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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
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-5-thiophen-2-yltriazole-4-carboxamide —— C17H14N8O3S
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-5-thiophen-2-yltriazole-4-carboxamide
—— 3-[(Z)-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]hydrazinylidene]methyl]phenolate —— C15H16N8O3
3-[(Z)-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]hydrazinylidene]methyl]phenolate
—— (6E)-6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-2-phenyl-1H-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one —— C23H19N3O3
(6E)-6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-2-phenyl-1H-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one
—— (2E)-2-[4-(furan-2-yl)thiophen-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C18H13NO3S
(2E)-2-[4-(furan-2-yl)thiophen-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 2-[(5Z)-5-[(4-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O5S
2-[(5Z)-5-[(4-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 2-chloro-N-[(5E)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-4-methylbenzamide —— C19H15ClN2O4S2
2-chloro-N-[(5E)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-4-methylbenzamide
—— 4-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-[2-(4-hydroxyphenyl)ethyl]butanamide —— C20H20N2O4S2
4-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-[2-(4-hydroxyphenyl)ethyl]butanamide
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-(4-methylphenyl)-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C22H23N3O4S
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-(4-methylphenyl)-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-(4-methylphenyl)-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C22H23N3O4S
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-(4-methylphenyl)-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(2-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H20ClN3O4S
(4R)-1-(2-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C22H23N3O5S
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H20ClN3O4S
(4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H18N4O3S2
(4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H20ClN3O4S
(4S)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H23N5O4S
(4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-3-(furan-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one —— C16H13N3O4
(4S)-3-(furan-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one
—— methyl (4R)-6-[(2-chlorophenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H19ClN2O7S
methyl (4R)-6-[(2-chlorophenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— methyl (4R)-6-[(2,4-dimethylphenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C22H24N2O7S
methyl (4R)-6-[(2,4-dimethylphenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(4-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O5S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(4-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetamide
—— 2-[(5Z)-5-(2-chlorobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O4S2
2-[(5Z)-5-(2-chlorobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— methyl (4R)-6-[(4-tert-butylphenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C24H28N2O7S
methyl (4R)-6-[(4-tert-butylphenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-3-thiophen-2-yl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one —— C16H13N3O3S
(4R)-4-(4-hydroxy-3-methoxyphenyl)-3-thiophen-2-yl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-(furan-2-ylmethylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanamide —— C19H18N2O5S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-(furan-2-ylmethylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanamide
—— 2-[(5Z)-5-(3-chlorobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O4S2
2-[(5Z)-5-(3-chlorobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 4-[(5E)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide —— C21H22N2O5S2
4-[(5E)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide
—— 4-[(1R)-1-(4-tert-butylanilino)ethyl]-2-methoxyphenol —— C19H25NO2
4-[(1R)-1-(4-tert-butylanilino)ethyl]-2-methoxyphenol
—— 4-[(1S)-1-(4-tert-butylanilino)ethyl]-2-methoxyphenol —— C19H25NO2
4-[(1S)-1-(4-tert-butylanilino)ethyl]-2-methoxyphenol
—— N-[3-[[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]phenyl]acetamide —— C17H20N2O3
N-[3-[[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]phenyl]acetamide
—— N-[3-[[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]phenyl]acetamide —— C17H20N2O3
N-[3-[[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]phenyl]acetamide
—— 4-bromo-2-[(2R,6R)-2-(5-bromo-2-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H19Br2FN2O
4-bromo-2-[(2R,6R)-2-(5-bromo-2-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6S)-4-(4-ethylphenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrFN2O
4-bromo-2-[(2S,6S)-4-(4-ethylphenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrFN2O
4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-2-(4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H20BrFN2O
4-bromo-2-[(2S,6R)-2-(4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol —— C22H17BrCl2N2O
2-[(2R,6R)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol
—— 2-[(2R,6S)-2-(5-bromo-2-methoxyphenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H22BrClN2O3
2-[(2R,6S)-2-(5-bromo-2-methoxyphenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2R,6R)-2-(2-chlorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H20Cl2N2O2
2-[(2R,6R)-2-(2-chlorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2R,6S)-4-(4-chlorophenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H20ClFN2O2
2-[(2R,6S)-4-(4-chlorophenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2S,6R)-4-(4-ethylphenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrFN2O
4-bromo-2-[(2S,6R)-4-(4-ethylphenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6S)-2-(2-chlorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrClN2O
4-bromo-2-[(2R,6S)-2-(2-chlorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-4-(4-chlorophenyl)-2-[4-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H20ClF3N2O2
2-[(2R,6R)-4-(4-chlorophenyl)-2-[4-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2S,6R)-2-(2-chloro-6-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H16BrCl2FN2O
4-bromo-2-[(2S,6R)-2-(2-chloro-6-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-2-(5-bromo-2-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H19Br2FN2O
4-bromo-2-[(2S,6R)-2-(5-bromo-2-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6S)-2-(3-bromo-4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C23H19BrClFN2O
2-[(2S,6S)-2-(3-bromo-4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 2-[(2R,6R)-4-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H19Cl3N2O2
2-[(2R,6R)-4-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2R,6R)-2-(5-bromo-2-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C23H19BrClFN2O
2-[(2R,6R)-2-(5-bromo-2-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 2-[(2R,6R)-4-(4-chlorophenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H20ClFN2O2
2-[(2R,6R)-4-(4-chlorophenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2R,6S)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol —— C22H17BrCl2N2O
2-[(2R,6S)-2,4-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol
—— 4-bromo-2-[(2S,6S)-4-(4-ethylphenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrFN2O
4-bromo-2-[(2S,6S)-4-(4-ethylphenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6R)-2-(2-chloro-6-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H16BrCl2FN2O
4-bromo-2-[(2R,6R)-2-(2-chloro-6-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22BrFN2O
4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-(2-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol