2'-bromo-[1,1'-biphenyl]-2-carbonitrile | 54245-41-9

• 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: 2'-bromo-[1,1'-biphenyl]-2-carbonitrile
• 英文别名: 2'-Bromobiphenyl-2-carbonitrile；2-(2-bromophenyl)benzonitrile
• CAS: 54245-41-9
• 化学式: C₁₃H₈BrN
• 分子量: 258.117
• InChiKey: KIXWTAUFOWRZOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2'-bromo-[1,1'-biphenyl]-2-carbonitrile 在 硫酸 作用下， 生成 2-(2-溴苯基)苯甲酸
  参考文献：
  名称：

  Cirigottis,K.A. et al., Australian Journal of Chemistry, 1974, vol. 27, p. 2209 - 2228

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基苯硼酸 在 tripotassium phosphate "n" hydrate 、 Pd(PPh₃)₂Cl₂ 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 2'-bromo-[1,1'-biphenyl]-2-carbonitrile
  参考文献：
  名称：

  Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

  摘要：

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

  DOI：

  10.1021/ol401063w
• 作为试剂：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 乙基溴化镁 在 copper(I) oxide 、 2'-bromo-[1,1'-biphenyl]-2-carbonitrile 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 24.0h， 以63%的产率得到1-ethoxy-2,2,6,6-tetramethylpiperadine
  参考文献：
  名称：

  Synthesis of Polysubstituted Phenanthridines via Ligand-Free Copper-Catalyzed Annulation

  摘要：

  A novel procedure for the cascade reaction of the addition of a Grignard reagent to a nitrile with a copper-catalyzed C-N bond coupling was developed, which afforded various polysubstituted phenanthridines in moderate to good yields with tolerance for a wide variety of substrates. Experimental data demonstrated that the reaction proceeded more likely through a Cu(I/III) catalytic cycle.

  DOI：

  10.1021/ol502237a

文献信息

• Copper-catalyzed intramolecular C–N coupling reaction of aryl halide with amide
  作者：Wei-Lin Chen、Yuan-Ye Jhang、Jen-Chieh Hsieh

  DOI：10.1007/s11164-016-2438-6

  日期：2017.6

  An efficient and concise method for the ligand-free copper-catalyzed intramolecular C–N bond coupling was developed, which afforded various (NH)-phenanthridinones in good to excellent yields with tolerance of various substrates.

  开发了一种高效，简捷的无配体铜催化的分子内C–N键偶联方法，该方法以良好的收率和优异的收率提供了各种（NH）-菲啶酮类化合物，并能耐受各种底物。
• 一种4-溴芴酮的生产方法
  申请人：河南省科学院化学研究所有限公司

  公开号：CN105237379B

  公开（公告）日：2017-03-22

  本发明公开了一种4‑溴芴酮的生产方法，属有机化学合成领域。通过如下方法实现：氩气保护下，以苯甲腈为原料，在钯催化剂、铜催化剂与有机膦配体作用下与邻二溴苯反应得到2‑溴‑2’‑甲腈基联苯，然后经水解、闭环合成产物4‑溴芴酮，反应过程操作简单，生产成本低，适合工业化生产。4‑溴芴酮可用于有机光电材料、医药农药等领域。
• Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-<i>H</i>-Phenanthridines via a Transition-Metal-Free Process
  作者：Wei-Lin Chen、Chun-Yuan Chen、Yan-Fu Chen、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.5b00544

  日期：2015.3.20

  A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.
• CARBAZOLE-BASED COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20160126474A1

  公开（公告）日：2016-05-05

  A carbazole compound represented by Formula 1: wherein in Formula 1, groups X 1 to X 8 , X 11 to X 19 , and R 41 to R 43 are the same as in the specification.
• Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation
  作者：Jung-Chih Wan、Jun-Min Huang、Yu-Huei Jhan、Jen-Chieh Hsieh

  DOI：10.1021/ol401063w

  日期：2013.6.7

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.