CN110372589B - Preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate - Google Patents
Preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate Download PDFInfo
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- CN110372589B CN110372589B CN201910742220.4A CN201910742220A CN110372589B CN 110372589 B CN110372589 B CN 110372589B CN 201910742220 A CN201910742220 A CN 201910742220A CN 110372589 B CN110372589 B CN 110372589B
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- -1 4-tert-butylphenyl Chemical group 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 24
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims abstract description 24
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229940102398 methyl anthranilate Drugs 0.000 claims abstract description 12
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical group O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 2
- DIRRKLFMHQUJCM-UHFFFAOYSA-N (2-aminophenyl)boronic acid Chemical compound NC1=CC=CC=C1B(O)O DIRRKLFMHQUJCM-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241001249193 Artemisia campestris Species 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- SATVLVYEJAZVPV-UHFFFAOYSA-N ac1meepe Chemical compound C12CC=CC2C(C2=3)=CC(C(O)=O)=CC=3C(CCCCC)CCN2C1C1=CC=C(Br)C=C1 SATVLVYEJAZVPV-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010490 three component reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the field of organic chemical synthesis and pharmaceutical synthesis, and particularly relates to a preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate, which comprises the following steps; firstly, methyl anthranilate, benzaldehyde, p-tert-butyl styrene, a catalyst and a solvent are sequentially added into a round-bottom flask, and the mixture is stirred at room temperature for reaction for 16-36 hours. Stopping reaction, standing, and then carrying out column layer separation on the product to obtain a product; the invention widens the synthesis method of the 1,2,3, 4-tetrahydroquinoline and lays a foundation for the application of the 1,2,3, 4-tetrahydroquinoline in the aspect of medicaments.
Description
Technical Field
The invention relates to a preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate, belongs to the field of organic chemical synthesis, and lays a foundation for application of the organic chemical synthesis.
Technical Field
The 1,2,3, 4-tetrahydroquinoline derivative is a heterocyclic compound formed by combining a benzene ring and a nitrogen-containing piperidine six-membered heterocyclic ring, and is a very important N-heterocyclic compound. The research shows that the tetrahydroquinoline derivative has biological activities of resisting bacteria, expelling parasites, resisting viruses, resisting tumors, promoting urination and the like, and can be used for treating diseases such as arteriosclerosis, thrombus, hyperlipidemia, arrhythmia and the like.
For 1,2,3, 4-tetrahydroquinoline derivatives. Nelson and Marsden et al report the synthesis of tetrahydroquinoline derivatives (by using 2-aminophenylboronic acid and alpha, beta-disubstituted enone) under the action of noble metalsChem. Commun., 2014, 50, 10222). However, the reported synthesis method of the 1,2,3, 4-tetrahydroquinoline derivative is complex, the raw material price is expensive, the yield is low, and the cost is increased due to the use of a noble metal catalyst. Later, Bubrin and Beifuss et al reported three-component reaction for synthesizing tetrahydroquinoline derivatives from nitrobenzene, aldehyde and dienophile under the catalysis of iron powder, but the catalyst cannot be recycled (J. Org. Chem. 2015, 80, 2319). Based on the above documents, a room temperature is designedThe preparation method for green synthesis of the 1,2,3, 4-tetrahydroquinoline derivative becomes a focus of attention under the condition, so that a foundation can be laid for the application of the derivative.
Through searching, no published patent literature relevant to the application of the invention is found.
Disclosure of Invention
The invention aims to provide a simple synthesis method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate. The invention utilizes methyl anthranilate, benzaldehyde and p-tert-butyl styrene to react, and synthesizes 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate under the condition of room temperature through heteropoly acid catalysis.
The scheme of the invention is that the preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate is characterized in that:
a preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate, which comprises the following steps; firstly, methyl anthranilate, benzaldehyde, p-tert-butyl styrene, a catalyst and a solvent are sequentially added into a round-bottom flask, and the mixture is stirred at room temperature for reaction for 16-36 hours. Stopping reaction, standing, and then carrying out column layer separation on the product to obtain the product.
The molecular structure of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-carboxylic acid methyl ester is as follows:
the data for methyl 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-carboxylate are characterized as follows:
Mp: 163.5-164.8 ºC; 1H NMR (500 MHz, CDCl3/TMS): 8.44 (s, 1H), 7.95 (d, J = 8.0 Hz, 2H), 7.61 (d, J = 7.0 Hz, 2H), 7.50-7.48 (m, 4H), 7.41(t, J = 7.5 Hz, 1H), 7.31 (d, J = 8.5 Hz, 2H), 6.94 (d, J = 7.5 Hz, 1H), 6.57 (t, J = 7.8 Hz, 1H), 4.88 (dd, J 1 = 3.0 Hz, J 2 = 11.0 Hz, 1H), 4.37 (dd, J 1 = 4.5 Hz, J 2 = 12.5 Hz, 1H), 3.96 (s, 3H), 2.46-2.41 (m, 1H), 2.36-2.29 (m, 1H), 1.49 (s, 9H); 13C NMR (125 MHz, CDCl3/TMS): 169.28, 149.69, 148.09, 143.25, 141.24, 134.37, 129.89, 128.93, 128.35, 127.88, 126.74, 126.45, 125.68, 115.01, 109.62, 56.91, 51.70, 44.53, 40.37, 34.59, 31.53. HRMS (ESI): m/z calcd for C27H30BrNO2[M+H]+: 400.2271, found: 400.2279.
the method has the unique advantage that the synthesis method of the 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate is simple and convenient, can be completed at room temperature, and has high product yield.
Drawings
FIG. 1 is a NMR spectrum of methyl 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-carboxylate;
FIG. 2 is the NMR carbon spectrum of the compound methyl 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-carboxylate.
Detailed Description
The present invention is described in detail below with reference to examples, but the scope of protection is not limited thereto.
4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate and a preparation method thereof, wherein the preparation method comprises the following steps: firstly, sequentially adding methyl anthranilate (10-20 mmol), benzaldehyde (10-20 mmol), p-tert-butylstyrene (40-60 mmol), a solvent (100-200 mmol) and a catalyst (0.5-2 mmol) into a round-bottom flask, stirring at room temperature for reacting for 16-36 hours, stopping reaction, and standing. And (5) performing column chromatography to obtain a product, wherein the yield is 60-91%.
The first embodiment is as follows:
methyl anthranilate (10 mmol), benzaldehyde (10 mmol), p-tert-butylstyrene (40 mmol), solvent (100 mmol) and phosphotungstic acid (0.5 mmol) are sequentially added into a round-bottom flask, stirred at room temperature for reaction for 16 hours, stopped, and then kept stand. The product is obtained by column chromatography, and the yield is 76 percent
Example two:
methyl anthranilate (15 mmol), benzaldehyde (10 mmol), p-tert-butylstyrene (50 mmol), acetonitrile (200 mmol) and phosphotungstic acid (0.5 mmol) were added in this order to a round-bottomed flask, stirred at room temperature for 16 hours, stopped, and allowed to stand. The product is obtained by column chromatography, and the yield is 82 percent
Example three:
methyl anthranilate (20 mmol), benzaldehyde (10 mmol), p-tert-butylstyrene (50 mmol), acetonitrile (200 mmol) and phosphotungstic acid (1 mmol) were sequentially added to a round-bottomed flask, stirred at room temperature for reaction for 20 hours, stopped, and allowed to stand. The product is obtained by column chromatography, and the yield is 87 percent
Example four:
methyl anthranilate (10 mmol), benzaldehyde (20 mmol), p-tert-butylstyrene (60 mmol), acetonitrile (200 mmol) and phosphotungstic acid (2 mmol) were sequentially added to a round-bottomed flask, stirred at room temperature for reaction for 24 hours, stopped, and allowed to stand. The product is obtained by column chromatography, and the yield is 90%.
Example five:
methyl anthranilate (10 mmol), benzaldehyde (20 mmol), p-tert-butylstyrene (60 mmol), acetonitrile (200 mmol) and phosphomolybdic acid (1 mmol) were sequentially added to a round-bottomed flask, and the reaction was stirred at room temperature for 24 hours to stop the reaction and to stand. The product was obtained by column chromatography in 73% yield.
Example six:
methyl anthranilate (10 mmol), benzaldehyde (20 mmol), p-tert-butylstyrene (50 mmol), ethanol (200 mmol) and phosphomolybdic acid (2 mmol) were sequentially added to a round-bottomed flask, and the reaction was stirred at room temperature for 36 hours to stop the reaction and to stand. The product was obtained by column chromatography with a yield of 68%.
Claims (3)
1. A preparation method of 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-methyl formate is characterized by comprising the steps of firstly, sequentially adding methyl anthranilate, benzaldehyde, p-tert-butylstyrene, a catalyst and a solvent into a round-bottom flask, stirring at room temperature for 16-36 hours to react, and then carrying out column-layer separation on a product to obtain a product, wherein the catalyst is phosphotungstic acid.
2. The process for the preparation of methyl 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-carboxylate according to claim 1, wherein: methyl anthranilate: benzaldehyde: p-tert-butylstyrene: solvent: the mass ratio of the catalyst is: 10-20: 10-20: 40-60: 100-200: 0.5-2, and the reaction time is 16-36 h.
3. The process for the preparation of methyl 4- (4-tert-butylphenyl) -2-phenyl-1, 2,3, 4-tetrahydroquinoline-8-carboxylate according to claim 1, wherein: the solvent is acetonitrile.
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| CN103910676B (en) * | 2013-01-04 | 2015-11-18 | 华东师范大学 | A kind of synthetic method of polysubstituted tetrahydro isoquinoline derivative |
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