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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
—— 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine 76180-96-6 C11H10N4
3-methyl-3H-imidazo[4,5-f]quinolin-2-amine
—— 2-amino-3-methylimidazo[4,5-f]quinoline 76180-96-6 C11H10N4
2-amino-3-methylimidazo[4,5-f]quinoline
—— 2-amino-3,8-dimethylimidazo<4,5-f>quinoxaline 77500-04-0 C11H11N5
2-amino-3,8-dimethylimidazo<4,5-f>quinoxaline
—— mulberrofuran Q 101383-35-1 C34H24O10
mulberrofuran Q
—— ethyl 2-hydroxy-1,5-naphthyridine-3-carboxylate 55234-61-2 C11H10N2O3
ethyl 2-hydroxy-1,5-naphthyridine-3-carboxylate
—— 4-(hydroxymethyl) piperidine-4-carbonitrile hydrochloride 1345728-51-9 C7H12N2O*ClH
4-(hydroxymethyl) piperidine-4-carbonitrile hydrochloride
—— 3,6-bis(2-methylphenyl)carbazole 850264-86-7 C26H21N
3,6-bis(2-methylphenyl)carbazole
—— 2-chloro-3-(trifluoromethyl)pyridine-1-oxide 164464-57-7 C6H3ClF3NO
2-chloro-3-(trifluoromethyl)pyridine-1-oxide
—— (1R/S,3'R)-(1'-tert-butyloxycarbonyl-2-oxo-[1,3']bipyrrolidinyl-3-yl)-triphenylphosphonium bromide 376653-42-8 Br*C31H36N2O3P
(1R/S,3'R)-(1'-tert-butyloxycarbonyl-2-oxo-[1,3']bipyrrolidinyl-3-yl)-triphenylphosphonium bromide
—— Propan-2-yl 2-butyl-1-benzofuran-5-carboxylate 1447931-32-9 C16H20O3
Propan-2-yl 2-butyl-1-benzofuran-5-carboxylate
—— 3-bromo-1-methyl-1H-pyrrolo[2,3-c]pyridine 956003-06-8 C8H7BrN2
3-bromo-1-methyl-1H-pyrrolo[2,3-c]pyridine
—— 8-Methyl-s-triazolo<4,3-a>pyridin 4997-81-3 C7H7N3
8-Methyl-s-triazolo<4,3-a>pyridin
—— 3-aminofuran 29212-69-9 C4H5NO
3-aminofuran
—— 1-(6-aminohexyl)-2-(6-methyl-pyridin-2-yl)imidazole 341553-78-4 C15H22N4
1-(6-aminohexyl)-2-(6-methyl-pyridin-2-yl)imidazole
—— 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole 1454301-68-8 C19H24BF3N2O3
1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole
—— (R)-HBTM 1316861-19-4 C16H14N2S
(R)-HBTM
—— 5-chloro-1H-indazole-7-carbaldehyde 1100213-27-1 C8H5ClN2O
5-chloro-1H-indazole-7-carbaldehyde
—— 4-bromo-1,3-dihydroisobenzofuran 1402667-16-6 C8H7BrO
4-bromo-1,3-dihydroisobenzofuran
—— 1-propyl-3-methylimidazolium nitrate 649745-76-6 C7H13N2*NO3
1-propyl-3-methylimidazolium nitrate
—— 1-dodecyl-3-methylimidazolium nitrate 799246-93-8 C16H31N2*NO3
1-dodecyl-3-methylimidazolium nitrate
—— Tri-2-pyrryl-phosphin-oxid 953-60-6 C12H12N3OP
Tri-2-pyrryl-phosphin-oxid
—— N,N-dimethyl-1H-pyrazole-3-carboxamide 853058-59-0 C6H9N3O
N,N-dimethyl-1H-pyrazole-3-carboxamide
—— 6-bromo-1H-pyrrolo[3,2-b]pyridin-3-amine 1190319-40-4 C7H6BrN3
6-bromo-1H-pyrrolo[3,2-b]pyridin-3-amine
—— 3,3-dimethyl-dl-proline hydrochloride 61406-78-8 C7H13NO2*ClH
3,3-dimethyl-dl-proline hydrochloride
—— 1H-Pyrrol-1-yloxy, 3-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)-2,5-dihydro-2,2,5,5-tetramethyl- 37558-29-5 C13H18N2O5
1H-Pyrrol-1-yloxy, 3-(((2,5-dioxo-1-pyrrolidinyl)oxy)carbonyl)-2,5-dihydro-2,2,5,5-tetramethyl-
—— 5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one 2847-00-9 C12H18O6
5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one
—— 6-bromo-2,5-dimethyl-1,3-benzothiazole 178396-28-6 C9H8BrNS
6-bromo-2,5-dimethyl-1,3-benzothiazole
—— ethyl 4-tert-butyloxycarbonylamino-1-methylimidazole-2-carboxylate 128293-63-0 C12H19N3O4
ethyl 4-tert-butyloxycarbonylamino-1-methylimidazole-2-carboxylate
—— 3-Amino-2,2,5,5-tetramethylpyrrolidin-1-ol 34272-83-8 C8H18N2O
3-Amino-2,2,5,5-tetramethylpyrrolidin-1-ol
—— 1-Chlor-2-nitro-6,7-dihydro-5H-benzo<ij>chinolizin-3-on 110254-65-4 C12H9ClN2O3
1-Chlor-2-nitro-6,7-dihydro-5H-benzo<ij>chinolizin-3-on
—— 2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-3,8-dimethylquinazolin-4(3H)-one 438450-43-2 C18H12BrCl2N5O
2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-3,8-dimethylquinazolin-4(3H)-one
—— (4-ethyl-2-heptadec-8-enyl-4,5-dihydro-oxazol-4-yl)-methanol 68140-98-7 C23H43NO2
(4-ethyl-2-heptadec-8-enyl-4,5-dihydro-oxazol-4-yl)-methanol
—— 2-Propenoic acid, 3-[5-(4-nitrophenyl)-2-furanyl]-, (E)- 62806-39-7 C13H9NO5
2-Propenoic acid, 3-[5-(4-nitrophenyl)-2-furanyl]-, (E)-
—— Menisperin 25342-82-9 C21H26NO4
Menisperin
—— 5-bromo-2-hydrazinylpyridine hydrochloride 1295647-30-1 C5H6BrN3*ClH
5-bromo-2-hydrazinylpyridine hydrochloride
—— N-(benzothiazol-2-yl)-3,3-diphenylpropanamide 313480-47-6 C22H18N2OS
N-(benzothiazol-2-yl)-3,3-diphenylpropanamide
—— 5-Bromo-2-methylpyrazolo[1,5-a]pyrimidine 1610021-32-3 C7H6BrN3
5-Bromo-2-methylpyrazolo[1,5-a]pyrimidine
—— 4,7-bis(4-isobutoxyphenyl)-2-isobutyl-2H-benzo[d][1,2,3]triazole 1428418-60-3 C30H37N3O2
4,7-bis(4-isobutoxyphenyl)-2-isobutyl-2H-benzo[d][1,2,3]triazole
—— 4,7-dibromo-2-isobutyl-2H-benzo[d][1,2,3]triazole 1428418-59-0 C10H11Br2N3
4,7-dibromo-2-isobutyl-2H-benzo[d][1,2,3]triazole
—— 4-hydroxyl-3-nitro-1,8-naphthalic anhydride 134870-45-4 C12H5NO6
4-hydroxyl-3-nitro-1,8-naphthalic anhydride
—— trans-Perhydroisoindol 1470-99-1 C8H15N
trans-Perhydroisoindol
—— Hexahydroisoindolin 1470-99-1 C8H15N
Hexahydroisoindolin
—— trans-Hexahydroisoindolin 1470-99-1 C8H15N
trans-Hexahydroisoindolin
—— 6,6-dimethylmorpholin-3-one 1312457-13-8 C6H11NO2
6,6-dimethylmorpholin-3-one
—— 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
—— (+)-(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
—— (+)-3-piperidino-propane-1,2-diol 4847-93-2 C8H17NO2
(+)-3-piperidino-propane-1,2-diol
—— 4-bromo-7-fluoro-1,3-benzothiazol-2-amine 942473-89-4 C7H4BrFN2S
4-bromo-7-fluoro-1,3-benzothiazol-2-amine