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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
—— 3-[(R)-cyclopentyl-(4-fluorophenyl)methyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C22H27FN2O3
3-[(R)-cyclopentyl-(4-fluorophenyl)methyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R)-1-(4-methylphenyl)ethyl]urea —— C19H24N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R)-1-(4-methylphenyl)ethyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R,3S)-3-methylcyclohexyl]urea —— C17H26N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R,3S)-3-methylcyclohexyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R)-1-[4-(trifluoromethyl)phenyl]ethyl]urea —— C19H21F3N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R)-1-[4-(trifluoromethyl)phenyl]ethyl]urea
—— 3-[(1R)-1-(4-ethoxyphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C20H26N2O4
3-[(1R)-1-(4-ethoxyphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(4S)-6-chloro-3,4-dihydro-2H-thiochromen-4-yl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C19H21ClN2O3S
3-[(4S)-6-chloro-3,4-dihydro-2H-thiochromen-4-yl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— N-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]tricyclo[4.3.1.13,8]undecane-1-carboxamide —— C19H22BrN3O4
N-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]tricyclo[4.3.1.13,8]undecane-1-carboxamide
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[3-[(1R)-1-phenylethoxy]propyl]urea —— C21H28N2O4
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[3-[(1R)-1-phenylethoxy]propyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2S)-6-methylheptan-2-yl]urea —— C18H30N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(2S)-6-methylheptan-2-yl]urea
—— 2-[Benzotriazol-1-yl-(2,4-dimethylanilino)methyl]-4-nitrophenol —— C21H19N5O3
2-[Benzotriazol-1-yl-(2,4-dimethylanilino)methyl]-4-nitrophenol
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S)-1-[3-(trifluoromethyl)phenyl]ethyl]urea —— C19H21F3N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1S)-1-[3-(trifluoromethyl)phenyl]ethyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R,2S)-2-methylcyclohexyl]urea —— C17H26N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[(1R,2S)-2-methylcyclohexyl]urea
—— 3-[(1R)-1-(3-chlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C18H21ClN2O3
3-[(1R)-1-(3-chlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(1S)-1-(3-fluoro-4-methoxyphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C19H23FN2O4
3-[(1S)-1-(3-fluoro-4-methoxyphenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(1S)-1-(2-chlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C18H21ClN2O3
3-[(1S)-1-(2-chlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(1S)-1-(2-bromophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C18H21BrN2O3
3-[(1S)-1-(2-bromophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— 3-[(1S)-1-(3-chlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea —— C18H21ClN2O3
3-[(1S)-1-(3-chlorophenyl)ethyl]-1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methylurea
—— methyl 2-[(2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H18N2O4S
methyl 2-[(2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-Benzyl-4-(4-hydroxyphenyl)-6-imino-3-methyl-1,4,5,6-tetrahydropyrano[2,3-c]pyrazole-5-carbonitrile —— C21H18N4O2
1-Benzyl-4-(4-hydroxyphenyl)-6-imino-3-methyl-1,4,5,6-tetrahydropyrano[2,3-c]pyrazole-5-carbonitrile
—— propan-2-yl 7-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C17H19BrN4O4
propan-2-yl 7-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— 1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]-3-(1,3-thiazol-2-yl)urea —— C16H19N3O3S
1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]-3-(1,3-thiazol-2-yl)urea
—— 1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]-3-(1,3-thiazol-2-yl)urea —— C16H19N3O3S
1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]-3-(1,3-thiazol-2-yl)urea
—— 3-Benzyl-2-(3-hydroxyphenyl)-1,3-thiazolidin-4-one —— C16H15NO2S
3-Benzyl-2-(3-hydroxyphenyl)-1,3-thiazolidin-4-one
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-[6-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C28H28N2O6S4
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-[6-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-[(4-Hydroxy-3,5-dimethylphenyl)methylamino]-5,6-dimethylpyridazine-4-carbonitrile —— C16H18N4O
3-[(4-Hydroxy-3,5-dimethylphenyl)methylamino]-5,6-dimethylpyridazine-4-carbonitrile
—— 2-(3-Hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-1,2,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4-ol —— C22H28N2O3S
2-(3-Hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-1,2,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4-ol
—— 5-(2-Hydroxy-5-nitrophenyl)furan-2-carbaldehyde —— C11H7NO5
5-(2-Hydroxy-5-nitrophenyl)furan-2-carbaldehyde
—— 3-[2-(4-Hydroxyphenyl)ethyl]-2-pyridin-4-yl-1,3-thiazolidin-4-one —— C16H16N2O2S
3-[2-(4-Hydroxyphenyl)ethyl]-2-pyridin-4-yl-1,3-thiazolidin-4-one
—— 2-[(1R)-1-[[(1R)-1-cyclohexylpropyl]amino]ethyl]phenol —— C17H27NO
2-[(1R)-1-[[(1R)-1-cyclohexylpropyl]amino]ethyl]phenol
—— 2-[(1S)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]phenol —— C16H25NO
2-[(1S)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]phenol
—— 2-[(1R)-1-[[(1R)-1-cyclohexylethyl]amino]ethyl]phenol —— C16H25NO
2-[(1R)-1-[[(1R)-1-cyclohexylethyl]amino]ethyl]phenol
—— 2-[(1R)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]phenol —— C16H25NO
2-[(1R)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]phenol
—— N-[1-(2,4-dichlorophenyl)propylideneamino]-3,4,5-trihydroxybenzamide —— C16H14Cl2N2O4
N-[1-(2,4-dichlorophenyl)propylideneamino]-3,4,5-trihydroxybenzamide
—— 2-[(1S)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]-4-methylphenol —— C17H27NO
2-[(1S)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]-4-methylphenol
—— 2-[(1S)-1-[[(1R)-1-cyclohexylethyl]amino]ethyl]phenol —— C16H25NO
2-[(1S)-1-[[(1R)-1-cyclohexylethyl]amino]ethyl]phenol
—— 2-[(1S)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]benzene-1,4-diol —— C16H25NO2
2-[(1S)-1-[[(1S)-1-cyclohexylethyl]amino]ethyl]benzene-1,4-diol
—— 2-[(1S)-1-[[(1R)-1-cyclohexylethyl]amino]ethyl]-4-methylphenol —— C17H27NO
2-[(1S)-1-[[(1R)-1-cyclohexylethyl]amino]ethyl]-4-methylphenol
—— 2-[[5-[(3,4-Dihydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile —— C18H12N2O4S
2-[[5-[(3,4-Dihydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile
—— 2-[2,6-Bis(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-bromophenol —— C22H18BrCl2N2O+
2-[2,6-Bis(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-bromophenol
—— 2-[6-(4-Chlorophenyl)-2-(3-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[6-(4-Chlorophenyl)-2-(3-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol
—— 4-Bromo-2-[6-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17BrClFN2O
4-Bromo-2-[6-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Bromo-2-[6-(4-chlorophenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C19H21BrClN2O+
4-Bromo-2-[6-(4-chlorophenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Bromo-2-[6-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18BrClFN2O+
4-Bromo-2-[6-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 2-[6-(4-Chlorophenyl)-2-(3-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C24H24ClN2O3+
2-[6-(4-Chlorophenyl)-2-(3-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— 4-Bromo-2-[6-(4-chlorophenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C19H20BrClN2O
4-Bromo-2-[6-(4-chlorophenyl)-2-propan-2-yl-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 5-methoxy-2-[[[(1R,2S)-2-methylcyclopropyl]amino]methyl]phenol —— C12H17NO2
5-methoxy-2-[[[(1R,2S)-2-methylcyclopropyl]amino]methyl]phenol
—— 3-[[[(1S,2R)-2-methylcyclopropyl]amino]methyl]benzene-1,2-diol —— C11H15NO2
3-[[[(1S,2R)-2-methylcyclopropyl]amino]methyl]benzene-1,2-diol
—— 3-[[[(1R,2S)-2-methylcyclopropyl]amino]methyl]benzene-1,2-diol —— C11H15NO2
3-[[[(1R,2S)-2-methylcyclopropyl]amino]methyl]benzene-1,2-diol
—— 4-methoxy-2-[[[(1S,2R)-2-methylcyclopropyl]amino]methyl]phenol —— C12H17NO2
4-methoxy-2-[[[(1S,2R)-2-methylcyclopropyl]amino]methyl]phenol
—— 4-[[[(1R,2S)-2-methylcyclopropyl]amino]methyl]benzene-1,2-diol —— C11H15NO2
4-[[[(1R,2S)-2-methylcyclopropyl]amino]methyl]benzene-1,2-diol