CN105693477A - Synthesis method of trimethoxystilbene - Google Patents
Synthesis method of trimethoxystilbene Download PDFInfo
- Publication number
- CN105693477A CN105693477A CN201610169675.8A CN201610169675A CN105693477A CN 105693477 A CN105693477 A CN 105693477A CN 201610169675 A CN201610169675 A CN 201610169675A CN 105693477 A CN105693477 A CN 105693477A
- Authority
- CN
- China
- Prior art keywords
- resveratrol
- methyl ether
- reaction
- room temperature
- 1mol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- GDHNBPHYVRHYCC-SNAWJCMRSA-N 1,3-dimethoxy-5-[(e)-2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC(OC)=CC(OC)=C1 GDHNBPHYVRHYCC-SNAWJCMRSA-N 0.000 title abstract 4
- 238000001308 synthesis method Methods 0.000 title abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 238000001953 recrystallisation Methods 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 25
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 25
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 25
- 229940016667 resveratrol Drugs 0.000 claims description 25
- 235000021283 resveratrol Nutrition 0.000 claims description 25
- 238000010189 synthetic method Methods 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 10
- 238000010792 warming Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 abstract 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 244000050510 Cunninghamia lanceolata Species 0.000 description 1
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 1
- 101710082112 Hematopoietic prostaglandin D synthase Proteins 0.000 description 1
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 description 1
- 101710150918 Macrophage colony-stimulating factor 1 receptor Proteins 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 239000002461 renin inhibitor Substances 0.000 description 1
- 229940086526 renin-inhibitors Drugs 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of trimethoxystilbene. The method comprises the following steps of (1) at room temperature, adding trifluoromethanesulfonic acid into dichloromethane; stirring the mixture; slowly dripping sulfoxide chloride; after the dripping is completed, performing stirring reaction for 12 hours at room temperature; concentrating a reaction system to obtain a coarse product of trifluoromethanesulfonyl chloride; (2) adding aniline and triethylamine into dichloromethane; lowering the temperature to 0 DEG C; dripping the obtained coarse product of trifluoromethanesulfonyl chloride through a dropping funnel; after the dripping is completed, raising the temperature to room temperature for reaction for 2 hours; performing water washing, drying and concentration on the reaction system; then, performing recrystallization by petroleum ether to obtain trimethoxystilbene. The synthesis method has the beneficial effects that the raw materials of trifluoromethanesulfonic acid used by the synthesis method of trimethoxystilbene provided by the invention are common chemical raw materials; the price is low; the acquisition is easy; the cost is greatly reduced; special equipment such as low-temperature kettles is not needed in the production process; the operation is easy; the method is suitable for industrial production.
Description
Technical field
The present invention relates to compou nd synthesis technical field, be specifically related to the synthetic method of a kind of resveratrol three methyl ether。
Background technology
Resveratrol three methyl ether is the important synthesis material of a lot of antimicrobial drug, appetrol, cancer therapy drug and adjuvant。Such as prepare and there are the H-PGDS inhibitor of antitumaous effect, Rho-inhibitors of kinases, KSP inhibitor, CSF-1R inhibitor, renin inhibitor etc.。In the last few years a series of be key intermediate with this compounds new drug be found, the demand of such intermediate is increased by market day by day。But by the investigation to existing market, large-scale Reagent Company of domestic only several families provides gram level fractional pack of reagent grade at present, there is no any unit and can provide this product in bulk。
It is currently known the synthetic method of resveratrol three methyl ether that large-scale corporation de facto of a few family of Cunninghamia lanceolata (Lamb.) Hook. can be provided by, is all with trifluoromethanesulfanhydride anhydride for raw material, in subzero 80 degree of reactions, process to obtain product。Raw material trifluoromethanesulfanhydride anhydride used by the method is expensive, and is all import；Needing in production to use subzero 80 degree of low-temp reaction stills, the method cost is high, equipment requirements is high, not easily operate, be difficult to amplification produces。
Summary of the invention
The purpose of the present invention is aiming at above-mentioned defect of the prior art, it is provided that a kind of cost is low, without special installation, easily operate and be suitable to the synthetic method of resveratrol three methyl ether of industrialized production。
To achieve these goals, technical scheme provided by the invention is: the synthetic method of a kind of resveratrol three methyl ether, comprises the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 0.5-1.5mol, control time 55-65min and dropwise, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride；
2) triethylamine of the aniline of 1mol, 0.5-1.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 0.5-1.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
The process of reaction is as shown in Figure 1。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, in described step 1), the addition of thionyl chloride is 1mol。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, in described step 1), the time for adding of thionyl chloride is 60min。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, described step 2) in, the addition of triethylamine is 1mol。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, described step 2) in, the dripping quantity of product trifluoromethanesulfchloride chloride is 1mol。
The invention have the benefit that the synthetic method of a kind of resveratrol three methyl ether provided by the invention, its raw materials used trifluoromethanesulfonic acid, for common industrial chemicals, cheap and easy to get, greatly reduce cost, and production process does not need the special installations such as low temperature still, it is easy to and operation, be suitable to industrialized production。
Accompanying drawing explanation
Fig. 1 is the reaction scheme schematic diagram of the synthetic method of a kind of resveratrol three methyl ether provided by the invention。
Detailed description of the invention
Embodiment 1:
A kind of synthetic method of resveratrol three methyl ether, the process of reaction is as it is shown in figure 1, comprise the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 0.5mol, the control time, 55min dropwised, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride, it is not necessary to purification, can be directly used for next step reaction；
2) triethylamine of the aniline of 1mol, 0.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 0.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
Embodiment 2:
A kind of synthetic method of resveratrol three methyl ether, the process of reaction is as it is shown in figure 1, comprise the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 1.5mol, the control time, 65min dropwised, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride, it is not necessary to purification, can be directly used for next step reaction；
2) triethylamine of the aniline of 1mol, 1.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 1.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
Embodiment 3:
A kind of synthetic method of resveratrol three methyl ether, the process of reaction is as it is shown in figure 1, comprise the following steps:
1), under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 1mol, the control time, 60min dropwised, and reaction 12 hour is stirred at room temperature, reaction system concentrates to obtain crude product trifluoromethanesulfchloride chloride, without purification, can be directly used for next step reaction；
2) triethylamine of the aniline of 1mol, 1mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 1mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
Last it is noted that the foregoing is only the preferred embodiments of the present invention, it is not limited to the present invention, although the present invention being described in detail with reference to previous embodiment, for a person skilled in the art, technical scheme described in foregoing embodiments still can be modified by it, or wherein portion of techniques feature carries out equivalent replacement。All within the spirit and principles in the present invention, any amendment of making, equivalent replacement, improvement etc., should be included within protection scope of the present invention。
Claims (5)
1. the synthetic method of resveratrol three methyl ether, it is characterised in that comprise the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 0.5-1.5mol, control time 55-65min and dropwise, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride；
2) triethylamine of the aniline of 1mol, 0.5-1.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 0.5-1.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
2. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that in described step 1), the addition of thionyl chloride is 1mol。
3. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that in described step 1), the time for adding of thionyl chloride is 60min。
4. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that described step 2) in, the addition of triethylamine is 1mol。
5. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that described step 2) in, the dripping quantity of product trifluoromethanesulfchloride chloride is 1mol。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610169675.8A CN105693477A (en) | 2016-03-23 | 2016-03-23 | Synthesis method of trimethoxystilbene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610169675.8A CN105693477A (en) | 2016-03-23 | 2016-03-23 | Synthesis method of trimethoxystilbene |
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| CN105693477A true CN105693477A (en) | 2016-06-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201610169675.8A Pending CN105693477A (en) | 2016-03-23 | 2016-03-23 | Synthesis method of trimethoxystilbene |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627691A (en) * | 2019-08-20 | 2019-12-31 | 中船重工（邯郸）派瑞特种气体有限公司 | Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imine |
| CN112830887A (en) * | 2020-12-30 | 2021-05-25 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113735693A (en) * | 2021-10-20 | 2021-12-03 | 河北维达康生物科技有限公司 | Synthesis method of resveratrol monomethyl ether |
| CN115724774A (en) * | 2022-12-16 | 2023-03-03 | 山东华安新材料有限公司 | Preparation method of trifluoromethyl sulfonyl chloride |
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| EP1016655A2 (en) * | 1998-12-28 | 2000-07-05 | Central Glass Company, Limited | Method for producing trifluoromethanesulfonyl chloride |
| CN1445216A (en) * | 2003-03-03 | 2003-10-01 | 中国科学院广州化学研究所 | Nicotinic acid ester of resveratrol and its synthetic method |
| JP2003286244A (en) * | 2002-03-27 | 2003-10-10 | Yakult Honsha Co Ltd | Method for producing N-phenylbis (trifluoromethanesulfonimide) |
| JP2009102294A (en) * | 2007-10-02 | 2009-05-14 | Central Glass Co Ltd | Method for purification of trifluoromethanesulfonyl fluoride |
| JP2010173959A (en) * | 2009-01-29 | 2010-08-12 | Central Glass Co Ltd | Method for purifying trifluoromethanesulfonyl fluoride |
| CN101875600A (en) * | 2010-05-11 | 2010-11-03 | 成都新基科技有限公司 | Synthesis method for industrially producing resveratrol |
| WO2012170439A1 (en) * | 2011-06-06 | 2012-12-13 | The Ohio State University | Methods for stabilizing hypoxia inducible factor-2 alpha as a method for treating cancer |
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2016
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627691A (en) * | 2019-08-20 | 2019-12-31 | 中船重工（邯郸）派瑞特种气体有限公司 | Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imine |
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| CN112830887A (en) * | 2020-12-30 | 2021-05-25 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113735693A (en) * | 2021-10-20 | 2021-12-03 | 河北维达康生物科技有限公司 | Synthesis method of resveratrol monomethyl ether |
| CN115724774A (en) * | 2022-12-16 | 2023-03-03 | 山东华安新材料有限公司 | Preparation method of trifluoromethyl sulfonyl chloride |
| CN115724774B (en) * | 2022-12-16 | 2023-12-26 | 山东华安新材料有限公司 | Preparation method of trifluoromethyl sulfonyl chloride |
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Application publication date: 20160622 |
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