1,2,4,5-四氟-3-甲氧基-6-(2-苯基乙炔基)苯 | 132162-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,2,4,5-四氟-3-甲氧基-6-(2-苯基乙炔基)苯
• 英文名称: 1-(4-Methoxy-2,3,5,6-tetrafluorophenyl)-2-phenylethyne
• 英文别名: 1,2,4,5-tetrafluoro-3-methoxy-6-(2-phenylethynyl)benzene；Benzene, 1,2,4,5-tetrafluoro-3-methoxy-6-(phenylethynyl)-
• CAS: 132162-70-0
• 化学式: C₁₅H₈F₄O
• 分子量: 280.222
• InChiKey: SBNRIEUJQHRPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 1-pentafluorophenyl-2-phenylacetylene 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 以87%的产率得到1,2,4,5-四氟-3-甲氧基-6-(2-苯基乙炔基)苯
  参考文献：
  名称：

  Arene-perfluoroarene interactions in crystal engineering: structural preferences in polyfluorinated tolans

  摘要：

  The compounds 4-ROC6F4C=CPh ( 4) where R = Me ( a), Et ( b), Pr-n ( c), Pr-i ( d), Bu-n ( e), n-C5H11 (f), PhCH2 (g), PhCH2CH2 (h), 4-MeC6H4 (i), 4-EtC6H4 (j) and menthyl (k), have been prepared by reaction of C6F5C=CPh (3) with ROH in the presence of KOH, and characterised by NMR (H-1, C-13, F-19) and mass spectroscopy. The single-crystal structures of PhC=CPh.C(6)F5C=CC6F5 (1: 2), 3 and 4a, c, d, f, g, i have been determined by X-ray diffraction at 120 - 160 K, and that of 3 also calculated by an ab initio pseudo-potential DFT method. The tolan moiety is nearly planar in each molecule except 4a, which has a Ph/C6F5 dihedral angle of 25.8degrees. The R group adopts an out-of-plane orientation except in 4f, where the n-pentyl chain is nearly coplanar with the C6F5 group at the cost of severe distortion of the C(ar) - C(ar)-O angles ( which differ by 13.5degrees). The structures of 1: 2, 3 (pseudo-isomorphous with 1: 2), 4a, 4g ( disordered) and 4i contain stacks of alternating arene and perfluoroarene moieties; 4c and 4d form discrete centrosymmetric dimers with arene/ perfluoroarene overlap, while 4f forms infinite stacks without such overlap. Differential thermal analysis and transmitted polarised light microscopy revealed no liquid-crystalline behaviour of 3 and 4.

  DOI：

  10.1039/b314094f

文献信息

• Palladium/Cuprous Iodide Catalyzed Coupling of Substituted Tetrafluorophenyl Halides With 1-Alkynes
  作者：Ba V. Nguyen、Zhen-yu Yang、Donald J. Burton

  DOI：10.1016/s0022-1139(00)80502-3

  日期：1990.11

  In the presence of cuprous iodide, the palladium catalyzed coupling reaction of substituted tetrafluorophenyl halides with 1- alkynes gives the corresponding fluoroaryl alkynes in good to excellent yields under mild conditions. Both 4-substituted (methoxy, N,N-dimethylamino, morpholino) tetrafluorophenyl iodides and bromides work well, and alkyl, trimethylsilyl, phenyl, hydroxy, and ether functionalities

  在碘化亚铜的存在下，取代的四氟苯基卤化物与1-炔烃的钯催化偶联反应在温和条件下以良好或优异的收率得到相应的氟芳基炔烃。4-取代的（甲氧基，N，N-二甲基氨基，吗啉代）四氟苯基碘和溴离子均能很好地起作用，并且在反应条件下，炔烃部分中的烷基，三甲基甲硅烷基，苯基，羟基和醚官能团是可容忍的。该方法提供了取代的氟化芳基炔烃的实用合成。
• Wei, Ye; Zhao, Huaiqing; Kan, Jian, Journal of the American Chemical Society, 2010, vol. 132, p. 2522 - 2523
  作者：Wei, Ye、Zhao, Huaiqing、Kan, Jian、Su, Weiping、Hong, Maochun

  DOI：——

  日期：——
• General method for the preparation of functionalized fluorinated phenyl alkynes
  作者：Ba V. Nguyen、Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00078a013

  日期：1993.12

  In the presence of cuprous iodide, the palladium-catalyzed coupling reaction of 4-substituted tetrafluorophenyl iodides 1 with terminal alkynes proceeds readily in diisopropylamine or triethylamine to afford the corresponding fluorinated phenylalkynes in excellent yields under mild conditions. A variety of substituents on F-benzenes such as methoxy, dimethylamino, hydro, acyl, piperidino, and morpholino do not interfere with the coupling reaction. The reaction works well with 1-alkynes containing functional groups, including alkyl, alkenyl, phenyl, vinyl ether, alkoxy, phenoxy, hydroxy, amino, trimethylsilyl, and cyano, to give the corresponding (fluorophenyl)alkynes. With dialkynes, 2 equiv of the fluorinated phenyl iodide give bis(fluorophenyl)dialkynes in good yields. When 1,4-dibromotetrafluorobenzene reacts with an excess of alkyne in diisopropylamine, the bis-alkynylated tetrafluorobenzenes are obtained in good yields. However, in triethylamine the reaction gives a mixture of mono- and bis-alkynylated products. This method provides a practical approach to fluorinated phenyl functionalized alkynes.
• Arene-perfluoroarene interactions in crystal engineering: structural preferences in polyfluorinated tolans
  作者：Caroline E. Smith、Philip S. Smith、Rhodri Ll. Thomas、Edward G. Robins、Jonathan C. Collings、Chaoyang Dai、Andrew J. Scott、Simon Borwick、Andrei S. Batsanov、Stephen W. Watt、Stewart J. Clark、Christopher Viney、Judith A. K. Howard、William Clegg、Todd B. Marder

  DOI：10.1039/b314094f

  日期：——

  The compounds 4-ROC6F4C=CPh ( 4) where R = Me ( a), Et ( b), Pr-n ( c), Pr-i ( d), Bu-n ( e), n-C5H11 (f), PhCH2 (g), PhCH2CH2 (h), 4-MeC6H4 (i), 4-EtC6H4 (j) and menthyl (k), have been prepared by reaction of C6F5C=CPh (3) with ROH in the presence of KOH, and characterised by NMR (H-1, C-13, F-19) and mass spectroscopy. The single-crystal structures of PhC=CPh.C(6)F5C=CC6F5 (1: 2), 3 and 4a, c, d, f, g, i have been determined by X-ray diffraction at 120 - 160 K, and that of 3 also calculated by an ab initio pseudo-potential DFT method. The tolan moiety is nearly planar in each molecule except 4a, which has a Ph/C6F5 dihedral angle of 25.8degrees. The R group adopts an out-of-plane orientation except in 4f, where the n-pentyl chain is nearly coplanar with the C6F5 group at the cost of severe distortion of the C(ar) - C(ar)-O angles ( which differ by 13.5degrees). The structures of 1: 2, 3 (pseudo-isomorphous with 1: 2), 4a, 4g ( disordered) and 4i contain stacks of alternating arene and perfluoroarene moieties; 4c and 4d form discrete centrosymmetric dimers with arene/ perfluoroarene overlap, while 4f forms infinite stacks without such overlap. Differential thermal analysis and transmitted polarised light microscopy revealed no liquid-crystalline behaviour of 3 and 4.