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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
—— 2-(2,3-dihydrobenzofuran-7-yl)acetonitrile 485828-88-4 C10H9NO
2-(2,3-dihydrobenzofuran-7-yl)acetonitrile
—— Norbornan-exo-2,3-dicarboximid 6713-41-3 C9H11NO2
Norbornan-exo-2,3-dicarboximid
—— trans-3,5-Dimethylpiperidin 14446-75-4 C7H15N
trans-3,5-Dimethylpiperidin
—— methyl 3,5-di-O-benzyl-D-xylofuranoside 102339-30-0 C20H24O5
methyl 3,5-di-O-benzyl-D-xylofuranoside
—— epinodosin 10391-09-0 C20H26O6
epinodosin
—— 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 1269233-11-5 C12H17BClNO2
3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
—— 6-bromo-[1,2,3]triazolo[1,5-a]pyridine 192642-82-3 C6H4BrN3
6-bromo-[1,2,3]triazolo[1,5-a]pyridine
—— 2-(2-chloroindolo[2,3-b]quinoxalin-6-yl)-N-[1-(2-hydroxyphenyl)ethylideneamino]acetamide 109322-06-7 C24H18ClN5O2
2-(2-chloroindolo[2,3-b]quinoxalin-6-yl)-N-[1-(2-hydroxyphenyl)ethylideneamino]acetamide
—— tri(furan-2-yl)phosphine oxide 1021-20-1 C12H9O4P
tri(furan-2-yl)phosphine oxide
—— (5S)-5-ethylfuran-2(5H)-one 2407-43-4 C6H8O2
(5S)-5-ethylfuran-2(5H)-one
—— (1S,3R,4R,7S)-3-(6-N-benzoyladenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 209968-94-5 C18H17N5O5
(1S,3R,4R,7S)-3-(6-N-benzoyladenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
—— 6-oxa-3-azabicyclo[3.1.0]hexane 285-68-7 C4H7NO
6-oxa-3-azabicyclo[3.1.0]hexane
—— germacranolide eucannabinolide 38458-58-1 C22H28O8
germacranolide eucannabinolide
—— benzofuran-6-amine 110677-54-8 C8H7NO
benzofuran-6-amine
—— 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride 157327-44-1 C6H9N3*2ClH
4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride
—— 6-bromo-1,4-dihydro-2H-isoquinolin-3-one 943749-57-3 C9H8BrNO
6-bromo-1,4-dihydro-2H-isoquinolin-3-one
—— 5-bromo-4-methyl-2-(trifluoromethyl)pyrimidine 1100767-04-1 C6H4BrF3N2
5-bromo-4-methyl-2-(trifluoromethyl)pyrimidine
—— N,N-diphenyl pyridin-4-amine 69663-19-0 C17H14N2
N,N-diphenyl pyridin-4-amine
—— tert-butyl 3,3-dimethyl-5-oxopiperidine-1-carboxylate 1000894-83-6 C12H21NO3
tert-butyl 3,3-dimethyl-5-oxopiperidine-1-carboxylate
—— 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride 841275-84-1 C10H9ClN2O4S
1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride
—— 2-(4-bromo-3-fluorophenyl)pyrrolidine 1175528-91-2 C10H11BrFN
2-(4-bromo-3-fluorophenyl)pyrrolidine
—— (6-nitropyridin-3-yl)boronic acid 1236354-21-4 C5H5BN2O4
(6-nitropyridin-3-yl)boronic acid
—— tert-butyl (S)-(1-(3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate 1620056-47-4 C18H18Br2F2N2O2
tert-butyl (S)-(1-(3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate
—— 2-(3-Aminophenyl)butanoic acid 21762-24-3 C10H13NO2
2-(3-Aminophenyl)butanoic acid
—— methyl 4-cyclopropyl-2-fluorobenzoate 1613413-65-2 C11H11FO2
methyl 4-cyclopropyl-2-fluorobenzoate
—— 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole 80278-94-0 C11H13N
1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole
—— ethyl 5-bromo-2-oxopentanoate 57224-29-0 C7H11BrO3
ethyl 5-bromo-2-oxopentanoate
—— (3-((dimethylamino)methyl)oxetan-3-yl)methanol 42987-38-2 C7H15NO2
(3-((dimethylamino)methyl)oxetan-3-yl)methanol
—— 4,6-dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine 21254-22-8 C8H8Cl2N4
4,6-dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine
—— 5-(methoxycarbonyl)-3-methyl-2-pyridone 66909-31-7 C8H9NO3
5-(methoxycarbonyl)-3-methyl-2-pyridone
—— 3-phenyl-2-(triethylsilyl)-1H-indole 1504-16-1 C20H25NSi
3-phenyl-2-(triethylsilyl)-1H-indole
—— ethyl 2-(2H-indazol-2-yl)acetate 954116-90-6 C11H12N2O2
ethyl 2-(2H-indazol-2-yl)acetate
—— indazole radical cation 271-44-3 C7H6N2
indazole radical cation
—— 2-bromothiophene-3-carboxamide 189330-06-1 C5H4BrNOS
2-bromothiophene-3-carboxamide
—— (2S,4R)-4-dimethylamino-pyrrolidine-2-carboxylic acid methyl ester 1163706-98-6 C8H16N2O2
(2S,4R)-4-dimethylamino-pyrrolidine-2-carboxylic acid methyl ester
—— 3-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide 957147-18-1 C23H24F3N3O
3-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide
—— methyl 6-methoxy-2-vinylnicotinate 1384262-70-7 C10H11NO3
methyl 6-methoxy-2-vinylnicotinate
—— ((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 134071-44-6 C21H20Cl2N2O5S
((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)methyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
—— 1-benzyl-4-(2-methoxyphenyl)-1,2,3,6-tetrahydro-pyridine 113411-59-9 C19H21NO
1-benzyl-4-(2-methoxyphenyl)-1,2,3,6-tetrahydro-pyridine
—— 6-nitro-1',3',3'-trimethylspiro(2H-1-benzothiopyran-2,2'-indoline) 85000-11-9 C19H18N2O2S
6-nitro-1',3',3'-trimethylspiro(2H-1-benzothiopyran-2,2'-indoline)
—— 2-ethoxycarbonylmethylthio-5-mercapto-1,3,4-thiadiazole 83123-75-5 C6H8N2O2S3
2-ethoxycarbonylmethylthio-5-mercapto-1,3,4-thiadiazole
—— 3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone 121573-17-9 C9H14O3
3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone
—— (3'R)-3-bromo-1,3'-bipyrrolidin-2-one 1217259-67-0 C8H13BrN2O
(3'R)-3-bromo-1,3'-bipyrrolidin-2-one
—— (4S)-[<sup>2</sup>H]NADPH 74784-45-5 C21H30N7O17P3
(4S)-[<sup>2</sup>H]NADPH
—— 6-(3-methoxyphenyl)imidazo[2,1-b]thiazole 92754-06-8 C12H10N2OS
6-(3-methoxyphenyl)imidazo[2,1-b]thiazole
—— 5-Chloro-7-pyridin-4-yl-1,6-naphthyridine 1211595-82-2 C13H8ClN3
5-Chloro-7-pyridin-4-yl-1,6-naphthyridine
—— 4-(4-bromo-3-(bromomethyl)phenoxy)furo[3,2-c]pyridine 1609581-25-0 C14H9Br2NO2
4-(4-bromo-3-(bromomethyl)phenoxy)furo[3,2-c]pyridine
—— 3-[1-(1H-indol-2-ylmethyl)piperidin-4-yl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one 681277-55-4 C27H28N4O3
3-[1-(1H-indol-2-ylmethyl)piperidin-4-yl]-5-(6-methoxyquinolin-4-yl)-1,3-oxazolidin-2-one
—— (5-fluoro-6-methoxypyridin-3-yl)methanol 959616-65-0 C7H8FNO2
(5-fluoro-6-methoxypyridin-3-yl)methanol
—— 1-(tert-butyl)-3-((5-chloro-3-(hydroxymethyl)pyridin-2-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 1455358-11-8 C18H20ClN3O2
1-(tert-butyl)-3-((5-chloro-3-(hydroxymethyl)pyridin-2-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one