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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
—— 6,7-dichloro-1H-indole-2-carboxylic acid 383132-13-6 C9H5Cl2NO2
6,7-dichloro-1H-indole-2-carboxylic acid
—— trans-Perhydroisoindol 1470-99-1 C8H15N
trans-Perhydroisoindol
—— 1-Methyl-6-oxo-pyridazine-3-carboxylate 100047-66-3 C6H5N2O3-
1-Methyl-6-oxo-pyridazine-3-carboxylate
—— Hexahydroisoindolin 1470-99-1 C8H15N
Hexahydroisoindolin
—— trans-Hexahydroisoindolin 1470-99-1 C8H15N
trans-Hexahydroisoindolin
—— 3-Azatricyclo<3.2.1.0<sup>2,4exo</sup>>-octan 279-82-3 C7H13N
3-Azatricyclo<3.2.1.0<sup>2,4exo</sup>>-octan
—— 2,3,4,6-tetra-O-benzyl-L-idopyranose 4132-28-9 C34H36O6
2,3,4,6-tetra-O-benzyl-L-idopyranose
—— Tetra-O-benzyl-D-galactopyranose 4132-28-9 C34H36O6
Tetra-O-benzyl-D-galactopyranose
—— (5R)-5-aminopiperidin-2-one 1002566-99-5 C5H10N2O
(5R)-5-aminopiperidin-2-one
—— 1,2-dihydro-2-oxo-6-(2-pyridyl)-3-pyridinecarbonitrile 56304-74-6 C11H7N3O
1,2-dihydro-2-oxo-6-(2-pyridyl)-3-pyridinecarbonitrile
—— cis-2,3-dichlorotetrahydrofuran 3511-19-1 C4H6Cl2O
cis-2,3-dichlorotetrahydrofuran
—— 2-(2-bromo-4-fluorophenyl)pyrrolidine 1016499-98-1 C10H11BrFN
2-(2-bromo-4-fluorophenyl)pyrrolidine
—— (2S,4S)-4-Benzhydryl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 959573-18-3 C23H27NO4
(2S,4S)-4-Benzhydryl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
—— 6-bromo-quinoxalin-2-ylamine 1071605-38-3 C8H6BrN3
6-bromo-quinoxalin-2-ylamine
—— 2-Cyano-3-pyridin-3-ylprop-2-enoic acid 103029-74-9 C9H6N2O2
2-Cyano-3-pyridin-3-ylprop-2-enoic acid
—— (E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic acid 75028-24-9 C6H8N4O3S
(E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic acid
—— 7-Methylamino-4-trifluoromethyl-chromen-2-one 53518-14-2 C11H8F3NO2
7-Methylamino-4-trifluoromethyl-chromen-2-one
—— Methyl 4-hydroxy-2-(trifluoromethyl)thieno[3,4-b]pyridine-7-carboxylate 175203-39-1 C10H6F3NO3S
Methyl 4-hydroxy-2-(trifluoromethyl)thieno[3,4-b]pyridine-7-carboxylate
—— (+)-(R)-N-(4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide 1428652-17-8 C22H25N3O2
(+)-(R)-N-(4-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide
—— (2,6-dichloro-phenyl)-pyrimidin-2-yl-amine 66501-16-4 C10H7Cl2N3
(2,6-dichloro-phenyl)-pyrimidin-2-yl-amine
—— 3-(3-carboxypropyl)-7-sulfomethyl-1H-indole-2-carboxylic acid ethyl ester 860398-31-8 C16H19NO7S
3-(3-carboxypropyl)-7-sulfomethyl-1H-indole-2-carboxylic acid ethyl ester
—— 4-methyl-4,7-diazaspiro[2.5]octane 1152367-88-8 C7H14N2
4-methyl-4,7-diazaspiro[2.5]octane
—— Disodium 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-1H-pyrazole-3-carboxylate 3473-75-4 C10H6N2Na2O6S
Disodium 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-1H-pyrazole-3-carboxylate
—— (+)-3-piperidino-propane-1,2-diol 4847-93-2 C8H17NO2
(+)-3-piperidino-propane-1,2-diol
—— 7-bromo-5-methoxyindole 408355-12-4 C9H8BrNO
7-bromo-5-methoxyindole
—— tert-butyl (S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 103733-66-0 C16H23NO4
tert-butyl (S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
—— 4-bromo-7-fluoro-1,3-benzothiazol-2-amine 942473-89-4 C7H4BrFN2S
4-bromo-7-fluoro-1,3-benzothiazol-2-amine
—— 4-bromo-1-(4-methoxyphenyl)-1H-pyrazole 1215007-02-5 C10H9BrN2O
4-bromo-1-(4-methoxyphenyl)-1H-pyrazole
—— 5-aminoindoline dihydrochloride 2759-14-0 C8H10N2*2ClH
5-aminoindoline dihydrochloride
—— methyl 7-bromo-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate 1301214-77-6 C9H7BrN2O3
methyl 7-bromo-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate
—— (E)-N’-(5-bromopyrazin-2-yl)-N,N-dimethylformamidine 1245215-89-7 C7H9BrN4
(E)-N’-(5-bromopyrazin-2-yl)-N,N-dimethylformamidine
—— (6-Bromo-2-oxo-benzooxazol-3-yl)-acetic acid 100219-71-4 C9H6BrNO4
(6-Bromo-2-oxo-benzooxazol-3-yl)-acetic acid
—— (R)-4-benzyl-2-(pyridin-2-yl)-4,5-dihydrooxazole 108915-08-8 C15H14N2O
(R)-4-benzyl-2-(pyridin-2-yl)-4,5-dihydrooxazole
—— 4-vinylpyridine cation 100-43-6 C7H7N
4-vinylpyridine cation
—— 7-chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 1202780-76-4 C6H4ClN3O
7-chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
—— N,N-tris[[1-(pyren-1-ylmethyl)-1H-1,2,3-triazol-4-yl]methyl]-amine 1402329-58-1 C60H42N10
N,N-tris[[1-(pyren-1-ylmethyl)-1H-1,2,3-triazol-4-yl]methyl]-amine
—— 4-Ammonio-1-benzylpiperidinium dichloride 1205-72-7 C12H18ClN2-
4-Ammonio-1-benzylpiperidinium dichloride
—— 2-Chloro-1-methylpyridinium toluene-p-sulphonate 7403-46-5 C13H15ClNO3S+
2-Chloro-1-methylpyridinium toluene-p-sulphonate
—— Einecs 225-633-1 4983-38-4 C16H24ClN2-
Einecs 225-633-1
—— (1S-(1alpha,3Abeta,4alpha,8abeta,9R*))-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-methanol 1139-17-9 C15H26O
(1S-(1alpha,3Abeta,4alpha,8abeta,9R*))-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-methanol
—— 1-Benzyl-4-(dimethylammonio)piperidinium dichloride 4876-56-6 C14H22ClN2-
1-Benzyl-4-(dimethylammonio)piperidinium dichloride
—— 4-Methylpyrimidine-2-thiol HCl 6959-66-6 C5H6ClN2S-
4-Methylpyrimidine-2-thiol HCl
—— (8alpha,9R)-1-Benzyl-9-hydroxycinchonanium chloride 69257-04-1 C26H30ClN2O+
(8alpha,9R)-1-Benzyl-9-hydroxycinchonanium chloride
—— N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(Z)-3-[[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-hydroxypent-2-en-3-yl]disulfanyl]-5-hydroxypent-2-en-2-yl]formamide 67-16-3 C24H34N8O4S2
N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(Z)-3-[[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-hydroxypent-2-en-3-yl]disulfanyl]-5-hydroxypent-2-en-2-yl]formamide
—— Pyrimidine-4,6-diammonium hydrogen sulphate (1:2) 77709-02-5 C4H8N4O
Pyrimidine-4,6-diammonium hydrogen sulphate (1:2)
—— D,L-2,2-di(2-tetrahydrofuryl)propane 89686-69-1 C11H20O2
D,L-2,2-di(2-tetrahydrofuryl)propane
—— Cinchonidine sulfate dihydrate 524-61-8 C38H50N4O8S
Cinchonidine sulfate dihydrate
—— (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride 69221-14-3 C26H29ClN2O
(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride
—— 8-Azepan-2-YL-quinoline 527673-84-3 C15H18N2
8-Azepan-2-YL-quinoline
—— 5-Bromo-2,3-dihydro-3,3-dimethylbenzofuran-2-one 75097-60-8 C10H9BrO2
5-Bromo-2,3-dihydro-3,3-dimethylbenzofuran-2-one