CN111303105A - 一种7,8-二羟基黄酮的制备方法 - Google Patents
一种7,8-二羟基黄酮的制备方法 Download PDFInfo
- Publication number
- CN111303105A CN111303105A CN201910318750.6A CN201910318750A CN111303105A CN 111303105 A CN111303105 A CN 111303105A CN 201910318750 A CN201910318750 A CN 201910318750A CN 111303105 A CN111303105 A CN 111303105A
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- CN
- China
- Prior art keywords
- compound
- reaction
- product
- temperature
- dihydroxyflavone
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- COCYGNDCWFKTMF-UHFFFAOYSA-N 7,8-dihydroxyflavone Chemical compound OC=1C(O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 COCYGNDCWFKTMF-UHFFFAOYSA-N 0.000 title claims abstract description 55
- WWGFXSLWIRYIBP-UHFFFAOYSA-N 7,8-dihydroxy-4H-chromen-4-one Natural products O1C=CC(=O)C=2C1=C(O)C(O)=CC=2 WWGFXSLWIRYIBP-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- 239000000047 product Substances 0.000 claims abstract description 36
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 26
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 26
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims abstract description 22
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011630 iodine Substances 0.000 claims abstract description 14
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 11
- 229940079877 pyrogallol Drugs 0.000 claims abstract description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 75
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000001035 drying Methods 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 27
- 238000000967 suction filtration Methods 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000002844 melting Methods 0.000 claims description 24
- 230000008018 melting Effects 0.000 claims description 24
- 230000005311 nuclear magnetism Effects 0.000 claims description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 22
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 19
- 238000005406 washing Methods 0.000 claims description 19
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000012265 solid product Substances 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052786 argon Inorganic materials 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 10
- 229940073608 benzyl chloride Drugs 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000005457 ice water Substances 0.000 claims description 7
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 7
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000006722 reduction reaction Methods 0.000 claims description 4
- 238000009987 spinning Methods 0.000 claims description 4
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000012467 final product Substances 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- MQGPSCMMNJKMHQ-UHFFFAOYSA-N 7-hydroxyflavone Chemical compound C=1C(O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 MQGPSCMMNJKMHQ-UHFFFAOYSA-N 0.000 description 6
- XIROXSOOOAZHLL-UHFFFAOYSA-N 2',3',4'-Trihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1O XIROXSOOOAZHLL-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 102000004219 Brain-derived neurotrophic factor Human genes 0.000 description 1
- 108090000715 Brain-derived neurotrophic factor Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 230000005978 brain dysfunction Effects 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 238000010511 deprotection reaction 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
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- -1 flavonoid compounds Chemical class 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 102000015534 trkB Receptor Human genes 0.000 description 1
- 108010064880 trkB Receptor Proteins 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
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CN201910318750.6A CN111303105A (zh) | 2019-04-19 | 2019-04-19 | 一种7,8-二羟基黄酮的制备方法 |
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CN201910318750.6A CN111303105A (zh) | 2019-04-19 | 2019-04-19 | 一种7,8-二羟基黄酮的制备方法 |
Publications (1)
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CN111303105A true CN111303105A (zh) | 2020-06-19 |
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CN201910318750.6A Pending CN111303105A (zh) | 2019-04-19 | 2019-04-19 | 一种7,8-二羟基黄酮的制备方法 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114276321A (zh) * | 2021-12-21 | 2022-04-05 | 济南明微医药科技有限公司 | 一种制备7,8-二羟基黄酮的方法 |
WO2023198055A1 (zh) * | 2022-04-12 | 2023-10-19 | 泉州海创医药科技有限公司 | 7,8-二羟基黄酮的多晶型物及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB875164A (en) * | 1956-08-03 | 1961-08-16 | Nat Res Dev | New hydroxyflavones, their production and use as anti-oxidants |
CN102127044A (zh) * | 2010-12-30 | 2011-07-20 | 陕西嘉禾植物化工有限责任公司 | 一种5,7-二羟基黄酮的合成方法 |
-
2019
- 2019-04-19 CN CN201910318750.6A patent/CN111303105A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB875164A (en) * | 1956-08-03 | 1961-08-16 | Nat Res Dev | New hydroxyflavones, their production and use as anti-oxidants |
CN102127044A (zh) * | 2010-12-30 | 2011-07-20 | 陕西嘉禾植物化工有限责任公司 | 一种5,7-二羟基黄酮的合成方法 |
Non-Patent Citations (9)
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114276321A (zh) * | 2021-12-21 | 2022-04-05 | 济南明微医药科技有限公司 | 一种制备7,8-二羟基黄酮的方法 |
WO2023198055A1 (zh) * | 2022-04-12 | 2023-10-19 | 泉州海创医药科技有限公司 | 7,8-二羟基黄酮的多晶型物及其制备方法 |
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PB01 | Publication | ||
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SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information | ||
CB02 | Change of applicant information |
Address after: 437200, Hubei Province, Jiayu County, Xianning Province Pan Wan fan Lake Industrial Park Applicant after: Hubei Wanzhi Chemical Pharmaceutical Co.,Ltd. Applicant after: WUHAN TECHNOLOGY AND BUSINESS University Address before: 437200, Hubei Province, Jiayu County, Xianning Province Pan Wan fan Lake Industrial Park Applicant before: WUHAN WANZHI CHEMICAL MEDICINE Co.,Ltd. Applicant before: WUHAN TECHNOLOGY AND BUSINESS University |
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RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200619 |