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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
—— (4R)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-propan-2-yl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C18H21N3O3
(4R)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-propan-2-yl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— 4-methyl-2-[[(2S)-pyrrolidin-2-yl]methyl]phenol —— C12H17NO
4-methyl-2-[[(2S)-pyrrolidin-2-yl]methyl]phenol
—— 4-methyl-2-[[(2R)-pyrrolidin-2-yl]methyl]phenol —— C12H17NO
4-methyl-2-[[(2R)-pyrrolidin-2-yl]methyl]phenol
—— 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,3-diol —— C9H13NO3
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,3-diol
—— 2-[(Z)-3-[4-[4-(aminomethyl)triazol-1-yl]piperidin-1-yl]-2-methylprop-1-enyl]-4-chlorophenol —— C18H24ClN5O
2-[(Z)-3-[4-[4-(aminomethyl)triazol-1-yl]piperidin-1-yl]-2-methylprop-1-enyl]-4-chlorophenol
—— 4-[(1R)-3-amino-1-hydroxypropyl]benzene-1,3-diol —— C9H13NO3
4-[(1R)-3-amino-1-hydroxypropyl]benzene-1,3-diol
—— 4-[(1S)-3-amino-1-hydroxypropyl]benzene-1,3-diol —— C9H13NO3
4-[(1S)-3-amino-1-hydroxypropyl]benzene-1,3-diol
—— 4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,3-diol —— C9H13NO3
4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,3-diol
—— N-hydroxy-N-[(4-hydroxyphenyl)methyl]acetamide —— C9H11NO3
N-hydroxy-N-[(4-hydroxyphenyl)methyl]acetamide
—— N-hydroxy-N-[(2-hydroxyphenyl)methyl]acetamide —— C9H11NO3
N-hydroxy-N-[(2-hydroxyphenyl)methyl]acetamide
—— N-hydroxy-N-[(3-hydroxyphenyl)methyl]acetamide —— C9H11NO3
N-hydroxy-N-[(3-hydroxyphenyl)methyl]acetamide
—— 2-[(1S)-1-aminoethyl]-4,5-dimethylphenol —— C10H15NO
2-[(1S)-1-aminoethyl]-4,5-dimethylphenol
—— 4-[(2S)-4-aminobutan-2-yl]phenol —— C10H15NO
4-[(2S)-4-aminobutan-2-yl]phenol
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(3-morpholin-4-ium-4-ylpropyl)thiourea —— C16H25N4O3S+
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(3-morpholin-4-ium-4-ylpropyl)thiourea
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea —— C14H19N3O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea
—— 4-[(Z)-3-[(3S)-3-(1,3-benzodioxol-5-ylamino)piperidin-1-yl]prop-1-enyl]-2-methoxyphenol —— C22H26N2O4
4-[(Z)-3-[(3S)-3-(1,3-benzodioxol-5-ylamino)piperidin-1-yl]prop-1-enyl]-2-methoxyphenol
—— (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-6,7-dimethoxy-1H-isochromen-3-one —— C19H18O6
(4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-6,7-dimethoxy-1H-isochromen-3-one
—— (3Z)-1-benzyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]indol-2-one —— C23H19N3O3
(3Z)-1-benzyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]indol-2-one
—— (4S)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-phenyl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C21H19N3O3
(4S)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-phenyl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-phenyl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C21H19N3O3
(4R)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-phenyl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (1S,5S,7S)-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[(2-methylphenyl)methyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one —— C26H30N2O3
(1S,5S,7S)-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[(2-methylphenyl)methyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one
—— (2Z)-2-[(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-4,4-dimethyl-3-oxopentanenitrile —— C19H19BrN2O4S
(2Z)-2-[(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-4,4-dimethyl-3-oxopentanenitrile
—— (2E)-2-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-4,4-dimethyl-3-oxopentanenitrile —— C19H19BrN2O4S
(2E)-2-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-4,4-dimethyl-3-oxopentanenitrile
—— (Z)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C14H11BrN2O2S
(Z)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
—— (Z)-3-(3-hydroxy-4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C14H12N2O2S
(Z)-3-(3-hydroxy-4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
—— 2-methoxy-4-[(Z)-3-[[(3R)-1-pyrimidin-2-ylpiperidin-3-yl]amino]prop-1-enyl]phenol —— C19H24N4O2
2-methoxy-4-[(Z)-3-[[(3R)-1-pyrimidin-2-ylpiperidin-3-yl]amino]prop-1-enyl]phenol
—— 2-methoxy-4-[(Z)-3-[[(3S)-1-pyrimidin-2-ylpiperidin-3-yl]amino]prop-1-enyl]phenol —— C19H24N4O2
2-methoxy-4-[(Z)-3-[[(3S)-1-pyrimidin-2-ylpiperidin-3-yl]amino]prop-1-enyl]phenol
—— N-[[(3R)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]methyl]acetamide —— C18H25ClN2O2
N-[[(3R)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]methyl]acetamide
—— (4S)-3-(furan-2-yl)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C19H17N3O4
(4S)-3-(furan-2-yl)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4R)-3-(furan-2-yl)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C19H17N3O4
(4R)-3-(furan-2-yl)-4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (E)-2-[4-(1-adamantyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C23H24N2O2S
(E)-2-[4-(1-adamantyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 4-[(Z)-3-[(3R)-4-benzyl-3-(2-hydroxyethyl)piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C23H30N2O3
4-[(Z)-3-[(3R)-4-benzyl-3-(2-hydroxyethyl)piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— (5Z)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C16H10FN3O4S
(5Z)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— (3E)-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one —— C18H17NO5
(3E)-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one
—— (Z)-1-(4-hydroxy-3-methoxyphenyl)-3-(1-methylpyrazol-4-yl)prop-2-en-1-one —— C14H14N2O3
(Z)-1-(4-hydroxy-3-methoxyphenyl)-3-(1-methylpyrazol-4-yl)prop-2-en-1-one
—— 4-[(Z)-3-[(3S)-3-(2-hydroxyethyl)-4-[(6-methylpyridin-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C23H31N3O3
4-[(Z)-3-[(3S)-3-(2-hydroxyethyl)-4-[(6-methylpyridin-2-yl)methyl]piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— 2-methoxy-4-[(Z)-3-[(3S)-3-morpholin-4-ylpiperidin-1-yl]prop-1-enyl]phenol —— C19H28N2O3
2-methoxy-4-[(Z)-3-[(3S)-3-morpholin-4-ylpiperidin-1-yl]prop-1-enyl]phenol
—— (1S,5S,7S)-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[(2-methoxyphenyl)methyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one —— C26H30N2O4
(1S,5S,7S)-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[(2-methoxyphenyl)methyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one
—— (5E)-5-[(2-bromo-5-hydroxyphenyl)methylidene]-2-(3-chloro-2-methylphenyl)imino-1,3-thiazolidin-4-one —— C17H12BrClN2O2S
(5E)-5-[(2-bromo-5-hydroxyphenyl)methylidene]-2-(3-chloro-2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3-chloro-2-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H14BrClN2O3S
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3-chloro-2-methylphenyl)imino-1,3-thiazolidin-4-one
—— 4-chloro-2-[(Z)-3-[(6R)-6-[(dimethylamino)methyl]-1,4-oxazepan-4-yl]-2-methylprop-1-enyl]phenol —— C18H27ClN2O2
4-chloro-2-[(Z)-3-[(6R)-6-[(dimethylamino)methyl]-1,4-oxazepan-4-yl]-2-methylprop-1-enyl]phenol
—— 4-[(Z)-3-[(3S)-3-(2-hydroxyethyl)-4-propan-2-ylpiperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C19H30N2O3
4-[(Z)-3-[(3S)-3-(2-hydroxyethyl)-4-propan-2-ylpiperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— 2-methoxy-6-[[2-methoxyethyl-[(Z)-3-phenylprop-2-enyl]amino]methyl]phenol —— C20H25NO3
2-methoxy-6-[[2-methoxyethyl-[(Z)-3-phenylprop-2-enyl]amino]methyl]phenol
—— 4-[(Z)-3-[(3R)-3-[ethyl(pyridin-4-ylmethyl)amino]piperidin-1-yl]prop-1-enyl]-2-methoxyphenol —— C23H31N3O2
4-[(Z)-3-[(3R)-3-[ethyl(pyridin-4-ylmethyl)amino]piperidin-1-yl]prop-1-enyl]-2-methoxyphenol
—— 4-[(Z)-3-[4-(hydroxymethyl)-4-[[(2S)-oxan-2-yl]methyl]piperidin-1-yl]prop-1-enyl]-2-methoxyphenol —— C22H33NO4
4-[(Z)-3-[4-(hydroxymethyl)-4-[[(2S)-oxan-2-yl]methyl]piperidin-1-yl]prop-1-enyl]-2-methoxyphenol
—— N-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2-[1-(thiophen-2-ylmethyl)tetrazol-5-yl]sulfanylacetamide —— C17H19N5O2S2
N-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2-[1-(thiophen-2-ylmethyl)tetrazol-5-yl]sulfanylacetamide
—— 4-[(Z)-3-[4-(hydroxymethyl)-4-[[(2R)-oxan-2-yl]methyl]piperidin-1-yl]prop-1-enyl]-2-methoxyphenol —— C22H33NO4
4-[(Z)-3-[4-(hydroxymethyl)-4-[[(2R)-oxan-2-yl]methyl]piperidin-1-yl]prop-1-enyl]-2-methoxyphenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylfuran-3-carboxamide —— C14H13BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylfuran-3-carboxamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-methoxybenzamide —— C16H15BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-methoxybenzamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-chlorophenoxy)acetamide —— C16H14BrClN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-chlorophenoxy)acetamide