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Application of porcine pancreatic lipase as catalyst of asymmetric aldol reaction of heterocyclic ketone and aromatic aldehyde

A technology of porcine pancreatic lipase and heterocyclic ketones, which is applied in the chemical field to achieve the effects of high yield, broad application prospects, and high ee value

Inactive Publication Date: 2012-06-27
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 aldol reaction with heterocyclic ketones as donors has not been reported at home and abroad.

Method used

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  • Application of porcine pancreatic lipase as catalyst of asymmetric aldol reaction of heterocyclic ketone and aromatic aldehyde
  • Application of porcine pancreatic lipase as catalyst of asymmetric aldol reaction of heterocyclic ketone and aromatic aldehyde
  • Application of porcine pancreatic lipase as catalyst of asymmetric aldol reaction of heterocyclic ketone and aromatic aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1, Porcine pancreas lipase catalyzed activity confirmation of heterocyclic ketone and aromatic aldehyde asymmetric aldol reaction

[0028] In this example, the reaction of 1-Boc-4-piperidone and p-nitrobenzaldehyde was used as a template reaction to confirm the activity of porcine pancreatic lipase in catalyzing the asymmetric aldol reaction between heterocyclic ketones and aromatic aldehydes. The experimental method is: add 1-Boc-4-piperidone (0.25mmol) and p-nitrobenzaldehyde (0.50mmol) in the reaction flask, do not add catalyst or add catalyst, then add 1mL solvent (divided by sodium bicarbonate The catalyst is ethanol as the solvent, and the rest of the catalysts are added with a water-acetonitrile mixed solvent with a volume ratio of 1:9), and the temperature is controlled at 25°C to stir the reaction; after the reaction is completed, filter, the filter cake is washed with dichloromethane, and the filtrates are combined and washing solution, dilute with w...

Embodiment 2

[0033] Example 2. Methodological research on the asymmetric aldol reaction of heterocyclic ketones and aromatic aldehydes catalyzed by porcine pancreatic lipase

[0034]In this embodiment, the reaction of 1-Boc-4-piperidone and p-nitrobenzaldehyde is used as a template reaction, and the main influencing factors (solvent, water content) of the asymmetric aldol reaction of heterocyclic ketones and aromatic aldehydes catalyzed by porcine pancreatic lipase , substrate feed ratio, enzyme amount, reaction temperature, reaction time) were systematically studied.

[0035] 1. The influence of solvent

[0036] Add 1-Boc-4-piperidone (0.25mmol), p-nitrobenzaldehyde (0.50mmol) and porcine pancreatic lipase (50mg) into the reaction flask, then add 1mL solvent, and stir the reaction at 25°C for 120 hours , aftertreatment method is the same as embodiment 1. The results are shown in Table 2.

[0037] Table 2 The effect of solvent on the asymmetric aldol reaction catalyzed by porcine panc...

Embodiment 3

[0050] Example 3, General investigation on the asymmetric aldol reaction of heterocyclic ketones and aromatic aldehydes catalyzed by porcine pancreatic lipase

[0051] This example investigates the versatility of porcine pancreatic lipase in catalyzing the asymmetric aldol reaction of heterocyclic ketones and aromatic aldehydes. The experimental method is: add heterocyclic ketone (0.25mmol), aromatic aldehyde (0.25mmol) and porcine pancreatic lipase (50mg) into the reaction flask, then add 1mL of aqueous acetonitrile (V water / V acetonitrile = 0.10), control the temperature for 30 ℃ stirring reaction for 120~144 hours, aftertreatment method is the same as embodiment 1. The results are shown in Table 3.

[0052] Table 3 Porcine pancreatic lipase catalyzes the asymmetric aldol reaction of heterocyclic ketones and aromatic aldehydes

[0053]

[0054]

[0055] It can be seen from Table 3 that the asymmetric aldol reaction of heterocyclic ketones and aromatic aldehydes cat...

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Abstract

The invention discloses an application of porcine pancreatic lipase as a catalyst of asymmetric aldol reaction of heterocyclic ketone and aromatic aldehyde. The aromatic nucleus of the aromatic aldehyde is connected with an electron withdrawing substituent, and the aromatic aldehyde has the advantages of good catalytic activity, high enantiomeric selectivity, environmental friendliness, good economical performance and the like. The invention also provides a method of using the porcine pancreatic lipase to catalyze the asymmetric aldol reaction of the heterocyclic ketone and the aromatic aldehyde, the yield is high, and the ee (enantiomeric excess) value is high. The scope of application of the porcine pancreatic lipase is broadened, a potentially excellent catalyst is provided for the asymmetric aldol reaction, and the porcine pancreatic lipase has broad application prospects in the field of asymmetric synthesis.

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 asymmetric aldol reaction between heterocyclic ketones and aromatic aldehydes, and the application of porcine pancreatic lipase to catalyze heterocyclic ketones A method for asymmetric aldol reaction with aromatic aldehydes. 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 recent years, because by studying their u...

Claims

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Application Information

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IPC IPC(8): C12P17/12C12P17/06C12P17/00
Inventor 官智何延红付建平
Owner SOUTHWEST UNIVERSITY
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