CN114920617B - Method for preparing polysubstituted naphthalene derivative - Google Patents
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- CN114920617B CN114920617B CN202210490138.9A CN202210490138A CN114920617B CN 114920617 B CN114920617 B CN 114920617B CN 202210490138 A CN202210490138 A CN 202210490138A CN 114920617 B CN114920617 B CN 114920617B
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- 150000002790 naphthalenes Chemical class 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 229940126062 Compound A Drugs 0.000 claims abstract description 12
- 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 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 15
- 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
- 238000004440 column chromatography Methods 0.000 claims description 11
- 239000003208 petroleum Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 4
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 9
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 14
- 125000000524 functional group Chemical group 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000004429 atom Chemical group 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 abstract description 3
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005273 aeration Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- -1 3-benzyl-3-phenylcyclobutan-1-one Chemical compound 0.000 description 4
- 238000004896 high resolution mass spectrometry Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 238000010917 Friedel-Crafts cyclization Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 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
- 238000012544 monitoring process Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910001544 silver hexafluoroantimonate(V) Inorganic materials 0.000 description 1
- HSYLTRBDKXZSGS-UHFFFAOYSA-N silver;bis(trifluoromethylsulfonyl)azanide Chemical compound [Ag+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F HSYLTRBDKXZSGS-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
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 a polysubstituted naphthalene derivative, which comprises the following steps: mixing and heating the compound A, a catalyst and a solvent 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; the reaction solution is decompressed, concentrated to remove the solvent, and then separated and purified to obtain the required product. The method for preparing the polysubstituted naphthalene derivative has the advantages of simple reaction conditions, low-cost and easily available raw materials and catalysts, good universality of the reacted functional groups, water is the only byproduct, easy separation and high 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, which have recently also received attention in the design of chiral catalysts and advanced functional materials. Therefore, the development of a novel, efficient and useful synthesis method of the polysubstituted naphthalene derivative has important significance. In recent years, a type of Lewis acid catalyzed Friedel-Crafts cyclization reaction is developed, and polysubstituted naphthalene derivatives can be constructed. For example, wang et al synthesized polysubstituted naphthalene derivatives by two cascade electrophilic cyclization reactions starting with 4-alkynol and benzene (Chang, M.Y.; huang, Y.H.; wang, H.S. tetrahedron.2016,72 (15)), 1888-1895. Hu et al prepared a polysubstituted naphthalene derivative by using 1, 2-diaryl ethanone and acetophenone as raw materials and conducting serial aldol condensation/Friedel-Crafts reaction under the promotion of acid (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-mentioned methods have many limitations such as the need for a stoichiometric amount of catalyst, low product yield, limited functional groups, and the necessity of adding an excessive amount of the second component in the reaction, resulting in reduced atomic economy.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for preparing a polysubstituted naphthalene derivative, which has the advantages of simple operation, high yield, wide application range of functional groups and high atom economy.
In order to achieve the above purpose, the technical scheme of the invention is realized as follows:
A method for preparing polysubstituted naphthalene derivative, the reaction principle of which is shown in figure 1, comprises the following steps:
S1: the compound a, which is synthesized according to the method of literature (Gao, j.; liu, c.; li, z.; liang, h.; ao, y.; zhao, j.; liu, y. Organic letters 2020,22 (10), 3993-3999.), has the structural formula: Wherein R1 is alkyl, substituted phenyl or benzyl, R2 is hydrogen atom or methyl, ar is substituted phenyl or naphthyl;
S2: the reaction solution is decompressed, concentrated to remove the solvent, and then separated and purified to obtain the required product.
Further, the catalyst is a lewis acid catalyst.
Further, the catalyst includes one of FeCl3、AgSbF6、AgNTf2、AlCl3、Cu(OTf)2、ZnCl2、Zn(OTf)2 or CuCl 2.
Further, the solvent comprises one of toluene, tetrahydrofuran, dioxane, chlorobenzene, chloroform or dichloromethane.
Further, the reaction temperature in the step S1 is 60-110 ℃ and the reaction time is 12-24h.
Further, the molar ratio of the compound A to the catalyst is 1:0.1-0.2.
Further, the separation and purification method in the step S2 is column chromatography separation or recrystallization.
Further, the developing agent 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 12-24 hours.
Further, the method comprises the following steps:
s1: mixing and heating the compound A, a catalyst and a solvent to 60-110 ℃ for reacting for 12-24 hours 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, 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: the reaction solution was concentrated under reduced pressure to remove the solvent, and then the desired product was obtained by separation and purification by column chromatography.
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, low-cost and easily available raw materials and catalysts, good universality of the reacted functional groups, water is the only byproduct, easy separation and high 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 and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention. In the drawings:
FIG. 1 is a schematic illustration of the 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 resonance spectrum of the product prepared in example 1 of the present invention;
FIG. 3 is a nuclear magnetic resonance spectrum of the product prepared in example 1 of the present invention;
FIG. 4 is a nuclear magnetic resonance spectrum of the product prepared in example 2 of the present invention;
FIG. 5 is a nuclear magnetic resonance spectrum of the product prepared in example 2 of the present invention;
FIG. 6 is a nuclear magnetic resonance spectrum of the product prepared in example 3 of the present invention;
FIG. 7 is a nuclear magnetic resonance spectrum of the product prepared in example 3 of the present invention;
FIG. 8 is a nuclear magnetic resonance spectrum of the product prepared in example 4 of the present invention;
FIG. 9 is a nuclear magnetic resonance spectrum of the product prepared in example 4 of the present invention;
FIG. 10 is a nuclear magnetic resonance spectrum of the product prepared in example 5 of the present invention;
FIG. 11 is a nuclear magnetic resonance 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 meaning as commonly understood by one of ordinary skill in the art to which the present invention pertains. 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 drawings.
Example 1
The reaction principle in this example is shown in formula 1, cu (OTf) 2 (10.85 mg,0.03 mmol) and 3-benzyl-3-phenylcyclobutan-1-one (70.9 mg,0.30 mmol) were added to a 25-mL reaction tube, chlorobenzene (3 mL) was added via syringe under aeration after aeration, and the mixed solution was stirred at 110℃for 24 hours. The reaction was monitored by TLC, after the starting materials were reacted completely, the solvent was removed by concentration under reduced pressure, and isolated and purified by column chromatography to give a yellow solid which was detected by 1 H NMR (as shown in fig. 2), 13 CNMR (as shown in fig. 3) techniques, high resolution mass spectrometry to determine the structure as formula 1, weighing 60.9 mg, and calculating the yield as 93%, the reaction was expressed by the following equation:
Example 2
The reaction principle in this example is shown in formula 2, cu (OTf) 2 (10.85 mg,0.03 mmol) and 3- (4-chlorobenzyl) -3- (4-methylphenyl) cyclobutan-1-one (85.4 mg,0.30 mmol) were added to a 25-mL reaction tube, chlorobenzene (3 mL) was added via syringe under aeration after aeration, and the mixed solution was stirred at 110℃for 24 hours. The reaction was monitored by TLC, after the starting materials were reacted completely, the solvent was removed by concentration under reduced pressure, and isolated and purified by column chromatography to give a yellow solid which was detected by 1 H NMR (as shown in fig. 4), 13 C NMR (as shown in fig. 5) techniques, high resolution mass spectrometry to determine the structure as formula 2, weighing 78.4 mg, and calculated yield as 98%, the reaction was expressed by the following equation:
example 3
The reaction principle in this example is shown in formula 3, cu (OTf) 2 (10.85 mg,0.03 mmol) and 3-benzyl-3- (4-bromophenyl) cyclobutan-1-one (94.5 mg,0.30 mmol) were added to a 25-mL reaction tube, chlorobenzene (3 mL) was added via syringe under aeration after aeration, and the mixed solution was stirred at 110℃for 24 hours. Monitoring the reaction by TLC, concentrating under reduced pressure to remove solvent after the raw materials are reacted completely, separating and purifying by column chromatography to obtain white solid, and detecting the solid by 1 H NMR (shown in figure 6), 13 C NMR (shown in figure 7) and high resolution mass spectrum to determine the structure as
Formula 3, weighing 80.2 mg, calculated yield 90%, the reaction can be expressed by the following equation:
Example 4
The reaction principle in this example is shown in formula 4, cu (OTf) 2 (10.85 mg,0.03 mmol) and 3-benzyl-3-isobutyl-cyclobutan-1-one (64.9 mg,0.30 mmol) are added to a 25 mL reaction tube, chlorobenzene (3 mL) is added via syringe under aeration after aeration, and the mixed solution is stirred at 110℃for 24 hours. The reaction was monitored by TLC, after the starting materials were reacted completely, the solvent was removed by concentration under reduced pressure, and the colorless oily liquid was isolated and purified by column chromatography, and the liquid was detected by 1 H NMR (as shown in fig. 8), 13 C NMR (as shown in fig. 9) and high resolution mass spectrometry to determine the structure as formula 4, weighing 42.8 mg, and the calculated yield was 72%, and the reaction was expressed by the following equation:
example 5
The reaction principle in this example is shown in formula 5, cu (OTf) 2 (10.85 mg,0.03 mmol) and 3, 3-dibenzylcyclobutane-1-one (75.1 mg,0.30 mmol) were added to a 25-mL reaction tube, chlorobenzene (3 mL) was added via syringe under aeration after aeration, and the mixed solution was stirred at 110℃for 24 hours. The reaction was monitored by TLC, after the starting materials were reacted completely, the solvent was removed by concentration under reduced pressure, and isolated and purified by column chromatography to give a yellow solid which was detected by 1 H NMR (as shown in fig. 10), 13 C NMR (as shown in fig. 11) techniques, high resolution mass spectrometry to determine the structure as formula 5, weighing 69.1 mg, and calculating the yield >99%, the reaction was expressed by the following equation:
Comparative example
The difference from example 1 is that Cu (OTf) 2 was not added in the comparative example, and the other steps were the same as in example 1, and the multi-substituted naphthalene derivative could not be obtained by detection.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (9)
1. A process for preparing a polysubstituted naphthalene derivative, comprising the steps of:
S1: mixing and heating the compound A, a catalyst and a solvent until the reaction is complete to obtain a reaction solution, wherein the structural formula of the compound A is as follows:
s2: concentrating the reaction solution under reduced pressure to remove the solvent, and separating and purifying to obtain a required product;
The catalyst is Cu (OTf) 2; the solvent is chlorobenzene;
R1 is phenyl, R2 is hydrogen atom, ar is phenyl, and the structural formula of the product is:
Or R1 is 4-methylphenyl, R2 is hydrogen atom, ar is 4-chlorophenyl, and the structural formula of the product is:
or R1 is 4-bromophenyl, R2 is hydrogen atom, ar is phenyl, and the structural formula of the product is:
Or R1 is isobutyl, R2 is hydrogen atom, ar is phenyl, and the structural formula of the product is:
or R1 is benzyl, R2 is hydrogen atom, ar is phenyl, and the structural formula of the product is:
2. 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 12-24h.
3. The method for producing a polysubstituted naphthalene derivative according to claim 1, wherein: the molar ratio of the compound A to the catalyst is 1:0.1-0.2.
4. 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.
5. The method for producing a polysubstituted naphthalene derivative according to claim 4, wherein: the developing agent used for column chromatography separation is a mixture of petroleum ether and ethyl acetate.
6. The method for producing a polysubstituted naphthalene derivative according to claim 5, wherein: the volume ratio of petroleum ether to ethyl acetate is 50-100:1.
7. The method for producing a polysubstituted naphthalene derivative according to claim 4, wherein: the solvent used for recrystallization is petroleum ether.
8. The method for producing a polysubstituted naphthalene derivative according to claim 4, wherein: the recrystallization time is 12-24h.
9. The process for preparing a polysubstituted naphthalene derivative according to any one of claims 1 to 4, comprising the steps of:
s1: mixing and heating the compound A, a catalyst and a solvent to 60-110 ℃ for reacting for 12-24 hours to obtain a reaction solution, wherein the structural formula of the compound A is as follows: the catalyst is Cu (OTf) 2, the solvent is chlorobenzene, and the mol ratio of the compound A to the catalyst is 1:0.1;
s2: the reaction solution was concentrated under reduced pressure to remove the solvent, and then the desired product was obtained by separation and purification by column chromatography.
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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 |
|---|---|---|---|---|
| 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 |
|---|
| Lewis Acid Catalyzed Ring-Opening Reaction of Cyclobutanones towards Conjugated Enones;Min Zhang et al.;《European Journal of Organic Chemistry》;第2021卷(第45期);6111-6114 * |
| 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;钱艳艳 等;《分子科学学报》;第36卷(第5期);368-375 * |
| 路易斯酸催化的环丁酮类化合物的开环反应研究;张敏;《中国优秀硕士学位论文全文数据库 工程科技I辑》(第2022年第10期期);B014-13 * |
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