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Chiral selenourea compound, preparation and application thereof

A chiral compound and compound technology, applied in organic chemistry, analysis by nuclear magnetic resonance, etc., can solve the problem of rare reports of chiral selenourea, and achieve the effect of large chemical shift difference and simple operation.

Active Publication Date: 2017-03-29
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, reports on chiral selenoureas are extremely rare

Method used

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  • Chiral selenourea compound, preparation and application thereof
  • Chiral selenourea compound, preparation and application thereof
  • Chiral selenourea compound, preparation and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0021] The raw material used in the preparation of the chiral selenourea reagent is 3,5-ditrifluoromethylaniline, the reagent used for formylation is formic acid, the catalyst is zinc chloride, and the reaction temperature can be between room temperature and 90 degrees. The reaction time is 3-24 hours; the reagent used in the dehydrogenation of the formylation product is triphosgene or phosgene, the reagent used in the selenogenesis is selenium powder, and the solvent can be one or more of dry dichloromethane, chloroform, tetrahydrofuran, etc. Its mixture, the reaction temperature is the reflux temperature of the solvent, the reaction time is 3-8 hours before adding the selenium powder, and 12-24 hours after adding the selenium powder, the reaction should be completed in the dark, and the product isoselenocyanate should pass through the column layer. It is suggested that the elution solvent can be dry n-hexane, n-pentane, petroleum ether, etc.; the condensation one-step reactio...

example 1

[0024] Example 1 Synthesis of intermediate 3,5-ditrifluoromethylphenylisoselenocyanate

[0025] Add 10g of 3,5-ditrifluoromethylaniline and 1.2g of anhydrous zinc chloride to a 50mL round-bottomed flask, add 10mL of formic acid dropwise at room temperature, continue stirring at room temperature for 10 minutes after the addition, and then heat the mixture to 70 degrees The reaction is about 5 hours. The reaction mixture was cooled to room temperature, diluted with 40 mL of ethyl acetate, washed with water and brine successively, dried over anhydrous sodium sulfate, and the crude product concentrated under reduced pressure was recrystallized from anhydrous ethanol to obtain 10.66 g of formamide.

[0026] Dissolve 1 g of formamide in dry dichloromethane, add 2.25 mL of triethylamine and 2 g of 4A molecular sieves, dropwise add 0.7 g of triphosgene in dichloromethane solution under reflux, and continue to heat and reflux for 4 hours after the dropwise addition Then it was cooled ...

example 21

[0027] Example 21, Synthesis of 2-diphenylethylenediamine-derived diselenourea chiral reagent

[0028] Dissolve 0.21g (S,S)-1,2-diphenylethylenediamine in dry dichloromethane, add 0.64g of 3,5-ditrifluoromethylphenylisoselenocyanate, and the reaction mixture is at room temperature The mixture was stirred overnight in the dark, and then dry n-hexane was added to dilute the reaction solution. A large amount of solid was precipitated. After filtration, washing with n-hexane and vacuum drying, 0.81 g of a white solid product was obtained. Mp 165-166°C; [α] 30 D =31.8(c=1.0in CHCl 3 ); 1 H NMR (400MHz, CDCl 3 ): δ=8.84(br s, 2H), 7.95(br s, 2H), 7.73-7.67(m, 6H), 7.40-7.20(m, 10H), 6.17(s, 2H) ppm; 13 C NMR (100MHz, CDCl 3 ): δ=179.9, 138.1, 136.4, 133.9, 133.6, 133.2, 132.9, 129.3, 128.9, 127.8, 126.8, 124.8, 124.1, 121.4, 120.7, 118.7, 67.6ppm; 77 Se NMR (95MHz, CDCl 3 ): δ=247; ESI-MS: calcd for C32H22F12N4Se2+H 851.0062, found 851.0073.

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Abstract

The invention discloses a chiral compound with a selenourea group structure, and also provides a preparation method and application of the selenourea chiral compound. The structure of the new compound is shown as the specification. The compound is used as a chiral shift reagent to detect the optical purity of chiral carboxylic acid, chiral alcohol, chiral amino alcohol and other chiral compounds, has the characteristics of simple operation and large chemical shift difference, thus being a rapid, efficient, convenient and practical detection means.

Description

technical field [0001] The invention belongs to the technical field of chiral compound synthesis, in particular to a chiral compound having a selenourea group structure, a synthesis method of the selenourea compound and its application in chiral recognition. Background technique [0002] Selenourea and its derivatives are not only an important class of compounds with biological activities such as antibacterial, anti-tumor and anti-cancer, but also an important class of organic synthesis intermediates, and are used in many fields such as pesticides, medicine, optical materials, and electronics industry. has a wide range of applications. [0003] However, reports on chiral selenourea are extremely rare. In view of the great success of chiral thiourea in chiral catalysis and chiral recognition, and selenium and sulfur are the same family elements, their derivatives have strong similarity in structure and performance, and because of their atomic radius ratio The large sulfur m...

Claims

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Application Information

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IPC IPC(8): C07C391/00G01N24/08
Inventor 边广岭宋玲杨士伟黄华银宗华
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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