CN115108967A - N-hydroxy-3, 4,5, 6-tetra (carbazol-9-yl) phthalimide, and preparation method and application thereof - Google Patents
N-hydroxy-3, 4,5, 6-tetra (carbazol-9-yl) phthalimide, and preparation method and application thereof Download PDFInfo
- Publication number
- CN115108967A CN115108967A CN202210729014.1A CN202210729014A CN115108967A CN 115108967 A CN115108967 A CN 115108967A CN 202210729014 A CN202210729014 A CN 202210729014A CN 115108967 A CN115108967 A CN 115108967A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- phthalimide
- hydroxy
- reaction
- 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.)
- Granted
Links
- KAYRFHAOQKJIIX-UHFFFAOYSA-N ON(C(C(C1=C(C(N2C3=CC=CC=C3C3=C2C=CC=C3)=C2N3C4=CC=CC=C4C4=C3C=CC=C4)N3C4=CC=CC=C4C4=C3C=CC=C4)=C2N2C3=CC=CC=C3C3=C2C=CC=C3)=O)C1=O Chemical compound ON(C(C(C1=C(C(N2C3=CC=CC=C3C3=C2C=CC=C3)=C2N3C4=CC=CC=C4C4=C3C=CC=C4)N3C4=CC=CC=C4C4=C3C=CC=C4)=C2N2C3=CC=CC=C3C3=C2C=CC=C3)=O)C1=O KAYRFHAOQKJIIX-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 10
- 150000001336 alkenes Chemical class 0.000 claims abstract description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 7
- 239000011941 photocatalyst Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 53
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 11
- 238000006555 catalytic reaction Methods 0.000 claims description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract 1
- 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 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- -1 N-tert-butoxycarbonyl-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide Chemical compound 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000001699 photocatalysis Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OFLRJMBSWDXSPG-UHFFFAOYSA-N 3,4,5,6-tetrafluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(C#N)=C1F OFLRJMBSWDXSPG-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- QMXFUIUEGUOSEV-UHFFFAOYSA-N 3,4,5,6-tetra(carbazol-9-yl)benzene-1,2-dicarbonitrile Chemical compound N#Cc1c(C#N)c(c(c(c1-n1c2ccccc2c2ccccc12)-n1c2ccccc2c2ccccc12)-n1c2ccccc2c2ccccc12)-n1c2ccccc2c2ccccc12 QMXFUIUEGUOSEV-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001789 chalcones Chemical class 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003041 laboratory chemical Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- B01J35/39—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
Abstract
The invention discloses N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide and a preparation method and application thereof, wherein the N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide has a chemical structure shown in a formula 1:
Description
Technical Field
The invention relates to N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide, a preparation method and application thereof, belonging to the technical field of organic synthesis.
Background
The organic compound N-hydroxyphthalimide (NHPI), an inexpensive, non-toxic catalyst prepared from phthalic anhydride and hydroxylamine (Karakurt, a.; Dalkara, s.; Ozalp, m.; Ozbey, s.; Kendi, e.; Stables, j.p. eur.j.med.chem.2001,36,421). NHPI can generate phthalimide-N-oxyl (PINO) under the action of radical initiators or under oxidative conditions, which can grab hydrogen atoms in organic molecules to regenerate NHPI. Thus, through the NHPI/PINO cycle, inert carbon-hydrogen bonds in organic molecules can be efficiently activated to achieve a series of chemical transformations (Ishii, Y.; Sakaguchi, S.; Iwahama, T.Adv.Synth.Catal.2001,343,393 and Sheldon, R.A.; Arends, I.W.C.E.Adv.Synth.Catal.2004,346, 1051).
The group of Grochowski topics discovered and reported for the first time in 1977 that NHPI participates in free radical reactions. They found that ether compounds and diethyl azodicarboxylate can undergo addition reaction under the action of NHPI; 2-propanol was successfully oxidized to acetone by m-CPBA under the catalysis of NHPI (Grochowski, E.; Boleslawska, T.; Jurczak, J. Synthesis1977, 718). Since then, the Ishii topic group reported that alkanes and alcohols could be efficiently oxidized by oxygen to the corresponding ketones or carboxylic acids under catalysis of NHPI (Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y.J.org.Chem.1995,60,3934). By utilizing the strategy, Daicela et al successfully develops a new process for synthesizing terephthalic acid from p-xylene, and the new process does not generate nitrogen oxides, is environment-friendly and has no corrosion to equipment (John, D.Focus on Catalysts,2004, Issue 1, January 2004, p 7). NHPI is also effective in catalyzing the electrochemical oxidation of silanes to produce the corresponding silanol (Liang, h.; Wang, l.j.; Ji, y.x.; Wang, h.; Zhang, b.angelw.chem.int.ed.2020, 59, 2.).
NHPI can also co-catalyze important organic reactions with transition metals. For example, the Ishii topic group in 2003 reported that the reaction of silane and electron deficient olefin with oxygen as oxidant under the concerted catalysis of NHPI and cobalt acetate can introduce silicon and hydroxyl groups into the olefin molecule simultaneously, thereby successfully achieving silicon hydroxylation of olefins (Tayama, O.; Iwahama, T.; Sakaguchi, S.; Ishii, Y.Eur.J.Org.Chem.2003, 2286); under similar conditions, arylmethanes can be efficiently oxidized into aromatic aldehydes under mild conditions, and further oxidation of aldehydes into acids can be avoided (Gaster, E.; Kozuch, S.; Pappo, D.Angew.chem.int.Ed.2017,56,5912). In addition, NHPI may also be used in combination with palladium catalysts to catalyze the conversion of arylmethanes to arylnitriles (Shu, Z.B.; Ye, Y.X.; Deng, Y.F.; Zhang, Y.; Wang, J.B.Angew.chem.int.Ed.2013,52,10573).
NHPI may also catalyze some photochemical reactions. For example, NHPI catalyzes the reaction of benzaldehyde with β -nitrostyrene under white light irradiation to synthesize chalcones (Tripathhi, S.; Kapor, R.; Yadav, L.D. S.Adv. Synth. Catal.2018,360, 1407). Under light induction and co-catalysis of alpha-Fe 2O3 and NHPI, ethylbenzene can be oxidized by oxygen, the main product is acetophenone, and the method has low cost and great industrial application potential (Zhang, C.F.; Huang, Z.P.; Lu, J.M.; Luo, N.C.; Wang, F.J.Am.chem.Soc.2018,140, 2032).
However, the generation of reactive PINO radicals from NHPI often requires relatively severe conditions, such as in the case of oxygen as an oxidant, often requiring UV irradiation to produce PINO. And due to the strong electron deficiency property, NHPI is easy to open ring and decompose in the reaction, so that better reaction effect can be realized by adding more NHPI frequently, side reactions are increased due to decomposition of NHPI, and the treatment after the reaction is complicated. These disadvantages limit the industrial application of NHPI.
With the increasing energy cost and the concern of human beings on the environment, the trend of the chemical industry towards green chemistry cannot be reversed. Compared with ultraviolet light, the chemical conversion conditions induced by visible light are milder and greener, and the method becomes one of important development directions for energy conservation and emission reduction. However, NHPI has no absorption in the visible light band and is difficult to be excited to produce active PINO.
In view of this, it is necessary to structurally modify and modify NHPI so that it can be directly excited to generate PINO-type radicals under the induction of visible light, thereby catalyzing the chemical conversion under milder conditions and promoting the catalytic properties of NHPI/PINO to have higher application value.
Disclosure of Invention
In view of the above problems in the prior art, the present invention is to provide an N-hydroxy-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide, a preparation method and applications thereof.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides N-hydroxy-3, 4,5, 6-tetra (carbazol-9-yl) phthalimide (abbreviated as 4CzNHPI) with a chemical structure shown as a formula 1:
a preparation method of N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide comprises the following steps e or d to e or c to d to e or b to c to d to e or a step a to b to c to d to e in a synthetic route:
wherein the structural formula of Cz-H is as follows:
in one embodiment, step a is carried out by nucleophilic substitution of a compound of formula 2 (i.e., 3,4,5, 6-tetrafluorophthalonitrile) with carbazole to obtain a compound of formula 3.
In a preferred embodiment, the operation of step a is as follows: the compound of formula 2 is subjected to nucleophilic substitution reaction with carbazole in an organic solvent (preferably tetrahydrofuran) under the promotion of NaH at room temperature to obtain the compound of formula 3.
In a preferred embodiment, step a, the compound of formula 2: the molar ratio of carbazole is 1: (4-5), a compound of formula 2: the molar ratio of NaH is 1: (5-8).
In one embodiment, the step b is to perform hydrolysis and ring closure reaction on the compound of formula 3 under the alkaline (preferably KOH) condition to obtain the compound of formula 4.
In a preferred embodiment, step b is performed as follows: the compound of formula 3 is hydrolyzed and subjected to ring closure reaction in an alcohol solvent (preferably ethanol) under the action of KOH under the condition of heating reflux to obtain the compound of formula 4.
In a preferred embodiment, step b, the compound of formula 3: the molar ratio of KOH is 1: (50-100).
In one embodiment, said step c is a step of obtaining the compound of formula 5 from the compound of formula 4 under catalysis of an acid (preferably p-toluenesulfonic acid).
In a preferred embodiment, step c is performed as follows: the compound of formula 4 is reacted in an alcohol solvent (preferably ethanol) at room temperature under the action of p-toluenesulfonic acid to obtain the compound of formula 5.
In a preferred embodiment, in step c, the molar ratio of the compound of formula 4 to p-toluenesulfonic acid is 1: (3-5).
In one embodiment, step d is performed by reacting a compound of formula 5 with Boc 2 O (i.e., di-tert-butyl dicarbonate) to obtain the compound of formula 6 (i.e., N-tert-butoxycarbonyl-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide).
In a preferred embodiment, step d is performed as follows: the compound of formula 5 is reacted with Boc in an organic solvent, preferably acetonitrile, catalyzed by 4-dimethylaminopyridine (i.e., DMAP) 2 And O is reacted to obtain the compound of formula 6.
In a preferred embodiment, step d, the compound of formula 5: boc 2 The molar ratio of O is 1: (1-2).
In one embodiment, step e is carried out by reacting the compound of formula 6 with an aqueous solution of hydroxylamine to provide the compound of formula 1.
In a preferred embodiment, step e, the compound of formula 6: the molar ratio of the hydroxylamine aqueous solution is 1: (10-20).
An application of N-hydroxy-3, 4,5, 6-tetra (carbazol-9-yl) phthalimide as photocatalyst in the oxidation reaction of olefin.
A preferred embodiment, which is used as a photocatalyst for the oxidation of an olefin (preferably an aryl olefin) to a ketone, specifically:
compared with the prior art, the invention has the following remarkable beneficial effects:
the N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide (abbreviated as 4CzNHPI) is based on a skeleton of a polycarbazole aromatic ring, has four carbazoles, a large aromatic conjugated system and obvious absorption in a visible light region of 400-500 nm, easily loses one electron under the excitation of visible light, forms a free radical similar to PINO, and can be used as a photocatalyst for the oxidation reaction of olefin; in addition, the method takes 3,4,5, 6-tetrafluorophthalic nitrile (a compound shown in a formula 2) as an initial raw material, and prepares the N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide through five-step reaction.
Drawings
FIG. 1 shows UV-visible absorption spectra of N-hydroxy-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide in various solvents (dichloromethane, 1, 4-dioxane, acetonitrile) according to the present invention.
Detailed Description
The technical scheme of the invention is further detailed and completely explained by combining the specific embodiment.
In this example, the solvents and reagents used were, unless otherwise specified, purified by the methods described in Armarego, W.L.F.; perrin, d.d. purification of Laboratory Chemicals,4th ed.; butterworth Heinemann: Oxford,1997. melting point uncorrected; 1 H NMR, 13 c NMR measurements on NMR instruments Agilent 400M and Bruker-500M; HR-MS (EI) on Waters GCT CA 176, HR-MS (ESI) on BRUKER DALTONICS APEX III; IR spectra were measured on the instrument Bio-Rad FTS-185; melting point was measured on a micro melting point apparatus SWG X-4; tobacco chemical plant for rapid column chromatographyThe produced silica gel (200-300 meshes); the color development modes are ultraviolet color development, potassium permanganate solution color development and iodine cylinder color development.
Example 1: preparation of compound of formula 3 (3,4,5, 6-tetrakis (carbazol-9-yl) -1, 2-benzenedinitrile)
Weighing NaH (1.8g,75mmol) into a reaction flask equipped with a stirrer, adding 10mL of anhydrous tetrahydrofuran under argon protection using schlenk technique, adding a solution of carbazole (7.0g,45mmol) in tetrahydrofuran (50mL) after stirring for 5 minutes, stirring at room temperature for 30 minutes, then adding a solution of 3,4,5, 6-tetrafluoro-1, 2-benzenedinitrile (2.0g,10mmol) in tetrahydrofuran (10mL), stirring at room temperature for 24 hours (monitoring the reaction by TLC during the reaction), terminating the reaction, quenching excess NaH with water, followed by extraction with dichloromethane (3X 100mL), saturated NH 4 Washing with an aqueous solution of Cl, combining the organic phases, drying with anhydrous sodium sulfate, collecting the dried organic phase, removing the organic solvent under reduced pressure, and separating by column chromatography to obtain 7.6g of the compound of formula 3 (yield: 96%). The spectral data of the obtained compounds are consistent with the literature reports (UOyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C.Nature 2012,492,234).
Example 2: preparation of compound of formula 4 (4,5,6, 7-tetrakis (carbazol-9-yl) -3-amino-1H-isoindol-1-one)
The compound of formula 3 (2.4g,3mmol) and potassium hydroxide (11.8g,210mmol) were weighed, and ethanol was used as a solvent (120mL), refluxed for 2 hours, then cooled to room temperature, ethanol was removed under reduced pressure, dichloromethane (3X 60mL) was used for extraction, the organic phases were washed with a saturated aqueous solution of sodium chloride, the organic phases were combined, dried over anhydrous sodium sulfate, the dried organic phase was collected, the organic solvent was removed under reduced pressure, and separation was performed by column chromatography to obtain 2.3g of the compound of formula 4 (yellow solid, yield: 95%).
Through the test: melting point: 300 ℃ is adopted;
1 H NMR(400MHz,DMSO-d 6 )δ7.73-7.93(m,4H),7.53-7.70(m,4H),7.40-7.53(m,4H),7.25-7.38(m,4H),6.90-7.20(m,10H),6.68(t,J＝8.0Hz,4H),6.60(t,J＝8.0Hz,4H)；
ESI-MS:m/z 807.3(M + +H)；
HRMS calcd for C 56 H 35 N 6 O[M+H]807.2867,found:807.2853；
IR(KBr):ν(cm -1 )3047,2922,1741,1659,1626,1598,1491,1479,1451,1335,1309,1224,1150,1045,741,723。
example 3: preparation of Compound of formula 5 (3,4,5, 6-tetrakis (carbazol-9-yl) phthalimide)
The compound of formula 4 (1.6g,2mmol) and p-toluenesulfonic acid hydrate (1.5g,8mmol) were weighed, refluxed with ethanol (60mL) as a solvent for 12 hours, then cooled to room temperature, ethanol was removed under reduced pressure, extracted with dichloromethane (3X 50mL), the organic phases were washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, the organic phases were combined, dried over anhydrous sodium sulfate, the dried organic phase was collected, the organic solvent was removed under reduced pressure, and separated by column chromatography to give 0.76g of the compound of formula 5 (yellow solid, yield: 48%).
After testing: melting point: 300 ℃ is adopted;
1 H NMR(400MHz,DMSO-d 6 )δ7.75-7.90(m,4H),7.50-7.65(m,4H),7.40(d,J＝8.0Hz,4H),7.34(d,J＝8.0Hz,4H),6.95-7.10(m,8H),6.69(t,J＝8.0Hz,4H),6.58(t,J＝8.0Hz,4H),5.85(s,1H)；
13 C NMR(101MHz,acetone-d 6 )δ165.4,142.7,140.9,139.1,134.9,132.6,125.6,124.8,124.4,124.2,120.9,120.8,120.4,119.8,112.1,111.8；
ESI-MS:m/z 808.3(M + +H)；
HRMS calcd for C 56 H 34 N 5 O 2 [M+H]808.2707,found:808.2698；
IR(KBr):ν(cm -1 )3343,3047,2961,1770,1725,1625,1597,1491,1479,1458,1390,1334,1308,1260,1224,1091,1040,800,738,721。
example 4: preparation of the Compound of formula 6 (N-tert-Butoxycarbonyl-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide)
The compound of formula 5 (808mg,1mmol) and 4-dimethylaminopyridine (DMAP,6mg,0.05mmol) were weighed, 40mL of acetonitrile was added as a solvent, and stirred for 10 minutes, followed by addition of di-tert-butyl dicarbonate (327mg,1.5mmol) at 0 ℃ and stirring at room temperature for 10 hours (monitoring the reaction by TLC during the reaction), the reaction was terminated, acetonitrile was removed under reduced pressure, extraction was performed with dichloromethane (3X 50mL), the organic phases were combined, dried over anhydrous sodium sulfate, the dried organic phase was collected, the organic solvent was removed under reduced pressure, and column chromatography was performed to obtain 835mg of the compound of formula 6 (yellow solid, yield: 92%).
Through the test: melting point: a temperature of >300 ℃;
1 H NMR(400MHz,CDCl 3 )δ7.73(d,J＝7.6Hz,4H),7.28(d,J＝7.6Hz,4H),6.88-7.10(m,16H),6.74(t,J＝7.6Hz,4H),6.54(t,J＝7.6Hz,4H),1.48(s,9H)；
13 C NMR(126MHz,acetone-d 6 )δ161.0,146.7,143.7,140.8,139.2,135.9,131.2,126.3,125.0,124.6,124.4,121.2,121.1,120.6,120.0,112.1,111.9,85.9,27.8；
ESI-MS:m/z 930.3(M + +Na)；
HRMS calcd for C 61 H 41 N 5 NaO 4 [M+Na]930.3051,found:930.3036；
IR(KBr):ν(cm -1 )2919,2849,1802,1774,1731,1626,1599,1491,1479,1446,1333,1309,1244,1224,1146,840,742,722。
example 5: preparation of the Compound of formula 1 (N-hydroxy-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide)
The compound of formula 6 (908mg,1mmol) was weighed, acetonitrile was used as a solvent, then an aqueous hydroxylamine solution (50 wt% aqueous solution, 1.3g,20mmol) was added, stirred at room temperature for 12 hours (reaction was monitored by TLC during the reaction), the reaction was terminated, cooled to room temperature, acetonitrile was removed under reduced pressure, extracted with dichloromethane (3 × 50mL), washed successively with 1N aqueous hydrochloric acid solution and saturated aqueous sodium chloride solution, the organic phases were combined, dried over anhydrous sodium sulfate, the dried organic phase was collected, the organic solvent was removed under reduced pressure, and separated by column chromatography to obtain 733mg of the compound of formula 1 (yellow solid, yield: 89%).
Through the test: melting point: 300 ℃ is adopted;
1 H NMR(400MHz,CDCl 3 )δ7.72(d,J＝7.6Hz,4H),7.30(d,J＝7.6Hz,4H),6.88-7.10(m,16H),6.75(t,J＝8.0Hz,4H),6.56(t,J＝8.0Hz,4H)；
13 C NMR(101MHz,acetone-d 6 )δ161.2,142.8,141.0,139.3,134.9,129.4,125.7,124.9,124.5,124.3,121.0,120.9,120.5,119.9,112.1,111.8；
ESI-MS:m/z 824.3(M + +H)；
HRMS calcd for C 56 H 34 N 5 O 3 [M+H]824.2656,found:824.2642；
IR(KBr):ν(cm -1 )3047,2923,1787,1731,1625,1599,1490,1479,1454,1334,1309,1224,1149,926,742,722。
application example: photocatalytic performance of compound (N-hydroxy-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide, abbreviated as: 4CzNHPI) of formula 1 was examined by reaction for preparation of acetophenone by oxidation of 2-phenyl-1-propene
Firstly, ultraviolet visible absorption spectra of 4CzNHPI in different solvents (dichloromethane, 1, 4-dioxane, acetonitrile) are detected, and the detection result is shown in fig. 1, as can be seen from fig. 1, 4CzNHPI in the three solvents has significant absorption in a visible light region of 400-500 nm, which indicates that 4CzNHPI has photocatalytic performance and can be used for visible light-induced catalytic reaction.
Next, taking 2-phenyl-1-propene as an example, the catalytic properties of 4CzNHPI on oxidation reaction induced by visible light are examined, specifically:
add 4CzNHPI (0.004mmol) to a 10mL stopcock with internal stirrer, evacuate the system and replace oxygen three times, then add 2-phenyl-1-propene (0.2mmol) with CH 3 CN (1mL) as solvent, screwing a stopcock, placing the stopcock under 20W blue light irradiation at 80 deg.C, stirring for 16 hr to terminate the reaction, concentrating the reaction solution under reduced pressure, filtering, extracting with ethyl acetate (5 mL. times.3), combining the organic phases, and adding anhydrous Na 2 SO 4 Drying, concentrating under reduced pressure, adding CH into the reaction solution 2 Br 2 (0.1mmol) as an internal standard by 1 The nuclear magnetic yield of the oxidation product acetophenone was determined by H NMR to be 51%.
The reaction results show that: in the reaction process of preparing acetophenone by oxidizing 2-phenyl-1-propylene under the catalysis of 4CzNHPI, oxygen is used as an oxidant, the reaction can be carried out under normal pressure without any metal, and the conditions are mild, so that the 4CzNHPI has excellent photocatalytic performance and can be used as a photocatalyst for the oxidation reaction of olefin.
Finally, it should be pointed out here that: the above is only a part of the preferred embodiments of the present invention and should not be construed as limiting the scope of the present invention, and the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above description are intended to be covered by the present invention.
Claims (10)
1. An N-hydroxy-3, 4,5, 6-tetrakis (carbazol-9-yl) phthalimide having the chemical structure shown in formula 1:
2. a method for preparing N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide is characterized by comprising the following steps e or d to e or c to d to e or b to c to d to e or a step a to b to c to d to e in a synthetic route:
wherein the structural formula of Cz-H is as follows:
3. the production method according to claim 2, characterized in that: the step a is to perform nucleophilic substitution reaction on the compound of the formula 2 and carbazole to obtain the compound of the formula 3.
4. The production method according to claim 3, characterized in that: in step a, a compound of formula 2: the molar ratio of carbazole is 1: (4-5).
5. The method of claim 2, wherein: and the step b is to perform hydrolysis and ring closure reaction on the compound of the formula 3 under alkaline conditions to obtain the compound of the formula 4.
6. The method of claim 2, wherein: the step c is to obtain the compound of the formula 5 from the compound of the formula 4 under the catalysis of acid.
7. The method of claim 2, wherein: the step d is carried out by reacting the compound shown in the formula 5 with Boc 2 And O reaction to obtain the compound shown in the formula 6.
8. The method of claim 2, wherein: the step e is to react the compound shown in the formula 6 with an aqueous hydroxylamine solution to obtain the compound shown in the formula 1.
9. The method of claim 8, wherein: in step e, a compound of formula 6: the molar ratio of the hydroxylamine aqueous solution is 1: (10-20).
10. The application of N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide is characterized in that: used as photocatalyst for the oxidation reaction of olefin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210729014.1A CN115108967B (en) | 2022-06-24 | 2022-06-24 | N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210729014.1A CN115108967B (en) | 2022-06-24 | 2022-06-24 | N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115108967A true CN115108967A (en) | 2022-09-27 |
| CN115108967B CN115108967B (en) | 2023-09-19 |
Family
ID=83328658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210729014.1A Active CN115108967B (en) | 2022-06-24 | 2022-06-24 | N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115108967B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116143681A (en) * | 2023-02-28 | 2023-05-23 | 昆明理工大学 | N-aryl phthalimide derivative and application thereof in organic photochemistry |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT103718A (en) * | 2007-04-13 | 2007-06-29 | Inst Superior Tecnico | SYNTHESIS METHOD OF 3-IMINOISOINDOLIN-1-ONAS BASED ON THE USE OF N, N-DIETYL-HYDROXYLAMINE |
| CN109734649A (en) * | 2019-02-19 | 2019-05-10 | 中国科学院化学研究所 | One kind is based on the imido small organic molecule efficient room temperature phosphor material of virtue and its preparation and application |
| CN111635299A (en) * | 2020-06-09 | 2020-09-08 | 大连理工大学 | Method for preparing aromatic alpha ketone carbonyl compound by continuous visible light catalytic molecular oxygen oxidation in microchannel reactor |
| CN112062707A (en) * | 2020-07-30 | 2020-12-11 | 阜阳师范大学 | Carbon-hydrogen bond activation method for nonmetal-participated inert alkane |
| CN112159314A (en) * | 2020-09-08 | 2021-01-01 | 宁波大学 | Method for generating benzaldehyde by oxidizing alpha-monosubstituted styrene under catalysis of N-hydroxyphthalimide |
-
2022
- 2022-06-24 CN CN202210729014.1A patent/CN115108967B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT103718A (en) * | 2007-04-13 | 2007-06-29 | Inst Superior Tecnico | SYNTHESIS METHOD OF 3-IMINOISOINDOLIN-1-ONAS BASED ON THE USE OF N, N-DIETYL-HYDROXYLAMINE |
| CN109734649A (en) * | 2019-02-19 | 2019-05-10 | 中国科学院化学研究所 | One kind is based on the imido small organic molecule efficient room temperature phosphor material of virtue and its preparation and application |
| CN111635299A (en) * | 2020-06-09 | 2020-09-08 | 大连理工大学 | Method for preparing aromatic alpha ketone carbonyl compound by continuous visible light catalytic molecular oxygen oxidation in microchannel reactor |
| CN112062707A (en) * | 2020-07-30 | 2020-12-11 | 阜阳师范大学 | Carbon-hydrogen bond activation method for nonmetal-participated inert alkane |
| CN112159314A (en) * | 2020-09-08 | 2021-01-01 | 宁波大学 | Method for generating benzaldehyde by oxidizing alpha-monosubstituted styrene under catalysis of N-hydroxyphthalimide |
Non-Patent Citations (3)
| Title |
|---|
| GONDA, ZSOMBOR等: "Modular Synthesis of Carbazole-Substituted Phthalimides as Potential Photocatalysts", 《SYNTHESIS》, vol. 54, no. 17, pages 3771 - 3784 * |
| MASAYA SHIBANO等: "Thermally Activated Delayed Fluorescence Benzyl Cellulose Derivatives for Nondoped Organic Light-Emitting Diodes", 《MACROMOLECULES》, vol. 53, pages 2864 - 2873 * |
| TERUMASA KATO等: "Design of Bowl-Shaped N-Hydroxyimide Derivatives as New Organoradical Catalysts for Site-Selective C(sp3)-H Bond Functionalization Reactions", 《ANGEWANDTE CHEMIE INTERNATIONAL EDITION 》, vol. 59, no. 34, pages 14261 - 14264 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116143681A (en) * | 2023-02-28 | 2023-05-23 | 昆明理工大学 | N-aryl phthalimide derivative and application thereof in organic photochemistry |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115108967B (en) | 2023-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Sarma et al. | Visible-light induced enhancement in the multi-catalytic activity of sulfated carbon dots for aerobic carbon–carbon bond formation | |
| Saedi et al. | MIL-101 metal–organic framework: A highly efficient heterogeneous catalyst for oxidative cleavage of alkenes with H2O2 | |
| Gogoi et al. | Rice husk derived nanosilica supported Cu (II) complex: an efficient heterogeneous catalyst for oxidation of alcohols using TBHP | |
| Rajabi et al. | Heterogeneously catalysed Strecker-type reactions using supported Co (II) catalysts: Microwave vs. conventional heating | |
| Fildes et al. | Potassium exchanged zirconium hydrogen phosphate Zr (O3POK) 2: a heterogeneous basic catalyst for Knoevenagel reaction without solvent | |
| Khaligh et al. | Preparation, characterization and use of poly (4-vinylpyridinium) hydrogen sulfate salt as an eco-benign, efficient and reusable solid acid catalyst for the chemoselective 1, 1-diacetate protection and deprotection of aldehydes | |
| CN115108967B (en) | N-hydroxy-3, 4,5, 6-tetra (carbazole-9-yl) phthalimide and preparation method and application thereof | |
| Firouzabadi et al. | Transformation of allylic and benzylic oximes to their carbonyl compounds with zinc bismuthate Zn (BiO3) 2 | |
| Davoodnia et al. | A Modified and Green Procedure for the Synthesis of β‐Amido Ketones Using a Br? nsted‐Acidic Ionic Liquid as Novel and Reusable Catalyst | |
| CN111269087B (en) | Method for catalyzing cumene oxidation by trace copper-promoted carbon nano tube | |
| Li et al. | Oxodiperoxo tungsten complex-catalyzed synthesis of adipic acid with hydrogen peroxide | |
| CN109499609B (en) | SBA-15 immobilized 2-azaadamantane nitroxide free radical catalyst and preparation and application thereof | |
| JP3568858B2 (en) | Production of cyclic alcohols and ketones | |
| Khusnutdinov et al. | Synthesis of 1-benzofuran-2-carboxylates by reaction of 1-benzofuran with halomethanes and alcohols in the presence of iron compounds | |
| FI108432B (en) | Regeneration of the working solution in the hydrogen peroxide production process | |
| JP4242288B2 (en) | Manganese (IV) complex salts and their use as oxidation catalysts | |
| JP2588374B2 (en) | Method for producing hydridecarbonyltris (triorganophosphorus) rhodium compound | |
| RU2430087C1 (en) | Method of producing cyclic geminal bis-hydroperoxides | |
| JP2005514446A6 (en) | Manganese (IV) complex salts and their use as oxidation catalysts | |
| JP5077795B2 (en) | Method for producing carbonyl compound | |
| CN105111128A (en) | Method for preparing N-hydroxyphthalimide | |
| CN111138315B (en) | Cyanoalkyl substituted quinone compound and synthesis method thereof | |
| Tamami et al. | Microwave promoted rapid oxidative deoximation of oximes under solvent-free conditions | |
| CN115304465B (en) | Green method for converting 1, 3-dithiane derivative into carbonyl compound | |
| CN115304477B (en) | Preparation method of aromatic carboxylic ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |