CN108675918B - Synthesis method of piceatannol - Google Patents

Synthesis method of piceatannol Download PDF

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CN108675918B
CN108675918B CN201810530492.3A CN201810530492A CN108675918B CN 108675918 B CN108675918 B CN 108675918B CN 201810530492 A CN201810530492 A CN 201810530492A CN 108675918 B CN108675918 B CN 108675918B
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piceatannol
methoxystyrene
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任杰
闫雪龙
胡昆
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Changzhou University
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Abstract

The invention takes 3-hydroxy-4-methoxybenzaldehyde as an initial raw material, 3-hydroxy-4-methoxystyrene is generated through wittig reaction, 3-hydroxy-4-methoxystyrene and 3, 5-dimethoxybromobenzene are subjected to Heck reaction to obtain E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene, and the E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene is subjected to demethylation to obtain a target product piceatannol. The Heck reaction is adopted as the construction of the stilbene parent nucleus, the target product with single configuration can be obtained, the starting raw materials are cheap and easy to obtain, the operation is simple, the condition is mild, and the yield is high.

Description

Synthesis method of piceatannol
Technical Field
The invention belongs to the field of synthesis, and particularly relates to a method for synthesizing piceatannol.
Background
Piceatannol is one of stilbene substances of natural extracts, is a 3-position hydroxylated analog of resveratrol, and is found in plants such as grapes, blueberries, passion fruits, sugarcanes and the like. Pharmacological research shows that piceatannol has many pharmacological activities, such as anticancer, cell proliferation resisting, anti-inflammatory, immunoregulation, lipid oxidation resisting, and antibacterial. Studies have shown that piceatannol is also a good antioxidant and cardiovascular protectant. With the development of the method, piceatannol is widely applied and accepted in the fields of health care products, cosmetics, medicines and the like.
At present, piceatannol is mainly derived from plant extraction. The method has the advantages of high cost, environmental friendliness and low yield. Therefore, the research of artificial synthesis becomes the focus of attention in the world today. The key point of the synthesis of piceatannol is the coupling reaction of two benzene rings, namely the synthesis of a stilbene skeleton. In addition, the problem of cis-trans isomerism is also considered. At present, the construction of a stilbene skeleton mainly comprises a Wittig (Wittig) reaction, a Wittig-Horner (Wittig-Horner) reaction, a Perkin (Purkin) reaction and the like.
The research methods for the chemical synthesis of piceatannol are few, and the synthesis of piceatannol is mainly carried out by utilizing a Wittig-Horne reaction in 5 th 2011 of fine chemical industry [ J ]:
Figure BDA0001676472510000021
the synthetic route has expensive starting materials and uses toxic substance PBr in the synthetic process3Hydrogen bromide and phosphorous acid are formed by violent reaction in water, which releases irritant vapor and causes corrosive burns. Vapors and liquids can severely irritate the eyes, mucous membranes, skin and respiratory system, causing burns, and frequent inhalation of low concentration vapors can damage the respiratory tract. And has the defects of complex post-treatment, low yield and the like. Therefore, it is important to find a simple synthetic method.
Disclosure of Invention
The method aims to overcome the defects that in the existing method for obtaining piceatannol, biological extraction cannot meet market requirements easily, cost is high, environment is not friendly, yield is low, chemical synthesis operation is complex, post-treatment is difficult, and the structure of a target product is not single.
The invention uses cheap and easily obtained starting raw materials to complete the construction of the stilbene parent nucleus through Heck reaction, thereby obtaining the piceatannol with single trans-configuration and having better development prospect.
3-hydroxy-4-methoxybenzaldehyde (2) is used as an initial raw material, and is subjected to wittig (wittig) reaction to generate 3-hydroxy-4-methoxystyrene (3), (3) and 3, 5-dimethoxybromobenzene are subjected to Heck (Heck) reaction to obtain E-3-hydroxy-3 ', 4, 5' -trimethoxystilbene (4), and (4) is subjected to demethylation to obtain a target product (1).
The synthetic route is as follows:
Figure BDA0001676472510000031
the specific synthesis process comprises the following steps:
(1) synthesis of 3-hydroxy-4-methoxystyrene
Adding 3-hydroxy-4-methoxybenzaldehyde into a round-bottom flask, adding 50mL of tetrahydrofuran to dissolve the 3-hydroxy-4-methoxybenzaldehyde, then adding potassium tert-butoxide, finally adding methyl triphenyl phosphonium bromide, heating to react, detecting by TLC, finishing the reaction, cooling to room temperature, adding 50mL of water, extracting with ethyl acetate (50mL × 3), combining organic phases, washing with saturated saline solution (100mL × 3), finally drying with anhydrous sodium sulfate, carrying out spin drying to obtain yellow oil, and purifying by column chromatography (ethyl acetate: petroleum ether: 1:30, 1L) to obtain a white solid substance, namely 3-hydroxy-4-methoxystyrene (3).
Wherein the molar ratio of the 3-hydroxy-4-methoxybenzaldehyde to the potassium tert-butoxide to the methyl triphenyl phosphonium bromide is as follows: 1: 2.0-4.0: 2.0-4.0, reaction temperature: 60-80 ℃, reaction time: 5-8 h.
(2) Synthesis of E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene
Adding 3-hydroxy-4-methoxystyrene into a round-bottom flask, adding 15mL of mixed solution of styrene and 3, 5-dimethoxybromobenzene, potassium carbonate aqueous solution (1.0g dissolved in 10mL of water), tetrabutylammonium bromide, palladium acetate and triphenylphosphine, heating, reacting, detecting by TLC, cooling to room temperature, filtering with diatomite, extracting the filtrate with ethyl acetate (50mL × 3) and combining organic phases, washing the organic phase with saturated saline (200mL × 6), drying with anhydrous sodium sulfate, filtering, evaporating the filtrate at 50 ℃ under reduced pressure to obtain yellow oil, and purifying by column chromatography (ethyl acetate: petroleum ether ═ 1:20, 2.5L) to obtain white solid powder E-3-hydroxy-3 ', 4, 5' -trimethoxy diphenylethylene.
Wherein, the mol ratio of the 3-hydroxy-4-methoxy styrene, the 3, 5-dimethoxy bromobenzene, the potassium carbonate, the tetrabutyl ammonium bromide, the palladium acetate and the triphenylphosphine is as follows: 1:1.1-1.6:1.8-2.4:0.05-0.15:0.03-0.08:0.08-0.15, reaction temperature is as follows: 100 ℃ and 140 ℃, and the reaction time is 5-10 h.
(3) Synthesis of piceatannol
Preheating a round-bottom flask to 100 ℃, adding pyridine hydrochloride, heating to 180 ℃, adding E-3-hydroxy-3 ', 4, 5' -trimethoxystilbene after dissolving the pyridine hydrochloride, heating for reaction, detecting by TLC (thin layer chromatography), cooling to room temperature, adding 30mL of water, extracting by ethyl acetate (50mL × 3), combining organic phases, washing by saturated saline (100mL × 3), drying by anhydrous sodium sulfate, carrying out decompression spin-drying on the filtrate at 50 ℃ to obtain dark black oil, and purifying by column chromatography (methanol: dichloromethane is 1:20, 1.5L) to obtain gray solid piceatannol.
Wherein, the molar ratio of the pyridine hydrochloride to the E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene is as follows: 50-80: 1, the reaction temperature is: 180 ℃ and 260 ℃, the reaction time is as follows: 0.5-1.5 h.
Piceatannol has anticancer, anti-cell proliferation, antiinflammatory, immunoregulatory, lipid oxidation resisting, and antibacterial effects. Studies have shown that piceatannol is also a good antioxidant and cardiovascular protectant. The piceatannol synthesized by the invention can be used in the fields of health care products, cosmetics, medicines and the like.
Advantageous effects
The invention utilizes the advantages of Heck reaction, such as higher trans-stereoselectivity, higher yield, mild reaction condition, simple operation and the like, and uses the Heck reaction as the key olefin coupling step for the first time to obtain the piceatannol with single trans-configuration. Has better development prospect. The preparation method reduces production cost; the yield is improved; obtaining a single E-configuration target product.
Detailed Description
Example 1
(1) Synthesis of 3-hydroxy-4-methoxystyrene
A100 mL round bottom flask was charged with 3-hydroxy-4-methoxybenzaldehyde (2.0g, 13.14mmol), dissolved in 50mL tetrahydrofuran, added with potassium tert-butoxide (4.4g, 39.21mmol), added with methyl triphenyl phosphonium bromide (12.7g, 35.55mmol), heated at 70 deg.C for 7h, checked by TLC, and invertedAfter completion, the reaction mixture was cooled to room temperature, 50mL of water was added, extracted with ethyl acetate (50mL of × 3), the organic phases were combined, washed with saturated brine (100mL of × 3), dried over anhydrous sodium sulfate, and spin-dried to obtain 2.6g of a yellow oil, which was purified by column chromatography (ethyl acetate: petroleum ether ═ 1:30, 1L) to obtain 1.2g of 3-hydroxy-4-methoxystyrene as a white solid with a yield of 60.91%.1H NMR(300MHz,CDCl3)δ：3.77(s,3H),5.08(d,J＝12.0Hz,1H),5.66(d,J＝18.0Hz,1H),6.68(dd,J＝18.0and12.0Hz,1H),6.88(m,3H),9.00(s,1H)。
(2) Synthesis of E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene
3-hydroxy-4-methoxystyrene (0.5g, 3.33mmol) was added to a 50mL round bottom flask, and 15mL of DMF was added to dissolve it, then 3, 5-dimethoxybromobenzene (1.0g, 4.61mmol), aqueous potassium carbonate (1.0g, dissolved in 10mL of water), tetrabutylammonium bromide (107.3mg, 0.33mmol), palladium acetate (37.4mg, 0.17mmol), triphenylphosphine (104.8mg, 0.40mmol) were added in that order, heated to 120 ℃ for reaction, detected by TLC after 8h, the reaction was terminated, cooled to room temperature, filtered through celite and suction, the filtrate was extracted with ethyl acetate (50mL × 3), the organic phases were combined, the organic phase was washed with saturated brine (200mL × 6), dried over anhydrous sodium sulfate, filtered, the filtrate was evaporated to dryness at 50 ℃ to obtain 1.6g of yellow oil, and column chromatography was performed (ethyl acetate: petroleum ether 1:20, 2.5L) to obtain white solid powder with a yield of 63.16%.1H NMR(400MHz,CDCl3)δ：3.78(s,9H),6.38(t,1H),6.73(d,2H),6.93(m,2H),7.04(m,2H),7.13(d,J＝15.0Hz,1H),9.03(s,1H)。
(3) Synthesis of piceatannol
50mL of a round-bottomed flask was first preheated to 100 ℃ and then pyridine hydrochloride (5g, 43.27mmol) was added, heated to 180 ℃ and after the pyridine hydrochloride had dissolved, E-3-hydroxy-3 ', 4, 5' -trimethoxystilbene (0.2g, 0.70mmol) was added, the temperature was raised to 240 ℃ and the reaction was terminated by TLC after 1 hour, cooled to room temperature, 30mL of water was added, extracted with ethyl acetate (50mL × 3), the organic phases were combined, washed with saturated brine (100mL × 3), finally dried over anhydrous sodium sulfate, the filtrate was spin-dried under reduced pressure at 50 ℃ to give 230mg of a dark black oil, column chromatography (methanol:dichloromethane ═ 1:20, 1.5L) to afford 92mg of a grey solid in 53.93% yield.1H NMR(400MHz,CDCl3)δ：6.10(t,1H),6.36(d,2H),6.68(d,J＝16.0Hz,1H),6.72(d,1H),6.82(d,1H),6.86(m,1H),6.96(d,1H),8.93(s,1H),9.10(s,1H),9.19(s,2H)。
Example 2
In the step (1), the molar ratio of the 3-hydroxy-4-methoxybenzaldehyde, the potassium tert-butoxide and the methyl triphenyl phosphonium bromide is as follows: 1: 2.5: 2.5, reaction temperature: 75 ℃, reaction time: and 6 h.
In the step (2), the molar ratio of the 3-hydroxy-4-methoxystyrene, the 3, 5-dimethoxybromobenzene, the potassium carbonate, the tetrabutylammonium bromide, the palladium acetate and the triphenylphosphine is as follows: 1:1.2:2.0:0.08:0.06:0.08, reaction temperature: the reaction time was 6.5h at 110 ℃.
The molar ratio of the pyridine hydrochloride to the E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene in the step (3) is as follows: 60: 1, the reaction temperature is: the reaction time is as follows at 200 ℃: and (5) h.
Example 3
In the step (1), the molar ratio of the 3-hydroxy-4-methoxybenzaldehyde, the potassium tert-butoxide and the methyl triphenyl phosphonium bromide is as follows: 1: 3.5: 3.5, reaction temperature: 80 ℃, reaction time: and 8 h.
In the step (2), the molar ratio of the 3-hydroxy-4-methoxystyrene, the 3, 5-dimethoxybromobenzene, the potassium carbonate, the tetrabutylammonium bromide, the palladium acetate and the triphenylphosphine is as follows: 1:1.5:2.2:0.12:0.08:0.1, reaction temperature: the reaction time was 9h at 130 ℃.
The molar ratio of the pyridine hydrochloride to the E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene in the step (3) is as follows: 80: 1, the reaction temperature is: the reaction time is as follows at 260 ℃: 0.5 h.

Claims (2)

1. A synthetic method of piceatannol is characterized in that: the synthesis method comprises the following specific steps:
(1) synthesis of 3-hydroxy-4-methoxystyrene
Adding 3-hydroxy-4-methoxybenzaldehyde into a round-bottom flask, adding tetrahydrofuran to dissolve the 3-hydroxy-4-methoxybenzaldehyde, then adding potassium tert-butoxide, finally adding methyl triphenyl phosphonium bromide, heating for reaction, detecting by TLC, cooling to room temperature, adding 50mL of water, extracting with ethyl acetate, combining organic phases, washing with saturated saline solution, finally drying with anhydrous sodium sulfate, spin-drying to obtain yellow oil, and purifying by column chromatography to obtain a white solid substance, namely 3-hydroxy-4-methoxystyrene;
the molar ratio of the 3-hydroxy-4-methoxybenzaldehyde, potassium tert-butoxide and methyl triphenyl phosphonium bromide is as follows: 1: 2.0-4.0: 2.0-4.0, reaction temperature: 60-80 ℃, reaction time: 5-8 h;
(2) synthesis of E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene
Adding 3-hydroxy-4-methoxystyrene into a round-bottom flask, adding DMF (dimethyl formamide) to dissolve the 3-hydroxy-4-methoxystyrene, then sequentially adding 3, 5-dimethoxybromobenzene, a potassium carbonate aqueous solution, tetrabutylammonium bromide, palladium acetate and triphenylphosphine, carrying out heating reaction, detecting by TLC (thin layer chromatography), finishing the reaction, cooling to room temperature, carrying out suction filtration on kieselguhr, extracting a filtrate by using ethyl acetate, combining organic phases, washing the organic phase by using saturated saline, drying by using anhydrous sodium sulfate, filtering, evaporating the filtrate at 50 ℃ under reduced pressure to obtain yellow oil, and carrying out column chromatography purification to obtain white solid powder E-3-hydroxy-3 ', 4, 5' -trimethoxystilbene;
the molar ratio of the 3-hydroxy-4-methoxystyrene to the 3, 5-dimethoxybromobenzene to the potassium carbonate to the tetrabutylammonium bromide to the palladium acetate to the triphenylphosphine is as follows: 1:1.1-1.6:1.8-2.4:0.05-0.15:0.03-0.08: 0.08-0.15; the reaction temperature is as follows: 100 ℃ and 140 ℃, and the reaction time is 5-10 h;
(3) synthesis of piceatannol
Preheating a round-bottom flask to 100 ℃, adding pyridine hydrochloride, heating to 180 ℃, adding E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene after dissolving the pyridine hydrochloride, detecting by TLC after heating reaction, cooling to room temperature, adding 30mL of water, extracting by ethyl acetate, combining organic phases, washing by saturated saline solution, drying by anhydrous sodium sulfate, drying the filtrate by decompression and spin-drying at 50 ℃ to obtain dark black oil, and purifying by column chromatography to obtain gray solid piceatannol.
2. The method of synthesizing piceatannol as claimed in claim 1, wherein: the molar ratio of the pyridine hydrochloride to the E-3-hydroxy-3 ', 4, 5' -trimethoxy stilbene in the step (3) is as follows: 50-80: 1, the reaction temperature is: 180 ℃ and 260 ℃, the reaction time is as follows: 0.5-1.5 h.
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CN101085743A (en) * 2006-06-06 2007-12-12 浙江大德药业集团有限公司 Fluorine-containing alkoxy combretastatin derivative, preparation method and use thereof
CN103214354A (en) * 2013-04-28 2013-07-24 上海大学 Preparation method of trans-stilbene compound and water-soluble derivative of compound
CN105439824A (en) * 2015-11-06 2016-03-30 陕西嘉禾生物科技股份有限公司 Synthesis method of piceatannol

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101085743A (en) * 2006-06-06 2007-12-12 浙江大德药业集团有限公司 Fluorine-containing alkoxy combretastatin derivative, preparation method and use thereof
CN103214354A (en) * 2013-04-28 2013-07-24 上海大学 Preparation method of trans-stilbene compound and water-soluble derivative of compound
CN105439824A (en) * 2015-11-06 2016-03-30 陕西嘉禾生物科技股份有限公司 Synthesis method of piceatannol

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