p-Phenyl-α,β,β-trifluorostyrene | 6999-04-8

• 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: p-Phenyl-α,β,β-trifluorostyrene
• 英文别名: 4-(1,2,2-trifluorovinyl)-1,1’-biphenyl；4-(1,2,2-trifluorovinyl)-1,1'-biphenyl；4-(1,2,2-trifluorovinyl)biphenyl；4-(trifluorovinyl)biphenyl；p-Phenyl-α,β,β-trifluorostyrol；4-(1,2,2-Trifluoroethenyl)biphenyl；1-phenyl-4-(1,2,2-trifluoroethenyl)benzene
• CAS: 6999-04-8
• 化学式: C₁₄H₉F₃
• 分子量: 234.221
• InChiKey: JKJZYWLFVNOLAF-UHFFFAOYSA-N

物化性质

• 沸点：
  120-130 °C(Press: 5 Torr)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(((2-methoxy-2-oxoethyl)imino)methyl)benzoate 、 p-Phenyl-α,β,β-trifluorostyrene 在 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 potassium tert-butylate 作用下， 反应 48.0h， 以78%的产率得到
  参考文献：
  名称：

  铜(I)催化偶氮甲碱叶立德不对称1,3-偶极环加成合成生物活性氟吡咯烷

  摘要：

  手性吡咯烷基单元是具有生物活性的天然产物和药物的重要组成部分，开发用于合成多种结构吡咯烷衍生物的有效方法具有重要意义。同时，由于氟原子特殊的物理化学性质，将含氟基团引入小分子中往往会在很大程度上改变其活性。在此，我们报道了一种通过 Cu( I ) 获得对映富集的 3,3-二氟和 3,3,4-三氟吡咯烷基衍生物的有效途径)-催化偶氮甲碱叶立德与活性较低的 1,1-二氟和 1,1,2-三氟苯乙烯的对映选择性 1,3-偶极环加成。一系列新型氟化吡咯烷以高产率（高达 96%）和优异的立体选择性（高达 >20:1 dr 和 97% ee）制备，这些独特的结构块可以很容易地引入一些天然化合物和药品。此外，对四种常见植物真菌的抗真菌活性研究表明，一些产品具有一般和高生物活性；与相应的非氟化化合物的低抗真菌活性相比，吡咯烷基环上的氟原子在抗真菌活性中起关键作用。

  DOI：

  10.1039/d1sc04595d
• 作为产物：
  描述：

  对苯基苯甲醛 在 triethylamine tris(hydrogen fluoride) 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 p-Phenyl-α,β,β-trifluorostyrene
  参考文献：
  名称：

  10.1002/ejoc.202400351

  摘要：

  We established a straightforward electrochemical dihalogenation (F, Cl, and Br) process for gem‐difluoroalkenes. This reaction exhibits a broad functional group tolerance and has been effectively utilized in the construction of complex molecules. The subsequent synthetic transformations of the products have highlighted the adaptable nature of the dihalogenated compounds, demonstrating their potential application in drug discovery and the investigation of innovative materials. The effective utilization of the dihalogenated product for 18F‐labeling represents a novel approach in generating highly potent 18F‐labeled tracers.

  DOI：

  10.1002/ejoc.202400351

文献信息

• Bromodifluoromethylation of aromatic Grignard reagents with CF2Br2
  作者：Masahiro Shiosaki、Munenori Inoue

  DOI：10.1016/j.tetlet.2014.10.082

  日期：2014.12

  The bromodifluoromethylation of aromatic Grignard reagents having electron-withdrawing groups with dibromodifluoromethane (CF2Br2) was developed. The reaction proceeded to give the corresponding (bromodifluoromethyl)benzene derivatives via a difluorocarbene-mediated mechanism.

  开发了具有吸电子基团的芳族格氏试剂与二溴二氟甲烷（CF 2 Br 2）的溴二氟甲基化。反应通过二氟卡宾介导的机理而得到相应的（溴二氟甲基）苯衍生物。
• Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides
  作者：Miriam O’Duill、Emmanuelle Dubost、Lukas Pfeifer、Véronique Gouverneur

  DOI：10.1021/acs.orglett.5b01510

  日期：2015.7.17

  The synthesis of arylCF(2)CF(2)SiMe(3) and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-aryl-ethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 degrees C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.
• Base-Free Hiyama Coupling Reaction via a Group 10 Metal Fluoride Intermediate Generated by C–F Bond Activation
  作者：Hiroki Saijo、Hironobu Sakaguchi、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1021/om5005513

  日期：2014.7.28

  A Pd(0)-catalyzed Hiyama coupling reaction of tetrafluoroethylene (TFE) proceeded without the use of a base to give alpha,beta,beta-trifluorostyrene derivatives. A Ni(0)-catalyzed Hiyama coupling reaction of perfluoroarenes also occurred without a base. The key intermediate in these reactions would be a transition-metal fluoride complex that is generated in situ by the oxidative addition of a C-F bond.
• A self-consistent and cross-checked scale of spin-delocalization substituent constants, the .sigma.JJ.bul. scale
  作者：Xikui Jiang、Guozhen Ji

  DOI：10.1021/jo00048a048

  日期：1992.10

  On the basis of the F-19 NMR data of substituted alpha,beta,beta-trifluorostyrenes and the rate constants of their thermal cycloaddition reactions, a self-consistent and cross-checked scale of spin-delocalization substituent constants sigma(JJ). is proposed for 21 para-substituents and for 10 meta-substituents. By means of adopting different rho(mb) values, three methods for the calculation of the sigma(JJ). values at five different temperatures and their averaged values are presented. It has been shown that at each temperature and within a range of rho(mb) values from -0.20 to -0.40 the same set of sigma. constants are obtained from these three methods. There are seven advantages to the sigma(JJ). approach, including the fact that the reaction is exceptionally clean, a tailor-made polar parameter sigma(mb) is used in the dual-parameter equation, and the validity of the approach is strongly supported by the meta substituent effect which is independent of the polar effect. Some radical reactions, EPR data of substituted benzyl radicals, and bond dissociation energies are reexamined by using the sigma(JJ). in conjunction with polar sigma constants in dual-parameter equations.
• Timofeyuk,G.V. et al., Doklady Chemistry, 1966, vol. 168, p. 541 - 542
  作者：Timofeyuk,G.V. et al.

  DOI：——

  日期：——