Novel method of preparing isolongifolenone

Abstract

The invention discloses a novel method of preparing isolongifolenone. The method comprises the following steps: by taking isolongifolene (an isomerized product of longifolene) as a raw material, copper power as a catalyst, tertiary butanol as a solvent and tert-butyl hydroperoxide as an oxidizing agent, oxidizing the longifolene in one step to obtain isolongifolenone; at the end of reaction, filtering out the copper powder; evaporating out tertiary butanol at normal pressure; and then carrying out reduced pressure distillation and collecting an isolongifolenone fraction. The novel method disclosed by the invention is simple in operating process, strong in oxidizing selectivity and good in catalytic effect. The catalyst and the solvent can be repeatedly used, and the catalyst is low in price and abundant. The novel method overcomes the deficiencies of existing preparation methods,such as expensive catalysts, complex process and poor reaction selectivity.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a new method for preparing isolongetenone. Background technique [0002] Isolongifenone is a spice with great application value. It has a strong sweet and woody aroma, with amber aroma and slight camphor aroma. In industry, isolongifolenone is an important sesquiterpene, and isolongifolenone and its derivatives have been used in space sprays, cosmetics, detergents, deodorants, fabrics, fibers and in paper products. In addition, isolongifolenone and its derivatives have been found to effectively inhibit the activity of tyrosinase, and are considered to be clinically effective tyrosinase inhibitors for the treatment of some diseases caused by excessive melanin. Dark spots on the skin. In addition, saturated isolongifenone has been used as a ligand for the preparation of chiral estrogens for the prevention and treatment of breast cancer, and as a hormone rep...

AI Technical Summary

Problems solved by technology

However, the catalyst cobalt hexacarbonyl is easy to sublimate and stick to the condensation tube during the reaction process, making it difficult to reuse

Moreover, the catalyst is expensive, and the solvents used, acetonitrile and benzene, are toxic and unfriendly to the environment

Chen Weiqiang et al. used cobalt acetate as a catalyst and air as an oxidant to oxidize isolongifolene to obtain isolongifolene, but the reaction time was too long, up to 48 h, and the yield was also low.