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Application of immobilized lipase Lipozyme TLIM as catalyst for unsymmetrical Michael addition reaction

A technology of immobilizing lipase and addition reaction, applied in the direction of fermentation, etc., to achieve the effect of good selectivity, good catalytic activity and selectivity, and easy operation

Inactive Publication Date: 2010-11-24
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the enzyme-catalyzed asymmetric Michael addition reaction has not been reported in the literature

Method used

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  • Application of immobilized lipase Lipozyme TLIM as catalyst for unsymmetrical Michael addition reaction
  • Application of immobilized lipase Lipozyme TLIM as catalyst for unsymmetrical Michael addition reaction
  • Application of immobilized lipase Lipozyme TLIM as catalyst for unsymmetrical Michael addition reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～11

[0014] Examples 1-11, Michael addition reactions catalyzed by different enzymes

[0015]

[0016] In a round bottom flask was added trans-2,4-dichloro-β-nitrostyrene (120 mg, 0.55 mmol), diethyl malonate (177 mg, 1.1 mmol), deionized water (1 mL), dimethyl Sulfoxide (DMSO, 5mL) and enzyme (400mg) were stirred and reacted at room temperature (25-30°C); after the reaction was completed, filtered, the filter cake was washed with dichloromethane, the washing liquid was combined with the filtrate, diluted with water, and then used Extract with dichloromethane, combine the dichloromethane extracts, dry with anhydrous sodium sulfate, distill off the solvent under reduced pressure to obtain a crude product, and purify the crude product by flash column chromatography to obtain the target product. The reaction conditions and results are shown in Table 1.

[0017] Table 1 Michael addition reactions catalyzed by different enzymes

[0018]

[0019] As can be seen from Table 1, the ...

Embodiment 12～46

[0020] Examples 12-46, Lipozyme TLIM catalyzes the asymmetric Michael addition reaction of 2-cyclohexenone and acetylacetone

[0021]

[0022] Add 2-cyclohexenone, acetylacetone, deionized water, organic solvent and Lipozyme TLIM in a round-bottomed flask, and stir the reaction at a certain temperature; Combine with the filtrate, dilute with water, extract with dichloromethane, combine the dichloromethane extracts, dry with anhydrous sodium sulfate, distill off the solvent under reduced pressure to obtain a crude product, purify the crude product with flash column chromatography to obtain target product. The reaction conditions and results are shown in Table 2.

[0023] Table 2. Asymmetric Michael addition reaction of 2-cyclohexenone and acetylacetone catalyzed by Lipozyme TLIM

[0024]

[0025]

[0026] Note: The ee value was not detected in Examples 35-46.

[0027] It can be seen from Table 2 that the asymmetric Michael addition reaction catalyzed by the immobili...

Embodiment 47～51

[0028] Examples 47-51, Asymmetric Michael addition reaction of 4-chloro-β-nitrostyrene and ethyl acetoacetate

[0029]

[0030] Add 4-chloro-β-nitrostyrene (3.0mmol), ethyl acetoacetate (1.0mmol), deionized water (0.5mL), DMSO (5mL) and catalyst (200mg) in a round bottom flask, 35°C Stir the reaction; after the reaction is completed, filter, wash the filter cake with dichloromethane, combine the lotion with the filtrate, dilute with water, extract with dichloromethane, combine the dichloromethane extracts, dry with anhydrous sodium sulfate, reduce The solvent was distilled off under high pressure to obtain a crude product, which was purified by flash column chromatography to obtain the target product. The reaction conditions and results are shown in Table 3.

[0031] Table 3. Asymmetric Michael addition reaction of 4-chloro-β-nitrostyrene with ethyl acetoacetate

[0032]

[0033] It can be seen from Table 3 that the Michael addition reaction of 4-chloro-β-nitrostyrene ...

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Abstract

The invention relates to novel application of substance, in particular to application of immobilized lipase Lipozyme TLIM as a catalyst for an unsymmetrical Michael addition reaction. The invention has the advantages of wide substrate applicability, good and catalysis activity and selectivity, easy operation, and can be recycled. The invention further provides a method of using the immobilized lipase Lipozyme TLIM to catalyze the unsymmetrical Michael addition reaction. The method has high yield and favorable selectivity.

Description

technical field [0001] The invention relates to a new application of substances, in particular to the application of immobilized lipase Lipozyme TLIM as a catalyst for asymmetric Michael addition reaction. Background technique [0002] The nucleophilic addition of carbanions formed by active methylene compounds to the carbon-carbon double bond of α, β-unsaturated carbonyl compounds is an important method for the alkylation of active methylene compounds. This reaction is called Michael Addition reaction. Michael addition reactions are usually catalyzed by bases, or homogeneously catalyzed by the combination of amines and carboxylic acids or Lewis acids, and the use of these catalysts has caused some environmental problems. Therefore, more and more attention has been shifted to environmentally friendly catalysts in recent years. As a green and effective catalyst, the application of biocatalyst in organic synthesis is gradually increasing. As a novel biocatalyst, hydrolases ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/00C12P7/26
Inventor 官智何延红蔡建峰
Owner SOUTHWEST UNIVERSITY
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