4'-methoxy-5-methyl-[1,1'-biphenyl]-2-carbonitrile | 1620195-71-2

• 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: 4'-methoxy-5-methyl-[1,1'-biphenyl]-2-carbonitrile
• 英文别名: 2-(4-Methoxyphenyl)-4-methylbenzonitrile；2-(4-methoxyphenyl)-4-methylbenzonitrile
• CAS: 1620195-71-2
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: BPYBZYOOCCLCHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  环己烷 、 4'-methoxy-5-methyl-[1,1'-biphenyl]-2-carbonitrile 在 copper (II)-fluoride 、 过氧化二异丙苯 作用下， 反应 7.0h， 以71%的产率得到2-methyl-6-cyclohexyl-8-methoxyphenanthridine
  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-甲氧基苯硼酸 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 4'-methoxy-5-methyl-[1,1'-biphenyl]-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

• Direct Synthesis of Biphenyl-2-carbonitriles by Rh(III)-Catalyzed C–H Hiyama Cross-Coupling in Water
  作者：Xiuqi Zhang、Fukuan Zhang、Xiaolan Li、Ming-Zhu Lu、Xin Meng、Lei Huang、Haiqing Luo

  DOI：10.1021/acs.orglett.2c01754

  日期：2022.7.22

  This method represents an efficient rhodium(III)-catalyzed o-C–H arylation of readily available benzimidate derivatives with diverse arylsilanes in water as a sustainable solvent, enabling the straightforward synthesis of potentially useful biphenyl-2-carbonitrile derivatives. This silicon-based protocol employs benzimidates as both an efficacious directing group and the source of a nitrile group.

  该方法代表了一种有效的铑 (III) 催化的o -C-H 芳基化现成的苯甲亚胺衍生物与各种芳基硅烷在水中作为可持续溶剂，从而能够直接合成潜在有用的联苯-2-腈衍生物。这种基于硅的协议采用苯并亚胺作为有效的导向基团和腈基团的来源。
• 一种联苯-2-腈类化合物及其制备方法
  申请人：赣南师范大学

  公开号：CN114560790A

  公开（公告）日：2022-05-31

  本发明提供一种联苯‑2‑腈类化合物及其制备方法，属于有机合成技术领域。本发明提供的联苯‑2‑腈类化合物的制备方法以环境友好的芳基硅试剂为芳基源在铑催化对芳基亚胺酯直接C‑H邻位芳基化反应和脱醇反应来合成联苯‑2‑腈类化合物。特别值得一提的是，该反应以H2O做为溶剂时转化反应性好，底物范围广，在温和的条件下对带有各种官能团的反应底物都具有良好的耐受性。这种该类化合物同时含联苯和氰基两种重要的核心有用骨架，对于活性药物分子和功能材料的研发具有重要价值。
• Novel Vanilloid Receptor Ligands and Use Thereof for the Production of Pharmaceutical Preparations
  申请人：Gruenenthal GmbH

  公开号：US20140179686A1

  公开（公告）日：2014-06-26

  The present invention relates to novel vanilloid receptor ligands, to a process for the production thereof, to pharmaceutical preparations containing these compounds and to the use of these compounds for the production of pharmaceutical preparations.
• A Free Radical Cascade Cyclization of Isocyanides with Simple Alkanes and Alcohols
  作者：Zejiang Li、Fenghua Fan、Jie Yang、Zhong-Quan Liu

  DOI：10.1021/ol501461u

  日期：2014.6.20

  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.
• Controllable Rh(III)-Catalyzed C–H Arylation and Dealcoholization: Access to Biphenyl-2-carbonitriles and Biphenyl-2-carbimidates
  作者：Bo Jiang、Songxiao Wu、Jing Zeng、Xiaobo Yang

  DOI：10.1021/acs.orglett.8b02915

  日期：2018.10.19

  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.