CN114920617A - Method for preparing polysubstituted naphthalene derivative - Google Patents
Method for preparing polysubstituted naphthalene derivative Download PDFInfo
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- CN114920617A CN114920617A CN202210490138.9A CN202210490138A CN114920617A CN 114920617 A CN114920617 A CN 114920617A CN 202210490138 A CN202210490138 A CN 202210490138A CN 114920617 A CN114920617 A CN 114920617A
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- 150000002790 naphthalenes Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 229940126062 Compound A Drugs 0.000 claims abstract description 14
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000004440 column chromatography Methods 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- 239000011968 lewis acid catalyst Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 8
- 229960001701 chloroform Drugs 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 14
- 239000002994 raw material Substances 0.000 abstract description 7
- 125000004429 atom Chemical group 0.000 abstract description 4
- 125000000524 functional group Chemical group 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 238000005273 aeration Methods 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- -1 3-benzyl-3-phenylcyclobutane-1-one Chemical compound 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SKVBYDAXKGWKPA-UHFFFAOYSA-N 3,3-dibenzylcyclobutan-1-one Chemical compound C(C1=CC=CC=C1)C1(CC(C1)=O)CC1=CC=CC=C1 SKVBYDAXKGWKPA-UHFFFAOYSA-N 0.000 description 1
- 238000010917 Friedel-Crafts cyclization Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2076—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by a transformation in which at least one -C(=O)- moiety is eliminated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
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- 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 a polysubstituted naphthalene derivative, which comprises the following steps: mixing a compound A with a catalyst and a solvent, and heating until the reaction is complete to obtain a reaction solution, wherein the structural formula of the compound A is as follows:
wherein R1 is alkyl, substituted phenyl or benzyl, R2 is hydrogen atom or methyl, Ar is substituted phenyl or naphthyl; and concentrating the reaction liquid under reduced pressure to remove the solvent, and separating and purifying to obtain the required product. The method for preparing the polysubstituted naphthalene derivative has the advantages of simple reaction conditions, cheap and easily obtained raw materials and catalyst, good universality of the reacted functional group, and only waterThe by-product of (2) is easy to separate, has higher atom economy and environmental friendliness, and provides a simple and efficient way for synthesizing the polysubstituted naphthalene derivative.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing a polysubstituted naphthalene derivative.
Background
Polysubstituted naphthalene derivatives are present in many natural products and bioactive components and have recently received much attention in the design of chiral catalysts and advanced functional materials. Therefore, the research and development of a novel, efficient and useful synthesis method of the polysubstituted naphthalene derivative is of great significance. In recent years, Lewis acid is developed to catalyze Friedel-Crafts cyclization reaction, and polysubstituted naphthalene derivatives can be constructed. For example, Wang et al synthesized polysubstituted naphthalene derivatives by two serial electrophilic cyclization reactions starting from 4-alkynol and benzene (Chang, M.Y.; Huang, Y.H.; Wang, H.S. tetrahedron.2016,72(15), 1888-substituted 1895.). Hu et al prepared polysubstituted naphthalene derivatives by a serial aldol condensation \ Friedel-Crafts reaction using 1, 2-diarylethanone and acetophenone as starting materials under acid acceleration (Li, H.C.; Shan, L.D.; Min, L.; Weng, Y.X.; Wang, X.Y.; Hu Y.F.the Journal of Organic chemistry.2021,86(21), 15011-15019.).
However, the above method has many limitations such as the need for a stoichiometric amount of catalyst, low product yield, limited functional groups, and the need to add an excessive amount of the second component to the reaction, resulting in a decrease in atom economy.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for preparing polysubstituted naphthalene derivatives, which has the advantages of simple operation, high yield, wide application range of functional groups, and high atom economy.
In order to achieve the purpose, the technical scheme of the invention is realized as follows:
a method for preparing polysubstituted naphthalene derivative, the reaction principle is shown in figure 1, and the method comprises the following steps:
s1: mixing a compound A with a catalyst and a solvent, heating until the reaction is completed to obtain a reaction liquid, wherein the compound A is synthesized according to a method of documents (Gao, J.; Liu, C.; Li, Z.; Liang, H.; Ao, Y.; Zhao, J.; Liu, Y. organic letters.2020,22(10), 3993-:
wherein R1 is alkyl, substituted phenyl or benzyl,r2 is hydrogen atom or methyl, Ar is substituted phenyl or naphthyl;
s2: and concentrating the reaction liquid under reduced pressure to remove the solvent, and separating and purifying to obtain the required product.
Further, the catalyst is a lewis acid catalyst.
Further, the catalyst comprises FeCl 3 、AgSbF 6 、AgNTf 2 、AlCl 3 、Cu(OTf) 2 、ZnCl 2 、Zn(OTf) 2 Or CuCl 2 To (3) is provided.
Further, the solvent comprises one of toluene, tetrahydrofuran, dioxane, chlorobenzene, chloroform or dichloromethane.
Further, in the step S1, the reaction temperature is 60-110 ℃, and the reaction time is 12-24 h.
Further, the molar ratio of the compound A to the catalyst is 1: 0.1-0.2.
Further, the separation and purification method in step S2 is column chromatography or recrystallization.
Further, a developing solvent used for column chromatography separation is a mixture of petroleum ether and ethyl acetate; preferably, the volume ratio of petroleum ether to ethyl acetate is 50-100: 1.
Further, the solvent used for recrystallization is petroleum ether; preferably, the recrystallization time is 12 to 24 hours.
Further, the method comprises the following steps:
s1: mixing a compound A with a catalyst and a solvent, heating to 60-110 ℃, and reacting for 12-24h to obtain a reaction solution, wherein the compound A has a structural formula as follows:
wherein R1 is alkyl, substituted phenyl or benzyl, R2 is hydrogen atom or methyl, Ar is substituted phenyl or naphthyl, and the catalyst is Cu (OTf) 2 The solvent is chlorobenzene, and the molar ratio of the compound A to the catalyst is 1: 0.1;
s2: and (3) concentrating the reaction solution under reduced pressure to remove the solvent, and separating and purifying by column chromatography to obtain the required product.
Compared with the prior art, the method for preparing the polysubstituted naphthalene derivative has the following advantages:
the method for preparing the polysubstituted naphthalene derivative has the advantages of simple reaction conditions, cheap and easily-obtained raw materials and catalysts, good universality of the reacted functional groups, water which is a unique byproduct and is easy to separate, higher atom economy and environmental friendliness, and provides a simple and efficient way for synthesizing the polysubstituted naphthalene derivative.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention, illustrate embodiments of the invention and together with the description serve to explain the invention and do not constitute a limitation of the invention. In the drawings:
FIG. 1 is a schematic diagram showing a reaction principle of a method for preparing a polysubstituted naphthalene derivative according to an embodiment of the present invention;
FIG. 2 is a nuclear magnetic hydrogen spectrum of a product produced in example 1 of the present invention;
FIG. 3 is a nuclear magnetic carbon spectrum of the product prepared in example 1 of the present invention;
FIG. 4 is a nuclear magnetic hydrogen spectrum of the product produced in example 2 of the present invention;
FIG. 5 is a nuclear magnetic carbon spectrum of the product prepared in example 2 of the present invention;
FIG. 6 is a nuclear magnetic hydrogen spectrum of a product produced in example 3 of the present invention;
FIG. 7 is a nuclear magnetic carbon spectrum of the product prepared in example 3 of the present invention;
FIG. 8 is a nuclear magnetic hydrogen spectrum of a product produced in example 4 of the present invention;
FIG. 9 is a nuclear magnetic carbon spectrum of the product prepared in example 4 of the present invention;
FIG. 10 is a nuclear magnetic hydrogen spectrum of a product produced in example 5 of the present invention;
FIG. 11 is a nuclear magnetic carbon spectrum of the product prepared in example 5 of the present invention.
Detailed Description
Unless defined otherwise, technical terms used in the following examples have the same meanings as commonly understood by one of ordinary skill in the art to which the present invention belongs. The test reagents used in the following examples, unless otherwise specified, are all conventional biochemical reagents; the experimental methods are conventional methods unless otherwise specified.
The present invention will be described in detail with reference to the following examples and accompanying drawings.
Example 1
The reaction principle in this example is shown in formula 1, adding Cu (OTf) into a 25 ml reaction tube 2 (10.85mg,0.03mmol) and 3-benzyl-3-phenylcyclobutane-1-one (70.9mg,0.30mmol), after aeration chlorobenzene (3mL) was added by syringe under aeration, and the mixed solution was stirred at 110 ℃ for 24 hours. Monitoring the reaction by TLC, after the raw materials are completely reacted, concentrating under reduced pressure to remove solvent, separating and purifying by column chromatography to obtain yellow solid, and purifying by column chromatography 1 H NMR (as shown in FIG. 2), 13 CNMR (as shown in fig. 3) technique, high resolution mass spectrometric detection, determined structure 1, weighed weight 60.9 mg, calculated yield 93%, reaction represented by the following equation:
example 2
The reaction principle in this example is shown in formula 2, adding Cu (OTf) into a 25 ml reaction tube 2 (10.85mg,0.03mmol) and 3- (4-chlorobenzyl) -3- (4-methylphenyl) cyclobutane-1-one (85.4mg,0.30mmol), after aeration chlorobenzene (3mL) was added by syringe under aeration, and the mixture was stirred at 110 ℃ for 24 hours. Monitoring reaction by TLC, concentrating under reduced pressure to remove solvent after the raw materials completely react, separating and purifying by column chromatography to obtain yellow solid, and purifying by column chromatography 1 H NMR (as shown in FIG. 4), 13 C NMR (as shown in fig. 5) technique, high resolution mass spectrometric detection, determines the structure as formula 2, weighs 78.4 mg, and has a calculated yield of 98%, and the reaction can be represented by the following equation:
example 3
The reaction principle in this example is shown in formula 3, adding Cu (OTf) into a 25 ml reaction tube 2 (10.85mg,0.03mmol) and 3-benzyl-3- (4-bromophenyl) cyclobutane-1-one (94.5mg,0.30mmol), after aeration, chlorobenzene (3mL) was added by syringe under aeration, and the mixture was stirred at 110 ℃ for 24 hours. Monitoring reaction by TLC, concentrating under reduced pressure to remove solvent after the raw materials completely react, separating and purifying by column chromatography to obtain white solid, and purifying by TLC 1 H NMR (shown in FIG. 6), 13 C NMR (as shown in FIG. 7) technique, high resolution mass spectrometry detection, and determination of structure
Formula 3, weighing 80.2 mg, calculated 90% yield, the reaction can be represented by the following equation:
example 4
The reaction principle in this example is shown in formula 4, and Cu (OTf) is added into a 25 ml reaction tube 2 (10.85mg,0.03mmol) and 3-benzyl-3-isobutylcyclobutane-1-one (64.9mg,0.30mmol), after aeration chlorobenzene (3mL) was added by syringe under aeration, and the mixed solution was stirred at 110 ℃ for 24 hours. Monitoring reaction by TLC, concentrating under reduced pressure to remove solvent after the raw materials completely react, separating and purifying by column chromatography to obtain colorless oily liquid 1 H NMR (as shown in FIG. 8), 13 C NMR (as shown in fig. 9) technique, high resolution mass spectrometric detection, determined structure 4, weighed 42.8 mg, calculated yield 72%, and reaction represented by the following equation:
example 5
Reaction in the present exampleThe principle is shown in formula 5, and Cu (OTf) is added into a 25 ml reaction tube 2 (10.85mg,0.03mmol) and 3, 3-dibenzylcyclobutane-1-one (75.1mg,0.30mmol), after aeration chlorobenzene (3mL) was added by syringe under aeration, and the mixture was stirred at 110 ℃ for 24 hours. Monitoring reaction by TLC, concentrating under reduced pressure to remove solvent after the raw materials completely react, separating and purifying by column chromatography to obtain yellow solid, and purifying by column chromatography 1 H NMR (shown in FIG. 10), 13 C NMR (as shown in FIG. 11) technique, high resolution mass spectrometric detection, determined structure 5, weighed weight 69.1 mg, calculated yield > 99%, and reaction represented by the following equation:
comparative example
The difference from example 1 is that in the comparative example, Cu (OTf) was not added 2 Otherwise, the procedure was the same as in example 1, and it was found that a polysubstituted naphthalene derivative could not be obtained.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A method for preparing a polysubstituted naphthalene derivative, comprising the steps of:
s1: mixing a compound A with a catalyst and a solvent, and heating until the reaction is complete to obtain a reaction solution, wherein the structural formula of the compound A is as follows:
wherein R1 is alkyl, substituted phenyl or benzyl, R2 is hydrogen atom or methyl, Ar is substituted phenyl or naphthyl;
s2: and concentrating the reaction liquid under reduced pressure to remove the solvent, and separating and purifying to obtain the required product.
2. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: the catalyst is a lewis acid catalyst.
3. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: the catalyst comprises FeCl 3 、AgSbF 6 、AgNTf 2 、AlCl 3 、Cu(OTf) 2 、ZnCl 2 、Zn(OTf) 2 Or CuCl 2 One kind of (1).
4. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: the solvent comprises one of toluene, tetrahydrofuran, dioxane, chlorobenzene, trichloromethane or dichloromethane.
5. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: in the step S1, the reaction temperature is 60-110 ℃, and the reaction time is 12-24 h.
6. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: the mol ratio of the compound A to the catalyst is 1: 0.1-0.2.
7. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: the separation and purification method in the step S2 is column chromatography separation or recrystallization.
8. The method for producing a polysubstituted naphthalene derivative according to claim 7, wherein: the developing solvent used for column chromatography separation is a mixture of petroleum ether and ethyl acetate; preferably, the volume ratio of petroleum ether to ethyl acetate is 50-100: 1.
9. The method for producing a polysubstituted naphthalene derivative according to claim 7, wherein: the solvent used for recrystallization is petroleum ether; preferably, the recrystallization time is 12 to 24 hours.
10. The method for preparing polysubstituted naphthalene derivatives according to any one of claims 1 to 9, comprising the steps of:
s1: mixing a compound A with a catalyst and a solvent, heating to 60-110 ℃, and reacting for 12-24h to obtain a reaction solution, wherein the structural formula of the compound A is as follows:
wherein R1 is alkyl, substituted phenyl or benzyl, R2 is hydrogen atom or methyl, Ar is substituted phenyl or naphthyl, and the catalyst is Cu (OTf) 2 The solvent is chlorobenzene, and the molar ratio of the compound A to the catalyst is 1: 0.1;
s2: and (3) concentrating the reaction solution under reduced pressure to remove the solvent, and separating and purifying by column chromatography to obtain the required product.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112920033A (en) * | 2021-01-29 | 2021-06-08 | 长春工业大学 | Preparation method of o-alkynyl phenylcyclobutanone and preparation method of naphthalenone |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112920033A (en) * | 2021-01-29 | 2021-06-08 | 长春工业大学 | Preparation method of o-alkynyl phenylcyclobutanone and preparation method of naphthalenone |
Non-Patent Citations (3)
| Title |
|---|
| MIN ZHANG ET AL.: "Lewis Acid Catalyzed Ring-Opening Reaction of Cyclobutanones towards Conjugated Enones", 《EUROPEAN JOURNAL OF ORGANIC CHEMISTRY》, vol. 2021, no. 45, pages 6111 - 6114 * |
| 张敏: "路易斯酸催化的环丁酮类化合物的开环反应研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》, no. 2022, pages 014 - 13 * |
| 钱艳艳 等: "无铜参与的钯催化Sonogashira偶联反应合成β-(2-苯乙炔基)环丁酮类化合物", 《分子科学学报》, vol. 36, no. 5, pages 368 - 375 * |
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