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Method of preparing chrysin

A technique for chrysin and trimethoxybenzene, applied in the field of preparing chrysin, can solve the problems of high price, low synthesis total yield and efficiency, long route, etc., and achieves improved synthesis yield and efficiency, high industrial application prospect , the effect of simplifying the synthesis route

Inactive Publication Date: 2014-07-23
KUNMING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the Hoesch reaction time of this method is long, the operation is inconvenient, and a large amount of HCl gas is required, the equipment is severely corroded, and the equipment required is relatively high, which is not conducive to large-scale production
The document Med. Chem. Res., 20, 838–846, 2011 reported that 2,4,6-trihydroxyacetophenone was used as raw material, and 2-hydroxyl-4,6- After dimethoxyacetophenone, esterification with benzoyl chloride, rearrangement into β-propanedione in an alkaline environment, cyclization under the catalysis of acetic acid / sulfuric acid mixed acid, and finally demethylation to obtain chrysin. The route of the method is long, the total yield and efficiency of the synthesis are not high, the dimethyl sulfate used is highly toxic and corrosive, the raw materials are not easy to obtain, and the price is relatively expensive, so it is not suitable for production

Method used

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[0019] The method for preparing chrysin disclosed in the present invention can be easily implemented by those skilled in the art by referring to the content of the present application. In particular, it should be pointed out that all similar replacements and modifications will be obvious to those skilled in the art. The method of the present invention is described through the following examples, and relevant personnel can obviously do it without departing from the content and spirit of the present invention. The inventive technique is implemented for the methods described herein. These similar replacements and modifications should also be placed within the claims of the patent of this application.

[0020] The concrete implementation content of this preparation chrysin is as follows:

Embodiment 1

[0022] (1) Synthesis of 2'-hydroxy-4',6'-dimethoxychalcone

[0023]

[0024] Weigh 4.2g of 1,3,5-trimethoxybenzene (0.025mol) and 3.7g of cinnamic acid (0.025mol) into a dry round bottom flask, then add 15.0mL of boron trifluoride ethyl ether, and condense at 80°C with a drying tube reflow. After reacting for 3 hours, the heating was stopped to room temperature, and red needle crystals were precipitated, and the crystals were filtered out. The crystals were added to 100 mL of ethanol aqueous solution and heated to reflux for 2.5 hours to obtain an orange-yellow clear liquid, which was decolorized and filtered by adding activated carbon. After cooling, the yellow solid was washed out, filtered, washed and dried to obtain 5.35g of 2'-hydroxy-4',6'-dimethoxychalcone, with a yield of 75.4%.

[0025] Structural parameters 1 H NMR (400 MHz, DMSO-d 6 ), δ: 3.83 (s, 3H, OCH 3 -4’), 3.91 (s, 3H, OCH 3 -6'), 6.14 (d, J = 1.6 Hz, 1H, H-3'), 6.17 (d, J = 1.6 Hz, 1H, H-5'), 7.45–...

Embodiment 2

[0035] (1) Synthesis of 2'-hydroxy-4',6'-dimethoxychalcone

[0036]

[0037] Weigh 4.2g of 1,3,5-trimethoxybenzene (0.025mol) and 5.5g of cinnamic acid (0.0375mol) into a dry round bottom flask, then add 30.0mL of boron trifluoride ether, and condense at 100°C with a drying tube reflow. After reacting for 4 hours, the heating was stopped to room temperature, and red needle-like crystals were precipitated, and the crystals were filtered out. The crystals were added to 100 mL of ethanol aqueous solution and heated to reflux for 2.5 hours to obtain an orange-yellow clear liquid, which was decolorized and filtered by adding activated carbon. After cooling, the yellow solid was washed out, filtered, washed and dried to obtain 5.79g of 2'-hydroxy-4',6'-dimethoxychalcone with a yield of 81.6%.

[0038] (2) Synthesis of 5,7-dimethoxyflavone

[0039]

[0040] Weigh 5.7g (0.02 mol) of 2'-hydroxy-4',6'-dimethoxychalcone, add 30 mL DMSO to dissolve completely, add 0.17g elemental...

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Abstract

The invention discloses a method of preparing chrysin. The method comprises the following steps: S1, synthesizing 2'-hydroxyl-4', 6'-dimethoxyl chalcone by 1, 3, 5-triethoxy benzene and cinnamic acid under catalysis of boron trifluoride diethyl etherate; S2, generating 5, 7'-dimethoxyl flavone by 2'-hydroxyl-4', 6'-dimethoxyl chalcone under catalysis of a single substance iodine; and S3, fully demethylating 5, 7'-dimethoxyl flavone to generate chrysin. The method of preparing chrysin provided by the invention improves the synthetic yield of chrysin, is few in synthetic step, low in cost, easy to control and simple to operate, and has a high industrial application prospect, and the raw materials are easily available.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for preparing chrysin. Background technique [0002] Chrysin (5,7-dihydroxy-2-phenyl-4 H -chromen-4- one ), English name chrysin, exists in the seeds and stem bark of Oroxylum indicum (L.) Vent., the heartwood of Pinus mon-ticola Dougl. In various plants such as P. aristata Engelm.), its chemical structure is shown below. [0003] [0004] Modern pharmacological studies have shown that chrysin has a wide range of pharmacological activities, such as antitumor effects (M. Cárdenas, et al., Bioorg. Med. Chem ., 2006, 14, 2966); Antiallergic effect (F. L. Pearce, et al., J. Allergy Clin. Immun ., 1984, 73, 819); anti-inflammatory effect (H. Cho, et al., . Pharmacol. Res. , 2004, 49, 37); antiviral effect (J.-H. Lee, et al., Korean Journal of Pharmacognosy. , 1999, 30, 34); anti-pathogenic microorganism effect (K. Suresh Babu, et al., Bioorg. Med. Chem. Lett ., 20...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 杨健刘漫张楫杨波韩彬
Owner KUNMING UNIV OF SCI & TECH
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