Study On The Synthesis Methods Of Dihydroindene Catalyticed By The Acid

Numerous natural products and synthetic compounds which have important biological properties such as anti-bacterial activity possess the dihydroindene skeleton. To this group belong those produced by biopolymerization of oxystyrenes and oxystilbenes.Traditionally industry methods mainly finished with the help of hard base or acid Which need to deal with the a lot of hard acid and base, In the laboratory , they generated from the cross cuppling or intramolecular rearrangement of aryl ring with their side-chains.Whereas, thoses transition metals are subject to limitations in the Industrial-production because of the their high price and significant toxicity,So we explore two styrenes catalyzed by the protonic acid or Lewis acidWe xplores a PhP(O)HOR-catalyzed Dimerisation of Styrenes in the acidic environment,This solvent-free,effective system require mild reaction conditions and avoid the pollution in environment come from the transition metals. Other five dimers of styrene derivatives were obtained in the process of the further expansion of substrate based on optimizing reaction conditions.At last ,we elucidate the influence of architecture and electron effects of substrates on the yield of dihydroindene according to the different substrate needs different reaction condition.In the process of investigation of mechanism that Dimerisation of Styrenes using a PhP(O)HOR/H+ . Dihydroindene were isolated from the Dimerisation of Styrenes as the by-product, and the Carbocation mechanism were further verificated . Meanwhile ,we found that the dihydroindene and the dimer of styrene will obtained at the same time from the styrene catalyzed by proton acid.With the asarone as a template substrate ,we improve the yield of dihydroindene to70% via the temperature-control and solvent and get the conclusion that the Ph and temperature of the reaction system are two key factors affecting the yield of dihydroindene.In order to expand the scope of the catalyst as well as taking into account the Lewis acid will help the proton to depart from benzene ring to make it restore aromaticity when the carbonic attack on the ring to form dihydroindene .At first ,we verify primarily three Lewis acid will catalysis the formation of the dihydroindene with taking the asarone as a template substrate, and then, make the yield of dihydroindene increased to 65% by changing the conditionsof the experiment . Compare with the proton acid, Lewis acid catalyzition avoid effect of oxidation and carbonization come from the hard acidIn the fourth chapter of this paper, the cytotoxic activities of five of them were determined in vitro by an 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay using Hela, MCF-7, Bel-7402 and A549. Results indicated that all of the compounds exhibited cytotoxic activities against cancer cells, especially against Bel-7420. But at the same time, the compounds also exhibited cytotoxic activities against human normal liver cell line (LO₂).In conclusion,we have successfully achievet the catalytic Dimerisation of Styrenes through a Carbocation process by using a PhP(O)HOR/H+ and .this method provides asimple route to And then,we explore two new catalyzed system according to the catalytic mechanism ,one is protonic acid ,another is Lewis acid and improve the yield of dihydroindene to70%and 65%. At the end of the work ,five dimers of styrenes were test by MTT assay on growth of four different tumor cell lines (MCF-7, Bel-7402, A549 and Hela)and The results revealed that these compounds showed strong potential antitumor activities.