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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-methoxy-4-[[(2S)-2-[(2-methoxyphenoxy)methyl]morpholin-4-yl]methyl]phenol —— C20H25NO5
2-methoxy-4-[[(2S)-2-[(2-methoxyphenoxy)methyl]morpholin-4-yl]methyl]phenol
—— 2-methoxy-4-[[(2R)-2-[(2-methoxyphenoxy)methyl]morpholin-4-yl]methyl]phenol —— C20H25NO5
2-methoxy-4-[[(2R)-2-[(2-methoxyphenoxy)methyl]morpholin-4-yl]methyl]phenol
—— 2-(2-Bromophenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one —— C16H9BrN2O5
2-(2-Bromophenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one
—— 3-(5-Bromo-2-hydroxy-3-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile —— C17H14BrNO4S
3-(5-Bromo-2-hydroxy-3-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile
—— 1-(2-hydroxy-5-nitrophenyl)-3-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]thiourea —— C12H15N3O5S2
1-(2-hydroxy-5-nitrophenyl)-3-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]thiourea
—— 2-[(2-hydroxy-4-methoxyphenyl)methylidene]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-3-one —— C16H18N2O3
2-[(2-hydroxy-4-methoxyphenyl)methylidene]-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-3-one
—— (5Z)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrClNO3S
(5Z)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— 3,4,5-trihydroxy-N-(2-phenylpropylideneamino)benzamide —— C16H16N2O4
3,4,5-trihydroxy-N-(2-phenylpropylideneamino)benzamide
—— 4-[[5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid —— C19H15ClN2O5S
4-[[5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
—— 2-methoxy-5-[(1R)-2-(pyridin-4-ylmethyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol —— C21H23N3O2
2-methoxy-5-[(1R)-2-(pyridin-4-ylmethyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol
—— 2-methoxy-5-[(1S)-2-(pyridin-4-ylmethyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol —— C21H23N3O2
2-methoxy-5-[(1S)-2-(pyridin-4-ylmethyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol
—— 5-[[(1S)-1-(2,3-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol —— C22H22F2N2O2
5-[[(1S)-1-(2,3-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol
—— 2-methoxy-5-[(1S)-2-(pyridin-3-ylmethyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol —— C21H23N3O2
2-methoxy-5-[(1S)-2-(pyridin-3-ylmethyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol
—— 2-[[(1R)-1-(2,3-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,4-diol —— C21H20F2N2O2
2-[[(1R)-1-(2,3-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,4-diol
—— 2-[(1R)-2-butyl-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol —— C18H24N2O
2-[(1R)-2-butyl-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol
—— 4-hydroxy-N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]benzamide —— C15H14N2O4
4-hydroxy-N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]benzamide
—— 2-methoxy-6-((E)-{[3-(trifluoromethyl)phenyl]imino}methyl)phenol 200630-43-9 C15H12F3NO2
2-methoxy-6-((E)-{[3-(trifluoromethyl)phenyl]imino}methyl)phenol
—— 2-methoxy-6-[[(1R)-1-(2,4,5-trifluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C22H21F3N2O2
2-methoxy-6-[[(1R)-1-(2,4,5-trifluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-methoxy-6-[[(1S)-1-[3-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C23H23F3N2O2
2-methoxy-6-[[(1S)-1-[3-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-one —— C16H19N3O3S
5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-one
—— 3-(4-Hydroxy-2-methylanilino)-1-(4-methoxyphenyl)prop-2-en-1-one —— C17H17NO3
3-(4-Hydroxy-2-methylanilino)-1-(4-methoxyphenyl)prop-2-en-1-one
—— 4-(5-bromo-2-hydroxyphenyl)-6-phenyl-3,4-dihydro-1H-pyrimidine-2-thione —— C16H13BrN2OS
4-(5-bromo-2-hydroxyphenyl)-6-phenyl-3,4-dihydro-1H-pyrimidine-2-thione
—— 2-[[(1S)-1-(3,4-dimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C24H28N2O2
2-[[(1S)-1-(3,4-dimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 2-methoxy-6-[[(1S)-1-(2,4,5-trifluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C22H21F3N2O2
2-methoxy-6-[[(1S)-1-(2,4,5-trifluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-[[(1R)-1-(3,4-dimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C24H28N2O2
2-[[(1R)-1-(3,4-dimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 5-[[(1S)-1-(3,4-dimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol —— C24H28N2O2
5-[[(1S)-1-(3,4-dimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol
—— 3-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2-pyridin-4-yl-1,3-thiazolidin-4-one —— C17H18N2O3S
3-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2-pyridin-4-yl-1,3-thiazolidin-4-one
—— N-[(4-ethoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C16H16N2O5
N-[(4-ethoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— N,N'-bis[(3-hydroxy-4-methoxyphenyl)methylideneamino]hexanediamide —— C22H26N4O6
N,N'-bis[(3-hydroxy-4-methoxyphenyl)methylideneamino]hexanediamide
—— 4-(1,3-Benzothiazol-2-ylsulfanyl)-2,6-dinitrophenol —— C13H7N3O5S2
4-(1,3-Benzothiazol-2-ylsulfanyl)-2,6-dinitrophenol
—— 5-(3-Bromo-4-hydroxy-5-methoxyphenyl)-2,3,4a,8a-tetrachloro-6-ethenyl-5,8-dihydronaphthalene-1,4-dione —— C19H13BrCl4O4
5-(3-Bromo-4-hydroxy-5-methoxyphenyl)-2,3,4a,8a-tetrachloro-6-ethenyl-5,8-dihydronaphthalene-1,4-dione
—— 7-ethenyl-8-(3-fluoro-4-hydroxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19FO3
7-ethenyl-8-(3-fluoro-4-hydroxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— propan-2-yl 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O7S
propan-2-yl 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— [amino(sulfoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;palladium(2+) —— C9H12N3O2PdS+3
[amino(sulfoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;palladium(2+)
—— 3-(4-amino-1,2,5-oxadiazol-3-yl)-N-[1-(3-hydroxyphenyl)ethylideneamino]-5-(piperidin-1-ylmethyl)triazole-4-carboxamide —— C19H23N9O3
3-(4-amino-1,2,5-oxadiazol-3-yl)-N-[1-(3-hydroxyphenyl)ethylideneamino]-5-(piperidin-1-ylmethyl)triazole-4-carboxamide
—— 2-[5-[(2,4-dichlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C18H11Cl2N3O6S
2-[5-[(2,4-dichlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide
—— Methyl 2-[[6-[(2-hydroxy-5-nitrophenyl)methylideneamino]-1,3-benzothiazol-2-yl]sulfanyl]acetate —— C17H13N3O5S2
Methyl 2-[[6-[(2-hydroxy-5-nitrophenyl)methylideneamino]-1,3-benzothiazol-2-yl]sulfanyl]acetate
—— 2-[(4-chlorophenyl)methoxy]-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]benzamide —— C22H19ClN2O4
2-[(4-chlorophenyl)methoxy]-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]benzamide
—— Ethyl 4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C15H17F3N2O5S
Ethyl 4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 6-Ethenyl-5-(2-hydroxy-3-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H26O4
6-Ethenyl-5-(2-hydroxy-3-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— 6-Amino-4-(3-hydroxy-4-methoxyphenyl)-3-thiophen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C18H14N4O3S
6-Amino-4-(3-hydroxy-4-methoxyphenyl)-3-thiophen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 3-[(1S)-1-[(1-methylpyrazol-3-yl)amino]ethyl]phenol —— C12H15N3O
3-[(1S)-1-[(1-methylpyrazol-3-yl)amino]ethyl]phenol
—— 3-(3,4-Dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C27H26N2O3S
3-(3,4-Dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-[(1R)-1-[(1-methylpyrazol-3-yl)amino]ethyl]phenol —— C12H15N3O
4-[(1R)-1-[(1-methylpyrazol-3-yl)amino]ethyl]phenol
—— 3-[[3-(4-Hydroxyphenyl)propanoylamino]carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid —— C18H20N2O5
3-[[3-(4-Hydroxyphenyl)propanoylamino]carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
—— 4-[(Cyclopentylamino)methyl]-2-methoxyphenol —— C13H19NO2
4-[(Cyclopentylamino)methyl]-2-methoxyphenol
—— 4-[(2-Bromo-3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C17H12BrClN2O4
4-[(2-Bromo-3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— methyl (2S)-2-amino-2-(4-hydroxy-3-methoxyphenyl)propanoate —— C11H15NO4
methyl (2S)-2-amino-2-(4-hydroxy-3-methoxyphenyl)propanoate
—— methyl (2R)-2-(4-hydroxy-3-methoxyphenyl)-2-(propylamino)propanoate —— C14H21NO4
methyl (2R)-2-(4-hydroxy-3-methoxyphenyl)-2-(propylamino)propanoate
—— methyl (2S)-2-(4-hydroxy-3-methoxyphenyl)-2-(propylamino)propanoate —— C14H21NO4
methyl (2S)-2-(4-hydroxy-3-methoxyphenyl)-2-(propylamino)propanoate