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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
—— N-[4-[(4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-2-phenylimidazol-1-yl]phenyl]propanamide —— C26H23N3O4
N-[4-[(4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-2-phenylimidazol-1-yl]phenyl]propanamide
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-3-(5-propylsulfanyl-1H-indol-2-yl)imidazol-4-one —— C28H25N3O3S
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenyl-3-(5-propylsulfanyl-1H-indol-2-yl)imidazol-4-one
—— (5Z)-3-(4,6-dichloro-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one —— C24H15Cl2N3O3S
(5Z)-3-(4,6-dichloro-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one
—— (5Z)-3-(5,6-dimethyl-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one —— C26H21N3O3S
(5Z)-3-(5,6-dimethyl-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one
—— (5Z)-3-(5-chloro-6-fluoro-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one —— C24H15ClFN3O3S
(5Z)-3-(5-chloro-6-fluoro-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one
—— Bazzanin Q —— C28H16Cl6O4
Bazzanin Q
—— 2,6-bis[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyran-4-one —— C23H20O6
2,6-bis[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]pyran-4-one
—— 2,6-bis[(E)-2-(3,4-dihydroxyphenyl)ethenyl]pyran-4-one —— C21H16O6
2,6-bis[(E)-2-(3,4-dihydroxyphenyl)ethenyl]pyran-4-one
—— N,N'-bis[(5E)-2-(4-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-3-yl]decanediamide —— C42H40Cl2N4O8S2
N,N'-bis[(5E)-2-(4-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-3-yl]decanediamide
—— (2E)-2-[(4-hydroxyphenyl)methylidene]-6-(piperidin-1-ylmethyl)cyclohexan-1-one —— C19H25NO2
(2E)-2-[(4-hydroxyphenyl)methylidene]-6-(piperidin-1-ylmethyl)cyclohexan-1-one
—— 2-(2-Cyano-1-phenylethenesulfonyl)-3-(3,4-dihydroxyphenyl)acrylonitrile —— C18H12N2O4S
2-(2-Cyano-1-phenylethenesulfonyl)-3-(3,4-dihydroxyphenyl)acrylonitrile
—— (2E,5E)-2,5-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]cyclopentan-1-one —— C25H24O5
(2E,5E)-2,5-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]cyclopentan-1-one
—— (2E,6E)-2,6-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]-4-methylcyclohexan-1-one —— C27H28O5
(2E,6E)-2,6-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]-4-methylcyclohexan-1-one
—— 2-cyano-3-[(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]prop-2-enamide —— C15H11N3O4S2
2-cyano-3-[(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]prop-2-enamide
—— 2-((5-(2-Hydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)methylene)malonamide —— C14H11N3O4S2
2-((5-(2-Hydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)methylene)malonamide
—— 3-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-pyridinyl)acrylonitrile —— C14H8Br2N2O
3-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-pyridinyl)acrylonitrile
—— 2-[[(5E)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]methylidene]propanediamide —— C14H11N3O4S2
2-[[(5E)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]methylidene]propanediamide
—— (E)-2-diethoxyphosphoryl-3-(2,5-dihydroxyphenyl)prop-2-enenitrile —— C13H16NO5P
(E)-2-diethoxyphosphoryl-3-(2,5-dihydroxyphenyl)prop-2-enenitrile
—— (4Z)-2-amino-6-(3-chloro-2-hydroxy-5-methylphenyl)-4-(6-oxocyclohexa-2,4-dien-1-ylidene)-1H-pyridine-3-carbonitrile —— C19H14ClN3O2
(4Z)-2-amino-6-(3-chloro-2-hydroxy-5-methylphenyl)-4-(6-oxocyclohexa-2,4-dien-1-ylidene)-1H-pyridine-3-carbonitrile
—— Amyloxy iso-eugenol —— C15H22O3
Amyloxy iso-eugenol
—— 4-Hydroxymandelate —— C8H7O4-
4-Hydroxymandelate
—— R-(-)-p-hydroxymandelate —— C8H7O4
R-(-)-p-hydroxymandelate
—— (E)-5-(2-hydroxy-5-methoxy-3-methylphenyl)-1-[(1R,3'S,5R,6S,7R)-3'-hydroxy-1,2',2',5-tetramethylspiro[bicyclo[3.2.0]heptane-7,5'-oxolane]-6-yl]-3-methylpent-3-en-1-one —— C28H40O5
(E)-5-(2-hydroxy-5-methoxy-3-methylphenyl)-1-[(1R,3'S,5R,6S,7R)-3'-hydroxy-1,2',2',5-tetramethylspiro[bicyclo[3.2.0]heptane-7,5'-oxolane]-6-yl]-3-methylpent-3-en-1-one
—— 2-[(E)-heptadec-10-enyl]-6-methoxy-benzene-1,4-diol —— C24H40O3
2-[(E)-heptadec-10-enyl]-6-methoxy-benzene-1,4-diol
—— methyl (4Z)-1-[2-(cyclohex-1-en-1-yl)ethyl]-4-(4-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C22H25NO4
methyl (4Z)-1-[2-(cyclohex-1-en-1-yl)ethyl]-4-(4-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 2-(2,4-dichlorophenoxy)-N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]acetamide —— C15H11Cl2N3O5
2-(2,4-dichlorophenoxy)-N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]acetamide
—— 2-(2,4-dichlorophenoxy)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C15H11Cl2N3O5
2-(2,4-dichlorophenoxy)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— (2Z,5Z)-3-cyclopentyl-5-(4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C21H20N2O2S
(2Z,5Z)-3-cyclopentyl-5-(4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (3S)-N-[(Z)-[5-(4-bromophenyl)furan-2-yl]methylideneamino]-3-(2-hydroxy-4-methoxyphenyl)butanamide —— C22H21BrN2O4
(3S)-N-[(Z)-[5-(4-bromophenyl)furan-2-yl]methylideneamino]-3-(2-hydroxy-4-methoxyphenyl)butanamide
—— (3R)-N-[(Z)-[5-(4-bromophenyl)furan-2-yl]methylideneamino]-3-(2-hydroxy-4-methoxyphenyl)butanamide —— C22H21BrN2O4
(3R)-N-[(Z)-[5-(4-bromophenyl)furan-2-yl]methylideneamino]-3-(2-hydroxy-4-methoxyphenyl)butanamide
—— (5E)-2-(3-chloro-2-methylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C19H17ClN2O3S
(5E)-2-(3-chloro-2-methylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-3-(3-chlorophenyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C17H12ClNO4S
(5E)-3-(3-chlorophenyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-diethyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C16H17BrN2O4S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-diethyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-[[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid —— C19H16N2O5S
4-[[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
—— (5E)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-[(2R)-butan-2-yl]-1,3-thiazolidine-2,4-dione —— C15H16BrNO4S
(5E)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-[(2R)-butan-2-yl]-1,3-thiazolidine-2,4-dione
—— 2-[(5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C20H17BrN2O5S
2-[(5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— 2-[(5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C20H17ClN2O5S
2-[(5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— (5E)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-[(2S)-butan-2-yl]-1,3-thiazolidine-2,4-dione —— C15H16BrNO4S
(5E)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-[(2S)-butan-2-yl]-1,3-thiazolidine-2,4-dione
—— 2-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C20H18N2O5S
2-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— (5E)-2-(2,5-dimethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C20H20N2O3S
(5E)-2-(2,5-dimethylphenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— 2-[5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-ethoxyphenyl)acetamide —— C21H19BrN2O6S
2-[5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-ethoxyphenyl)acetamide
—— 4-[[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid —— C19H16N2O5S
4-[[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
—— (3E)-5-bromo-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1H-indol-2-one —— C17H14BrNO4
(3E)-5-bromo-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1H-indol-2-one
—— (2E,5E)-5-(5-bromo-2-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C16H11BrN2O2S
(2E,5E)-5-(5-bromo-2-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— N-(4-ethoxyphenyl)-2-[5-(3-hydroxy-4-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-(4-ethoxyphenyl)-2-[5-(3-hydroxy-4-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— (2R)-2-(4-cyanophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide —— C18H17N3O4
(2R)-2-(4-cyanophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide
—— (2S)-2-(4-cyanophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide —— C18H17N3O4
(2S)-2-(4-cyanophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide
—— (5E)-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5E)-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5E)-5-[(2-bromo-5-hydroxyphenyl)methylidene]-2-(4-bromophenyl)imino-1,3-thiazolidin-4-one —— C16H10Br2N2O2S
(5E)-5-[(2-bromo-5-hydroxyphenyl)methylidene]-2-(4-bromophenyl)imino-1,3-thiazolidin-4-one
—— N-[(Z)-(5-bromothiophen-2-yl)methylideneamino]-3,4,5-trihydroxybenzamide —— C12H9BrN2O4S
N-[(Z)-(5-bromothiophen-2-yl)methylideneamino]-3,4,5-trihydroxybenzamide