CN104387246A - Preparation method of 3'-hydroxypterostilbene - Google Patents
Preparation method of 3'-hydroxypterostilbene Download PDFInfo
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- CN104387246A CN104387246A CN201410632546.9A CN201410632546A CN104387246A CN 104387246 A CN104387246 A CN 104387246A CN 201410632546 A CN201410632546 A CN 201410632546A CN 104387246 A CN104387246 A CN 104387246A
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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
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
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Abstract
The invention belongs to the technical field of chemical synthesis and discloses a preparation method of 3'-hydroxypterostilbene. The preparation method comprises the following steps: adding pterostilbene and an oxidant 2-iodoxybenzoic acid to an organic solvent, stirring for reacting at a room temperature for 0.5-1.5 hours; adding the aqueous solution of a reducing agent sodium hydrosulfite to the system and stirring for reacting at a room temperature for 5-60 minutes; next, adding a saturated sodium bicarbonate solution to the reaction liquid to separate out solids, and recrystallizing the solids in a solvent to obtain 3'-hydroxypterostilbene. The preparation method of 3'-hydroxypterostilbene can be used for preparing 3'-hydroxypterostilbene by using pterostilbene as a starting raw material through simple reactions; the reaction conditions are mild, used reaction reagents are clean, the yield is high, and the after-treatment is simple; thus the preparation method of 3'-hydroxypterostilbene is suitable for industrial production.
Description
Technical field
The invention belongs to chemosynthesis technical field, be specifically related to a kind of preparation method of 3'-hydroxyl Pterostilbene.
Background technology
Pterostilene and derivative thereof are the compounds that a class has trans stilbene structure, such as: Pterostilene chemistry 4'-hydroxyl-3,5-dimethoxyl trans toluylene by name, and the initial core material extracted from narra, therefore be named Pterostilene.Research shows, Pterostilene has anti-oxidant, inhibition of cell proliferation, the multiple biological activity such as antimycotic, anticancer.3'-hydroxyl Pterostilbene chemistry 3', 4'-dihydroxyl-3,5-dimethoxyl trans toluylene by name, is Pterostilene 3' position hydroxyl derivatize product, has the activity of good anti-malignant cell proliferation and cell death inducing.
Pterostilene compounds can be prepared by the Sonogashira coupling between the aryl halide of the He Ke linked reaction (Heck-coupling reaction) between the aryl halide of palladium chtalyst and vinylbenzene, palladium chtalyst and phenylacetylene and follow-up hydrogenation reaction, Wittig reaction (wittig-reaction) etc. between aryl aldehydes or ketones and triphenylphosphine ylide.Such as Marinella Robert in 2003 etc. report the related work (J.Med.Chem. based on wittig Reactive Synthesis Pterostilene and 3'-hydroxyl Pterostilbene; 2003; 46; 3546-3554), however this kind of synthetic method exist step various, need protecting group and the shortcomings such as Atom economy difference.
Summary of the invention
In order to solve the shortcoming and defect part of prior art, the object of the present invention is to provide a kind of preparation method of 3'-hydroxyl Pterostilbene.
The object of the invention is achieved through the following technical solutions:
A preparation method for 3'-hydroxyl Pterostilbene, comprises following operation steps:
(1) in organic solvent, Pterostilene (formula 1) and oxygenant 2-iodosobenzoic acid (IBX) is added, stirred at ambient temperature reaction 0.5 ~ 1.5h;
(2) in above-mentioned system, the aqueous solution of reductive agent V-Brite B is added, stirred at ambient temperature reaction 5 ~ 60min;
(3) in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, solid recrystallization in solvent obtains 3'-hydroxyl Pterostilbene (formula 2).
Organic solvent described in step (1) comprises tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), DMF or N,N-dimethylacetamide, preferred DMF.
The mol ratio of described Pterostilene and 2-iodosobenzoic acid is 1.0:1.0 ~ 1.5, and preferred molar ratio is 1.0:1.2.
The time preferably 0.5 ~ 1h of the reaction of stirred at ambient temperature described in step (1).
The mol ratio adding Pterostilene in V-Brite B described in step (2) and step (1) is 2 ~ 4:1, preferred 2:1; Described stirring reaction time preferred 10min.
Solvent preferably water, ethanol, acetone or wherein two or more arbitrarily mixed solvents described in step (3).
Principle of the present invention is: first Pterostilene generates adjacent diquines intermediate under the oxygenizement of IBX, and this intermediate generates product 3'-hydroxyl Pterostilbene under the reductive action of V-Brite B, and its chemical equation is as follows:
Had the following advantages and beneficial effect by preparation method of the present invention and the product tool that obtains:
The present invention take Pterostilene as starting raw material, can prepare 3'-hydroxyl Pterostilbene by easy reaction, and this reaction conditions is gentle, reaction reagent is clean, yield is high, aftertreatment is simple, overcomes the defect of preparation method's complexity in prior art.
Accompanying drawing explanation
Fig. 1 and Fig. 2 be 3'-hydroxyl Pterostilbene standard model (
1h NMR, 400MHz, DMSO-d
6) nmr spectrum;
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.34g, 1.2mmol) and tetrahydrofuran (THF) (8mL), TLC detection reaction progress, stirred at ambient temperature reaction 1h.In above-mentioned reaction solution, add the aqueous solution 6mL of V-Brite B (0.35g, 2mmol), TLC detection reaction, under room temperature, react 10min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid alcohol-water recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.23g, yield 85%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 2
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.42g, 1.5mmol) and tetrahydrofuran (THF) (8mL), TLC detection reaction progress, stirred at ambient temperature reaction 1h.In above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.70g, 4mmol), TLC detection reaction, under room temperature, react 10min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid acetone-water recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.22g, yield 82%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 3
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.34g, 1.2mmol) and tetrahydrofuran (THF) (8mL), TLC detection reaction progress, stirred at ambient temperature reaction 1h.In above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.44g, 2.5mmol), TLC detection reaction, under room temperature, react 15min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid acetone recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.23g, yield 85%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 4
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.34g; 1.2mmol) and N; dinethylformamide (8mL), TLC detection reaction progress, stirred at ambient temperature reaction 0.5h.In above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.52g, 3mmol), TLC detection reaction, under room temperature, react 30min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid ethyl alcohol recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.24g, yield 87%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 5
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.34g; 1.2mmol) and N; N-N,N-DIMETHYLACETAMIDE (8mL), TLC detection reaction progress, stirred at ambient temperature reaction 1.5h.In above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.52g, 3mmol), TLC detection reaction, under room temperature, react 30min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid ethyl alcohol recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.23g, yield 85%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 6
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.34g, 1.2mmol) and dimethyl sulfoxide (DMSO) (8mL), TLC detection reaction progress, stirred at ambient temperature reaction 1h.In above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.52g, 3mmol), TLC detection reaction, under room temperature, react 5min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid ethyl alcohol recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.21g, yield 78%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 7
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.28g; 1.0mmol) and N; dinethylformamide (6mL), TLC detection reaction progress, stirred at ambient temperature reaction 1.5h.Treat that Pterostilene reaction is complete, in above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.35g, 2mmol), TLC detection reaction, under room temperature, react 60min.Then in above-mentioned reaction solution, add saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid ethyl alcohol recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.20g, yield 75%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Embodiment 8
Under room temperature, in the reaction flask of 50mL, add Pterostilene (0.26g, 1mmol), 2-iodosobenzoic acid (0.36g; 1.3mmol) and N; dinethylformamide (5mL), TLC detection reaction progress, stirred at ambient temperature reaction 40min.In above-mentioned reaction solution, add the aqueous solution 8mL of V-Brite B (0.61g, 3.5mmol), TLC detection reaction, under room temperature, react 10min.Then in above-mentioned reaction solution, add a large amount of saturated sodium bicarbonate solution, separate out solid, suction filtration, drying, solid ethyl alcohol recrystallization obtain white solid 3'-hydroxyl Pterostilbene 0.24g, yield 88%.
The characterization data of product is:
1h NMR (400MHz, DMSO-d
6) δ: ppm 9.12 (s, 1H), 8.94 (s, 1H), 7.06 (d, J=16.40Hz, 1H), 6.96 (d, J=2.00Hz, 1H), 6.85 (dd, J
1=8.40Hz, J
2=2.40Hz, 1H), 6.83 (d, J=16.4.0Hz, 1H), 6.72 (d, J=8.40Hz, 1H), 6.70 (d, J=2.00Hz, 2H), 6.34 (t, J=2.00Hz, 1H), 3.75 (s, 6H); MS (EI): m/z=272 [M]
+, 241 [M-OCH
3]
+, 210 [M-COOCH
3]
+.Gained spectrogram is identical with Fig. 1 with Fig. 2, determines that product is 3'-hydroxyl Pterostilbene.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from spirit of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (9)
1. a preparation method for 3'-hydroxyl Pterostilbene, is characterized in that comprising following operation steps:
(1) in organic solvent, Pterostilene and oxygenant 2-iodosobenzoic acid is added, stirred at ambient temperature reaction 0.5 ~ 1.5h;
(2) in above-mentioned system, the aqueous solution of reductive agent V-Brite B is added, stirred at ambient temperature reaction 5 ~ 60min;
(3) in the reaction solution of step (2), add saturated sodium bicarbonate solution, separate out solid, solid recrystallization in solvent obtains 3'-hydroxyl Pterostilbene.
2. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 1, is characterized in that: the organic solvent described in step (1) is selected from tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), DMF or N,N-dimethylacetamide.
3. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 2, is characterized in that: described organic solvent refers to DMF.
4. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 1, is characterized in that: described in step (1), the mol ratio of Pterostilene and 2-iodosobenzoic acid is 1.0:1.0 ~ 1.5.
5. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 4, is characterized in that: the mol ratio of described Pterostilene and 2-iodosobenzoic acid is 1.0:1.2.
6. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 1, is characterized in that: the time of the reaction of stirred at ambient temperature described in step (1) is 0.5 ~ 1h; The stirred at ambient temperature reaction times described in step (2) is 10min.
7. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 1, is characterized in that: the mol ratio adding Pterostilene in the V-Brite B described in step (2) and step (1) is 2 ~ 4:1.
8. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 7, is characterized in that: described V-Brite B and the mol ratio of Pterostilene are 2:1.
9. the preparation method of a kind of 3'-hydroxyl Pterostilbene according to claim 1, is characterized in that: described in step (3), solvent refers to water, ethanol, acetone or wherein two or more arbitrarily mixed solvents.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9458075B1 (en) * | 2015-05-21 | 2016-10-04 | Sami Labs Limited | Process for the manufacture of 3′-hydroxy pterostilbene |
| CN107074705A (en) * | 2014-11-07 | 2017-08-18 | 巴斯夫欧洲公司 | Flavoring substance is used as using the dihydroxy Stilbene of 3,3 ' dimethoxy 4,4 ' |
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| CN1876613A (en) * | 2006-06-23 | 2006-12-13 | 中国科学院广州化学研究所 | (E)-3,5-dimethox-4'-hydroxy diphenyl ethylene synthesis method |
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2014
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1876613A (en) * | 2006-06-23 | 2006-12-13 | 中国科学院广州化学研究所 | (E)-3,5-dimethox-4'-hydroxy diphenyl ethylene synthesis method |
| CN101665418A (en) * | 2009-08-03 | 2010-03-10 | 中国科学院广州化学研究所 | Methods for preparing E-3,5-dimethoxy-4'-oxhydryl diphenylethene and derivative thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107074705A (en) * | 2014-11-07 | 2017-08-18 | 巴斯夫欧洲公司 | Flavoring substance is used as using the dihydroxy Stilbene of 3,3 ' dimethoxy 4,4 ' |
| US9458075B1 (en) * | 2015-05-21 | 2016-10-04 | Sami Labs Limited | Process for the manufacture of 3′-hydroxy pterostilbene |
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