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Method for synthesizing glycitein

A synthesis method and glycidin technology are applied in the field of synthesis of glycidin and its analogs, can solve problems such as low yield, and achieve the effects of high yield, mild conditions and easy post-processing

Inactive Publication Date: 2019-03-05
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Based on the current state of the art, the inventors of the present application intend to overcome the shortcomings of the low yield of the above-mentioned route, and provide a high-yield route suitable for large-scale preparation, specifically related to the synthesis of a new glycitein and its analogues method

Method used

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  • Method for synthesizing glycitein
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  • Method for synthesizing glycitein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Synthesis of 4-methoxy-6-chloroacetyl-1,3-benzenediol

[0021]

[0022] Dissolve 5g 4-methoxy 1,3-benzenediol in 100mL boron trifluoride ether solution, add 15g chloroacetic acid, react for 12h at 65℃, quench the reaction with 200mL ice saturated sodium bicarbonate solution, and extract with ethyl acetate (250mL × 3 times), the organic phases were combined, washed with saturated sodium chloride solution (200 mL × 3 times), dried with anhydrous sodium sulfate, filtered and concentrated, separated by silica gel column, V (petroleum ether): V (ethyl acetate) = 8 :1 eluted to obtain 5.77 g of white solid with a yield of 75.8%.

[0023] m.p.139-142℃; 1 H NMR(CDCl 3 ,400MHz)δ:3.92(s,3H,-OCH 3 ); 4.59(s,2H,-CH 2 Cl); 6.38(s,1H,3'-H); 6.57(s,1H,6'-H); 7.02(s,1H, 2'-OH); 12.06(s,1H,4'-OH) .

Embodiment 2

[0024] Example 2 Synthesis of 4-methoxy-6-bromoacetyl-1,3-benzenediol

[0025]

[0026] Under nitrogen protection, add 10mL dry redistilled CH to 380mg anhydrous aluminum trichloride (2.85mmol) 2 Cl 2 , 172.8mg bromoacetyl bromide (0.856mmol) was added dropwise under ice bath conditions, after stirring for 1 hour, 100mg 4-methoxy-1,3-benzenediol (0.714mmol) in CH 2 Cl 2 The solution was 10mL, reacted at 40℃ for 4h; quenched with ice water, extracted with dichloromethane (30mL×3 times), combined the organic phases, washed with saturated sodium chloride solution (20mL×3 times), dried with anhydrous sodium sulfate, filtered Concentrate, separate by silica gel column, and elute with V (petroleum ether): V (ethyl acetate) = 10:1 to obtain 60 mg of yellow needle crystals with a yield of 32.2%.

[0027] m.p.152-153℃; ESI-MS(m / z,%):261([M+H] + ,100); 1 H NMR (CDCl 3 ,400MHz)δ:3.92(s,3H,-OCH 3 ); 4.33(s,2H,-CH 2 Br); 6.39(s, 1H,3'-H); 6.54(s,1H,6'-H); 7.06(s,1H,2'-OH); 12.11(s,1H,4'-OH) .

Embodiment 3

[0028] Example 3 Synthesis of 3-chloro-6-methoxy-7-hydroxy-4H-chromen-4-one

[0029]

[0030] 730mg of 4-methoxy-6-chloroacetyl-1,3-benzenediol (3.37mmol) was dissolved in 5mL of dry redistilled DMF, 1mL of methanesulfonyl chloride was slowly added, and the reaction was carried out at 60°C for 2h. The reaction solution was poured into 50 mL of 5% sodium acetate solution, a solid was precipitated, and 655 mg of a white solid was obtained by filtration, with a yield of 85.8%.

[0031] m.p.207-218℃; ESI-MS m / z(%)227([M+H] + ,56); 229(M+3 + ,18); 1 H NMR(CDCl 3 ,400MHz)δ:4.02(s,3H,-OCH 3) ; 6.35 (s, 1H, 7-OH); 6.94 (s, 1H, 8-H); 7.60 (s, 1H, 5-H); 8.08 (s, 1H, 2-H).

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Abstract

The invention belongs to the technical fields of organic chemistry and pharmaceutical synthesis and relates to a method for synthesizing glycitein and analogs thereof. The glycitein is 6-methoxy-4',7-dihydroxyl isoflavone. The method is performed according to a synthesis route represented by a formula shown in the description, the synthesized glycitein is 6-methoxy-4',7-dihydroxyl isoflavone or ananalog thereof; and the synthesis route of the method is high in yield, simple and convenient in operation and moderate in conditions and is adaptable to large-scale preparation.

Description

Technical field [0001] The present invention belongs to the technical field of organic chemistry and pharmaceutical synthesis, and relates to a method for synthesizing glycitein and its analogs. The glycitein is 6-methoxy-4',7-dihydroxyisoflavone. Background technique [0002] The prior art discloses that Soybean isoflavones (Soybean isoflavones) is a type of secondary metabolites formed during the growth of soybeans, etc., and is a kind of bioflavonoids, which mainly refers to the use of 3-phenylbenzopyrone as The core compound, which cannot be synthesized in the human body. Studies have shown that the said compounds have limited distribution in nature, mainly in legumes, with soybeans as the highest content, so they are called soybean isoflavones. Research reports that soy isoflavones are a kind of phytoestrogens. They have a molecular structure and molecular weight similar to estrogen. They have a two-way regulation effect on female estrogen levels. When the estrogen levels i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36
CPCC07D311/36
Inventor 张倩李涵彬
Owner FUDAN UNIV
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