CN105418381A - Oxyresveratrol synthesis method - Google Patents
Oxyresveratrol synthesis method Download PDFInfo
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- CN105418381A CN105418381A CN201510882156.1A CN201510882156A CN105418381A CN 105418381 A CN105418381 A CN 105418381A CN 201510882156 A CN201510882156 A CN 201510882156A CN 105418381 A CN105418381 A CN 105418381A
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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Abstract
The invention provides an oxyresveratrol synthesis method which comprises the following steps: firstly performing a reflux reaction between raw materials 3,5-dimethoxybenzyl alcohol and phosphorus oxychloride; after the reaction is complete, pressurizing and recycling the solvent; filtering, washing to neutrality and drying to obtain 3,5-dimethoxybenzyl chloride; performing a reflux reaction between the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite in a solvent DMF (dimethyl formamide); after the reaction is complete, adding a catalyst sodium methylate solution, and adding a mixed solution of 2,4-dimethoxy benzaldehyde and DMF to obtain tetramethoxy diphenyl ethylene; and finally, performing a reflux reaction between the obtained tetramethoxy diphenyl ethylene and aluminum trichloride and xylene, wherein oxyresveratrol is obtained after the reaction is complete. According to the method provided by the invention, a Witting-Homer reaction is adopted, the raw materials are easily available, the yield is high, the cost is low, and the method is suitable for industrial production.
Description
Technical field
The present invention relates to medicinal chemistry art, be specifically related to a kind of synthetic method of oxidized resveratrol.
Background technology
Oxidized resveratrol, English name: Oxyresveratrol, chemistry 4-[(E)-2-(3,5-dihydroxy phenyl) vinyl] benzene-1,3-glycol by name.Oxidized resveratrol is a kind of derivative of poly-hydroxy trans stilbene class natural product resveratrol, natural compounds trans stilbene class material has the multiple colleges and universities biological activitys such as anticancer effect, has outstanding curative effect to diseases such as Cardiovarscular, virus infection, diabetes, central nervous system disorder, fat-reducing, anti-inflammatories.Oxidized resveratrol is a kind of effective tyrosine kinase inhibitors; in addition also there is very strong skin pigmentation effect; and the effect of herpes, antiviral, anti-oxidant, neuroprotective and cerebral ischemia inhibited apoptosis when occurring; in addition, oxidized resveratrol also has whitening, hepatoprotective effect.
In recent years, oxidized resveratrol is the most promising compound with the functional foodstuff of multiple pharmacological effect for research and development to have scholar to point out, and pharmacokinetic display oxidized resveratrol is by can aldose acidifying rapidly after oral absorption, to be discharged by urine or other non-kidney circuits excrete.This shows that oxidized resveratrol is as oral medicine or relevant food safety and hypotoxicity.Along with modernization development, new preparation technique and the raising of research and development ability, the natural phant of oxidized resveratrol and glucoside carries out furtheing investigate and just seems especially valuable with researching and developing, no matter be at medicine or at field of food, the R&D and production of oxidized resveratrol and glucoside thereof has great importance.The structural formula of oxidized resveratrol is as follows:
Up to the present, in various plants, find the existence of oxidized resveratrol, as having report in mulberry leaf, Punetree, numb rattan, Jack-fruit, black false hellebore containing oxidized resveratrol.Fewer about the report extracting oxidized resveratrol in plant, the method of the separation of oxidized resveratrol from ramulus mori has been delivered as Tong Zhiyuan, Yan Xinpei etc., ethanol extraction method is adopted to obtain ramulus mori crude extract, be separated by silicagel column, dextran post column chromatography and prepare ramulus mori oxidized resveratrol sample, but not to yield report, its technological process is also too complicated.Because plant is generally on the low side at the content of oxidized resveratrol, plant resources reduces gradually, and a kind of method developing chemosynthesis is prepared its product and had greater significance.
The Sun Hongyi of Guangzhou institute of the Chinese Academy of Sciences etc. are with 3,5-resacetophenone (1) is raw material, through to methylate and Willgerodt-Kindler rearrangement reaction obtains 3,5-dimethoxyphenylacetic acid (3), 3,5-dimethoxyphenylacetic acid (3) and 2,4-dimethoxy benzaldehyde (4) builds toluylene skeleton through Perkin reaction, obtain target product oxidized resveratrol (7) through decarboxylation and demethylation isomerization reaction again, total recovery is 30%.High and the market of this method raw material 3,5-resacetophenone price is without bulk production supply, and in decarboxylic reaction process, temperature higher strip part is harsh, and aftertreatment is difficult to operation.Reimann is with 3; 5-bis-(trimethylsiloxy group) methyl benzoate is starting raw material; 3 are obtained through reduction and deprotection; 5-dihydroxy-benzyl alcohol; Wittig reagent is prepared again after bromination, the protection of benzene hydroxy esterification; and then react to obtain oxidized resveratrol with 2,4-bis-(trimethylsiloxy group) phenyl aldehyde through Wittig.There is the shortcomings such as complex steps, expensive starting materials, severe reaction conditions and yield be low equally in this synthetic method.
Summary of the invention
Problem to be solved by this invention is that a kind of yield is high, raw material is easy to get and is applicable to the new synthetic method of the oxidized resveratrol of suitability for industrialized production.
The technical scheme solved the problem: the synthetic method of the oxidized resveratrol provided, comprises the following steps:
Step 1: by raw material 3,5-3,5-dimethoxybenzoic alcohol and phosphorus oxychloride back flow reaction, question response pressurizes recycling design completely afterwards, filters, is washed to neutrality, after drying 3,5-dimethoxy-benzyl chloride;
Step 2: by 3,5-dimethoxy-benzyl chlorides of gained and trimethyl phosphite in solvent DMF back flow reaction, question response completely after add catalyst sodium methoxide solution, then add the mixing solutions of 2,4-dimethoxy benzaldehyde and DMF, obtain tetramethoxy toluylene;
Step 3: the tetramethoxy toluylene of gained, aluminum trichloride (anhydrous) and refluxing xylene are reacted, after question response is complete, obtains oxidized resveratrol.
Above-mentioned steps 1 is specifically: by the phosphorus oxychloride back flow reaction of raw material 3,5-3,5-dimethoxybenzoic alcohol and 3-5 times amount, question response completely after, pressurization recycling design, to 1/3 of original volume, is cooled to 0-5 DEG C, agitation and filtration, be washed to neutrality, drying under reduced pressure obtains 3,5-dimethoxy-benzyl chloride.
Above-mentioned steps 2 is specifically: by 3 of step 1 gained, 5-dimethoxy-benzyl chloride and trimethyl phosphite, in solvent DMF back flow reaction, adopt TLC to detect, and adding mass concentration after question response is complete is 28% catalyst sodium methoxide solution, add 2 again, the mixing solutions of 4-dimethoxy benzaldehyde and DMF, the completely rear concentrated solvent of question response, to 1/2nd of original volume, adds water and methyl alcohol stirring, filter, be washed to neutral crude product, refining methanol, obtains tetramethoxy toluylene;
The mol ratio of above-mentioned 3,5-dimethoxy-benzyl chlorides and trimethyl phosphite is 1:1-1.2; The mass ratio of described 3,5-dimethoxy-benzyl chlorides and solvent DMF is 1:2-5; The mass ratio of described 3,5-dimethoxy-benzyl chlorides and sodium methylate is 1:0.5-1.5; The mol ratio of described 3,5-dimethoxy-benzyl chlorides and 2,4-dimethoxy benzaldehyde is 1:1-1.2; In described mixing solutions, the mass ratio of 2,4-dimethoxy benzaldehydes and DMF is 1.5-2.5:1.
Above-mentioned steps 3 is specifically: the tetramethoxy toluylene of step 2 gained, aluminum trichloride (anhydrous) and refluxing xylene are reacted, question response completely after pour in frozen water, add ethyl acetate, layering organic layer is washed, drying obtains brown crude product, and refining methanol obtains oxidized resveratrol; Described tetramethoxy toluylene, aluminum trichloride (anhydrous) and xylene mass are than being 1:4-6:5-10.
Advantage of the present invention:
The present invention reacts through Wittig-Homer, and raw material is easy to get, and yield is high, and cost is low, is applicable to suitability for industrialized production simultaneously.
Embodiment
Embodiment 1
1, the preparation of 3,5-dimethoxy-benzyl chlorides
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5 3,5-dimethoxybenzoic alcohol 42g, phosphorus oxychloride 126ml, temperature rising reflux, about 2h, TLC detects, and raw material primitive reaction is complete, and pressurization recycling design to 1/3 is cooled to 0-5 DEG C, slowly drip water 150ml, add, stirring at room temperature 2h, filter, washing is neutral, and drying under reduced pressure obtains white solid 45g, yield 96.7%.
2, the preparation of tetramethoxy toluylene
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5-dimethoxy-benzyl chloride 37.2g, trimethyl phosphite 27g, DMF80ml, temperature rising reflux reaction 4.5h, TLC detect, and raw material 3,5-dimethoxy-benzyl chloride disappears.Be cooled to 5-10 DEG C, drip the sodium methoxide solution 29.8g of 28%, drip off and keep this temperature to stir 2h, drip the solution that 2,4-dimethoxy benzaldehyde 36.5g+20mlDMF is made into, drip off room temperature reaction 3h, the solvent of concentration and recovery 1/2nd, add water 200ml, methyl alcohol 50ml, stirs 2h, filter, crude product 75g, 80ml refining methanol after washing is neutral, obtains white solid 51.4g after drying.Yield 63.4%.
3, the preparation of oxidized resveratrol
Under room temperature, in dry 500ml tetra-mouthfuls reaction, drop into tetramethoxy toluylene 28.5g, aluminum trichloride (anhydrous) 114g, dimethylbenzene 160g, slowly temperature rising reflux, after 8h, TLC detects, and reacts complete.Be cooled to room temperature, pour in frozen water, add ethyl acetate 40ml, layering organic layer is washed, and drying obtains brown crude product, the refining methanol of 10%, obtains white solid 11.3g yield 59.8%.
Embodiment 2
1, the preparation of 3,5-dimethoxy-benzyl chlorides
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5 3,5-dimethoxybenzoic alcohol 42g, phosphorus oxychloride 150ml, temperature rising reflux, about 2h, TLC detects, and raw material primitive reaction is complete, and pressurization recycling design to 1/3 is cooled to 0-5 DEG C, slowly drip water 180ml, add, stirring at room temperature 2h, filter, washing is neutral, and drying under reduced pressure obtains white solid 42.5g, yield 91.3%.
2, the preparation of tetramethoxy toluylene
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5-dimethoxy-benzyl chloride 37.2g, trimethyl phosphite 26g, DMF120ml, temperature rising reflux reaction 4h, TLC detect, and raw material 3,5-dimethoxy-benzyl chloride disappears.Be cooled to 5-10 DEG C, drip the sodium methoxide solution 30g of 28%, drip off and keep this temperature to stir 2h, drip the solution that 2,4-dimethoxy benzaldehyde 35g+20mlDMF is made into, drip off room temperature reaction 3h, the solvent of concentration and recovery 1/2nd, add water 200ml, methyl alcohol 50ml, stirs 2h, filter, crude product 73g, 75ml refining methanol after washing is neutral, obtains white solid 50.8g after drying.Yield 62.6%.
3, the preparation of oxidized resveratrol
Under room temperature, in dry 500ml tetra-mouthfuls reaction, drop into tetramethoxy toluylene 28.5g, aluminum trichloride (anhydrous) 128g, dimethylbenzene 180g, slowly temperature rising reflux, after 8h, TLC detects, and reacts complete.Be cooled to room temperature, pour in frozen water, add ethyl acetate 40ml, layering organic layer is washed, and drying obtains brown crude product, the refining methanol of 10%, obtains white solid 11.3g yield 66.1%.
Embodiment 3
1, the preparation of 3,5-dimethoxy-benzyl chlorides
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5 3,5-dimethoxybenzoic alcohol 42g, phosphorus oxychloride 175ml, temperature rising reflux, about 4h, TLC detects, and raw material primitive reaction is complete, and pressurization recycling design to 1/3 is cooled to 0-5 DEG C, slowly drip water 200ml, add, stirring at room temperature 2h, filter, washing is neutral, and drying under reduced pressure obtains white solid 43.0g, yield 93.6%.
2, the preparation of tetramethoxy toluylene
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5-dimethoxy-benzyl chloride 37.2g, trimethyl phosphite 35g, DMF90ml, temperature rising reflux reaction 2.5h, TLC detect, and raw material 3,5-dimethoxy-benzyl chloride disappears.Be cooled to 5-10 DEG C, drip the sodium methoxide solution 44g of 28%, drip off and keep this temperature to stir 2h, drip the solution that 2,4-dimethoxy benzaldehyde 40g+20mlDMF is made into, drip off room temperature reaction 4h, the solvent of concentration and recovery 1/2nd, add water 250ml, methyl alcohol 60ml, stirs 2h, filter, crude product 79.6g, 80ml refining methanol after washing is neutral, obtains white solid 54.6g after drying.Yield 67.3%.
3, the preparation of oxidized resveratrol
Under room temperature, in dry 500ml tetra-mouthfuls reaction, drop into tetramethoxy toluylene 28.5g, aluminum trichloride (anhydrous) 135g, dimethylbenzene 200g, slowly temperature rising reflux, after 8h, TLC detects, and reacts complete.Be cooled to room temperature, pour in frozen water, add ethyl acetate 50ml, layering organic layer is washed, and drying obtains brown crude product, the refining methanol of 10%, obtains white solid 10.8g yield 63.2%.
Embodiment 4
1, the preparation of 3,5-dimethoxy-benzyl chlorides
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5 3,5-dimethoxybenzoic alcohol 42g, phosphorus oxychloride 200ml, temperature rising reflux, about 3h, TLC detects, and raw material primitive reaction is complete, and pressurization recycling design to 1/3 is cooled to 0-5 DEG C, slowly drip water 200ml, add, stirring at room temperature 2h, filter, washing is neutral, and drying under reduced pressure obtains white solid 42.6g, yield 92.7%.
2, the preparation of tetramethoxy toluylene
In dry 500ml tetra-mouthfuls of reaction flasks, drop into 3,5-dimethoxy-benzyl chloride 37.2g, trimethyl phosphite 37g, DMF100ml, temperature rising reflux reaction 2.5h, TLC detect, and raw material 3,5-dimethoxy-benzyl chloride disappears.Be cooled to 5-10 DEG C, drip the sodium methoxide solution 44g of 28%, drip off and keep this temperature to stir 2h, drip the solution that 2,4-dimethoxy benzaldehyde 42g+20mlDMF is made into, drip off room temperature reaction 4h, the solvent of concentration and recovery 1/2nd, add water 200ml, methyl alcohol 60ml, stirs 2h, filter, crude product 80.2g, 80ml refining methanol after washing is neutral, obtains white solid 53.3g after drying.Yield 65.8%.
3, the preparation of oxidized resveratrol
Under room temperature, in dry 500ml tetra-mouthfuls reaction, drop into tetramethoxy toluylene 28.5g, aluminum trichloride (anhydrous) 135g, dimethylbenzene 250g, slowly temperature rising reflux, after 9h, TLC detects, and reacts complete.Be cooled to room temperature, pour in frozen water, add ethyl acetate 50ml, layering organic layer is washed, and drying obtains brown crude product, the refining methanol of 10%, obtains white solid 9.3g yield 54.4%.
Claims (4)
1. a synthetic method for oxidized resveratrol, is characterized in that, comprises the following steps:
Step 1: by raw material 3,5-3,5-dimethoxybenzoic alcohol and phosphorus oxychloride back flow reaction, question response pressurizes recycling design completely afterwards, filters, is washed to neutrality, after drying 3,5-dimethoxy-benzyl chloride;
Step 2: by 3,5-dimethoxy-benzyl chlorides of gained and trimethyl phosphite in solvent DMF back flow reaction, question response completely after add catalyst sodium methoxide solution, then add the mixing solutions of 2,4-dimethoxy benzaldehyde and DMF, obtain tetramethoxy toluylene;
Step 3: the tetramethoxy toluylene of gained, aluminum trichloride (anhydrous) and refluxing xylene are reacted, after question response is complete, obtains oxidized resveratrol.
2. the synthetic method of oxidized resveratrol according to claim 1, it is characterized in that, described step 1 is specifically: by the phosphorus oxychloride back flow reaction of raw material 3,5-3,5-dimethoxybenzoic alcohol and 3-5 times amount, question response completely after, pressurization recycling design is to 1/3 of original volume, be cooled to 0-5 DEG C, agitation and filtration, be washed to neutrality, drying under reduced pressure obtains 3,5-dimethoxy-benzyl chloride.
3. the synthetic method of oxidized resveratrol according to claim 1, it is characterized in that, described step 2 is specifically: by 3 of step 1 gained, 5-dimethoxy-benzyl chloride and trimethyl phosphite are in solvent DMF back flow reaction, TLC is adopted to detect, adding mass concentration after question response is complete is 28% catalyst sodium methoxide solution, add 2 again, the mixing solutions of 4-dimethoxy benzaldehyde and DMF, the completely rear concentrated solvent of question response is to 1/2nd of original volume, add water and methyl alcohol stirring, filter, be washed to neutral crude product, refining methanol, obtain tetramethoxy toluylene,
The mol ratio of described 3,5-dimethoxy-benzyl chlorides and trimethyl phosphite is 1:1-1.2; The mass ratio of described 3,5-dimethoxy-benzyl chlorides and solvent DMF is 1:2-5; The mass ratio of described 3,5-dimethoxy-benzyl chlorides and sodium methylate is 1:0.5-1.5; The mol ratio of described 3,5-dimethoxy-benzyl chlorides and 2,4-dimethoxy benzaldehyde is 1:1-1.2; In described mixing solutions, the mass ratio of 2,4-dimethoxy benzaldehydes and DMF is 1.5-2.5:1.
4. the synthetic method of oxidized resveratrol according to claim 1, it is characterized in that, described step 3 is specifically: the tetramethoxy toluylene of step 2 gained, aluminum trichloride (anhydrous) and refluxing xylene are reacted, pour in frozen water after question response is complete, add ethyl acetate, layering organic layer is washed, and drying obtains brown crude product, refining methanol, obtains oxidized resveratrol; Described tetramethoxy toluylene, aluminum trichloride (anhydrous) and xylene mass are than being 1:4-6:5-10.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018118059A1 (en) * | 2016-12-22 | 2018-06-28 | Muhammed Majeed | Novel method for extraction of oxyresveratrol from artocarpus hirsutus |
| CN108752168A (en) * | 2018-07-17 | 2018-11-06 | 上海华堇生物技术有限责任公司 | A kind of new preparation process of oxidation Stilbene triphenol |
| CN109970517A (en) * | 2019-04-28 | 2019-07-05 | 杭州瑞树生化有限公司 | A kind of preparation method of resveratrol compounds |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018118059A1 (en) * | 2016-12-22 | 2018-06-28 | Muhammed Majeed | Novel method for extraction of oxyresveratrol from artocarpus hirsutus |
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| CN109970517A (en) * | 2019-04-28 | 2019-07-05 | 杭州瑞树生化有限公司 | A kind of preparation method of resveratrol compounds |
| CN109970517B (en) * | 2019-04-28 | 2021-09-17 | 杭州师范大学 | Preparation method of resveratrol compound |
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Application publication date: 20160323 |