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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-(4-chloro-2-methylphenoxy)-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C16H14ClN3O5
2-(4-chloro-2-methylphenoxy)-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylpropanamide —— C12H16N2O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylpropanamide
—— 4-[(4-Benzylsulfonylpiperazin-1-ium-1-yl)methyl]-2,6-dimethoxyphenol —— C20H27N2O5S+
4-[(4-Benzylsulfonylpiperazin-1-ium-1-yl)methyl]-2,6-dimethoxyphenol
—— (2-Hydroxy-3-methoxyphenyl)methyl-(2-methoxyethyl)azanium —— C11H18NO3+
(2-Hydroxy-3-methoxyphenyl)methyl-(2-methoxyethyl)azanium
—— 4-[(E)-3-(4-benzylpiperazine-1,4-diium-1-yl)prop-1-enyl]-2-bromo-6-methoxyphenol —— C21H27BrN2O2+2
4-[(E)-3-(4-benzylpiperazine-1,4-diium-1-yl)prop-1-enyl]-2-bromo-6-methoxyphenol
—— 2-[(3aS,7aS)-1,3,3a,4,5,6,7,7a-octahydro-2-benzothiophen-2-ium-2-yl]benzene-1,4-diol —— C14H19O2S+
2-[(3aS,7aS)-1,3,3a,4,5,6,7,7a-octahydro-2-benzothiophen-2-ium-2-yl]benzene-1,4-diol
—— 2-[(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydro-2-benzothiophen-2-ium-2-yl]benzene-1,4-diol —— C14H19O2S+
2-[(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydro-2-benzothiophen-2-ium-2-yl]benzene-1,4-diol
—— (5Z)-5-[(3-hydroxyphenyl)methylidene]-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5Z)-5-[(3-hydroxyphenyl)methylidene]-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-2-[4-(2-hydroxyethyl)piperazin-4-ium-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H20N3O3S+
(5Z)-2-[4-(2-hydroxyethyl)piperazin-4-ium-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (3,4-Dihydroxyphenyl)methyl-(pyridin-3-ylmethyl)azanium —— C13H15N2O2+
(3,4-Dihydroxyphenyl)methyl-(pyridin-3-ylmethyl)azanium
—— (2E,6R)-2-[(2-hydroxy-4-methylanilino)methylidene]-6-methylcyclohexan-1-one —— C15H19NO2
(2E,6R)-2-[(2-hydroxy-4-methylanilino)methylidene]-6-methylcyclohexan-1-one
—— (2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)propanamide —— C18H18N2O4
(2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)propanamide
—— diethyl (3S,4R)-4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate —— C20H25NO6
diethyl (3S,4R)-4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate
—— N-[(E)-1-(1-adamantyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C19H24N2O4
N-[(E)-1-(1-adamantyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— methyl (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate —— C14H13NO4
methyl (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate
—— (2R)-2-(4-hydroxy-3-methoxyphenyl)-2-[(3R)-5-(4-methoxyphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile —— C25H23N3O3
(2R)-2-(4-hydroxy-3-methoxyphenyl)-2-[(3R)-5-(4-methoxyphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]acetonitrile
—— 3-acetyl-2-[(2-hydroxy-5-methylphenyl)amino]-6-methyl-4H-pyran-4-one —— C15H15NO4
3-acetyl-2-[(2-hydroxy-5-methylphenyl)amino]-6-methyl-4H-pyran-4-one
—— (2R)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(2H-tetrazol-5-yl)propanamide —— C18H19N5O4
(2R)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)-2-(2H-tetrazol-5-yl)propanamide
—— (3E)-5-(2,4-dimethylphenyl)-3-(4-hydroxy-3-methoxybenzylidene)furan-2(3H)-one —— C20H18O4
(3E)-5-(2,4-dimethylphenyl)-3-(4-hydroxy-3-methoxybenzylidene)furan-2(3H)-one
—— (2E,5Z)-3-(2-ethoxyethyl)-5-(3-hydroxy-4-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C21H22N2O4S
(2E,5Z)-3-(2-ethoxyethyl)-5-(3-hydroxy-4-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (1S,4Z,8E,12R)-N-(2-hydroxy-4-nitrophenyl)bicyclo[10.1.0]trideca-4,8-diene-13-carboxamide —— C20H24N2O4
(1S,4Z,8E,12R)-N-(2-hydroxy-4-nitrophenyl)bicyclo[10.1.0]trideca-4,8-diene-13-carboxamide
—— 4-[(1S)-2-(tert-butylamino)-1-hydroxyethyl]-3-chloro-2-methoxyphenol —— C13H20ClNO3
4-[(1S)-2-(tert-butylamino)-1-hydroxyethyl]-3-chloro-2-methoxyphenol
—— 4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-3-chloro-2-methoxyphenol —— C13H20ClNO3
4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-3-chloro-2-methoxyphenol
—— [(2R)-1-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutan-2-yl] carbamate —— C14H21NO4
[(2R)-1-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutan-2-yl] carbamate
—— 5-(3-hydroxyphenyl)-4H-pyrazole-3-carboxylic acid —— C10H8N2O3
5-(3-hydroxyphenyl)-4H-pyrazole-3-carboxylic acid
—— [(2S)-1-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutan-2-yl] carbamate —— C14H21NO4
[(2S)-1-(4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutan-2-yl] carbamate
—— (2S,7R)-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H20N2O3S
(2S,7R)-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7S)-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H20N2O3S
(2R,7S)-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7R)-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H20N2O3S
(2R,7R)-2-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7S)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H19ClN2O3S
(2S,7S)-2-(5-chloro-2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C18H20N2O3S
(2R,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-methyl-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R)-2,3,3,3-tetrafluoro-N-(2-hydroxy-4-nitrophenyl)propanamide —— C9H6F4N2O4
(2R)-2,3,3,3-tetrafluoro-N-(2-hydroxy-4-nitrophenyl)propanamide
—— (5S)-11-ethyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C18H21N3O3S
(5S)-11-ethyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H24N3O3S+
(5S)-5-(3-hydroxy-4-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H23N3O3S
(5S)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H24N3O3S+
(5S)-11-benzyl-5-(3-hydroxy-4-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H24N3O3S+
(5R)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H23N3O3S
(5R)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— ethyl (5R)-5-(2-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate —— C19H21N3O5S
ethyl (5R)-5-(2-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate
—— (5S)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H24N3O3S+
(5S)-5-(2-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— ethyl (5S)-5-(3-hydroxy-4-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate —— C19H21N3O5S
ethyl (5S)-5-(3-hydroxy-4-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate
—— ethyl (5S)-5-(2-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate —— C19H21N3O5S
ethyl (5S)-5-(2-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate
—— (2S,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2S,7S)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7R)-2-(2-hydroxy-3-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2R,7R)-2-(2-hydroxy-3-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2R,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7S)-2-(2-hydroxy-3-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2R,7S)-2-(2-hydroxy-3-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O3S
(2S,7R)-2-(3-hydroxy-4-methoxyphenyl)-7-(2-methylbutan-2-yl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (5R)-5-(4-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C19H23N3O3S
(5R)-5-(4-hydroxy-3-methoxyphenyl)-11-propan-2-yl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— 4-O-ethyl 2-O-[2-(4-methoxyphenyl)ethyl] 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate —— C19H23NO5
4-O-ethyl 2-O-[2-(4-methoxyphenyl)ethyl] 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
—— (5Z)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5Z)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one