CN106905284B - 一种杂蒽酮类化合物的催化氧化合成方法 - Google Patents
一种杂蒽酮类化合物的催化氧化合成方法 Download PDFInfo
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- CN106905284B CN106905284B CN201710103039.XA CN201710103039A CN106905284B CN 106905284 B CN106905284 B CN 106905284B CN 201710103039 A CN201710103039 A CN 201710103039A CN 106905284 B CN106905284 B CN 106905284B
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- reaction
- xanthone
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title abstract description 36
- -1 anthracene ketone compounds Chemical class 0.000 title abstract description 30
- 238000006555 catalytic reaction Methods 0.000 title abstract description 8
- 230000003647 oxidation Effects 0.000 title abstract description 8
- 238000007254 oxidation reaction Methods 0.000 title abstract description 8
- 238000010189 synthetic method Methods 0.000 title abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 60
- 238000006243 chemical reaction Methods 0.000 abstract description 43
- 238000000926 separation method Methods 0.000 abstract description 40
- 229910052760 oxygen Inorganic materials 0.000 abstract description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 37
- 239000001301 oxygen Substances 0.000 abstract description 37
- 239000002904 solvent Substances 0.000 abstract description 31
- 229910002554 Fe(NO3)3·9H2O Inorganic materials 0.000 abstract description 13
- 239000007800 oxidant agent Substances 0.000 abstract description 9
- 230000001590 oxidative effect Effects 0.000 abstract description 9
- 239000003054 catalyst Substances 0.000 abstract description 7
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 6
- 239000000758 substrate Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 26
- 239000003480 eluent Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 15
- 230000006837 decompression Effects 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 238000007789 sealing Methods 0.000 description 14
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 13
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 239000007788 liquid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910021135 KPF6 Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- NEWRXGDGZGIHIS-UHFFFAOYSA-N 2-(trifluoromethyl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(F)(F)F)=CC=C3SC2=C1 NEWRXGDGZGIHIS-UHFFFAOYSA-N 0.000 description 2
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 2
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 2
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- OOAPSVJLHZBWDR-UHFFFAOYSA-N 2-(trifluoromethyl)-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(C(F)(F)F)=CC=C3SC2=C1 OOAPSVJLHZBWDR-UHFFFAOYSA-N 0.000 description 1
- HDMIWIXLPFMCFC-UHFFFAOYSA-N 2-chloro-2h-thiopyrano[3,2-b]chromen-10-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)S2 HDMIWIXLPFMCFC-UHFFFAOYSA-N 0.000 description 1
- OXDWSIQJQNGYQP-UHFFFAOYSA-N C1=CC=CC2=CC3=CC=CC=C3C=C12.C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C12.C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O OXDWSIQJQNGYQP-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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| CN201710103039.XA CN106905284B (zh) | 2017-02-24 | 2017-02-24 | 一种杂蒽酮类化合物的催化氧化合成方法 |
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| CN201710103039.XA CN106905284B (zh) | 2017-02-24 | 2017-02-24 | 一种杂蒽酮类化合物的催化氧化合成方法 |
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| Publication Number | Publication Date |
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| CN106905284A CN106905284A (zh) | 2017-06-30 |
| CN106905284B true CN106905284B (zh) | 2019-06-07 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109082685B (zh) * | 2018-08-28 | 2020-04-21 | 河南师范大学 | 一种在低共熔溶剂中制备花状AuPt合金纳米粒子的方法及其电氧化合成氧杂蒽酮的应用 |
| CN109336813B (zh) * | 2018-09-27 | 2021-08-10 | 浙江工业大学上虞研究院有限公司 | 一种吖啶酮类化合物的光催化氧化合成方法 |
| CN109232525B (zh) * | 2018-09-27 | 2022-12-30 | 浙江工业大学 | 一种硫杂蒽酮类化合物的光催化氧化合成方法 |
| CN111138411B (zh) * | 2019-12-17 | 2021-06-15 | 浙江工业大学 | 一种噻吨酮类化合物的紫外光促进的合成方法 |
| CN111057037B (zh) * | 2019-12-17 | 2021-07-23 | 浙江工业大学 | 一种氧杂蒽酮类化合物的紫外光促进合成方法 |
| CN112851652B (zh) * | 2021-01-18 | 2022-06-14 | 浙江工业大学 | 一种2-(取代氧杂蒽基)苯并呋喃类化合物的催化氧化合成方法 |
-
2017
- 2017-02-24 CN CN201710103039.XA patent/CN106905284B/zh active Active
Non-Patent Citations (3)
| Title |
|---|
| Iron-Catalyzed Benzylic Oxidation with Aqueous tert-Butyl Hydroperoxide;Masafumi Nakanishi，等;《Adv.Synth.Catal.》;20070725;第349卷(第6期);第861-862页 * |
| NHPI and ferric nitrate: a mild and selective system for aerobic oxidation of benzylic methylenes;Chengxia Miao，等;《Catal.Sci.Technol.》;20151008;第6卷(第5期);第1379页左栏图1、第1381页表3 * |
| Oxidation of Alcohols and Activated Alkanes with Lewis Acid-Activated TEMPO;Thuy-Ai D. Nguyen，等;《Inorg.Chem.》;20141016;第53卷(第21期);第11377-11379页 * |
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| Publication number | Publication date |
|---|---|
| CN106905284A (zh) | 2017-06-30 |
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