Method for synthesizing glabridin

Abstract

The invention relates to a method for synthesizing glabridin. According to the method, 2, 4-dimethoxy bromobenzene and diethyl malonate are used as starting raw materials, a key intermediate compound III is prepared through a cuprous iodide catalytic coupling reaction, a reduction reaction and a bromination reaction, methyl-protected glabridin is prepared through nucleophilic substitution and a Friedel-Crafts reaction, and glabridin is obtained after methyl is removed. According to the method for synthesizing glabridin, raw materials are cheap and easy to obtain, and the total yield is high.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and fine chemicals, and in particular relates to a synthesis method of glabridin. Background technique [0002] Glabridin is a kind of flavonoids, which has the functions of whitening, antibacterial, anti-allergy, anti-cancer, anti-oxidation, anti-spasm, anti-inflammatory, liver protection, free radical scavenging, and blood fat and blood pressure lowering. It has received more and more attention from research and application fields such as international beauty, makeup, medicine and health care, and has shown good development prospects (Wang Xudong et al., Fine Chemical Intermediates, 2021, 51(3), 6-9.). At present, the way to obtain glabridin in my country is mainly from the precious plant Glycyrrhiza glabra, which cannot be obtained in large quantities. In my country, Glycyrrhiza glabra mainly grows in the south of the Tianshan Mountains. The harvest of licorice is limited, which makes it very ...

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Problems solved by technology

At present, the way to obtain glabridin in my country is mainly from the precious plant Glycyrrhiza glabra, which cannot be obtained in large quantities. In my country, Glycyrrhiza glabra mainly grows in the south of the Tianshan Mountains. The harvest of licorice is limited, which makes it very important to develop an effective chemical synthesis method for the preparation of glabridin

[0003] In 2013, Wenhua et al. (Synthetic Communications, 2014, 44, 540-546) reported a method for preparing racemic glabridin by using resorcinol as a raw material through 10 steps of reaction, with a total yield of only 14%; in 2018, the patent Document CN109232603A discloses a method for preparing racemic glabridin with 7-hydroxycoumarin as the starting material through 8-step reaction, with a total yield of 20%. The key step is the Suzuki coupling reaction, and the required boric acid reagent and The metal palladium catalyst is expensive; in 2018, the patent document CN 108440553A disclosed a method for preparing optically pure glabridin by using metal ruthenium to catalyze the isoflavone intermediate, but the patent did not give a detailed synthesis method of the isoflavone intermediate; In 2020, the patent document CN111362961A discloses a method for preparing R-configuration glabridin by using 7-hydroxychroman-4-one as the starting material through 7-step reaction, with a total yield of 30%. Although this method can Preparation of optically pure glabridin, but the starting material 7-hydroxychroman-4-one is not a bulk chemical product, and the price is expensive (>200,000 yuan / kg)

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