CN108484374A - A kind of synthetic method of pterostilbene - Google Patents
A kind of synthetic method of pterostilbene Download PDFInfo
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- CN108484374A CN108484374A CN201810530471.1A CN201810530471A CN108484374A CN 108484374 A CN108484374 A CN 108484374A CN 201810530471 A CN201810530471 A CN 201810530471A CN 108484374 A CN108484374 A CN 108484374A
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- 0 CC(c1cc(O)cc(O)c1)=* Chemical compound CC(c1cc(O)cc(O)c1)=* 0.000 description 3
- YGRIOAJXSOQAER-FRKPEAEDSA-N COc1cc(/C(/C(O)=O)=C\c(cc2)ccc2O)cc(OC)c1 Chemical compound COc1cc(/C(/C(O)=O)=C\c(cc2)ccc2O)cc(OC)c1 YGRIOAJXSOQAER-FRKPEAEDSA-N 0.000 description 1
- UYEMGAFJOZZIFP-UHFFFAOYSA-N OC(c1cc(O)cc(O)c1)=O Chemical compound OC(c1cc(O)cc(O)c1)=O UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N Oc1ccc(C=O)cc1 Chemical compound Oc1ccc(C=O)cc1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C37/0555—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 being esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention generates 4 acetoxyl group benzaldehydes using 4 hydroxy benzaldehydes as raw material, through acetylization reaction；It is reacted again through wittig and generates 4 acetoxy-styrenes；4 acetoxy-styrenes generate 4 hydroxy styrenes through hydrolysis；Target product pterostilbene is obtained by the reaction through Heck in 4 hydroxy styrenes.This method is easy to get with raw material, and selectivity of product is high, and yield is higher, and reaction condition is mild, advantage easy to operate.
Description
Technical field
The invention belongs to synthesize field, and in particular to a kind of synthetic method of pterostilbene.
Background technology
Pterostilbene is one kind in natural extract stilbene substance, is resveratrol interior metabolism product, because finding earliest
It gains the name in red sandalwood, but in recent years, agri-scientific research office of United States Department of Agriculture (USDA-ARS) natural products research on utilization center
The scientists such as Agnes M.Rimando have found that it is also widely present in a variety of berries such as grape, blueberry and tomato.It grinds recently
Study carefully and shows it with anti-oxidant, suppressing cell reproduction, the early children grain leukemia cell HL-60 apoptosis of induction people, prevention dimethyl benzene
And skin canceration and reducing blood lipid, the hypoglycemic and antifungal activity of anthracene (DMBA) induction；Its suppressing cell reproduction and antimycotic work
Property is substantially better than resveratrol；Also there is excellent alga-lysing activity.Since it is with multiple biological activities so that its medicine,
Food, health products, cosmetics or even pesticide field are increasingly valued by people.
Pterostilbene is mainly derived from biological extraction at present, but since its biology extraction difficulty is big, of high cost and living resources
It is limited, it is difficult to meet the needs of market.Therefore chemical synthesis process becomes the most important thing, and the synthesis key of pterostilbene is two
The coupling reaction of phenyl ring, the i.e. synthesis of talan skeleton.In addition it is contemplated that the problem of cis-trans isomerism.Talan at present
The structure of skeleton mainly has Wittig (Wittig) reactions, Wittig-Horner (Wei Dihuona) reactions, Perkin (Pooles
Gold) reaction etc..
Xiao Chunfen, Sun Hongyi, Chen Yu etc., in natural product pterostilbene and (E) -3,5,3 '--4 '-hydroxyls two of trimethoxy
Synthesis [J] of styrene《Research and development of natural products》4 phases in 2010) in, it is reacted using Perkin and prepares pterostilbene.With
3,5- resacetophenones are raw material, and 3,5- dimethoxy benzene second is obtained through methylating and being reset with WillgerodtKinder
Then acid occurs Perkin with parahydroxyben-zaldehyde and vanillic aldehyde respectively and key intermediate E-2,3- diaryl third is obtained by the reaction
Olefin(e) acid, Perkin be obtained by the reaction be full Z configurations compound, isomerization occurs while decarboxylic reaction and obtains full E last decarboxylation
The target compound pterostilbene of formula.
Invention content
For existing pterostilbene synthetic method there are of high cost, yield is relatively low, and synthesis step is complicated, target product structure
Many disadvantages such as not single.Passing through side of the Heck reaction synthesis with single transconfiguration pterostilbene the present invention provides a kind of
Method.
The synthetic method of pterostilbene of the present invention generates 4- acetoxyl groups using 4- hydroxy benzaldehydes as raw material, through acetylization reaction
Benzaldehyde (2)；(2) it and is reacted through wittig (Wittig) and generates 4- acetoxy-styrenes (3)；(3) it is generated through hydrolysis
4-Vinyl phenol (4)；(4) target product (1) is obtained by the reaction through Heck (He Ke).
Specific synthetic route is as described below：
The synthetic method of pterostilbene of the present invention is as follows：
(1) synthesis of 4- acetoxyl groups benzaldehyde
Parahydroxyben-zaldehyde is added in 50mL round-bottomed flasks, 20mL dichloromethane is added and is dissolved, then adds
Acetic anhydride is finally slowly added dropwise in potassium carbonate, is detected through TLC (thin-layer chromatography) after reacting at room temperature 0.5-3h, reaction terminates.Suction filtration removes
Potassium carbonate, filtrate is gone to spin off dichloromethane through 50 DEG C of decompressions, obtain pale yellow oil matter 4- acetoxyl groups benzaldehyde (2)；
Wherein, the molar ratio of parahydroxyben-zaldehyde, potassium carbonate and acetic anhydride is：1:1-1.3:1-1.3.
(2) synthesis of 4- acetoxy-styrenes
4- acetoxyl group benzaldehydes are added in 100mL round-bottomed flasks, 50mL tetrahydrofurans are added and are dissolved, then again
Potassium carbonate is added, finally adds methyltriphenylphosphonium bromide (MTPPB), is heated to 60-80 DEG C, is detected through TLC after 12-36h,
Reaction terminates.It is cooled to room temperature, 50mL water is added, is extracted with ethyl acetate (50mL × 3), merge organic phase, use saturated common salt
Water washing (100mL × 3), is finally dried with anhydrous sodium sulfate, is spin-dried for obtaining yellow oil, column chromatography (ethyl acetate：Petroleum ether=
1:100,1L) purifying obtains pale yellow oil matter 4- acetoxy-styrenes (3)；
Wherein, the molar ratio of 4- acetoxyl groups benzaldehyde, potassium carbonate and methyltriphenylphosphonium bromide is：1：1-1.5：1-
1.5。
(3) synthesis of 4-Vinyl phenol
4- acetoxy-styrenes are added in 50mL round-bottomed flasks, 10mL methanol is added and is dissolved, is then added
20% sodium hydroxide solution detects after reacting at room temperature 0.5-2h through TLC, and reaction terminates.50mL water is added, is extracted with ethyl acetate
It takes (50mL × 3), merges organic phase and finally dried, be spin-dried for anhydrous sodium sulfate with saturated common salt water washing (100mL × 3)
To yellow oil, spontaneous curing obtains faint yellow solid 4-Vinyl phenol (4)；
Wherein, the mass volume ratio of 4- acetoxy-styrenes and sodium hydroxide is：1：8-15.
(4) synthesis of pterostilbene
4-Vinyl phenol is added in the round-bottomed flask of 50ml, 15mLDMF is added and is dissolved, then sequentially adds 3,
5- dimethoxy bromobenzenes, wet chemical (potassium carbonate is dissolved in 10mL water), tetrabutylammonium bromide, palladium, triphenylphosphine add
Heat is reacted to 100-140 DEG C, is detected through TLC after 6-12h, reaction terminates.It is cooled to room temperature, suction filtered through kieselguhr, filtrate acetic acid
Ethyl ester (50mL × 3) extracts, and merges organic phase, and organic phase (200mL × 6), anhydrous sodium sulfate drying, mistake are washed with saturated brine
Filter, filtrate obtain reddish black oil, column chromatography (ethyl acetate through 50 DEG C of evaporated under reduced pressure：Petroleum ether=1:20,2.5L) purifying obtains white
Color solid powder pterostilbene.
Wherein, 4-Vinyl phenol, 3,5- dimethoxy bromobenzenes, potassium carbonate, tetrabutylammonium bromide, palladium and triphenyl
The molar ratio of phosphine is 1：1.2-1.5：2-2.5：0.05-0.15:0.04-0.06:0.1-0.15.
Pterostilbene produced by the present invention has the early young grain leukemia cell HL-60 of anti-oxidant, suppressing cell reproduction, induction people
Apoptosis prevents skin canceration and reducing blood lipid, hypoglycemic and antifungal activity that dimethylbenzanthracene (DMBA) induces；Due to
It can be used for medicine, food, health products, cosmetics or even pesticide field with multiple biological activities.
Advantageous effect
The present invention has synthesized the expensive intermediate 4-Vinyl phenol needed for Heck reactions with starting material cheap and easy to get,
The limitation application that Heck reactions need expensive intermediate is broken.There is higher anti diastereoselectivity using Heck reactions,
Higher yield, and reaction condition is mild, simple operation and other advantages, uses Heck reactions as crucial alkene coupling step for the first time
Suddenly, the pterostilbene of single anti-configuration is obtained.With preferable development prospect.
Specific implementation mode
Embodiment 1
(1) 2 synthesis
Parahydroxyben-zaldehyde (2.0g (gram), 16.38mmol (mM)) is added in 50mL (milliliter) round-bottomed flask, so
20mL dichloromethane is added afterwards to be dissolved, then adds potassium carbonate (2.5g, 18.00mmol), acetic acid is finally slowly added dropwise
Acid anhydride (1.8mL, 18.00mmol), room temperature reaction 2h (hour) are detected by TLC (thin-layer chromatography), and reaction terminates.It filters and removes carbon elimination
Sour potassium, filtrate spin off dichloromethane through 50 DEG C of decompressions, obtain pale yellow oil matter 4- acetoxyl groups benzaldehyde (2) 2.6g, yield
96.73%.1H NMR(400MHz,CDCl3)δ：2.34 (s, 3H), 7.28 (d, J=8.0Hz, 2H), 7.92 (d, J=12.0Hz,
2H),9.99(s,1H)。
(2) 3 synthesis
4- acetoxyl groups benzaldehyde (2.0g, 12.18mmol) is added in 100mL round-bottomed flasks, 50mL tetra- is then added
Hydrogen furans is dissolved, and is then added potassium carbonate (1.9g, 13.75mmol), is finally added methyltriphenylphosphonium bromide
(4.8g, 13.44mmol) heats 70 DEG C (degree Celsius), is detected afterwards through TLC for 24 hours, reaction terminates.It is cooled to room temperature, 50mL is added
Water is extracted with ethyl acetate (50mL × 3), merges organic phase, with saturated common salt water washing (100mL × 3), finally with anhydrous sulphur
Sour sodium drying, is spin-dried for obtaining yellow oil 2.6g, column chromatography (ethyl acetate：Petroleum ether=1:100,1L) purifying obtains faint yellow oil
Shape substance；4- acetoxy-styrenes (3) 1.2g, yield 60.91%.1H NMR(400MHz,CDCl3)δ：2.23(s,3H),
6.17 (dd, J=12.0Hz, 1H), 5.63 (dd, J=24.0Hz, 1H), 6.63 (m, 1H), 6.97 (d, J=12.0Hz, 2H),
7.34 (d, J=12.0Hz, 2H).
(3) 4 synthesis
4- acetoxy-styrenes (1.0g, 6.17mmol) are added in 50mL round-bottomed flasks, 10mL methanol is then added
It is dissolved, 20% sodium hydroxide solution of 10mL is then added, detected through TLC after reacting at room temperature 0.5h, reaction terminates.It is added
50mL water is extracted with ethyl acetate (50mL × 3), merges organic phase and finally uses nothing with saturated common salt water washing (100mL × 3)
Aqueous sodium persulfate is dried, and is spin-dried for obtaining yellow oil, spontaneous curing obtains faint yellow solid 4-Vinyl phenol (4) 0.7g, yield
94.59%.1H NMR(400MHz,DMSO)δ：6.04 (d, J=16.0Hz, 1H), 6.58 (d, J=20.0Hz, 1H), 6.60
(m, 1H), 6.72 (d, J=12.0Hz, 2H), 7.28 (d, J=8.0Hz, 2H), 9.54 (s, 1H).
(4) 1 synthesis
4-Vinyl phenol (0.5g, 4.16mmol) is added in the round-bottomed flask of 50ml, 15mLDMF is added its is molten
Solution, then sequentially adds 3,5- dimethoxys bromobenzene (1.3g, 5.99mmol), wet chemical (1.3g is dissolved in 10mL water),
Tetrabutylammonium bromide (134.2mg, 0.42mmol), palladium (46.7mg, 0.21mmol), triphenylphosphine (131.0mg,
0.50mmol), 120 DEG C of reactions are heated to, are detected through TLC after 8h, reaction terminates.It is cooled to room temperature, suction filtered through kieselguhr, filtrate is used
Ethyl acetate (50mL × 3) extracts, and merges organic phase, washs organic phase (200mL × 6) with saturated brine, anhydrous sodium sulfate is dry
Dry, filtering, filtrate obtains reddish black oil 1.6g, column chromatography (ethyl acetate through 50 DEG C of evaporated under reduced pressure：Petroleum ether=1:20,2.5L) pure
Change obtains white solid powder 0.6g, yield 56.23%.1H NMR(400MHz,DMSO)δ：3.77 (s, 6H), 6.38 (t,
1H), 6.72 (s, 2H), 6.78 (d, 2H), 6.95 (d, J=20.0Hz, 2H), 7.16 (d, J=20.0Hz, 2H), 7.4 (d, J=
8.0Hz,2H)。
Embodiment 2
The molar ratio of hydroxy benzaldehyde in step (1), potassium carbonate and acetic anhydride is：1:1.3:1.3, reaction time 3h are received
Rate 95.82%.
The molar ratio of 4- acetoxyl group benzaldehydes in step (2), potassium carbonate and methyltriphenylphosphonium bromide is：1：1.3：
1.3,80 DEG C, reaction time 30h of reaction temperature, yield 58.66%
The mass volume ratio of 4- acetoxy-styrenes and sodium hydroxide is in step (3)：1：12, reaction time 1h are received
Rate 94.55%
4-Vinyl phenol in step (4), 3,5- dimethoxy bromobenzenes, potassium carbonate, tetrabutylammonium bromide, palladium and three
The molar ratio of Phenylphosphine is 1：1.2：2.4：0.05:0.04:0.1, reaction time 10h, 110 DEG C of reaction temperature, yield 55.33%
Embodiment 3
The molar ratio of hydroxy benzaldehyde in step (1), potassium carbonate and acetic anhydride is：1:1:1, reaction time 2.5h, yield
94.68%.
The molar ratio of 4- acetoxyl group benzaldehydes in step (2), potassium carbonate and methyltriphenylphosphonium bromide is：1：1：1, instead
Answer 66 DEG C, reaction time 25h of temperature, yield 53.78%.
The mass volume ratio of 4- acetoxy-styrenes and sodium hydroxide is in step (3)：1：8, reaction time 1.5h are received
Rate 93.88%.
4-Vinyl phenol in step (4), 3,5- dimethoxy bromobenzenes, potassium carbonate, tetrabutylammonium bromide, palladium and three
The molar ratio of Phenylphosphine is 1：1.5：2.1：0.12:0.06:0.15.Reaction time 12h, 130 DEG C of reaction temperature, yield
53.72%.
Claims (7)
1. a kind of synthetic method of pterostilbene, it is characterised in that：The synthetic method is：
(1) using 4- hydroxy benzaldehydes as raw material, 4- acetoxyl group benzaldehydes are generated through acetylization reaction；
(2) 4- acetoxyl groups benzaldehyde is reacted through wittig generates 4- acetoxy-styrenes；
(3) 4- acetoxy-styrenes generate 4-Vinyl phenol through hydrolysis；
(4) target product pterostilbene is obtained by the reaction through Heck in 4-Vinyl phenol.
2. the synthetic method of pterostilbene as described in claim 1, it is characterised in that：The synthetic method is：
(1) 4- acetoxyl group benzaldehydes are synthesized
4- hydroxy benzaldehydes are added in round-bottomed flask, dichloromethane is added and is dissolved, then adds potassium carbonate, finally delays
It is slow that acetic anhydride is added dropwise, it is detected through TLC after room temperature reaction, reaction terminates, and filters and removes potassium carbonate, and filtrate spins off two through 50 DEG C of decompressions
Chloromethanes obtains pale yellow oil matter 4- acetoxyl group benzaldehydes；
(2) 4- acetoxy-styrenes are synthesized
4- acetoxyl group benzaldehydes are added in round-bottomed flask, tetrahydrofuran is added and is dissolved, then adds potassium carbonate, most
After be added methyltriphenylphosphonium bromide, detected through TLC after heating reaction, reaction terminates, and is cooled to room temperature, and 50mL water is added, and uses
Ethyl acetate extracts, and merges organic phase and is finally dried with anhydrous sodium sulfate with saturated common salt water washing, is spin-dried for obtaining yellow oil,
Column chromatography purifies to obtain pale yellow oil matter 4- acetoxy-styrenes；
(3) 4-Vinyl phenol is synthesized
4- acetoxy-styrenes are added in round-bottomed flask, methanol is added and is dissolved, 20% sodium hydroxide is then added
Solution detects after room temperature reaction through TLC, and reaction terminates, and 50mL water is added, is extracted with ethyl acetate, and merges organic phase, with saturation
Brine It is dried with anhydrous sodium sulfate, is spin-dried for obtaining yellow oil, spontaneous curing obtains faint yellow solid 4-Vinyl phenol；
(4) pterostilbene is synthesized
4-Vinyl phenol is added in round-bottomed flask, DMF is added and is dissolved, 3,5- Brolamfetamines are then sequentially added
Benzene, wet chemical, tetrabutylammonium bromide, palladium, triphenylphosphine detect after heating reaction through TLC, and reaction terminates, cold
But to room temperature, suction filtered through kieselguhr, filtrate is extracted with ethyl acetate, and merges organic phase, organic phase, anhydrous sulphur are washed with saturated brine
Sour sodium drying, filtering, filtrate obtain reddish black oil through 50 DEG C of evaporated under reduced pressure, and column chromatography purifies to obtain white solid powder pterostilbene.
3. the synthetic method of pterostilbene as claimed in claim 2, it is characterised in that：Step (1) described parahydroxyben-zaldehyde, carbon
The molar ratio of sour potassium and acetic anhydride is：1:1.0-1.3:1.0-1.3 the reaction time is：0.5-3h.
4. the synthetic method of pterostilbene as claimed in claim 2, it is characterised in that：Step (2) the 4- acetyloxy phenyls first
The molar ratio of aldehyde, potassium carbonate and methyltriphenylphosphonium bromide is：1:1.0-1.5：1.0-1.5 reaction temperature is：60-80 DEG C, instead
It is between seasonable：12-36h.
5. the synthetic method of pterostilbene as claimed in claim 2, it is characterised in that：Step (3) the 4- acetoxyl groups ethylene
Mass volume ratio with sodium hydroxide solution is：1:8-15, reaction time is：0.5-2h.
6. the synthetic method of pterostilbene as claimed in claim 2, it is characterised in that：Step (4) described 4-Vinyl phenol, 3,
The molar ratio of 5- dimethoxy bromobenzenes, potassium carbonate, tetrabutylammonium bromide, palladium and triphenylphosphine is 1:1.2-1.5:2-2.5:
0.05-0.15:0.04-0.06:0.1-0.15, reaction temperature are：100-140 DEG C, the reaction time is：6-12h.
7. a kind of application of the pterostilbene of method synthesis as claimed in claim 2, it is characterised in that：The pterostilbene is for curing
Medicine, food, health products, cosmetics and pesticide field.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056927A (en) * | 2019-12-10 | 2020-04-24 | 清华大学 | Method for synthesizing monosubstituted styrene |
| CN116813454A (en) * | 2023-06-21 | 2023-09-29 | 珠海市柏瑞医药科技有限公司 | Synthetic method of pterostilbene |
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| US5763560A (en) * | 1994-12-05 | 1998-06-09 | Honshu Chemical Industry Co., Ltd. | Method of producing styrene derivatives |
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2018
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| US5763560A (en) * | 1994-12-05 | 1998-06-09 | Honshu Chemical Industry Co., Ltd. | Method of producing styrene derivatives |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056927A (en) * | 2019-12-10 | 2020-04-24 | 清华大学 | Method for synthesizing monosubstituted styrene |
| CN116813454A (en) * | 2023-06-21 | 2023-09-29 | 珠海市柏瑞医药科技有限公司 | Synthetic method of pterostilbene |
| CN116813454B (en) * | 2023-06-21 | 2024-03-22 | 珠海市柏瑞医药科技有限公司 | Synthetic method of pterostilbene |
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Application publication date: 20180904 |
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