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Method for visible light catalytic preparation of alpha-aryl-gamma-methylsulfinylketone compounds

A technology for the preparation of methylsulfinyl ketones and catalysis, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve problems that have not been reported, and achieve low prices, broad industrial application prospects, chemical stable effect

Inactive Publication Date: 2019-02-01
MINNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of DMSO as a methylsulfinyl precursor has not been reported so far

Method used

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  • Method for visible light catalytic preparation of alpha-aryl-gamma-methylsulfinylketone compounds
  • Method for visible light catalytic preparation of alpha-aryl-gamma-methylsulfinylketone compounds
  • Method for visible light catalytic preparation of alpha-aryl-gamma-methylsulfinylketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A method for preparing α-aryl-γ-methylsulfinyl ketones by visible light catalysis, the method is represented by the following reaction formula:

[0026]

[0027]

[0028] The preparation of 4-(methylsulfinyl)-1,2-diphenyl-1-butanone: in the presence of nitrogen at 1 atmosphere, add 2.10 grams of 1,1- Diphenyl-2-propen-1-ol (10 mmol), 0.158 g of 1,2,3,4-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (0.2 mmol) , 9.68 g of trifluoroacetic acid-(2,4,6-trimethoxyphenyl)iodo(III)benzene (20 mmol) and 200 ml of dimethylsulfoxide. At room temperature, place the reaction solution under an 18-watt blue LED light (the distance between the reaction vessel and the light source is about 10-15 cm) until the reaction raw material 1,1-diphenyl-2-propen-1-ol is completely The reaction disappeared (TLC follow-up). After the reaction was completed, distilled water (300 ml) was added to the reaction system, and then the aqueous phase was extracted three times with ethyl acetate (500 ml...

Embodiment 2

[0032] A method for preparing 2-methyl-4-(methylsulfinyl)-1,2-diphenyl-1-butanone compound by visible light catalysis, the method is represented by the following reaction formula:

[0033]

[0034] The preparation of 2-methyl-4-(methylsulfinyl)-1,2-diphenyl-1-butanone: in the presence of nitrogen at 1 atmosphere, add 2.24 gram 2-methyl-1,1-diphenyl-2-propen-1-ol (10 mmol), 0.158 gram 1,2,3,4-tetrakis(carbazol-9-yl)-4,6 -Dicyanobenzene (0.2 mmol), 9.68 g of trifluoroacetic acid-(2,4,6-trimethoxyphenyl)iodo(III)benzene (20 mmol) and 200 mL of dimethylsulfoxide . At room temperature, place the reaction solution under an 18-watt blue LED light (the distance between the reaction vessel and the light source is about 10-15 cm) until the reaction raw material 2-methyl-1,1-diphenyl-2-propene -1-ol completely reacted and disappeared (TLC tracking). After the reaction was completed, distilled water (300 ml) was added to the reaction system, and then the aqueous phase was extracted ...

Embodiment 3

[0038] A method for preparing 1-(4-fluorophenyl)-4-(methylsulfinyl)-2-(2-thienyl)-1-butanone compound by visible light catalysis, the method is represented by the following reaction formula :

[0039]

[0040] Preparation of 1-(4-fluorophenyl)-4-(methylsulfinyl)-2-(2-thienyl)-1-butanone: In the presence of 1 atmosphere of nitrogen, pour into a 200 ml dry Add 2.34 grams of 1-(4-fluorophenyl)-1-(2-thienyl)-2-propen-1-ol (10 mmol), 0.158 grams of 1,2,3,4-tetra (carbazol-9-yl)-4,6-dicyanobenzene (0.2 mmol), 9.68 grams of trifluoroacetic acid-(2,4,6-trimethoxyphenyl) iodine (III) benzene (20 mmol) and 200 ml of DMSO. At room temperature, place the reaction solution under an 18-watt blue LED light (the distance between the reaction vessel and the light source is about 10-15 cm) until the reaction raw material 1-(4-fluorophenyl)-1-(2-thiophene base)-2-propen-1-ol completely reacted and disappeared (TLC tracking). After the reaction was completed, distilled water (300 ml) was a...

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Abstract

The invention discloses a method for visible light catalytic preparation of alpha-aryl-gamma-methylsulfinylketone compounds, wherein 0.1-100.0 mmol alpha-monoarylallyl alcohol compound and 5.0-500.0 mmol dimethyl sulfoxide are used as reaction raw materials, and are subjected to a synthesis reaction under visible light irradiation in 2.0-300.0 ml of a reaction solvent at a room temperature under the synergistic effect of 0.002-2.0 mmol photocatalyst and 0.2-200.0 mmol oxidant organic high-valent iodine compound to prepare a series of the alpha-aryl-gamma-methylsulfinylketone compounds.

Description

technical field [0001] The invention relates to the technical field of organic reactions catalyzed by visible light, in particular to an allyl alcohol compound containing an α-aryl group, under the synergistic action of a photocatalyst and an oxidant, and dimethyl sulfoxide at room temperature and under visible light radiation The technology for preparing α-aryl-γ-methylsulfinyl ketones with important application value by reaction. Background technique [0002] Organic sulfoxides are very common and valuable organic compounds. They not only widely exist in natural products with important biological activities, but are also often used to construct drug molecules with important pharmaceutical activities. [0003] As shown in the following molecular formula: [0004] [0005] Esomeprazole, one of the best-selling drugs in the world, is a drug that can be used to effectively treat duodenal or gastric ulcers. In addition, common drug molecules such as albendazole, a highly e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07D333/22C07C315/04
CPCC07C317/24C07D333/22
Inventor 蔡顺有卢茂建张金旺
Owner MINNAN NORMAL UNIV