Method for selectively synthesizing allyl sulfone compounds

An allyl sulfone and compound technology, which is applied in the field of selective synthesis of allyl sulfone compounds, and can solve the problems of lack of practicability, limited versatility, unstable raw materials and the like

Active Publication Date: 2020-10-23
WUHAN INSTITUTE OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2005, Nozhnin et al. reported the method of generating allyl sulfone compounds with sulfonyl chloride and α-methylstyrene derivatives under the catalysis of ketones, but the versatility of the reaction was limited, and pungent odor was used in the reaction triethylamine
In 2012, Li et al. reported a method for synthesizing allyl sulfone compounds with sulfonyl hydrazide and α-methylstyrene derivatives as raw materials under the action of TBAI and TBHP. This reaction has the instability of sulfonyl hydrazide and the reaction time is too long. long-term disadvantages
The main disadvantage of this method is that it requires strict anaerobic conditions and lacks practicality.
[0005] Although various methods for preparing allyl sulfone compounds have been disclosed in the present technology, these methods have disadvantages such as unstable raw materials, long reaction times, difficult operation or expensive catalysts.

Method used

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  • Method for selectively synthesizing allyl sulfone compounds
  • Method for selectively synthesizing allyl sulfone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The specific steps are: add 0.3mmol 1-nitro-2-phenylpropene, 0.4mmol sodium benzenesulfinate and 3mL DMSO to a 50mL round-bottomed flask, stir and react with magnetic force at 100°C for 7 hours, then extract with ethyl acetate The reaction solution, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was separated by column with ethyl acetate / petroleum ether=1:10 / V as the eluent The desired product was obtained after purification, and the product was a white solid with a yield of 85%.

[0019] The proton nuclear magnetic spectrogram result of gained product is: 1 H NMR (600MHz, CDCl 3 ,ppm)δ7.77(d,J=7.8Hz,2H),7.52(t,J=7.2Hz,1H),7.40(t,J=7.8Hz,2H),7.27–7.20(m,5H), 5.57(s,1H), 5.20(s,1H), 4.26(s,2H).

Embodiment 2

[0021] The specific steps are: add 0.3mmol 1-nitro-2-phenylpropene, 0.35mmol sodium p-methoxybenzene sulfinate and 3mL NMP to a 50mL round bottom flask, and stir the reaction at 80°C for 5 hours, then use The reaction solution was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product, which was rinsed with ethyl acetate / petroleum ether=1:15 / V Liquid was subjected to column separation and purification to obtain the desired product, which was a white solid with a yield of 89%.

[0022] The proton nuclear magnetic spectrogram result of gained product is: 1 H NMR (600MHz, CDCl 3 ,ppm)δ7.67(d,J=9.0Hz,2H),7.26–7.20(m,5H),6.85(d,J=9.0Hz,2H),5.57(s,1H),5.19(s,1H ), 4.23(s,2H), 3.80(s,3H).

Embodiment 3

[0024] The specific steps are: add 0.3mmol 1-nitro-2-(4-bromophenyl)propene, 0.44mmol sodium p-methoxybenzene sulfinate and 3mL DMF to a 50mL round bottom flask, and stir the reaction under magnetic force at 90°C After 4 hours, the reaction solution was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product, which was prepared with ethyl acetate / petroleum ether = 1:10 / V is the eluent and the desired product is obtained by column separation and purification. The product is a white solid with a yield of 83%.

[0025] The proton nuclear magnetic spectrogram result of gained product is: 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.71(d,J=8.8Hz,2H),7.30–7.26(m,2H),7.00–6.89(m,4H),5.55(s,1H),5.20(s,1H),4.24 (s,2H), 3.87(s,3H).

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Abstract

The invention relates to a method for selectively synthesizing an allylic sulfone compound. The method comprises the steps of: adding solvent to raw materials of nitroolefin and sodium sulfinate whichis stable and easy to operate, directly heating the obtained mixture while stirring is conduced, and performing treatment on the heated mixture to obtain the allylic sulfone compound. The method hasthe advantages that no addition of catalysts is needed, the whole system is open, and the yield is high; through the adoption of the direct heating method, the sodium sulfinate can be used as a mild Lewis base in the above reaction; the key step of the reaction is that the equilibrium between the nitroolefin and an allyl nitro compound is promoted by the Lewis base, and the stable nitroolefin is converted into the allyl nitro compound, which is more prone to a free-radical addition reaction, through the key step; therefore, the reaction can be conducted more easily under a mild condition, andthe speed of the reaction is increased, so that the compound with an allylic sulfone structure is effectively synthesized.

Description

technical field [0001] The invention relates to a method for selectively synthesizing allyl sulfone compounds in an open system directly heated without adding a catalyst, and belongs to the technical field of organic and pharmaceutical synthesis. [0002] technical background [0003] Allyl sulfone compounds can be used as reactants or intermediates in many organic synthesis reactions. It can be used as a synthon in many reactions, such as the addition of 1,1- or 1,3-dipole. Meanwhile, allyl sulfone compounds exhibit various pharmacological activities such as: antitumor activity, anti-inflammatory efficacy, antifungal and inhibition of HIV-1 reverse transcriptase. Allyl sulfone compounds and their derivatives also widely exist in many natural compounds, organic synthetic molecules and drug molecules, and are a very important functional group in drug synthesis and organic synthesis. Therefore, the research on the synthesis method of allyl sulfone compounds has aroused great i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B45/00C07C315/00C07C317/14C07C317/22C07D333/18
Inventor 陈云峰雷雪郑镭张传新
Owner WUHAN INSTITUTE OF TECHNOLOGY
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