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Method for preparing trans polyhydroxystilbene compounds

A technology of polyhydroxystilbene and dihydroxyphenylacetic acid, which is applied in the field of preparation of trans polyhydroxystilbene compounds, can solve the problems of difficult separation, cumbersome steps, and few synthesis studies, and achieve good atom economy, Simple post-processing, less environmental pollution

Inactive Publication Date: 2013-08-07
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, there are relatively few studies on the synthesis of such compounds, and literature reports generally use Wittig reaction (J Med Chem, 2003, 46: 3546-3554; Tetrahedron Lett, 1970, 47: 4051-4053), Wittig-Hornor reaction (Chin Chem Lett, 2000, 11(3): 217-218; China Food Additives, 2007, 3: 54-56) and Knoevenagel condensation ([P]CN: 200310111885.4, 2003-10-27.) to construct the stilbene skeleton
When synthesizing the target compound, these methods either require hydroxyl protection and deprotection, or group transformation, and are easy to obtain cis-trans mixtures, which are difficult to separate, require further transformation, and the steps are cumbersome

Method used

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  • Method for preparing trans polyhydroxystilbene compounds
  • Method for preparing trans polyhydroxystilbene compounds
  • Method for preparing trans polyhydroxystilbene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Take 29.4g (0.1mol) of 3,5-dibromophenylacetic acid, 40g (1mol) of NaOH, CuSO 4 .5H 2 O25.0g (0.1mol), add H 2 080ml in a 250ml stainless steel reactor equipped with a thermometer and a reflux condenser, under nitrogen protection, stirred and heated at 110°C for 72 hours, cooled the reaction solution with suction and filtered, acidified the filtrate with hydrochloric acid to adjust the pH to 4-5, extracted with ethyl acetate, and separated the organic layer, dried, and concentrated under reduced pressure to obtain crude product 3,5-dihydroxyphenylacetic acid 15.1g, yield 90%; MS m / z: 168 (M + ).

[0040] (2) Weigh 1.68g (10mmol) of 3,5-dihydroxyphenylacetic acid, 1.46g (12mmol) of 4-hydroxybenzaldehyde and add in the there-necked flask equipped with a thermometer and a reflux condenser, then add 3.03g of triethylamine ( 30mmol), 6.12g (60mmol) of acetic anhydride, refluxed at 120°C for 6 hours, after the reaction was complete, cooled the reaction solution and pou...

Embodiment 2

[0045] (1) Take 29.4g (0.1mol) of 3,5-dibromophenylacetic acid, 48g (1.2mol) of NaOH, CuSO 4 16.0g (0.1mol), add H 2 O100ml is placed in a 250ml stainless steel reactor equipped with a thermometer and a reflux condenser. Under nitrogen protection, stir and heat at 110°C for 70 hours. layer, dried, and concentrated under reduced pressure to obtain 15.6 g of crude product 3,5-dihydroxyphenylacetic acid, with a yield of 93%.

[0046] (2) Weigh 1.68g (10mmol) of 3,5-dihydroxyphenylacetic acid, 1.52g (10mmol) of 3-methoxy-4-hydroxybenzaldehyde and add it into a three-necked flask equipped with a thermometer and a reflux condenser, and then add 2.53g (25mmol) of triethylamine, 3.06g (30mmol) of acetic anhydride, refluxed at 110°C for 8 hours. After the reaction was complete, the reaction solution was cooled and poured into water to stir, and a large amount of solids were precipitated. The cake was dried and then recrystallized to obtain 3.42 g of E-2-(3,5-diacetoxyphenyl)-3-(3'-m...

Embodiment 3

[0051] (1) Take 29.4g (0.1mol) of 3,5-dibromophenylacetic acid, KOH56g (1mol), CuSO 4 .5H 2 O25.0g (0.1mol), add H 2 O150ml is placed in a 250ml stainless steel reactor equipped with a thermometer and a reflux condenser. Under nitrogen protection, stir and heat at 120°C for 60 hours. layer, dried, and concentrated under reduced pressure to obtain crude product 3,5-dihydroxyphenylacetic acid 15.8g, yield 94%;

[0052] (2) Weigh 1.68g (10mmol) of 3,5-dihydroxyphenylacetic acid and 1.38g (10mmol) of 3,4-dihydroxybenzaldehyde into a three-necked flask equipped with a thermometer and a reflux condenser, and then add triethylamine 4.04g (40mmol), 6.12g (60mmol) of acetic anhydride, reflux at 115°C for 7 hours. After the reaction is complete, cool the reaction solution and pour it into water to stir. A large amount of solids are precipitated. After standing for a while, suction filter and dry the filter cake After recrystallization, 3.60 g of E-2-(3,5-diacetoxyphenyl)-3-(3',4'-dia...

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Abstract

The invention discloses a method for preparing trans polyhydroxystilbene compounds. The method comprises the following steps: 3,5-dibromophenylacetic acid is converted into 3,5-dihydroxyphenyl acetic acid under alkali conditions;3,5-dihydroxyphenyl acetic acid and 4-hydroxybenzaldehyde compounds are subject to a Perkin reaction to obtain E-2-(3,5-diacetyl phenyl)-3-(4'-acetoxyl phenyl)acrylic acid compounds; and the E-2-(3,5-diacetyl phenyl)-3-(4'- acetoxyl phenyl)acrylic acid compounds are subject to decarboxylation isomerization and hydrolysis reaction, or hydrolysis and decarboxylation isomerization reaction to obtain the trans polyhydroxystilbene compounds. The all-trans products obtained by using the method have the advantages of favorable atom economy, simple synthetic route, simpleaftertreatment, low cost, high yield and the like, and can easily realize large-scale preparation.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of trans polyhydroxy stilbenes. Background technique [0002] Trans-polyhydroxy stilbenes (structure shown in Formula 1) are a class of compounds with important pharmacological activities. [0003] [0004] where R 1 , R 2 = H, OH or OCH 3 . [0005] Representative compounds in trans polyhydroxy stilbenes are resveratrol (Resveratrol, E-3, 4', 5-trihydroxy stilbene), Piceatannol (E-3, 3', 4', 5-tetrahydroxystilbene) and iso-Rhapontigenin (iso-Rhapontigenin, E-3,4',5-trihydroxy-3'-methoxystilbene), etc. Resveratrol widely exists in many foods (such as mulberries, peanuts and grapes, etc.), and has anti-cancer, anti-cancer, hypolipidemic, anti-thrombotic, antioxidant and anti-inflammatory effects (Inter J Biochem & Cell Biol, 2005, 37: 1709 -172; J Med Chem, 2003, 46: 3546-3554); Resveratrol can also activate Sirtuins enzymes, thereby delaying the agin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/23C07C41/26C07C41/18C07C37/50C07C39/21C07C37/055
Inventor 邹永肖春芬陈煜魏文孙洪宜吕泽良
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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