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Synthesis and Mesomorphic Properties of Novel γ-Substituted β-Diketonates

Synthesis and Mesomorphic Properties of Novel γ-Substituted β-Diketonates
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摘要 The synthesis and mesomorphic properties of two series of novel -substituted -diketonates have been reported. All of the compounds 2,4-dioxo-3-pentyl 4-[[4-(n-alkoxyl) cinnamoyl]oxy]cinnamatetes Ia-If (n=7-12) exhibit two monotropic phases(N and Sc) and have a wider mesophase range than the compounds 2,4-dioxo-3-pentyl 4-[[4-(n-alkoxyl) benzoyl]oxy] cinnamatetes IIa-IIf (n=7-12), which display one monotropic nematic phase (n=7-10) or an enantiotropic nematic phase for n=11 or two enantiotropic phases (N and Sc) for n=12 .
作者 Jie HAN Liang Fu ZHANGWen WAN
机构地区 lDepartment of Chemistry Chengdu Institute of Organic Chemistry
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第2期155-158,共4页 中国化学快报（英文版）
分类号 O62 [理学—有机化学]
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参考文献10

  • 1[1]J. Bartulin, Z.X.Fan, W.Haase, Mol.Cryst.Liq.Cryst., 1992,220, 67.
  • 2[2]C.Cativiela, J.L.Serrano, M.M.Zurbano, J.Org.Chem., 1995,60,3074.
  • 3[3]S.T Trzaska, H .Zheng, T.M. Swager,Chem.Mater., 1999,11, 130.
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  • 7[7]Data for 2,4-Dioxo-3-pentyl 4-hydrocinnate 1. Yield 76.4%; white powder; 1H NMR (CDCl3, TMS) δppm: 14.45, 5.64 (2×s, 1H, CH), 7.70, 6.35 (2×d, 2H, J=16Hz, -CH=CH-), 7.40, 6.85 (2×d, 4H, J=8.0Hz, C6H4), 2.36, 2.05 (2×s, 6H, 2×CH3); IR (KBr) ν: 3366 (s,-OH), 1716 (s,ArC=O), 1631 (w, -CH=CH-), 1605, 1580, 1515 (s,Ar), 1266, 1204, 1149, 985 cm-1; MS (EI,70ev) m/z(%): 262 (M+,2.52), 147(100); Elemental analysis for C14H14O5: Calcd C, 64.12; H, 5.34; Found C, 63.88; H, 5.31.
  • 8[8]Data for 2,4-dioxo-3-pentyl 4-[[4-(n-decyloxy) cinnamoyl]oxy] cinnate Id. Yield 82%; White powder; 1H-NMR (CDCl3,TMS) δ ppm: 14.50, 5.62 (2×s, 1H, CH), 7.80, 6.54 (2×d, 2H, J=16Hz, -CH=CH-), 7.72, 6.46 (2×d, 2H,J=16Hz, -CH=CH-), 7.62, 7.23 (2×d, 4H, J=8Hz, Ar), 7.52, 6.91 (2×d, 4H, J=8Hz, Ar), 3.99 (t, 2H, J=6Hz, RCH2OAr), 2.34, 2.05 (2×s, 6H, 2×CH3), 1.78 (m, 2H, CH2), 1.24 (m, 14H, 7×CH2), 0.87 (t, 3H, J=6Hz, CH3); IR (KBr) ν: 1722 (s, ArC=O), 1631(w, C=C), 1600, 1506 (s, Ar), 1287, 252, 1216, 1146 cm-1 (s,Ar-O-C); MS (EI,70ev) m/z(%): 548 (M+, 0.27), 287(100); Elemental analysis for C33H40O7: Calcd C,72.26; H,7.30; Found C,72.31; H,7.42.
  • 9[9]Data for 2,4-dioxo-3-pentyl 4-[[4-(n-decyloxy) benzoyl] oxy]cinnate IId. Yield 68.5%; White powder; 1H NMR (CDCl3, TMS) δppm: 14.50, 5.66 (2×s, 1H, CH), 8.15, 7.30 (2×d, 4H, J=9Hz, Ar), 7.65, 6.99 (2×d, 4H, J=8.7Hz, Ar), 7.80, 6.58 (2×d, 2H, J=15.9Hz, -CH=CH-), 4.04 (t, 2H, J=6Hz, RCH2OAr), 2.37, 2.08 (2×s, 6H, 2×CH3), 1.85 (m, 2H, CH2), 1.30 (m, 14H, 7×CH2), 0.90 (t, 3H, J=6Hz, CH3); IR (KBr) ν:1727 (s, ArC=O), 1635 (w, C=C), 1603, 1510 (s, Ar), 1258, 1211, 1164 cm-1 (s, Ar-O-C); MS (EI,70ev) m/z (%): 522(M+, 0.93), 121 (100); Elemental analysis for C31H38O7: Calcd. C, 71.26; H, 7.28; Found C, 71.11; H, 7.38.
  • 10[10]D. Demus, L.Richer, Textures of liquid crystals, Verlag Chemie: Weinheim,1984.
Chinese Chemical Letters
2004年 第2期

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