2'-fluoro-[1,1'-biphenyl]-2-carbonitrile | 400820-15-7

• 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: 2'-fluoro-[1,1'-biphenyl]-2-carbonitrile
• 英文别名: 2-(2-Fluorophenyl)benzonitrile
• CAS: 400820-15-7
• 化学式: C₁₃H₈FN
• 分子量: 197.212
• InChiKey: XFQKBLLWMIEWET-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  338.3±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2'-fluoro-[1,1'-biphenyl]-2-carbonitrile 在 双(乙腈)氯化钯(II) 、 水 、 silver trifluoroacetate 作用下， 以 N,N-二甲基乙酰胺 、 三氟乙酸 为溶剂， 反应 72.0h， 以46%的产率得到4-氟-9H-芴-9-酮
  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'-fluoro-[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

文献信息

• Continuous-Flow Synthesis of Biaryls by Negishi Cross-Coupling of Fluoro- and Trifluoromethyl-Substituted (Hetero)arenes
  作者：Stefan Roesner、Stephen L. Buchwald

  DOI：10.1002/anie.201605584

  日期：2016.8.22

  continuous‐flow method for the regioselective arylation of fluoroarenes and fluoropyridines has been developed. The telescoped procedure reported here consists of a three‐step metalation, zincation, and Negishi cross‐coupling sequence, providing efficient access to a variety of functionalized 2‐fluorobiaryl products. Precise temperature control of the metalation step, made possible by continuous‐flow technology

  已经开发出一种连续流方法，用于氟代芳烃和氟吡啶的区域选择性芳基化。此处报道的伸缩程序包括三个步骤的金属化，镀锌和Negishi交叉耦合序列，可有效访问各种功能化的2-氟联芳基产品。连续流技术可以实现对金属化步骤的精确温度控制，从而可以高产率，短停留时间高效制备芳基化产物。另外，还提供了苯并三氟化物衍生物的区域选择性芳基化的几个实例。
• Convergent Synthesis of 6-Substituted Phenanthridines via Anionic Ring Closure
  作者：Morten Lysén、Jesper L. Kristensen、Per Vedsø、Mikael Begtrup

  DOI：10.1021/ol0170051

  日期：2002.1.1

  [reaction: see text] The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 degrees C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature

  [反应：见正文]将有机金属衍生物加到2-（2-氟苯基）苄腈的氰基上，然后进行分子内亲核取代，生成6-取代的菲啶。烷基锂，芳基锂和空间上不需要的锂酰胺在-78℃下反应，在升温至室温时以82-98％的产率产生6-取代的菲啶。相应的格氏试剂的添加需要过量的有机金属试剂并在高温下延长反应时间。
• [EN] IMIDAZO-TRIAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-TRIAZINE COMME LIGANDS DE RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2002038568A1

  公开（公告）日：2002-05-16

  A class of 7-phenylimidazo [1,2-b][1,2,4]triazine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a -NH- linkage, being selective ligands for GABAA receptors, in particular having good affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类7-苯基咪唑[1,2-b][1,2,4]三嗪衍生物，取代苯环的间位上，由一个可选择取代的芳基或杂环芳基基团直接连接或通过氧原子或-NH-键桥接，是选择性的GABAA受体配体，特别是对其α2和/或α3和/或α5亚单位具有良好的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、惊厥和认知障碍是有益的。
• [EN] IMIDAZO-PYRIMIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-PYRIMIDINE UTILISES COMME LIGANDS POUR LES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2002074772A1

  公开（公告）日：2002-09-26

  A class of 3-phenylimidazo[1,2-a]pyrimidine derivatives, substituted at the meta position of the phenyl ring by a directly attached, optionally halo- and/or cyano-substituted aryl or heteroaryl group, and further substituted on the phenyl ring by one or two fluorine atoms, are selective ligands for GABAA receptors, in particular having good affinity for the α2 and/or α3 and/or α5 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类3-苯基咪唑[1,2-a]嘧啶衍生物，取代苯环的间位，直接连接一个可选择的卤素和/或氰基取代的芳基或杂环基团，并在苯环上进一步取代一个或两个氟原子，是选择性的GABAA受体配体，特别是对其α2和/或α3和/或α5亚单位具有良好的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、惊厥和认知障碍具有益处。
• [EN] IMIDAZO-PYRIMIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES D'IMIDAZO-PYRIMIDINE COMME LIGANDS POUR LES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2002074773A1

  公开（公告）日：2002-09-26

  A class of 3-phenylimidazo[1,2-a]pyrimidine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a -NH- linkage, and further substituted on the phenyl ring by alkyl, trifluoromethyl, alkoxy or one or two halogen atoms, especially fluoro, are selective ligands for GABAA receptors, in particular having good affinity for the a2 and/or a3 and/or a5 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类3-苯基咪唑并[1,2-a]嘧啶衍生物，苯环的间位被取代为可选择取代的芳基或杂环基，该基团直接连接或通过氧原子或-NH-键桥接，并且苯环上进一步取代为烷基，三氟甲基，烷氧基或一个或两个卤素原子，特别是氟原子。这些化合物是GABAA受体的选择性配体，特别是对其中的a2和/或a3和/或a5亚基具有良好的亲和力，因此有助于治疗和/或预防中枢神经系统的不良症状，包括焦虑，抽搐和认知障碍。