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研究了格氏试剂与马来海松酸三甲酯(2)的各官能团的反应活性差异,获得了2个区域选择性加成产物(化合物3和4),各化合物的结构均经元素分析、NMR和MS表征,用COSY,HMQC和HMBC进一步对化合物3进行了结构分析,并由X射线单晶衍射确认了其立体结构.实验结果表明,2上的3个甲酯基的位阻影响了加成反应的选择性,内酯3的生成阻止了其进一步生成TADDOL(tetraaryl-1,3-dioxolane-4,5-dimethanols)类产物,但反应不影响松香环式原有的立体结构.产物3和4有望作为手性衍生试剂.
The differences of reactivity between Grignard reagent and trimethylolpropane trimethacrylate (2) were studied. Two regioselective addition products (compounds 3 and 4) were obtained. The structures of the compounds were characterized by elemental analysis, NMR and MS. The structure of compound 3 was further analyzed by COZY, HMQC and HMBC, and the three-dimensional structure was confirmed by X-ray single crystal diffraction.The experimental results showed that the steric hindrance of the three methyl ester groups on 2 affected The selectivity of the addition reaction, the formation of lactone 3 prevented its further formation of TADDOL (tetraaryl-1,3-dioxolane-4,5-dimethanols) class of products, but the reaction does not affect the rosin ring original stereo structure. 3 and 4 are expected as chiral derivatization reagents.