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杂环化合物

杂环化合物是一类分子中具有环状结构的有机化合物,其构成环的原子除了碳外还含有一个或多个氮、硫、氧等其他原子。单杂环化合物仅含一个环,如呋喃、噻唑和吡啶;而稠合杂环化合物则包含两个或更多环,例如喹啉和嘌呤。最稳定且最常见的为五元或六元杂环。

简单杂环化合物能够与苯或其他杂环并合形成双环、三环或多环系统。某些杂环具有芳香族化合物的特性,如易于进行置换反应,难以发生加成反应,并对氧化剂较为稳定。这些化合物广泛存在于自然界中,包括核酸、大多数维生素、叶绿素、血红素、多数生物碱和色素等。此外,部分合成农药也属此类化合物,比如除草剂阿特拉津、杀草强及麦草净,杀虫剂氟克螨与喹硫磷,以及杀菌剂灭菌净和克杀螨等。

构成环系的原子除碳外还含有氧(O)、硫(S)或氮(N)等杂原子的环状化合物被统称为杂环化合物。严格来说,环形二酸酐、环形酰亚胺、内酯、交酯、环状酸酐、内酰胺和环醚等都属于这一范畴;但由于它们性质接近脂肪族化合物,并且容易从开链化合物合成并可逆地转化为链状结构,通常归入脂肪族化学讨论。

因此,杂环化合物一般特指那些环系稳定且具有不同程度芳香性的芳杂环化合物。有机杂环化合物作为开链、碳环和杂环三类有机化合物之一,其种类繁多、数量庞大,占已知有机化合物的约三分之一,并普遍存在于生物界中,与生物生长、发育、繁殖及遗传变异密切相关。

常见的杂环化合物包括氧茂(呋喃)、硫茂(噻吩)、氮茂(吡咯)、氮苯(吡啶)、氮萘(喹啉)和氮芴(咔唑)等。这些化合物广泛应用于有机合成或作为医药、农药、溶剂等用途,多为无色液体或结晶体,比重小于或接近于水且有毒性,能溶于某些有机溶剂并微溶于水。遇火种、高热、氧化剂和强酸可引发燃烧或爆炸,并释放出有毒的二氧化硫或一氧化氮气体;氧杂茂在空气中易形成过氧化物,在蒸馏时可能发生爆炸。

在危险物品管理中,这些化合物根据火灾、爆炸及毒性的危险程度分别被列为易燃液体、易燃固体和有机毒害品。因此,在储存与使用过程中需按甲、乙类火灾危险性进行消防管理和丙类火灾危险性进行存储分类;发生火灾时,可用泡沫、干粉、雾状水、1211灭火剂或二氧化碳扑救。

下级分类

中文名称 英文名称 CAS号 化学式 结构式图片
—— Benzoic acid, 4-[2-[4-(2-benzoxazolyl)phenyl]ethenyl]- 4763-79-5 C22H15NO3
Benzoic acid, 4-[2-[4-(2-benzoxazolyl)phenyl]ethenyl]-
—— 3H-Pyrazol-3-one, 4-((1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene)-2,4-dihydro-5-methyl-2-phenyl- 5190-63-6 C23H23N3O
3H-Pyrazol-3-one, 4-((1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene)-2,4-dihydro-5-methyl-2-phenyl-
—— 9-Ethylidene-3-oxatricyclo(6.2.1.02,7)undecane-4-one 69486-14-2 C12H16O2
9-Ethylidene-3-oxatricyclo(6.2.1.02,7)undecane-4-one
—— [(3aR,4R,6Z,9R,10Z,11aR)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate 64439-43-6 C22H28O8
[(3aR,4R,6Z,9R,10Z,11aR)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
—— methyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate 221316-61-6 C9H11NO2S
methyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate
—— 5-(tert-butyl) 2-methyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate 1135123-74-8 C14H19NO4S
5-(tert-butyl) 2-methyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate
—— 5,8-Methano-2H-1-benzopyran, 6-ethylideneoctahydro- 93939-86-7 C12H18O
5,8-Methano-2H-1-benzopyran, 6-ethylideneoctahydro-
—— trans-2,3-dimethylpiperidine 5347-68-2 C7H15N
trans-2,3-dimethylpiperidine
—— cis-2,3-Dimethyl-piperidin 5347-68-2 C7H15N
cis-2,3-Dimethyl-piperidin
—— cis-2,3-dimethylpiperidine 5347-68-2 C7H15N
cis-2,3-dimethylpiperidine
—— 4-(6-bromopyridin-2-yl)butanal 1276125-90-6 C9H10BrNO
4-(6-bromopyridin-2-yl)butanal
—— tert-butyl 7-nitro-3,4-dihydro-1,5-naphthyridine-1(2H)-carboxylate 1061148-41-1 C13H17N3O4
tert-butyl 7-nitro-3,4-dihydro-1,5-naphthyridine-1(2H)-carboxylate
—— thietane-3-carbonitrile 1337882-54-8 C4H5NS
thietane-3-carbonitrile
—— 4-nornicotine 130343-15-6 C9H12N2
4-nornicotine
—— 2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetic acid 1620056-83-8 C10H7F5N2O2
2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetic acid
—— 3-(7-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione 191732-75-9 C13H13N3O3
3-(7-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione
—— 3-bromo-8-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyrazine 1334167-29-1 C7H2BrClF3N3
3-bromo-8-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyrazine
—— trans-2-methyltetrahydropyran-4-ol 55230-32-5 C6H12O2
trans-2-methyltetrahydropyran-4-ol
—— cis-2-methyl-4-pyranol 33747-08-9 C6H12O2
cis-2-methyl-4-pyranol
—— (<i>R</i>)-5-methyl-2-thioxo-imidazolidin-4-one 33368-94-4 C4H6N2OS
(<i>R</i>)-5-methyl-2-thioxo-imidazolidin-4-one
—— N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide 1339452-16-2 C7H11N3O2
N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide
—— 5-Bromo-2-((4-methylpiperidin-1-YL)sulfonyl)pyridine 912934-64-6 C11H15BrN2O2S
5-Bromo-2-((4-methylpiperidin-1-YL)sulfonyl)pyridine
—— 7-isopropyl-quinoline 74525-47-6 C12H13N
7-isopropyl-quinoline
—— BTRX-335140 2244614-14-8 C25H32FN5O2
BTRX-335140
—— (2E)-3-(1H-indol-3-yl)prop-2-enoate 1204-06-4 C11H8NO2-
(2E)-3-(1H-indol-3-yl)prop-2-enoate
—— N-(6-(6-chloro-5-(4-fluorophenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide 1162680-13-8 C19H14ClFN6O3S
N-(6-(6-chloro-5-(4-fluorophenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide
—— 2-(1-piperazinyl)quinoline hydrochloride 928026-67-9 C13H15N3*ClH
2-(1-piperazinyl)quinoline hydrochloride
—— 4-Chloro-1-benzothiophene-2-carboxylate 23967-57-9 C9H4ClO2S-
4-Chloro-1-benzothiophene-2-carboxylate
—— 2,6,8-Trimethylquinoline-4-carboxylate 93189-20-9 C13H12NO2-
2,6,8-Trimethylquinoline-4-carboxylate
—— (5-nitro-1H-1,2,4-triazol-3-yl)acetic acid 173167-32-3 C4H4N4O4
(5-nitro-1H-1,2,4-triazol-3-yl)acetic acid
—— 4-Oxazolidinone, 3-ethyl-5-[2-(3-methyl-2-thiazolidinylidene)ethylidene]-2-thioxo- 35795-44-9 C11H14N2O2S2
4-Oxazolidinone, 3-ethyl-5-[2-(3-methyl-2-thiazolidinylidene)ethylidene]-2-thioxo-
—— 1-acetyl-(E)-3-benzylidene-2,5-piperazinedione 30166-29-1 C13H12N2O3
1-acetyl-(E)-3-benzylidene-2,5-piperazinedione
—— [(6Z,10Z)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate 38458-58-1 C22H28O8
[(6Z,10Z)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
—— methyl (2E)-1,3,3-trimethyl-2-[(2Z)-2-(3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)ethylidene]indole-6-carboxylate 5718-26-3 C25H25N3O3
methyl (2E)-1,3,3-trimethyl-2-[(2Z)-2-(3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)ethylidene]indole-6-carboxylate
—— 1'-(1H-indazol-7-ylcarbonyl)-6-methylspiro[chromene-2,4'-piperidin]-4(3H)-one 1031413-61-2 C22H21N3O3
1'-(1H-indazol-7-ylcarbonyl)-6-methylspiro[chromene-2,4'-piperidin]-4(3H)-one
—— 2-(4-chlorophenyl)pyrimidine-5-carboxylic acid 878691-37-3 C11H7ClN2O2
2-(4-chlorophenyl)pyrimidine-5-carboxylic acid
—— 1,3,3-trimethyl-6'-nitrospiro(indoline-2,2'-<2H-1>benzothiopyran) 85000-11-9 C19H18N2O2S
1,3,3-trimethyl-6'-nitrospiro(indoline-2,2'-<2H-1>benzothiopyran)
—— 4-aminothieno[2,3-d]pyrimidine-6-carbaldehyde 655254-90-3 C7H5N3OS
4-aminothieno[2,3-d]pyrimidine-6-carbaldehyde
—— Nitrofurantoin Monohydrate 17140-81-7 C8H8N4O6
Nitrofurantoin Monohydrate
—— Neoglucobrassicin 5187-84-8 C17H22N2O10S2
Neoglucobrassicin
—— (R)-(+)-trans-4-(1-Aminoethyl)-N-(4-Pyridyl)cyclohexanecarboxamide dihydrochloride monohydrate 331752-47-7 C14H25Cl2N3O2
(R)-(+)-trans-4-(1-Aminoethyl)-N-(4-Pyridyl)cyclohexanecarboxamide dihydrochloride monohydrate
—— ONT 093 216227-54-2 C32H38N4O
ONT 093
—— 1,5-bis-(5-nitro-furan-2-yl)-penta-1,4-dien-3-one 2152-70-7 C13H8N2O7
1,5-bis-(5-nitro-furan-2-yl)-penta-1,4-dien-3-one
—— 2-bromo-4-phenylpyrimidine 10198-98-8 C10H7BrN2
2-bromo-4-phenylpyrimidine
—— 5-bromo-2-chloro-3-fluoromethyl-pyridine 1335052-20-4 C6H4BrClFN
5-bromo-2-chloro-3-fluoromethyl-pyridine
—— methyl 6-bromo-5-methylpyrazine-2-carboxylate 1166827-91-3 C7H7BrN2O2
methyl 6-bromo-5-methylpyrazine-2-carboxylate
—— 3-(6-Trifluoromethyl-3-pyridinyl)-2-propenoic acid 773131-93-4 C9H6F3NO2
3-(6-Trifluoromethyl-3-pyridinyl)-2-propenoic acid
—— 4-(3-chlorophenyl)-2,6-diphenylpyridine 83993-80-0 C23H16ClN
4-(3-chlorophenyl)-2,6-diphenylpyridine
—— N'-(6,7-methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamine 500214-39-1 C14H17N3O2
N'-(6,7-methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamine
—— ethyl 4-chlorothieno[2,3-d]pyrimidine-2-carboxylate 1192540-11-6 C9H7ClN2O2S
ethyl 4-chlorothieno[2,3-d]pyrimidine-2-carboxylate