Method for synthesizing optically pure glabridin

A glabridin and optical technology, which is applied in the field of organic synthesis and fine chemicals, can solve the problems of high price, inability to obtain large quantities, and restrictions on the harvesting of licorice, and achieve the effect of cost reduction

Active Publication Date: 2021-11-16
HEBEI UNIV OF TECH
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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, and the total yield was 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, the total yield is only 20%

Method used

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  • Method for synthesizing optically pure glabridin

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Effect test

Embodiment 1

[0045] 1. Synthesis of Compound I:

[0046] Under argon atmosphere, 2,4-dimethoxybromobenzene (200 g, 0.92 mol) was dissolved in 1,4-dioxane (1 L), and cesium carbonate (330 g, 1.01 mol) was added successively , cuprous iodide (3.8 grams, 0.02 moles), 2-pyridinecarboxylic acid (4.9 grams, 0.04 moles) and diethyl malonate (162 grams, 1.01 moles), stirred at 100 ° C for 16 hours, and TLC detected the raw materials Consumed completely. The reaction solution was poured into ice water (1 liter), stirred for 0.5 hours, separated, the aqueous phase was extracted with ethyl acetate (200 ml×3), the organic phases were combined, washed with saturated brine (200 ml×1), The organic phase was concentrated to obtain a large amount of solid, which was filtered to obtain compound I (254 g, yield 93%, white solid, melting point 53-55° C.). 1 H NMR (CDCl 3 ,400MHz): δ7.25(1H,br s,Ar-H),6.50(1H,dd,J=6.6,1.6Hz,Ar-H),6.46(1H,dd,J=1.6Hz,Ar-H ),5.02(1H,s,Ar-CH),4.27-4.17(4H,m,-CH 2 CH 3 ),3.80...

Embodiment 2

[0065] Other steps are the same as in Example 1, except that in step 1, 1,4-dioxane is replaced by methyl tert-butyl ether;

[0066] In step 3, N,N-dimethylformamide was replaced by acetonitrile.

[0067] In step 5, dimethyl sulfoxide is replaced by N,N-dimethylformamide;

[0068] In step 6, methanol is replaced by N, N-dimethylformamide: a mixed solvent of water=0.2:1, and potassium hydroxide is replaced by potassium carbonate;

Embodiment 3

[0070] Other steps are with embodiment 1, difference is,

[0071] In step 1, 1,4-dioxane is replaced by tetrahydrofuran; cesium carbonate is replaced by potassium phosphate;

[0072] In step 3, dimethyl sulfoxide is replaced by acetonitrile, and acetic anhydride is replaced by vinyl acetate;

[0073] In step 6, methanol is replaced by ethanol, and potassium hydroxide is replaced by lithium hydroxide.

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Abstract

The invention relates to a method for synthesizing optically pure glabridin. According to the method, chiral carbon of optically pure glabridin is constructed through biological enzyme catalysis, optically pure glabridin is prepared in combination with an organic synthesis method, and the key steps are that a chiral intermediate compound III is generated by using a lipase catalysis compound II, and an important intermediate compound IV is obtained through a bromination reaction. According to the method for synthesizing optically pure 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 method for synthesizing optically pure 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 is highly valued by international research and application fields such as beauty, makeup, medicine and health care, showing 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 important ...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04C07B2200/07Y02P20/55
Inventor 古国贤王英明韩恩山章文军何艳贞刘洁翔朱令之李小菊王瑞虎
Owner HEBEI UNIV OF TECH
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