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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-[(3-Hydroxyphenyl)methylideneamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C10H8N2O2S2
3-[(3-Hydroxyphenyl)methylideneamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-[(2,4-Dihydroxyphenyl)methylidene]-3-(2,3-dimethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
5-[(2,4-Dihydroxyphenyl)methylidene]-3-(2,3-dimethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-Amino-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C10H7N3O4S2
3-Amino-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2-Ethoxyphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O4S
2-(2-Ethoxyphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-(2-Ethoxyphenyl)imino-5-[(2-hydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C18H15N3O5S
2-(2-Ethoxyphenyl)imino-5-[(2-hydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-(3-hydroxyphenyl)imino-1,3-thiazolidin-4-one —— C17H14N2O4S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-(3-hydroxyphenyl)imino-1,3-thiazolidin-4-one
—— Oxolan-2-ylmethyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C18H22N2O6
Oxolan-2-ylmethyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(4-hydroxyphenyl)imino-1,3-thiazolidin-4-one —— C16H12N2O4S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(4-hydroxyphenyl)imino-1,3-thiazolidin-4-one
—— N-(2-hydroxy-4-nitrophenyl)-4-[5-[(3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C21H19N3O6S2
N-(2-hydroxy-4-nitrophenyl)-4-[5-[(3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— N-(2-hydroxy-5-nitrophenyl)-4-[5-[(3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C21H19N3O6S2
N-(2-hydroxy-5-nitrophenyl)-4-[5-[(3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— 2-[5-[(4-ethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)acetamide —— C20H17N3O6S2
2-[5-[(4-ethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)acetamide
—— 2-(4-Chlorophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H11ClN2O3S
2-(4-Chlorophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-Methoxy-2-[[4-[(2-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C19H25N3O4+2
4-Methoxy-2-[[4-[(2-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 2,6-Dimethoxy-4-[[4-[(3-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C21H30N2O4+2
2,6-Dimethoxy-4-[[4-[(3-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 3-[5-[(2,4-Dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C13H11NO5S2
3-[5-[(2,4-Dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— 4-[[4-[(4-Chlorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27ClN2O3+2
4-[[4-[(4-Chlorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— 2,6-Dimethoxy-4-[[4-[[2-(trifluoromethyl)phenyl]methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C21H27F3N2O3+2
2,6-Dimethoxy-4-[[4-[[2-(trifluoromethyl)phenyl]methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 4-[[4-(2-Adamantyl)piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C23H36N2O3+2
4-[[4-(2-Adamantyl)piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— (2,3-Dimethoxyphenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C22H29N2O6+
(2,3-Dimethoxyphenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
—— 4-Methoxy-2-[[4-[(4-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C19H25N3O4+2
4-Methoxy-2-[[4-[(4-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— [4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-(2-methoxyphenyl)methanone —— C21H27N2O5+
[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-(2-methoxyphenyl)methanone
—— [4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-phenylmethanone —— C20H25N2O4+
[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-phenylmethanone
—— (3,4-Dimethoxyphenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C22H29N2O6+
(3,4-Dimethoxyphenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
—— (3,5-Dimethoxyphenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C22H29N2O6+
(3,5-Dimethoxyphenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
—— (3-Fluorophenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C20H24FN2O4+
(3-Fluorophenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
—— 2-[(5-Ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(2-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C17H16N4O2S2
2-[(5-Ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(2-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 4-[[4-[(2-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27BrN2O3+2
4-[[4-[(2-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— [4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-pyridin-3-ylmethanone —— C19H24N3O4+
[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-pyridin-3-ylmethanone
—— 4-[[4-[(2-Fluorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27FN2O3+2
4-[[4-[(2-Fluorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— 4-[[4-[(4-Ethoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C22H32N2O4+2
4-[[4-[(4-Ethoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— 4-[[4-[(4-Ethylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C22H32N2O3+2
4-[[4-[(4-Ethylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— (3-Chlorophenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C20H24ClN2O4+
(3-Chlorophenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
—— (5R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one —— C14H16O4
(5R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one
—— (5S)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one —— C14H16O4
(5S)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one
—— (5S)-5-hydroxy-3-(2-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one —— C14H16O4
(5S)-5-hydroxy-3-(2-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one
—— Cycloheptyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C20H25ClN2O5
Cycloheptyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— Benzyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C20H20N2O5
Benzyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— Ethyl 4-(5-bromo-2-hydroxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C14H15BrN2O4
Ethyl 4-(5-bromo-2-hydroxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 3-(2,4-Dinitroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12N4O7S2
3-(2,4-Dinitroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-Methylbutyl 4-(4-hydroxy-3-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C17H21N3O6
3-Methylbutyl 4-(4-hydroxy-3-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-3-(3-hydroxyphenyl)-1,3-thiazolidine-2,4-dione —— C16H11NO5S
5-[(3,4-Dihydroxyphenyl)methylidene]-3-(3-hydroxyphenyl)-1,3-thiazolidine-2,4-dione
—— 4-[[4-[(3,4-Dimethoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C22H32N2O5+2
4-[[4-[(3,4-Dimethoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— diethyl 4-(3,4-dihydroxyphenyl)-6-methyl-2-methylidene-3,4-dihydro-1H-pyridine-3,5-dicarboxylate —— C19H23NO6
diethyl 4-(3,4-dihydroxyphenyl)-6-methyl-2-methylidene-3,4-dihydro-1H-pyridine-3,5-dicarboxylate
—— (4-Fluorophenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C20H24FN2O4+
(4-Fluorophenyl)-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
—— 2-(4-Chlorophenoxy)-1-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]ethanone —— C21H26ClN2O5+
2-(4-Chlorophenoxy)-1-[4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]ethanone
—— 1-[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-2-phenoxyethanone —— C21H27N2O5+
1-[4-[(4-Hydroxy-3,5-dimethoxyphenyl)methyl]piperazin-4-ium-1-yl]-2-phenoxyethanone
—— Butan-2-yl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C18H24N2O6
Butan-2-yl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 4-[[4-[(3-Chlorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27ClN2O3+2
4-[[4-[(3-Chlorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— 2,6-Dimethoxy-4-[[4-[(3-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C21H30N2O3+2
2,6-Dimethoxy-4-[[4-[(3-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 2,6-Dimethoxy-4-[[4-[(4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C21H30N2O4+2
2,6-Dimethoxy-4-[[4-[(4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol