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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
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methylpiperazin-4-ium-1-yl)-1,3-thiazol-4-one —— C16H19BrN3O3S+
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methylpiperazin-4-ium-1-yl)-1,3-thiazol-4-one
—— (2R)-2-(4-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile —— C14H16BrN3O
(2R)-2-(4-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile
—— (2S)-2-(4-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile —— C14H16BrN3O
(2S)-2-(4-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile
—— 2-(4-Methoxyphenyl)ethyl 5-(4-nitrophenyl)furan-2-carboxylate —— C20H17NO6
2-(4-Methoxyphenyl)ethyl 5-(4-nitrophenyl)furan-2-carboxylate
—— 2-[4-[(2R)-butan-2-yl]phenoxy]-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C19H21N3O5
2-[4-[(2R)-butan-2-yl]phenoxy]-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— 2-[4-[(2S)-butan-2-yl]phenoxy]-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C19H21N3O5
2-[4-[(2S)-butan-2-yl]phenoxy]-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— (4R)-3-(furan-2-yl)-4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C19H17N3O4
(4R)-3-(furan-2-yl)-4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4S)-3-(furan-2-yl)-4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C19H17N3O4
(4S)-3-(furan-2-yl)-4-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— 4-[(4S)-5-(1H-benzimidazol-2-ylmethyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]-2-methoxyphenol —— C21H21N5O2
4-[(4S)-5-(1H-benzimidazol-2-ylmethyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]-2-methoxyphenol
—— 4-[(4R)-5-(1H-benzimidazol-2-ylmethyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]-2-methoxyphenol —— C21H21N5O2
4-[(4R)-5-(1H-benzimidazol-2-ylmethyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]-2-methoxyphenol
—— 1-[[(3S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-3-propan-2-ylurea —— C17H27N3O3
1-[[(3S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-3-propan-2-ylurea
—— 3-[[(3-hydroxy-4-methoxyphenyl)methylamino]methyl]-N-[[(2R)-oxolan-2-yl]methyl]benzamide —— C21H26N2O4
3-[[(3-hydroxy-4-methoxyphenyl)methylamino]methyl]-N-[[(2R)-oxolan-2-yl]methyl]benzamide
—— 1-[[(3R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-3-propan-2-ylurea —— C17H27N3O3
1-[[(3R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-3-propan-2-ylurea
—— (2R)-2-(5-bromo-2-hydroxyphenyl)-2-[(3S)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile —— C18H16BrN3O
(2R)-2-(5-bromo-2-hydroxyphenyl)-2-[(3S)-5-methyl-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile
—— (2R)-2-(5-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile —— C14H16BrN3O
(2R)-2-(5-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile
—— [(4R)-2,2-dimethyloxan-4-yl]-[(4-hydroxy-3-methoxyphenyl)methyl]azanium —— C15H24NO3+
[(4R)-2,2-dimethyloxan-4-yl]-[(4-hydroxy-3-methoxyphenyl)methyl]azanium
—— 2-methoxy-5-[[(4R)-4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]methyl]phenol —— C17H23N3O2
2-methoxy-5-[[(4R)-4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]methyl]phenol
—— 2-methoxy-5-[[(4S)-4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]methyl]phenol —— C17H23N3O2
2-methoxy-5-[[(4S)-4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]methyl]phenol
—— methyl (4S)-4-(3-bromo-2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C13H12BrN3O6
methyl (4S)-4-(3-bromo-2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (6R)-6-(3-hydroxy-4-methoxyphenyl)-1,3,8-triazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-one —— C17H19N3O3
(6R)-6-(3-hydroxy-4-methoxyphenyl)-1,3,8-triazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-one
—— (6S)-6-(3-hydroxy-4-methoxyphenyl)-1,3,8-triazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-one —— C17H19N3O3
(6S)-6-(3-hydroxy-4-methoxyphenyl)-1,3,8-triazatricyclo[7.4.0.02,7]trideca-2(7),8-dien-4-one
—— methyl (4R)-4-(3-bromo-2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C13H12BrN3O6
methyl (4R)-4-(3-bromo-2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (6S)-4-(bromomethyl)-6-(4-hydroxy-3-methoxyphenyl)-3-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate —— C16H19BrN2O5
ethyl (6S)-4-(bromomethyl)-6-(4-hydroxy-3-methoxyphenyl)-3-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— (4R)-4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile —— C22H20N2O3
(4R)-4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile
—— (4S)-4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile —— C22H20N2O3
(4S)-4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile —— C23H22N2O4
(4S)-4-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile
—— 4-[[4-[(1S)-1-phenylethyl]-1,2,4-triazol-3-yl]methyl]phenol —— C17H17N3O
4-[[4-[(1S)-1-phenylethyl]-1,2,4-triazol-3-yl]methyl]phenol
—— 4-[[4-[(1R)-1-phenylethyl]-1,2,4-triazol-3-yl]methyl]phenol —— C17H17N3O
4-[[4-[(1R)-1-phenylethyl]-1,2,4-triazol-3-yl]methyl]phenol
—— methyl (4R)-5-cyano-4-(4-hydroxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate —— C19H16N2O4
methyl (4R)-5-cyano-4-(4-hydroxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate
—— methyl (4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate —— C20H18N2O5
methyl (4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate
—— methyl (4S)-5-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate —— C21H20N2O6
methyl (4S)-5-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate
—— methyl (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate —— C20H18N2O5
methyl (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate
—— 2-hydroxy-N-[[(3R)-1-[(5-hydroxy-2-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-2-methylpropanamide —— C17H26N2O4
2-hydroxy-N-[[(3R)-1-[(5-hydroxy-2-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-2-methylpropanamide
—— 2-hydroxy-N-[[(3S)-1-[(5-hydroxy-2-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-2-methylpropanamide —— C17H26N2O4
2-hydroxy-N-[[(3S)-1-[(5-hydroxy-2-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-2-methylpropanamide
—— N-[[(3S)-1-ethylpiperidin-3-yl]methyl]-3-(2-hydroxyphenyl)propanamide —— C17H26N2O2
N-[[(3S)-1-ethylpiperidin-3-yl]methyl]-3-(2-hydroxyphenyl)propanamide
—— (2R,4R)-2,4-bis(4-hydroxyphenyl)-3-methoxycarbonylcyclobutane-1-carboxylic acid —— C19H18O6
(2R,4R)-2,4-bis(4-hydroxyphenyl)-3-methoxycarbonylcyclobutane-1-carboxylic acid
—— 2,6-Dimethoxy-4-[(4-pentan-3-ylpiperazine-1,4-diium-1-yl)methyl]phenol —— C18H32N2O3+2
2,6-Dimethoxy-4-[(4-pentan-3-ylpiperazine-1,4-diium-1-yl)methyl]phenol
—— (2R)-2-hydroxy-4-(4-hydroxyphenyl)butanoic acid —— C10H12O4
(2R)-2-hydroxy-4-(4-hydroxyphenyl)butanoic acid
—— (2S,4S)-2,4-bis(4-hydroxyphenyl)-3-methoxycarbonylcyclobutane-1-carboxylic acid —— C19H18O6
(2S,4S)-2,4-bis(4-hydroxyphenyl)-3-methoxycarbonylcyclobutane-1-carboxylic acid
—— (2R,4S)-2,4-bis(4-hydroxyphenyl)-3-methoxycarbonylcyclobutane-1-carboxylic acid —— C19H18O6
(2R,4S)-2,4-bis(4-hydroxyphenyl)-3-methoxycarbonylcyclobutane-1-carboxylic acid
—— (2S)-2-hydroxy-4-(4-hydroxyphenyl)butanoic acid —— C10H12O4
(2S)-2-hydroxy-4-(4-hydroxyphenyl)butanoic acid
—— 2,6-dimethoxy-4-[[4-[(1S,3R)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H34N2O3+2
2,6-dimethoxy-4-[[4-[(1S,3R)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 2,6-dimethoxy-4-[[4-[(1R,3R)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H34N2O3+2
2,6-dimethoxy-4-[[4-[(1R,3R)-3-methylcyclohexyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 2-methoxyethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C22H23N3O5
2-methoxyethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— propan-2-yl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C22H23N3O4
propan-2-yl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— ethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C21H21N3O4
ethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— 2-[(4S)-2-amino-4,10-dihydro-1H-[1,3,5]triazino[1,2-a]benzimidazol-5-ium-4-yl]-6-nitrophenol —— C15H13N6O3+
2-[(4S)-2-amino-4,10-dihydro-1H-[1,3,5]triazino[1,2-a]benzimidazol-5-ium-4-yl]-6-nitrophenol
—— ethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C21H21N3O4
ethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— 2-[(4R)-2-amino-4,10-dihydro-1H-[1,3,5]triazino[1,2-a]benzimidazol-5-ium-4-yl]-6-nitrophenol —— C15H13N6O3+
2-[(4R)-2-amino-4,10-dihydro-1H-[1,3,5]triazino[1,2-a]benzimidazol-5-ium-4-yl]-6-nitrophenol
—— 2-[(4S)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-4-bromo-6-methoxyphenol —— C16H14BrN5O2
2-[(4S)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-4-bromo-6-methoxyphenol