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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
—— 2-hydroxy-3,5-dinitro-N'-[(Z)-(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide —— C14H10N4O7
2-hydroxy-3,5-dinitro-N'-[(Z)-(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide
—— (5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-chloro-4-fluorobenzyl)-1,3-thiazolidine-2,4-dione —— C18H12BrClFNO4S
(5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-chloro-4-fluorobenzyl)-1,3-thiazolidine-2,4-dione
—— N'~1~-[(Z)-1-(1-Adamantyl)ethylidene]-3,4,5-trihydroxybenzohydrazide —— C19H24N2O4
N'~1~-[(Z)-1-(1-Adamantyl)ethylidene]-3,4,5-trihydroxybenzohydrazide
—— (5Z)-3-[2-(azepan-1-yl)-2-oxoethyl]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C20H24N2O6S
(5Z)-3-[2-(azepan-1-yl)-2-oxoethyl]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— ethyl (5Z)-2-(4-ethoxyanilino)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C26H27NO6S
ethyl (5Z)-2-(4-ethoxyanilino)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— N-[(Z)-1-(3-chlorophenyl)propylideneamino]-3,4,5-trihydroxybenzamide —— C16H15ClN2O4
N-[(Z)-1-(3-chlorophenyl)propylideneamino]-3,4,5-trihydroxybenzamide
—— methyl (4Z)-4-(2-hydroxy-3-methoxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C15H15NO5
methyl (4Z)-4-(2-hydroxy-3-methoxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 5-[(Z)-[benzyl(phenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C21H20N2O2
5-[(Z)-[benzyl(phenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— N-[trans-3-ethoxytetrahydro-2H-pyran-4-yl]-3-hydroxy-4-methoxybenzamide —— C15H21NO5
N-[trans-3-ethoxytetrahydro-2H-pyran-4-yl]-3-hydroxy-4-methoxybenzamide
—— (5E)-5-[(3,4-dihydroxyphenyl)methylidene]-3-propyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H13NO3S2
(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-3-propyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-ethyl-3-(3-hydroxyphenyl)-N-(tetrahydro-2H-pyran-4-ylmethyl)propanamide —— C17H25NO3
N-ethyl-3-(3-hydroxyphenyl)-N-(tetrahydro-2H-pyran-4-ylmethyl)propanamide
—— 3-(3-hydroxyphenyl)-N-[(1-pyrrolidin-1-ylcyclohexyl)methyl]propanamide —— C20H30N2O2
3-(3-hydroxyphenyl)-N-[(1-pyrrolidin-1-ylcyclohexyl)methyl]propanamide
—— Rubrolide A —— C17H8Br4O4
Rubrolide A
—— (5Z)-3-(3,4-dichlorophenyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C18H13Cl2NO4S2
(5Z)-3-(3,4-dichlorophenyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— (5E)-5-(3-hydroxy-4-methoxybenzylidene)-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione —— C14H15NO5S
(5E)-5-(3-hydroxy-4-methoxybenzylidene)-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione
—— 5-(5-bromo-2-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C11H6BrN3O5S
5-(5-bromo-2-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— (4Z)-2-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxybenzylidene)-5-{[(4-methylphenyl)sulfanyl]methyl}-2,4-dihydro-3H-pyrazol-3-one —— C26H21N3O3S2
(4Z)-2-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxybenzylidene)-5-{[(4-methylphenyl)sulfanyl]methyl}-2,4-dihydro-3H-pyrazol-3-one
—— 2-bromo-N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide —— C14H10BrN3O4
2-bromo-N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide
—— 2-[(5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-methylphenyl)acetamide —— C20H17BrN2O5S
2-[(5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-methylphenyl)acetamide
—— methyl (5E)-2-anilino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C20H17NO5S
methyl (5E)-2-anilino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— (4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-1H-pyrazol-5-one —— C10H8ClN3O2
(4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-1H-pyrazol-5-one
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-propan-2-ylthiourea —— C12H17N3O2S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-propan-2-ylthiourea
—— 4-(3-Hydroxybenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one —— C14H19NO3
4-(3-Hydroxybenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one
—— 4-(2-Hydroxy-5-methylbenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one —— C15H21NO3
4-(2-Hydroxy-5-methylbenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one
—— (2E)-2-{[(4-hydroxy-2-methylphenyl)amino]methylidene}-6-methylcyclohexanone —— C15H19NO2
(2E)-2-{[(4-hydroxy-2-methylphenyl)amino]methylidene}-6-methylcyclohexanone
—— (5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-(5-Chloro-2-hydroxybenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one —— C14H18ClNO3
4-(5-Chloro-2-hydroxybenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one
—— 2-methoxy-5-{[2-(6-methoxypyridin-3-yl)-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl]methyl}phenol —— C20H22N4O3
2-methoxy-5-{[2-(6-methoxypyridin-3-yl)-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl]methyl}phenol
—— 3-hydroxy-N-[trans-3-hydroxytetrahydro-2H-pyran-4-yl]-4-methoxybenzamide —— C13H17NO5
3-hydroxy-N-[trans-3-hydroxytetrahydro-2H-pyran-4-yl]-4-methoxybenzamide
—— (4Z)-1-(3-chlorophenyl)-4-[(3,5-dibromo-2-hydroxyphenyl)methylidene]pyrazolidine-3,5-dione —— C16H9Br2ClN2O3
(4Z)-1-(3-chlorophenyl)-4-[(3,5-dibromo-2-hydroxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 1,3-diethyl-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C15H15N3O5S
1,3-diethyl-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— ethyl 2-(3-hydroxy-4-methoxybenzylidene)-5-(4-isopropoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl 2-(3-hydroxy-4-methoxybenzylidene)-5-(4-isopropoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (6E)-4-chloro-6-[(3-hydroxy-4-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H12ClNO2
(6E)-4-chloro-6-[(3-hydroxy-4-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— (6Z)-2-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]-3,4-dimethylcyclohexa-2,4-dien-1-one —— C16H16BrNO2
(6Z)-2-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]-3,4-dimethylcyclohexa-2,4-dien-1-one
—— (6Z)-2-bromo-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]-3,4-dimethylcyclohexa-2,4-dien-1-one —— C17H18BrNO2
(6Z)-2-bromo-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]-3,4-dimethylcyclohexa-2,4-dien-1-one
—— (5Z)-1-benzyl-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C22H19N3O3
(5Z)-1-benzyl-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— N'-[(Z)-(3-hydroxy-4-nitrophenyl)methylidene]-6-methylpyridine-3-carbohydrazide —— C14H12N4O4
N'-[(Z)-(3-hydroxy-4-nitrophenyl)methylidene]-6-methylpyridine-3-carbohydrazide
—— N-[(Z)-[1-[(2-chlorophenyl)methyl]-2-methylindol-3-yl]methylideneamino]-2-hydroxy-3-nitrobenzamide —— C24H19ClN4O4
N-[(Z)-[1-[(2-chlorophenyl)methyl]-2-methylindol-3-yl]methylideneamino]-2-hydroxy-3-nitrobenzamide
—— ethyl (2Z)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O6S
ethyl (2Z)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-Hydroxy-4-methoxy-N-[(4-methyl-2-propyl-1,3-thiazol-5-YL)methyl]benzamide —— C16H20N2O3S
3-Hydroxy-4-methoxy-N-[(4-methyl-2-propyl-1,3-thiazol-5-YL)methyl]benzamide
—— ethyl (2Z)-2-(furan-3-ylmethylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O5S
ethyl (2Z)-2-(furan-3-ylmethylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-(4-hydroxyphenyl)-N-[1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl]propanamide —— C19H28N2O3
3-(4-hydroxyphenyl)-N-[1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl]propanamide
—— 3-hydroxy-4-methoxy-N-[(3S,4S)-3-(oxan-4-yl)oxan-4-yl]benzamide —— C18H25NO5
3-hydroxy-4-methoxy-N-[(3S,4S)-3-(oxan-4-yl)oxan-4-yl]benzamide
—— 5-[5-(4-chlorophenyl)-2-(trifluoromethyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-2-methoxyphenol —— C19H14ClF3N4O2
5-[5-(4-chlorophenyl)-2-(trifluoromethyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-2-methoxyphenol
—— ethyl (2Z)-5-(4-ethoxyphenyl)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O6S
ethyl (2Z)-5-(4-ethoxyphenyl)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[5-[(Z)-[(2-hydroxy-5-nitrobenzoyl)hydrazinylidene]methyl]furan-2-yl]benzoic acid —— C19H13N3O7
4-[5-[(Z)-[(2-hydroxy-5-nitrobenzoyl)hydrazinylidene]methyl]furan-2-yl]benzoic acid
—— benzene-1,2-diol;(NE)-N-[1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-ylidene]nitramide —— C6H6O2*C9H10ClN5O2
benzene-1,2-diol;(NE)-N-[1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-ylidene]nitramide
—— 4-[cyclooctyl(methyl)amino]-2-methylphenol —— C16H25NO
4-[cyclooctyl(methyl)amino]-2-methylphenol
—— 1-Chloro-3-(3-chloro-6-hydroxy-2,4-dimethylanilino)propan-2-one —— C11H13Cl2NO2
1-Chloro-3-(3-chloro-6-hydroxy-2,4-dimethylanilino)propan-2-one
—— Ethyl 3,5-dihydroxybenzenecarboximidate —— C9H11NO3
Ethyl 3,5-dihydroxybenzenecarboximidate