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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
—— 2,2-Dihydroxyethyl-[(3-hydroxy-4-methoxyphenyl)methyl]azanium —— C10H16NO4+
2,2-Dihydroxyethyl-[(3-hydroxy-4-methoxyphenyl)methyl]azanium
—— 2,2-Bis(phenylmethoxy)ethyl-[(3-hydroxy-4-methoxyphenyl)methyl]azanium —— C24H28NO4+
2,2-Bis(phenylmethoxy)ethyl-[(3-hydroxy-4-methoxyphenyl)methyl]azanium
—— 4-[(1S)-1-(dipropoxymethylamino)ethyl]-2-methoxyphenol —— C16H27NO4
4-[(1S)-1-(dipropoxymethylamino)ethyl]-2-methoxyphenol
—— dipropoxymethyl-[(1S)-1-(4-hydroxy-3-methoxyphenyl)ethyl]azanium —— C16H28NO4+
dipropoxymethyl-[(1S)-1-(4-hydroxy-3-methoxyphenyl)ethyl]azanium
—— 2-Hydroxyethyl-[(4-hydroxy-3-methoxyphenyl)methyl]azanium —— C10H16NO3+
2-Hydroxyethyl-[(4-hydroxy-3-methoxyphenyl)methyl]azanium
—— 2-(4-Hydroxy-3-methoxyphenyl)ethyl-[(3-hydroxyphenyl)methyl]azanium —— C16H20NO3+
2-(4-Hydroxy-3-methoxyphenyl)ethyl-[(3-hydroxyphenyl)methyl]azanium
—— dipropoxymethyl-[(1R)-1-(4-hydroxy-3-methoxyphenyl)ethyl]azanium —— C16H28NO4+
dipropoxymethyl-[(1R)-1-(4-hydroxy-3-methoxyphenyl)ethyl]azanium
—— 4-[(1R)-1-(dipropoxymethylamino)ethyl]-2-methoxyphenol —— C16H27NO4
4-[(1R)-1-(dipropoxymethylamino)ethyl]-2-methoxyphenol
—— 5-[(1R)-1-(2,2-dimethoxyethylamino)ethyl]-2-methoxyphenol —— C13H21NO4
5-[(1R)-1-(2,2-dimethoxyethylamino)ethyl]-2-methoxyphenol
—— 2-[(R)-(2-hydroxy-6-oxocyclohexen-1-yl)-(2-hydroxyphenyl)methyl]cyclohexane-1,3-dione —— C19H20O5
2-[(R)-(2-hydroxy-6-oxocyclohexen-1-yl)-(2-hydroxyphenyl)methyl]cyclohexane-1,3-dione
—— (4R)-4-[(4-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C17H16N2O2
(4R)-4-[(4-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— (4S)-4-[(2-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C17H16N2O2
(4S)-4-[(2-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— (4S)-4-[(4-hydroxyphenyl)-[(4S)-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl]methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C27H24N4O3
(4S)-4-[(4-hydroxyphenyl)-[(4S)-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl]methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— (4R)-4-[(4-hydroxyphenyl)-[(4R)-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl]methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C27H24N4O3
(4R)-4-[(4-hydroxyphenyl)-[(4R)-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl]methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— (4R)-4-[(2-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C17H16N2O2
(4R)-4-[(2-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— dipropan-2-yl (4R)-4-(2-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate —— C22H29NO6
dipropan-2-yl (4R)-4-(2-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate
—— dipropyl (4S)-4-(2-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate —— C22H29NO6
dipropyl (4S)-4-(2-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(3-nitroanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15N3O5S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(3-nitroanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-Bromo-4-[[4-(2-hydroxyethyl)piperazine-1,4-diium-1-yl]methyl]-6-methoxyphenol —— C14H23BrN2O3+2
2-Bromo-4-[[4-(2-hydroxyethyl)piperazine-1,4-diium-1-yl]methyl]-6-methoxyphenol
—— 2-Methoxy-4-(3-piperidin-1-ium-1-ylprop-1-ynyl)phenol —— C15H20NO2+
2-Methoxy-4-(3-piperidin-1-ium-1-ylprop-1-ynyl)phenol
—— 4-(2,2,6,6-Tetramethyl-1,3-dihydropyridin-1-ium-4-yl)phenol —— C15H22NO+
4-(2,2,6,6-Tetramethyl-1,3-dihydropyridin-1-ium-4-yl)phenol
—— (2R)-2-amino-2-(4-hydroxy-3-methoxyphenyl)acetic acid —— C9H11NO4
(2R)-2-amino-2-(4-hydroxy-3-methoxyphenyl)acetic acid
—— (2R)-2-azaniumyl-2-(4-hydroxy-3-methoxyphenyl)acetate —— C9H11NO4
(2R)-2-azaniumyl-2-(4-hydroxy-3-methoxyphenyl)acetate
—— methyl 2-[[(4R)-5-cyano-4-(4-hydroxy-3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanyl]acetate —— C15H13N3O6S
methyl 2-[[(4R)-5-cyano-4-(4-hydroxy-3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanyl]acetate
—— methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3R)-3-methylpiperazin-1-yl]propanoate —— C17H23F3N2O5
methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3R)-3-methylpiperazin-1-yl]propanoate
—— methyl (2S)-2-anilino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C18H18F3NO5
methyl (2S)-2-anilino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— [(2R)-1,1,1-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-methoxy-3-oxopropan-2-yl]azanium —— C12H15F3NO5+
[(2R)-1,1,1-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-methoxy-3-oxopropan-2-yl]azanium
—— methyl (2R)-2-chloro-3,3,3-trifluoro-2-(4-hydroxyphenyl)propanoate —— C10H8ClF3O3
methyl (2R)-2-chloro-3,3,3-trifluoro-2-(4-hydroxyphenyl)propanoate
—— methyl (2R)-2-amino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C12H14F3NO5
methyl (2R)-2-amino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3R)-3-methylpiperazine-1,4-diium-1-yl]propanoate —— C17H25F3N2O5+2
methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3R)-3-methylpiperazine-1,4-diium-1-yl]propanoate
—— methyl (2R)-2-anilino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C18H18F3NO5
methyl (2R)-2-anilino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— (2E,5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one —— C17H18ClNO4S
(2E,5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one
—— N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]-2-(1-methylbenzimidazol-2-yl)acetohydrazide —— C19H20N4O3
N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]-2-(1-methylbenzimidazol-2-yl)acetohydrazide
—— (2E,5Z)-2-(3,3-dimethyl-2-oxo-butylidene)-5-[(3-hydroxy-4-methoxy-phenyl)methylene]thiazolidin-4-one —— C17H19NO4S
(2E,5Z)-2-(3,3-dimethyl-2-oxo-butylidene)-5-[(3-hydroxy-4-methoxy-phenyl)methylene]thiazolidin-4-one
—— (2E)-2,5-bis[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]cyclopentan-1-one —— C23H24O7
(2E)-2,5-bis[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]cyclopentan-1-one
—— 1-(2-hydroxy-5-nitrophenyl)-3-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]urea —— C12H15N3O6S
1-(2-hydroxy-5-nitrophenyl)-3-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]urea
—— N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]-3-methylimidazo[1,2-a]pyridine-2-carbohydrazide —— C18H18N4O3
N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]-3-methylimidazo[1,2-a]pyridine-2-carbohydrazide
—— 4-[(6S)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-2-methoxyphenol —— C21H17N3O2
4-[(6S)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-2-methoxyphenol
—— 2-bromo-4-[(6R)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-6-methoxyphenol —— C21H16BrN3O2
2-bromo-4-[(6R)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-6-methoxyphenol
—— 2-bromo-4-[(6S)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-6-methoxyphenol —— C21H16BrN3O2
2-bromo-4-[(6S)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-6-methoxyphenol
—— 3-[(5E)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C13H10NO4S2-
3-[(5E)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
—— (5E)-5-(3,4-dihydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C10H7NO3S2
(5E)-5-(3,4-dihydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— (4E)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5-one —— C11H8N2O5
(4E)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5-one
—— (1R,2R)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylcyclopropane-1-carboxamide —— C18H18N2O3
(1R,2R)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylcyclopropane-1-carboxamide
—— (E)-(diaminomethylideneamino)-[(3-hydroxy-4-methoxyphenyl)methylidene]azanium —— C9H13N4O2+
(E)-(diaminomethylideneamino)-[(3-hydroxy-4-methoxyphenyl)methylidene]azanium
—— prop-2-enyl (6R)-6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate —— C17H19ClN2O5
prop-2-enyl (6R)-6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— butyl (6S)-6-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate —— C18H23BrN2O5
butyl (6S)-6-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— 2-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]guanidine —— C9H12N4O2
2-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]guanidine
—— (2R)-2-hydroxy-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2-phenylacetamide —— C15H13N3O5
(2R)-2-hydroxy-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2-phenylacetamide
—— (2S)-2-hydroxy-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2-phenylacetamide —— C15H13N3O5
(2S)-2-hydroxy-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2-phenylacetamide