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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-[(5-chloro-2-hydroxyanilino)methylidene]-1H-pyrazol-5-one —— C10H8ClN3O2
4-[(5-chloro-2-hydroxyanilino)methylidene]-1H-pyrazol-5-one
—— 1-[2-(2,5-dimethoxyphenyl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C19H24N2O5
1-[2-(2,5-dimethoxyphenyl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 4-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H12ClNO2
4-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-bromo-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]-3,4-dimethylcyclohexa-2,4-dien-1-one —— C17H18BrNO2
2-bromo-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]-3,4-dimethylcyclohexa-2,4-dien-1-one
—— 1-[(3-hydroxyphenyl)methyl]-3-[(1S)-1-(5-methylthiophen-2-yl)ethyl]urea —— C15H18N2O2S
1-[(3-hydroxyphenyl)methyl]-3-[(1S)-1-(5-methylthiophen-2-yl)ethyl]urea
—— 1-[(3-hydroxyphenyl)methyl]-3-[(1R)-1-(5-methylthiophen-2-yl)ethyl]urea —— C15H18N2O2S
1-[(3-hydroxyphenyl)methyl]-3-[(1R)-1-(5-methylthiophen-2-yl)ethyl]urea
—— 1-benzyl-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C22H19N3O3
1-benzyl-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 6-[[[(2-hydroxy-3-methoxyphenyl)-[(5-methoxy-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]methyl]amino]methylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C24H24N2O6
6-[[[(2-hydroxy-3-methoxyphenyl)-[(5-methoxy-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]methyl]amino]methylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— 3-[2-(3-tert-butyl-6-oxocyclohexa-2,4-dien-1-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid —— C16H17N3O7S
3-[2-(3-tert-butyl-6-oxocyclohexa-2,4-dien-1-ylidene)hydrazinyl]-2-hydroxy-5-nitrobenzenesulfonic acid
—— 6-[2-(2-hydroxy-5-nitrophenyl)ethenyl]-4-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]-1H-pyrimidin-2-one —— C20H14N4O7
6-[2-(2-hydroxy-5-nitrophenyl)ethenyl]-4-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]-1H-pyrimidin-2-one
—— N'-[[4-(diethylamino)-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]-3,4,5-trihydroxybenzohydrazide —— C18H21N3O5
N'-[[4-(diethylamino)-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]-3,4,5-trihydroxybenzohydrazide
—— 1-benzyl-5-[(2-hydroxy-5-nitroanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C21H16N4O5
1-benzyl-5-[(2-hydroxy-5-nitroanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— N'-[(3-bromo-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C14H11BrN2O5
N'-[(3-bromo-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— 4-[(3-bromo-2-hydroxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one —— C17H14BrN3O2
4-[(3-bromo-2-hydroxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one
—— 4-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C15H14BrNO3
4-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— N-(but-2-enylideneamino)-3,4,5-trihydroxybenzamide —— C11H12N2O4
N-(but-2-enylideneamino)-3,4,5-trihydroxybenzamide
—— cyclohexyl (7S)-2-benzylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C26H27N5O5S
cyclohexyl (7S)-2-benzylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— 1-[[1-(4-fluorophenyl)-3-methyl-5-oxopyrazol-4-ylidene]methyl]-3-(2-hydroxy-5-nitrophenyl)urea —— C18H14FN5O5
1-[[1-(4-fluorophenyl)-3-methyl-5-oxopyrazol-4-ylidene]methyl]-3-(2-hydroxy-5-nitrophenyl)urea
—— cyclohexyl (7R)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C27H29FN4O4S
cyclohexyl (7R)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— 6-[6-(3,4-dihydroxyphenyl)-2,5-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-ylidene]cyclohexa-2,4-dien-1-one —— C16H12N4O3S
6-[6-(3,4-dihydroxyphenyl)-2,5-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-ylidene]cyclohexa-2,4-dien-1-one
—— 3,4,5-trihydroxy-N'-(pyrrol-2-ylidenemethyl)benzohydrazide —— C12H11N3O4
3,4,5-trihydroxy-N'-(pyrrol-2-ylidenemethyl)benzohydrazide
—— 5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C16H16N2O5S
5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(3-chlorophenyl)-5-methylpyrazol-3-one —— C17H13Cl2N3O2
4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(3-chlorophenyl)-5-methylpyrazol-3-one
—— ethyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C22H20ClN5O5S
ethyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— 4-bromo-2-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H11BrClNO2
4-bromo-2-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— ethyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C22H20ClN5O5S
ethyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— propyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C23H22ClN5O5S
propyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— propyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C24H25ClN4O4S
propyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— propyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C24H25ClN4O4S
propyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— N'-[(3-bromo-5-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxy-5-nitrobenzohydrazide —— C16H14BrN3O6
N'-[(3-bromo-5-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxy-5-nitrobenzohydrazide
—— butyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C25H27ClN4O4S
butyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— (7R)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H20N6O4
(7R)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H24N6O4S
(7R)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 5-[(4-hydroxy-2-methylanilino)methylidene]-1,4-dimethyl-2,6-dioxopyridine-3-carbonitrile —— C16H15N3O3
5-[(4-hydroxy-2-methylanilino)methylidene]-1,4-dimethyl-2,6-dioxopyridine-3-carbonitrile
—— (7R)-2-butylsulfanyl-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C25H28N6O4S
(7R)-2-butylsulfanyl-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 3-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-oxoindolizine-1-carbonitrile —— C17H12N2O3
3-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-oxoindolizine-1-carbonitrile
—— (7R)-2-butylsulfanyl-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C25H28N6O5S
(7R)-2-butylsulfanyl-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 6-[5-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one —— C17H15N3O3
6-[5-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one
—— (7S)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C24H26N6O5S
(7S)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-N-(2,3-dimethylphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H24N6O4S
(7R)-N-(2,3-dimethylphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide —— C20H19N7O5
(7R)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-N-(2,3-dimethylphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H24N6O4S
(7S)-N-(2,3-dimethylphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-butylsulfanyl-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C25H28N6O4S
(7S)-2-butylsulfanyl-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 6-[(2-hydroxy-3-methylanilino)methylidene]-2,4-dinitrocyclohexa-2,4-dien-1-one —— C14H11N3O6
6-[(2-hydroxy-3-methylanilino)methylidene]-2,4-dinitrocyclohexa-2,4-dien-1-one
—— 3-[7-(2-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
3-[7-(2-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2S)-2-methyl-3-pyrazol-1-ylpropyl]urea —— C16H22N4O2
1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2S)-2-methyl-3-pyrazol-1-ylpropyl]urea
—— 1-[(2-hydroxyphenyl)methyl]-3-[(2R)-2-methyl-3-pyrazol-1-ylpropyl]-1-[[(2R)-oxolan-2-yl]methyl]urea —— C20H28N4O3
1-[(2-hydroxyphenyl)methyl]-3-[(2R)-2-methyl-3-pyrazol-1-ylpropyl]-1-[[(2R)-oxolan-2-yl]methyl]urea
—— 2,4-dichloro-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H8Cl2N2O4
2,4-dichloro-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 1-benzyl-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-[[(2R)-oxolan-2-yl]methyl]urea —— C23H30N2O3
1-benzyl-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-[[(2R)-oxolan-2-yl]methyl]urea
—— 4-bromo-6-[(2-hydroxy-4-nitroanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one —— C13H8BrN3O6
4-bromo-6-[(2-hydroxy-4-nitroanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one