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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-hydroxy-3-methoxyphenyl)methyl-[(1S)-1-phenylethyl]azanium —— C16H20NO2+
(4-hydroxy-3-methoxyphenyl)methyl-[(1S)-1-phenylethyl]azanium
—— 2,6-dimethoxy-4-[[[(1S)-1-phenylethyl]amino]methyl]phenol —— C17H21NO3
2,6-dimethoxy-4-[[[(1S)-1-phenylethyl]amino]methyl]phenol
—— [(3R)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone —— C18H13N3O4S2
[(3R)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone
—— furan-2-yl-[(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]methanone —— C18H13N3O5S
furan-2-yl-[(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]methanone
—— [(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone —— C18H13N3O4S2
[(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone
—— (4-Hydroxy-3-methoxyphenyl)methyl-(pyridin-3-ylmethyl)azanium —— C14H17N2O2+
(4-Hydroxy-3-methoxyphenyl)methyl-(pyridin-3-ylmethyl)azanium
—— (2S)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2S)-oxiran-2-yl]methoxy]propan-2-ol —— C15H22O5
(2S)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2S)-oxiran-2-yl]methoxy]propan-2-ol
—— (2R)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2S)-oxiran-2-yl]methoxy]propan-2-ol —— C15H22O5
(2R)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2S)-oxiran-2-yl]methoxy]propan-2-ol
—— (2R)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2R)-oxiran-2-yl]methoxy]propan-2-ol —— C15H22O5
(2R)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2R)-oxiran-2-yl]methoxy]propan-2-ol
—— (3aR)-7-hydroxy-3a-methyl-2,3-dihydropyrrolo[1,2-a][3,1]benzoxazine-1,5-dione —— C12H11NO4
(3aR)-7-hydroxy-3a-methyl-2,3-dihydropyrrolo[1,2-a][3,1]benzoxazine-1,5-dione
—— (2S)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2R)-oxiran-2-yl]methoxy]propan-2-ol —— C15H22O5
(2S)-1-[4-(2-methoxyethyl)phenoxy]-3-[[(2R)-oxiran-2-yl]methoxy]propan-2-ol
—— (3aS)-7-hydroxy-3a-methyl-2,3-dihydropyrrolo[1,2-a][3,1]benzoxazine-1,5-dione —— C12H11NO4
(3aS)-7-hydroxy-3a-methyl-2,3-dihydropyrrolo[1,2-a][3,1]benzoxazine-1,5-dione
—— (2R)-2-(2-hydroxy-3-methoxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile —— C14H19N2O2+
(2R)-2-(2-hydroxy-3-methoxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile
—— ethyl (5R)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (5R)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4S)-3-(1-adamantyl)-6-amino-4-(4-hydroxy-3-methoxyphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C24H26N4O3
(4S)-3-(1-adamantyl)-6-amino-4-(4-hydroxy-3-methoxyphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— (4S)-6-amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-thiophen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C19H16N4O4S
(4S)-6-amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-thiophen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 2-methoxyethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19BrN2O6
2-methoxyethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methylsulfanylethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19ClN2O5S
2-methylsulfanylethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— prop-2-enyl (4R)-6-(2-amino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-3,4-dihydropyridine-3-carboxylate —— C20H21N3O5S
prop-2-enyl (4R)-6-(2-amino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-3,4-dihydropyridine-3-carboxylate
—— 5-[[(2S,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]-2-[[(2S,6S)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]benzene-1,4-diol —— C20H34N2O4+2
5-[[(2S,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]-2-[[(2S,6S)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]benzene-1,4-diol
—— (5Z)-5-(5-bromo-3-chloro-2-hydroxybenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrClNO3S
(5Z)-5-(5-bromo-3-chloro-2-hydroxybenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione
—— 2-[2-(4-Hydroxyphenyl)ethyliminomethyl]-5,5-dimethylcyclohexane-1,3-dione —— C17H21NO3
2-[2-(4-Hydroxyphenyl)ethyliminomethyl]-5,5-dimethylcyclohexane-1,3-dione
—— (2Z)-2-[(2-hydroxy-4-nitroanilino)methylidene]-1-benzothiophen-3-one —— C15H10N2O4S
(2Z)-2-[(2-hydroxy-4-nitroanilino)methylidene]-1-benzothiophen-3-one
—— 2-propan-2-yloxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H24N2O6
2-propan-2-yloxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-propan-2-yloxyethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23BrN2O6
2-propan-2-yloxyethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methylsulfanylethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H20N2O5S
2-methylsulfanylethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-cyanoethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H17N3O5
2-cyanoethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (2R)-3-benzyl-2-(3-hydroxyphenyl)-1,3-thiazolidin-4-one —— C16H15NO2S
(2R)-3-benzyl-2-(3-hydroxyphenyl)-1,3-thiazolidin-4-one
—— (4R,4aR,5R,8aR)-4-(4-hydroxy-3-methoxyphenyl)-1,3,5,6,8-pentamethyl-4,4a,5,8a-tetrahydropyrimido[4,5-d]pyrimidine-2,7-dione —— C18H26N4O4
(4R,4aR,5R,8aR)-4-(4-hydroxy-3-methoxyphenyl)-1,3,5,6,8-pentamethyl-4,4a,5,8a-tetrahydropyrimido[4,5-d]pyrimidine-2,7-dione
—— 2-(2-Hydroxy-3-methoxyphenyl)-5,7-di(propan-2-yl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C21H34N2O3+2
2-(2-Hydroxy-3-methoxyphenyl)-5,7-di(propan-2-yl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— 2-[(3R)-3-cyclohexylthian-1-ium-1-yl]benzene-1,4-diol —— C17H25O2S+
2-[(3R)-3-cyclohexylthian-1-ium-1-yl]benzene-1,4-diol
—— prop-2-enyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H18N2O5
prop-2-enyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-phenoxyethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H21BrN2O6
2-phenoxyethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— butyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H21BrN2O5
butyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— [(1R,2S)-2-methylcyclopentyl] (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C19H24N2O5
[(1R,2S)-2-methylcyclopentyl] (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— cycloheptyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C19H23N3O6
cycloheptyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-phenoxyethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H22N2O6
2-phenoxyethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 4-[(1S)-2-[(5,6-dimethylpyrimidin-4-yl)amino]-1-hydroxyethyl]benzene-1,2-diol —— C14H17N3O3
4-[(1S)-2-[(5,6-dimethylpyrimidin-4-yl)amino]-1-hydroxyethyl]benzene-1,2-diol
—— 4-[(1R)-2-[(5,6-dimethylpyrimidin-4-yl)amino]-1-hydroxyethyl]benzene-1,2-diol —— C14H17N3O3
4-[(1R)-2-[(5,6-dimethylpyrimidin-4-yl)amino]-1-hydroxyethyl]benzene-1,2-diol
—— 2-[(2R,4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl]phenol —— C17H19NO2
2-[(2R,4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl]phenol
—— 2-[(1R,2R,5R,6S,9R)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C18H24O3
2-[(1R,2R,5R,6S,9R)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— 4-[(1R,2S,5R,6R,9R)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]-2-methoxyphenol —— C19H26O4
4-[(1R,2S,5R,6R,9R)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]-2-methoxyphenol
—— [4-[[Bis(prop-2-enyl)azaniumyl]methyl]-2,5-dihydroxyphenyl]methyl-bis(prop-2-enyl)azanium —— C20H30N2O2+2
[4-[[Bis(prop-2-enyl)azaniumyl]methyl]-2,5-dihydroxyphenyl]methyl-bis(prop-2-enyl)azanium
—— 3-[(7R)-7-(4-hydroxy-3-nitrophenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C17H16N2O6S
3-[(7R)-7-(4-hydroxy-3-nitrophenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 2-ethylsulfanylethyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H24N2O6S
2-ethylsulfanylethyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-ethoxyethyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H24N2O7
2-ethoxyethyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-propoxyethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23ClN2O6
2-propoxyethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (4R,5R,6S)-4-hydroxy-6-(4-hydroxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C14H15F3N2O4S
ethyl (4R,5R,6S)-4-hydroxy-6-(4-hydroxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 2-ethylsulfanylethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H22N2O5S
2-ethylsulfanylethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methoxyethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17N3O7
2-methoxyethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate