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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
—— [(2,5-Dihydroxyphenyl)methylideneamino]urea —— C8H9N3O3
[(2,5-Dihydroxyphenyl)methylideneamino]urea
—— 4-[(2R)-1,3-oxazinan-2-yl]phenol —— C10H13NO2
4-[(2R)-1,3-oxazinan-2-yl]phenol
—— 4-[(1S)-1-hydroxy-2-(hydroxyamino)ethyl]phenol —— C8H11NO3
4-[(1S)-1-hydroxy-2-(hydroxyamino)ethyl]phenol
—— 3-[(1S)-1-hydroxy-2-(hydroxyamino)ethyl]phenol —— C8H11NO3
3-[(1S)-1-hydroxy-2-(hydroxyamino)ethyl]phenol
—— 3-[(2R)-1,3-oxazolidin-2-yl]phenol —— C9H11NO2
3-[(2R)-1,3-oxazolidin-2-yl]phenol
—— 3-[(2S)-1,3-oxazolidin-2-yl]phenol —— C9H11NO2
3-[(2S)-1,3-oxazolidin-2-yl]phenol
—— 1-[(2S)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C20H27N3O4
1-[(2S)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— N,N-dimethyl-(3,4-dihydroxyphenethyl)sulfamide —— C10H16N2O4S
N,N-dimethyl-(3,4-dihydroxyphenethyl)sulfamide
—— 2-[(3-Bromo-2-hydroxy-5-nitrophenyl)methylidene]-1-benzothiophen-3-one —— C15H8BrNO4S
2-[(3-Bromo-2-hydroxy-5-nitrophenyl)methylidene]-1-benzothiophen-3-one
—— N-[1-(5-chlorothiophen-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C13H11ClN2O4S
N-[1-(5-chlorothiophen-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 4-Cyclohexylsulfanyl-2,6-dinitrophenol —— C12H14N2O5S
4-Cyclohexylsulfanyl-2,6-dinitrophenol
—— 2-cyclopropyl-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylacetamide —— C14H19NO2
2-cyclopropyl-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylacetamide
—— 4-[(3S)-3-(1H-imidazol-2-ylmethylamino)butyl]phenol —— C14H19N3O
4-[(3S)-3-(1H-imidazol-2-ylmethylamino)butyl]phenol
—— 4-bromo-2-(5-ethyl-3-hydroxy-4,4-dimethyl-2H-imidazol-1-ium-2-yl)phenol —— C13H18BrN2O2+
4-bromo-2-(5-ethyl-3-hydroxy-4,4-dimethyl-2H-imidazol-1-ium-2-yl)phenol
—— 3-[(1S)-1-(1H-imidazol-2-ylmethylamino)ethyl]phenol —— C12H15N3O
3-[(1S)-1-(1H-imidazol-2-ylmethylamino)ethyl]phenol
—— 7-ethenyl-8-(2-hydroxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H20O3
7-ethenyl-8-(2-hydroxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3,4,5-trihydroxy-N-[(4-propoxyphenyl)methylideneamino]benzamide —— C17H18N2O5
3,4,5-trihydroxy-N-[(4-propoxyphenyl)methylideneamino]benzamide
—— 1,3-Dihydroxy-4-(1-oximino-butyl)-benzol 22919-59-1 C10H13NO3
1,3-Dihydroxy-4-(1-oximino-butyl)-benzol
—— 2-(4-chlorophenoxy)-N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]propanamide —— C17H17ClN2O4
2-(4-chlorophenoxy)-N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]propanamide
—— 3-[(4-Bromophenyl)methyl]-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H12Br3NO4S
3-[(4-Bromophenyl)methyl]-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 2-[4-(2-Hydroxyphenyl)iminopentan-2-ylideneamino]phenol —— C17H18N2O2
2-[4-(2-Hydroxyphenyl)iminopentan-2-ylideneamino]phenol
—— 2-(4-Hydroxy-3-methylphenyl)-5,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C23H21N3O5
2-(4-Hydroxy-3-methylphenyl)-5,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— 2-hydroxy-5-nitro-N-(thiophen-2-ylmethylideneamino)benzamide —— C12H9N3O4S
2-hydroxy-5-nitro-N-(thiophen-2-ylmethylideneamino)benzamide
—— 2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enamide —— C20H12N4O7
2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enamide
—— 3-[(3,4-Dichlorophenyl)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H13Cl2NO4S
3-[(3,4-Dichlorophenyl)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 7-ethenyl-8-(2-hydroxy-3-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O4
7-ethenyl-8-(2-hydroxy-3-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-nitro-2-(3-pyridin-4-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol —— C14H12N4O3
4-nitro-2-(3-pyridin-4-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol
—— 6-Ethenyl-5-(4-hydroxy-2-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H26O4
6-Ethenyl-5-(4-hydroxy-2-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— 2-(2-Hydroxy-3-nitrophenyl)-3-(4-methoxyphenyl)-1,3-thiazolidin-4-one —— C16H14N2O5S
2-(2-Hydroxy-3-nitrophenyl)-3-(4-methoxyphenyl)-1,3-thiazolidin-4-one
—— ethyl 5-(4-hydroxyphenyl)-7-methyl-2-[(1-methylpyrazol-4-yl)methylidene]-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H20N4O4S
ethyl 5-(4-hydroxyphenyl)-7-methyl-2-[(1-methylpyrazol-4-yl)methylidene]-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C16H10BrClN2O3
4-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— 2-(2,3-Dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H20N2O2S
2-(2,3-Dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-{[Butyl(methyl)amino]methyl}-6-methoxyphenol —— C13H21NO2
2-{[Butyl(methyl)amino]methyl}-6-methoxyphenol
—— 7-(4-hydroxy-3-methoxyphenyl)-5-methyl-N-[3-(trifluoromethyl)phenyl]-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H18F3N5O3
7-(4-hydroxy-3-methoxyphenyl)-5-methyl-N-[3-(trifluoromethyl)phenyl]-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,6-dimethylphenyl)imino-3-phenyl-1,3-thiazolidin-4-one —— C25H21BrN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,6-dimethylphenyl)imino-3-phenyl-1,3-thiazolidin-4-one
—— 2-[5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]-3-oxo-3-pyrrolidin-1-ylpropanenitrile —— C23H17Br2N3O3S
2-[5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]-3-oxo-3-pyrrolidin-1-ylpropanenitrile
—— 2-Bromo-6-methoxy-4-({[2-(pyrrolidin-1-yl)ethyl]amino}methyl)phenol —— C14H21BrN2O2
2-Bromo-6-methoxy-4-({[2-(pyrrolidin-1-yl)ethyl]amino}methyl)phenol
—— 2-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-phenylacetamide —— C16H16N2O4
2-hydroxy-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-phenylacetamide
—— copper;[amino(sulfoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;hydroxide —— C9H13CuN3O3S+2
copper;[amino(sulfoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;hydroxide
—— Ethyl 3-amino-6-(4-hydroxy-3-methoxyphenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C15H19N3O4S
Ethyl 3-amino-6-(4-hydroxy-3-methoxyphenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— Methyl 5-[[5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]furan-2-carboxylate —— C17H11N3O10S
Methyl 5-[[5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]furan-2-carboxylate
—— [4-Chloro-2-(pyridin-2-ylmethyliminomethyl)phenyl]oxidanium;nickel(2+) —— C26H24Cl2N4NiO2+4
[4-Chloro-2-(pyridin-2-ylmethyliminomethyl)phenyl]oxidanium;nickel(2+)
—— N-(2-hydroxy-4-nitrophenyl)-2-(5-nitropyridin-2-yl)sulfanylacetamide —— C13H10N4O6S
N-(2-hydroxy-4-nitrophenyl)-2-(5-nitropyridin-2-yl)sulfanylacetamide
—— (2Z)-2-[(4-chlorophenyl)methylidenehydrazinylidene]-5-[(3,5-dibromo-2,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H10Br2ClN3O3S
(2Z)-2-[(4-chlorophenyl)methylidenehydrazinylidene]-5-[(3,5-dibromo-2,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5,11,17,23,29,35,41,47-Octakis(1-butylcyclopentyl)nonacyclo[43.3.1.13,7.19,13.115,19.121,25.127,31.133,37.139,43]hexapentaconta-1(48),3,5,7(56),9,11,13(55),15,17,19(54),21,23,25(53),27(52),28,30,33(51),34,36,39(50),40,42,45(49),46-tetracosaene-49,50,51,52,53,54,55,56-octol —— C128H176O8
5,11,17,23,29,35,41,47-Octakis(1-butylcyclopentyl)nonacyclo[43.3.1.13,7.19,13.115,19.121,25.127,31.133,37.139,43]hexapentaconta-1(48),3,5,7(56),9,11,13(55),15,17,19(54),21,23,25(53),27(52),28,30,33(51),34,36,39(50),40,42,45(49),46-tetracosaene-49,50,51,52,53,54,55,56-octol
—— 2-[(1R)-1-(2-piperidin-1-ylethylamino)ethyl]phenol —— C15H24N2O
2-[(1R)-1-(2-piperidin-1-ylethylamino)ethyl]phenol
—— 4-[(1R)-1-(2-piperidin-1-ylethylamino)ethyl]phenol —— C15H24N2O
4-[(1R)-1-(2-piperidin-1-ylethylamino)ethyl]phenol
—— 2-[(1S)-1-(2-piperidin-1-ylethylamino)ethyl]phenol —— C15H24N2O
2-[(1S)-1-(2-piperidin-1-ylethylamino)ethyl]phenol
—— 3-[(1R)-1-(2-piperidin-1-ylethylamino)ethyl]phenol —— C15H24N2O
3-[(1R)-1-(2-piperidin-1-ylethylamino)ethyl]phenol
—— 3,5-Dimethyl 1-[(adamantan-1-YL)methyl]-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C27H32ClNO6
3,5-Dimethyl 1-[(adamantan-1-YL)methyl]-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate