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Chemical synthesis method of sulforaphane

A synthesis method and technology of sulforaphane, applied in the direction of organic chemistry, etc., can solve problems hindering the market application of sulforaphane, very high requirements for production conditions and process equipment, difficulties in preservation, storage and transportation of sulforaphane, and achieve Great application prospects and market development prospects, stable properties, and high product yield effects

Active Publication Date: 2011-06-15
杭州雷布新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although sulforaphane can be obtained by means of extraction from plants, sulforaphane is very easy to degrade in the process of separation and purification, which requires very high production conditions and process equipment, and there are also problems in the preservation, storage and transportation of sulforaphane. great difficulty
These factors have greatly hindered the market application of sulforaphane

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Put 76g of 1,3-propanediol and 169g of 48% hydrobromic acid (HBr) in a three-necked flask, start stirring, slowly add 100g of triethylamine dropwise, heat to reflux state, when the reaction is over, cool to room temperature, divide The remaining oil at the bottom of the bottle was taken, washed with dilute NaOH solution until neutral, and dried with anhydrous sodium sulfate. After the solvent was evaporated, a colorless transparent liquid was obtained, namely 138 g of monosubstituted 3-bromo-1-propanol. The yield was 99.28%.

Embodiment 2

[0026] Put 76g of 1,3-propanediol and 169g of 48% hydrobromic acid (HBr) in a three-necked flask, start stirring, add 10g of α-pyrrolidone, heat to reflux state, when the reaction is over, cool to room temperature, and separate Oil remained at the bottom of the bottle, washed with dilute NaOH solution to neutrality, and dried with anhydrous sodium sulfate. After distilling off the solvent, a colorless transparent liquid was obtained, namely 135 g of monosubstituted 3-bromo-1-propanol, yield It is 97.12%.

[0027] (2) Preparation of 4-methylsulfonyl-1-butanol:

Embodiment 3

[0029] Under the protection of nitrogen, add 31.2g dimethyl sulfoxide to a dry three-necked flask, add 10g sodium hydride to react at normal temperature, cool in an ice-water bath after the reaction is complete, add dropwise 111g of 3-bromo-1-propanol, and control The reaction temperature is below 10°C. After the reaction is complete, warm up to room temperature, wash with a small amount of absolute alcohol to remove NaH, then wash with water, and wash with CH 2 Cl 2 Extract 3 times, take the organic layer and wash with anhydrous Na 2 SO 4 Drying, filtration and rotary evaporation, a large amount of white crystals were precipitated, and the filter cake was recrystallized with 95% ethanol to obtain white needle-like crystals which were 4-methylsulfonyl-1-butanol, weighed 52g after drying, and the yield was 95.59 %.

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Abstract

The invention discloses a chemical synthesis method of sulforaphane. The method is characterized by comprising the following steps of: (a) in the presence of a catalyst, heating 1,3-propylene glycol and hydrobromic acid for reacting to obtain 3-bromine-1-propyl alcohol; (b) reacting dimethyl sulfoxide and sodium hydride at normal temperature, after the dimethyl sulfoxide and the sodium hydride completely react, adding the 3-bromine-1-propyl alcohol, and stirring; after the 3-bromine-1-propyl alcohol completely reacts, washing with a small quantity of water; extracting by using dichloromethane, taking an organic layer, and carrying out spin evaporating on the organic layer to obtain white solid 4-methylsulfonyl-1-butanol; (c) dissolving the 4-methylsulfonyl-1-butanol in an organic solvent, adding a chlorinated reagent for a chlorinated reaction to obtain 1-chlorine-4-methylsulfonyl butane; and (d) under the protection of nitrogen, dissolving the 1-chlorine-4-methylsulfonyl butane in an organic solvent, adding a thiocyanide reagent and heating, after the reaction ends, washing with water, extracting by using an organic solvent, and carrying out spin evaporating to remove the solvent to obtain faint yellow oily liquid, i.e. the sulforaphane. The method has the advantages of simpleness of operation, high yield and stable product.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a chemical synthesis method of sulforaphane. Background technique [0002] In recent years, the incidence of cancer has been increasing year by year, and cancer has seriously affected human health. [0003] Since sulforaphane is an isothiocyanate compound with the strongest anti-oxidation, anti-cancer and anti-cancer abilities existing in nature, sulforaphane has become a research hotspot in recent years, and it has been proved to be the most powerful compound found so far. Phasen enzyme inducer. [0004] The results of animal research and in vitro cell culture experiments show that sulforaphane is a multifunctional enzyme inducer, which can induce the body to produce n-type detoxification enzyme-glutathione transferase (GS) and tyrosine reductase (QR). It can neutralize suspected carcinogens and prevent carcinogens from destroying genetic factors in healthy cells, thereby playing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/20C07C331/20
Inventor 徐倩陈伟良傅锦浩金志敏
Owner 杭州雷布新材料有限公司
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