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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
—— 4-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C16H16NO6S2-
4-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
—— 5-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C16H17NO5S2
5-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
—— 6-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C17H19NO5S2
6-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— 5-[(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C17H19NO4S2
5-[(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
—— 3-[(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C13H10BrNO4S2
3-[(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— 6-Ethenyl-5-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C26H30O5
6-Ethenyl-5-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— (5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H14N2O2S2
(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate —— C16H16NO5S2-
5-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate
—— 5-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C16H17NO5S2
5-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
—— 6-[(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoate —— C17H18NO5S2-
6-[(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoate
—— 6-[(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoate —— C18H20NO4S2-
6-[(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoate
—— (5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO4S2
(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(4-fluorophenyl)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H14FNO2S2
(5Z)-3-(4-fluorophenyl)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 6-[(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C17H19NO5S2
6-[(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— (5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C19H18N2O4S
(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-3-(4-fluorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H9FN2O4S2
(5Z)-3-(4-fluorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C17H13BrN2O3S
(5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (5Z)-2-(2,5-dimethylphenyl)imino-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(2,5-dimethylphenyl)imino-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-2-(2,5-dimethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(2,5-dimethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C17H13BrN2O3S
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-2-(2,6-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H20N2O2S
(5E)-2-(2,6-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-2-(2,6-dimethylphenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(2,6-dimethylphenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-2-(2,6-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H20N2O4S
(5Z)-2-(2,6-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-2-(2,6-dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(2,6-dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C19H18N2O4S
(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— 2-(4-Methoxyphenyl)ethyl 2-phenyl-1,3-thiazole-4-carboxylate —— C19H17NO3S
2-(4-Methoxyphenyl)ethyl 2-phenyl-1,3-thiazole-4-carboxylate
—— (5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H13NO3S2
(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H12BrNO3S2
(5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (3E)-3-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one —— C16H11BrClNO3
(3E)-3-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one
—— (3E)-5-chloro-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12ClNO3
(3E)-5-chloro-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one
—— (3E)-5-chloro-3-[(2-hydroxy-5-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12ClNO3
(3E)-5-chloro-3-[(2-hydroxy-5-methoxyphenyl)methylidene]-1H-indol-2-one
—— (3E)-5-chloro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1H-indol-2-one —— C17H14ClNO4
(3E)-5-chloro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1H-indol-2-one
—— (Z)-3-(3-hydroxyphenyl)-2-pyridin-2-ylprop-2-enenitrile —— C14H10N2O
(Z)-3-(3-hydroxyphenyl)-2-pyridin-2-ylprop-2-enenitrile
—— 2-[(2-Bromo-5-hydroxy-4-methoxyphenyl)methylidene]propanedinitrile —— C11H7BrN2O2
2-[(2-Bromo-5-hydroxy-4-methoxyphenyl)methylidene]propanedinitrile
—— 2-[(4-Benzylsulfonylpiperazin-1-ium-1-yl)methyl]-6-methoxy-4-prop-2-enylphenol —— C22H29N2O4S+
2-[(4-Benzylsulfonylpiperazin-1-ium-1-yl)methyl]-6-methoxy-4-prop-2-enylphenol
—— 2-[(4-Benzylsulfonylpiperazin-1-yl)methyl]-6-methoxy-4-prop-2-enylphenol —— C22H28N2O4S
2-[(4-Benzylsulfonylpiperazin-1-yl)methyl]-6-methoxy-4-prop-2-enylphenol
—— 2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-(furan-2-yl)-3H-thieno[2,3-d]pyrimidin-4-one —— C19H13ClN2O4S
2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-(furan-2-yl)-3H-thieno[2,3-d]pyrimidin-4-one
—— 2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-[(2R)-2-methylbutyl]-3H-thieno[2,3-d]pyrimidin-4-one —— C21H23ClN2O3S
2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-[(2R)-2-methylbutyl]-3H-thieno[2,3-d]pyrimidin-4-one
—— 10-[(Z)-2-(3-hydroxy-4-methoxyphenyl)-1-methylsulfanylethenyl]-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),9-trien-12-one —— C19H18N2O3S2
10-[(Z)-2-(3-hydroxy-4-methoxyphenyl)-1-methylsulfanylethenyl]-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),9-trien-12-one
—— 2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-[(2S)-2-methylbutyl]-3H-thieno[2,3-d]pyrimidin-4-one —— C21H23ClN2O3S
2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-[(2S)-2-methylbutyl]-3H-thieno[2,3-d]pyrimidin-4-one
—— (3-hydroxy-4-nitrophenyl)-[(3R)-3-(2-methylpropyl)morpholin-4-yl]methanone —— C15H20N2O5
(3-hydroxy-4-nitrophenyl)-[(3R)-3-(2-methylpropyl)morpholin-4-yl]methanone
—— (3-hydroxy-4-nitrophenyl)-[(3S)-3-(2-methylpropyl)morpholin-4-yl]methanone —— C15H20N2O5
(3-hydroxy-4-nitrophenyl)-[(3S)-3-(2-methylpropyl)morpholin-4-yl]methanone
—— 4-[(E)-2-(4-hydroxy-3-nitrophenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one —— C15H15N3O4
4-[(E)-2-(4-hydroxy-3-nitrophenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one
—— 4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one —— C16H18N2O3
4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one
—— 4-[(E)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one —— C16H17BrN2O3
4-[(E)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one
—— 4-[(E)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one —— C17H20N2O4
4-[(E)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one
—— 4-[[[(1R,2S)-2-methylcyclohexyl]amino]methyl]-2-nitrophenol —— C14H20N2O3
4-[[[(1R,2S)-2-methylcyclohexyl]amino]methyl]-2-nitrophenol