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Method for synthesizing trans-stilbene compound under assistance of microwave

A technology for stilbene and microwave synthesis, applied in the field of chemical industry, can solve the problems of expensive metal catalysts, low atom economy, harsh reaction conditions, etc., and achieve the effects of short reaction time, convenient post-processing and high yield

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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Harsh reaction conditions, expensive metal catalysts, low atom economy and other disadvantages limit the application of the above methods

Method used

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  • Method for synthesizing trans-stilbene compound under assistance of microwave
  • Method for synthesizing trans-stilbene compound under assistance of microwave
  • Method for synthesizing trans-stilbene compound under assistance of microwave

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of 3,3',4,4',5,5'-hexamethoxytrans-stilbene comprises the following steps:

[0023] Titanium tetrachloride (1.09 ml, 10 mmol) was added dropwise to a mixture of zinc powder (1.30 g, 20 mmol) and tetrahydrofuran (20 ml) under ice-cooling. After the dropwise addition, 3,4,5-trimethoxybenzaldehyde (1.96 g, 10 mmol) was added to the above mixture, and stirred at room temperature for 1 hour. The above reaction system was refluxed in a microwave reactor for 10 minutes (65°C). TLC was used to detect the progress of the reaction. After the reaction was completed, it was filtered. A large amount of dilute hydrochloric acid was added to the filtrate to precipitate a solid, which was filtered by suction and dried. The solid was recrystallized with chloroform-ethanol to obtain White solid 3,3',4,4',5,5'-hexamethoxytrans-stilbene 1.53g, yield 85%.

[0024] The characterization data of the product are: 1 H NMR (400MHz, DMSO-d 6 )δ:ppm 7.15(s,2H),6.89(s,4H),3.82(s,1...

Embodiment 2

[0027] The preparation of 4,4'-dihydroxy-3,3',5,5'-tetramethoxytrans-stilbene comprises the following steps:

[0028] Titanium tetrachloride (1.32ml, 15mmol) was added dropwise to a mixture of zinc powder (1.95g, 30mmol) and tetrahydrofuran (20ml) under ice-cooling. After the dropwise addition, 4′-hydroxy-3,5,-dimethoxybenzaldehyde (1.82 g, 10 mmol) was added to the above mixture, and stirred at room temperature for 1 hour. The above reaction system was refluxed in a microwave reactor for 10 minutes (65°C). TLC was used to detect the progress of the reaction. After the reaction was completed, it was filtered. A large amount of dilute hydrochloric acid was added to the filtrate to precipitate a solid, which was filtered by suction and dried. The solid was recrystallized with chloroform-ethanol to obtain White solid 4,4'-dihydroxy-3,3',5,5'-tetramethoxytrans-stilbene 1.36g, yield 82%.

[0029] The characterization data of the product are: 1 H NMR (400MHz, DMSO-d 6 )δ:ppm 8.45...

Embodiment 3

[0032] The preparation of 3,3',5,5'-tetramethoxy trans-stilbene comprises the following steps:

[0033] Titanium tetrachloride (1.31 ml, 12 mmol) was added dropwise to a mixture of zinc powder (3.90 g, 60 mmol) and tetrahydrofuran (20 ml) under an ice bath. After the dropwise addition, 3,5-dimethoxybenzaldehyde (1.66 g, 10 mmol) was added to the above mixture, and stirred at room temperature for 1 hour. The above reaction system was refluxed in a microwave reactor for 15 minutes (65°C), and the progress of the reaction was detected by TLC. After the reaction was completed, it was filtered, and a large amount of dilute hydrochloric acid was added to the filtrate to precipitate a solid, which was filtered by suction and dried. The solid was recrystallized with chloroform-ethanol to obtain White solid 3,3',5,5'-tetramethoxytrans-stilbene 1.31g, yield 87%.

[0034] The characterization data of the product are: 1 H NMR (400MHz, DMSO-d 6 )δ:ppm 7.20(s,2H),6.77(d,J=2.0Hz,4H),6.40(...

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Abstract

The invention discloses a method for synthesizing a trans-stilbene compound under the assistance of microwave. The method comprises the following steps of dropwise adding titanium tetrachloride into a mixture of zinc powder and an organic solvent under the ice bath condition, adding a benzaldehyde compound (a formula 2 shown in the specification) into the reaction system after dropwise adding of titanium tetrachloride, stirring for 1 hour at room temperate, and carrying out refluxing reaction on the reaction system in a microwave reactor to generate the trans-stilbene compound (a formula 1 shown in the specification). The method provided by the invention has the advantages of short reaction time, convenience in after-treatment and high yield. According to the method, catalysis by a precious metal and strict anhydrous operation are omitted, and thus the method is easy and convenient to operate and facilitates large-scale production.

Description

technical field [0001] The invention belongs to the field of chemistry and chemical engineering, and in particular relates to a method for microwave-assisted synthesis of trans-stilbenes by using benzaldehyde as a raw material. Background technique [0002] Trans-stilbenes are an important class of organic compounds, and related structures are widely found in natural products and bioactive molecules. For example: resveratrol, whose chemical name is 3,4′,5-trihydroxy-trans-stilbene, is widely found in grapes, knotweed, cassia, peanuts and other plants, and has the functions of lowering blood fat, anti-platelet aggregation, Antioxidant, anti-free radical, antibacterial and anti-inflammatory, anti-osteoporosis and other biological activities (Chemical Reagent, 2011, 33(12), 1141-1143). The chemical name of picatanol is 3,3′,4,5′-tetrahydroxy-trans-stilbene, which is a kind of polyphenols, which widely exists in grapes, blueberries, and sugarcane. Oxidation, anti-cell prolifer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/215C07C43/23C07C39/21C07C41/30C07C37/20
CPCC07B37/00C07C37/20C07C41/30C07C43/215C07C43/23C07C39/21
Inventor 张恩生邹永徐田龙王德建魏文
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