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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
—— methyl (4E)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-prop-2-enylpyrrole-3-carboxylate —— C17H17NO4
methyl (4E)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-prop-2-enylpyrrole-3-carboxylate
—— (4E)-1-(3-chloro-4-methylphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C19H17ClN2O5
(4E)-1-(3-chloro-4-methylphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-N'-[(Z)-(3-hydroxyphenyl)methylideneamino]butanediamide —— C18H18N4O4
N-[(E)-(3-hydroxyphenyl)methylideneamino]-N'-[(Z)-(3-hydroxyphenyl)methylideneamino]butanediamide
—— N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-N'-[(E)-1-(3-hydroxyphenyl)ethylideneamino]hexanediamide —— C22H26N4O4
N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-N'-[(E)-1-(3-hydroxyphenyl)ethylideneamino]hexanediamide
—— methyl (4E)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate —— C14H13NO4
methyl (4E)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate
—— (Z)-3-(5-chloro-1-methylimidazol-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one —— C14H13ClN2O3
(Z)-3-(5-chloro-1-methylimidazol-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
—— 4-amino-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboxamide —— C10H9N5O3
4-amino-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboxamide
—— (5E)-3-(4-hydroxyphenyl)-5-(pyridin-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H10N2O2S2
(5E)-3-(4-hydroxyphenyl)-5-(pyridin-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2Z,5E)-2-[(Z)-benzylidenehydrazinylidene]-3-[(1R)-cyclopent-2-en-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C22H19N3O2S
(2Z,5E)-2-[(Z)-benzylidenehydrazinylidene]-3-[(1R)-cyclopent-2-en-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2E,5E)-2-[(E)-benzylidenehydrazinylidene]-3-[(1R)-cyclopent-2-en-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C22H19N3O2S
(2E,5E)-2-[(E)-benzylidenehydrazinylidene]-3-[(1R)-cyclopent-2-en-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (Z)-2-cyano-3-[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]prop-2-enamide —— C14H9N3O5
(Z)-2-cyano-3-[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]prop-2-enamide
—— (Z)-3-[5-(4-bromophenyl)furan-2-yl]-2-cyano-N-(2-hydroxy-4-nitrophenyl)prop-2-enamide —— C20H12BrN3O5
(Z)-3-[5-(4-bromophenyl)furan-2-yl]-2-cyano-N-(2-hydroxy-4-nitrophenyl)prop-2-enamide
—— (Z)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enamide —— C20H12N4O7
(Z)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enamide
—— 4-[(1S)-1-hydroxy-2-(2-hydroxyethylamino)ethyl]benzene-1,2-diol —— C10H15NO4
4-[(1S)-1-hydroxy-2-(2-hydroxyethylamino)ethyl]benzene-1,2-diol
—— (5Z)-5-[(3-bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H10BrNO3S2
(5Z)-5-[(3-bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[(4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-2-phenylimidazol-1-yl]benzenesulfonic acid —— C23H18N2O6S
4-[(4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-2-phenylimidazol-1-yl]benzenesulfonic acid
—— (4E)-1-(3,4-dimethylphenyl)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C19H18N2O4
(4E)-1-(3,4-dimethylphenyl)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 3-[bis[(2R)-2-hydroxypropyl]amino]-2-methylphenol —— C13H21NO3
3-[bis[(2R)-2-hydroxypropyl]amino]-2-methylphenol
—— 3-[[(2S)-2-hydroxypropyl]-[(2R)-2-hydroxypropyl]amino]-2-methylphenol —— C13H21NO3
3-[[(2S)-2-hydroxypropyl]-[(2R)-2-hydroxypropyl]amino]-2-methylphenol
—— 3,4-bis[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol —— C14H22O6
3,4-bis[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol
—— ethyl (2Z,5S)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18ClN3O6S
ethyl (2Z,5S)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18ClN3O6S
ethyl (2Z,5R)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5E)-5-[(2-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C21H19FN2O5S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5E)-5-[(2-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— 4-bromo-N-[(E)-(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide —— C14H10BrN3O4
4-bromo-N-[(E)-(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide
—— (Z)-(3,5-dibromo-2-hydroxyphenyl)methylidene-hydroxy-phenylazanium —— C13H10Br2NO2+
(Z)-(3,5-dibromo-2-hydroxyphenyl)methylidene-hydroxy-phenylazanium
—— [(Z)-4-(4-hydroxyphenyl)butan-2-ylideneamino]urea —— C11H15N3O2
[(Z)-4-(4-hydroxyphenyl)butan-2-ylideneamino]urea
—— (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide —— C19H18N2O5S2
(2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5E)-5-[(2-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C22H22N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5E)-5-[(2-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— (2E,5Z)-2-[(Z)-benzylidenehydrazinylidene]-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C17H11N5O6S
(2E,5Z)-2-[(Z)-benzylidenehydrazinylidene]-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-hydroxy-N-[(E)-(3-methoxyphenyl)methylideneamino]-3,5-dinitrobenzamide —— C15H12N4O7
2-hydroxy-N-[(E)-(3-methoxyphenyl)methylideneamino]-3,5-dinitrobenzamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-(furan-2-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C18H16N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-(furan-2-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— (6Z)-2,4-dichloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H11Cl2NO2
(6Z)-2,4-dichloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— (Z)-4-(1,3-benzothiazol-2-yl)-5-(2-bromo-5-hydroxy-4-methoxyphenyl)pent-4-enoic acid —— C19H16BrNO4S
(Z)-4-(1,3-benzothiazol-2-yl)-5-(2-bromo-5-hydroxy-4-methoxyphenyl)pent-4-enoic acid
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-4-oxo-5-[(Z)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C22H20N2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-4-oxo-5-[(Z)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one —— C22H17ClN2O3S
2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one
—— 5-[(E)-[[4-anilino-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-2-methoxyphenol —— C23H20N8O4
5-[(E)-[[4-anilino-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-2-methoxyphenol
—— 4-[(1R,2R)-1-hydroxy-2-(propan-2-ylamino)butyl]benzene-1,2-diol —— C13H21NO3
4-[(1R,2R)-1-hydroxy-2-(propan-2-ylamino)butyl]benzene-1,2-diol
—— 2-[(4S)-octan-4-yl]phenol —— C14H22O
2-[(4S)-octan-4-yl]phenol
—— (2R,4R)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid —— C11H12BrNO4S
(2R,4R)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
—— (2R,4S)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid —— C11H12BrNO4S
(2R,4S)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
—— (2S,4R)-2-(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)-1,3-thiazolidine-4-carboxylic acid —— C14H17NO4S
(2S,4R)-2-(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)-1,3-thiazolidine-4-carboxylic acid
—— (5E)-3-(2-hydroxy-4-nitrophenyl)-2-phenyl-5-[(Z)-3-phenylprop-2-enylidene]imidazol-4-one —— C24H17N3O4
(5E)-3-(2-hydroxy-4-nitrophenyl)-2-phenyl-5-[(Z)-3-phenylprop-2-enylidene]imidazol-4-one
—— 4-[(1S)-2-amino-1-(N-methylanilino)ethyl]-2-methoxy-6-prop-2-enylphenol —— C19H24N2O2
4-[(1S)-2-amino-1-(N-methylanilino)ethyl]-2-methoxy-6-prop-2-enylphenol
—— 14-tert-butyl-31-hydroxy-29-methyl-3,10,18,25-tetrazapentacyclo[25.3.1.112,16.04,9.019,24]dotriaconta-1(30),4,6,8,10,12,14,16,19,21,23,27(31),28-tridecaene-2,26,32-trione —— C33H30N4O4
14-tert-butyl-31-hydroxy-29-methyl-3,10,18,25-tetrazapentacyclo[25.3.1.112,16.04,9.019,24]dotriaconta-1(30),4,6,8,10,12,14,16,19,21,23,27(31),28-tridecaene-2,26,32-trione
—— 1-[7-(4-hydroxy-3-methoxyphenyl)-5-methylidene-6,7-dihydro-1H-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethanone —— C15H16N4O3
1-[7-(4-hydroxy-3-methoxyphenyl)-5-methylidene-6,7-dihydro-1H-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethanone
—— 2-[(1S)-2-amino-1-(4-hydroxy-N-methylanilino)ethyl]-6-methoxyphenol —— C16H20N2O3
2-[(1S)-2-amino-1-(4-hydroxy-N-methylanilino)ethyl]-6-methoxyphenol
—— 2-[(1S)-2-amino-1-(N-ethylanilino)ethyl]-6-methoxyphenol —— C17H22N2O2
2-[(1S)-2-amino-1-(N-ethylanilino)ethyl]-6-methoxyphenol
—— 4-[(1R)-2-amino-1-(4-hydroxy-N-methylanilino)ethyl]-2-methoxyphenol —— C16H20N2O3
4-[(1R)-2-amino-1-(4-hydroxy-N-methylanilino)ethyl]-2-methoxyphenol
—— 2-[(1R)-2-amino-1-(2,3-dihydroindol-1-yl)ethyl]-6-methoxyphenol —— C17H20N2O2
2-[(1R)-2-amino-1-(2,3-dihydroindol-1-yl)ethyl]-6-methoxyphenol
—— 2-[(1S)-2-amino-1-(2,3-dihydroindol-1-yl)ethyl]-6-methoxyphenol —— C17H20N2O2
2-[(1S)-2-amino-1-(2,3-dihydroindol-1-yl)ethyl]-6-methoxyphenol