Synthesis And Study Of3-oxo-ionol Esters

3-oxo-a-ionol and its derivatives are important tobacco flavor precursors, which achieved the uniform release of flavor, enhanced the quality of odor, reduced the amount of spice and improved the quality of tobacco products, so they were widely applications in tobacco industry. A variety of free acids released in the cigarette burning process, especially isobutyric acid,3-methylbutanoic acid and3-methylpentanoic acid could gift cigarette with unique aroma, and enhance the safety, combustibility and inherent quality, in additional, this could generate a robust, pleasant and comfortable odour. Herein, a series of3-oxo-a-ionol esters (3-oxo-a-ionyl isobutyrate,3-oxo-ionyl valerate and3-oxo-a-ionyl-3’-methyl valerate) were synthesized though a variety of methods including carbonyl reduction by sodium borohydride, acetylation by chloride, allylic oxidation by TBHP, hydrolyzation and esterification. The structures and properties of these as-synthesized compounds and intermediates were characterized by NMR and HRMS.In this thesis, the optimum conditions of synthesis of3-oxo-a-ionol esters were obtained by exploring the impact on the synthesis and optimizing the synthetic methods. Finally, the pyrolysis of the as-synthesized3-oxo-a-ionyl isobutyrate,3-oxo-ionyl valerate and3-oxo-a-ionyl-3’-methyl valerate were carry out and the results indicate that3-oxo-a-ionol esters could produce megastigmatrienone and free acids in the cigarette burning process, which enhanced the quality of cigarette smoke.