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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
—— (3S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-1-(3-phenoxypropanoyl)piperidine-3-carboxamide —— C23H28N2O5
(3S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-1-(3-phenoxypropanoyl)piperidine-3-carboxamide
—— 4-(4-chloro-2-methylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanamide —— C19H21ClN2O4
4-(4-chloro-2-methylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanamide
—— 3-benzyl-1-ethyl-1-[(1R)-1-(3-hydroxyphenyl)ethyl]urea —— C18H22N2O2
3-benzyl-1-ethyl-1-[(1R)-1-(3-hydroxyphenyl)ethyl]urea
—— 3-benzyl-1-ethyl-1-[(1S)-1-(3-hydroxyphenyl)ethyl]urea —— C18H22N2O2
3-benzyl-1-ethyl-1-[(1S)-1-(3-hydroxyphenyl)ethyl]urea
—— 2-[5-(6-Methylpyridin-3-yl)-1,3-oxazolidin-2-yl]phenol —— C15H16N2O2
2-[5-(6-Methylpyridin-3-yl)-1,3-oxazolidin-2-yl]phenol
—— N-[1-(3-hydroxyphenyl)ethylideneamino]decanamide —— C18H28N2O2
N-[1-(3-hydroxyphenyl)ethylideneamino]decanamide
—— methyl 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O6S
methyl 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N,N'-bis[(3-hydroxyphenyl)methylideneamino]butanediamide —— C18H18N4O4
N,N'-bis[(3-hydroxyphenyl)methylideneamino]butanediamide
—— (2S)-2-cyano-N-(4-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C17H15FN2O3
(2S)-2-cyano-N-(4-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— (2R)-2-cyano-N-(2-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C17H15FN2O3
(2R)-2-cyano-N-(2-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— (2S)-2-cyano-N-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C17H15FN2O3
(2S)-2-cyano-N-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— (2S)-2-cyano-N-(2-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C17H15FN2O3
(2S)-2-cyano-N-(2-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— (2S)-2-cyano-N-(2-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C17H15FN2O3
(2S)-2-cyano-N-(2-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— (2R)-2-cyano-N-(2-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C17H15FN2O3
(2R)-2-cyano-N-(2-fluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— 4-[(E)-2-(1-ethylpyridin-1-ium-2-yl)ethenyl]-2-methoxyphenol —— C16H18NO2+
4-[(E)-2-(1-ethylpyridin-1-ium-2-yl)ethenyl]-2-methoxyphenol
—— 5-[1-(4-Hydroxy-3-methoxyphenyl)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H11NO3S2
5-[1-(4-Hydroxy-3-methoxyphenyl)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-{(E)-[(5-chloro-2-methylphenyl)imino]methyl}-6-methoxyphenol —— C15H14ClNO2
2-{(E)-[(5-chloro-2-methylphenyl)imino]methyl}-6-methoxyphenol
—— 2-Methoxy-4-({[2-(pyrrolidin-1-yl)ethyl]amino}methyl)phenol —— C14H22N2O2
2-Methoxy-4-({[2-(pyrrolidin-1-yl)ethyl]amino}methyl)phenol
—— 2-[(2-Hydroxy-3,5-dinitrophenyl)methylidene]-5,7-dimethyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one —— C18H12N4O6S
2-[(2-Hydroxy-3,5-dinitrophenyl)methylidene]-5,7-dimethyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]heptanamide —— C15H22N2O3
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]heptanamide
—— ethyl 5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl 5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C20H17BrN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— (2S)-N-benzyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C18H18N2O3
(2S)-N-benzyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— (2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(2-methylphenyl)propanamide —— C18H18N2O3
(2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(2-methylphenyl)propanamide
—— (2R)-N-benzyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide —— C18H18N2O3
(2R)-N-benzyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanamide
—— (2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(3-methylphenyl)propanamide —— C18H18N2O3
(2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(3-methylphenyl)propanamide
—— (2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(4-methylphenyl)propanamide —— C18H18N2O3
(2R)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(4-methylphenyl)propanamide
—— (2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(3-methylphenyl)propanamide —— C18H18N2O3
(2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(3-methylphenyl)propanamide
—— (2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(4-methylphenyl)propanamide —— C18H18N2O3
(2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-(4-methylphenyl)propanamide
—— (2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-methyl-N-phenylpropanamide —— C18H18N2O3
(2S)-2-cyano-3-(3-hydroxy-4-methoxyphenyl)-N-methyl-N-phenylpropanamide
—— (2S)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(2-methylphenyl)propanamide —— C18H18N2O3
(2S)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(2-methylphenyl)propanamide
—— (2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-methyl-N-phenylpropanamide —— C18H18N2O3
(2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-methyl-N-phenylpropanamide
—— (2R)-N-benzyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C18H18N2O3
(2R)-N-benzyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— (2S)-N-benzyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide —— C18H18N2O3
(2S)-N-benzyl-2-cyano-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— 4-[5-[(4-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)butanamide —— C20H16FN3O5S2
4-[5-[(4-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)butanamide
—— 2,6-Dimethoxy-4-[[4-(pyridin-1-ium-3-ylmethyl)piperazine-1,4-diium-1-yl]methyl]phenol —— C19H28N3O3+3
2,6-Dimethoxy-4-[[4-(pyridin-1-ium-3-ylmethyl)piperazine-1,4-diium-1-yl]methyl]phenol
—— 3-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2-pyridin-3-yl-1,3-thiazolidin-4-one —— C17H18N2O3S
3-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2-pyridin-3-yl-1,3-thiazolidin-4-one
—— 2,6-Dimethoxy-4-[[4-(pyridin-3-ylmethyl)piperazine-1,4-diium-1-yl]methyl]phenol —— C19H27N3O3+2
2,6-Dimethoxy-4-[[4-(pyridin-3-ylmethyl)piperazine-1,4-diium-1-yl]methyl]phenol
—— N-[(4-hydroxy-3-nitrophenyl)methylideneamino]-2-(6-methyl-4-oxo-5-phenylthieno[2,3-d]pyrimidin-3-yl)acetamide —— C22H17N5O5S
N-[(4-hydroxy-3-nitrophenyl)methylideneamino]-2-(6-methyl-4-oxo-5-phenylthieno[2,3-d]pyrimidin-3-yl)acetamide
—— 3,4,5-trihydroxy-N-(2-phenylethylideneamino)benzamide —— C15H14N2O4
3,4,5-trihydroxy-N-(2-phenylethylideneamino)benzamide
—— N-[(4-ethylphenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C16H16N2O4
N-[(4-ethylphenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— methyl 2-[(2-chloro-5-methoxy-4-propan-2-yloxyphenyl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27ClN2O7S
methyl 2-[(2-chloro-5-methoxy-4-propan-2-yloxyphenyl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(1,3-benzoxazol-2-ylsulfanyl)-N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H14BrN3O4S
2-(1,3-benzoxazol-2-ylsulfanyl)-N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]acetamide 851169-22-7 C12H9N3O3S
2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]acetamide
—— 2,2'-(Propane-2,2-diyldisulfanediyl)bis(4-methylphenol) —— C17H20O2S2
2,2'-(Propane-2,2-diyldisulfanediyl)bis(4-methylphenol)
—— 5-[2-[6-(aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]-2-methoxyphenol —— C13H15N5O2S
5-[2-[6-(aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]-2-methoxyphenol
—— 2-methoxy-5-[4-(piperazin-1-ylmethyl)-1,3-thiazol-2-yl]phenol —— C15H19N3O2S
2-methoxy-5-[4-(piperazin-1-ylmethyl)-1,3-thiazol-2-yl]phenol
—— 4-[2-[6-(aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]-2-methoxyphenol —— C13H15N5O2S
4-[2-[6-(aminomethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]ethyl]-2-methoxyphenol
—— N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]furan-2-carbohydrazide —— C14H14N2O4
N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]furan-2-carbohydrazide
—— (2S)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile —— C16H21N3O3
(2S)-2-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(4-methylpiperazin-1-yl)-3-oxopropanenitrile