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有机化学 ›› 2008, Vol. 28 ›› Issue (9): 1649-1654. 上一篇    下一篇

研究简报

1-二茂铁基-3-(4-烷氧基-3-溴苯基)-1,3-丙二酮的合成及其结构表征

刘峻鹏; 李保国* ; 胡瑞珏; 赵海英; 商亚东   

  1. (内蒙古大学化学化工学院 呼和浩特 010121)
  • 收稿日期:2008-03-27 修回日期:2008-03-28 发布日期:2008-09-20
  • 通讯作者: 李保国

Synthesis and Structural Characterization of 1-Ferrocenyl-3- (4-alkoxy-3-bromophenyl)-1,3-propanedione

LIU, Jun-Peng; LI, Bao-Guo*; HU, Rui-Jue; ZHAO, Hai-Ying; SHANG, Ya-Dong   

  1. (College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010121)
  • Received:2008-03-27 Revised:2008-03-28 Published:2008-09-20
  • Contact: LI, Bao-Guo

PDF

1162

被引次数

7

由乙酰基二茂铁(1)与4-长链烷氧基-3-溴苯甲酸甲酯(2)通过酮酯缩合反应, 合成了1-二茂铁基-3-(4-烷氧基-3-溴苯基)-1,3-丙二酮(3). 标题化合物3为首次合成, 具有复杂的共振结构．通过元素分析、红外光谱、核磁共振氢谱对其结构进行了表征. 用X射线单晶衍射法测定了1-二茂铁基-3-(4-十二烷氧基-3-溴苯基)-1,3-丙二酮(3c)的结构, 结果表明: 晶体属于三斜晶系, P-1空间群, a＝0.8677(5) nm, b＝0.8791(5) nm, c＝2.1444(11) nm, α＝101.489(9)°, β＝94.784(10)°, γ＝102.522(9)°, V＝1.5511(14) nm3, Dc＝1.273 g•cm－3, μ＝1.801 mm－1, F(000)＝618, Z＝2, R1＝0.0597, wR2＝0.1386.

关键词: 二茂铁, X射线衍射
, 1,3-丙二酮, 长链烷氧基, 溴取代

The ketone-ester condensation of acetylferrocene (1) with methyl 4-alkoxy-3-bromobenzoates (2) afforded 1-ferrocenyl-3-(4-alkoxy-3-bromophenyl)-1,3-propanediones (3), which showed complicated resonance structures. The structures of 3 were characterized by elemental analysis, IR, and 1H NMR spectra. X-ray diffraction method was also used to determine the structure of compounds 1-ferrocenyl-3-(4-dodecyl- 3-bromophenyl)-1,3-propanedione (3c) and the crystal data belong to triclinic, P-1 space group with unit cell dimensions a＝0.8677(5) nm, b＝0.8791(5) nm, c＝2.1444(11) nm, α＝101.489(9)°, β＝94.784(10)°, γ＝102.522(9)°, V＝1.5511(14) nm3, Dc＝1.273 g•cm－3, μ＝0.005 mm－1, F(000)＝618, Z＝2, R1＝0.0597 and wR2＝0.1386.

Key words: ferrocene, bromo-substitution, X-ray diffracti, long-chained alkoxy, 1,3-propanedione