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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-chloro-6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]cyclohexa-2,4-dien-1-one —— C14H11ClN2O4
4-chloro-6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]cyclohexa-2,4-dien-1-one
—— 2-(4-Methoxyphenyl)ethyl 4-methyl-2-oxo-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-triene-5-carboxylate —— C20H20N2O4S
2-(4-Methoxyphenyl)ethyl 4-methyl-2-oxo-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-triene-5-carboxylate
—— 2-(4-Methoxyphenyl)ethyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate —— C20H19NO4
2-(4-Methoxyphenyl)ethyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate
—— (5Z)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(2-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C17H16N4O2S2
(5Z)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(2-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-[(2-hydroxy-6-nitrophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid —— C12H8N2O6S2
2-[(5Z)-5-[(2-hydroxy-6-nitrophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
—— (5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-(2,3-dimethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
(5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-(2,3-dimethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C16H14N4O2S2
(5E)-5-[(3-hydroxyphenyl)methylidene]-2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— (4R)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16ClNO5
(4R)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 2-[(2Z,5S)-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate —— C18H14N3O4S-
2-[(2Z,5S)-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate
—— 2-(4-Methoxyphenyl)ethyl 3-methyl-1-[(4-methylphenyl)methyl]thieno[2,3-c]pyrazole-5-carboxylate —— C24H24N2O3S
2-(4-Methoxyphenyl)ethyl 3-methyl-1-[(4-methylphenyl)methyl]thieno[2,3-c]pyrazole-5-carboxylate
—— 2-(2-chloro-6-fluorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H13ClFNO3
2-(2-chloro-6-fluorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— (4S)-N-(4-fluorophenyl)-4-(2-hydroxy-3-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C18H15FN4O4S
(4S)-N-(4-fluorophenyl)-4-(2-hydroxy-3-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— ethyl (4R)-4-(2-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17BrN2O4S
ethyl (4R)-4-(2-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (4-hydroxy-3-methoxyphenyl)methyl-[(2R)-1-[(4-hydroxy-3-methoxyphenyl)methylazaniumyl]propan-2-yl]azanium —— C19H28N2O4+2
(4-hydroxy-3-methoxyphenyl)methyl-[(2R)-1-[(4-hydroxy-3-methoxyphenyl)methylazaniumyl]propan-2-yl]azanium
—— 5-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid —— C20H20N2O4
5-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid
—— 4-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate —— C18H17N2O5S-
4-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate
—— 5-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid —— C20H20N2O4
5-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid
—— (4R)-N-(3,5-dimethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C21H23N3O3S
(4R)-N-(3,5-dimethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— (2Z,6S)-2-[(2-hydroxy-5-methylanilino)methylidene]-6-methylcyclohexan-1-one —— C15H19NO2
(2Z,6S)-2-[(2-hydroxy-5-methylanilino)methylidene]-6-methylcyclohexan-1-one
—— 4-bromo-2-[(2R,6S)-2-(furan-2-yl)-4-phenyl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol —— C20H18BrN2O2+
4-bromo-2-[(2R,6S)-2-(furan-2-yl)-4-phenyl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-2-(furan-2-yl)-4-phenyl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C20H17BrN2O2
4-bromo-2-[(2S,6R)-2-(furan-2-yl)-4-phenyl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-((4-hydroxy-2-methylphenyl)amino)-6-propylpyrimidin-4(3H)-one —— C14H17N3O2
2-((4-hydroxy-2-methylphenyl)amino)-6-propylpyrimidin-4(3H)-one
—— Cyclopropylmethyl-[(4-hydroxy-3-methoxyphenyl)methyl]-propylazanium —— C15H24NO2+
Cyclopropylmethyl-[(4-hydroxy-3-methoxyphenyl)methyl]-propylazanium
—— (1R,2R,3S,4S)-3-[(2-hydroxy-4-nitrophenyl)carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid —— C15H14N2O6
(1R,2R,3S,4S)-3-[(2-hydroxy-4-nitrophenyl)carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
—— 2-(Dimethylazaniumyl)ethyl-[(2-hydroxy-3-methoxyphenyl)methyl]-methylazanium —— C13H24N2O2+2
2-(Dimethylazaniumyl)ethyl-[(2-hydroxy-3-methoxyphenyl)methyl]-methylazanium
—— 4-Methoxy-2-[(4-methylpiperazine-1,4-diium-1-yl)methyl]phenol —— C13H22N2O2+2
4-Methoxy-2-[(4-methylpiperazine-1,4-diium-1-yl)methyl]phenol
—— 4-[(1S)-1-(benzotriazol-1-yl)ethyl]-2-methoxyphenol —— C15H15N3O2
4-[(1S)-1-(benzotriazol-1-yl)ethyl]-2-methoxyphenol
—— (5S)-5-(2-hydroxy-3-methoxyphenyl)-11-methyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C17H20N3O3S+
(5S)-5-(2-hydroxy-3-methoxyphenyl)-11-methyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (1S,2S)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylcyclopropane-1-carboxamide —— C18H18N2O3
(1S,2S)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylcyclopropane-1-carboxamide
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methylphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H19NO5
(4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methylphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(3-chloro-4-methylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18ClNO5
(4R)-1-(3-chloro-4-methylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— [(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-(4-methoxyphenyl)methanone —— C22H20N2O4S
[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-(4-methoxyphenyl)methanone
—— 1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C16H16N2O3S
1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— (2R)-2-(4-hydroxy-3-methoxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile —— C14H19N2O2+
(2R)-2-(4-hydroxy-3-methoxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile
—— 4-[(R)-(4-methylpiperazine-1,4-diium-1-yl)-[1-(2-phenylethyl)tetrazol-5-yl]methyl]phenol —— C21H28N6O+2
4-[(R)-(4-methylpiperazine-1,4-diium-1-yl)-[1-(2-phenylethyl)tetrazol-5-yl]methyl]phenol
—— methyl (4S)-4-(2-bromo-3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C14H15BrN2O5
methyl (4S)-4-(2-bromo-3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (2Z)-3-(3-hydroxy-4-methoxyphenyl)-2-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]prop-2-enenitrile —— C19H13N3O4S
(2Z)-3-(3-hydroxy-4-methoxyphenyl)-2-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]prop-2-enenitrile
—— ethyl (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate —— C16H17NO5
ethyl (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate
—— prop-2-enyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C16H17N5O4
prop-2-enyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— 4-fluoro-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]benzamide —— C14H10FN3O4
4-fluoro-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]benzamide
—— (5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one —— C16H18BrN3O3S
(5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
—— ethyl (7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C15H17N5O4
ethyl (7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— (2R)-2-(4-bromo-2-hydroxyphenyl)-2-[(3R)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile —— C18H16BrN3O
(2R)-2-(4-bromo-2-hydroxyphenyl)-2-[(3R)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile
—— (2R)-2-(5-bromo-2-hydroxyphenyl)-2-[(3R)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile —— C18H16BrN3O
(2R)-2-(5-bromo-2-hydroxyphenyl)-2-[(3R)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile
—— ethyl (6R)-4-(bromomethyl)-6-(4-hydroxy-3-methoxyphenyl)-3-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate —— C16H19BrN2O5
ethyl (6R)-4-(bromomethyl)-6-(4-hydroxy-3-methoxyphenyl)-3-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— methyl (4R)-5-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate —— C21H20N2O6
methyl (4R)-5-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate
—— 2,6-dimethoxy-4-[[4-[(1S,3S)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H34N2O3+2
2,6-dimethoxy-4-[[4-[(1S,3S)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 2,6-dimethoxy-4-[[4-[(1R,3S)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H34N2O3+2
2,6-dimethoxy-4-[[4-[(1R,3S)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— propan-2-yl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C22H23N3O4
propan-2-yl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— (4R)-4-[(2-hydroxyphenyl)iminomethyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C17H15N3O2
(4R)-4-[(2-hydroxyphenyl)iminomethyl]-5-methyl-2-phenyl-4H-pyrazol-3-one