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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-[(R)-amino-[5-[(1S)-1-hydroxy-2-methylpropyl]-1,3,4-oxadiazol-2-yl]methyl]-4-methylphenol —— C14H19N3O3
2-[(R)-amino-[5-[(1S)-1-hydroxy-2-methylpropyl]-1,3,4-oxadiazol-2-yl]methyl]-4-methylphenol
—— (5E)-5-(4-hydroxy-3-nitrobenzylidene)-3-(4-nitrobenzyl)-1,3-thiazolidine-2,4-dione —— C17H11N3O7S
(5E)-5-(4-hydroxy-3-nitrobenzylidene)-3-(4-nitrobenzyl)-1,3-thiazolidine-2,4-dione
—— 2-[(5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C20H17BrN2O5S
2-[(5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— (2E,5E)-2,5-bis[(3,5-dibromo-2-hydroxyphenyl)methylidene]cyclopentan-1-one —— C19H12Br4O3
(2E,5E)-2,5-bis[(3,5-dibromo-2-hydroxyphenyl)methylidene]cyclopentan-1-one
—— N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]cyclohexanecarboxamide —— C15H20N2O2
N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]cyclohexanecarboxamide
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methylphenyl)-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C25H21BrN2O3S
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methylphenyl)-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (2E)-2-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C19H13FN2O2S
(2E)-2-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 6-amino-3-(3-hydroxyphenyl)-4-phenyl-2,4-dihydro-[1,2]oxazolo[5,4-b]pyridine-5-carbonitrile —— C19H14N4O2
6-amino-3-(3-hydroxyphenyl)-4-phenyl-2,4-dihydro-[1,2]oxazolo[5,4-b]pyridine-5-carbonitrile
—— ethyl (2Z)-2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z)-2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-(2-hydroxy-3-methoxybenzylidene)-3-(3-nitrobenzyl)-1,3-thiazolidine-2,4-dione —— C18H14N2O6S
(5Z)-5-(2-hydroxy-3-methoxybenzylidene)-3-(3-nitrobenzyl)-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C16H10BrN3O4S
(5E)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C19H18N2O2S
(5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— (E)-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylbutylamino)-2-oxoethyl]-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide —— C23H28N2O5S
(E)-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylbutylamino)-2-oxoethyl]-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide
—— (E)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide —— C24H28N2O5S
(E)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide
—— (6E)-6-[3-[(2-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C22H20N2O4
(6E)-6-[3-[(2-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— 3-{[(2E,5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoic acid —— C19H16N2O5S
3-{[(2E,5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoic acid
—— (Z)-2-(5-(2-hydroxy-5-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid —— C12H8N2O6S2
(Z)-2-(5-(2-hydroxy-5-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid
—— (5E)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C16H11N3O4S
(5E)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— 5-(4-Hydroxy-3,5-dimethoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C18H16N2O4S
5-(4-Hydroxy-3,5-dimethoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (5E)-5-[(2-hydroxy-4-methoxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H13NO3S2
(5E)-5-[(2-hydroxy-4-methoxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H9BrClNO2S2
(5E)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-(5-bromo-3-chloro-2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione —— C10H5BrClNO3S
(5E)-5-(5-bromo-3-chloro-2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione
—— 3-[2-(1,5-dioxonaphthalen-2-yl)hydrazinyl]-4-hydroxy-5-nitrobenzenesulfonic acid —— C16H11N3O8S
3-[2-(1,5-dioxonaphthalen-2-yl)hydrazinyl]-4-hydroxy-5-nitrobenzenesulfonic acid
—— 7-amino-8-(4-hydroxy-3-methoxybenzylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-8H-pyrrolo[2,1-c][1,4]thiazine-1,6-dicarbonitrile —— C24H18N4O5S
7-amino-8-(4-hydroxy-3-methoxybenzylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-8H-pyrrolo[2,1-c][1,4]thiazine-1,6-dicarbonitrile
—— (1R)-1-[5-[(S)-amino-(4-hydroxy-3-methylphenyl)methyl]-1,3,4-oxadiazol-2-yl]ethane-1,2-diol —— C12H15N3O4
(1R)-1-[5-[(S)-amino-(4-hydroxy-3-methylphenyl)methyl]-1,3,4-oxadiazol-2-yl]ethane-1,2-diol
—— (5Z)-3-(2-ethylhexyl)-5-(4-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C18H23NO2S2
(5Z)-3-(2-ethylhexyl)-5-(4-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— (Z)-3-(2-hydroxy-5-nitroanilino)-1-(4-methylphenyl)prop-2-en-1-one —— C16H14N2O4
(Z)-3-(2-hydroxy-5-nitroanilino)-1-(4-methylphenyl)prop-2-en-1-one
—— (5Z)-3-(2-ethylhexyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H23NO2S2
(5Z)-3-(2-ethylhexyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (2E)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2E)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(Z)-N-[(4,6-dimethylpyrimidin-2-yl)amino]-C-methylcarbonimidoyl]phenol —— C14H16N4O
3-[(Z)-N-[(4,6-dimethylpyrimidin-2-yl)amino]-C-methylcarbonimidoyl]phenol
—— (4Z)-4-[(5-chloro-2-hydroxyphenyl)methylidene]-1-(4-chlorophenyl)pyrazolidine-3,5-dione —— C16H10Cl2N2O3
(4Z)-4-[(5-chloro-2-hydroxyphenyl)methylidene]-1-(4-chlorophenyl)pyrazolidine-3,5-dione
—— 2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid [1-(3-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide —— C17H16N2O5
2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid [1-(3-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide
—— 4-[(5Z)-5-(4-ethylbenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)butanamide —— C22H21N3O5S2
4-[(5Z)-5-(4-ethylbenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)butanamide
—— 4-fluoro-N'-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide —— C15H13FN2O3
4-fluoro-N'-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide
—— 2-fluoro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H13FN2O3
2-fluoro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 5-methoxy-2-[1-[(2E)-2-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazinyl]ethenyl]phenol —— C17H17N3O2S
5-methoxy-2-[1-[(2E)-2-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazinyl]ethenyl]phenol
—— 4-(1,3-benzothiazol-2-ylsulfanylmethyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C23H19N3O3S2
4-(1,3-benzothiazol-2-ylsulfanylmethyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 1-(2,5-diethoxyphenyl)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione —— C22H21IN2O7
1-(2,5-diethoxyphenyl)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione
—— 5-[[(2S,5S)-2,5-dimethylpiperazin-1-yl]methyl]-2-methoxyphenol —— C14H22N2O2
5-[[(2S,5S)-2,5-dimethylpiperazin-1-yl]methyl]-2-methoxyphenol
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,5-dimethylfuran-3-carboxamide —— C15H16N2O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,5-dimethylfuran-3-carboxamide
—— 2-(2,4-dibromo-6-methoxyphenoxy)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C16H13Br2N3O6
2-(2,4-dibromo-6-methoxyphenoxy)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— 5-[2-(5-Chloro-2-hydroxyphenylamino)vinyl]-4-cyano-3-phenylisoxazole —— C18H12ClN3O2
5-[2-(5-Chloro-2-hydroxyphenylamino)vinyl]-4-cyano-3-phenylisoxazole
—— (3Z)-3-[(4-hydroxy-3-nitrophenyl)methylidene]-1H-indol-2-one —— C15H10N2O4
(3Z)-3-[(4-hydroxy-3-nitrophenyl)methylidene]-1H-indol-2-one
—— (5E)-3-(4-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H10ClNO3S2
(5E)-3-(4-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-ethyl-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C12H11N3O4S
(5Z)-3-ethyl-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— N-[(Z)-[3-bromo-4-[(2-chlorophenyl)methoxy]-5-methoxyphenyl]methylideneamino]-3,4,5-trihydroxybenzamide —— C22H18BrClN2O6
N-[(Z)-[3-bromo-4-[(2-chlorophenyl)methoxy]-5-methoxyphenyl]methylideneamino]-3,4,5-trihydroxybenzamide
—— 2,5-dichloro-3-[(E)-3-phenylmethoxyprop-1-enyl]benzene-1,4-diol —— C16H14Cl2O3
2,5-dichloro-3-[(E)-3-phenylmethoxyprop-1-enyl]benzene-1,4-diol
—— (3Z)-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-phenylthiophen-2-one —— C18H14O3S
(3Z)-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-phenylthiophen-2-one
—— (5Z)-3-(4,7-dimethoxy-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one —— C26H21N3O5S
(5Z)-3-(4,7-dimethoxy-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one