糠醛及其衍生物的脱氢枞胺席夫碱的合成与性能  

Synthesis and Perfomances of Dehydroabietylamine Schiff Base Containing Furfural and Its Derivatives

作　　者：宋彦佩 王珏 刁开盛 陈厚发 段运明 

机构地区：[1]广西林产化学与工程重点实验室广西民族大学化学化工学院,广西南宁530008 [2]郑州市新郑梅久实业有限公司,河南郑州450000

出　　处：《林产化学与工业》2017年第6期101-109,共9页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(21567004)

摘　　要：以糠醛及其衍生物和脱氢枞胺为原料制备了4种新型的脱氢枞胺席夫碱:5-硝基糠醛-脱氢枞胺席夫碱(1)、糠醛-脱氢枞胺席夫碱(2)、5-溴糠醛-脱氢枞胺席夫碱(3)和5-甲基糠醛-脱氢枞胺席夫碱(4),通过单因素和正交试验优化了合成条件,席夫碱1~4在优化条件下的产率分别为89.5%、89.1%、90.2%和88.1%;采用红外光谱、核磁共振、质谱和X射线单晶衍射对其结构进行了表征,确认了4种席夫碱的结构,席夫碱1和2都属于斜方晶系,P2(1)2(1)2(1)空间群,席夫碱3属于单斜晶系,P2(1)空间群。实验测得的分子结构参数与计算化学模拟结果吻合程度高,该系列席夫碱采用DFT算法所得的N(1)C(21)的键长分别为0.127 67、0.127 91和0.127 88 nm,而单晶衍射分析的结果为0.127 5(5)、0.126 1(5)和0.124 5(7)nm;键角C(20)—N(1)—C(21)的模拟值分别为121.610 1、120.760 7和120.813 5°,单晶测试的实际值为119.1(3)、117.3(3)和117.4(5)°。4种席夫碱的抑菌活性测试结果表明:席夫碱1对金黄色葡萄球菌的最小抑菌浓度为0.31 g/L,与阳性对照头孢尼西相当,显示出较高的抑菌活性;席夫碱1、3和4对大肠杆菌的最小抑菌浓度均为0.62 g/L,抑菌活性明显优于席夫碱2。Four new dehydroabietylamine Schiff bases, i. e. , （E） -1-DHAA-N-（ （ 5-nitrofuran-2-yl ） methylene ） （ 1 ）, （E） -N- （furan-2-ylmethylene）-1-DHAA （ 2 ）, （ E ）-N-（ （ 5-bromofuran-2-yl ） methylene ）-1-DHAA （ 3 ）, （ E ）-1-DHAA-N-（ （ 5- methylfuran-2-yl） methylene ） （4）, were prepared from furfural derivative and dehydroabietylamine （DHAA）. The process conditions were optimized by single factor and orthogonal experiment. The yields of Sehiff bases 1 -4 were 89.5%, 89. 1%, 90. 2% and 88. 1%, respectively. Their structures were characterized and confirmed by X-ray single crystal diffraction, NMR, MS, IR. Both Schiff base 1 and 2 belonged to orthorhombie system, space group P2 （ 1 ） 2 （ 1 ） 2 （ 1 ）, Schiff base 3 belonged to monoelinie system, space group P2 （1）. The practical structural parameters were in agreement with the calculated chemical simulation results. The bond lengths of the DFT algorithm were 0. 127 67, 0. 127 91 and 0. 127 88 nm, respectively, while the results of the single crystal diffraction analysis were 0. 127 5（5）, 0. 126 1 （5） and 0. 124 5（7） nm. The simulated values of bond angle of C（20）-N（ 1 ）-C（21 ） were 121. 610 1, 120. 760 7 and 120. 813 5°, respectively, and the actual values of the single crystal test were 119. 1 （3）, 117. 3 （3）, and 117.4 （5） o. The antibacterial activities of 4 Schiff bases were studied, whichshowed that the minimum inhibitory concentration of Schiff base 1 on Staphylococcus aureus was 0. 31 g/L, which was equivalent to the positive control of cephanisisi, indicating a higher antibacterial activity ; the minimum bacteriostatic concentrations of Schiff base 1, 3 and 4 against Escherichia coli were 0. 62 g/L, and the antimicrobial activity was significantly better than Schiff base 2.

关 键 词：脱氢枞胺 羰醛缩合 X-ray单晶衍射 量化计算 抑菌性能 

分 类 号：TQ35[化学工程]