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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
—— 4-[6-Hydroxy-5,7-di(propan-2-yl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl]benzene-1,2-diol —— C20H32N2O3+2
4-[6-Hydroxy-5,7-di(propan-2-yl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl]benzene-1,2-diol
—— 2-(2,4-Dihydroxyphenyl)-5-ethyl-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C17H24N2O3+2
2-(2,4-Dihydroxyphenyl)-5-ethyl-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 4-[(2S)-1,3-oxazolidin-2-yl]phenol —— C9H11NO2
4-[(2S)-1,3-oxazolidin-2-yl]phenol
—— 4-[(2S)-1,3-oxazolidin-3-ium-2-yl]phenol —— C9H12NO2+
4-[(2S)-1,3-oxazolidin-3-ium-2-yl]phenol
—— 2-(3,4-Dihydroxyphenyl)-5-ethyl-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C17H24N2O3+2
2-(3,4-Dihydroxyphenyl)-5-ethyl-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 5-Ethyl-2-(4-hydroxy-3-methoxyphenyl)-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C18H26N2O3+2
5-Ethyl-2-(4-hydroxy-3-methoxyphenyl)-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 5-Butyl-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C20H30N2O3+2
5-Butyl-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 2-[(2S,5S)-2,5-dimethylthiolan-1-ium-1-yl]benzene-1,4-diol —— C12H17O2S+
2-[(2S,5S)-2,5-dimethylthiolan-1-ium-1-yl]benzene-1,4-diol
—— 2-[(3S)-3-cyclohexylthian-1-ium-1-yl]benzene-1,4-diol —— C17H25O2S+
2-[(3S)-3-cyclohexylthian-1-ium-1-yl]benzene-1,4-diol
—— 2-(2-Hydroxy-3-methoxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C21H32N2O3+2
2-(2-Hydroxy-3-methoxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 2-[(3S)-3-butylthian-1-ium-1-yl]benzene-1,4-diol —— C15H23O2S+
2-[(3S)-3-butylthian-1-ium-1-yl]benzene-1,4-diol
—— 2-(2-Hydroxy-3-methoxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C21H34N2O3+2
2-(2-Hydroxy-3-methoxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— prop-2-enyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H18N2O5
prop-2-enyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— [(1R,3R)-3-methylcyclohexyl] (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H25BrN2O5
[(1R,3R)-3-methylcyclohexyl] (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-phenoxyethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H21BrN2O6
2-phenoxyethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— butyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H21BrN2O5
butyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 1-[(2S)-2-(2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H18N2O5
1-[(2S)-2-(2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-2-(2-hydroxy-3-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H18N2O5
1-[(2R)-2-(2-hydroxy-3-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H17BrN2O5
1-[(2R)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-5-[2-[(3-bromophenyl)methoxy]phenyl]-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C24H21BrN2O5
1-[(2R)-5-[2-[(3-bromophenyl)methoxy]phenyl]-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-5-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C24H21BrN2O5
1-[(2R)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-5-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C20H21BrN2O5
1-[(2S)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H17BrN2O5
1-[(2S)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-5-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C24H21BrN2O5
1-[(2S)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-5-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C20H21BrN2O5
1-[(2S)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C24H21BrN2O5
1-[(2R)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-2-(2-hydroxy-3-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H18N2O5
1-[(2S)-2-(2-hydroxy-3-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C24H21BrN2O5
1-[(2S)-5-[2-[(4-bromophenyl)methoxy]phenyl]-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C20H21BrN2O5
1-[(2R)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-5-[2-[(3-bromophenyl)methoxy]phenyl]-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C24H21BrN2O5
1-[(2S)-5-[2-[(3-bromophenyl)methoxy]phenyl]-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-2-(2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H18N2O5
1-[(2R)-2-(2-hydroxy-3-methoxyphenyl)-5-(2-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C20H21BrN2O5
1-[(2R)-5-(5-bromo-2-propan-2-yloxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2S)-2-(2-hydroxy-5-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H18N2O5
1-[(2S)-2-(2-hydroxy-5-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-2-(2-hydroxy-5-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C18H18N2O5
1-[(2R)-2-(2-hydroxy-5-methoxyphenyl)-5-(4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— [1,1,1,3,3,3-Hexafluoro-2-(2-hydroxy-5-methylphenyl)propan-2-yl]azanium —— C10H10F6NO+
[1,1,1,3,3,3-Hexafluoro-2-(2-hydroxy-5-methylphenyl)propan-2-yl]azanium
—— 4-[(1R)-2-chloro-1-(1,2,4-triazol-1-yl)ethyl]phenol —— C10H10ClN3O
4-[(1R)-2-chloro-1-(1,2,4-triazol-1-yl)ethyl]phenol
—— 4-[(1S)-2-chloro-1-(1,2,4-triazol-1-yl)ethyl]phenol —— C10H10ClN3O
4-[(1S)-2-chloro-1-(1,2,4-triazol-1-yl)ethyl]phenol
—— 2-phenoxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H22N2O6
2-phenoxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— [(2S)-2-methylpentyl] (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23N3O6
[(2S)-2-methylpentyl] (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— butyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H22N2O5
butyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— [(2R)-2-methylpentyl] (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23N3O6
[(2R)-2-methylpentyl] (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-ethoxyethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19N3O7
2-ethoxyethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-ethoxyethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19N3O7
2-ethoxyethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— butyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H22N2O5
butyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— [(2R)-2-methylpentyl] (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23N3O6
[(2R)-2-methylpentyl] (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-ethylsulfanylethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19N3O6S
2-ethylsulfanylethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-ethylsulfanylethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19N3O6S
2-ethylsulfanylethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2,4-Difluoro-6-nitrosophenol —— C6H3F2NO2
2,4-Difluoro-6-nitrosophenol
—— (5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)hexan-3-one —— C13H18O4
(5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)hexan-3-one
—— 5-[[[(2S)-1-hydroxybutan-2-yl]-[(2-methylphenyl)methyl]amino]methyl]-2-methoxyphenol —— C20H27NO3
5-[[[(2S)-1-hydroxybutan-2-yl]-[(2-methylphenyl)methyl]amino]methyl]-2-methoxyphenol