CN102134186A - Method for preparing scutellarin intermediate - Google Patents
Method for preparing scutellarin intermediate Download PDFInfo
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- CN102134186A CN102134186A CN2010101043468A CN201010104346A CN102134186A CN 102134186 A CN102134186 A CN 102134186A CN 2010101043468 A CN2010101043468 A CN 2010101043468A CN 201010104346 A CN201010104346 A CN 201010104346A CN 102134186 A CN102134186 A CN 102134186A
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- 238000000034 method Methods 0.000 title claims abstract description 21
- DJSISFGPUUYILV-UHFFFAOYSA-N UNPD161792 Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-UHFFFAOYSA-N 0.000 title abstract 2
- NPLTVGMLNDMOQE-UHFFFAOYSA-N carthamidin Natural products C1=CC(O)=CC=C1C1OC2=CC(O)=C(O)C(O)=C2C(=O)C1 NPLTVGMLNDMOQE-UHFFFAOYSA-N 0.000 title abstract 2
- DJSISFGPUUYILV-ZFORQUDYSA-N scutellarin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-ZFORQUDYSA-N 0.000 title abstract 2
- 229930190376 scutellarin Natural products 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 5
- 239000002841 Lewis acid Substances 0.000 claims abstract description 5
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 5
- VTCDZPUMZAZMSB-UHFFFAOYSA-N 3,4,5-trimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1OC VTCDZPUMZAZMSB-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 229910015900 BF3 Inorganic materials 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 238000007171 acid catalysis Methods 0.000 claims description 3
- 229960001701 chloroform Drugs 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 abstract description 4
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- OSJPNGZHRQPCCS-UHFFFAOYSA-N 3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound COC1=CC=C(C=C1)C(C=CC1=C(C=C(C(=C1OC)OC)OC)O)=O OSJPNGZHRQPCCS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- -1 2-hydroxyl-4,5,6-trimethoxy methyl phenyl Chemical group 0.000 description 3
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 2
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- FRISOFZUHCOQEC-JXMROGBWSA-N COc1ccc(/C=C/C(c(c(O)cc(OC)c2OC)c2OC)=O)cc1 Chemical compound COc1ccc(/C=C/C(c(c(O)cc(OC)c2OC)c2OC)=O)cc1 FRISOFZUHCOQEC-JXMROGBWSA-N 0.000 description 1
- 240000000230 Chromolaena odorata Species 0.000 description 1
- 235000014493 Crataegus Nutrition 0.000 description 1
- 241001092040 Crataegus Species 0.000 description 1
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001355 anti-mycobacterial effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the chemical synthesis field, and particularly discloses a method for preparing a scutellarin intermediate 1-(4-methoxyphenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl)prop-2-ene-1-one. The method adopts 3,4,5-trimethoxyphenyl and 4-methoxy cinnamic acid or acyl halides as raw materials, and the product is prepared by performing a Friedel-Crafts condensation reaction in a solvent under the catalysis of a lewis acid. The method of the invention has simple process steps, has a yield of up to 90%, and has significant application value in industrial production.
Description
Technical field
The present invention relates to the field of chemical synthesis, be specifically related to the method for a kind of preparation lamp-dish flower acetic intermediate 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) third-2-alkene-1-ketone.
Background technology
1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) third-2-alkene-1-ketone is the important intermediate of preparation cardiovascular medicament lamp-dish flower acetic and lamp-dish flower acetic aglycon.Structural formula is suc as formula shown in (I).
With 2-hydroxyl-4,5,6-trimethoxy methyl phenyl ketone is a raw material, through making compound 1-shown in the formula (I) (4-p-methoxy-phenyl)-3-(2-hydroxyl-4 with the aubepine condensation, 5, the 6-trimethoxyphenyl) third-2-alkene-1-ketone, this compound is the corresponding replacement phenyl styryl ketone precursor molecule of preparation lamp-dish flower acetic aglycon intermediate, the synthetic route of the intermediate of compound lamp-dish flower acetic aglycon shown in the formula (I) is shown below:
Being connected of sugar chain by lamp-dish flower acetic aglycon and 1 β bromo acetyl glucosamine acid methyl esters, the preparation lamp-dish flower acetic, its synthetic route is shown below:
According to article (Suksamrarn, Apichart; Chotipong et al, Antimycobacterialactivity and cytotoxicity of flavonoids from the flowers ofChromolaena odorata, Archives of Pharmacal Research, 27 (5), 507-511 (English) 2004 Pharmaceutical Society of Korea) report, 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5, the 6-trimethoxyphenyl) third-2-alkene-1-ketone can be from extraction separation the spending of Siam's grass (Chromolaena odorata), but this compounds content is few in the spending of Siam's grass, and productive rate is low.Still do not have at present the synthetic 1-(4-p-methoxy-phenyl) of the higher chemical process of yield-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) third-2-alkene-1-ketone, can not satisfy industrial needs.
Summary of the invention
The present invention is directed to prior art for preparing 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) deficiency that third-2-alkene-1-ketone yield is low, a kind of new preparation method is provided.
In order to realize the foregoing invention purpose, the invention provides the method for compound shown in a kind of preparation formula (I),
With 3,4, compound is a raw material shown in 5-trimethoxy phenol and the formula (II), carries out the Friedel-Crafts reaction under Louis acid catalysis in solvent, compound shown in the production (I),
In formula (I) and the formula (II), X is-OH or halogen atom.Described halogen atom comprises Cl, Br, I.Reaction formula is as follows:
Described solvent is preferably a kind of or its two or more mixtures in ether, hydrocarbon or the replacement hydrocarbon.Described ether is preferably tetrahydrofuran (THF), dioxane or methyl tertiary butyl ether.
Described hydrocarbon or replacement hydrocarbon are preferably benzene, toluene, methylene dichloride or trichloromethane.
Described solvent and 3,4, the volume mass of 5-trimethoxy phenol is than preferably counting 20: 1 with ml/g.
Described Lewis acid comprises aluminum chloride, boron trifluoride, Zinc Chloride Anhydrous, polyphosphoric acid, Vanadium Pentoxide in FLAKES.
Described Lewis acid and 3,4,5-trimethoxy phenol consumption are preferably mol ratio 1: 1～2.
Described 3,4, the compound preferred molar ratio is 1: 1～1.25 shown in 5-trimethoxy phenol and the formula (II).
Preferably, described Friedel-Crafts is reflected under 0～100 ℃ of the temperature and carries out.
Preparation lamp-dish flower acetic provided by the invention and aglycon key intermediate 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4 thereof, 5, the 6-trimethoxyphenyl) method of third-2-alkene-1-ketone, with 3,4,5-trimethoxy phenol and 4-methoxy cinnamic acid or its carboxylic acid halides are raw material, condensation makes 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4 under Louis acid catalysis, 5, the 6-trimethoxyphenyl) third-2-alkene-1-ketone, processing step is simple, and yield can reach about 90%, has significant industrial production using value.
Embodiment
Below in conjunction with embodiment, further set forth the present invention:
The invention discloses the method for a kind of preparation 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) third-2-alkene-1-ketone, those skilled in the art can use for reference this paper content, suitably improve processing parameter and realize.Special needs to be pointed out is that all similarly replace and change apparent to those skilled in the art, they all are regarded as being included in the present invention.The method of the invention is described by preferred embodiment, and the related personnel obviously can change or suitably change and combination methods described herein in not breaking away from content of the present invention, spirit and scope, realizes and use the present invention.
Embodiment 1:
Take by weighing 18.4g (0.10mol) compound 1,3,4,5-trimethoxy phenol, 21.4g (0.12mol) the 4-methoxy cinnamic acid places the 500ml round-bottomed flask, add 150ml methylene dichloride and 30ml boron trifluoride ether solution (wherein boron trifluoride content 46.8-47.8% (g/ml)), 0 ℃ of following stirring reaction 10 hours.Add 300ml water after removing most of solvent under reduced pressure, regulate pH8～9 and fully stirring with thanomin then.Filter, collecting precipitation, precipitation press dry with the little water washing, and 60 ℃ are drying to obtain 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) third-2-alkene-1-ketone, yield: 87.5%.
1HNMR(CDCl
3)：δ13.83(s，1H)，δ7.88(s，1H)，δ7.87(s，1H)，δ7.63(d，J＝8.5Hz，2H)，δ6.98(d，J＝8.5Hz，2H)，δ6.32(s，1H)，δ3.94(s，3H)，δ3.92(s，3H)，δ3.88(s，3H)，δ3.86(s，3H)。MS(m/e)：344。
Embodiment 2:
Take by weighing 18.4g (0.10mol) compound 1,3,4,5-trimethoxy phenol, 18.7g (0.11mol) 4-methoxyl group cinnamyl chloride places the 500ml round-bottomed flask, adds 360ml trichloromethane and 20g Zinc Chloride Anhydrous, and heating was 80 ℃ of following stirring reactions 6 hours.Add 300ml water after removing most of solvent under reduced pressure, and fully stir.Filter, collecting precipitation, precipitation press dry with the little water washing, and 60 ℃ are drying to obtain product, yield: 91.0%.
1HNMR (CDCl
3): the same.
Embodiment 3:
Take by weighing 18.4g (0.10mol) compound 1,3,4,5-trimethoxy phenol, 21.2g (0.125mol) 4-methoxyl group cinnamyl bromide places the 500ml round-bottomed flask, adds 150ml benzene and 14.2g Vanadium Pentoxide in FLAKES, and heating was 100 ℃ of following stirring reactions 6 hours.Add 300ml water after removing solvent under reduced pressure, and fully stir.Filter, collecting precipitation, precipitation press dry with the little water washing, and 60 ℃ are drying to obtain product, yield: 91.0%.
1HNMR (CDCl
3): the same.
Embodiment 4:
Take by weighing 18.4g (0.10mol) compound 1,3,4,5-trimethoxy phenol, 18.7g (0.11mol) 4-methoxyl group cinnamyl chloride places the 500ml round-bottomed flask, adds 360ml tetrahydrofuran (THF) and 30ml polyphosphoric acid, and heating was 80 ℃ of following stirring reactions 6 hours.Add 300ml water after removing most of solvent under reduced pressure, and fully stir.Filter, collecting precipitation, precipitation press dry with the little water washing, and 60 ℃ are drying to obtain product, yield: 90.8%.
1HNMR (CDCl
3): the same.
Embodiment 5:
Take by weighing 18.4g (0.10mol) compound 1,3,4,5-trimethoxy phenol, 21.2g (0.125mol) 4-methoxyl group cinnamyl bromide places the 500ml round-bottomed flask, adds 14.2g aluminum chloride and 150ml toluene, and heating was 90 ℃ of following stirring reactions 10 hours.Add 300ml water after removing most of solvent under reduced pressure, and fully stir.Filter, collecting precipitation, precipitation press dry with the little water washing, and 60 ℃ are drying to obtain product, yield: 91.2%.
1HNMR (CDCl
3): the same.
Embodiment 6:
Take by weighing 18.4g (0.10mol) compound 1,3,4,5-trimethoxy phenol, 21.4g (0.12mol) the 4-methoxy cinnamic acid places the 500ml round-bottomed flask, the mixture and the 30ml boron trifluoride ether solution (wherein boron trifluoride content 46.8-47.8% (g/ml)) that add 150ml dioxane and benzene were 10 ℃ of following stirring reactions 10 hours.Add 300ml water after removing most of solvent under reduced pressure, regulate pH8～9 and fully stirring with thanomin then.Filter, collecting precipitation, precipitation press dry with the little water washing, and 60 ℃ are drying to obtain 1-(4-p-methoxy-phenyl)-3-(2-hydroxyl-4,5,6-trimethoxyphenyl) third-2-alkene-1-ketone, yield: 89.5%.
1HNMR(CDCl
3)：δ13.83(s，1H)，δ7.88(s，1H)，δ7.87(s，1H)，δ7.63(d，J＝8.5Hz，2H)，δ6.98(d，J＝8.5Hz，2H)，δ6.32(s，1H)，δ3.94(s，3H)，δ3.92(s，3H)，δ3.88(s，3H)，δ3.86(s，3H)。MS(m/e)：344。
Claims (9)
1. the method for compound shown in the preparation formula (I),
It is characterized in that, 3,4, compound shown in the Friedel-Crafts reaction production (I) takes place with compound shown in the formula (II) in 5-trimethoxy phenol in solvent under Louis acid catalysis,
Wherein X is-OH or halogen atom.
2. method according to claim 1 is characterized in that, described solvent is ether, hydrocarbon or replaces a kind of in the hydrocarbon or mixture that they are two or more.
3. method according to claim 2 is characterized in that, described ether is tetrahydrofuran (THF), dioxane or methyl tertiary butyl ether.
4. method according to claim 2 is characterized in that, described hydrocarbon or replacement hydrocarbon comprise benzene, toluene, methylene dichloride and trichloromethane.
5. according to each described method of claim 1-4, it is characterized in that, described solvent and 3,4, the volume mass of 5-trimethoxy phenol is than counting 20: 1 with ml/g.
6. method according to claim 1 is characterized in that described Lewis acid comprises aluminum chloride, boron trifluoride, Zinc Chloride Anhydrous, polyphosphoric acid, Vanadium Pentoxide in FLAKES.
7. according to claim 1 or 6 described methods, it is characterized in that, described Lewis acid and 3,4,5-trimethoxy phenol consumption mol ratio is 1: 1～2.
8. method according to claim 1 is characterized in that, and is described 3,4, and the compound mol ratio is 1: 1～1.25 shown in 5-trimethoxy phenol and the formula (II).
9. according to claim 1,2 or 6 described methods, it is characterized in that it is to carry out under 0～100 ℃ that described Friedel-Crafts is reflected at temperature.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102746351A (en) * | 2012-07-23 | 2012-10-24 | 上海蓝木化工有限公司 | Method for preparing scutellarin and analogues thereof |
| CN105218606A (en) * | 2015-10-19 | 2016-01-06 | 昆明理工大学 | A kind of method preparing scutellarin |
| CN107759551A (en) * | 2016-08-22 | 2018-03-06 | 昆明龙津药业股份有限公司 | A kind of synthetic method of breviscapine B aglycone |
| CN111170979A (en) * | 2020-01-06 | 2020-05-19 | 厦门大学 | Preparation method of bioactive compound (S) -2- (4-hydroxyphenyl) -7-methoxy flavanone in Zhangzhou narcissus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040242907A1 (en) * | 2003-05-30 | 2004-12-02 | Unitech Pharmaceuticals, Inc. | Methods of synthesizing flavonoids and chalcones |
| CN101538298A (en) * | 2009-04-29 | 2009-09-23 | 四川抗菌素工业研究所有限公司 | A method for synthesizing 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid |
-
2010
- 2010-01-25 CN CN2010101043468A patent/CN102134186A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040242907A1 (en) * | 2003-05-30 | 2004-12-02 | Unitech Pharmaceuticals, Inc. | Methods of synthesizing flavonoids and chalcones |
| CN101538298A (en) * | 2009-04-29 | 2009-09-23 | 四川抗菌素工业研究所有限公司 | A method for synthesizing 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102746351A (en) * | 2012-07-23 | 2012-10-24 | 上海蓝木化工有限公司 | Method for preparing scutellarin and analogues thereof |
| CN102746351B (en) * | 2012-07-23 | 2018-03-02 | 上海弈柯莱生物医药科技有限公司 | The preparation method of lamp-dish flower acetic and the like |
| CN105218606A (en) * | 2015-10-19 | 2016-01-06 | 昆明理工大学 | A kind of method preparing scutellarin |
| CN105218606B (en) * | 2015-10-19 | 2017-12-01 | 昆明理工大学 | A kind of method for preparing scutellarin |
| CN107759551A (en) * | 2016-08-22 | 2018-03-06 | 昆明龙津药业股份有限公司 | A kind of synthetic method of breviscapine B aglycone |
| CN107759551B (en) * | 2016-08-22 | 2021-10-01 | 昆明龙津药业股份有限公司 | Method for synthesizing scutellarin aglycone |
| CN111170979A (en) * | 2020-01-06 | 2020-05-19 | 厦门大学 | Preparation method of bioactive compound (S) -2- (4-hydroxyphenyl) -7-methoxy flavanone in Zhangzhou narcissus |
| CN111170979B (en) * | 2020-01-06 | 2022-02-08 | 厦门大学 | Preparation method of bioactive compound (S) -4' -hydroxy-7-methoxy flavanone in Zhangzhou narcissus |
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