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Chemical synthetic method for raphanin

A substrate, ZIF-9 technology, applied in the direction of organic chemistry, etc., can solve the problem of many steps, and achieve the effect of less steps, convenient operation and simple process flow

Inactive Publication Date: 2015-10-28
BEIJING UNIV OF CHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these synthetic sulforaphane routes, there are many steps

Method used

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  • Chemical synthetic method for raphanin
  • Chemical synthetic method for raphanin
  • Chemical synthetic method for raphanin

Examples

Experimental program
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Embodiment 1

[0022] Embodiment 1: (1) synthetic 1-chloro-4-methylthiobutane (compound 3)

[0023] Place the 250mL round-bottom flask reactor in a fume hood, weigh 1.76g (25mmol) sodium methyl mercaptide into the reactor, add 50mL ethanol to dissolve, and then place the round-bottom flask reactor in an ice-water bath at 0°C , quickly inject 4.29g (25mmol) 1-bromo-4-chlorobutane, stir the reaction for 20min under the reaction condition of 0°C, observe the formation of NaBr precipitate, then raise the reaction temperature to room temperature, continue at room temperature The reaction was stirred overnight, and then the reaction mixture was filtered and the solvent was removed to obtain 3.35 g of an oily product (Compound 3), with a yield of 96.5%. Compound 3 was then stored at low temperature.

[0024] Or adopt the following method to synthesize 1-chloro-4-methylthiobutane (compound 3)

[0025] Place the 250mL round-bottom flask reactor in a fume hood, weigh 1.76g (25mmol) sodium methyl mer...

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Abstract

The invention discloses a chemical synthetic method for raphanin and belongs to the technical field of drug synthesis. The chemical synthetic method for raphanin comprises the following three steps of: (1) reacting sodium methyl mercaptide with 1-bromo-4-chlorobutane to generate 1-chloro-4-methyl butyl sulfide; (2) in the presence of a phase transfer catalyst, reacting sodium thiocyanate with 1-chloro-4-methyl butyl sulfide, performing dichloromethane extraction after reaction, and performing rotary evaporation on an organic layer to obtain 1-isothiocyano-4-methyl butyl sulfide; and (3) dissolving 1-isothiocyano-4-methyl butyl sulfide in dichloromethane, performing oxidation by m-chloroperoxybenzoic acid, producing a reaction, and performing purification to obtain a product, namely raphanin. The chemical synthetic method is simple and convenient to operate, requires a few steps, and is high in yield and suitable for large-scale production.

Description

technical field [0001] The invention relates to a new chemical synthesis method of a natural product ratinin which can prevent cancer, and belongs to the technical field of drug synthesis. Background technique [0002] Raphanus (also known as sulforaphane), the English name is Sulforaphane, the chemical name is 1-isothiocyanato-4-methylsulfinyl butane, and the molecular formula is C 6 h 11 NOS 2 , the structural formula is: [0003] [0004] Raphanus is a kind of thioisothiocyanate compound, which widely exists in cruciferous vegetables, and is one of the natural compounds with the best preventive and anticancer effects found so far. Talalay et al. confirmed through experiments that radish compounds eliminate carcinogens in the body with their unique detoxification methods, and exhibit good anticancer activities against pancreatic cancer, colon cancer, breast cancer, lung cancer and prostate cancer (Zhang Y., Talalay P., Cho C.G. et a1. A major inducer of anti-carcino...

Claims

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Application Information

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IPC IPC(8): C07C331/20
Inventor 季生福蒋秀芹张改红
Owner BEIJING UNIV OF CHEM TECH
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