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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
—— (2R)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile —— C16H21N3O3
(2R)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile
—— (2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile —— C16H21N3O3
(2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile
—— 3-(5-Chloro-1-methylimidazol-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one —— C14H13ClN2O3
3-(5-Chloro-1-methylimidazol-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
—— (2R)-2-cyano-N-cyclohexyl-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C17H22N2O3
(2R)-2-cyano-N-cyclohexyl-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— [(3-Methoxy-2-oxoniophenyl)methylideneamino]-[oxoniumylidene(pyridin-4-yl)methyl]azanide;nickel(2+) —— C14H14N3NiO3+3
[(3-Methoxy-2-oxoniophenyl)methylideneamino]-[oxoniumylidene(pyridin-4-yl)methyl]azanide;nickel(2+)
—— 5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-2-phenylimino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C19H14Br2N2O2S
5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-2-phenylimino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 5-[(4-Hydroxy-3-nitrophenyl)methylidene]-3-[(2-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H11N3O7S
5-[(4-Hydroxy-3-nitrophenyl)methylidene]-3-[(2-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— methyl 4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate —— C14H13NO4
methyl 4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate
—— 4-[(2S,5R)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C17H19NO4
4-[(2S,5R)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 4-[(2R,5R)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C17H19NO4
4-[(2R,5R)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 4-[(2-Bromo-4-methylphenyl)iminomethyl]-2,6-dimethylphenol —— C16H16BrNO
4-[(2-Bromo-4-methylphenyl)iminomethyl]-2,6-dimethylphenol
—— 5-[(2R,5R)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C17H19NO4
5-[(2R,5R)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— propan-2-yl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O5S
propan-2-yl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(2,4-dihydroxyphenyl)methylideneamino]-2-(4-phenylmethoxyphenoxy)acetamide —— C22H20N2O5
N-[(2,4-dihydroxyphenyl)methylideneamino]-2-(4-phenylmethoxyphenoxy)acetamide
—— 7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O4
7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 1-[(5-Bromo-2-hydroxyphenyl)methylideneamino]-3-(3-chlorophenyl)thiourea —— C14H11BrClN3OS
1-[(5-Bromo-2-hydroxyphenyl)methylideneamino]-3-(3-chlorophenyl)thiourea
—— 2,3,4a,8a-Tetrachloro-6-ethenyl-5-(2-hydroxy-3-methoxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C19H14Cl4O4
2,3,4a,8a-Tetrachloro-6-ethenyl-5-(2-hydroxy-3-methoxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-phenylpropanamide —— C17H16N2O3
(2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-phenylpropanamide
—— 4-bromo-2-nitro-6-(5-phenyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)phenol —— C17H12BrN5O3
4-bromo-2-nitro-6-(5-phenyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)phenol
—— 3-(4-Hydroxyphenyl)-5-[(1-methylpyrrol-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H12N2O2S2
3-(4-Hydroxyphenyl)-5-[(1-methylpyrrol-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2,4-dibromophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H14Br2N2O4
2-(2,4-dibromophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (2R)-N-benzyl-2-cyano-3-(3-hydroxyphenyl)-N-methylpropanamide —— C18H18N2O2
(2R)-N-benzyl-2-cyano-3-(3-hydroxyphenyl)-N-methylpropanamide
—— 2-(4-bromophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H15BrN2O4
2-(4-bromophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 5-[(2S,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C16H23NO4
5-[(2S,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— methyl 3-[2-(3-hydroxy-4-methoxyphenyl)-1,3-thiazol-4-yl]propanoate —— C14H15NO4S
methyl 3-[2-(3-hydroxy-4-methoxyphenyl)-1,3-thiazol-4-yl]propanoate
—— 4-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C16H23NO4
4-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— (3R)-1-[3-(3-hydroxy-4-methoxyphenyl)propyl]-5-oxopyrrolidine-3-carboxylic acid —— C15H19NO5
(3R)-1-[3-(3-hydroxy-4-methoxyphenyl)propyl]-5-oxopyrrolidine-3-carboxylic acid
—— (3S)-1-[3-(3-hydroxy-4-methoxyphenyl)propyl]-5-oxopyrrolidine-3-carboxylic acid —— C15H19NO5
(3S)-1-[3-(3-hydroxy-4-methoxyphenyl)propyl]-5-oxopyrrolidine-3-carboxylic acid
—— 5-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C16H23NO4
5-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— (3R)-1-[3-(4-hydroxy-3-methoxyphenyl)propyl]-5-oxopyrrolidine-3-carboxylic acid —— C15H19NO5
(3R)-1-[3-(4-hydroxy-3-methoxyphenyl)propyl]-5-oxopyrrolidine-3-carboxylic acid
—— 4-[(2S,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C16H23NO4
4-[(2S,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 4-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-3-methoxybenzamide —— C18H18N2O6S
4-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-3-methoxybenzamide
—— tert-butyl N-[(S)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]-N-methylcarbamate —— C15H20N2O4
tert-butyl N-[(S)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]-N-methylcarbamate
—— 4-hydroxy-3-methoxy-N-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide —— C21H18N2O4S2
4-hydroxy-3-methoxy-N-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide
—— tert-butyl N-[(R)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]-N-methylcarbamate —— C15H20N2O4
tert-butyl N-[(R)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]-N-methylcarbamate
—— 5-[(2-Bromo-3-hydroxy-4-methoxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C17H12BrNO4S
5-[(2-Bromo-3-hydroxy-4-methoxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— N-[1-(3-hydroxyphenyl)ethylideneamino]acetamide —— C10H12N2O2
N-[1-(3-hydroxyphenyl)ethylideneamino]acetamide
—— 4-[(1-Pyrrolidin-1-ium-1-ylcyclohexyl)methyl]phenol —— C17H26NO+
4-[(1-Pyrrolidin-1-ium-1-ylcyclohexyl)methyl]phenol
—— Ditert-butyl 4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate —— C24H33NO6
Ditert-butyl 4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— (2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile —— C15H18N2O4
(2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile
—— (2R)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile —— C15H18N2O4
(2R)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile
—— (2S)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile —— C15H18N2O4
(2S)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile
—— (2S)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile —— C15H18N2O4
(2S)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile
—— N-[(5-chlorothiophen-2-yl)methylideneamino]-3,4,5-trihydroxybenzamide —— C12H9ClN2O4S
N-[(5-chlorothiophen-2-yl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 2-(3-chlorophenoxy)-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C15H12ClN3O5
2-(3-chlorophenoxy)-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— Diethyl 2-[5-[(4-hydroxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]propanedioate —— C23H21NO6S
Diethyl 2-[5-[(4-hydroxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]propanedioate
—— (2R)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-oxo-3-piperidin-1-ylpropanenitrile —— C16H20N2O3
(2R)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-oxo-3-piperidin-1-ylpropanenitrile
—— (2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-oxo-3-piperidin-1-ylpropanenitrile —— C16H20N2O3
(2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-oxo-3-piperidin-1-ylpropanenitrile
—— (2S)-2-cyano-N-cyclopentyl-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C16H20N2O3
(2S)-2-cyano-N-cyclopentyl-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— 6-Ethenyl-5-(2-hydroxy-5-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H26O4
6-Ethenyl-5-(2-hydroxy-5-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione