CN114195713A - 一种催化四氢异喹啉选择性脱氢合成二氢异喹啉的方法 - Google Patents
一种催化四氢异喹啉选择性脱氢合成二氢异喹啉的方法 Download PDFInfo
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- CN114195713A CN114195713A CN202210032924.4A CN202210032924A CN114195713A CN 114195713 A CN114195713 A CN 114195713A CN 202210032924 A CN202210032924 A CN 202210032924A CN 114195713 A CN114195713 A CN 114195713A
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- China
- Prior art keywords
- dihydroisoquinoline
- tetrahydroisoquinoline
- dehydrogenation
- synthesizing
- catalyzing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000006356 dehydrogenation reaction Methods 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 30
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 19
- -1 tetrahydroisoquinoline compound Chemical class 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000000654 additive Substances 0.000 claims abstract description 12
- 230000000996 additive effect Effects 0.000 claims abstract description 12
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 11
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical group I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 11
- 150000007530 organic bases Chemical class 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims abstract description 5
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims abstract description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 4
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims abstract description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 4
- 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 claims abstract description 4
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims abstract description 4
- 229940045803 cuprous chloride Drugs 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 20
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000001308 synthesis method Methods 0.000 description 10
- CTOQBSUYGFNMJX-UHFFFAOYSA-N 1-phenyl-3,4-dihydroisoquinoline Chemical compound N=1CCC2=CC=CC=C2C=1C1=CC=CC=C1 CTOQBSUYGFNMJX-UHFFFAOYSA-N 0.000 description 9
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- HUPGYVOHHRUZON-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NCCC2=CC(=C(C=C12)C)C Chemical compound C1(=CC=CC=C1)C1=NCCC2=CC(=C(C=C12)C)C HUPGYVOHHRUZON-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- PRTRSEDVLBBFJZ-UHFFFAOYSA-N 1-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=CC=CC=C1 PRTRSEDVLBBFJZ-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- VBEDTUIEGFRVLE-UHFFFAOYSA-N 1-(2-methylphenyl)-3,4-dihydroisoquinoline Chemical compound CC1=CC=CC=C1C1=NCCC2=CC=CC=C12 VBEDTUIEGFRVLE-UHFFFAOYSA-N 0.000 description 2
- DLBWKAFXVLPWSQ-UHFFFAOYSA-N 1-(3-methylphenyl)-3,4-dihydroisoquinoline Chemical compound CC=1C=C(C=CC=1)C1=NCCC2=CC=CC=C12 DLBWKAFXVLPWSQ-UHFFFAOYSA-N 0.000 description 2
- ABOCLVHNYWRZEE-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-dihydroisoquinoline Chemical compound C1=CC(F)=CC=C1C1=NCCC2=CC=CC=C12 ABOCLVHNYWRZEE-UHFFFAOYSA-N 0.000 description 2
- RXFMNKGACYRRQG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3,4-dihydroisoquinoline Chemical compound C1=CC(OC)=CC=C1C1=NCCC2=CC=CC=C12 RXFMNKGACYRRQG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
- NLRPAYVOSIARFS-UHFFFAOYSA-N 1-(3-methylphenyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound CC1=CC=CC(C2C3=CC=CC=C3CCN2)=C1 NLRPAYVOSIARFS-UHFFFAOYSA-N 0.000 description 1
- FSFZUYODRIULLG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC(OC)=CC=C1C1C2=CC=CC=C2CCN1 FSFZUYODRIULLG-UHFFFAOYSA-N 0.000 description 1
- FBOUYBDGKBSUES-KEKNWZKVSA-N 1-azabicyclo[2.2.2]octan-3-yl (1s)-1-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(OC2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-KEKNWZKVSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- HPUBXFZKUDTWRH-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2[C]=NCCC2=C1 HPUBXFZKUDTWRH-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 101000767991 Aspergillus niger Monoamine oxidase N Proteins 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 0.000 description 1
- 241001562081 Ikeda Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 208000020629 overactive bladder Diseases 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 description 1
- 229960003855 solifenacin Drugs 0.000 description 1
- 229960001368 solifenacin succinate Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Description
Claims (9)
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CN202210032924.4A CN114195713B (zh) | 2022-01-12 | 2022-01-12 | 一种催化四氢异喹啉选择性脱氢合成二氢异喹啉的方法 |
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CN202210032924.4A CN114195713B (zh) | 2022-01-12 | 2022-01-12 | 一种催化四氢异喹啉选择性脱氢合成二氢异喹啉的方法 |
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CN114195713A true CN114195713A (zh) | 2022-03-18 |
CN114195713B CN114195713B (zh) | 2023-11-17 |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090247757A1 (en) * | 2007-11-07 | 2009-10-01 | Chao-Jun Li | Ligands, their preparation and uses thereof in asymmetric reactions |
CN105566218A (zh) * | 2014-10-11 | 2016-05-11 | 中国科学院大连化学物理研究所 | 一种钯碳催化的四氢异喹啉选择性部分脱氢的方法 |
CN106699657A (zh) * | 2015-11-13 | 2017-05-24 | 中国科学院大连化学物理研究所 | 溶剂促进的四氢异喹啉类化合物选择性脱氢的方法 |
CN109134368A (zh) * | 2018-09-14 | 2019-01-04 | 福州大学 | 一种由1,2,3,4-四氢异喹啉半脱氢氧化合成3,4-二氢异喹啉的方法 |
CN111484459A (zh) * | 2019-01-28 | 2020-08-04 | 中国科学院大连化学物理研究所 | 一种钯催化不对称氢化合成手性3-三氟甲基-3,4-二氢喹喔啉酮的方法 |
CN111621805A (zh) * | 2019-02-27 | 2020-09-04 | 天津大学 | 一种电催化选择性脱氢制备3,4—二氢异喹啉的方法 |
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2022
- 2022-01-12 CN CN202210032924.4A patent/CN114195713B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090247757A1 (en) * | 2007-11-07 | 2009-10-01 | Chao-Jun Li | Ligands, their preparation and uses thereof in asymmetric reactions |
CN105566218A (zh) * | 2014-10-11 | 2016-05-11 | 中国科学院大连化学物理研究所 | 一种钯碳催化的四氢异喹啉选择性部分脱氢的方法 |
CN106699657A (zh) * | 2015-11-13 | 2017-05-24 | 中国科学院大连化学物理研究所 | 溶剂促进的四氢异喹啉类化合物选择性脱氢的方法 |
CN109134368A (zh) * | 2018-09-14 | 2019-01-04 | 福州大学 | 一种由1,2,3,4-四氢异喹啉半脱氢氧化合成3,4-二氢异喹啉的方法 |
CN111484459A (zh) * | 2019-01-28 | 2020-08-04 | 中国科学院大连化学物理研究所 | 一种钯催化不对称氢化合成手性3-三氟甲基-3,4-二氢喹喔啉酮的方法 |
CN111621805A (zh) * | 2019-02-27 | 2020-09-04 | 天津大学 | 一种电催化选择性脱氢制备3,4—二氢异喹啉的方法 |
Non-Patent Citations (4)
Title |
---|
BO ZHENG ET AL.: ""Copper-Catalyzed Benign and Efficient Oxidation of Tetrahydroisoquinolines and Dihydroisoquinolines Using Air as a Clean Oxidant"", 《ACS OMEGA》, vol. 3, pages 8243 - 8252 * |
RAJENDRA D. PATIL ET AL.: ""Copper-Catalyzed Aerobic Oxidation of Amines to Imines under Neat Conditions with Low Catalyst Loading"", 《ADV. SYNTH. CATAL.》, vol. 353, pages 1695 - 1700 * |
ZHONGHUA QU ET AL.: ""Regioselectivity Control in the Oxidative Formal [3 + 2] Annulations of Ketoxime Acetates and Tetrohydroisoquinolines"", 《ORGANIC LETTERS》, vol. 21, pages 8239 - 8243 * |
姬悦 等: ""Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C"", 《催化学报》, vol. 36, pages 33 - 39 * |
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CN114195713B (zh) | 2023-11-17 |
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