2-cyano-4"-methyl-p-terphenyl | 1433966-86-9

• 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-cyano-4"-methyl-p-terphenyl
• 英文别名: 2-[4-(4-Methylphenyl)phenyl]benzonitrile
• CAS: 1433966-86-9
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: BIVSODVFMRATHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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-cyano-4"-methyl-p-terphenyl 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81%的产率得到2-(p-tolyl)-9H-fluoren-9-one
  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-cyano-4"-methyl-p-terphenyl
  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

• Base-Controlled One-Pot Chemoselective Suzuki–Miyaura Reactions for the Synthesis of Unsymmetrical Terphenyls
  作者：Xinmin Li、Fangfang Feng、Changyue Ren、Yong Teng、Qinghong Hu、Zeli Yuan

  DOI：10.1055/s-0039-1690227

  日期：2019.12

  Suzuki–Miyaura reaction protocol of using bromophenyl fluorosulfonate as building block for the preparation of unsymmetrical terphenyls. The chemoselective cross-coupling of bromophenyl fluorosulfonate and arylboronic acids can be achieved by controlling base species without using any ligands. Under this methodology, various of m- and p-unsymmetrical terphenyls were obtained in moderate to good yields.

  我们报告了一种化学选择性 Suzuki-Miyaura 反应方案，该方案使用溴苯基氟磺酸盐作为制备不对称三联苯的基石。溴苯基氟磺酸盐和芳基硼酸的化学选择性交叉偶联可以通过控制碱基种类而不使用任何配体来实现。在这种方法下，以中等至良好的收率获得了各种间-和对-不对称三联苯。
• Temperature-controlled sequential Suzuki–Miyaura reactions for preparing unsymmetrical terphenyls
  作者：Xinmin Li、Chun Liu、Lei Wang、Qing Ye、Xin Jin、Zilin Jin

  DOI：10.1039/c8ob01661e

  日期：——

  A one-pot protocol of double Suzuki–Miyaura reactions has been developed for the synthesis of unsymmetrical terphenyls. In the absence of a ligand, potassium bromophenyltrifluoroborate reacts with arylboronic acid and then sequentially with a hetero/aryl bromide by controlling the reaction temperature, providing unsymmetrical p- and m-terphenyl compounds in moderate to good overall yields. This protocol

  已经开发了一种双铃木-宫浦双反应的一锅法方案，用于合成不对称的三联苯。在不存在配体，与芳基硼酸钾bromophenyltrifluoroborate发生反应，然后用通过控制反应温度，从而提供非对称的杂/芳基溴依次p -和米到良好的总产率-三联苯化合物在温和。该方案为无配位和好氧条件下的不对称三联苯提供了方便实用的方法。