1-Benzyloxy-2,3,5,6-tetrafluoro-4-phenylethynyl-benzene | 7230-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Benzyloxy-2,3,5,6-tetrafluoro-4-phenylethynyl-benzene
• 英文别名: 1,2,4,5-Tetrafluoro-3-(2-phenylethynyl)-6-phenylmethoxybenzene
• CAS: 7230-45-7
• 化学式: C₂₁H₁₂F₄O
• 分子量: 356.319
• InChiKey: KPIKUSQEFIOHJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  1-pentafluorophenyl-2-phenylacetylene 、 苯甲醇 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 生成 1-Benzyloxy-2,3,5,6-tetrafluoro-4-phenylethynyl-benzene
  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

• 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.