CN106588613A - Method for preparing 3,4,5-triethoxy-3',4'-dimethoxy chalcone - Google Patents
Method for preparing 3,4,5-triethoxy-3',4'-dimethoxy chalcone Download PDFInfo
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- CN106588613A CN106588613A CN201611117585.0A CN201611117585A CN106588613A CN 106588613 A CN106588613 A CN 106588613A CN 201611117585 A CN201611117585 A CN 201611117585A CN 106588613 A CN106588613 A CN 106588613A
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- dimethoxy
- chalcone
- trimethoxies
- triethoxy
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- 238000000034 method Methods 0.000 title abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 29
- 238000003756 stirring Methods 0.000 abstract description 7
- 239000003960 organic solvent Substances 0.000 abstract description 2
- IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 abstract 2
- JSXXRCHIEZJFCY-UHFFFAOYSA-N 3,4,5-triethoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC(OCC)=C1OCC JSXXRCHIEZJFCY-UHFFFAOYSA-N 0.000 abstract 1
- 239000011830 basic ionic liquid Substances 0.000 abstract 1
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002608 ionic liquid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001788 chalcone derivatives Chemical class 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- -1 methoxyl group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- MLNKXLRYCLKJSS-RMKNXTFCSA-N (2e)-2-hydroxyimino-1-phenylethanone Chemical compound O\N=C\C(=O)C1=CC=CC=C1 MLNKXLRYCLKJSS-RMKNXTFCSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- 230000001772 anti-angiogenic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical group 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for preparing 3,4,5-triethoxy-3',4'-dimethoxy chalcone. The method comprises the following steps: dissolving 3,4-dimethoxyacetophenone and 3,4,5-triethoxy benzaldehyde in a strong basic ionic liquid, stirring at room temperature, after completing the reaction, leaving to stand a reaction liquid, filtering, washing with water, and drying, thereby obtaining the 3,4,5-triethoxy-3',4'-dimethoxy chalcone. The method is gentle in reaction condition, relatively low in reaction equipment requirement, low in reaction cost and convenient in on-scale production, in addition, environmental pollution caused by organic solvents can be effectively avoided, the yield and the purity of a product prepared with the method are relatively high, and the reaction efficiency can be greatly improved.
Description
Technical field
The present invention relates to a kind of preparation method of antitumor drug, more particularly, to 3,4,5- trimethoxies -3 ', 4 '-two
The preparation method of methoxyl group chalcone.
Background technology
Malignant tumor is the major disease for seriously threatening people's life and health, and the chemotherapys of tumor remain swollen
Tumor treats indispensable important means.For effective antitumour target spot, Development of Novel effective antitumour medicine is then real
Existing tumor effectively chemotherapeutical important channel.
Chalcone compounds are widely present in nature, and its basic skeleton structure is 1,3- diphenylprop ketenes.Mesh
Front research finds to introduce various substituent groups on basic skeleton structure, and chalcone compounds can be made to show new physiology
And pharmaceutically active.Being related to the activity of chalcone compounds includes anti-inflammatory activity, antiangiogenic activity, antimicrobial
Activity, antibacterial activity, optical recording material, antidepressants, pesticide, antitumor etc..Such as Chinese patent CN200710037570.8
Disclose the chalcone compounds with suppression tumor or suppression cell hyperproliferation effect of a type.
Chinese patent 201610317261.5 discloses 3,4,5- trimethoxies -3 ', 4 '-dimethoxy chalcone, the change
Compound has stronger inhibitory activity to human lung cancer cell A549, human colon carcinoma SW620 and human liver cancer cell HepG2, and the patent is led to
3,4- dimethoxy-acetophenones and TMB are crossed, under the catalysis of sodium hydroxide, 3,4,5- trimethoxies is prepared
Base -3 ', 4 '-dimethoxy chalcone, however, the patent catalysts alkalescence is strong, and it is big to equipment corrosion, it is unfavorable for scale
Metaplasia is produced, simultaneously as using sodium hydroxide catalyst, the by-product of reaction is more, Reaction Separation is difficult, and reaction yield is relatively low,
Highest response yield is only 44.3%, and reaction cost valency is high.
The content of the invention
In order to solve the above-mentioned problems in the prior art, it is an object of the invention to provide a kind of 3,4,5- trimethoxies
Base -3 ', the preparation method of 4 '-dimethoxy chalcone, the method reaction condition is gentle, requires consersion unit relatively low, saving
Reaction cost, and organic solvent pollution on the environment is effectively prevent, it is easy to large-scale production, the method product
Yield and purity are higher, substantially increase the efficiency of reaction.
The technical solution used in the present invention is：
3,4,5- of one kind trimethoxies -3 ', the preparation method of 4 '-dimethoxy chalcone, it is characterised in that：By 3,4- dimethoxies
Benzoylformaldoxime and 3,4,5-Trimethoxybenzaldehyde are dissolved in strong basic ion liquid, are stirred at room temperature, after question response terminates, will be anti-
Answer liquid to stand, filter, after washing, drying 3,4,5- trimethoxies -3 obtained ', 4 '-dimethoxy chalcone.
Further, described 3,4- dimethoxy-acetophenones and the mol ratio of 3,4,5-Trimethoxybenzaldehyde is 1:5
～5:1, preferably 1:2～2:1.
Further, described 3,4- dimethoxy-acetophenones and the mol ratio of strong basic ion liquid is 1:1～10, it is excellent
Elect 1 as:2～5.
Further, described alkali ionic liquid is：
Or。
Further, described alkali ionic liquid is：
。
Compared to prior art, the solution have the advantages that：
1st, reaction substrate of the invention is 3,4- dimethoxy-acetophenones and 3,4,5-Trimethoxybenzaldehyde, due to raw material phenyl ring
Present on multiple methoxyl groups it is unstable in the presence of inorganic acid and inorganic strong alkali, cause the condensation reaction to produce greatly
The by-product of amount, while the aldehyde radical in the active methyl and benzaldehyde in 1-Phenylethanone. is also unstable in inorganic acid and inorganic strong alkali
It is fixed, cause the generation of a large amount of by-products, it is unfavorable for the separation and post processing of product, the alkali ion resin used by the present invention
The generation of a large amount of by-products is avoided, post-reaction treatment is simple, and product purity is high；
2nd, the catalyst adopted in prior art is inorganic base sodium hydroxide, easily causes the generation of byproduct of reaction, while hydrogen-oxygen
Change sodium is highly basic, strong to the corrosivity of equipment, and reaction has high demands to equipment, and reaction cost is high, is unfavorable for that scale chemical conversion is produced, and
The present invention do not need reaction dissolvent, strong basic ion liquid both to do reaction dissolvent or done catalysts, it is to avoid to environment
Pollution, while using strong basic ion liquid, the efficiency of reaction is substantially improved, response speed is fast, and reaction yield is high, highest yield
Up to 88.3%, purity can be to 99.2%.
Specific embodiment
Embodiment 1
The preparation of strong basic ion liquid：
By N- Methylimidazole .s and excessive chloro-normal butane in reflux in toluene 45 hours, the chlorine of 1- butyl -3- Methylimidazole .s is obtained
Salt.With this villaumite and NH4OH is carried out after ion-exchange reactionss in acetonitrile solution, filter, except solvent, vacuum drying respectively obtain
Corresponding alkali ionic liquid 1, is shown below：
1。
Embodiment 2
By N- Methylimidazole .s and excessive chloro-normal butane in reflux in toluene 45 hours, the chlorine of 1- butyl -3- Methylimidazole .s is obtained
Salt.With this villaumite and NH4HCO3Carry out in acetonitrile solution after ion-exchange reactionss, filter, except solvent, vacuum drying respectively
To corresponding alkali ionic liquid 2, it is shown below：
2。
Embodiment 3
To in reaction bulb, 0.5mol alkali ionic liquids 1,0.1mol3,4- dimethoxy-acetophenones and 0.1mol3 are added, 4,5-
TMB, stirring reaction under room temperature, after reacting 8 hours, reactant liquor is stood, is filtered by stopping stirring, is washed, is done
3,4,5- trimethoxies -3 are obtained after dry ', 4 '-dimethoxy chalcone crude product, gained crude product ethyl alcohol recrystallization obtains 3,4,
5- trimethoxies -3 ', 4 '-dimethoxy chalcone, yield 88.3%, purity 98.8%.
Embodiment 4
To in reaction bulb, 0.5mol alkali ionic liquids 1,0.2mol3,4- dimethoxy-acetophenones and 0.3mol3 are added, 4,5-
TMB, stirring reaction under room temperature, after reacting 6 hours, reactant liquor is stood, is filtered by stopping stirring, is washed, is done
3,4,5- trimethoxies -3 are obtained after dry ', 4 '-dimethoxy chalcone crude product, gained crude product ethyl alcohol recrystallization obtains 3,4,
5- trimethoxies -3 ', 4 '-dimethoxy chalcone, yield 86.9%, purity 99.2%.
Embodiment 5
To in reaction bulb, 0.5mol alkali ionic liquids 2,0.1mol3,4- dimethoxy-acetophenones and 0.1mol3 are added, 4,5-
TMB, stirring reaction under room temperature, after reacting 8 hours, reactant liquor is stood, is filtered by stopping stirring, is washed, is done
3,4,5- trimethoxies -3 are obtained after dry ', 4 '-dimethoxy chalcone crude product, gained crude product ethyl alcohol recrystallization obtains 3,4,
5- trimethoxies -3 ', 4 '-dimethoxy chalcone, yield 80.5%, purity 99.1%.
Claims (5)
1. one kind 3,4,5- trimethoxies -3 ', the preparation method of 4 '-dimethoxy chalcone, it is characterised in that：By 3,4- diformazans
Epoxide 1-Phenylethanone. and 3,4,5-Trimethoxybenzaldehyde are dissolved in strong basic ion liquid, are stirred at room temperature, after question response terminates, will
Reactant liquor stands, filters, and after washing, drying 3,4,5- trimethoxies -3 are obtained ', 4 '-dimethoxy chalcone.
2. 3,4,5- trimethoxies -3 of one kind as claimed in claim 1 ', the preparation method of 4 '-dimethoxy chalcone, it is special
Levy and be：Described 3,4- dimethoxy-acetophenones and the mol ratio of TMB is 1:5～5:1.
3. 3,4,5- trimethoxies -3 of one kind as claimed in claim 1 ', the preparation method of 4 '-dimethoxy chalcone, it is special
Levy and be：Described 3,4- dimethoxy-acetophenones and the mol ratio of strong basic ion liquid is 1:1～10.
4. 3,4,5- trimethoxies -3 of one kind as claimed in claim 1 ', the preparation method of 4 '-dimethoxy chalcone, it is special
Levy and be：Described strong basic ion liquid is： Or 。
5. 3,4,5- trimethoxies -3 of one kind as claimed in claim 1 ', the preparation method of 4 '-dimethoxy chalcone, it is special
Levy and be：Described strong basic ion liquid is：.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611117585.0A CN106588613A (en) | 2016-12-07 | 2016-12-07 | Method for preparing 3,4,5-triethoxy-3',4'-dimethoxy chalcone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611117585.0A CN106588613A (en) | 2016-12-07 | 2016-12-07 | Method for preparing 3,4,5-triethoxy-3',4'-dimethoxy chalcone |
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| CN106588613A true CN106588613A (en) | 2017-04-26 |
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| CN201611117585.0A Pending CN106588613A (en) | 2016-12-07 | 2016-12-07 | Method for preparing 3,4,5-triethoxy-3',4'-dimethoxy chalcone |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110078606A (en) * | 2019-06-05 | 2019-08-02 | 郑州大学 | A method of chalcone is catalyzed and synthesized based on alkali ionic liquid is solvent-free |
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|---|---|---|---|---|
| WO2003002502A1 (en) * | 2001-06-26 | 2003-01-09 | Exxonmobil Research And Engineering Company | Process for conducting aldol condensation reactions in ionic liquid media |
| CN101289378A (en) * | 2007-04-18 | 2008-10-22 | 中国科学院大连化学物理研究所 | A method for synthesizing chalcones and derivatives thereof using ionic liquids |
| CN105967991A (en) * | 2016-05-12 | 2016-09-28 | 哈尔滨医科大学 | Compound with antitumor activity and preparation method and application of compound |
-
2016
- 2016-12-07 CN CN201611117585.0A patent/CN106588613A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003002502A1 (en) * | 2001-06-26 | 2003-01-09 | Exxonmobil Research And Engineering Company | Process for conducting aldol condensation reactions in ionic liquid media |
| CN101289378A (en) * | 2007-04-18 | 2008-10-22 | 中国科学院大连化学物理研究所 | A method for synthesizing chalcones and derivatives thereof using ionic liquids |
| CN105967991A (en) * | 2016-05-12 | 2016-09-28 | 哈尔滨医科大学 | Compound with antitumor activity and preparation method and application of compound |
Non-Patent Citations (1)
| Title |
|---|
| SÒNIA ABELLÓ等: "Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions", 《CHEM. COMMUN.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110078606A (en) * | 2019-06-05 | 2019-08-02 | 郑州大学 | A method of chalcone is catalyzed and synthesized based on alkali ionic liquid is solvent-free |
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Application publication date: 20170426 |