Method for synthesizing 3-substituted-2-indolone compounds under catalysis of lipase

A technology of lipase and indolinone, which is applied in the field of biocatalysis, can solve the problems of condensation reactions that have not been reported in the literature, and achieve the effects of wide application range of substrates, low production costs and strong competitive advantages

Active Publication Date: 2015-08-05
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process involves reacting two different chemicals together at room temperature with an enzyme called Lipase (EC 3.1.1) that helps create certain molecules from fat or oil. These products can be used alone or combined into larger structures like flavors or fragrances.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding ways to improve the activity, selectivity, yield, and purities of certain chemical products made from substituent 2-substitutes Indoline-3-ols through novel techniques like Microwave Method, Ultrasound Method, Grounding Technique, Layer Hydrogen Fluorescence Imaging Analysis System, Liquatino X Reagent Interchange Using Lasers, Acoupling Responsive Modes, Solvothermal Amplifying Factor Chain Endonuclease, etc., which offer unique benefits over existing technologies due to its ability to efficiently perform complex types of transformations without requiring expensive materials.

Method used

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  • Method for synthesizing 3-substituted-2-indolone compounds under catalysis of lipase
  • Method for synthesizing 3-substituted-2-indolone compounds under catalysis of lipase
  • Method for synthesizing 3-substituted-2-indolone compounds under catalysis of lipase

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Embodiment 1

[0039] Biological enzymes and other reagents involved in the present invention are purchased from the market, and wherein the reagents are not further purified; proton nuclear magnetic resonance (1HNMR) is measured with a Bruker Advance 2B 400 nuclear magnetic resonance spectrometer, and the frequency is 400MHz, and the solvent is deuterated Dimethyl sulfoxide, internal standard is tetramethylsilyl (TMS).

[0040] In all examples, lipase-catalyzed Knoevenagel condensation reaction of aromatic aldehydes and indol-2-ones, the reaction equation is:

[0041] .

example 1

[0042] Example 1: 2 mmol p-nitrobenzaldehyde and 2 mmol indol-2-one are added in a 10 ml reaction flask, then 125 mg of porcine pancreatic lipase, 1 ml of deionized water, 4 ml of DMSO are stirred and reacted at 45° C. TLC (petroleum ether / ethyl acetate, 1 / 1, v / v) monitored the progress of the reaction. After 10 hours, filter out the enzyme, filter out the enzyme after the reaction, filter paper and filtrate with CH 2 Cl 2 Wash with water three times. The filtrate was extracted three times with 5ml of water and 10ml of ethyl acetate, the combined organic phases were washed with anhydrous MgSO 4After drying and filtering, rotary evaporation under reduced pressure, the crude product was separated by column chromatography [petroleum ether / ethyl acetate, 9 / 1-2 / 1, v / v] to obtain the purified target product with a yield of 94.2%, mp: 245–250°C. 1 H NMR (400 MHz, DMSO) δ 10.72 (s, 1H), 8.35 (d, J = 8.7 Hz, 2H), 7.95 (d, J = 8.4 Hz, 2H), 7.67 (s, 1H), 7.41 (d , J = 7.7 Hz, 1H), 7...

example 2

[0043] Example 2: 2 mmol o-nitrobenzaldehyde and 2 mmol indol-2-ketone are added in a 10 ml reaction flask, then 125 mg porcine pancreatic lipase, 1 ml deionized water, 4 ml DMSO are stirred at 45° C. TLC (petroleum ether / ethyl acetate, 1 / 1, v / v) monitored the progress of the reaction. After 10 hours, the enzyme was filtered out, and the enzyme was filtered out after the reaction was completed. The filter paper and the filtrate were respectively washed with CH 2 Cl 2 Wash with water three times. The filtrate was extracted three times with 5ml of water and 10ml of ethyl acetate, the combined organic phases were washed with anhydrous MgSO 4 After drying and filtering, rotary evaporation under reduced pressure, the crude product was separated by column chromatography [petroleum ether / ethyl acetate, 9 / 1-2 / 1, v / v] to obtain the purified target product with a yield of 89.2%, mp: 199-200°C. 1 H NMR (400 MHz, DMSO) δ 10.54 (s, 1H), 8.17 (d, J = 8.2 Hz, 1H), 8.03 (s, 1H), 7.86 –...

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Abstract

The invention discloses a method for generating 3-substituted-2-indolone compounds by use of a Knoevenagel condensation reaction with aromatic aldehydes and indol-2-ones as substrates and lipase as a catalyst. The 3-substituted-2-indolone compounds are important intermediates for synthesizing indole alkaloids, and meanwhile, and have wide pharmacological and physiological activity. According to the method, the product yield is 87.8-94.2%; the method is mild in reaction conditions, simple to operate, low in production cost, high in yield, wide in substrate spectrum and low in environmental pollution.

Description

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Claims

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Application Information

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Owner NANJING UNIV OF TECH
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