Synthesis And Structural Characterization Of Chiral Para - Vinylidene Vinyl Monomers

Helical polymers have been exhibited wide application prospects in chiral separation, molecular recognition, asymmetric catalysis and optical crystal materials and so on. During the synthesis of helical vinyl polymers, the steric hindrance and the chiral induction of the side groups play a very important role in the stability of the helical conformation of polymers, and so, design and synthesis of chiral monomers with proper structures is the key issue. The optically active binaphthalene derivatives is a class of chiral compounds with C2 symmetry axis, and there are a lot of modification sites on the backbone. Helical vinyl polymers bearing chiral binaphthyl side group have been showed out the potential application values in molecular recognition, asymmetric reduction of ketones, asymmetric epoxidation of α,β-unsaturated ketones, and asymmetric addition reaction between aldehydes and metallic organic compounds, it provided the basis for the following test of biological activity.In this paper, using optically active(S)-binaphthol(BINOL) as chiral source, two kinds of new vinyl monomers bearing binaphthyl side group were prepared by modifying the chemical structures on the backbone of BINOL, and the monomers are expected to preapre the helical vinyl polymers with helical structures.As a medium in organic synthesis, water has the advantages of low cost, no pollution and easily separation of products. Isoxazole ring is an important skeleton structure of many antidiabetic molecules, and three compounds containing isoxazole ring structure were synthesized by the three component "one pot" reaction in the aqueous phase. The main contents of this paper are as follows:1. Using(S)-BINOL as starting material, monomers(S)-2-hydroxy-2’-triphenyl methoxy-3-vinyl-1,1’-binaphthyl,(S)-1,1’-binaphthyl-2,2’-diacrylate bearing chiral binaphthyl side groups were synthesized, and the chemical structures of these compounds were identified by NMR. The yield of the products was improved by optimizing the synthetic conditions, and at the same time, the synthetic process of(S)-2-hydroxy-2’-triphenyl methoxy-3-vinyl-1,1’-binaphthyl was optimized.2. Starting from 2-naphthol, aromatic aldehyde and 3-amino-5-methylisoxazole, four kinds of compounds containing isoxazole ring were prepared in “one pot” in aqueous medium. The chemical structures of the compounds were identified by NMR. The effects of reaction conditions, such as catalyst, solvent and reaction time on the yield of the target molecules were investigated.