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Application of porcine pancreas lipase as catalyst for Michael addition reaction

A porcine pancreatic lipase and addition reaction technology, which is applied in the application field of porcine pancreatic lipase as a catalyst for Michael addition reaction, can solve the problems that benzalone coumarin has not been reported at home and abroad, etc., and achieve excellent catalyst and good catalytic activity , the effect of high yield

Inactive Publication Date: 2012-06-13
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of different chemical methods can be used to synthesize warfarin, the synthesis of warfarin by biotransformation has not been reported at home and abroad.

Method used

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  • Application of porcine pancreas lipase as catalyst for Michael addition reaction
  • Application of porcine pancreas lipase as catalyst for Michael addition reaction
  • Application of porcine pancreas lipase as catalyst for Michael addition reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1. Confirmation of the activity of porcine pancreatic lipase to catalyze the Michael addition reaction of 4-hydroxycoumarin and α,β-unsaturated ketone

[0025] In this example, the reaction of 4-hydroxycoumarin and benzylidene acetone (that is, 4-phenyl-3-buten-2-one) was used as a template reaction to catalyze 4-hydroxycoumarin and α , The activity of the Michael addition reaction of β-unsaturated ketones was confirmed. The experimental method is: add 4-hydroxycoumarin (0.5mmol) and benzylidene acetone (0.6mmol) into the reaction flask, add no catalyst or add catalyst (50mg), then add 0.1ml water and 0.9ml DMSO, and control the temperature Stir and react at 25°C for 144 hours; after the reaction, remove the enzyme by filtration, dilute the filtrate with 25ml of water and extract with ethyl acetate, combine the dichloromethane extracts, dry with anhydrous sodium sulfate, filter, and distill the filtrate to remove the solvent under reduced pressure, then Purif...

Embodiment 2

[0030] Example 2. Methodological study on the Michael addition reaction of 4-hydroxycoumarin and α,β-unsaturated ketone catalyzed by porcine pancreatic lipase

[0031] In this embodiment, the reaction of 4-hydroxycoumarin and benzylidene acetone is used as a template reaction, and the main influencing factors of the Michael addition reaction of porcine pancreatic lipase catalyzed 4-hydroxycoumarin and α, β-unsaturated ketones ( Solvent, water content, substrate feed ratio) were systematically studied.

[0032] 1. The influence of solvent

[0033] Add 4-hydroxycoumarin (0.5mmol), benzylidene acetone (0.6mmol) and porcine pancreatic lipase (50mg) into the reaction flask, then add 0.1ml of water and 0.9ml of organic solvent, and stir the reaction at 25°C for 96 Hour; Aftertreatment method is the same as embodiment 1. The result is as figure 1 As shown, porcine pancreatic lipase showed the best catalytic activity in DMSO, and the highest yield reached 38%; it showed better ca...

Embodiment 3

[0038] Example 3. Porcine pancreatic lipase catalyzes the Michael addition reaction of 4-hydroxycoumarin and α,β-unsaturated ketone to synthesize benzylacetone coumarin and its derivatives

[0039] This example investigates the versatility of porcine pancreatic lipase-catalyzed Michael addition reaction of 4-hydroxycoumarin and α,β-unsaturated ketone to synthesize warfarin and its derivatives. The experimental method is: add 4-hydroxycoumarin (0.5mmol), α,β-unsaturated ketone (2.5mmol) and porcine pancreatic lipase (50mg) into the reaction bottle, then add 0.1ml water and 0.9ml DMSO, The reaction was carried out under temperature control and stirring for 144 hours, and the aftertreatment method was the same as in Example 1. The results are shown in Table 2.

[0040] Table 2 Michael addition reaction of 4-hydroxycoumarin and α,β-unsaturated ketone catalyzed by porcine pancreatic lipase

[0041]

[0042]

[0043] It can be seen from Table 2 that (1) porcine pancreatic ...

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Abstract

The invention discloses an application of porcine pancreas lipase as a catalyst for a Michael addition reaction of 4-hydroxycoumarin and alpha, beta-nonsaturated ketone, the catalytic activity is good; the invention also provides a method for synthesizing an anticoagulation agent warfarin and its derivative by using porcine pancreas lipase for catalyzing the Michael addition reaction, the yield is high, the application scope of the porcine pancreas lipase is widened, a potential excellent catalyst is provided for the Michael addition reaction, and a method with the characteristics of high efficiency, environmental protection and economy is provided for the synthesis of the warfarin and its derivative, and possesses wide application prospect in the organic synthesis field.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to a new application of porcine pancreatic lipase in organic synthesis, in particular to the application of porcine pancreatic lipase as a catalyst for the Michael addition reaction of 4-hydroxycoumarin and α, β-unsaturated ketones, and A method for synthesizing warfarin and its derivatives by using porcine pancreatic lipase to catalyze the Michael addition reaction of 4-hydroxycoumarin and α, β-unsaturated ketone. Background technique [0002] Enzyme catalysis is a kind of efficient and green organic synthesis tool due to its high selectivity, mild conditions and potential reproducibility. In addition, enzyme catalysis is also multifunctional, mainly manifested in the fact that a natural enzyme molecule can catalyze other chemical reactions besides natural reactions, and such reactions may have nothing to do with natural reactions. This property of enzymes has received much attention in rec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/06
Inventor 官智何延红谢帮华
Owner SOUTHWEST UNIVERSITY
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