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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
—— 1-[(3R)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O2S
1-[(3R)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— 1-[(3R)-3-(3-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O2S
1-[(3R)-3-(3-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— 1-[(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H13N3O4S
1-[(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— tert-butyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H22N2O4S
tert-butyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (2Z,5S)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23N3O8S
ethyl (2Z,5S)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4R)-6-amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-thiophen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C19H16N4O4S
(4R)-6-amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-thiophen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— [(E)-but-2-enyl] (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H20N2O5
[(E)-but-2-enyl] (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2,6-Dimethoxy-4-[(4-propylsulfonylpiperazin-1-ium-1-yl)methyl]phenol —— C16H27N2O5S+
2,6-Dimethoxy-4-[(4-propylsulfonylpiperazin-1-ium-1-yl)methyl]phenol
—— methyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxyphenyl)propanoate —— C10H9F3O4
methyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxyphenyl)propanoate
—— propyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17N3O6
propyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methylsulfanylethyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19ClN2O5S
2-methylsulfanylethyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methoxyethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19BrN2O6
2-methoxyethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— prop-2-enyl (4S)-6-(2-amino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-3,4-dihydropyridine-3-carboxylate —— C20H21N3O5S
prop-2-enyl (4S)-6-(2-amino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-3,4-dihydropyridine-3-carboxylate
—— 5-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-2-[[(2R,6R)-2,6-dimethylmorpholin-4-yl]methyl]benzene-1,4-diol —— C20H32N2O4
5-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-2-[[(2R,6R)-2,6-dimethylmorpholin-4-yl]methyl]benzene-1,4-diol
—— 5-[[(2S,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]-2-[[(2R,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]benzene-1,4-diol —— C20H34N2O4+2
5-[[(2S,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]-2-[[(2R,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]benzene-1,4-diol
—— 2-propan-2-yloxyethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H24N2O6
2-propan-2-yloxyethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (2S)-3-benzyl-2-(3-hydroxyphenyl)-1,3-thiazolidin-4-one —— C16H15NO2S
(2S)-3-benzyl-2-(3-hydroxyphenyl)-1,3-thiazolidin-4-one
—— (4Z)-2-(4-fluorophenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one —— C18H16FN3O2
(4Z)-2-(4-fluorophenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one
—— (4R,4aS,5S,8aR)-4-(4-hydroxy-3-methoxyphenyl)-1,3,5,6,8-pentamethyl-4,4a,5,8a-tetrahydropyrimido[4,5-d]pyrimidine-2,7-dione —— C18H26N4O4
(4R,4aS,5S,8aR)-4-(4-hydroxy-3-methoxyphenyl)-1,3,5,6,8-pentamethyl-4,4a,5,8a-tetrahydropyrimido[4,5-d]pyrimidine-2,7-dione
—— methyl (5E)-5-[(3-hydroxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate —— C14H13NO4
methyl (5E)-5-[(3-hydroxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate
—— 5,7-Diethyl-2-(4-hydroxyphenyl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C18H28N2O2+2
5,7-Diethyl-2-(4-hydroxyphenyl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— [(1S,3R)-3-methylcyclohexyl] (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H25BrN2O5
[(1S,3R)-3-methylcyclohexyl] (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-[(2R,5R)-2,5-dimethylthiolan-1-ium-1-yl]benzene-1,4-diol —— C12H17O2S+
2-[(2R,5R)-2,5-dimethylthiolan-1-ium-1-yl]benzene-1,4-diol
—— 2-(2-Hydroxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C20H32N2O2+2
2-(2-Hydroxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— 2-[(3R)-3-butylthian-1-ium-1-yl]benzene-1,4-diol —— C15H23O2S+
2-[(3R)-3-butylthian-1-ium-1-yl]benzene-1,4-diol
—— 5,7-Diethyl-2-(2-hydroxy-3-methoxyphenyl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C19H28N2O3+2
5,7-Diethyl-2-(2-hydroxy-3-methoxyphenyl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— [(2S)-2-methylpentyl] (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23N3O6
[(2S)-2-methylpentyl] (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (2E,5R)-2-(1-benzyl-2-oxoindol-3-ylidene)-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H27N3O6S
ethyl (2E,5R)-2-(1-benzyl-2-oxoindol-3-ylidene)-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[(2R,4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-3-ium-2-yl]phenol —— C17H20NO2+
2-[(2R,4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-3-ium-2-yl]phenol
—— ethyl (4R,5S,6S)-4-hydroxy-6-(4-hydroxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C14H15F3N2O4S
ethyl (4R,5S,6S)-4-hydroxy-6-(4-hydroxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one —— C17H15N3O3
6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one
—— 2-methoxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H20N2O6
2-methoxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (2R)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(2-hydroxyphenyl)acetonitrile —— C23H19N3O
(2R)-2-[(3S)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]-2-(2-hydroxyphenyl)acetonitrile
—— 2-[(5S)-3-phenyl-4,5-dihydro-1H-pyrazol-5-yl]phenol —— C15H14N2O
2-[(5S)-3-phenyl-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— 2,2-dimethoxyethyl-[(1R)-1-(3-hydroxy-4-methoxyphenyl)ethyl]azanium —— C13H22NO4+
2,2-dimethoxyethyl-[(1R)-1-(3-hydroxy-4-methoxyphenyl)ethyl]azanium
—— 2,2-dimethoxyethyl-[(1S)-1-(3-hydroxy-4-methoxyphenyl)ethyl]azanium —— C13H22NO4+
2,2-dimethoxyethyl-[(1S)-1-(3-hydroxy-4-methoxyphenyl)ethyl]azanium
—— methyl 2-[[(4S)-5-cyano-4-(4-hydroxy-3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanyl]acetate —— C15H13N3O6S
methyl 2-[[(4S)-5-cyano-4-(4-hydroxy-3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanyl]acetate
—— 4-(5,7-Dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl)benzene-1,2-diol —— C16H24N2O2+2
4-(5,7-Dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl)benzene-1,2-diol
—— 4-(5,7-Dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl)-2-methoxyphenol —— C17H26N2O2+2
4-(5,7-Dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl)-2-methoxyphenol
—— 3-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one —— C17H14BrNO3
3-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one
—— methyl (2S)-2-amino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C12H14F3NO5
methyl (2S)-2-amino-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— 3-[(5E)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C13H11NO4S2
3-[(5E)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— 4-[(2R)-2-chloro-1,1,2-trifluoro-2-(trifluoromethoxy)ethyl]sulfanylbenzene-1,3-diol —— C9H5ClF6O3S
4-[(2R)-2-chloro-1,1,2-trifluoro-2-(trifluoromethoxy)ethyl]sulfanylbenzene-1,3-diol
—— 4-[(2S)-2-chloro-1,1,2-trifluoro-2-(trifluoromethoxy)ethyl]sulfanylbenzene-1,3-diol —— C9H5ClF6O3S
4-[(2S)-2-chloro-1,1,2-trifluoro-2-(trifluoromethoxy)ethyl]sulfanylbenzene-1,3-diol
—— 2-(5-Morpholin-4-ium-4-ylpentylsulfanyl)benzene-1,4-diol —— C15H24NO3S+
2-(5-Morpholin-4-ium-4-ylpentylsulfanyl)benzene-1,4-diol
—— 6-[(R)-(2-hydroxy-3-methoxyphenyl)-morpholin-4-ylmethyl]-1,3-benzodioxol-5-ol —— C19H21NO6
6-[(R)-(2-hydroxy-3-methoxyphenyl)-morpholin-4-ylmethyl]-1,3-benzodioxol-5-ol
—— 2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetate —— C13H10NO5S2-
2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetate
—— 6-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyridin-2-ylamino)methyl]-1,3-benzodioxol-5-ol —— C21H20N2O6
6-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(pyridin-2-ylamino)methyl]-1,3-benzodioxol-5-ol
—— (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C11H10N2O3S
(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 2-{(5Z)-5-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-2,4-dioxo-1,3-thiazolidin-3-yl}-N-(4-methylphenyl)acetamide —— C23H22N2O5S
2-{(5Z)-5-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-2,4-dioxo-1,3-thiazolidin-3-yl}-N-(4-methylphenyl)acetamide