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Beta-chloro tetra-substituted alkenyl sulfone compound and synthesis method thereof

A synthetic method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of wide substrate applicability, easy operation, and mild conditions

Active Publication Date: 2022-03-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, through investigation, it was found that there is still no relevant report on the multi-component difunctionalization reaction of alkyne sulfone to construct multi-substituted alkenyl sulfone compounds in one step.

Method used

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  • Beta-chloro tetra-substituted alkenyl sulfone compound and synthesis method thereof
  • Beta-chloro tetra-substituted alkenyl sulfone compound and synthesis method thereof
  • Beta-chloro tetra-substituted alkenyl sulfone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]Add 0.1 mmol of [(phenylethynyl) sulfone] benzene, 0.3 mmol of methyl acrylate, 0.3 mmol of copper chloride, 0.01 mmol of palladium chloride and 1 ml of acetonitrile solvent in the reaction tube, and rotate at 40 degrees Celsius The reaction was stirred at 500 rpm for 12 hours, and the stirring was stopped. Add 5 mL of saturated sodium chloride solution, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The chromatographic eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 15:1, and the yield was 89%.

[0044] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 and figure 2 shown; the structural characterization data are shown below:

[0045] 1 H-NMR (400MHz, CDCl 3 )δ7...

Embodiment 2

[0052] Add 0.1 mmol 1-methyl-4-[(phenylsulfonyl)ethynyl]benzene, 0.3 mmol methyl acrylate, 0.3 mmol copper chloride, 0.01 mmol palladium chloride and 1 mL acetonitrile to the reaction tube Solvent, stirred and reacted at 45 degrees Celsius at 500 rpm for 12 hours, and stopped stirring. Add 5 mL of saturated sodium chloride solution, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The chromatographic eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 15:1, and the yield was 86%.

[0053] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 and Figure 4 shown; the structural characterization data are shown below:

[0054] 1 H-NMR (400MHz, CDCl 3 )δ7.44(t, J=7.4Hz, 1H), 7.35(dd...

Embodiment 3

[0061] Add 0.1 mmol 1-methoxy-4-[(phenylsulfonyl)ethynyl]benzene, 0.3 mmol methyl acrylate, 0.3 mmol copper chloride, 0.01 mmol palladium chloride and 1 ml Acetonitrile solvent, stirred and reacted at 500 rpm at 45 degrees Celsius for 12 hours, and stopped stirring. Add 5 mL of saturated sodium chloride solution, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The chromatographic eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 5:1, and the yield was 60%.

[0062] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 5 and Figure 6 shown; the structural characterization data are shown below:

[0063] 1 H NMR (400MHz, CDCl 3 )δ7.44(t, J=6.7Hz, 1H), 7.36(d, J=9.7Hz, 2H), 7.28(...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a beta-chloro tetra-substituted alkenyl sulfone compound and a synthesis method thereof. The synthesis method comprises the following steps: adding an alkyne sulfone compound, an olefin compound, a chloride and a catalyst into a reactor, dissolving the alkyne sulfone compound, the olefin compound, the chloride and the catalyst into an organic solvent, carrying out a stirring reaction in the reactor at 40-60 DEG C, cooling the reaction liquid to room temperature after the reaction is finished, and carrying out separation and purification to obtain the beta-chloro tetra-substituted alkenyl sulfone compound. According to the method, an alkyne sulfone compound, an olefin compound and chloride which are simple and easy to prepare are taken as raw materials, and the beta-chloro tetra-substituted alkenyl sulfone compound is efficiently and conveniently constructed through a reaction process of cis-chloropalladium-olefin migration insertion-carbon-palladium bond breakage under the catalysis of palladium chloride. The method has the characteristics of high regioselectivity and stereoselectivity, mild reaction conditions, easily available raw materials, safety in operation, wide substrate applicability and the like, and has a certain application prospect in actual production and research.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a β-chlorinated tetrasubstituted alkenyl sulfone compound and a synthesis method thereof. Background technique [0002] Phenylsulfone-based olefin compounds refer to a class of phenylsulfone-containing (PhSO 2 -) Olefin compounds with good biological activity. This structure is common in various drug molecules, and is widely used in covalent protease inhibitors, antibacterial enzyme inhibitors, neuroprotective agents for the treatment of Parkinson’s and other neurological diseases, integrase inhibitors for the treatment of HIV, etc., in biomedicine, It has great application potential in the field of disease prevention and treatment (Westhuyzen R., Strauss E., J.Am.Chem.Soc., 2010, 132, 12853). At present, there are three main types of literature reports on the synthesis of phenylsulfone-based olefin compounds: (1) the use of cross-coupling reactions between...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/44C07C317/14
CPCC07C315/04C07C317/44C07C317/14Y02P20/584
Inventor 伍婉卿钟文韬江焕峰
Owner SOUTH CHINA UNIV OF TECH
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