A kind of synthetic method of γ-crotonyl lactone and its derivatives

A technology for the synthesis of crotonyl lactone and its method, which is applied in the field of synthesis of γ-crotonyl lactone and its α-derivatives, can solve the problems of difficult large-scale production and use, high price, etc., and achieve easy industrial production , cheap reagents, and mild conditions

Inactive Publication Date: 2017-04-12
CHONGQING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] Although γ-crotonyl lactone has been commercialized for a long time, its price has always been high due to factors such as equipment, yield, energy consumption and various reagent costs, making it difficult to produce and use on a large scale

Method used

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  • A kind of synthetic method of γ-crotonyl lactone and its derivatives
  • A kind of synthetic method of γ-crotonyl lactone and its derivatives
  • A kind of synthetic method of γ-crotonyl lactone and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] At room temperature, 1 (26 g, 0.2 mol) was added to a solution of acetone (1000 mL) to form a molar concentration of 0.2 mol.L -1 organic solution, then add H 2 O (10 mL), add hydrochloric acid (1 mL) drop by drop under vigorous stirring, after the addition is complete, continue stirring at room temperature for 12 hours, carefully add solid sodium bicarbonate to neutralize to neutral, filter with celite, wash with dichloromethane , combine the filtrate, remove most of the organic solvent by distillation under reduced pressure, add water, extract the water layer with dichloromethane, combine the organic layer, dry over anhydrous magnesium sulfate, filter, remove the solvent by distilling the filtrate under normal pressure, the remaining liquid column chromatography (dichloromethane Methane / methanol) afforded γ-crotonyl lactone 7 (14 g, 82%).

[0053]

[0054] 1 H NMR (300 MHz, CDCl 3 ): δ 4.91 (dd, 2H, J = 2.4, 1.6 Hz), 6.15 (dt, 1H, J = 6.0, 1.6 Hz), 7.57 (m, 1H)....

Embodiment 2

[0056] At room temperature, 1 (13 g, 0.1 mol) was added to a solution of acetone (100 mL) to form a molar concentration of 1 mol.L -1 organic solution, then add H 2 O (10 mL), add hydrochloric acid (1 mL) dropwise under vigorous stirring, after the addition is complete, continue to stir at room temperature for 8 hours, carefully add solid sodium bicarbonate to neutralize to neutral, filter with diatomaceous earth, and wash with dichloromethane , combine the filtrate, remove most of the organic solvent by distillation under reduced pressure, add water, extract the water layer with dichloromethane, combine the organic layer, dry over anhydrous magnesium sulfate, filter, remove the solvent by distilling the filtrate under normal pressure, the remaining liquid column chromatography (dichloromethane Methane / methanol) afforded γ-crotonyl lactone 7 (6.9 g, 82%).

[0057]

[0058] 1 H NMR (300 MHz, CDCl 3 ): δ 4.91 (dd, 2H, J = 2.4, 1.6 Hz), 6.15 (dt, 1H, J = 6.0, 1.6 Hz), 7.57 ...

Embodiment 3

[0060] At room temperature, 1 (13 g, 0.1 mol) was added into acetone (1000 mL) solution to form a molar concentration of 0.1 mol.L -1 organic solution, then add H 2 O (10 mL), add hydrochloric acid (1 mL) dropwise under vigorous stirring, after the addition is complete, continue stirring at room temperature for 16 hours, carefully add solid sodium bicarbonate to neutralize to neutral, filter with Celite, wash with dichloromethane , combine the filtrate, remove most of the organic solvent by distillation under reduced pressure, add water, extract the water layer with dichloromethane, combine the organic layer, dry over anhydrous magnesium sulfate, filter, remove the solvent by distilling the filtrate under normal pressure, the remaining liquid column chromatography (dichloromethane Methane / methanol) afforded γ-crotonolactone 7 (7.1 g, 84%).

[0061]

[0062] 1 H NMR (300 MHz, CDCl 3 ): δ 4.91 (dd, 2H, J = 2.4, 1.6 Hz), 6.15 (dt, 1H, J = 6.0, 1.6 Hz), 7.57 (m, 1H).

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Abstract

The invention relates to a synthetic method for gamma-crotonolactone and a derivative thereof. In the synthetic method for the gamma-crotonolactone, the gamma-crotonolactone is prepared from a 2,5-dihydrofuran compound used as a raw material through the hydrolysis reaction; the derivative of the gamma-crotonolactone is alpha-derivative of the gamma-crotonolactone; the alpha-derivative of the gamma-crotonolactone is prepared through performing the Baylis-Hillman reaction on the gamma-crotonolactone. The gamma-crotonolactone and the alpha-derivative thereof have quite wide application in the organic synthetic chemistry and medicinal chemistry. The synthetic method has the advantages that the raw materials are easy to obtain, the reagent is low in price, the route is simple and short, the condition is moderate, the operation is simple, and the industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a synthesis method of γ-crotonyl lactone and α-derivatives thereof. Background technique [0002] γ-crotonolactone (γ-crotonolactone), also known as 2(5H)-furanone, 5H-furan-2-one, etc., is an organic heterocyclic compound, the simplest butenolide, room temperature It is a colorless liquid, its structural formula is γ-crotonyl lactone is the precursor material of many active pharmaceutical molecules, and its structure is commonly found in biologically active molecules, such as antibiotics, antibiotics, antitumor, and antiviral drugs. From a structural point of view, it is a lactone, which has the properties of a general ester, such as being able to be reduced and ammonolyzed; it contains a double bond conjugated with an ester, and can undergo Micheal addition and Diels-Alder reaction; because it is connected to oxygen , coupled with the electron-withdrawing effect of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 汪春霞杨英张菊花
Owner CHONGQING NORMAL UNIVERSITY
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