CN111138445B - 一种镍催化制备5,12-二氧杂蒽-6,11-二酮类化合物的方法 - Google Patents
一种镍催化制备5,12-二氧杂蒽-6,11-二酮类化合物的方法 Download PDFInfo
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- CN111138445B CN111138445B CN202010061633.9A CN202010061633A CN111138445B CN 111138445 B CN111138445 B CN 111138445B CN 202010061633 A CN202010061633 A CN 202010061633A CN 111138445 B CN111138445 B CN 111138445B
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- dioxaanthracene
- nickel
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229910052759 nickel Inorganic materials 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- -1 2-hydroxyphenyl acrylic acid compound Chemical class 0.000 claims abstract description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 239000011630 iodine Substances 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 238000000605 extraction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000003818 flash chromatography Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 1
- 238000005086 pumping Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
- 238000001228 spectrum Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RNFSZYQXRZMUMB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1O RNFSZYQXRZMUMB-UHFFFAOYSA-N 0.000 description 1
- RRKPMLZRLKTDQV-UHFFFAOYSA-N 2-bromo-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1Br RRKPMLZRLKTDQV-UHFFFAOYSA-N 0.000 description 1
- SEJVMKLJNIKFAF-UHFFFAOYSA-N 2-bromo-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(Br)=C1 SEJVMKLJNIKFAF-UHFFFAOYSA-N 0.000 description 1
- ODHJOROUCITYNF-UHFFFAOYSA-N 2-bromo-5-methoxybenzoic acid Chemical compound COC1=CC=C(Br)C(C(O)=O)=C1 ODHJOROUCITYNF-UHFFFAOYSA-N 0.000 description 1
- QBPHOFYPURZIKS-UHFFFAOYSA-N 2-iodo-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(I)=C1 QBPHOFYPURZIKS-UHFFFAOYSA-N 0.000 description 1
- DUKFTVLJAXWGPI-UHFFFAOYSA-N 4-fluoro-2-iodobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1I DUKFTVLJAXWGPI-UHFFFAOYSA-N 0.000 description 1
- VNHKDZZRRQQKTN-UHFFFAOYSA-N 4-tert-butyl-2-iodobenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C(I)=C1 VNHKDZZRRQQKTN-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN202010061633.9A CN111138445B (zh) | 2020-01-19 | 2020-01-19 | 一种镍催化制备5,12-二氧杂蒽-6,11-二酮类化合物的方法 |
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CN111138445B true CN111138445B (zh) | 2022-07-22 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109824588A (zh) * | 2019-03-07 | 2019-05-31 | 浙江农林大学暨阳学院 | 一种钯催化制备2,4-二苯基-8-羟基喹啉类化合物的方法 |
CN110283127A (zh) * | 2019-03-22 | 2019-09-27 | 浙江农林大学暨阳学院 | 一种镍催化制备2-氨基甲酸叔丁酯苯并咪唑类化合物的方法 |
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- 2020-01-19 CN CN202010061633.9A patent/CN111138445B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109824588A (zh) * | 2019-03-07 | 2019-05-31 | 浙江农林大学暨阳学院 | 一种钯催化制备2,4-二苯基-8-羟基喹啉类化合物的方法 |
CN110283127A (zh) * | 2019-03-22 | 2019-09-27 | 浙江农林大学暨阳学院 | 一种镍催化制备2-氨基甲酸叔丁酯苯并咪唑类化合物的方法 |
Non-Patent Citations (2)
Title |
---|
Pd(II)-Catalyzed Oxidative Annulation via Double C−H Activations:Synthesis and Photophysical Properties of Bis-Coumarins;Kumud Sharma et al.;《Organic Letters》;20191209;73-77 * |
Rh(III)Rh(III)Rh(III)-Catalyzed Diverse C-H Functionalization of Iminopyridinium Ylides;Zhenzhen Dong et al.;《Chinese Journal of Chemistry》;20210707;2489-2494 * |
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Effective date of registration: 20230614 Address after: 311800 No. 2, Xingye 3rd Road, Taozhu Street, Zhuji City, Shaoxing, Zhejiang Province Patentee after: Zhuji Fenghui Garment Co.,Ltd. Address before: 311800 Jiyang college, Zhejiang agriculture and Forestry University, 77 Puyang Road, Jiyang street, Zhuji City, Shaoxing City, Zhejiang Province Patentee before: JIYANG COLLEGE OF ZHEJIANG A&F University |
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Denomination of invention: A method for preparing 5,12-dioxanthracene-6,11-diketone compounds catalyzed by nickel Granted publication date: 20220722 Pledgee: Shaoxing Bank Co.,Ltd. Zhuji sub branch Pledgor: Zhuji Fenghui Garment Co.,Ltd. Registration number: Y2024980011829 |