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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-[(2S,6R)-2-(4-chlorophenyl)-4-(4-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[(2S,6R)-2-(4-chlorophenyl)-4-(4-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-chloro-2-[(2R,6S)-2-(4-chlorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H20Cl2N2O
4-chloro-2-[(2R,6S)-2-(4-chlorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-chloro-2-[(2S,6S)-2-(4-chlorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H20Cl2N2O
4-chloro-2-[(2S,6S)-2-(4-chlorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6S)-4-(4-bromophenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17Br2FN2O
4-bromo-2-[(2S,6S)-4-(4-bromophenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6S)-2-(4-chlorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrClN2O
4-bromo-2-[(2R,6S)-2-(4-chlorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6R)-2-(4-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22Br2N2O
4-bromo-2-[(2R,6R)-2-(4-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-2-(4-bromophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H20Br2N2O
4-bromo-2-[(2S,6R)-2-(4-bromophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6R)-2-(4-bromophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H20Br2N2O
4-bromo-2-[(2R,6R)-2-(4-bromophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-2-(4-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22Br2N2O
4-bromo-2-[(2S,6R)-2-(4-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 1-(4-bromophenyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione —— C19H15BrN2O6
1-(4-bromophenyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
—— 2-(3-chlorophenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one —— C18H16ClN3O2
2-(3-chlorophenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one
—— 1-(2,4-dihydroxyphenyl)-2-(4-phenyl-1H-1,2,4-triazol-5-ylidene)ethanone —— C16H13N3O3
1-(2,4-dihydroxyphenyl)-2-(4-phenyl-1H-1,2,4-triazol-5-ylidene)ethanone
—— 3,4,5-trihydroxy-N'-[1-(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide —— C15H14N2O6
3,4,5-trihydroxy-N'-[1-(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide
—— 3-[7-(2-hydroxy-5-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
3-[7-(2-hydroxy-5-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 2-(2,4-dimethylphenyl)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methylpyrazol-3-one —— C19H18N4O4
2-(2,4-dimethylphenyl)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methylpyrazol-3-one
—— (2R)-2-(3-hydroxy-4-methoxyphenyl)-2-(2-methoxyethylamino)acetic acid —— C12H17NO5
(2R)-2-(3-hydroxy-4-methoxyphenyl)-2-(2-methoxyethylamino)acetic acid
—— N-[3-[2-[(3-hydroxy-4-methoxyphenyl)methylamino]-2-oxoethoxy]phenyl]cyclopropanecarboxamide —— C20H22N2O5
N-[3-[2-[(3-hydroxy-4-methoxyphenyl)methylamino]-2-oxoethoxy]phenyl]cyclopropanecarboxamide
—— N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(2-oxo-3-propylbenzimidazol-1-yl)propanamide —— C21H25N3O4
N-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(2-oxo-3-propylbenzimidazol-1-yl)propanamide
—— 2-[(1S)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,4-diol —— C15H16ClNO2
2-[(1S)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,4-diol
—— 2-[(2S,6R)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H17Cl3N2O
2-[(2S,6R)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 2-[(2R,6S)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H17Cl3N2O
2-[(2R,6S)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 2-[(2R,6R)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H17Cl3N2O
2-[(2R,6R)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 2-[(2S,6S)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H17Cl3N2O
2-[(2S,6S)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 4-[(1R)-1-[(5-methylfuran-2-yl)methylamino]ethyl]phenol —— C14H17NO2
4-[(1R)-1-[(5-methylfuran-2-yl)methylamino]ethyl]phenol
—— 4-[(1S)-1-[(5-methylfuran-2-yl)methylamino]ethyl]phenol —— C14H17NO2
4-[(1S)-1-[(5-methylfuran-2-yl)methylamino]ethyl]phenol
—— 4-hydroxy-N'-(indol-3-ylidenemethyl)-3-methoxybenzohydrazide —— C17H15N3O3
4-hydroxy-N'-(indol-3-ylidenemethyl)-3-methoxybenzohydrazide
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(3-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H14Cl2N2O5S2
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(3-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[[5-[(1R)-1-amino-3-methoxypropyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C13H17N3O3
4-[[5-[(1R)-1-amino-3-methoxypropyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— (2R)-2-[4-(2-methoxyethyl)phenoxy]-N-propan-2-ylbutan-1-amine —— C16H27NO2
(2R)-2-[4-(2-methoxyethyl)phenoxy]-N-propan-2-ylbutan-1-amine
—— (2S)-2-[4-(2-methoxyethyl)phenoxy]-N,3-dimethylbutan-1-amine —— C15H25NO2
(2S)-2-[4-(2-methoxyethyl)phenoxy]-N,3-dimethylbutan-1-amine
—— (2S)-2-[4-(2-methoxyethyl)phenoxy]-N-propan-2-ylbutan-1-amine —— C16H27NO2
(2S)-2-[4-(2-methoxyethyl)phenoxy]-N-propan-2-ylbutan-1-amine
—— (2R)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-methoxyphenyl)sulfanylpropanamide —— C18H21NO4S
(2R)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-methoxyphenyl)sulfanylpropanamide
—— (2S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-methoxyphenyl)sulfanylpropanamide —— C18H21NO4S
(2S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-methoxyphenyl)sulfanylpropanamide
—— (3R)-1-[2-(4-fluorophenyl)acetyl]-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide —— C22H25FN2O4
(3R)-1-[2-(4-fluorophenyl)acetyl]-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide
—— (2S)-2-(4-acetamidophenyl)sulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide —— C19H22N2O4S
(2S)-2-(4-acetamidophenyl)sulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide
—— (2S)-2-benzylsulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide —— C18H21NO3S
(2S)-2-benzylsulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide
—— (2R)-2-benzylsulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide —— C18H21NO3S
(2R)-2-benzylsulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide
—— (3S)-1-[2-(4-fluorophenyl)acetyl]-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide —— C22H25FN2O4
(3S)-1-[2-(4-fluorophenyl)acetyl]-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide
—— (5Z)-5-[(2-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H14Cl2N2O5S2
(5Z)-5-[(2-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-hydroxy-N'-(indol-3-ylidenemethyl)-3,5-dinitrobenzohydrazide —— C16H11N5O6
2-hydroxy-N'-(indol-3-ylidenemethyl)-3,5-dinitrobenzohydrazide
—— 3-[(S)-cyclopentyl-(4-fluorophenyl)methyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C22H27FN2O3
3-[(S)-cyclopentyl-(4-fluorophenyl)methyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2S)-3-methyl-2-phenylbutyl]urea —— C21H28N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2S)-3-methyl-2-phenylbutyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S,3S)-3-methylcyclohexyl]urea —— C17H26N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S,3S)-3-methylcyclohexyl]urea
—— 3-[(1R)-1-(4-tert-butylphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C22H30N2O3
3-[(1R)-1-(4-tert-butylphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R,3R)-3-methylcyclohexyl]urea —— C17H26N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R,3R)-3-methylcyclohexyl]urea
—— 3-[(1S)-1-[4-(difluoromethoxy)phenyl]ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C19H22F2N2O4
3-[(1S)-1-[4-(difluoromethoxy)phenyl]ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(1S)-1-(4-ethoxyphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C20H26N2O4
3-[(1S)-1-(4-ethoxyphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2R)-6-methylheptan-2-yl]urea —— C18H30N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2R)-6-methylheptan-2-yl]urea
—— 3-[(1R)-1-(3,4-dichlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C18H20Cl2N2O3
3-[(1R)-1-(3,4-dichlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(2R)-heptan-2-yl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C17H28N2O3
3-[(2R)-heptan-2-yl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea