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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
—— ethyl (2Z)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl (2Z)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-hydroxy-4-nitro-N-[(1R,3R)-3-(trifluoromethyl)cyclohexyl]benzamide —— C14H15F3N2O4
3-hydroxy-4-nitro-N-[(1R,3R)-3-(trifluoromethyl)cyclohexyl]benzamide
—— 3-hydroxy-4-nitro-N-[(1S,3R)-3-(trifluoromethyl)cyclohexyl]benzamide —— C14H15F3N2O4
3-hydroxy-4-nitro-N-[(1S,3R)-3-(trifluoromethyl)cyclohexyl]benzamide
—— 3-hydroxy-4-nitro-N-[(1S,3S)-3-(trifluoromethyl)cyclohexyl]benzamide —— C14H15F3N2O4
3-hydroxy-4-nitro-N-[(1S,3S)-3-(trifluoromethyl)cyclohexyl]benzamide
—— methyl (2Z)-2-[(2-chloro-5-methoxy-4-propan-2-yloxyphenyl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27ClN2O7S
methyl (2Z)-2-[(2-chloro-5-methoxy-4-propan-2-yloxyphenyl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-pyridin-3-ylurea —— C16H19N3O2
1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-pyridin-3-ylurea
—— 2-hydroxy-N'-[(Z)-indol-3-ylidenemethyl]-3,5-dinitrobenzohydrazide —— C16H11N5O6
2-hydroxy-N'-[(Z)-indol-3-ylidenemethyl]-3,5-dinitrobenzohydrazide
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H13BrN2O4S
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— N-cyclohexyl-2-{[(Z)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide —— C23H28N2O3S
N-cyclohexyl-2-{[(Z)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
—— 2-hydroxy-5-nitro-N-[(E)-(2-oxo-1-prop-2-enylindol-3-ylidene)amino]benzamide —— C18H14N4O5
2-hydroxy-5-nitro-N-[(E)-(2-oxo-1-prop-2-enylindol-3-ylidene)amino]benzamide
—— 4-methyl-2-[(1S)-1-(methylamino)ethyl]phenol —— C10H15NO
4-methyl-2-[(1S)-1-(methylamino)ethyl]phenol
—— N-[(1E)-4,4-dicyano-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)buta-1,3-dien-2-yl]benzamide —— C20H15N3O4
N-[(1E)-4,4-dicyano-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)buta-1,3-dien-2-yl]benzamide
—— 2-(4-bromophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H15BrN2O4
2-(4-bromophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 3-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-hydroxy-5-methoxybenzamide —— C20H22BrNO5
3-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-hydroxy-5-methoxybenzamide
—— (2Z)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]-3-oxo-3-pyrrolidin-1-ylpropanenitrile —— C24H21N3O4S
(2Z)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]-3-oxo-3-pyrrolidin-1-ylpropanenitrile
—— 3-bromo-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-hydroxy-5-methoxybenzamide —— C20H22BrNO5
3-bromo-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-hydroxy-5-methoxybenzamide
—— 2-hydroxy-5-nitro-N-[(Z)-(5-nitrothiophen-2-yl)methylideneamino]benzamide —— C12H8N4O6S
2-hydroxy-5-nitro-N-[(Z)-(5-nitrothiophen-2-yl)methylideneamino]benzamide
—— methyl (6R)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C16H17N3O5S
methyl (6R)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— ethyl (2Z)-5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2Z)-5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (3Z)-3-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-fluorophenyl)furan-2-one —— C17H10BrFO3
(3Z)-3-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-fluorophenyl)furan-2-one
—— (5E)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,3-dimethylphenyl)-2-(2,3-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C27H24Br2N2O3S
(5E)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,3-dimethylphenyl)-2-(2,3-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— (Z)-2-(1,3-benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enal —— C16H11N3O5
(Z)-2-(1,3-benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enal
—— ethyl (6R)-3-(4-chlorophenyl)-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C20H18ClN3O5S
ethyl (6R)-3-(4-chlorophenyl)-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— 2-methoxyethyl (6S)-6-(4-hydroxy-3-nitrophenyl)-3,4-dimethyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C16H19N3O6S
2-methoxyethyl (6S)-6-(4-hydroxy-3-nitrophenyl)-3,4-dimethyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— ethyl (6R)-6-(4-hydroxy-3-nitrophenyl)-3,4-dimethyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C15H17N3O5S
ethyl (6R)-6-(4-hydroxy-3-nitrophenyl)-3,4-dimethyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— (5Z)-2-amino-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazol-4-one —— C10H7N3O4S
(5Z)-2-amino-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazol-4-one
—— N-{4-[(1Z)-1-{2-[(3,4,5-trihydroxyphenyl)carbonyl]hydrazinylidene}ethyl]phenyl}cyclopropanecarboxamide —— C19H19N3O5
N-{4-[(1Z)-1-{2-[(3,4,5-trihydroxyphenyl)carbonyl]hydrazinylidene}ethyl]phenyl}cyclopropanecarboxamide
—— (4Z)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one —— C18H16N4O4
(4Z)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one
—— N-[(E)-1-(5-chlorothiophen-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C13H11ClN2O4S
N-[(E)-1-(5-chlorothiophen-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— (5E)-5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-[(piperidin-1-YL)methyl]-1,3-thiazolidine-2,4-dione —— C17H20N2O4S
(5E)-5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-[(piperidin-1-YL)methyl]-1,3-thiazolidine-2,4-dione
—— (E)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enamide —— C20H12N4O7
(E)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enamide
—— ethyl (2Z)-5-(4-hydroxyphenyl)-7-methyl-2-[(1-methylpyrazol-4-yl)methylidene]-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H20N4O4S
ethyl (2Z)-5-(4-hydroxyphenyl)-7-methyl-2-[(1-methylpyrazol-4-yl)methylidene]-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-hydroxy-5-nitro-N-[(Z)-thiophen-2-ylmethylideneamino]benzamide —— C12H9N3O4S
2-hydroxy-5-nitro-N-[(Z)-thiophen-2-ylmethylideneamino]benzamide
—— (5Z)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C10H6N2O5S
(5Z)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 5-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C16H13NO2S
5-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— 3,4,5-trihydroxy-N-[(Z)-1-pyridin-3-ylethylideneamino]benzamide —— C14H13N3O4
3,4,5-trihydroxy-N-[(Z)-1-pyridin-3-ylethylideneamino]benzamide
—— (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one —— C11H10N2O3S
(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
—— (2R)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid —— C20H18N2O5S
(2R)-2-[(4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanylpropanoic acid
—— (2R)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid —— C25H20N2O5S
(2R)-2-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-1-phenylimidazol-2-yl]sulfanyl-2-phenylacetic acid
—— 6-[(S)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]piperazin-1-yl]-(3-hydroxy-4-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(S)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]piperazin-1-yl]-(3-hydroxy-4-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 6-[(R)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(2-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(R)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(2-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 6-[(R)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(4-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(R)-[4-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(4-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— methyl (4Z)-1-cyclohexyl-4-(2-hydroxy-3-methoxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C21H25NO5
methyl (4Z)-1-cyclohexyl-4-(2-hydroxy-3-methoxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 6-[(S)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(2-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol —— C34H34N2O10
6-[(S)-[4-[(S)-(6-hydroxy-1,3-benzodioxol-5-yl)-(2-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]-(2-hydroxy-3-methoxyphenyl)methyl]-1,3-benzodioxol-5-ol
—— 2-methoxy-5-[(Z)-[[4-(4-methoxyanilino)-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]phenol —— C24H22N8O5
2-methoxy-5-[(Z)-[[4-(4-methoxyanilino)-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]phenol
—— (3Z)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]-1-prop-2-enylindol-2-one —— C19H17N3O3
(3Z)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]-1-prop-2-enylindol-2-one
—— N-[(Z)-(4-bromophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H11BrN2O4
N-[(Z)-(4-bromophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— (3E)-3-[(4-hydroxyphenyl)methylidene]-2-oxoindolizine-1-carbonitrile —— C16H10N2O2
(3E)-3-[(4-hydroxyphenyl)methylidene]-2-oxoindolizine-1-carbonitrile
—— (5Z)-3-benzyl-5-(2,3-dibromo-6-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C18H13Br2NO3S2
(5Z)-3-benzyl-5-(2,3-dibromo-6-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 4-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-2-phenylimidazol-1-yl]benzenesulfonic acid —— C23H18N2O6S
4-[(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-oxo-2-phenylimidazol-1-yl]benzenesulfonic acid