N-氨乙基萜品烯马来酰亚胺基酰胺化合物的合成及杀菌活性  

Synthesis and Fungicidal Activity of N-Aminoethyl-TerpineneMaleimide-Based Amide Compounds

作　　者：廖静妮 段文贵[1] 马献力[1,2] 蔺志铎[1] 雷福厚 殷宪龙[1] 

机构地区：[1]广西大学化学化工学院,广西南宁530004 [2]桂林医学院药学院,广西桂林541004 [3]广西林产化学与工程重点实验室,广西南宁530008

出　　处：《高校化学工程学报》2014年第6期1345-1352,共8页Journal of Chemical Engineering of Chinese Universities

基　　金：国家自然科学基金项目(31260164);广西林产化学与工程重点实验室开放基金项目(GXFC11-02);广西大学"大学生创新创业训练计划"项目(111059306)

摘　　要：以α-蒎烯为原料,在质子酸催化下发生重排得到α-萜品烯,再与马来酸酐发生Diels-Alder环加成反应得到α-萜品烯马来酸酐加成物3,然后与乙二胺反应制备N-氨乙基萜品烯马来酰亚胺4。在三乙胺(TEA)催化下,4与各种取代苯甲酰氯发生N-酰化反应,合成得到11个新型N-氨乙基萜品烯马来酰亚胺基酰胺化合物5a^5k。初步探索了合成条件,并利用1H-NMR、13C NMR、FT-IR、ESI-MS、UV-vis和元素分析等多种手段对目标产物作了分析和表征。初步的生物活性测试表明,目标化合物具有一定的杀菌活性,其中3-甲基苯基-N-氨乙基萜品烯马来酰亚胺基酰胺5g在50μg·m L-1浓度下对苹果轮纹病菌的抑制率达63.6%。a-Pinene was converted into a-terpinene by rearrangement in the presence of a protonic acid, followed by Diels-Alder cycloaddtion reaction of a-terpinene with maleic anhydride to obtain a-terpinene-maleic anhydride adduct. Then, N-aminoethyl-terpinene-maleimide was prepared by reacting a-terpinene-maleic anhydride adduct with ethylenediamine. Eleven novel N-aminoethyl-terpinene-maleimide-based amides, referred as 5a-fk, were synthesized by the N-acylation reaction with substituted benzoyl chlorides under catalysis of triethylamine. The synthetic conditions were investigated preliminarily. The target compounds were analyzed and characterized by 1H-NMR, 13C NMR, FT-IR, ESI-MS, UV-vis, and elemental analysis techniques. The preliminary bioactivity measurements showed that the target compounds exhibited a certain fungicidal activity. The compound 3-methylphenyl-N-aminoethyl-terpinene-maleimide-based amide, referred as 5g, had an inhibition rate of 63.6% against Physalospora piricola at a concentration of 50 pg.mL-1.

关 键 词：Α-蒎烯 N-氨乙基萜品烯马来酰亚胺基酰胺 合成 杀菌活性 

分 类 号：O621.1[理学—有机化学]