The Research Of Region-Selectivity Ring Opening Of Fluorene Oxirane And The Synthesis Of β-Amino Alcohols

β-Amino alcohols is an important class of organic compounds, which has considerable use in medicinal chemistry. The most practical and widely used route to the synthesis of these compounds is nucleophilic aminolysis of epoxides under catalyst. Accordingly, the development of regionselectivity catalysts perform the epoxide ring opening reactions with amines under mild conditions of practical methods for synthesis ofβ-amino alcohols is of great importance. This thesis mainly focuses on the following three aspects:First part, catalyst screening: 2-（2,7-dichloro-9H-fluoren-4-yl） oxirane was synthesized from fluorene by chloration, acylation and reduction with KBH₄. A variety of catalysts （mainly in Lewis acids） about their catalysis activity in aminolysis of 2-（2,7-dichloro-9H-fluoren-4-yl） oxirane were discovered. Finally, ZrOCl₂·7H₂O was found to have best catalysis ability. Its region-selectivity rate was up to over 85%. Various factors were thoroughly studied in relation to the amount of catalysts, the dosage of catalysts, solvent and reaction temperature on regionselectivity.Second part, the sythesis ofβ-amino alcohols: 15 new 2,7-Dichlorofluorine derivatives substituted with amino alcohols in the presence of ZrOCl₂·7H₂O as catalyst were designed. They were synthesized by the reaction of 2-（2,7-dichloro-9H-fluoren-4-yl）oxirane with morpholine, piperidine, aniline, 2-aminopyrimidin, p-aminotoluene, m-toluidine, o-toluidine, 2,5-dimethylamine, p-chloroaniline, o-chloroaniline, 3,5-dichloramine, 2,4-difluroaniline. The structures of all the new compounds were confirmed by H NMR, IR and MS.Third part, biological activity screening: Five new compounds were chosen to carry out the preliminary pharmacodynamic evaluation on mouse leukaemia cell and anthropo-epoxidase-2（hCox-2） depressor.