5-methyl-[1,1'-biphenyl]-2-carbonitrile
• CAS: 1268823-49-9
• 化学式: C₁₄H₁₀ClN
• 分子量: 227.693
• InChiKey: ZOEOBNBRVVFJST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  环己烷 、 5-methyl-4'-chlorobiphenyl-2-carbonitrile 在 copper (II)-fluoride 、 过氧化二异丙苯 作用下， 反应 7.0h， 以62%的产率得到8-chloro-6-cyclohexyl-2-methylphenanthridine
  参考文献：
  名称：

  A Free Radical Cascade Cyclization of Isocyanides with Simple Alkanes and Alcohols

  摘要：

  A copper-catalyzed free-radical cascade cyclization of isocyanides with simple alkanes and alcohols was developed, which allowed convenient access to various alkyl-substituted phenanthridines.

  DOI：

  10.1021/ol501461u
• 作为产物：
  描述：

  4-氯苯硼酸 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver fluoride 、 特戊酸钠 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 5.0h， 生成 5-methyl-4'-chlorobiphenyl-2-carbonitrile
  参考文献：
  名称：

  Controllable Rh(III)-Catalyzed C–H Arylation and Dealcoholization: Access to Biphenyl-2-carbonitriles and Biphenyl-2-carbimidates

  摘要：

  A controllable Rh(III)-catalyzed C-H arylation and dealcoholization of benzimidates with arylboronic esters was developed, delivering various biphenyl-2-carbonitriles and biphenyl-2-carbimidates by simply tuning the reaction conditions. This approach features high efficiency, good functional group tolerance, and easy operation. It also provides an alternative pathway to thoroughly exploit the directing group in transition-metal-catalyzed C-H activations.

  DOI：

  10.1021/acs.orglett.8b02915

文献信息

• 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.