The Synthesis Of The Homologue Compounds Of New 5-(10)-Undecenethylacetamide-acenaphthene

Enantiomers have same physical and chemical properties and spectra expect rotary property, which have important applications to development of new drugs and functional materials. So study of enantiomers has been important field nowadays. In this paper, it is mainly about the synthesis of homologue compounds of 5-(10)-undecenacetamido-acenaphthene. Recent study showed that 5-(10)-undecena cetamido-acenaphthene is likely to invert in achiral solvents. According to previous study, two new compounds 5-(10)-undecenisobutyramido-acenaphthene and 5-(10)-undecenpropeonamido-acenaphthene derived from acenaphthene were designed. The synthetical processes of the compounds were via acenaphthene as material, the Fridel-Crafts acetylation reaction to the carbon of the acenaphthene ring, deoxi dization reaction to the ketone, acetylation reaction to the amidocyanogen, and final purification by flash chromatography. The higher pure products were obtained. So far, in all kinds of literature in domestic and abroad, there had been no report on HPLC analysis of 5-(10)-undecenisobutyramidoacenaphthene and 5-(10)-undecenpropionamido-acenaphthene. In this paper, the result of two enantiomers were analysed by high performance liquid chromatography and on-line polariscope. The effect of different CSP columns, different percentage of mobile phase (isopropyl alcohol and n-hexane) and temperature to the analysis were investigated experimentally. The results of the experiment showed that the analytical conditions of 5-(10)-undecenylpropionamido-acenaphthene as follows: flow rate 2.0ml/min, temperature 20.0℃, mobile phase, isopropyl alcohol: n-hexane=6.0:94.0, DNB-PG CSP column, laevorotation; the analytical conditions of 5-(10)-undecenisobutyr -amido-acenaphthene as follows: flow rate 2.0ml/min, temperature 20.0℃, mobile phase, isopropyl alcohol: n-hexane=4.0:96.0, DNB-PG CSP column, dextrorotation. For the chiral carbon is linked with the only different isopropyl and ethyl, its steric block and polarizable groups has effecton rotative way. In addition, in order to observe its separation due to functional group variation, allyl-acenaphthene-ethelamido enantiomer was synthesized, on the basis 5-(10)-undecenacetamido-acenaphthene, by means of replacing allyl chloride with 10-undecenyl, and amide being turned into amine. Several new enantiomer compounds synthesized could be not only linked with silica gel for preparing novel Pirkle CSPs, but also as potential enantiomers for investigation of the enantiomer inversion in achiral solvents. It has greatly practical significance.