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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-[(1R)-1-[2-aminoethyl(methyl)amino]ethyl]benzene-1,4-diol —— C11H18N2O2
2-[(1R)-1-[2-aminoethyl(methyl)amino]ethyl]benzene-1,4-diol
—— 2-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]-4-methylphenol —— C12H20N2O
2-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]-4-methylphenol
—— 2-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]benzene-1,4-diol —— C11H18N2O2
2-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]benzene-1,4-diol
—— 3-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]phenol —— C11H18N2O
3-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]phenol
—— 4-[[5-[(2R)-1-aminopropan-2-yl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C12H15N3O2
4-[[5-[(2R)-1-aminopropan-2-yl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— 5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(3-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H14Cl2N2O5S2
5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(3-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 1-(1,1-Dioxothiolan-3-yl)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C20H20N2O5S
1-(1,1-Dioxothiolan-3-yl)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 2-methoxy-5-[[(3R)-1-methylpiperidin-3-yl]methylamino]phenol —— C14H22N2O2
2-methoxy-5-[[(3R)-1-methylpiperidin-3-yl]methylamino]phenol
—— 2-[[(5Z)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-4,6-dioxo-1H-pyrimidin-2-yl]sulfanyl]acetamide —— C13H10BrN3O4S
2-[[(5Z)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-4,6-dioxo-1H-pyrimidin-2-yl]sulfanyl]acetamide
—— 5-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-6-oxonaphthalene-2-sulfonic acid —— C16H10N4O9S
5-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-6-oxonaphthalene-2-sulfonic acid
—— (5Z)-2-[(3R)-3-(4-chlorophenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C27H22ClN3O4S
(5Z)-2-[(3R)-3-(4-chlorophenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-[(3S)-3-(4-chlorophenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one —— C25H17Cl2N3O2S
(5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-[(3S)-3-(4-chlorophenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
—— (5Z)-2-[(3R)-3-[4-(dimethylamino)phenyl]-5-phenyl-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C28H26N4O3S
(5Z)-2-[(3R)-3-[4-(dimethylamino)phenyl]-5-phenyl-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-2-[(3S)-3-(4-chlorophenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C27H22ClN3O4S
(5Z)-2-[(3S)-3-(4-chlorophenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-2-[(3R)-3,5-bis(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C28H25N3O5S
(5Z)-2-[(3R)-3,5-bis(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-(furan-2-ylmethylidene)-2-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one —— C23H17N3O3S
(5Z)-5-(furan-2-ylmethylidene)-2-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
—— (5Z)-5-[(4-hydroxyphenyl)methylidene]-2-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one —— C25H19N3O3S
(5Z)-5-[(4-hydroxyphenyl)methylidene]-2-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-[(3S)-3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one —— C27H23N3O4S
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-[(3S)-3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-[(3S)-3-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one —— C27H23N3O5S
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-[(3S)-3-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one —— C25H19N3O3S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
—— 3-[[2-(3,4-dihydroxyphenyl)ethylamino]methylidene]-1H-indol-2-one —— C17H16N2O3
3-[[2-(3,4-dihydroxyphenyl)ethylamino]methylidene]-1H-indol-2-one
—— (5Z)-4-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-(pyridin-3-ylmethylidene)-1,3-thiazol-2-one —— C24H18N4O2S
(5Z)-4-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-(pyridin-3-ylmethylidene)-1,3-thiazol-2-one
—— 1-(1,1-Dioxothiolan-3-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C19H18N2O6S
1-(1,1-Dioxothiolan-3-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— (2R)-3-[(2,3-dihydroxyphenyl)methylamino]-2-methylpropanenitrile —— C11H14N2O2
(2R)-3-[(2,3-dihydroxyphenyl)methylamino]-2-methylpropanenitrile
—— (2R)-3-[[(1R)-1-(2,5-dihydroxyphenyl)ethyl]amino]-2-methylpropanenitrile —— C12H16N2O2
(2R)-3-[[(1R)-1-(2,5-dihydroxyphenyl)ethyl]amino]-2-methylpropanenitrile
—— (2S)-3-[[(1R)-1-(2,4-dihydroxyphenyl)ethyl]amino]-2-methylpropanenitrile —— C12H16N2O2
(2S)-3-[[(1R)-1-(2,4-dihydroxyphenyl)ethyl]amino]-2-methylpropanenitrile
—— (2R)-3-[[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-2-methylpropanenitrile —— C12H16N2O
(2R)-3-[[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-2-methylpropanenitrile
—— (2R)-3-[[(1R)-1-(2-hydroxy-5-methylphenyl)ethyl]amino]-2-methylpropanenitrile —— C13H18N2O
(2R)-3-[[(1R)-1-(2-hydroxy-5-methylphenyl)ethyl]amino]-2-methylpropanenitrile
—— (2S)-3-[(3,4-dihydroxyphenyl)methylamino]-2-methylpropanenitrile —— C11H14N2O2
(2S)-3-[(3,4-dihydroxyphenyl)methylamino]-2-methylpropanenitrile
—— 2-hydroxy-N'-[(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide —— C14H11N3O6
2-hydroxy-N'-[(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide
—— 5-[5-[(1S)-1-aminoethyl]-1,3-thiazol-2-yl]-2-methoxyphenol —— C12H14N2O2S
5-[5-[(1S)-1-aminoethyl]-1,3-thiazol-2-yl]-2-methoxyphenol
—— 1-Ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C17H16N2O4
1-Ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 1-(1,1-Dioxothiolan-3-yl)-5-[(4-hydroxyphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C18H16N2O5S
1-(1,1-Dioxothiolan-3-yl)-5-[(4-hydroxyphenyl)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 3-[(3-bromo-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H10BrN3O5S2
3-[(3-bromo-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (3S,4R)-4-(3-hydroxy-4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)-2-oxo-3,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C26H30N4O6
ethyl (3S,4R)-4-(3-hydroxy-4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)-2-oxo-3,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— 2-[(1S)-1-[2-[methyl(propan-2-yl)amino]ethylamino]ethyl]benzene-1,4-diol —— C14H24N2O2
2-[(1S)-1-[2-[methyl(propan-2-yl)amino]ethylamino]ethyl]benzene-1,4-diol
—— 4-[[(1R)-1-(furan-2-yl)propyl]amino]-3-nitrophenol —— C13H14N2O4
4-[[(1R)-1-(furan-2-yl)propyl]amino]-3-nitrophenol
—— N-[[1-(2-anilino-2-oxoethyl)-2-oxoindol-3-ylidene]amino]-2-hydroxy-5-nitrobenzamide —— C23H17N5O6
N-[[1-(2-anilino-2-oxoethyl)-2-oxoindol-3-ylidene]amino]-2-hydroxy-5-nitrobenzamide
—— 4-[(3R)-3-[[(1S)-1-cyclopentylethyl]amino]butyl]phenol —— C17H27NO
4-[(3R)-3-[[(1S)-1-cyclopentylethyl]amino]butyl]phenol
—— 4-chloro-6-[5-(4-hydroxy-3-methoxyphenyl)pyrazolidin-3-ylidene]cyclohexa-2,4-dien-1-one —— C16H15ClN2O3
4-chloro-6-[5-(4-hydroxy-3-methoxyphenyl)pyrazolidin-3-ylidene]cyclohexa-2,4-dien-1-one
—— 5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C15H13N3O3
5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— N'-[(3-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C16H16N2O6
N'-[(3-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— 1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]-3-(3-propan-2-yloxypropyl)urea —— C19H30N2O4
1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]-3-(3-propan-2-yloxypropyl)urea
—— 4-bromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H9BrN2O4
4-bromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 3,4,5-trihydroxy-N'-[1-(6-oxocyclohexa-2,4-dien-1-ylidene)propyl]benzohydrazide —— C16H16N2O5
3,4,5-trihydroxy-N'-[1-(6-oxocyclohexa-2,4-dien-1-ylidene)propyl]benzohydrazide
—— 4-[(2-hydroxy-3,5-dinitroanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one —— C18H15N5O6
4-[(2-hydroxy-3,5-dinitroanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one
—— N-[5-(5-bromo-2-oxo-1H-indol-3-ylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-4-hydroxy-3-methoxybenzamide —— C19H12BrN3O5S2
N-[5-(5-bromo-2-oxo-1H-indol-3-ylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-4-hydroxy-3-methoxybenzamide
—— (2S)-2-(4-hydroxy-3-methoxyphenyl)-2-(3-hydroxypropylamino)acetonitrile —— C12H16N2O3
(2S)-2-(4-hydroxy-3-methoxyphenyl)-2-(3-hydroxypropylamino)acetonitrile
—— (2R)-2-(2-hydroxyethylamino)-2-(4-hydroxyphenyl)acetonitrile —— C10H12N2O2
(2R)-2-(2-hydroxyethylamino)-2-(4-hydroxyphenyl)acetonitrile
—— 2-(4-chlorophenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one —— C18H16ClN3O2
2-(4-chlorophenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one