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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
—— (1S,2R)-2-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C14H17NO4
(1S,2R)-2-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (1S,2S)-2-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C14H17NO4
(1S,2S)-2-[[(1R)-1-(2-hydroxyphenyl)ethyl]-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (E)-4-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobut-2-enoic acid —— C13H15NO4
(E)-4-[[(1S)-1-(2-hydroxyphenyl)ethyl]-methylamino]-4-oxobut-2-enoic acid
—— propan-2-yl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H34N2O7S
propan-2-yl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H38N2O7S
2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H32N2O7S
methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H34N2O7S
prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (1S,2S)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1S,2S)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H32N2O7S
methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (E)-4-[ethyl-[(1S)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobut-2-enoic acid —— C14H17NO4
(E)-4-[ethyl-[(1S)-1-(3-hydroxyphenyl)ethyl]amino]-4-oxobut-2-enoic acid
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O8S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— prop-2-enyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H32N2O7S
prop-2-enyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (1R,2R)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1R,2R)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— methyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
methyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (1R,2S)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1R,2S)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H28N2O7S
methyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-2-bromo-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide —— C15H22BrNO2
(2R)-2-bromo-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide
—— 2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H32N2O6S
2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (1S,2R)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1S,2R)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (1R,2R)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1R,2R)-2-[(2-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (2S)-2-bromo-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide —— C15H22BrNO2
(2S)-2-bromo-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide
—— 2-methoxyethyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H34N2O8S
2-methoxyethyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H32N2O8S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-2-bromo-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N,3-dimethylbutanamide —— C14H20BrNO2
(2R)-2-bromo-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N,3-dimethylbutanamide
—— propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O7S
propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S)-2-bromo-N-[(4-hydroxyphenyl)methyl]-N,3-dimethylbutanamide —— C13H18BrNO2
(2S)-2-bromo-N-[(4-hydroxyphenyl)methyl]-N,3-dimethylbutanamide
—— ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H28N2O6S
ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H30N2O7S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (1S,2S)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1S,2S)-2-[(3-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— 3-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propanamide —— C13H18ClNO2
3-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propanamide
—— ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H30N2O7S
ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-2-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propanamide —— C13H18ClNO2
(2R)-2-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propanamide
—— (1S,2S)-2-[(4-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid —— C13H15NO4
(1S,2S)-2-[(4-hydroxyphenyl)methyl-methylcarbamoyl]cyclopropane-1-carboxylic acid
—— (2S)-2-chloro-N-cyclopropyl-N-[(3-hydroxyphenyl)methyl]propanamide —— C13H16ClNO2
(2S)-2-chloro-N-cyclopropyl-N-[(3-hydroxyphenyl)methyl]propanamide
—— 5-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]pentanamide —— C15H22ClNO2
5-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]pentanamide
—— (2R)-2-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propanamide —— C13H18ClNO2
(2R)-2-chloro-N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]propanamide
—— ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H34N2O7S
ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-[3-methoxy-4-(3-methylbutoxy)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C37H32N2O7S
benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-2-bromo-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide —— C15H22BrNO2
(2R)-2-bromo-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-methylbutanamide
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O8S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-pentoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S)-2-chloro-N-[(3-hydroxyphenyl)methyl]-N-methylpropanamide —— C11H14ClNO2
(2S)-2-chloro-N-[(3-hydroxyphenyl)methyl]-N-methylpropanamide
—— (2S)-2-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propanamide —— C13H18ClNO2
(2S)-2-chloro-N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]propanamide
—— (2R)-2-bromo-N-[(2-hydroxyphenyl)methyl]-N,3-dimethylbutanamide —— C13H18BrNO2
(2R)-2-bromo-N-[(2-hydroxyphenyl)methyl]-N,3-dimethylbutanamide
—— (2S)-2-chloro-N-[(4-hydroxyphenyl)methyl]-N-methylpropanamide —— C11H14ClNO2
(2S)-2-chloro-N-[(4-hydroxyphenyl)methyl]-N-methylpropanamide
—— 2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C34H34N2O7S
2-methylpropyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-phenylmethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S)-2-chloro-N-[(2-hydroxyphenyl)methyl]-N-methylpropanamide —— C11H14ClNO2
(2S)-2-chloro-N-[(2-hydroxyphenyl)methyl]-N-methylpropanamide
—— prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H28N2O6S
prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2S)-2-bromo-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N,3-dimethylbutanamide —— C14H20BrNO2
(2S)-2-bromo-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N,3-dimethylbutanamide
—— (2R)-2-chloro-N-[(4-hydroxyphenyl)methyl]-N-methylpropanamide —— C11H14ClNO2
(2R)-2-chloro-N-[(4-hydroxyphenyl)methyl]-N-methylpropanamide
—— (2S)-2-bromo-N-cyclopropyl-N-[(3-hydroxyphenyl)methyl]-3-methylbutanamide —— C15H20BrNO2
(2S)-2-bromo-N-cyclopropyl-N-[(3-hydroxyphenyl)methyl]-3-methylbutanamide