4,4''-bis(trifluoromethyl)-1,1':4',1''-terphenyl | 72872-93-6

• 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: 4,4''-bis(trifluoromethyl)-1,1':4',1''-terphenyl
• 英文别名: 4,4''-Bis(trifluoromethyl)-1,1':4',1''-terbenzene；1,4-bis[4-(trifluoromethyl)phenyl]benzene
• CAS: 72872-93-6
• 化学式: C₂₀H₁₂F₆
• 分子量: 366.306
• InChiKey: GGKYRLJHBYZIOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-二溴苯 、 4-三氟甲基苯硼酸 在 sodium tetrachloropalladate(II) 、 C₂₂H₁₆O₈S₂^(2-)*2Na⁽¹⁺⁾ 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以90%的产率得到4,4''-bis(trifluoromethyl)-1,1':4',1''-terphenyl
  参考文献：
  名称：

  2N2O-Salen作为配体在钯催化的二溴苯的Suzuki-Miyaura钯催化下合成三联苯衍生物

  摘要：

  通过使用2N2O-salen作为H 2 O / EtOH（V：V = 4：1）中的配体，开发了一种简单高效的Na 2 PdCl 4催化二溴苯和芳基硼酸的Suzuki-Miyaura反应的催化系统。℃。使用该方法，含有空间上要求的邻位取代基（例如二溴苯和/或芳基硼酸）的底物的反应有效地进行，相应的三联苯衍生物以中等至极好的收率生产。此外，该方法为三联苯化合物的克级合成提供了有趣的功能。

  DOI：

  10.1002/cjoc.201500446

文献信息

• Synthesis of symmetrical terphenyl derivatives by PdCl₂-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand
  作者：Ningning Gu、Yashuai Liu、Ping Liu、Xiaowei Ma、Yan Liu

  DOI：10.1080/00397911.2015.1126606

  日期：2016.1.17

  ABSTRACT A simple and efficient catalytic system for PdCl2 catalyzing the Suzuki–Miyaura reaction of dibromobenzene and arylboronic acid has been developed by using 3-(diphenylphosphino)propanoic acid as a ligand in dimethylsulfoxide at 100 °C. Using this method, a series of symmetrical terphenyl derivatives were obtained with remarkably good yields, up to 93%. GRAPHICAL ABSTRACT

  摘要 利用 3-（二苯基膦基）丙酸作为二甲基亚砜中的配体，在 100 °C 下开发了一种简单有效的 PdCl2 催化体系，用于催化二溴苯和芳基硼酸的 Suzuki-Miyaura 反应。使用这种方法，以非常好的收率获得了一系列对称的三联苯衍生物，高达 93%。图形概要
• Water-Soluble Palladium Nanoparticles: Click Synthesis and Applications as a Recyclable Catalyst in Suzuki Cross-Couplings in Aqueous Media
  作者：Nereida Mejías、Roser Pleixats、Alexandr Shafir、Mercedes Medio-Simón、Gregorio Asensio

  DOI：10.1002/ejoc.201000671

  日期：2010.9

  prepared by a threefold copper-catalyzed [3+2] cycloaddition (click chemistry), was found to act as an efficient stabilizer for palladium nanoparticles. The newly formed material proved to be active as a recyclable catalyst in Suzuki coupling; the presence of polyether chains allowed for the catalytic runs to be conducted in aqueous media.

  通过三重铜催化的 [3+2] 环加成（点击化学）制备的新 PEG 标记材料被发现可作为钯纳米颗粒的有效稳定剂。新形成的材料被证明在 Suzuki 偶联中作为可回收催化剂具有活性；聚醚链的存在允许催化运行在水性介质中进行。
• Structural tailoring of p-terphenyl scaffold: Towards advanced plastic scintillator
  作者：Michaela Fecková、Martina Vachtlová、Jan Podlesný、Zuzana Burešová、Oldřich Pytela、Milan Klikar、Jiří Janda、Hana Burešová、Radek Pjatkan、Filip Bureš

  DOI：10.1016/j.dyepig.2023.111593

  日期：2023.11

  oxidation of the parent p-terphenyl π-system affected by the electronic and steric effects of the substituents were recorded by cyclic voltammetry. When compared to parent p-terphenyl, a narrowed HOMO–LUMO gap has been measured/calculated for most of the prepared derivatives. The absorption and emission maxima ranged from 286 to 293 and 341–360 nm, respectively. The latter is affected by the substitution

  使用简便的合成方法（Suzuki-Miyaura 和 Friedel-Crafts 反应）设计并制备了一系列全面的十五种对三联苯衍生物。各种烷基、烷氧基或三氟甲基已连接到对三联苯上以获得对称和不对称衍生物。对称性破缺可以提高单取代衍生物的溶解度。热分析揭示了几种晶相的可逆形成和非常高的热稳定性。通过循环伏安法记录受取代基的电子和空间效应影响的母体对三联苯π-系统的还原和氧化。与父p相比-三联苯，已对大多数制备的衍生物测量/计算了狭窄的 HOMO-LUMO 能隙。吸收和发射最大值范围分别为 286 至 293 和 341-360 nm。后者受取代的影响更为显着，荧光量子产率在0.52~0.75范围内。测量到高达 6400 cm -1 的斯托克斯位移，表明激发时发生大的结构重排（平面化）。PTP衍生物进一步用作闪烁的初级和次级发光体。4-甲基-p事实证明，-三联苯是一种合成简单、分离容易、溶解
• Synthesis of Biaryls and Polyaryls by Ligand-Free Suzuki Reaction in Aqueous Phase
  作者：Leifang Liu、Yuhong Zhang、Bingwei Xin

  DOI：10.1021/jo060122v

  日期：2006.5.1

  A highly efficient palladium acetate-catalyzed ligand-free Suzuki reaction in aqueous phase was developed in short reaction times (0.5-1 h) at 35 degrees C in air. The key for such a successful catalytic system was the use of a suitable amount of cosolvents in the aqueous phase. The method could be extended to the consecutive multi-Suzuki coupling, and polyaryls were prepared in a single one-pot step in high selectivity and excellent yield under mild reaction conditions (60 degrees C).
• Pd−P(<i>t</i>-Bu)₃-Catalyzed Consecutive Cross-Coupling of <i>p</i>-Phenylenedizinc Compound with Two Different Electrophiles Leading to Unsymmetrically 1,4-Disubstituted Benzenes
  作者：Takahiro Kawamoto、Shogo Ejiri、Kana Kobayashi、Shunsuke Odo、Yasushi Nishihara、Kentaro Takagi

  DOI：10.1021/jo702103r

  日期：2008.2.1

  [GRAPHICS]Pd-P(t-BU)(3) was found to be a chemoselective catalyst for the reaction of p-phenylenedizinc compound with equimolar amounts of carbon electrophiles to afford the single cross-coupling products in good yields, effectively suppressing the formation of double cross-coupling products. The subsequent additions of other electrophiles to the resulting solutions caused the second cross-coupling of the incipient products to take place, achieving a novel and efficient one-pot synthesis of unsymmetrically 1,4-disubstituted benzenes. The origin of the observed high chemoselectivity was speculated.