Synthesis method of pterostilbene

A synthesis method and technology of pterostilbene are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve the problems of non-single structure of target products, complex synthesis steps and high cost, and achieve good development prospects and simple operation. , the effect of mild reaction conditions

Inactive Publication Date: 2018-09-04
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are many shortcomings in the existing synthetic method of pterostilbene, such as high cost, low yield, complicated synthetic steps, and not single structure of the target product.

Method used

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  • Synthesis method of pterostilbene
  • Synthesis method of pterostilbene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Synthesis of 2

[0028] Add p-hydroxybenzaldehyde (2.0g (gram), 16.38mmol (mmol)) to a 50mL (milliliter) round bottom flask, then add 20mL of dichloromethane to dissolve it, and then add potassium carbonate (2.5g, 18.00mmol ), and finally acetic anhydride (1.8mL, 18.00mmol) was slowly added dropwise, and after 2h (hour) reaction at room temperature, it was detected by TLC (thin layer chromatography), and the reaction was completed. Potassium carbonate was removed by suction filtration, and dichloromethane was spun off from the filtrate under reduced pressure at 50°C to obtain 2.6 g of light yellow oily substance 4-acetoxybenzaldehyde (2), with a yield of 96.73%. 1 H NMR (400MHz, CDCl 3 ) δ: 2.34 (s, 3H), 7.28 (d, J=8.0Hz, 2H), 7.92 (d, J=12.0Hz, 2H), 9.99 (s, 1H).

[0029] (2) Synthesis of 3

[0030] Add 4-acetoxybenzaldehyde (2.0g, 12.18mmol) in a 100mL round bottom flask, then add 50mL tetrahydrofuran to dissolve it, then add potassium carbonate (1.9g, 13.75mmo...

Embodiment 2

[0036] In the step (1), the molar ratio of hydroxybenzaldehyde, potassium carbonate and acetic anhydride is 1:1.3:1.3, the reaction time is 3 hours, and the yield is 95.82%.

[0037] In step (2), the molar ratio of 4-acetoxybenzaldehyde, potassium carbonate and methyl triphenylphosphine bromide is: 1:1.3:1.3, the reaction temperature is 80°C, the reaction time is 30h, and the yield is 58.66%

[0038] The mass volume ratio of 4-acetoxystyrene to sodium hydroxide in step (3) is: 1:12, the reaction time is 1h, and the yield is 94.55%

[0039] In step (4), the molar ratio of 4-hydroxystyrene, 3,5-dimethoxybromobenzene, potassium carbonate, tetrabutylammonium bromide, palladium acetate and triphenylphosphine is 1:1.2:2.4:0.05 :0.04:0.1, reaction time 10h, reaction temperature 110°C, yield 55.33%

Embodiment 3

[0041] In step (1), the molar ratio of hydroxybenzaldehyde, potassium carbonate and acetic anhydride is 1:1:1, the reaction time is 2.5 hours, and the yield is 94.68%.

[0042] In step (2), the molar ratio of 4-acetoxybenzaldehyde, potassium carbonate and methyltriphenylphosphine bromide is 1:1:1, the reaction temperature is 66° C., the reaction time is 25 hours, and the yield is 53.78%.

[0043] In step (3), the mass volume ratio of 4-acetoxystyrene to sodium hydroxide is 1:8, the reaction time is 1.5 h, and the yield is 93.88%.

[0044] In step (4), the molar ratio of 4-hydroxystyrene, 3,5-dimethoxybromobenzene, potassium carbonate, tetrabutylammonium bromide, palladium acetate and triphenylphosphine is 1:1.5:2.1:0.12 :0.06:0.15. The reaction time was 12 hours, the reaction temperature was 130°C, and the yield was 53.72%.

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Abstract

The invention provides a synthesis method of pterostilbene. The synthesis method takes 4-hydroxybenzaldehyde as a raw material and comprises the following steps: carrying out acetylation reaction to generate 4-acetoxybenzaldehyde; then carrying out wittig reaction to generate 4-acetoxystyrene; carrying out hydrolysis reaction on 4-acetoxystyrene to generate 4-hydroxystyrene; carrying out Heck reaction on 4-hydroxystyrene to obtain a target product pterostilbene. The method provided by the invention has the advantages of easiness for obtaining the raw materials, high product selectivity, relatively high yield, moderate reaction conditions and simplicity in operation.

Description

technical field [0001] The invention belongs to the field of synthesis, and in particular relates to a synthesis method of pterostilbene. Background technique [0002] Pterostilbene is one of the natural extracts of stilbenes. It is a metabolite of resveratrol in the body. It is named after it was first discovered in red sandalwood. Scientists such as Agnes M. Rimando of the Research Center have found that it is also widely present in various berries such as grapes, blueberries and tomatoes. Recent studies have shown that it has anti-oxidation, anti-cell proliferation, induction of human promyelocytic anti-leukemia cell HL-60 apoptosis, prevention of skin cancer induced by dimethylbenzanthracene (DMBA), and hypolipidemic, hypoglycemic and anti-inflammatory effects. Fungal activity; its anti-cell proliferation and anti-fungal activity are significantly better than resveratrol; it also has excellent algicidal activity. Because of its various biological activities, it has att...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/30C07C67/08C07C67/293C07C69/157C07C37/055C07C39/20
CPCC07C37/0555C07C41/30C07C67/08C07C67/293C07C69/157C07C39/20C07C43/23
Inventor 任杰闫雪龙胡昆常蒙恩
Owner CHANGZHOU UNIV
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