NL2034563A - Indole compound, its preparation method and application in detection of aldehydes and ketones - Google Patents

Indole compound, its preparation method and application in detection of aldehydes and ketones Download PDF

Info

Publication number: NL2034563A
Authority: NL; Netherlands
Prior art keywords: ketones; aldehydes; indole; detection; compound
Prior art date: 2022-05-27

Application number

NL2034563A

Other languages

English (en)

Dutch (nl)

Inventor

Cao Ying

Wang Sufang

Feng Xueliang

Dong Huaijin

Li Mingxiao

Meng Tian

Original Assignee

Chinese Res Acad Env Sciences

Priority date (The priority date 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 date listed.)

2022-05-27

Filing date

2023-04-13

Publication date

2023-12-05

2023-04-13 Application filed by Chinese Res Acad Env Sciences filed Critical Chinese Res Acad Env Sciences

2023-12-05 Publication of NL2034563A publication Critical patent/NL2034563A/en

Links

150000002576 ketones Chemical class 0.000 title claims abstract description 46
238000001514 detection method Methods 0.000 title claims abstract description 44
150000001299 aldehydes Chemical class 0.000 title claims abstract description 43
-1 Indole compound Chemical class 0.000 title claims abstract description 28
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 21
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims abstract description 21
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 21
238000002360 preparation method Methods 0.000 title claims abstract description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
150000001875 compounds Chemical class 0.000 claims abstract description 22
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
239000005457 ice water Substances 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000003208 petroleum Substances 0.000 claims description 6
229910000104 sodium hydride Inorganic materials 0.000 claims description 6
238000005406 washing Methods 0.000 claims description 6
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 5
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
230000011987 methylation Effects 0.000 claims description 5
238000007069 methylation reaction Methods 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
238000003756 stirring Methods 0.000 claims description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 4
238000001816 cooling Methods 0.000 claims description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
239000012312 sodium hydride Substances 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
238000010791 quenching Methods 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
238000004440 column chromatography Methods 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
OQBNNAMXCZSCFC-UHFFFAOYSA-N methyl 4,6-difluoro-1h-indole-2-carboxylate Chemical compound C1=C(F)C=C2NC(C(=O)OC)=CC2=C1F OQBNNAMXCZSCFC-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
238000000967 suction filtration Methods 0.000 claims description 2
OCHGGXDZJGAUEU-UHFFFAOYSA-N 4,6-difluoro-1h-indole-2-carboxylic acid Chemical compound C1=C(F)C=C2NC(C(=O)O)=CC2=C1F OCHGGXDZJGAUEU-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 15
238000001212 derivatisation Methods 0.000 abstract description 9
239000007788 liquid Substances 0.000 abstract description 8
238000004458 analytical method Methods 0.000 abstract description 7
238000001819 mass spectrum Methods 0.000 abstract description 6
238000005173 quadrupole mass spectroscopy Methods 0.000 abstract description 3
239000002994 raw material Substances 0.000 abstract description 3
238000004885 tandem mass spectrometry Methods 0.000 abstract description 3
239000011159 matrix material Substances 0.000 abstract description 2
238000003541 multi-stage reaction Methods 0.000 abstract description 2
238000011002 quantification Methods 0.000 abstract description 2
238000005481 NMR spectroscopy Methods 0.000 description 24
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
238000001228 spectrum Methods 0.000 description 18
150000002500 ions Chemical class 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
229940125904 compound 1 Drugs 0.000 description 6
238000000034 method Methods 0.000 description 6
229940125782 compound 2 Drugs 0.000 description 5
238000004949 mass spectrometry Methods 0.000 description 5
230000035945 sensitivity Effects 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
230000014759 maintenance of location Effects 0.000 description 4
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
238000011895 specific detection Methods 0.000 description 2
239000012086 standard solution Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
ZJXJFHNOUIZXNU-UHFFFAOYSA-N 1,3-difluoroindole-2-carboxylic acid Chemical compound C1=CC=C2N(F)C(C(=O)O)=C(F)C2=C1 ZJXJFHNOUIZXNU-UHFFFAOYSA-N 0.000 description 1
HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
208000005623 Carcinogenesis Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
230000036952 cancer formation Effects 0.000 description 1
231100000504 carcinogenesis Toxicity 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
238000009795 derivation Methods 0.000 description 1
230000005264 electron capture Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000000105 evaporative light scattering detection Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
210000001533 respiratory mucosa Anatomy 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000001195 ultra high performance liquid chromatography Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1

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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/30—Control of physical parameters of the fluid carrier of temperature
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/32—Control of physical parameters of the fluid carrier of pressure or speed
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/32—Control of physical parameters of the fluid carrier of pressure or speed
- G01N2030/324—Control of physical parameters of the fluid carrier of pressure or speed speed, flow rate
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds

Landscapes

Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Analytical Chemistry (AREA)
Biochemistry (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Immunology (AREA)
Pathology (AREA)
Organic Chemistry (AREA)
Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Indole Compounds (AREA)

NL2034563A 2022-05-27 2023-04-13 Indole compound, its preparation method and application in detection of aldehydes and ketones NL2034563A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CN202210584793.0A CN114671795B (zh)	2022-05-27	2022-05-27	吲哚类化合物、制备方法及其在醛酮检测中的应用

Publications (1)

Publication Number	Publication Date
NL2034563A true NL2034563A (en)	2023-12-05

Family

ID=82080234

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL2034563A NL2034563A (en)	2022-05-27	2023-04-13	Indole compound, its preparation method and application in detection of aldehydes and ketones

Country Status (2)

Country	Link
CN (1)	CN114671795B (zh)
NL (1)	NL2034563A (zh)

2022
- 2022-05-27 CN CN202210584793.0A patent/CN114671795B/zh active Active
2023
- 2023-04-13 NL NL2034563A patent/NL2034563A/en unknown

Also Published As

Publication number	Publication date
CN114671795B (zh)	2022-08-19
CN114671795A (zh)	2022-06-28

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