The Research Of Asymmetric Reduction Of M-phenylpropanol Use Plant Cells

Chiral arylalcohols are versatile group as chiral building block for the syntheses of pharmaceuticals, agrochemicals, pharmaceutical intermediates and fine chemicals, etc, These alcohols may be obtained by enantioselective reduction of prochiral ketones. This paper described the selective reduction to prepare chirle pharmacuetical intermediate, m-chlorophenylpropanol, from m-chloropropiophenone using plant tissue and callus. Some reaction conditions were investigated in detail. This study mainly includes the following contents:Firstly, benzene, as raw material, was treated by series reaction of nitration, substitution and reduction and so on to synthesize m-chloropropiophenone. The total yield was above 74.1%.Secondly, the plant cell culture of five kinds plant such as carrot, cucumber, onion, potato and Apium graveolens L were prepared. The experiments reveal that the proportion of cytokinin and auxin in early culture time of callus culture is belows:Daucus carrot 1,Cucumis sativus Linn 1:1,Allium cepa 2:1,Solanum tuberosum 1.5:1,Apium graveolens root 2:1,Apium graveolens sticks 1:1, Apium graveolens leaves 1:1; the proportion of subculture:Daucus carrot 2:0.5,Cucumis sativus Linn 3:1,Allium cepa 2:0.5,Solanum tuberosum 3:1,Apium graveolens root 2.5:1,Apium graveolens sticks 3:1, Apium graveolens leaves 2:1.Thirdly, the catalyst asymmetric reduction of m-chloropropiophenone using plant tissue was studied. The effect of shape of plant tissue, pH, temperature, concentration of substrate and reaction time were mainly investigated base on the conversion rate and ee. The best conversion rate and ee of the reaction can reach 84.9% and 91.2%. But the effect of conversion rate is lower in high substrate concentrations.To improving the reaction effective in high substrat concentration, the callus cell was used as a catalyst and the reaction conditions were changed. The experiment data were delived that:Allyl-alcohol compounds was improve the ee effectivly but debase the conversion; preheating cell was to improve the ee; small molecule alcohol may debase the conversion too; phosphate buffer effects are not significant. The conversion and ee can reach 96% and 96 through optimizing the reaction.In a word, the preparation, characterization and application of plant tissue and cell were carried out in asymmetric reduction of the m-phenylpropanol. Some important information was obtained. It will be useful for the application of plant tissue and cell.