Synthesis Of Phenylalanine Iron Porphyrin And Its Catalytic Properties

Porphyrins and their metal complexes have wide applications in analytical chemistry,materials, medicine and catalysis especially in biomimetic reactions.Metalloporphyrin was considered as enzyme-catalyzer of cytochrome P450, whichshowed high catalytic activity and selectivity for the oxidation of hydrocarbons under mildreaction conditions. The research of simulating the single plus oxygenase cytochrome P450by using Metalloporphyrin may be contribute to understanding the catalytic mechanism ofcytochrome P450as well as having a broad application prospects in organic synthesis andmedicine.The main contents of this paper are as follows：1. The design and synthesis of the phenylalanine-substituted porphyrins and their ironcomplexes:5-(2-hydroxyphenyl)-10,15,20-triphenylporphyrin (o-OHTPP) was made toreact with1,2-dibromoethane to generate5-o-(2-bromoethoxylphenyl)-10,15,20-tri-phenylporphyrin (o-Br-C2-TPP). At last, phenylalanine substituted porphyrin can bereadily metallated with Iron by using Iron chloride as the raw material and acetonitrile asthe solvent.2. The target compounds was characterized by UV-visible, FTIR,1HNMR and massspectrometry.3. Catalytic epoxidation of styrene with iron porphyrins were investigated in differentsolvents and with different axial ligands. Experimental results showed that tail L (D)-phenylalanine iron(Ⅲ) porphyrin exhibited no enantioselectivity in the catalyticepoxidation of styrene. The epoxidation yield in different solvents followed the order,acetonitrile> dichloromethane> methanol while the yield in the presence of differentaxial ligands was found to be in the order, pyridine>4-nitro-imidazole> imidazole.