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09CuPCrNi-A

2011年5月2日 by admin

09CuPCrNi-A

【Abstract】 Optically active polymers have a lot of especial functions such as molecular recognition ability, catalytic activity for asymmetric synthesis, asymmetric electrodes and so on.In this paper, 1-menthyl-2-phenylprop-2-en-1-ol, which bearing a bulky group, was synthesized by the reaction of L-menthylformaldehyde withα-styrylmagnesium bromine. 1-menthyl-2-phenylprop-2-en-1-one was synthesized by the oxidation reaction of 1-menthyl-2-phenylprop-2-en-1-ol using Dess-Martin Periodinane (DMP) or PCC as oxidant. 1-menthylprop-2-yn-1-ol was synthesized by the reaction of L-menthylformaldehyde with ethynylmagnesium bromine. 1-menthylprop-2-yn-1-one was synthesized by the oxidation of 1-menthyl-2-phenylprop-2-en-1-ol using DMP or MnO2 as oxidant.We designed three new methods for synthesis of L-menthylformaldehyde, which was an important chiral intermediates. High optically pure L-menthylformaldehyde was prepared by oxidation of menthylmethanol or by reaction of the Grignard reagent derived from menthyl chloride with methyl formate or N,N-dimethyl formamide. Among these routes, the reaction of Grignard reagent derived from menthyl chloride with N,N-dimethyl formamide was the best one. The optimal reaction condition was the Grignard reagent reaction with 1.2 equivalent of DMF at 20 oC for 4 hours. Under optimal reaction condition, the yield was 42.6% and there was no stereoisomer in product. We designed a new method of synthesis menthylacetaldehyde that was an important chiral intermediates. The yield was 82.4%. In the study, we found that 2-phenylacrylaldehyde suffered from the D-A reaction and produced a new substance 3,4-dihydro-2,5-diphenyl-2H-pyran-2-carbaldehyde when it purified by silica-gel column chromatography.We had tried to polymerize the 1-menthyl-2-phenylprop-2-en-1-one by the anionic polymerization and the radical polymerization. The polymerization of 1-menthyl-2-phenylprop-2-en-1-one did not take place because of the large steric hindrance. We also had tried to polymerize 1-menthylprop-2-yn-1-one by the coordination polymerization. Under the given conditions, the polymerization of 1-menthylprop-2-yn-1-one did not take place because of the large steric hindrance. Keywords: 1-menthyl-2-phenylprop-2-en-1-one; 1-menthylprop-2-yn-1-one; L-menthylformaldehyde; synthesize; polymerization

09CuPCrNi-A