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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-[(1R)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,3-diol —— C15H16ClNO2
4-[(1R)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,3-diol
—— 2-[(1R)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,4-diol —— C15H16ClNO2
2-[(1R)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,4-diol
—— 4-[(1S)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,3-diol —— C15H16ClNO2
4-[(1S)-1-[(3-chlorophenyl)methylamino]ethyl]benzene-1,3-diol
—— Copper;[2-[[(2-hydroxybenzoyl)hydrazinylidene]methyl]-6-methoxyphenyl]oxidanium —— C15H15CuN2O4+3
Copper;[2-[[(2-hydroxybenzoyl)hydrazinylidene]methyl]-6-methoxyphenyl]oxidanium
—— N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]-2-[[3-(trifluoromethyl)phenyl]methylsulfonyl]acetamide —— C18H17F3N2O5S
N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]-2-[[3-(trifluoromethyl)phenyl]methylsulfonyl]acetamide
—— 4-[[[(1R,3S)-1-(hydroxymethyl)-3-methylcyclohexyl]amino]methyl]benzene-1,2-diol —— C15H23NO3
4-[[[(1R,3S)-1-(hydroxymethyl)-3-methylcyclohexyl]amino]methyl]benzene-1,2-diol
—— 4-[[[(1S,3S)-1-(hydroxymethyl)-3-methylcyclohexyl]amino]methyl]benzene-1,2-diol —— C15H23NO3
4-[[[(1S,3S)-1-(hydroxymethyl)-3-methylcyclohexyl]amino]methyl]benzene-1,2-diol
—— Methyl 2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H9F3O5
Methyl 2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— 2-Methoxy-5-[[(3,5,6-trichloropyridin-2-yl)hydrazinylidene]methyl]phenol —— C13H10Cl3N3O2
2-Methoxy-5-[[(3,5,6-trichloropyridin-2-yl)hydrazinylidene]methyl]phenol
—— 2-[(1S)-1-[(5-methylfuran-2-yl)methylamino]ethyl]phenol —— C14H17NO2
2-[(1S)-1-[(5-methylfuran-2-yl)methylamino]ethyl]phenol
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(3-hydroxyphenyl)methylideneamino]-5-[(4-methylpiperidin-1-yl)methyl]triazole-4-carboxamide —— C19H23N9O3
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(3-hydroxyphenyl)methylideneamino]-5-[(4-methylpiperidin-1-yl)methyl]triazole-4-carboxamide
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(3-hydroxyphenyl)methylideneamino]-5-[(4-methylpiperidin-1-ium-1-yl)methyl]triazole-4-carboxamide —— C19H24N9O3+
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(3-hydroxyphenyl)methylideneamino]-5-[(4-methylpiperidin-1-ium-1-yl)methyl]triazole-4-carboxamide
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(2-hydroxyphenyl)methylideneamino]-5-[(4-methylpiperidin-1-yl)methyl]triazole-4-carboxamide —— C19H23N9O3
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(2-hydroxyphenyl)methylideneamino]-5-[(4-methylpiperidin-1-yl)methyl]triazole-4-carboxamide
—— 2-(4-tert-butylphenoxy)-N-(2-hydroxy-4-methoxyphenyl)acetamide —— C19H23NO4
2-(4-tert-butylphenoxy)-N-(2-hydroxy-4-methoxyphenyl)acetamide
—— 2-(2-Chlorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13ClN2O3S
2-(2-Chlorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-(Furan-2-ylmethylidene)-2-(3-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C17H14N2O3S
5-(Furan-2-ylmethylidene)-2-(3-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 2-(2,4,6-Trimethylpyridin-1-ium-1-yl)phenol —— C14H16NO+
2-(2,4,6-Trimethylpyridin-1-ium-1-yl)phenol
—— N'-[(E)-(2-chlorophenyl)methylidene]-2-hydroxy-3,5-dinitrobenzohydrazide —— C14H9ClN4O6
N'-[(E)-(2-chlorophenyl)methylidene]-2-hydroxy-3,5-dinitrobenzohydrazide
—— Magnesium;4-nitrophenolate;pyridin-1-ium —— C22H20MgN4O6+2
Magnesium;4-nitrophenolate;pyridin-1-ium
—— 2-(3-Hydroxyphenyl)imino-5-(2-methyl-3-phenylprop-2-enylidene)-3-prop-2-enyl-1,3-thiazolidin-4-one —— C22H20N2O2S
2-(3-Hydroxyphenyl)imino-5-(2-methyl-3-phenylprop-2-enylidene)-3-prop-2-enyl-1,3-thiazolidin-4-one
—— N-[(3-fluorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H11FN2O4
N-[(3-fluorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 5-Benzylidene-2-(3-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C19H16N2O2S
5-Benzylidene-2-(3-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 2-[2-(3-Hydroxyphenyl)imino-4-oxo-3-prop-2-enyl-1,3-thiazolidin-5-yl]acetic acid —— C14H14N2O4S
2-[2-(3-Hydroxyphenyl)imino-4-oxo-3-prop-2-enyl-1,3-thiazolidin-5-yl]acetic acid
—— 2-hydroxy-N-[(4-methoxyphenyl)methylideneamino]-5-nitrobenzamide —— C15H13N3O5
2-hydroxy-N-[(4-methoxyphenyl)methylideneamino]-5-nitrobenzamide
—— 5-[(2-Hydroxy-5-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C10H7N3O4S
5-[(2-Hydroxy-5-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methyl-3-nitrobenzamide —— C16H15N3O5
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methyl-3-nitrobenzamide
—— Methyl 4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(1-phenylethyl)pyrrole-3-carboxylate —— C22H21NO4
Methyl 4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(1-phenylethyl)pyrrole-3-carboxylate
—— 3-Cyclohexyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-methyl-2-sulfanylideneimidazolidin-4-one —— C19H24N2O4S
3-Cyclohexyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-methyl-2-sulfanylideneimidazolidin-4-one
—— 2-[6-(4-Chlorophenyl)-2-(3-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C23H21ClFN2O2+
2-[6-(4-Chlorophenyl)-2-(3-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— 2-[6-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C23H20Cl3N2O2+
2-[6-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— 2-[6-(4-Chlorophenyl)-2-(3-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol —— C23H20ClFN2O2
2-[6-(4-Chlorophenyl)-2-(3-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol
—— 2-[6-(4-Chlorophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol —— C23H20ClFN2O2
2-[6-(4-Chlorophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol
—— 2-[6-(4-Chlorophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C23H21ClFN2O2+
2-[6-(4-Chlorophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— 2-[6-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol —— C23H19Cl3N2O2
2-[6-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol
—— 3-(3,4-Dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2,3,4-trihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C26H24N2O4S
3-(3,4-Dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2,3,4-trihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N-[(2S)-2-[4-(2-methoxyethyl)phenoxy]propyl]-2-methylpropan-1-amine —— C16H27NO2
N-[(2S)-2-[4-(2-methoxyethyl)phenoxy]propyl]-2-methylpropan-1-amine
—— 3-Benzyl-2-benzylimino-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C25H21BrN2O3S
3-Benzyl-2-benzylimino-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2S)-2-[4-(2-methoxyethyl)phenoxy]-N-propylpropan-1-amine —— C15H25NO2
(2S)-2-[4-(2-methoxyethyl)phenoxy]-N-propylpropan-1-amine
—— [3-(2-hydroxy-4-methoxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](4-methylphenyl)methanone —— C24H22N2O3
[3-(2-hydroxy-4-methoxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl](4-methylphenyl)methanone
—— ethyl 5-(2,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23N3O8S
ethyl 5-(2,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S)-2-(3-tert-butylphenoxy)-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide —— C21H27NO4
(2S)-2-(3-tert-butylphenoxy)-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide
—— (2R)-2-(3-tert-butylphenoxy)-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide —— C21H27NO4
(2R)-2-(3-tert-butylphenoxy)-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide
—— (2R)-2-(4-acetamidophenyl)sulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide —— C19H22N2O4S
(2R)-2-(4-acetamidophenyl)sulfanyl-N-[(4-hydroxy-3-methoxyphenyl)methyl]propanamide
—— 3-(2-Hydroxyphenyl)-2,3,3a,6-tetrahydropyrazolo[3,4-d][1,3]thiazol-5-one —— C10H9N3O2S
3-(2-Hydroxyphenyl)-2,3,3a,6-tetrahydropyrazolo[3,4-d][1,3]thiazol-5-one
—— ethyl 2-anilino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C24H23NO5S
ethyl 2-anilino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19ClO3
8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3-[(1S)-1-(4-tert-butylphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C22H30N2O3
3-[(1S)-1-(4-tert-butylphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S,3R)-3-methylcyclohexyl]urea —— C17H26N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S,3R)-3-methylcyclohexyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2R)-3-methyl-2-phenylbutyl]urea —— C21H28N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2R)-3-methyl-2-phenylbutyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S)-1-(4-methylphenyl)ethyl]urea —— C19H24N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S)-1-(4-methylphenyl)ethyl]urea