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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
—— (2-Hydroxy-6-nitrophenyl)methyl-dimethylazanium —— C9H13N2O3+
(2-Hydroxy-6-nitrophenyl)methyl-dimethylazanium
—— 3-[5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C14H11BrNO5S2-
3-[5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
—— 2-(1H-benzimidazol-2-yl)-3-(3-bromo-2-hydroxy-5-nitrophenyl)prop-2-enenitrile —— C16H9BrN4O3
2-(1H-benzimidazol-2-yl)-3-(3-bromo-2-hydroxy-5-nitrophenyl)prop-2-enenitrile
—— 7-ethenyl-8-(3-hydroxy-4-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O4
7-ethenyl-8-(3-hydroxy-4-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— N-[(1R)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide —— C12H16N2O3S
N-[(1R)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide
—— 5-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-imino-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-thiazolidin-4-one —— C14H10Br2N4O3S2
5-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-imino-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-thiazolidin-4-one
—— N-[(1R)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide —— C12H16N2O3S
N-[(1R)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide
—— 3,4,5-trihydroxy-N-[(2-nitrophenyl)methylideneamino]benzamide —— C14H11N3O6
3,4,5-trihydroxy-N-[(2-nitrophenyl)methylideneamino]benzamide
—— N-[(1S)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide —— C12H16N2O3S
N-[(1S)-2-amino-1-(4-hydroxy-3-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide
—— N-[(1S)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide —— C12H16N2O3S
N-[(1S)-2-amino-1-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneethyl]-N-methylacetamide
—— 4-[(2R,5S)-5-(hydroxymethyl)-3-propyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H21NO4
4-[(2R,5S)-5-(hydroxymethyl)-3-propyl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-[(2R,5S)-5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H21NO4
5-[(2R,5S)-5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-[(2R,5R)-5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H21NO4
5-[(2R,5R)-5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 4-[(2R,5S)-5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H21NO4
4-[(2R,5S)-5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-[(2R,5R)-5-(hydroxymethyl)-3-propyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H21NO4
5-[(2R,5R)-5-(hydroxymethyl)-3-propyl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-[(2R,5S)-5-(hydroxymethyl)-3-propyl-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H21NO4
5-[(2R,5S)-5-(hydroxymethyl)-3-propyl-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 6-Ethenyl-5-(2-hydroxy-3-prop-2-enylphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C25H28O3
6-Ethenyl-5-(2-hydroxy-3-prop-2-enylphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— 4-(3-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 67439-09-2 C15H13N3O
4-(3-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile
—— N-(2-hydroxy-5-nitrophenyl)-2,2,3,3-tetramethylcyclopropane-1-carboxamide —— C14H18N2O4
N-(2-hydroxy-5-nitrophenyl)-2,2,3,3-tetramethylcyclopropane-1-carboxamide
—— 5-[4-(3-Hydroxypropyl)-1,3-thiazol-2-yl]-2-methoxyphenol —— C13H15NO3S
5-[4-(3-Hydroxypropyl)-1,3-thiazol-2-yl]-2-methoxyphenol
—— 5-[(2R,5R)-3-cyclopropyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H19NO4
5-[(2R,5R)-3-cyclopropyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 4-[(2R,5R)-3-cyclopropyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H19NO4
4-[(2R,5R)-3-cyclopropyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-[(2S,5R)-3-cyclopropyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C14H19NO4
5-[(2S,5R)-3-cyclopropyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 2-{(E)-[(5-chloro-2,4-dimethoxyphenyl)imino]methyl}-6-methoxyphenol —— C16H16ClNO4
2-{(E)-[(5-chloro-2,4-dimethoxyphenyl)imino]methyl}-6-methoxyphenol
—— (3R)-1-[(4-hydroxy-3-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylic acid —— C13H15NO5
(3R)-1-[(4-hydroxy-3-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylic acid
—— 7-ethenyl-8-(2-hydroxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H20O3
7-ethenyl-8-(2-hydroxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— ethyl 5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl 5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]phenol —— C15H21NO3
3-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]phenol
—— 4-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]phenol —— C15H21NO3
4-[(2R,5R)-3-cyclopentyl-5-(hydroxymethyl)-1,3-oxazolidin-2-yl]phenol
—— 4-Bromo-2-[2-(4-bromophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18Br2ClN2O+
4-Bromo-2-[2-(4-bromophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Bromo-2-[2-(4-bromophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17Br2ClN2O
4-Bromo-2-[2-(4-bromophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Bromo-2-[6-(3-bromophenyl)-2-(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18Br3N2O+
4-Bromo-2-[6-(3-bromophenyl)-2-(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 2-[2,6-Bis(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-bromophenol —— C22H17Br3N2O
2-[2,6-Bis(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-bromophenol
—— 4-Bromo-2-[6-(3-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17Br2ClN2O
4-Bromo-2-[6-(3-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Bromo-2-[6-(4-bromophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18Br2FN2O+
4-Bromo-2-[6-(4-bromophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 2-(3,5-Ditert-butyl-4-hydroxyphenyl)ethyl 3-{[5-(3,5-ditert-butyl-4-hydroxyphenyl)-3-oxopentyl]oxy}propanoate —— C38H58O6
2-(3,5-Ditert-butyl-4-hydroxyphenyl)ethyl 3-{[5-(3,5-ditert-butyl-4-hydroxyphenyl)-3-oxopentyl]oxy}propanoate
—— 4-Bromo-2-[6-(3-bromophenyl)-2-(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17Br3N2O
4-Bromo-2-[6-(3-bromophenyl)-2-(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Bromo-2-[6-(3-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18Br2ClN2O+
4-Bromo-2-[6-(3-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 2-[2,6-Bis(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-bromophenol —— C22H18Br3N2O+
2-[2,6-Bis(4-bromophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-bromophenol
—— 2-(4-Hydroxy-3-methoxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C17H24N2O3+2
2-(4-Hydroxy-3-methoxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 4-Bromo-2-[6-(4-bromophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17Br2FN2O
4-Bromo-2-[6-(4-bromophenyl)-2-(2-fluorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 3-[(5-Bromo-2-hydroxyphenyl)methylidene]-5-(4-fluorophenyl)furan-2-one —— C17H10BrFO3
3-[(5-Bromo-2-hydroxyphenyl)methylidene]-5-(4-fluorophenyl)furan-2-one
—— (2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-propan-2-ylpropanamide —— C14H18N2O3
(2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-propan-2-ylpropanamide
—— tert-butyl N-[(S)-cyano-(4-hydroxyphenyl)methyl]-N-methylcarbamate —— C14H18N2O3
tert-butyl N-[(S)-cyano-(4-hydroxyphenyl)methyl]-N-methylcarbamate
—— (2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-propylpropanamide —— C14H18N2O3
(2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-propylpropanamide
—— (2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-propan-2-ylpropanamide —— C14H18N2O3
(2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-propan-2-ylpropanamide
—— tert-butyl N-[(R)-cyano-(3-hydroxyphenyl)methyl]-N-methylcarbamate —— C14H18N2O3
tert-butyl N-[(R)-cyano-(3-hydroxyphenyl)methyl]-N-methylcarbamate
—— 5-[(3-Bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-(4-ethylphenyl)-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one —— C26H22BrN3O4S
5-[(3-Bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-(4-ethylphenyl)-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (2S)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-propan-2-ylpropanamide —— C14H18N2O3
(2S)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-propan-2-ylpropanamide
—— (2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-propan-2-ylpropanamide —— C14H18N2O3
(2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-propan-2-ylpropanamide