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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
—— 1,5-di(2-thienyl)-1,4-pentadien-3-one 886-78-2 C13H10OS2
1,5-di(2-thienyl)-1,4-pentadien-3-one
—— 1,4-bis(tetrahydro-2H-pyran-2-yloxy)benzene 2139-44-8 C16H22O4
1,4-bis(tetrahydro-2H-pyran-2-yloxy)benzene
—— (3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone 133066-59-8 C11H11NO3
(3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone
—— N-(isopentyl)-quinolinium iodide 54899-89-7 C14H18N*I
N-(isopentyl)-quinolinium iodide
—— cis-1,2-cyclopropanedicarboxylic acid anhydride 5617-74-3 C5H4O3
cis-1,2-cyclopropanedicarboxylic acid anhydride
—— N-Methylisoguvacine 68947-50-2 C7H11NO2
N-Methylisoguvacine
—— 6-fluoro-1,2,3,4-tetrahydrobenzo[4,5]thieno[2,3-c]pyridine 685086-10-6 C11H10FNS
6-fluoro-1,2,3,4-tetrahydrobenzo[4,5]thieno[2,3-c]pyridine
—— tert-butyl (4R,5R)-2,2-dimethyl-4-[4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]-3-oxobutyl]-5-phenyl-1,3-oxazolidine-3-carboxylate 1426235-02-0 C31H42N2O6
tert-butyl (4R,5R)-2,2-dimethyl-4-[4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]-3-oxobutyl]-5-phenyl-1,3-oxazolidine-3-carboxylate
—— N-Fmoc-(O-N-acetylgalactosaminyl)threonine tert-butyl ester 189561-75-9 C31H40N2O10
N-Fmoc-(O-N-acetylgalactosaminyl)threonine tert-butyl ester
—— 1-aminodibenzothiophene 29451-76-1 C12H9NS
1-aminodibenzothiophene
—— 3,3'-diethyloxacarbocyanine iodide 905-96-4 C21H21N2O2*I
3,3'-diethyloxacarbocyanine iodide
—— N-Methylfulleropyrrolidine 151872-44-5 C63H7N
N-Methylfulleropyrrolidine
—— atogepant 1374248-81-3 C29H23F6N5O3
atogepant
—— 1-oxy-pyrazine-2,6-diamine 41536-72-5 C4H6N4O
1-oxy-pyrazine-2,6-diamine
—— 4-methoxyphenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 38229-78-6 C15H21NO7
4-methoxyphenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside
—— 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]-4-methylpiperazine 1293489-87-8 C19H24N2S
1-[2-(2,4-dimethylphenylsulfanyl)phenyl]-4-methylpiperazine
—— 1-benzyl-1,2,3,6-tetrahydropyridin-4-en-3-one 94923-25-8 C12H13NO
1-benzyl-1,2,3,6-tetrahydropyridin-4-en-3-one
—— ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 145032-58-2 C8H10O4
ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate
—— squaramide 473727-83-2 C21H23N3O5
squaramide
—— (23S)-3α,7α,23-trihydroxy-5β-cholan-24-oic acid 105880-09-9 C24H40O5
(23S)-3α,7α,23-trihydroxy-5β-cholan-24-oic acid
—— methyl 5-isoquinolyloxyacetate 130292-81-8 C12H11NO3
methyl 5-isoquinolyloxyacetate
—— 8-chloro-3-iodoquinoline 847727-21-3 C9H5ClIN
8-chloro-3-iodoquinoline
—— N-[5-(4-bromophenyl)-6-chloro-4-pyrimidinyl]-N'-benzyl-sulfamide 441797-42-8 C17H14BrClN4O2S
N-[5-(4-bromophenyl)-6-chloro-4-pyrimidinyl]-N'-benzyl-sulfamide
—— 1,3,4-thiadiazole-2-carbonitrile 1121585-02-1 C3HN3S
1,3,4-thiadiazole-2-carbonitrile
—— ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate 96568-04-6 C10H8Cl2FNO3
ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate
—— 5-(but-1-yn-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 1365889-00-4 C16H18N2O
5-(but-1-yn-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
—— N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide 137281-08-4 C11H14N4O2
N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide
—— 2,4-di(pyridin-4-yl)-1,3,5-triazine 39238-43-2 C13H9N5
2,4-di(pyridin-4-yl)-1,3,5-triazine
—— 2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-ol 112281-82-0 C11H11Cl2N3O
2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-ol
—— tert-butyl 4-cyano-4-(3,4-difluorophenyl)piperidine-1-carboxylate 906369-56-0 C17H20F2N2O2
tert-butyl 4-cyano-4-(3,4-difluorophenyl)piperidine-1-carboxylate
—— 3-(3,5-dimethyl-1H-pyrazol-4-yl)propane-1-ol 1779428-05-5 C8H14N2O
3-(3,5-dimethyl-1H-pyrazol-4-yl)propane-1-ol
—— N-Benzylquinidinium chloride, 98% 77481-82-4 C27H31ClN2O2
N-Benzylquinidinium chloride, 98%
—— 2,2′-((2,6)-1-methylpiperidine-2,6-diyl)bis(1-phenylethanone) hydrochloride 6168-88-3 C22H25NO2*ClH
2,2′-((2,6)-1-methylpiperidine-2,6-diyl)bis(1-phenylethanone) hydrochloride
—— 2-(2-aminoethyl)benzimidazole dihydrochloride 4499-07-4 C9H11N3*2ClH
2-(2-aminoethyl)benzimidazole dihydrochloride
—— 6-(2-methyl-2-propenyl)imidazo<1,2-a>pyridine 116355-20-5 C11H12N2
6-(2-methyl-2-propenyl)imidazo<1,2-a>pyridine
—— 1-(imidazo[1,2-a]pyridin-6-yl)-2-propanone 116355-08-9 C10H10N2O
1-(imidazo[1,2-a]pyridin-6-yl)-2-propanone
—— difelikefalin 1024828-77-0 C36H53N7O6
difelikefalin
—— adenosine 5'-diphosphate sodium salt 20398-34-9 C10H14N5O10P2*Na
adenosine 5'-diphosphate sodium salt
—— (1R,5S)-7-benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one 77716-01-9 C14H17NO2
(1R,5S)-7-benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one
—— 9-allyl-9H-carbazole 3998-04-7 C15H13N
9-allyl-9H-carbazole
—— 2-methyl-3-benzylindole 19006-14-5 C16H15N
2-methyl-3-benzylindole
—— 4-((R)-2-{[6-((S)-3-methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carbonyl]amino}-3-phosphonopropionyl)piperazine-1-carboxylic acid butyl ester 1159500-34-1 C28H39N6O8P
4-((R)-2-{[6-((S)-3-methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carbonyl]amino}-3-phosphonopropionyl)piperazine-1-carboxylic acid butyl ester
—— 1-(p-bromophenacyl)pyridinium bromide 17282-37-0 Br*C13H11BrNO
1-(p-bromophenacyl)pyridinium bromide
—— 4'-(methoxycarbonyl)-[2,2'-bipyridine]-4-carboxylic acid 161955-60-8 C13H10N2O4
4'-(methoxycarbonyl)-[2,2'-bipyridine]-4-carboxylic acid
—— Neo Heliopan AP Sodium Salt 180898-37-7 C20H14N4NaO12S4
Neo Heliopan AP Sodium Salt
—— {[3,3-dibutyl-7-(methylsulfanyl)-1,1-dioxido-5-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepin-8-yl]oxy}acetic acid 439088-13-8 C26H35NO5S2
{[3,3-dibutyl-7-(methylsulfanyl)-1,1-dioxido-5-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepin-8-yl]oxy}acetic acid
—— 5,6-dimethoxy-2-methoxycarbonylindan-1-one 119035-03-9 C13H14O5
5,6-dimethoxy-2-methoxycarbonylindan-1-one
—— 2,5-bis(4-pyridyl)thiazolo[5,4-d]thiazole 97193-46-9 C14H8N4S2
2,5-bis(4-pyridyl)thiazolo[5,4-d]thiazole
—— (S)-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide 1025505-82-1 C3H7NO3S
(S)-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide
—— 6-bromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 1059630-11-3 C11H11BrN2*ClH
6-bromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride