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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
—— (Z)-4-[(3S)-5-(1,3-benzodioxol-5-yl)-3-(2-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C21H18N2O7
(Z)-4-[(3S)-5-(1,3-benzodioxol-5-yl)-3-(2-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (E)-4-[(3R)-3-(2-hydroxyphenyl)-5-pyridin-3-yl-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C18H15N3O4
(E)-4-[(3R)-3-(2-hydroxyphenyl)-5-pyridin-3-yl-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (E)-4-[(3R)-5-(4-fluorophenyl)-3-(2-hydroxy-5-methylphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C20H17FN2O4
(E)-4-[(3R)-5-(4-fluorophenyl)-3-(2-hydroxy-5-methylphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (E)-4-[(3S)-3-(2-hydroxy-5-methylphenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C21H20N2O5
(E)-4-[(3S)-3-(2-hydroxy-5-methylphenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (E)-4-[(3S)-5-(4-fluorophenyl)-3-(2-hydroxy-5-methylphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C20H17FN2O4
(E)-4-[(3S)-5-(4-fluorophenyl)-3-(2-hydroxy-5-methylphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (4Z)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methyl-2-(2-methylphenyl)pyrazol-3-one —— C18H16N4O4
(4Z)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methyl-2-(2-methylphenyl)pyrazol-3-one
—— (E)-4-[(3R)-3-(2-hydroxy-5-methylphenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C21H20N2O5
(E)-4-[(3R)-3-(2-hydroxy-5-methylphenyl)-5-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylic acid —— C14H14N4O5
(7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-5-carboxylic acid
—— 2-(4-ethylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H20N2O4
2-(4-ethylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-hydroxy-5-nitro-3-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]benzenesulfonic acid —— C13H10N2O7S
2-hydroxy-5-nitro-3-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]benzenesulfonic acid
—— 3-hydroxy-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H14N2O4
3-hydroxy-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— methyl (2E)-2-(3-hydroxy-4-methoxybenzylidene)hydrazinecarboxylate —— C10H12N2O4
methyl (2E)-2-(3-hydroxy-4-methoxybenzylidene)hydrazinecarboxylate
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1,3-benzodioxole-5-carboxamide —— C16H14N2O5
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1,3-benzodioxole-5-carboxamide
—— 5-[(E)-[4-(4-bromophenyl)-2-(2-methoxyethylimino)-1,3-thiazol-3-yl]iminomethyl]-2-methoxyphenol —— C20H20BrN3O3S
5-[(E)-[4-(4-bromophenyl)-2-(2-methoxyethylimino)-1,3-thiazol-3-yl]iminomethyl]-2-methoxyphenol
—— benzyl (4R,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C23H24N2O6
benzyl (4R,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— prop-2-enyl (4S,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C19H22N2O6
prop-2-enyl (4S,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— prop-2-enyl (4R,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C19H22N2O6
prop-2-enyl (4R,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— benzyl (4S,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C23H24N2O6
benzyl (4S,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— 3-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methyl-5-phenylthieno[2,3-d]pyrimidin-4-one —— C21H17N3O3S
3-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methyl-5-phenylthieno[2,3-d]pyrimidin-4-one
—— N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]pyridine-3-carbohydrazide —— C14H13N3O3
N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]pyridine-3-carbohydrazide
—— ethyl (2Z,5R)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18ClN3O6S
ethyl (2Z,5R)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (7R)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C29H29N5O5S
(7R)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— N'-(3-hydroxy-4-methoxybenzylidene)-3-(1,1,2,2-tetrafluoroethoxy)benzohydrazide —— C17H14F4N2O4
N'-(3-hydroxy-4-methoxybenzylidene)-3-(1,1,2,2-tetrafluoroethoxy)benzohydrazide
—— 1-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile —— C16H15N3O3
1-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile
—— (7S)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C29H29N5O5S
(7S)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-2-[(3-methylphenyl)methylsulfanyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C29H29N5O4S
(7R)-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-2-[(3-methylphenyl)methylsulfanyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-benzylsulfanyl-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C28H27N5O4S
(7S)-2-benzylsulfanyl-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-[(2,4-dimethylphenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C30H31N5O4S
(7S)-2-[(2,4-dimethylphenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C29H29N5O5S
(7R)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-2-[(2,4-dimethylphenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C30H31N5O4S
(7R)-2-[(2,4-dimethylphenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-2-[(3-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C28H26ClN5O4S
(7R)-2-[(3-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-[(3-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C28H26ClN5O4S
(7S)-2-[(3-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C28H26FN5O4S
(7R)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-2-benzylsulfanyl-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C28H27N5O4S
(7R)-2-benzylsulfanyl-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C29H29N5O5S
(7S)-2-benzylsulfanyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C28H26FN5O4S
(7S)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-2-[(3-methylphenyl)methylsulfanyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C29H29N5O4S
(7S)-7-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-5-methyl-2-[(3-methylphenyl)methylsulfanyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (2E,5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-phenyl-2-(phenylhydrazinylidene)-1,3-thiazolidin-4-one —— C23H19N3O3S
(2E,5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-phenyl-2-(phenylhydrazinylidene)-1,3-thiazolidin-4-one
—— heptyl (7R)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C19H25N5O3
heptyl (7R)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— heptyl (7S)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C19H25N5O3
heptyl (7S)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— benzene-1,4-diol;iron;6-[[2-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]ethylamino]methylidene]cyclohexa-2,4-dien-1-one —— C38H38Fe2N4O6
benzene-1,4-diol;iron;6-[[2-[(6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]ethylamino]methylidene]cyclohexa-2,4-dien-1-one
—— methyl (4R)-6-[(5-bromothiophen-2-yl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H17BrN2O7S2
methyl (4R)-6-[(5-bromothiophen-2-yl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— prop-2-enyl (7R)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-[(2-chlorophenyl)methylsulfanyl]-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C24H22BrClN4O4S
prop-2-enyl (7R)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-[(2-chlorophenyl)methylsulfanyl]-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— methyl (4S)-6-[(5-bromothiophen-2-yl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H17BrN2O7S2
methyl (4S)-6-[(5-bromothiophen-2-yl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H13BrN2O4S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-1-phenyl-1,3-diazinane-2,4,6-trione —— C18H14N2O5
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-1-phenyl-1,3-diazinane-2,4,6-trione
—— 5-[(2-hydroxy-4-nitroanilino)methylidene]-1,4-dimethyl-2,6-dioxopyridine-3-carbonitrile —— C15H12N4O5
5-[(2-hydroxy-4-nitroanilino)methylidene]-1,4-dimethyl-2,6-dioxopyridine-3-carbonitrile
—— 2,4-dichloro-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C15H13Cl2NO2
2,4-dichloro-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-hydroxy-3,5-dinitro-N'-[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide —— C14H10N4O7
2-hydroxy-3,5-dinitro-N'-[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide
—— 3,4,5-trihydroxy-N'-[1-(6-methyl-2,4-dioxopyran-3-ylidene)ethyl]benzohydrazide —— C15H14N2O7
3,4,5-trihydroxy-N'-[1-(6-methyl-2,4-dioxopyran-3-ylidene)ethyl]benzohydrazide