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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
—— (5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(4-phenyl-butyryl)-[1,2,4]triazepan-3-one —— C37H41N3O7
(5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(4-phenyl-butyryl)-[1,2,4]triazepan-3-one
—— (5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(5-morpholin-4-yl-pentanoyl)-[1,2,4]triazepan-3-one —— C36H46N4O8
(5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(5-morpholin-4-yl-pentanoyl)-[1,2,4]triazepan-3-one
—— 3-nitro-4-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol —— C11H12N4O3
3-nitro-4-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]phenol
—— (5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-benzyl)-1-(3-phenyl-propionyl)-[1,2,4]triazepan-3-one —— C34H35N3O5
(5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-benzyl)-1-(3-phenyl-propionyl)-[1,2,4]triazepan-3-one
—— (5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-[3-(4-methoxy-phenyl)-propionyl]-[1,2,4]triazepan-3-one —— C37H41N3O8
(5R,6R)-5-Benzyl-6-hydroxy-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-[3-(4-methoxy-phenyl)-propionyl]-[1,2,4]triazepan-3-one
—— 4-[(3S)-3-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol —— C15H21N3O
4-[(3S)-3-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol
—— 3-[(1S)-1-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol —— C13H17N3O
3-[(1S)-1-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol
—— 4-[(3S)-3-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol —— C15H21N3O
4-[(3S)-3-[[(1R)-1-(1H-pyrazol-5-yl)ethyl]amino]butyl]phenol
—— 4-[(1R)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol —— C17H27NO
4-[(1R)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol
—— 4-[(1S)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol —— C17H27NO
4-[(1S)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol
—— 3-[(1S)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol —— C17H27NO
3-[(1S)-1-[(4-ethylcyclohexyl)methylamino]ethyl]phenol
—— 2-(4-ethoxyphenyl)-N-(2-hydroxy-5-nitro-phenyl)acetamide —— C16H16N2O5
2-(4-ethoxyphenyl)-N-(2-hydroxy-5-nitro-phenyl)acetamide
—— N-(2-hydroxy-5-nitro-phenyl)-2-(4-nitrophenyl)acetamide —— C14H11N3O6
N-(2-hydroxy-5-nitro-phenyl)-2-(4-nitrophenyl)acetamide
—— 1-Ethyl-3,5-bis(3,4,5-trihydroxybenzylidene)piperidin-4-one —— C21H21NO7
1-Ethyl-3,5-bis(3,4,5-trihydroxybenzylidene)piperidin-4-one
—— 2,5-Bis(3,4,5-trihydroxybenzylidene)cyclopentanone —— C19H16O7
2,5-Bis(3,4,5-trihydroxybenzylidene)cyclopentanone
—— 3,5-Bis(4-hydroxy-3-nitrobenzylidene)piperidin-4-one —— C19H15N3O7
3,5-Bis(4-hydroxy-3-nitrobenzylidene)piperidin-4-one
—— 3,5-Bis(3,4,5-trihydroxybenzylidene)piperidin-4-one —— C19H17NO7
3,5-Bis(3,4,5-trihydroxybenzylidene)piperidin-4-one
—— 3,5-Bis(3-hydroxy-4-nitrobenzylidene)piperidin-4-one —— C19H15N3O7
3,5-Bis(3-hydroxy-4-nitrobenzylidene)piperidin-4-one
—— 3,5-Bis(4-hydroxy-3-nitrobenzylidene)-1-methylpiperidin-4-one —— C20H17N3O7
3,5-Bis(4-hydroxy-3-nitrobenzylidene)-1-methylpiperidin-4-one
—— (3E,5E)-3,5-bis[(3,4,5-trihydroxyphenyl)methylene]tetrahydropyran-4-one —— C19H16O8
(3E,5E)-3,5-bis[(3,4,5-trihydroxyphenyl)methylene]tetrahydropyran-4-one
—— 1-Methyl-3,5-bis(3,4,5-trihydroxybenzylidene)piperidin-4-one —— C20H19NO7
1-Methyl-3,5-bis(3,4,5-trihydroxybenzylidene)piperidin-4-one
—— 3-chloro-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylpropane-1-sulfonamide —— C12H18ClNO3S
3-chloro-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylpropane-1-sulfonamide
—— N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-oxobutanamide —— C14H19NO3
N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-oxobutanamide
—— 3-chloro-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide —— C11H16ClNO3S
3-chloro-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide
—— (3Z,5Z)-3,5-bis[(3,4,5-trihydroxyphenyl)methylene]tetrahydrothiopyran-4-one —— C19H16O7S
(3Z,5Z)-3,5-bis[(3,4,5-trihydroxyphenyl)methylene]tetrahydrothiopyran-4-one
—— 3-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide —— C13H20ClNO3S
3-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propane-1-sulfonamide
—— N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methyl-3-oxobutanamide —— C13H17NO3
N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methyl-3-oxobutanamide
—— 5-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylamino]-5-oxopentanoic acid —— C14H19NO4
5-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylamino]-5-oxopentanoic acid
—— (1S,2R)-2-[(4-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1S,2R)-2-[(4-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (1R,2S)-2-[(4-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1R,2S)-2-[(4-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one —— C17H8BrF3N2O4S2
(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
—— 5-chloro-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylpentanamide —— C14H20ClNO2
5-chloro-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylpentanamide
—— (1S,2R)-2-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C14H17NO4
(1S,2R)-2-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (1R,2S)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1R,2S)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (E)-4-[ethyl-[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobut-2-enoic acid —— C14H17NO4
(E)-4-[ethyl-[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobut-2-enoic acid
—— (1S,2R)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1S,2R)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— 5-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]pentanamide —— C15H22ClNO2
5-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]pentanamide
—— (2S)-2-bromo-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide —— C15H22BrNO2
(2S)-2-bromo-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide
—— 3-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propanamide —— C13H18ClNO2
3-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propanamide
—— (2S)-2-bromo-N-[(2-hydroxyphenyl)methyl]-N,3-dimethylbutanamide —— C13H18BrNO2
(2S)-2-bromo-N-[(2-hydroxyphenyl)methyl]-N,3-dimethylbutanamide
—— (5Z)-2-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazinylidene]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H16N4O4S2
(5Z)-2-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazinylidene]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2R)-2-bromo-N-[(4-hydroxy-3-methoxyphenyl)methyl]-N,3-dimethylbutanamide —— C14H20BrNO3
(2R)-2-bromo-N-[(4-hydroxy-3-methoxyphenyl)methyl]-N,3-dimethylbutanamide
—— ferrous; cyclopenta-1,3-diene; (E)-3-cyclopenta-1,3-dien-1-yl-1-(4-hydroxy-3-methoxy-phenyl)prop-2-en-1-one —— C20H18FeO3
ferrous; cyclopenta-1,3-diene; (E)-3-cyclopenta-1,3-dien-1-yl-1-(4-hydroxy-3-methoxy-phenyl)prop-2-en-1-one
—— (2R)-2-chloro-N-cyclopropyl-N-[(3-hydroxyphenyl)methyl]propanamide —— C13H16ClNO2
(2R)-2-chloro-N-cyclopropyl-N-[(3-hydroxyphenyl)methyl]propanamide
—— (2Z,5Z)-2,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one —— C21H20O5
(2Z,5Z)-2,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one
—— N,N'-bis[(5Z)-2-(4-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylene]-4-oxo-thiazolidin-3-yl]decanediamide —— C42H40Cl2N4O8S2
N,N'-bis[(5Z)-2-(4-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylene]-4-oxo-thiazolidin-3-yl]decanediamide
—— (2Z,6Z)-2,6-bis[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enylidene]cyclohexanone —— C26H26O5
(2Z,6Z)-2,6-bis[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enylidene]cyclohexanone
—— 2,6-Bis(3-(4-hydroxy-3-methoxyphenyl)-2-propenylidene)-4-methylcyclohexanone —— C27H28O5
2,6-Bis(3-(4-hydroxy-3-methoxyphenyl)-2-propenylidene)-4-methylcyclohexanone
—— 6-amino-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylhexanamide —— C15H24N2O2
6-amino-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylhexanamide
—— 6-amino-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methylhexanamide —— C15H24N2O2
6-amino-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methylhexanamide