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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
—— tert-butyl N-[(R)-cyano-(4-hydroxyphenyl)methyl]-N-methylcarbamate —— C14H18N2O3
tert-butyl N-[(R)-cyano-(4-hydroxyphenyl)methyl]-N-methylcarbamate
—— (2S)-2-[(3-hydroxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile —— C14H16N2O3
(2S)-2-[(3-hydroxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile
—— (2S)-2-cyano-N-cyclopropyl-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C14H16N2O3
(2S)-2-cyano-N-cyclopropyl-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— (2R)-2-cyano-N-cyclopropyl-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C14H16N2O3
(2R)-2-cyano-N-cyclopropyl-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— (2R)-2-[(4-hydroxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile —— C14H16N2O3
(2R)-2-[(4-hydroxyphenyl)methyl]-3-morpholin-4-yl-3-oxopropanenitrile
—— (2S)-2-cyano-N-cyclopropyl-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C14H16N2O3
(2S)-2-cyano-N-cyclopropyl-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— 5-(4-ethoxyphenyl)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C31H29N3O6S
5-(4-ethoxyphenyl)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 4-[2-(2,6-Ditert-butylpyrylium-4-yl)ethenyl]-2-methoxyphenol —— C22H29O3+
4-[2-(2,6-Ditert-butylpyrylium-4-yl)ethenyl]-2-methoxyphenol
—— 4-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one —— C12H11NO4
4-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one
—— 4-[2-(4,6-Ditert-butylpyrylium-2-yl)ethenyl]-2-methoxyphenol —— C22H29O3+
4-[2-(4,6-Ditert-butylpyrylium-2-yl)ethenyl]-2-methoxyphenol
—— (2S)-2-cyano-N-cyclopentyl-3-(4-hydroxyphenyl)propanamide —— C15H18N2O2
(2S)-2-cyano-N-cyclopentyl-3-(4-hydroxyphenyl)propanamide
—— (2R)-2-cyano-N-cyclopentyl-3-(4-hydroxyphenyl)propanamide —— C15H18N2O2
(2R)-2-cyano-N-cyclopentyl-3-(4-hydroxyphenyl)propanamide
—— 4-bromo-2-[6-(4-ethylphenyl)-2-hexyl-2-methyl-3,4-dihydro-1H-pyrimidin-4-yl]phenol —— C25H33BrN2O
4-bromo-2-[6-(4-ethylphenyl)-2-hexyl-2-methyl-3,4-dihydro-1H-pyrimidin-4-yl]phenol
—— 4-Bromo-2-[2-(3-bromophenyl)-6-(4-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C24H23Br2N2O+
4-Bromo-2-[2-(3-bromophenyl)-6-(4-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-(2-methylpropyl)-3,4-dihydro-1H-pyrimidin-4-yl]phenol —— C23H29BrN2O
4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-(2-methylpropyl)-3,4-dihydro-1H-pyrimidin-4-yl]phenol
—— 4-Bromo-2-[2-(3-bromophenyl)-6-(4-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C24H22Br2N2O
4-Bromo-2-[2-(3-bromophenyl)-6-(4-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-propyl-3,4-dihydro-1H-pyrimidin-4-yl]phenol —— C22H27BrN2O
4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-propyl-3,4-dihydro-1H-pyrimidin-4-yl]phenol
—— 4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-(2-methylpropyl)-3,4-dihydro-1H-pyrimidin-3-ium-4-yl]phenol —— C23H30BrN2O+
4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-(2-methylpropyl)-3,4-dihydro-1H-pyrimidin-3-ium-4-yl]phenol
—— 4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-propyl-3,4-dihydro-1H-pyrimidin-3-ium-4-yl]phenol —— C22H28BrN2O+
4-bromo-2-[6-(4-ethylphenyl)-2-methyl-2-propyl-3,4-dihydro-1H-pyrimidin-3-ium-4-yl]phenol
—— 4-bromo-2-[6-(4-ethylphenyl)-2-hexyl-2-methyl-3,4-dihydro-1H-pyrimidin-3-ium-4-yl]phenol —— C25H34BrN2O+
4-bromo-2-[6-(4-ethylphenyl)-2-hexyl-2-methyl-3,4-dihydro-1H-pyrimidin-3-ium-4-yl]phenol
—— 3-bromo-N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H12Br2N2O3
3-bromo-N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— methyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C14H15BrN2O4S
methyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— N-[(1S)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]acetamide —— C11H14N2O3S
N-[(1S)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]acetamide
—— N-[(1R)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]acetamide —— C11H14N2O3S
N-[(1R)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]acetamide
—— N-[(1R)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]acetamide —— C11H14N2O3S
N-[(1R)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]acetamide
—— N-[(1S)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]acetamide —— C11H14N2O3S
N-[(1S)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]acetamide
—— 5-[(2R,5S)-3-ethyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C13H19NO4
5-[(2R,5S)-3-ethyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12ClNO3
5-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-1H-indol-2-one
—— 4-[(2R,5S)-3-ethyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C13H19NO4
4-[(2R,5S)-3-ethyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 3-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]phenol —— C14H21NO3
3-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]phenol
—— 4-[(2R,5R)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]phenol —— C14H21NO3
4-[(2R,5R)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]phenol
—— 4-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]phenol —— C14H21NO3
4-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]phenol
—— 2-(6-Methylheptyl)benzene-1,4-diol —— C14H22O2
2-(6-Methylheptyl)benzene-1,4-diol
—— Propan-2-yl 4-(4-hydroxy-3-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C15H17N3O6
Propan-2-yl 4-(4-hydroxy-3-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— (2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N,N-dimethylpropanamide —— C13H16N2O3
(2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N,N-dimethylpropanamide
—— 4-[(2-hydroxy-5-nitrophenyl)-[3-methyl-1-(4-methylphenyl)-5-oxo-4H-pyrazol-4-yl]methyl]-5-methyl-2-(4-methylphenyl)-4H-pyrazol-3-one —— C29H27N5O5
4-[(2-hydroxy-5-nitrophenyl)-[3-methyl-1-(4-methylphenyl)-5-oxo-4H-pyrazol-4-yl]methyl]-5-methyl-2-(4-methylphenyl)-4H-pyrazol-3-one
—— tert-butyl N-[(S)-cyano-(4-hydroxyphenyl)methyl]carbamate —— C13H16N2O3
tert-butyl N-[(S)-cyano-(4-hydroxyphenyl)methyl]carbamate
—— (2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N,N-dimethylpropanamide —— C13H16N2O3
(2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N,N-dimethylpropanamide
—— tert-butyl N-[(S)-cyano-(3-hydroxyphenyl)methyl]carbamate —— C13H16N2O3
tert-butyl N-[(S)-cyano-(3-hydroxyphenyl)methyl]carbamate
—— 2-(1,3-Benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enal —— C16H11N3O5
2-(1,3-Benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enal
—— N-[1-(4-cyclohexylphenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C21H24N2O4
N-[1-(4-cyclohexylphenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— (2S)-N-tert-butyl-2-cyano-3-(4-hydroxyphenyl)propanamide —— C14H18N2O2
(2S)-N-tert-butyl-2-cyano-3-(4-hydroxyphenyl)propanamide
—— (2S)-2-cyano-3-(4-hydroxyphenyl)-N-(2-methylpropyl)propanamide —— C14H18N2O2
(2S)-2-cyano-3-(4-hydroxyphenyl)-N-(2-methylpropyl)propanamide
—— (2S)-2-cyano-3-(3-hydroxyphenyl)-N-(2-methylpropyl)propanamide —— C14H18N2O2
(2S)-2-cyano-3-(3-hydroxyphenyl)-N-(2-methylpropyl)propanamide
—— (2S)-N-tert-butyl-2-cyano-3-(3-hydroxyphenyl)propanamide —— C14H18N2O2
(2S)-N-tert-butyl-2-cyano-3-(3-hydroxyphenyl)propanamide
—— (2R)-2-cyano-3-(4-hydroxyphenyl)-N-(2-methylpropyl)propanamide —— C14H18N2O2
(2R)-2-cyano-3-(4-hydroxyphenyl)-N-(2-methylpropyl)propanamide
—— (2R)-N-tert-butyl-2-cyano-3-(4-hydroxyphenyl)propanamide —— C14H18N2O2
(2R)-N-tert-butyl-2-cyano-3-(4-hydroxyphenyl)propanamide
—— N-(cycloheptylideneamino)-3,4,5-trihydroxybenzamide —— C14H18N2O4
N-(cycloheptylideneamino)-3,4,5-trihydroxybenzamide
—— 2-[(E)-[(4-Amino-1,2,5-oxadiazol-3-YL)imino]methyl]-4,6-diiodophenol —— C9H6I2N4O2
2-[(E)-[(4-Amino-1,2,5-oxadiazol-3-YL)imino]methyl]-4,6-diiodophenol
—— 5-[(2R,5S)-5-(hydroxymethyl)-3-methyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C12H17NO4
5-[(2R,5S)-5-(hydroxymethyl)-3-methyl-1,3-oxazolidin-2-yl]-2-methoxyphenol