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Synthetic method for natural product 2,3',4,5'-tetrahydroxy bibenzyl

A technology of natural products and synthetic methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of unrecyclable catalysts, poor atom economy, high cost, etc. Economical and easy to operate

Active Publication Date: 2017-04-05
GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Regarding the synthesis of 2,3',4,5'-tetrahydroxybibenzyl compounds, it is generally reported in the literature that E-2,3 ', 4,5'-tetrahydroxystilbene, and then prepare 2,3',4,5'-tetrahydroxybibenzyl by hydrogenation reaction, but these methods have long reaction steps, high cost, catalyst cannot be recycled, intermediate However, the body needs to be protected and deprotected, the atom economy is poor, and it is difficult to prepare on a large scale.

Method used

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  • Synthetic method for natural product 2,3',4,5'-tetrahydroxy bibenzyl
  • Synthetic method for natural product 2,3',4,5'-tetrahydroxy bibenzyl
  • Synthetic method for natural product 2,3',4,5'-tetrahydroxy bibenzyl

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Experimental program
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Effect test

Embodiment 1

[0029] (1) Preparation of 3-(3,5-dihydroxyphenyl)-7-hydroxycoumarin

[0030] To a round bottom flask was added 3,5-dihydroxyphenylacetic acid (2.52 g, 15 mmol), 2,4-dihydroxybenzaldehyde (2.07 g, 15 mmol), triethylamine (4.55 g, 45 mmol), acetic anhydride (10 mL ), stirred, heated to 110° C. in an oil bath, and reacted for 7 hours. After the reaction is complete, pour the reaction solution into 50 mL of ice water while it is hot, stir, and solids precipitate out, filter with suction, wash the filter cake with water, collect the filter cake, dissolve the filter cake with aqueous sodium hydroxide solution, wash with ethyl acetate, and acidify with hydrochloric acid When pH=3~4, a solid is precipitated, suction filtered, washed with water, the filter cake is collected, dried to obtain a light yellow solid, which is 3-(3,5-dihydroxyphenyl)-7-hydroxycoumarin, weight 3.24g , yield 80%.

[0031] (2) Preparation of E-2,3',4,5'-tetrahydroxystilbene

[0032] Put 3-(3,5-dihydroxypheny...

Embodiment 2

[0036] (1) Preparation of 3-(3,5-dihydroxyphenyl)-7-hydroxycoumarin

[0037] To a round bottom flask was added 3,5-dihydroxyphenylacetic acid (2.52 g, 15 mmol), 2,4-dihydroxybenzaldehyde (2.07 g, 15 mmol), triethylamine (4.55 g, 45 mmol), propionic anhydride (10 mL ), stirred, heated to 110° C. in an oil bath, and reacted for 7 hours. After the reaction is complete, pour the reaction solution into 50 mL of ice water while it is hot, stir, and solids precipitate out, filter with suction, wash the filter cake with water, collect the filter cake, dissolve the filter cake with aqueous sodium hydroxide solution, wash with ethyl acetate, and acidify with hydrochloric acid When pH=3~4, a solid is precipitated, suction filtered, washed with water, the filter cake is collected, dried to obtain a light yellow solid, which is 3-(3,5-dihydroxyphenyl)-7-hydroxycoumarin, weight 2.75g , yield 68%.

[0038] (2) Preparation of E-2,3',4,5'-tetrahydroxystilbene

[0039] Put 3-(3,5-dihydroxyph...

Embodiment 3

[0043] (1) Preparation of 3-(3,5-dihydroxyphenyl)-7-hydroxycoumarin

[0044] To a round bottom flask was added 3,5-dihydroxyphenylacetic acid (2.52 g, 15 mmol), 2,4-dihydroxybenzaldehyde (2.07 g, 15 mmol), triethylamine (4.55 g, 45 mmol), acetic anhydride (10 mL ), stirred, heated to 110° C. in an oil bath, and reacted for 9 hours. After the reaction is complete, pour the reaction solution into 50 mL of ice water while it is hot, stir, and solids precipitate out, filter with suction, wash the filter cake with water, collect the filter cake, dissolve the filter cake with aqueous sodium hydroxide solution, wash with ethyl acetate, and acidify with hydrochloric acid When pH=3~4, a solid is precipitated, suction filtered, washed with water, the filter cake is collected, dried to obtain a light yellow solid, which is 3-(3,5-dihydroxyphenyl)-7-hydroxycoumarin, weight 2.87g , yield 71%.

[0045] (2) Preparation of E-2,3',4,5'-tetrahydroxystilbene

[0046] Put 3-(3,5-dihydroxypheny...

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Abstract

The invention discloses a synthetic method for a natural product 2,3',4,5'-tetrahydroxy bibenzyl. The synthetic method comprises the following steps that 3,5-dyhydroxy phenylacetic acid and 2,4-dyhydroxy benzaldehyde serve as materials and conduct a condensation reaction in the presence of alkali to obtain 3-(3,5-dyhydroxy phenyl)-7-hydroxy coumarin; then a ring opening decarboxylation reaction is conducted under an alkaline condition, and E-2,3',4,5'-tetrahydroxy toluylene is obtained; and finally a hydrogenation reaction is conducted to obtain the natural product 2,3',4,5'-tetrahydroxy bibenzyl. According to the synthetic method, the materials are easy to obtain, the reaction route is simple, atom economy is high, post-treatment is succinct, and productivity is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing natural product 2,3',4,5'-tetrahydroxybibenzyl. Background technique [0002] 2,3',4,5'-Tetrahydroxybibenzyl is a natural product (Pholdota) isolated from plants of the genus Pholidota, and it is also found in Caryophyllaceae plant species. It is a natural product E - Hydrogenated derivatives of 2,3',4,5'-tetrahydroxystilbene. 2,3',4,5'-Tetrahydroxybibenzyl has strong tyrosinase inhibitory activity and antioxidant activity, and studies have also found that it can act as a γ-aminobutyric acid type A receptor Modulator (Nat.Prod.Rep.2009,26,916; Nat.Prod.Rep.2012,29; J.Nat.Prod.2012,752261; J.Phytochemistry 2008,69,1084; Bioorg.Med.Chem.2014, 22,1276–1284; Bioorg.Med.Chem.Lett.2006,16,5650–5653), therefore, 2,3',4,5'-tetrahydroxybibenzyl is expected to be effective in anticonvulsant, antihypertensive and headache , gastroenteritis, and bronchitis are wi...

Claims

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Application Information

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IPC IPC(8): C07C37/00C07C39/16
CPCC07C37/003C07C37/0555C07D311/16
Inventor 邹永盛剑飞黄熙华
Owner GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK
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