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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)-2-(4-ethylpiperazin-4-ium-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H22N3O3S+
(5Z)-2-(4-ethylpiperazin-4-ium-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (3S)-3-(4-hydroxy-3-methoxyphenyl)-4,4-dimethyl-2-oxaspiro[5.5]undecane-1,5-dione —— C19H24O5
(3S)-3-(4-hydroxy-3-methoxyphenyl)-4,4-dimethyl-2-oxaspiro[5.5]undecane-1,5-dione
—— (5E)-2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5E)-2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5E)-2-(4-ethylpiperazin-4-ium-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H22N3O3S+
(5E)-2-(4-ethylpiperazin-4-ium-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C11H9ClN2O3S
(5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (3R,4S)-6-amino-4-(3-hydroxy-4-methoxyphenyl)-2-imino-3,4-dihydrothiopyran-3,5-dicarbonitrile —— C14H12N4O2S
(3R,4S)-6-amino-4-(3-hydroxy-4-methoxyphenyl)-2-imino-3,4-dihydrothiopyran-3,5-dicarbonitrile
—— prop-2-enyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H15N3O6
prop-2-enyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— prop-2-enyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H15N3O6
prop-2-enyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 3-hydroxy-4-nitro-N-[(2R)-1-(2,2,2-trifluoroethoxy)propan-2-yl]benzamide —— C12H13F3N2O5
3-hydroxy-4-nitro-N-[(2R)-1-(2,2,2-trifluoroethoxy)propan-2-yl]benzamide
—— (9aR)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]-8-methyl-1,3,4,6,7,9a-hexahydropyrazino[1,2-a]pyrazin-9-one —— C19H27N3O3
(9aR)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]-8-methyl-1,3,4,6,7,9a-hexahydropyrazino[1,2-a]pyrazin-9-one
—— 1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-prop-2-enylurea —— C13H18N2O2
1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-prop-2-enylurea
—— 1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-prop-2-ynylurea —— C13H16N2O2
1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-prop-2-ynylurea
—— 1-[(1R)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-prop-2-ynylurea —— C13H16N2O2
1-[(1R)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-prop-2-ynylurea
—— 1-[(1R)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-(pyridin-3-ylmethyl)urea —— C16H19N3O2
1-[(1R)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-(pyridin-3-ylmethyl)urea
—— 1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-(pyridin-3-ylmethyl)urea —— C16H19N3O2
1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methyl-3-(pyridin-3-ylmethyl)urea
—— 2-methylsulfanylethyl (4S)-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H20N2O5S
2-methylsulfanylethyl (4S)-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (2R)-2-(2-hydroxy-3-methoxyphenyl)-2-(5-phenyl-3,4-dihydropyrazol-2-yl)acetonitrile —— C18H17N3O2
(2R)-2-(2-hydroxy-3-methoxyphenyl)-2-(5-phenyl-3,4-dihydropyrazol-2-yl)acetonitrile
—— (2R)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)propanamide —— C18H18N5O4-
(2R)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)propanamide
—— (2S)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)propanamide —— C18H18N5O4-
(2S)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)propanamide
—— (2S)-2-(2-hydroxy-3-methoxyphenyl)-2-(5-phenyl-3,4-dihydropyrazol-2-yl)acetonitrile —— C18H17N3O2
(2S)-2-(2-hydroxy-3-methoxyphenyl)-2-(5-phenyl-3,4-dihydropyrazol-2-yl)acetonitrile
—— 3-(2-tert-butylpyrimidin-5-yl)-1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methylurea —— C18H24N4O2
3-(2-tert-butylpyrimidin-5-yl)-1-[(1S)-1-(3-hydroxyphenyl)ethyl]-1-methylurea
—— 3-(2-tert-butylpyrimidin-5-yl)-1-[(1R)-1-(3-hydroxyphenyl)ethyl]-1-methylurea —— C18H24N4O2
3-(2-tert-butylpyrimidin-5-yl)-1-[(1R)-1-(3-hydroxyphenyl)ethyl]-1-methylurea
—— methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-2-methylphenyl)propanoate —— C11H11F3O4
methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-2-methylphenyl)propanoate
—— ethyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)propanoate —— C12H13F3O5
ethyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)propanoate
—— methyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-2,3-dimethylphenyl)propanoate —— C12H13F3O4
methyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-2,3-dimethylphenyl)propanoate
—— (3-Hydroxy-4-methoxyphenyl)methyl-methylazanium —— C9H14NO2+
(3-Hydroxy-4-methoxyphenyl)methyl-methylazanium
—— hexyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H28N2O6
hexyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— hexyl (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H28N2O6
hexyl (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 3-methoxy-2-[(4S)-5-(3-methylsulfanylpropyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]phenol —— C17H23N3O2S
3-methoxy-2-[(4S)-5-(3-methylsulfanylpropyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]phenol
—— N-[[(3R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-2,2-dimethylpropanamide —— C18H28N2O3
N-[[(3R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]pyrrolidin-3-yl]methyl]-2,2-dimethylpropanamide
—— 3-methoxy-2-[(4R)-5-(3-methylsulfanylpropyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]phenol —— C17H23N3O2S
3-methoxy-2-[(4R)-5-(3-methylsulfanylpropyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]phenol
—— 4-[(4R)-5-[(1-ethyl-3,5-dimethylpyrazol-4-yl)methyl]-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]-2-methoxyphenol —— C21H27N5O2
4-[(4R)-5-[(1-ethyl-3,5-dimethylpyrazol-4-yl)methyl]-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl]-2-methoxyphenol
—— 5-[[[(1R)-1-[4-(2-hydroxyethoxy)-3-methoxyphenyl]ethyl]amino]methyl]-2-methoxyphenol —— C19H25NO5
5-[[[(1R)-1-[4-(2-hydroxyethoxy)-3-methoxyphenyl]ethyl]amino]methyl]-2-methoxyphenol
—— 1-hydroxy-3-[(1R)-1-[methyl(sulfamoyl)amino]ethyl]benzene —— C9H14N2O3S
1-hydroxy-3-[(1R)-1-[methyl(sulfamoyl)amino]ethyl]benzene
—— 1-hydroxy-3-[(1S)-1-[methyl(sulfamoyl)amino]ethyl]benzene —— C9H14N2O3S
1-hydroxy-3-[(1S)-1-[methyl(sulfamoyl)amino]ethyl]benzene
—— 1-cyclopropyl-3-[(2S)-2-(dimethylamino)-2-phenylethyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C22H29N3O3
1-cyclopropyl-3-[(2S)-2-(dimethylamino)-2-phenylethyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 1-cyclopropyl-3-[(2R)-2-(dimethylamino)-2-phenylethyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C22H29N3O3
1-cyclopropyl-3-[(2R)-2-(dimethylamino)-2-phenylethyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 1-cyclopropyl-3-[(1S,2R,3R)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C20H30N2O3
1-cyclopropyl-3-[(1S,2R,3R)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 1-cyclopropyl-3-[(1R,2R,3R)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C20H30N2O3
1-cyclopropyl-3-[(1R,2R,3R)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 1-cyclopropyl-3-[(1S,2R,3S)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C20H30N2O3
1-cyclopropyl-3-[(1S,2R,3S)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 1-cyclopropyl-3-[(1R,2R,3S)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C20H30N2O3
1-cyclopropyl-3-[(1R,2R,3S)-2,3-dimethylcyclohexyl]-1-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 2-[(3R)-3-methylthian-1-ium-1-yl]benzene-1,4-diol —— C12H17O2S+
2-[(3R)-3-methylthian-1-ium-1-yl]benzene-1,4-diol
—— (2R,7S)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2R,7S)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7S)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2R,7S)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R)-2-(4-hydroxy-3-methoxyphenyl)-5-phenyl-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one —— C19H16N2O3S
(2R)-2-(4-hydroxy-3-methoxyphenyl)-5-phenyl-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one
—— (2S,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H20N2O3S
(2S,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7R)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2S,7R)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7R)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2R,7R)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7R)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2R,7R)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one