CN117263872A - Synthesis method of 2-acetylpyrazine - Google Patents
Synthesis method of 2-acetylpyrazine Download PDFInfo
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- CN117263872A CN117263872A CN202311297441.8A CN202311297441A CN117263872A CN 117263872 A CN117263872 A CN 117263872A CN 202311297441 A CN202311297441 A CN 202311297441A CN 117263872 A CN117263872 A CN 117263872A
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- acetylpyrazine
- synthesizing
- pyrazine
- synthesis method
- oxidant
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- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000001308 synthesis method Methods 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 23
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims abstract description 13
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007800 oxidant agent Substances 0.000 claims abstract description 10
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- 230000002194 synthesizing effect Effects 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical group NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract description 6
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 229940107700 pyruvic acid Drugs 0.000 abstract description 2
- 238000003860 storage Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- DJQOOSBJCLSSEY-UHFFFAOYSA-N Acipimox Chemical compound CC1=CN=C(C(O)=O)C=[N+]1[O-] DJQOOSBJCLSSEY-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000723382 Corylus Species 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- -1 acetyl free radical Chemical class 0.000 description 1
- 229960003526 acipimox Drugs 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 229960001381 glipizide Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- CRBOSZMVDHYLJE-UHFFFAOYSA-N methyl 5-methylpyrazine-2-carboxylate Chemical compound COC(=O)C1=CN=C(C)C=N1 CRBOSZMVDHYLJE-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Abstract
The invention relates to the technical field of chemical organic synthesis, in particular to a synthesis method of 2-acetylpyrazine. The synthesis method comprises the steps of adding raw materials of pyrazine and vinyl n-butyl ether into an organic solvent, adding an oxidant and trifluoroacetic acid, and reacting to prepare 2-acetylpyrazine. The synthesis method of 2-acetylpyrazine provided by the invention has the advantages of few reaction steps, mild reaction conditions and high product purity, and is suitable for industrial production. Meanwhile, the method uses n-butyl vinyl ether as an acetyl precursor raw material, and overcomes the defects of low yield and severe storage and transportation conditions of acetaldehyde and pyruvic acid as acetyl precursors.
Description
Technical Field
The invention relates to the technical field of chemical organic synthesis, in particular to a synthesis method of 2-acetylpyrazine.
Background
The disclosure of this background section is only intended to increase the understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art already known to those of ordinary skill in the art.
2-acetylpyrazine is an important flavorant that is found in fried potatoes, sesame oil, peanuts, hazelnuts, almonds and coffee, and has a popcorn taste, a roasted taste. Is suitable for baked food, peanut, sesame, meat and tobacco at the earliest. Meanwhile, the 2-acetylpyrazine is also used as an important synthetic raw material for synthesizing intermediates of novel medicines such as glipizide, acipimox, 5-methyl pyrazine-2-carboxylic acid methyl ester and the like.
In the prior art, the method for producing the 2-acetylpyrazine mainly comprises an oxidation method, a metal reagent method and a multi-step method. Among them, the oxidation method needs to be carried out at a low temperature (3-5 ℃), the requirements on the reaction are relatively high, and the final yield is relatively low. The metal reagent method is divided into an organic lithium reagent method and a format reagent method, and the organic lithium reagent method has the main defects that the organic lithium reagent is expensive, inflammable and explosive, and the reaction needs to be carried out at low temperature; the grignard reagent method is safe to operate, but needs to be performed at a low temperature, and the yield is difficult to increase. The multi-step method generally requires more than 4 steps of reactions to be obtained synthetically, and has complicated steps and poor operability. Therefore, a method for synthesizing 2-acetylpyrazine is needed, which is safe in operation, simple in operation and high in yield.
Disclosure of Invention
In order to overcome the problems, the invention provides a synthesis method of 2-acetylpyrazine, which has few reaction steps, mild reaction conditions and high product purity, and is suitable for industrial production. Meanwhile, the method uses n-butyl vinyl ether as an acetyl precursor raw material, and overcomes the defects of low yield and severe storage and transportation conditions of acetaldehyde and pyruvic acid as acetyl precursors.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
the invention provides a synthesis method of 2-acetylpyrazine, which comprises the following steps:
adding raw materials of pyrazine and vinyl n-butyl ether into an organic solvent, adding an oxidant and trifluoroacetic acid, and reacting to prepare the 2-acetylpyrazine.
In situ decomposition of n-butyl vinyl ether in the presence of TFA to form acetaldehyde, then SO 4 - · Selectively seizing hydrogen atoms from acetaldehyde to obtain acetylAnd adding the free radical and acetyl free radical into the protonated pyrazine ring to obtain a free radical cation, and finally, under the promotion effect of an oxidant in a system, obtaining the 2-acetyl pyrazine.
According to a further technical scheme, the reaction is carried out in an inert gas environment, wherein the inert gas is nitrogen or argon.
According to a further technical scheme, the organic solvent is one of dichloromethane, dichloroethane, dimethyl sulfoxide, acetonitrile or N, N-dimethylformamide, and further preferably dimethyl sulfoxide.
According to a further technical scheme, the oxidant is sodium persulfate, potassium persulfate or ammonium persulfate.
According to a further technical scheme, the molar ratio of the pyrazine to the vinyl n-butyl ether to the oxidant to the trifluoroacetic acid is 1:1.0-3.5:1.0-4.0:1.0-3.0, and is preferably 1:2:2:2.
According to a further technical scheme, the reaction temperature is 40-100 ℃, preferably 40-70 ℃; the reaction time is 20 to 30 hours, preferably 24 hours.
The invention has the beneficial effects that:
(1) The invention provides a synthesis method of 2-acetyl pyrazine, which takes pyrazine and vinyl n-butyl ether as raw materials, and oxidant and trifluoroacetic acid are added to react at 40-100 ℃ to generate 2-acetyl pyrazine.
(2) The synthesis method of the 2-acetylpyrazine has the advantages that the yield of the product is higher and can reach more than 80%, meanwhile, the purity of the product is up to 98%, and meanwhile, the reaction rate is accelerated.
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.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of 2-acetylpyrazine prepared in example 1 of the present invention.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the invention. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the present invention. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof.
In order to enable those skilled in the art to more clearly understand the technical solutions of the present application, the technical solutions of the present application will be described in detail below with reference to specific embodiments.
Example 1
The synthetic route for 2-acetylpyrazine is shown below:
into a 500mL reaction flask were charged pyrazine (20 g,0.25 mol), n-butyl vinyl ether (50 g,0.5 mol), na under nitrogen atmosphere 2 S 2 O 8 (119 g,0.5 mol), trifluoroacetic acid (TFA) (57 g,0.5 mol) and 200mL of dimethyl sulfoxide. The reaction mixture was stirred rapidly at 60℃for 24h, after which the solvent was distilled off under reduced pressure and 100mL of 1M NaHCO was used 3 The mixture was diluted with aqueous solution and extracted with dichloromethane (2×100 mL), the organic extracts combined and concentrated in vacuo. Mixing petroleum ether and ethyl acetate (volume is 5:1) solventThe product was recrystallized to give 25.6g of white solid with a purity of 98% and a yield of 84%. The nuclear magnetic hydrogen spectrum of the 2-acetylpyrazine prepared in the embodiment is shown in figure 1.
Example 2
The synthetic route for 2-acetylpyrazine is shown below:
into a 500mL reaction flask were charged pyrazine (20 g,0.25 mol), n-butyl vinyl ether (50 g,0.5 mol), na under nitrogen atmosphere 2 S 2 O 8 (119 g,0.5 mol), trifluoroacetic acid (TFA) (57 g,0.5 mol) and 200mL of dimethyl sulfoxide. The reaction mixture was stirred rapidly at 40℃for 24h, after which the solvent was distilled off under reduced pressure and 100mL of 1M NaHCO was used 3 The mixture was diluted with aqueous solution and extracted with dichloromethane (2×100 mL), the organic extracts combined and concentrated in vacuo. The product was recrystallized from a mixed solvent of petroleum ether and ethyl acetate (volume 5:1) to give 21g of white solid with a purity of 97.7% and a yield of 69%. 1 H NMR(500MHz,CDCl 3 )δ9.22(s,1H),8.74(d,,J＝2.4Hz,1H),8.67-8.60(m,1H),2.71(s,3H)。
Example 3
The synthetic route for 2-acetylpyrazine is shown below:
into a 500mL reaction flask were charged pyrazine (20 g,0.25 mol), n-butyl vinyl ether (50 g,0.5 mol), K under nitrogen atmosphere 2 S 2 O 8 (135 g,0.5 mol), trifluoroacetic acid (TFA) (57 g,0.5 mol) and 200mL of dimethyl sulfoxide. The reaction mixture was stirred rapidly at 40℃for 24h, after which the solvent was distilled off under reduced pressure and 100mL of 1M NaHCO was used 3 The mixture was diluted with aqueous solution and extracted with dichloromethane (2×100 mL), the organic extracts combined and concentrated in vacuo. By petroleum ether and acetic acidThe ethyl ester (volume is 5:1) mixed solvent is used for recrystallizing the product to obtain 22g of white solid with the purity of 97 percent and the yield of 72 percent.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for synthesizing 2-acetylpyrazine, comprising:
adding raw materials of pyrazine and vinyl n-butyl ether into an organic solvent, adding an oxidant and trifluoroacetic acid, and reacting to prepare the 2-acetylpyrazine.
2. The method for synthesizing 2-acetylpyrazine of claim 1, wherein the reaction is carried out under an inert gas atmosphere.
3. The method for synthesizing 2-acetylpyrazine of claim 2, wherein said inert gas is nitrogen or argon.
4. The method for synthesizing 2-acetylpyrazine of claim 1, wherein said organic solvent is one of dichloromethane, dichloroethane, dimethyl sulfoxide, acetonitrile or N, N-dimethylformamide.
5. The method for synthesizing 2-acetylpyrazine of claim 4, wherein said organic solvent is dimethyl sulfoxide.
6. The method for synthesizing 2-acetylpyrazine of claim 1, wherein the oxidizing agent is sodium persulfate, potassium persulfate, or ammonium persulfate.
7. The method for synthesizing 2-acetylpyrazine of claim 1, wherein the molar ratio of pyrazine, vinyl-n-butyl ether, oxidant and trifluoroacetic acid is 1:1.0-3.5:1.0-4.0:1.0-3.0.
8. The method for synthesizing 2-acetylpyrazine of claim 7, wherein the molar ratio of pyrazine, vinyl n-butyl ether, oxidant and trifluoroacetic acid is 1:2:2:2.
9. The method for synthesizing 2-acetylpyrazine of claim 1, wherein the reaction temperature is 40-100 ℃ and the reaction time is 20-30 h.
10. The method for synthesizing 2-acetylpyrazine of claim 9, wherein the reaction temperature is 40-70 ℃ and the reaction time is 24 hours.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113089004A (en) * | 2021-04-08 | 2021-07-09 | 华东理工大学 | Method for preparing 2-acetylpyrazine by electrolytic process |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113089004A (en) * | 2021-04-08 | 2021-07-09 | 华东理工大学 | Method for preparing 2-acetylpyrazine by electrolytic process |
Non-Patent Citations (3)
| Title |
|---|
| JIANYANG DONG ET AL.: ""Metal‑, Photocatalyst‑, and Light-Free Minisci C−H Acetylation of N‑Heteroarenes with Vinyl Ethers"", 《ORG. LETT.》, vol. 23, pages 4374 * |
| 王海滨: ""乙酰基吡嗪的合成及应用研究进展"", 《有机化学》, vol. 31, no. 08, pages 1180 - 1187 * |
| 王秀芝: ""非贵金属催化的Minisci酰基化反应及其在香料乙酰基吡嗪合成中的应用"", 《中国优秀硕士学位论文全文数据库 (电子期刊)》, no. 2021, pages 014 - 18 * |
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