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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
—— 5-(furan-2-yl)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thieno[2,3-d]pyrimidin-4-one —— C18H13N3O4S
5-(furan-2-yl)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thieno[2,3-d]pyrimidin-4-one
—— 4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1,2,4-triazolidine-3,5-dithione —— C9H8N4OS2
4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1,2,4-triazolidine-3,5-dithione
—— 3-O-ethyl 4-O-[2-(4-methoxyphenyl)ethyl] (4S)-2,6-dimethyl-3,4-dihydropyridine-3,4-dicarboxylate —— C20H25NO5
3-O-ethyl 4-O-[2-(4-methoxyphenyl)ethyl] (4S)-2,6-dimethyl-3,4-dihydropyridine-3,4-dicarboxylate
—— 2-[(4-Benzylsulfonylpiperazin-1-yl)methyl]-4-methoxy-6-prop-2-enylphenol —— C22H28N2O4S
2-[(4-Benzylsulfonylpiperazin-1-yl)methyl]-4-methoxy-6-prop-2-enylphenol
—— methyl (3S)-3-(3,4-dihydroxy-5-methoxyphenyl)-3-(4-hydroxy-6-methyl-2-oxo-1H-pyridin-3-yl)propanoate —— C17H19NO7
methyl (3S)-3-(3,4-dihydroxy-5-methoxyphenyl)-3-(4-hydroxy-6-methyl-2-oxo-1H-pyridin-3-yl)propanoate
—— methyl (3R)-3-(3,4-dihydroxy-5-methoxyphenyl)-3-(4-hydroxy-6-methyl-2-oxo-1H-pyridin-3-yl)propanoate —— C17H19NO7
methyl (3R)-3-(3,4-dihydroxy-5-methoxyphenyl)-3-(4-hydroxy-6-methyl-2-oxo-1H-pyridin-3-yl)propanoate
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[3-(trifluoromethyl)phenyl]thiourea —— C16H14F3N3O2S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[3-(trifluoromethyl)phenyl]thiourea
—— 1-[(3S)-3-(4-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C17H15BrN2O2
1-[(3S)-3-(4-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— 1-[(3R)-3-(4-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C17H15BrN2O2
1-[(3R)-3-(4-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— 1-[(3R)-5-(furan-2-yl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O3
1-[(3R)-5-(furan-2-yl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— 1-[(3S)-5-(furan-2-yl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O3
1-[(3S)-5-(furan-2-yl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— (1R,2R)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide —— C19H20FNO3
(1R,2R)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide
—— (2S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-N-methyl-2-phenyl-2-thiomorpholin-4-ylacetamide —— C21H26N2O3S
(2S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-N-methyl-2-phenyl-2-thiomorpholin-4-ylacetamide
—— (1S,2S)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide —— C19H20FNO3
(1S,2S)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide
—— (2R)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-N-methyl-2-phenyl-2-thiomorpholin-4-ylacetamide —— C21H26N2O3S
(2R)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-N-methyl-2-phenyl-2-thiomorpholin-4-ylacetamide
—— (1R,2S)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide —— C19H20FNO3
(1R,2S)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide
—— (1S,2R)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide —— C19H20FNO3
(1S,2R)-2-(2-fluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methylcyclopropane-1-carboxamide
—— 1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2S)-3-methyl-2-morpholin-4-ylbutyl]urea —— C18H29N3O3
1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2S)-3-methyl-2-morpholin-4-ylbutyl]urea
—— 1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2R)-3-methyl-2-morpholin-4-ylbutyl]urea —— C18H29N3O3
1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2R)-3-methyl-2-morpholin-4-ylbutyl]urea
—— (5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C17H20N2O2S
(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
—— (5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C16H17BrN2O3S
(5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
—— 5-[(Z)-[3-(3,5-dimethylpyrazol-1-yl)-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol —— C15H16N6O2
5-[(Z)-[3-(3,5-dimethylpyrazol-1-yl)-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-fluorophenoxy)acetamide —— C16H14BrFN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-fluorophenoxy)acetamide
—— (2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl-[(4-methoxyphenyl)methyl]-methylazanium —— C20H26NO3+
(2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl-[(4-methoxyphenyl)methyl]-methylazanium
—— 1-[2-(dimethylamino)ethyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methylpropyl)urea —— C19H33N3O2
1-[2-(dimethylamino)ethyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methylpropyl)urea
—— (3R)-N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide —— C17H15BrN2O5
(3R)-N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
—— 1-benzyl-1-(2-hydroxyethyl)-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C20H26N2O3
1-benzyl-1-(2-hydroxyethyl)-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1,4-thiazepane-4-carboxamide —— C16H24N2O2S
N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1,4-thiazepane-4-carboxamide
—— 1-benzyl-1-(2-hydroxyethyl)-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C20H26N2O3
1-benzyl-1-(2-hydroxyethyl)-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 1-(furan-2-ylmethyl)-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methoxyethyl)urea —— C19H26N2O4
1-(furan-2-ylmethyl)-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methoxyethyl)urea
—— 1-(furan-2-ylmethyl)-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methoxyethyl)urea —— C19H26N2O4
1-(furan-2-ylmethyl)-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methoxyethyl)urea
—— 1-[2-(dimethylamino)ethyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methylpropyl)urea —— C19H33N3O2
1-[2-(dimethylamino)ethyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-(2-methylpropyl)urea
—— 1-[[1-(difluoromethyl)imidazol-2-yl]methyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea —— C17H22F2N4O2
1-[[1-(difluoromethyl)imidazol-2-yl]methyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea
—— 1-[[1-(difluoromethyl)imidazol-2-yl]methyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea —— C17H22F2N4O2
1-[[1-(difluoromethyl)imidazol-2-yl]methyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea
—— N-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1,4-thiazepane-4-carboxamide —— C16H24N2O2S
N-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1,4-thiazepane-4-carboxamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-fluorobenzamide —— C15H12BrFN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-fluorobenzamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3,4-dimethoxybenzamide —— C17H17BrN2O5
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3,4-dimethoxybenzamide
—— (1R,3S,5S)-3-(3-fluoro-5-hydroxyphenyl)-6,8-dioxabicyclo[3.2.1]octan-3-ol —— C12H13FO4
(1R,3S,5S)-3-(3-fluoro-5-hydroxyphenyl)-6,8-dioxabicyclo[3.2.1]octan-3-ol
—— (1R,3R,5S)-3-(3-fluoro-5-hydroxyphenyl)-6,8-dioxabicyclo[3.2.1]octan-3-ol —— C12H13FO4
(1R,3R,5S)-3-(3-fluoro-5-hydroxyphenyl)-6,8-dioxabicyclo[3.2.1]octan-3-ol
—— N-[2-[(S)-tert-butylsulfinyl]ethyl]-3-hydroxy-4-nitrobenzamide —— C13H18N2O5S
N-[2-[(S)-tert-butylsulfinyl]ethyl]-3-hydroxy-4-nitrobenzamide
—— N-[2-[(R)-tert-butylsulfinyl]ethyl]-3-hydroxy-4-nitrobenzamide —— C13H18N2O5S
N-[2-[(R)-tert-butylsulfinyl]ethyl]-3-hydroxy-4-nitrobenzamide
—— 5-[[[(1S,3S)-3-[(R)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol —— C16H25NO3S
5-[[[(1S,3S)-3-[(R)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol
—— 5-[[[(1S,3R)-3-[(S)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol —— C16H25NO3S
5-[[[(1S,3R)-3-[(S)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol
—— 5-[[[(1S,3R)-3-[(R)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol —— C16H25NO3S
5-[[[(1S,3R)-3-[(R)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol
—— 5-[[[(1S,3S)-3-[(S)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol —— C16H25NO3S
5-[[[(1S,3S)-3-[(S)-ethylsulfinyl]cyclohexyl]amino]methyl]-2-methoxyphenol
—— 5-[(Z)-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]hydrazinylidene]methyl]-2-methoxyphenol —— C14H11ClF3N3O2
5-[(Z)-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]hydrazinylidene]methyl]-2-methoxyphenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-propan-2-yloxybenzamide —— C18H19BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-propan-2-yloxybenzamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-propan-2-yloxybenzamide —— C18H20N2O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-propan-2-yloxybenzamide
—— 4-amino-3,5,6-trichloro-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]pyridin-1-ium-2-carboxamide —— C14H12Cl3N4O3+
4-amino-3,5,6-trichloro-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]pyridin-1-ium-2-carboxamide
—— (5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H10ClNO3S2
(5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one