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Monofluoromethylselenylation reagent as well as preparation method and application thereof

A technology of methylthio group and dimethylamino group, which is applied in the field of organic synthesis, can solve problems such as few reports of monofluoromethylselenyl group, and achieves the effects of mild conditions, short steps and simple operation.

Active Publication Date: 2021-08-06
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]At present, there are few reports on the fluoromethylselenyl (SeCH2F) reaction of selenides in the same family as oxygen and sulfur

Method used

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  • Monofluoromethylselenylation reagent as well as preparation method and application thereof
  • Monofluoromethylselenylation reagent as well as preparation method and application thereof
  • Monofluoromethylselenylation reagent as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Operation steps: (1) Add 1.0 mmol of sodium benzenesulfinate, 1.0 mmol of selenium powder, and 0.5 mL of diethylamine in turn to a round-bottomed flask, and stir at room temperature for 12 h to stop the reaction. Post-treatment: suck out the supernatant, filter the residual solid with suction, wash the solid with 3×10 mL ether, and dry it to obtain sodium selenobenzenesulfonate. (2) Add sodium selenobenzenesulfonate, 2.0mL, into a single-necked flask N , N -Dimethylformamide, seal the bottle stopper, put on the air balloon and take out the air in the flask, and then fill it with chlorofluoromethane gas. Put the reaction bottle into an oil bath at 80°C and stir for 5 hours, stop the reaction, and cool to room temperature. Post-processing: extract the reaction liquid 5 times with ethyl acetate and water, wash 3 times with saturated saline, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation under reduced pressure, and purify the residue through a...

Embodiment 2

[0031]Operation steps: (1) Add 1.0 mmol sodium p-toluenesulfinate, 1.0 mmol selenium powder, and 0.5 mL triethylamine in turn to a round-bottomed flask, and stir at room temperature for 12 h to stop the reaction. Post-processing: suck out the supernatant, filter the residual solid with suction, wash the solid with 3×10 mL ether, and dry it to obtain sodium seleno-p-toluenesulfonate. (2) Add sodium selenide p-toluenesulfonate, 2.0 mL, into a single-necked flask N , N -Dimethylformamide, seal the bottle stopper, put on the air balloon and pump out the air in the flask, then fill it with chlorofluoromethane gas until it is observed that the balloon is under normal pressure. Put the reaction bottle into an oil bath at 80°C and stir for 5 hours, stop the reaction, and cool to room temperature. Post-processing: extract the reaction liquid 5 times with ethyl acetate and water, wash 3 times with saturated saline, dry over anhydrous sodium sulfate, remove the solvent by rotary evapor...

Embodiment 3

[0035] Operation steps: (1) Add 1.0 mmol of sodium p-fluorobenzenesulfinate, 1.0 mmol of selenium powder, and 0.5 mL of diethylamine in turn to a round-bottomed flask, and stir at room temperature for 12 h to stop the reaction. Post-treatment: suck out the supernatant, filter the residual solid with suction, wash the solid with 3×10 mL ether, and dry it to obtain sodium seleno-p-fluorobenzenesulfonate. (2) Add sodium seleno-p-fluorobenzenesulfonate, 2.0 mL, into a single-necked flask N , N -Dimethylacetamide, seal the bottle stopper, put on the air balloon and suck out the air in the flask, then fill it with chlorofluoromethane gas until it is observed that the balloon is under normal pressure. Put the reaction bottle into an oil bath at 80°C and stir for 5 hours, stop the reaction, and cool to room temperature. Post-treatment: extract the reaction liquid 5 times with ethyl acetate and water, wash 3 times with saturated saline, dry over anhydrous sodium sulfate, remove the s...

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Abstract

The invention discloses a monofluoromethylselenylation reagent represented by a structural general formula (I) as well as a preparation method and application thereof. The preparation method comprises the steps: by taking common aryl sodium sulfinate as an aryl sulfonylation reagent, selenium powder as a selenium source and monofluoromethane chloride as a monofluoromethylation reagent, firstly, carrying out selenylation reaction in an amine solvent at room temperature; and secondly, carrying out a monofluoromethylation reaction in an amide solvent to obtain the aryl sulfonic acid monofluoromethyl selenate compound. The preparation method disclosed by the invention has the advantages of simplicity in operation, short steps, mild conditions, easiness in post-treatment, no metal participation and the like, the prepared aryl sulfonic acid monofluoromethylselenate is a brand-new selenate compound, and the monofluoromethylselenylation reaction of the third site of an indole compound is successfully realized under photocatalysis.

Description

technical field [0001] The invention relates to a fluoromethylselenide reagent and its preparation method and application, belonging to the technical field of organic synthesis. Background technique [0002] Selenium (Se) is an essential trace element for plants, microorganisms, animals and humans. Selenium-containing compounds have numerous biological activities, such as anti-oxidation, anti-fatigue, immunity, and prevention of liver and gastric mucosal damage, etc. In addition, from the perspective of materials science, organoselenium compounds can also be used as conductive polymers, organic semiconductors and liquid crystal materials Wait. [0003] Due to the unique properties of fluorine atoms, the introduction of fluorine atoms or fluorine-containing functional groups into drug molecules can not only enhance the binding effect, but also help to regulate the membrane permeability, pKa, metabolic stability, and improve bioavailability of the molecules. A fluoromethyl (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00C07D209/30
CPCC07C391/00C07D209/30
Inventor 王永强郭蕊丽
Owner NORTHWEST UNIV(CN)
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