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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
—— 4-n-octyl-2-fluorophenol —— C14H21FO
4-n-octyl-2-fluorophenol
—— (3,5-dihydroxy-benzyl)-phosphonic acid dimethyl ester —— C9H13O5P
(3,5-dihydroxy-benzyl)-phosphonic acid dimethyl ester
—— 4-[2-(3-Phenoxy-propylamino)-ethoxy]-phenol monohydrobromide —— BrH*C17H21NO3
4-[2-(3-Phenoxy-propylamino)-ethoxy]-phenol monohydrobromide
—— 2-methyl-undecyl-calix[4]resorcinarene —— C76H120O8
2-methyl-undecyl-calix[4]resorcinarene
—— 2-(4-hydroxy-3-methoxyphenyl)-7-(thiophen-2-yl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one —— C21H14F3N3O3S2
2-(4-hydroxy-3-methoxyphenyl)-7-(thiophen-2-yl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one
—— 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine —— C26H28N2O8
2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine
—— Methyl 2-(4-hydroxyphenyl)ethanimidate;hydrochloride —— C9H11NO2*ClH
Methyl 2-(4-hydroxyphenyl)ethanimidate;hydrochloride
—— (E,E)-2-(benzylaminocarbonyl)-3-(4-hydroxy-3-methoxystyryl)acrylonitrile —— C20H18N2O3
(E,E)-2-(benzylaminocarbonyl)-3-(4-hydroxy-3-methoxystyryl)acrylonitrile
—— 2-bromo-5-chlorobenzene-1,3-diol —— C6H4BrClO2
2-bromo-5-chlorobenzene-1,3-diol
—— (E)-4-((pyridin-3-ylmethylene)amino)phenol —— C12H10N2O
(E)-4-((pyridin-3-ylmethylene)amino)phenol
—— N,N'-bis-tyramine urea —— C17H20N2O3
N,N'-bis-tyramine urea
—— (R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester —— C12H13NO4
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester
—— (S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester —— C12H13NO4
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester
—— 2-methoxy-4-(6-[[(1S)-1-phenylpropyl]amino]pyrazin-2-yl)phenol —— C20H21N3O2
2-methoxy-4-(6-[[(1S)-1-phenylpropyl]amino]pyrazin-2-yl)phenol
—— citreofuran —— C16H16O5
citreofuran
—— 2,3,5,6-tetranitro-resorcinol —— C6H2N4O10
2,3,5,6-tetranitro-resorcinol
—— 2-(3-heptyl-3-hydroxydecyl)-phenol —— C23H40O2
2-(3-heptyl-3-hydroxydecyl)-phenol
—— 3,4,5-trihydroxy-N'-(3-((3-methoxybenzyl)oxy)benzylidene)benzohydrazide —— C22H20N2O6
3,4,5-trihydroxy-N'-(3-((3-methoxybenzyl)oxy)benzylidene)benzohydrazide
—— (E)-3,4,5-trihydroxy-N'-(3-(3-methoxybenzyloxy)phenylmethylidene)benzohydrazide —— C22H20N2O6
(E)-3,4,5-trihydroxy-N'-(3-(3-methoxybenzyloxy)phenylmethylidene)benzohydrazide
—— N-benzyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanamide —— C17H16Br2N2O4
N-benzyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanamide
—— 2-(2-hydroxy-ethylsulfanylmethyl)phenol —— C9H12O2S
2-(2-hydroxy-ethylsulfanylmethyl)phenol
—— o-nitro-p-isobutylphenol —— C10H13NO3
o-nitro-p-isobutylphenol
—— (Z)-1-(4'-hydroxyphenyl)octadec-13-en-5-one —— C24H38O2
(Z)-1-(4'-hydroxyphenyl)octadec-13-en-5-one
—— (E)-1-(4'-hydroxyphenyl)octadec-13-en-5-one —— C24H38O2
(E)-1-(4'-hydroxyphenyl)octadec-13-en-5-one
—— 2-(2-hydroxy-3,5-dinitrophenyl)-5-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,4-oxadiazole —— C13H8N6O8
2-(2-hydroxy-3,5-dinitrophenyl)-5-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,4-oxadiazole
—— 1-(2-hydroxyphenyl)-5-phenyl-3-pentanol —— C17H20O2
1-(2-hydroxyphenyl)-5-phenyl-3-pentanol
—— 2-ethyl-4,6,7-trimethyl-2,3-dihydrobenzo[b]selenophen-5-ol —— C13H18OSe
2-ethyl-4,6,7-trimethyl-2,3-dihydrobenzo[b]selenophen-5-ol
—— 5,11,17,23-tetrakis<(diallylamino)methyl>-25,26,27,28-tetrahydroxycalix<4>arene —— C56H68N4O4
5,11,17,23-tetrakis<(diallylamino)methyl>-25,26,27,28-tetrahydroxycalix<4>arene
—— 3-methoxysalicylaldehyde-4(N)-ethylthiosemicarbazone 301202-22-2 C11H15N3O2S
3-methoxysalicylaldehyde-4(N)-ethylthiosemicarbazone
—— dihydro-3-(2-(4-hydroxy-3-methoxyphenyl)ethylidene)furan-2(3H)-one —— C13H14O4
dihydro-3-(2-(4-hydroxy-3-methoxyphenyl)ethylidene)furan-2(3H)-one
—— 3-methoxysalicylaldehyde-4(N)-phenylthiosemicarbazone —— C15H15N3O2S
3-methoxysalicylaldehyde-4(N)-phenylthiosemicarbazone
—— 1-(2-hydroxy-phenyl)-hexan-3-one —— C12H16O2
1-(2-hydroxy-phenyl)-hexan-3-one
—— monochasiol C —— C21H35ClO2
monochasiol C
—— methyl 3-(5-{(Z)-[6-(4-hydroxy-3-methoxyphenyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrol-3-yl)propanoate —— C26H26N2O5
methyl 3-(5-{(Z)-[6-(4-hydroxy-3-methoxyphenyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrol-3-yl)propanoate
—— diethyl {4-[(2-hydroxy-5-methylphenyl)carbonyl]-1-phenyl-2H-pyrazol-3-yl}phosphonate —— C21H25N2O5P
diethyl {4-[(2-hydroxy-5-methylphenyl)carbonyl]-1-phenyl-2H-pyrazol-3-yl}phosphonate
—— 1,5-Bis(2-hydroxyphenyl)-pentan-3-ol —— C17H20O3
1,5-Bis(2-hydroxyphenyl)-pentan-3-ol
—— methyl 6-amino-5-cyano-4-(4'-hydroxy-phenyl)-2-methyl-4H-pyran-3-carboxylate —— C15H14N2O4
methyl 6-amino-5-cyano-4-(4'-hydroxy-phenyl)-2-methyl-4H-pyran-3-carboxylate
—— 5-(5-chloro-2,4-dihydroxy-phenyl)-4-(4-diethylaminomethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide —— C23H26ClN3O4
5-(5-chloro-2,4-dihydroxy-phenyl)-4-(4-diethylaminomethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide
—— 5,11,17,23-tetrakis(azidomethyl)-25,26,27,28-tetrahydroxycalix<4>arene —— C32H28N12O4
5,11,17,23-tetrakis(azidomethyl)-25,26,27,28-tetrahydroxycalix<4>arene
—— 5-(3,4-dihydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione —— C13H12O6
5-(3,4-dihydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
—— (E)-3,4,5-trihydroxy-N'-(benzyloxyphenylmethylidene)benzohydrazide —— C21H18N2O5
(E)-3,4,5-trihydroxy-N'-(benzyloxyphenylmethylidene)benzohydrazide
—— N'-(4-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide —— C21H18N2O5
N'-(4-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide
—— N-nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine —— C12H15N3O7
N-nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine
—— 4-chloro-3-(4-(3,3-difluoro-1-methylpiperidin-4-ylamino)-6-(3,5-dimethylisoxazol-4-yl)-5-methylpyrimidin-2-yl)phenol —— C22H24ClF2N5O2
4-chloro-3-(4-(3,3-difluoro-1-methylpiperidin-4-ylamino)-6-(3,5-dimethylisoxazol-4-yl)-5-methylpyrimidin-2-yl)phenol
—— 5(Z)-3-benzyl-5-(2-hydroxybenzylidene)furan-2(5H)-one —— C18H14O3
5(Z)-3-benzyl-5-(2-hydroxybenzylidene)furan-2(5H)-one
—— rubrolide K —— C17H9Br2ClO4
rubrolide K
—— Z-2-(4'-hydroxy-3'-methylbut-2'-enyl)-4-methoxyphenol —— C12H16O3
Z-2-(4'-hydroxy-3'-methylbut-2'-enyl)-4-methoxyphenol
—— N-(4-cyclohexylidenecyclohexyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide —— C21H29NO3
N-(4-cyclohexylidenecyclohexyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— Ethyl [2-(2,3-difluoro-4-hydroxyphenyl)cyclopropyl]acetate —— C13H14F2O3
Ethyl [2-(2,3-difluoro-4-hydroxyphenyl)cyclopropyl]acetate
—— 5-(4-[2-(4-trifluoromethanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione —— C19H14F3NO6S2
5-(4-[2-(4-trifluoromethanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione