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酚类

酚类是一大类化合物,它们主要特征是分子中含有一个羟基(-OH)直接连接在苯环上。这类化合物广泛存在于自然界中,并且具有重要的生物、医药及工业应用价值。

结构与分类

酚类化合物的基本结构为苯环上的氧原子与羟基相连。根据羟基的位置不同,可将酚分为单酚和多酚两大类:

  • 单酚:每个分子仅有一个酚羟基。
  • 多酚:含有两个或多个酚羟基的化合物。
生物学意义
  1. 天然来源:酚广泛存在于植物、动物以及微生物中,如咖啡因中的茶酚、儿茶素等。
  2. 抗氧化作用:许多酚类物质具有较强的抗氧化性,能够清除体内的自由基,保护细胞免受氧化损伤。
  3. 抗菌活性:部分酚类化合物展示出显著的抗菌效果,可用于食品保鲜或开发抗生素。
工业应用
  1. 农药和杀虫剂:利用某些酚类化合物对特定昆虫的选择性毒性进行害虫控制。
  2. 染料工业:许多天然及合成染料都基于酚结构设计而成。
  3. 医药领域:作为原料或药物成分,例如阿司匹林的核心成分水杨酸就属于苯酚衍生物。
工业生产

酚类可以通过多种途径制备:

  • 通过煤焦油蒸馏或石油裂解得到的粗酚进行精炼获得。
  • 以苯或其他芳烃为原料,在催化剂作用下与水反应生成苯酚,此过程称为菲林斯勒反应(Fischer–Strassmann反应)。
注意事项

尽管酚类化合物具有广泛的应用前景,但它们也可能带来毒性问题。例如强酸性的酚类物质会对皮肤造成刺激甚至腐蚀。因此在使用时需注意安全防护措施。

以上是对酚类的简单介绍,涵盖了其基本定义、生物学意义及工业应用等方面的内容。

中文名称 英文名称 CAS号 化学式 结构式图片
—— 2-(2,5-Dimethyl-phenyl)-1,3-diisopropyl-isourea; compound with picric acid 87931-22-4 C6H3N3O7*C15H24N2O
2-(2,5-Dimethyl-phenyl)-1,3-diisopropyl-isourea; compound with picric acid
—— 1,3-Diisopropyl-2-p-tolyl-isourea; compound with picric acid 87931-18-8 C6H3N3O7*C14H22N2O
1,3-Diisopropyl-2-p-tolyl-isourea; compound with picric acid
—— tetraethyl 2,3-dihydroxyphenylethenylidenebisphosphonate 852449-90-2 C16H26O8P2
tetraethyl 2,3-dihydroxyphenylethenylidenebisphosphonate
—— 5-[(2,4-dihydroxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione 273745-68-9 C11H9N3O4
5-[(2,4-dihydroxyphenyl)methylideneamino]-1H-pyrimidine-2,4-dione
—— 1-cyclohexyl-2-(2-hydroxy-5-methoxyphenyl)propan-1-one 1607446-86-5 C16H22O3
1-cyclohexyl-2-(2-hydroxy-5-methoxyphenyl)propan-1-one
—— 4-<Bis-(2-chloraethyl)-amino>-benzyliden-(2-hydroxy-5-nitro)-anilin 103154-30-9 C17H17Cl2N3O3
4-<Bis-(2-chloraethyl)-amino>-benzyliden-(2-hydroxy-5-nitro)-anilin
—— 1399049-48-9 C18H28O3
—— [(18)F]-2-bromo-4-fluorophenol 1393123-16-4 C6H4BrFO
[(18)F]-2-bromo-4-fluorophenol
—— cyclotricatechylene-N,N-dimethylacetamide 75247-89-1 31C4H9NO*10C21H18O6
cyclotricatechylene-N,N-dimethylacetamide
—— tetra-n-butylammonium phenol-phenolate 65801-07-2 C6H5O*C6H6O*C16H36N
tetra-n-butylammonium phenol-phenolate
—— 4-(3-bromo-4-hydroxyphenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile 1033766-80-1 C15H12BrN3O
4-(3-bromo-4-hydroxyphenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile
—— N-p-Hydroxyphenyl-3,5-diacetyl-1,4-dihydropyridine 3246-46-6 C15H15NO3
N-p-Hydroxyphenyl-3,5-diacetyl-1,4-dihydropyridine
—— 1-(4-hydroxyphenyl)-4-heptylbutadiyne 557111-70-3 C17H20O
1-(4-hydroxyphenyl)-4-heptylbutadiyne
—— 92550-86-2 C15H15BrN2O2
—— 2-(5,6-di-<i>p</i>-tolyl-[1,2,4]triazin-3-yl)-4-methyl-phenol 101473-91-0 C24H21N3O
2-(5,6-di-<i>p</i>-tolyl-[1,2,4]triazin-3-yl)-4-methyl-phenol
—— 2-chloro-6-(7-(2-((3-chloro-2-hydroxybenzylidene)amino)ethyl)-3,3-dimethoxy-2-oxa-7,10-diaza-3-silaundec-10-en-11-yl)phenol 1254322-81-0 C24H33Cl2N3O5Si
2-chloro-6-(7-(2-((3-chloro-2-hydroxybenzylidene)amino)ethyl)-3,3-dimethoxy-2-oxa-7,10-diaza-3-silaundec-10-en-11-yl)phenol
—— 2-Acetonyl-3-methoxy-5-methyl-hydrochinon 96418-38-1 C11H14O4
2-Acetonyl-3-methoxy-5-methyl-hydrochinon
—— 4-(4,4,4-trifluorobutoxy)phenol 1345477-54-4 C10H11F3O2
4-(4,4,4-trifluorobutoxy)phenol
—— 1,3-bis(4-hydroxybenzyl)urea 101112-95-2 C15H16N2O3
1,3-bis(4-hydroxybenzyl)urea
—— N-Undecanoyl-tyramin 21469-30-7 C19H31NO2
N-Undecanoyl-tyramin
—— 6-Oxo-1-phenethyl-1,6-dihydro-pyridine-3-carboxylic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 6434-03-3 C22H21N3O4
6-Oxo-1-phenethyl-1,6-dihydro-pyridine-3-carboxylic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide
—— salicylaldehyde-N,N-di(iso-propyl) semicarbazone 637748-81-3 C14H21N3O2
salicylaldehyde-N,N-di(iso-propyl) semicarbazone
—— (4R,5R)-4trans-Aminocarbonyl-4-methyl-5ref-(3-hydroxy-phenyl)-oxazolidinon-(2) 16096-48-3 C11H12N2O4
(4R,5R)-4trans-Aminocarbonyl-4-methyl-5ref-(3-hydroxy-phenyl)-oxazolidinon-(2)
—— 2-(5-phenyl-1-pentyn-1-yl)phenol 1398505-11-7 C17H16O
2-(5-phenyl-1-pentyn-1-yl)phenol
—— 2-diethylphosphoryl-5-methylphenol 129529-19-7 C11H17O2P
2-diethylphosphoryl-5-methylphenol
—— 4-(4-hydroxy-3-methoxy-phenyl)-4-(6-methyl-pyridin-2-ylamino)-2-oxo-butyric acid 13225-83-7 C17H18N2O5
4-(4-hydroxy-3-methoxy-phenyl)-4-(6-methyl-pyridin-2-ylamino)-2-oxo-butyric acid
—— 1,4,8,11-tetrakis(2-(5-chlorosalicylideneamino)ethyl)-1,4,8,11-tetraazacyclotetradecane 164594-64-3 C46H56Cl4N8O4
1,4,8,11-tetrakis(2-(5-chlorosalicylideneamino)ethyl)-1,4,8,11-tetraazacyclotetradecane
—— 5-methoxy-2-(phenylethynyl)phenol 1259295-19-6 C15H12O2
5-methoxy-2-(phenylethynyl)phenol
—— (S)-(+)-2-(4-hydroxyphenyl) propionic acid 2,2,2-trifluoroethylester 164210-24-6 C11H11F3O3
(S)-(+)-2-(4-hydroxyphenyl) propionic acid 2,2,2-trifluoroethylester
—— 4,4’-{[5,5’-(ethane-1,2-diyl)]di(1,3,4-thiadiazol-2-yl)}di(benzene-1,3-diol) 1447735-06-9 C18H14N4O4S2
4,4’-{[5,5’-(ethane-1,2-diyl)]di(1,3,4-thiadiazol-2-yl)}di(benzene-1,3-diol)
—— 3-Methoxy-4-hydroxy-2,5-toluhydrochinon 1127-61-3 C8H10O4
3-Methoxy-4-hydroxy-2,5-toluhydrochinon
—— 2-Fluor-5,8-dihydro-naphthohydrochinon-(1,4) 773-75-1 C10H9FO2
2-Fluor-5,8-dihydro-naphthohydrochinon-(1,4)
—— 2-hydroxy-benzaldehyde <i>S</i>-(3-chloro-[1,2,4]thiadiazol-5-yl)-thiooxime 59918-26-2 C9H6ClN3OS2
2-hydroxy-benzaldehyde <i>S</i>-(3-chloro-[1,2,4]thiadiazol-5-yl)-thiooxime
—— (2S)-2-amino-3-{[(2-hydroxy-3-nitro-5-sulfophenyl)carbamoyl]amino}propanoic acid 1333219-21-8 C10H12N4O9S
(2S)-2-amino-3-{[(2-hydroxy-3-nitro-5-sulfophenyl)carbamoyl]amino}propanoic acid
—— 3,6-dibromo-2,4-dimethylphenol 83755-91-3 C8H8Br2O
3,6-dibromo-2,4-dimethylphenol
—— 3-amino-2-bromo-4,6-dinitro-phenol 855836-13-4 C6H4BrN3O5
3-amino-2-bromo-4,6-dinitro-phenol
—— 5-hydroxy-2-phenoxidothiolanium zwitterion 123192-57-4 C10H12O2S
5-hydroxy-2-phenoxidothiolanium zwitterion
—— 3-Chloro-2,5-dihydroxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid methyl ester 110137-84-3 C10H9ClO4
3-Chloro-2,5-dihydroxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid methyl ester
—— 3-Hydroxy-thiobenzoesaeure-O-aethylester 13806-80-9 C9H10O2S
3-Hydroxy-thiobenzoesaeure-O-aethylester
—— (4S,5S)-N,N'-bis(2-hydroxy-5-methylphenyl)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide 443287-87-4 C21H24N2O6
(4S,5S)-N,N'-bis(2-hydroxy-5-methylphenyl)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide
—— 2,4-bis-(3-morpholin-4-yl-prop-1-ynyl)-phenol 30427-58-8 C20H24N2O3
2,4-bis-(3-morpholin-4-yl-prop-1-ynyl)-phenol
—— 2-(2,4-dihydroxy-3-methylphenyl)-3a-hydroxy-3a,6-dihydro[1,3]thiazolo[5,4-d]pyrimidin-5(4H)-one 1376272-93-3 C12H11N3O4S
2-(2,4-dihydroxy-3-methylphenyl)-3a-hydroxy-3a,6-dihydro[1,3]thiazolo[5,4-d]pyrimidin-5(4H)-one
—— 3-(3,4-dihydroxyphenyl)-2-(3-oxo-5,6-diphenyl-1,2,4-triazin-2(3H)-yl)acrylic acid 1252069-43-4 C24H17N3O5
3-(3,4-dihydroxyphenyl)-2-(3-oxo-5,6-diphenyl-1,2,4-triazin-2(3H)-yl)acrylic acid
—— 4-iodo-2,3,5-trimethyl-phenol 7282-02-2 C9H11IO
4-iodo-2,3,5-trimethyl-phenol
—— 2-[bis(2-hydroxy-5-nitrobenzyl)aminomethyl]pyridine 155797-30-1 C20H18N4O6
2-[bis(2-hydroxy-5-nitrobenzyl)aminomethyl]pyridine
—— 3-(4-acetoxybutyl)-4-methoxyphenol 111088-08-5 C13H18O4
3-(4-acetoxybutyl)-4-methoxyphenol
—— 2-[4-methoxyl-3-(pent-1-enyl)phenyl]ethanol 1201954-93-9 C14H20O2
2-[4-methoxyl-3-(pent-1-enyl)phenyl]ethanol
—— 2-((E)-3-Butoxy-1-methyl-allyl)-phenol 18062-16-3 C14H20O2
2-((E)-3-Butoxy-1-methyl-allyl)-phenol
—— N,N'-bis(4-nitrosalicylidene)diethylenetriamine 101079-16-7 C18H19N5O6
N,N'-bis(4-nitrosalicylidene)diethylenetriamine
—— [1-(2-hydroxy-4,6-dimethoxy-phenyl)-methylidene]-pyridine-2-carboxylic acid hydrazide 1312798-10-9 C15H15N3O4
[1-(2-hydroxy-4,6-dimethoxy-phenyl)-methylidene]-pyridine-2-carboxylic acid hydrazide