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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-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2-(3,4,5-trimethoxyphenyl)-1,3-thiazolidin-4-one —— C21H25NO6S
3-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2-(3,4,5-trimethoxyphenyl)-1,3-thiazolidin-4-one
—— 7-ethenyl-8-(2-hydroxy-6-methoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
7-ethenyl-8-(2-hydroxy-6-methoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2-(2-Hydroxy-3-methoxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C17H24N2O3+2
2-(2-Hydroxy-3-methoxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 5-(2-Hydroxyphenyl)-3-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyrazol-3-ol —— C11H10F4N2O2
5-(2-Hydroxyphenyl)-3-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyrazol-3-ol
—— 7-ethenyl-8-(4-hydroxy-3-methylphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O3
7-ethenyl-8-(4-hydroxy-3-methylphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2-{(E)-[(2-methyl-1H-benzimidazol-6-yl)imino]methyl}-4-nitrophenol —— C15H12N4O3
2-{(E)-[(2-methyl-1H-benzimidazol-6-yl)imino]methyl}-4-nitrophenol
—— ethyl 2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-5-(4-methyl-3-nitrophenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22ClN3O7S
ethyl 2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-5-(4-methyl-3-nitrophenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methylanilino)acetamide —— C17H18BrN3O3
N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methylanilino)acetamide
—— 4-(5-methyl-2,3-dihydro-1H-pyrazol-3-yl)phenol —— C10H12N2O
4-(5-methyl-2,3-dihydro-1H-pyrazol-3-yl)phenol
—— ethyl 5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl 5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-methoxy-2-[[(3-propyl-1H-benzimidazol-3-ium-2-yl)amino]methyl]phenol —— C18H22N3O2+
5-methoxy-2-[[(3-propyl-1H-benzimidazol-3-ium-2-yl)amino]methyl]phenol
—— ethyl 5-(2,4-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23N3O8S
ethyl 5-(2,4-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-(4-fluorophenyl)-N'-[(4-hydroxy-3-methoxyphenyl)methylideneamino]butanediamide —— C18H18FN3O4
N-(4-fluorophenyl)-N'-[(4-hydroxy-3-methoxyphenyl)methylideneamino]butanediamide
—— 2-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-4,6-dinitrophenol —— C9H8N8O5
2-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-4,6-dinitrophenol
—— 7-ethenyl-8-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C25H28O5
7-ethenyl-8-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3-[(2-Fluorophenyl)methyl]-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C19H16FNO3S
3-[(2-Fluorophenyl)methyl]-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 6-Ethenyl-5-(3-hydroxy-4-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H26O4
6-Ethenyl-5-(3-hydroxy-4-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— [4-[(Dimethylazaniumyl)methyl]-2,5-dihydroxyphenyl]methyl-dimethylazanium —— C12H22N2O2+2
[4-[(Dimethylazaniumyl)methyl]-2,5-dihydroxyphenyl]methyl-dimethylazanium
—— 8-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-ethenyl-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H23ClO4
8-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-ethenyl-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— Pentyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C19H26N2O6
Pentyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 4-[(3-bromophenyl)methoxy]-N-[(2-hydroxy-5-nitrophenyl)methylideneamino]benzamide —— C21H16BrN3O5
4-[(3-bromophenyl)methoxy]-N-[(2-hydroxy-5-nitrophenyl)methylideneamino]benzamide
—— 3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C26H24N2O2S
3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 3-Ethyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C14H15NO3S
3-Ethyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 2-[4-(Dimethylamino)phenyl]-3-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-1,3-thiazolidin-4-one —— C20H24N2O3S
2-[4-(Dimethylamino)phenyl]-3-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-1,3-thiazolidin-4-one
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H12N2O3S2
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 8a-bromo-7-ethenyl-8-(2-hydroxy-3-prop-2-enylphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H21BrO3
8a-bromo-7-ethenyl-8-(2-hydroxy-3-prop-2-enylphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2-(2-chlorophenoxy)-N-(2-hydroxy-4-nitrophenyl)acetamide —— C14H11ClN2O5
2-(2-chlorophenoxy)-N-(2-hydroxy-4-nitrophenyl)acetamide
—— 4-[(1R)-1-hydroxy-2-morpholin-4-ylethyl]phenol —— C12H17NO3
4-[(1R)-1-hydroxy-2-morpholin-4-ylethyl]phenol
—— 3-[(1R)-1-hydroxy-2-morpholin-4-ylethyl]phenol —— C12H17NO3
3-[(1R)-1-hydroxy-2-morpholin-4-ylethyl]phenol
—— 3-[(1S)-1-hydroxy-2-(4-methylpiperidin-1-yl)ethyl]phenol —— C14H21NO2
3-[(1S)-1-hydroxy-2-(4-methylpiperidin-1-yl)ethyl]phenol
—— 3-[(1R)-2-(diethylamino)-1-hydroxyethyl]phenol —— C12H19NO2
3-[(1R)-2-(diethylamino)-1-hydroxyethyl]phenol
—— 3-[(1S)-1-hydroxy-2-morpholin-4-ylethyl]phenol —— C12H17NO3
3-[(1S)-1-hydroxy-2-morpholin-4-ylethyl]phenol
—— 4-[(1S)-1-hydroxy-2-(4-methylpiperidin-1-yl)ethyl]phenol —— C14H21NO2
4-[(1S)-1-hydroxy-2-(4-methylpiperidin-1-yl)ethyl]phenol
—— 3-[(1S)-1-hydroxy-2-piperidin-1-ylethyl]phenol —— C13H19NO2
3-[(1S)-1-hydroxy-2-piperidin-1-ylethyl]phenol
—— 3-[(1R)-1-hydroxy-2-(4-methylpiperidin-1-yl)ethyl]phenol —— C14H21NO2
3-[(1R)-1-hydroxy-2-(4-methylpiperidin-1-yl)ethyl]phenol
—— 3-[(1R)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol —— C12H17NO2
3-[(1R)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol
—— 3-[(1S)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol —— C12H17NO2
3-[(1S)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol
—— 3-[(1R)-1-hydroxy-2-piperidin-1-ylethyl]phenol —— C13H19NO2
3-[(1R)-1-hydroxy-2-piperidin-1-ylethyl]phenol
—— 2-[(1S)-2-(diethylamino)-1-hydroxyethyl]phenol —— C12H19NO2
2-[(1S)-2-(diethylamino)-1-hydroxyethyl]phenol
—— 2-[(1S)-2-(dimethylamino)-1-hydroxyethyl]phenol —— C10H15NO2
2-[(1S)-2-(dimethylamino)-1-hydroxyethyl]phenol
—— 4-[(1R)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol —— C12H17NO2
4-[(1R)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol
—— 2-[(1R)-2-(dimethylamino)-1-hydroxyethyl]phenol —— C10H15NO2
2-[(1R)-2-(dimethylamino)-1-hydroxyethyl]phenol
—— 4-[(1S)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol —— C12H17NO2
4-[(1S)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol
—— 2-[(1R)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol —— C12H17NO2
2-[(1R)-1-hydroxy-2-pyrrolidin-1-ylethyl]phenol
—— 4-[[[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methylideneamino]-1,2,4-triazol-3-yl]hydrazinylidene]methyl]-2,6-dimethoxyphenol —— C20H22N6O6
4-[[[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methylideneamino]-1,2,4-triazol-3-yl]hydrazinylidene]methyl]-2,6-dimethoxyphenol
—— 2-amino-N-[(4-hydroxy-3-nitrophenyl)methylideneamino]-4-methyl-1,3-thiazole-5-carboxamide —— C12H11N5O4S
2-amino-N-[(4-hydroxy-3-nitrophenyl)methylideneamino]-4-methyl-1,3-thiazole-5-carboxamide
—— N-ethyl-N-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]adamantane-1-carboxamide —— C21H29NO3
N-ethyl-N-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]adamantane-1-carboxamide
—— 4-[2-(4-methoxy-3-propan-2-ylphenyl)ethoxy]benzoic acid —— C19H22O4
4-[2-(4-methoxy-3-propan-2-ylphenyl)ethoxy]benzoic acid
—— N-(2-hydroxy-5-nitrophenyl)-2-(4-methoxyphenoxy)acetamide —— C15H14N2O6
N-(2-hydroxy-5-nitrophenyl)-2-(4-methoxyphenoxy)acetamide
—— 4-[2-(3-ethyl-4-methoxyphenyl)ethoxy]-3-methoxybenzaldehyde —— C19H22O4
4-[2-(3-ethyl-4-methoxyphenyl)ethoxy]-3-methoxybenzaldehyde