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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
—— N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)acetohydrazide —— C15H18N4O4
N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-(3-methyl-5-oxo-1,2-dihydropyrazol-4-yl)acetohydrazide
—— 2-(2-hydroxy-4-methoxyphenyl)-2-oxo-N-phenylacetamide —— C15H13NO4
2-(2-hydroxy-4-methoxyphenyl)-2-oxo-N-phenylacetamide
—— 5-(4-hydroxy-3-nitrobenzylidene)-3-(3,4-dichlorobenzyl)-thiazolidine-2,4-dione —— C17H10Cl2N2O5S
5-(4-hydroxy-3-nitrobenzylidene)-3-(3,4-dichlorobenzyl)-thiazolidine-2,4-dione
—— 4-chloro-2-({(E)-1-[5-(4-fluorophenyl)-2-furyl]methylidene}amino)phenol —— C17H11ClFNO2
4-chloro-2-({(E)-1-[5-(4-fluorophenyl)-2-furyl]methylidene}amino)phenol
—— 5,7-Dibromo-4-hydroxy-1,3-benzoxathiol-2-one —— C7H2Br2O3S
5,7-Dibromo-4-hydroxy-1,3-benzoxathiol-2-one
—— 4-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]benzene-1,3-diol —— C9H10N6O2
4-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]benzene-1,3-diol
—— 3-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]phenol —— C9H10N6O
3-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]phenol
—— 5-[(2R,5R)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C15H23NO4
5-[(2R,5R)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 5-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C15H23NO4
5-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 4-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C15H23NO4
4-[(2R,5S)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— 2-(1,3-Benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enenitrile —— C16H10N4O4
2-(1,3-Benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enenitrile
—— (2S)-N-benzyl-2-cyano-3-(3-hydroxyphenyl)propanamide —— C17H16N2O2
(2S)-N-benzyl-2-cyano-3-(3-hydroxyphenyl)propanamide
—— (2R)-N-benzyl-2-cyano-3-(3-hydroxyphenyl)propanamide —— C17H16N2O2
(2R)-N-benzyl-2-cyano-3-(3-hydroxyphenyl)propanamide
—— (2S)-N-benzyl-2-cyano-3-(4-hydroxyphenyl)propanamide —— C17H16N2O2
(2S)-N-benzyl-2-cyano-3-(4-hydroxyphenyl)propanamide
—— diethyl 2-amino-4-(3-hydroxyphenyl)-6-methyl-4H-pyran-3,5-dicarboxylate —— C18H21NO6
diethyl 2-amino-4-(3-hydroxyphenyl)-6-methyl-4H-pyran-3,5-dicarboxylate
—— 4-[(2R,5R)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol —— C15H23NO4
4-[(2R,5R)-5-(hydroxymethyl)-3-(2-methylpropyl)-1,3-oxazolidin-2-yl]-2-methoxyphenol
—— Methyl 2-(3-hydroxy-4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate —— C13H13NO4S
Methyl 2-(3-hydroxy-4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
—— 3-[2-(3-Hydroxy-4-methoxyphenyl)-1,3-thiazol-4-yl]propanoic acid —— C13H13NO4S
3-[2-(3-Hydroxy-4-methoxyphenyl)-1,3-thiazol-4-yl]propanoic acid
—— 7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methylidene-6,7-dihydro-1H-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H21N5O4
7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methylidene-6,7-dihydro-1H-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— tert-butyl N-[(S)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]carbamate —— C14H18N2O4
tert-butyl N-[(S)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]carbamate
—— tert-butyl N-[(R)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]carbamate —— C14H18N2O4
tert-butyl N-[(R)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]carbamate
—— tert-butyl N-[(R)-cyano-(3-hydroxy-4-methoxyphenyl)methyl]carbamate —— C14H18N2O4
tert-butyl N-[(R)-cyano-(3-hydroxy-4-methoxyphenyl)methyl]carbamate
—— 5-[(4-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H13NO3S2
5-[(4-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2S)-N-tert-butyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C15H20N2O3
(2S)-N-tert-butyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— (2S)-N-tert-butyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C15H20N2O3
(2S)-N-tert-butyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— (2R)-N-tert-butyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C15H20N2O3
(2R)-N-tert-butyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— 2-hydroxy-5-nitro-N-[(5-nitrothiophen-2-yl)methylideneamino]benzamide —— C12H8N4O6S
2-hydroxy-5-nitro-N-[(5-nitrothiophen-2-yl)methylideneamino]benzamide
—— (2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(2-methylpropyl)propanamide —— C15H20N2O3
(2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(2-methylpropyl)propanamide
—— (2R)-N-tert-butyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C15H20N2O3
(2R)-N-tert-butyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— 4-[(4-Hydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one —— C11H9NO3
4-[(4-Hydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one
—— 7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H21F3O4
7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-[2-[6-(Aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]phenol —— C12H13N5OS
4-[2-[6-(Aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]phenol
—— 3-[2-[6-(Aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]phenol —— C12H13N5OS
3-[2-[6-(Aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]phenol
—— N-[1-(3-aminophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H15N3O4
N-[1-(3-aminophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— (2S)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-oxo-3-pyrrolidin-1-ylpropanenitrile —— C15H18N2O3
(2S)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-oxo-3-pyrrolidin-1-ylpropanenitrile
—— 1-(3,5-Dimethylpyrazol-1-yl)-3-(4-hydroxy-3-methoxyphenyl)propan-1-one —— C15H18N2O3
1-(3,5-Dimethylpyrazol-1-yl)-3-(4-hydroxy-3-methoxyphenyl)propan-1-one
—— (2S)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-oxo-3-pyrrolidin-1-ylpropanenitrile —— C15H18N2O3
(2S)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-oxo-3-pyrrolidin-1-ylpropanenitrile
—— (2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-oxo-3-pyrrolidin-1-ylpropanenitrile —— C15H18N2O3
(2R)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-oxo-3-pyrrolidin-1-ylpropanenitrile
—— 2-(5-Ethylidene-2-phenylpyrazolidin-3-yl)phenol —— C17H18N2O
2-(5-Ethylidene-2-phenylpyrazolidin-3-yl)phenol
—— 2-[6-(4-Bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-chlorophenol —— C22H18BrCl2N2O+
2-[6-(4-Bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-chlorophenol
—— 2-[6-(4-Bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-chlorophenol —— C22H17BrCl2N2O
2-[6-(4-Bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-chlorophenol
—— (2S)-2-[(3-hydroxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile —— C15H19N3O2
(2S)-2-[(3-hydroxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile
—— (2S)-2-[(4-hydroxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile —— C15H19N3O2
(2S)-2-[(4-hydroxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile
—— 4-Bromo-2-[[[2-[(4-chlorophenyl)methyl]-1,3-benzoxazol-5-yl]amino]methyl]-6-methoxyphenol —— C22H18BrClN2O3
4-Bromo-2-[[[2-[(4-chlorophenyl)methyl]-1,3-benzoxazol-5-yl]amino]methyl]-6-methoxyphenol
—— (2R)-2-[(3-hydroxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile —— C15H19N3O2
(2R)-2-[(3-hydroxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile
—— (2R)-2-cyano-N-cyclohexyl-3-(4-hydroxyphenyl)propanamide —— C16H20N2O2
(2R)-2-cyano-N-cyclohexyl-3-(4-hydroxyphenyl)propanamide
—— (2S)-2-cyano-N-cyclohexyl-3-(3-hydroxyphenyl)propanamide —— C16H20N2O2
(2S)-2-cyano-N-cyclohexyl-3-(3-hydroxyphenyl)propanamide
—— N-[1-(4-bromophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H13BrN2O4
N-[1-(4-bromophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H19N2O4S2+
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-(butylideneamino)-3,4,5-trihydroxybenzamide —— C11H14N2O4
N-(butylideneamino)-3,4,5-trihydroxybenzamide