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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
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-(3-methylsulfanylphenyl)imino-1,3-thiazolidin-4-one —— C19H18N2O3S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-(3-methylsulfanylphenyl)imino-1,3-thiazolidin-4-one
—— (2S)-3-(benzimidazol-1-yl)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylpropanamide —— C19H20N4O3
(2S)-3-(benzimidazol-1-yl)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylpropanamide
—— 4-[(1R,2R,5S,6R,9S)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C17H22O2
4-[(1R,2R,5S,6R,9S)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— 4-[(1R,2R,5S,6S,9R)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C17H22O2
4-[(1R,2R,5S,6S,9R)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— 4-[(1R,2R,5S,6S,9S)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C17H22O2
4-[(1R,2R,5S,6S,9S)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methyl-1,3-thiazol-4-yl)acetamide —— C14H14BrN3O3S
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methyl-1,3-thiazol-4-yl)acetamide
—— (5E)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylideneimidazolidin-4-one —— C16H13BrN2O4S
(5E)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylideneimidazolidin-4-one
—— (5E)-3-(furan-2-ylmethyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C16H14N2O4S
(5E)-3-(furan-2-ylmethyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5E)-3-cyclohexyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C17H20N2O3S
(5E)-3-cyclohexyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (E)-3-[5-chloro-3-methyl-1-(2-methylpropyl)pyrazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C18H21ClN2O3
(E)-3-[5-chloro-3-methyl-1-(2-methylpropyl)pyrazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— ethyl (2Z)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-ylidene]acetate —— C16H17NO5S2
ethyl (2Z)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-ylidene]acetate
—— 3-[(Z)-2-chloro-2-(5-phenyl-1,3,4-oxadiazol-2-yl)ethenyl]phenol —— C16H11ClN2O2
3-[(Z)-2-chloro-2-(5-phenyl-1,3,4-oxadiazol-2-yl)ethenyl]phenol
—— 5-[(Z)-2-chloro-2-(5-phenyl-1,3,4-oxadiazol-2-yl)ethenyl]-2-methoxyphenol —— C17H13ClN2O3
5-[(Z)-2-chloro-2-(5-phenyl-1,3,4-oxadiazol-2-yl)ethenyl]-2-methoxyphenol
—— 4-[(E)-3-[(3R)-3-(2-hydroxyethyl)-4-[(6-methylpyridin-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C23H31N3O3
4-[(E)-3-[(3R)-3-(2-hydroxyethyl)-4-[(6-methylpyridin-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— 4-[(E)-3-[(3R)-3-(2-hydroxyethyl)-4-[(5-methylfuran-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C22H30N2O4
4-[(E)-3-[(3R)-3-(2-hydroxyethyl)-4-[(5-methylfuran-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— 2-(4-bromo-2-fluorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H13BrFNO4
2-(4-bromo-2-fluorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 3-tert-butyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C14H18N4O2S
3-tert-butyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea —— C13H17N3O2S
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea
—— 2-(4-Methoxyphenyl)ethyl 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate —— C17H18N4O3
2-(4-Methoxyphenyl)ethyl 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate
—— (Z)-3-(2-hydroxy-5-methylanilino)-1-(5-methylfuran-2-yl)but-2-en-1-one —— C16H17NO3
(Z)-3-(2-hydroxy-5-methylanilino)-1-(5-methylfuran-2-yl)but-2-en-1-one
—— 4-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol —— C19H30N2O2
4-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol
—— 2-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-6-methoxyphenol —— C19H30N2O2
2-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-6-methoxyphenol
—— 4-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol —— C19H30N2O2
4-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol
—— 5-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol —— C19H30N2O2
5-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol
—— 2-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-5-methoxyphenol —— C19H30N2O2
2-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-5-methoxyphenol
—— 2-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-5-methoxyphenol —— C19H30N2O2
2-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-5-methoxyphenol
—— 5-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol —— C19H30N2O2
5-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-2-methoxyphenol
—— 2-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-6-methoxyphenol —— C19H30N2O2
2-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]-6-methoxyphenol
—— 4-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]benzene-1,3-diol —— C18H28N2O2
4-[(1R)-2-amino-1-[(1S,5S)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]benzene-1,3-diol
—— 4-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]benzene-1,3-diol —— C18H28N2O2
4-[(1R)-2-amino-1-[(1R,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl]ethyl]benzene-1,3-diol
—— (Z)-1-(furan-2-yl)-3-(2-hydroxy-4-methylanilino)prop-2-en-1-one —— C14H13NO3
(Z)-1-(furan-2-yl)-3-(2-hydroxy-4-methylanilino)prop-2-en-1-one
—— (5Z)-3-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C15H18N2O3S
(5Z)-3-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methylpropyl)-2-sulfanylideneimidazolidin-4-one —— C15H17ClN2O3S
(5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methylpropyl)-2-sulfanylideneimidazolidin-4-one
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one —— C14H15ClN2O3S
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one
—— (5Z)-3-butyl-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C15H18N2O3S
(5Z)-3-butyl-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5E)-3-benzyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C18H16N2O3S
(5E)-3-benzyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5E)-3-(furan-2-ylmethyl)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C16H14N2O4S
(5E)-3-(furan-2-ylmethyl)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one —— C14H16N2O3S
(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one
—— (5E)-3-[(2-chlorophenyl)methyl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C18H15ClN2O3S
(5E)-3-[(2-chlorophenyl)methyl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-2-sulfanylideneimidazolidin-4-one —— C15H18N2O3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-2-sulfanylideneimidazolidin-4-one
—— (2Z,7R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-6,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-3,5-dione —— C15H14N2O4S
(2Z,7R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-6,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-3,5-dione
—— (2Z,7S)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-6,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-3,5-dione —— C15H14N2O4S
(2Z,7S)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-6,7-dihydro-[1,3]thiazolo[3,2-a]pyrimidine-3,5-dione
—— 4-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-thione —— C10H7F3N4OS
4-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-thione
—— (2R)-N-(2-hydroxy-4-nitrophenyl)-2-(3-methylphenoxy)propanamide —— C16H16N2O5
(2R)-N-(2-hydroxy-4-nitrophenyl)-2-(3-methylphenoxy)propanamide
—— (5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-[4-(dimethylamino)phenyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15ClN2O3S2
(5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-[4-(dimethylamino)phenyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (E)-2-(4-bromophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile —— C16H12BrNO4S
(E)-2-(4-bromophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— (E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(3-methylthiophen-2-yl)prop-2-enamide —— C18H13N3O3S2
(E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(3-methylthiophen-2-yl)prop-2-enamide
—— 2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol —— C20H27N3O5S
2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol
—— N-(2-hydroxy-5-nitrophenyl)-2-[(3-methylphenyl)methylsulfanyl]acetamide —— C16H16N2O4S
N-(2-hydroxy-5-nitrophenyl)-2-[(3-methylphenyl)methylsulfanyl]acetamide
—— 2-[(2-chlorophenyl)methylsulfanyl]-N-(2-hydroxy-4-nitrophenyl)acetamide —— C15H13ClN2O4S
2-[(2-chlorophenyl)methylsulfanyl]-N-(2-hydroxy-4-nitrophenyl)acetamide