Organic catalyst containing primary amine, tertiary amine and urea or thiourea and preparation method thereof

A technology of organic catalyst and organic solvent, applied in the field of organic catalysis, to achieve the effect of unique structure, novel structure and easy preparation

Inactive Publication Date: 2009-12-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Multiple functional groups such as primary amine, tertiary amine, and thiourea are purposely introduced into an organic molecule, so that it can exhibit catalytic behavior similar to enzymes in the reaction, and multiple functional groups can coordinate to enhance the performance of the activated substrate. Such catalysts have not yet been reported

Method used

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  • Organic catalyst containing primary amine, tertiary amine and urea or thiourea and preparation method thereof
  • Organic catalyst containing primary amine, tertiary amine and urea or thiourea and preparation method thereof
  • Organic catalyst containing primary amine, tertiary amine and urea or thiourea and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Under argon protection, (1R,2R)-1,2-cyclohexanediamine (6.85g, 0.06mol) and dichloromethane (60mL) were added to a 250mL flask, cooled to 0°C in an ice-water bath, and added dropwise with Boc 2 A solution of O (4.37 g, 0.02 mol) in dichloromethane (50 mL). The addition was completed within 30 minutes, the ice-water bath was removed, the temperature was naturally raised to room temperature, and the reaction was carried out at room temperature for 24 hours. Add water (30mL) to dissolve the white solid, extract with dichloromethane (25mL×3), dry, and concentrate to dryness under reduced pressure, add water (80mL), adjust the pH value to about 5 with 4M concentrated hydrochloric acid, add diethyl ether ( 50mL) extraction, standing still, liquid separation, the aqueous phase was extracted with diethyl ether (20mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain (1R, 2R)-2-aminocyclohexylam...

Embodiment 2

[0043] Cinchonidine (2.94g, 10.0mmol) and triphenylphosphine (3.15g, 12.0mmol) were dissolved in freshly distilled THF (50mL), and cooled to 0°C in an ice-water bath. Under stirring, diisopropyl azodicarboxylate (2.43 g, 12.0 mmol) was added rapidly in one portion. Maintaining at 0°C, freshly distilled THF (20 mL) containing diphenylphosphoryl azide (DPPA, 3.30 g, 12.0 mmol) was added dropwise to the above reaction solution. After the dropwise addition, the reaction solution was naturally warmed to room temperature, reacted for 12 hours, and then heated to 50° C. for 2 hours. Additional triphenylphosphine (3.41 g, 13.0 mmol) was added and heating was maintained until no further gas evolution occurred (ca. 2h). After the reaction, the reaction solution was cooled to room temperature, water (1 mL) was added, stirred for 3 h, and then concentrated in vacuo to remove the solvent. Add dichloromethane-10% hydrochloric acid (1:1, 100mL) to dissolve the residue, let it stand and sep...

Embodiment 3

[0047] Under stirring, THF (40mL) dissolved with RBCS (3.07g, 12.0mmol) was added dropwise to freshly distilled THF (20mL) dissolved with 9-amino cinchonidine (2.93g, 10.0mmol). Stir overnight. After the reaction was completed, the solvent was removed by vacuum concentration, and the residue was separated and purified by silica gel column chromatography to obtain RBCD (4.67 g), a precursor of a multifunctional organic catalyst, with a yield of 85%.

[0048]

[0049] Under stirring, RBCD (2.75 g, 5.0 mmol) was dissolved in 1,4-dioxane (100 mL), and 4M hydrochloric acid (100 mL) was added to react at room temperature for 8 h. Concentrate in vacuo to dryness, add water (100mL) to dissolve, adjust the pH value in the range of 13-14 with 1M sodium hydroxide, a large amount of white suspended matter appears, extract with dichloromethane (4×50mL), combine the organic phases, and dry Dry over sodium sulfate and concentrate in vacuo to obtain RNCD (2.1 g) with a yield of 93%.

[0...

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Abstract

The invention relates to an organic catalyst, in particular to an organic catalyst containing primary amine, tertiary amine and urea or thiourea and a preparation method thereof. One catalyst molecule respectively includes one or more primary amine functional groups, one ore more tertiary amine functional groups and one or more urea or thiourea functional groups. The designed multi-functional organic catalyst is novel in structure and simple and convenient in preparation method; since a plurality of the functional groups of primary amine, tertiary amine and thio(urea) exist in the organic catalyst molecule, the good synergetic effect can be shown during the catalytic asymmetric organic reaction, the high catalytic efficiency and the high optical selectivity can be displayed, and the organic catalyst can be well applied to the asymmetric reaction of various types of organic catalysis and has wide application range.

Description

technical field [0001] The present invention relates to organic catalysis, specifically a class of organic catalysts containing primary amines, tertiary amines, and urea or thiourea and their preparation. One catalyst molecule contains one or more primary amines, one or more tertiary amine, and one or more urea or thiourea functional groups. Background technique [0002] Asymmetric catalysis is one of the most active fields in organic chemistry today, and it is a strong theoretical basis and academic basis for the development of chiral drugs, materials, spices and other chemicals. Enzymes and metal complexes are two of the most dominant and efficient classes of catalysts, among which metal complexes are the most studied chemical catalysts. In recent years, metal-free organic small molecule catalysis has attracted more and more attention, and has increasingly become a powerful method for synthesizing or constructing complex chiral organic molecular frameworks. It is becoming...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/04B01J31/02C07B53/00C07C205/45C07C201/12
Inventor 梁鑫淼李鹏飞叶金星王永灿
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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