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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
—— (2R)-2-(4-hydroxyphenyl)-2-(prop-2-enylamino)acetonitrile —— C11H12N2O
(2R)-2-(4-hydroxyphenyl)-2-(prop-2-enylamino)acetonitrile
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-phenylimidazol-4-one —— C25H21N3O5
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-phenylimidazol-4-one
—— 5-[(2-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H14Cl2N2O5S2
5-[(2-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(4-fluorophenyl)-5-methylpyrazol-3-one —— C17H13ClFN3O2
4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(4-fluorophenyl)-5-methylpyrazol-3-one
—— 4-benzyl-6-[(2-hydroxy-5-methylanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one —— C21H18N2O4
4-benzyl-6-[(2-hydroxy-5-methylanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one
—— 4-hydroxy-N-[(2S)-2-hydroxypropyl]-N-methyl-3-nitrobenzenesulfonamide —— C10H14N2O6S
4-hydroxy-N-[(2S)-2-hydroxypropyl]-N-methyl-3-nitrobenzenesulfonamide
—— 3-[(7R)-7-(2-hydroxy-5-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
3-[(7R)-7-(2-hydroxy-5-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 6-[3-[(2-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C22H20N2O4
6-[3-[(2-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— 2-(4-bromophenyl)-4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methylpyrazol-3-one —— C17H13BrClN3O2
2-(4-bromophenyl)-4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methylpyrazol-3-one
—— 4-[3-[(4-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C22H20N2O4
4-[3-[(4-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— 4-hydroxy-3-methoxy-N'-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide —— C16H16N2O5
4-hydroxy-3-methoxy-N'-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide
—— 6-[(3-chloro-2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H9ClN2O4
6-[(3-chloro-2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— N'-[(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-4-hydroxy-3-methoxybenzohydrazide —— C15H13ClN2O4
N'-[(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-4-hydroxy-3-methoxybenzohydrazide
—— 6-[(2-hydroxy-5-methylanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one —— C14H12N2O4
6-[(2-hydroxy-5-methylanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one
—— 6-[(2-hydroxy-5-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one —— C15H15NO2
6-[(2-hydroxy-5-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one
—— 3,4,5-trihydroxy-N'-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide —— C15H14N2O6
3,4,5-trihydroxy-N'-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide
—— 4-[(2-hydroxy-5-nitroanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one —— C17H14N4O4
4-[(2-hydroxy-5-nitroanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one
—— 4-benzyl-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C21H19NO2
4-benzyl-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 3-(diethylamino)-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C18H22N2O2
3-(diethylamino)-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 3-[[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino]-3-oxopropanoic acid —— C13H17NO4
3-[[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino]-3-oxopropanoic acid
—— 2-[(1R)-1-[[(2S)-hexan-2-yl]amino]ethyl]-4-methoxyphenol —— C15H25NO2
2-[(1R)-1-[[(2S)-hexan-2-yl]amino]ethyl]-4-methoxyphenol
—— 4-[(1S)-1-[[(2R)-hexan-2-yl]amino]ethyl]benzene-1,3-diol —— C14H23NO2
4-[(1S)-1-[[(2R)-hexan-2-yl]amino]ethyl]benzene-1,3-diol
—— 5-methyl-2-(pyrrol-2-ylidenemethylamino)phenol —— C12H12N2O
5-methyl-2-(pyrrol-2-ylidenemethylamino)phenol
—— 2-hydroxy-N'-[(3-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide —— C14H11N3O6
2-hydroxy-N'-[(3-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide
—— 4-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]-3,5-dimethylcyclohexa-2,4-dien-1-one —— C16H16ClNO2
4-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]-3,5-dimethylcyclohexa-2,4-dien-1-one
—— 3-[5-[(1R)-1-(methylamino)ethyl]-1,3,4-oxadiazol-2-yl]phenol —— C11H13N3O2
3-[5-[(1R)-1-(methylamino)ethyl]-1,3,4-oxadiazol-2-yl]phenol
—— 4-bromo-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H9BrN2O4
4-bromo-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— 3-[(2S)-1,3-thiazolidin-2-yl]phenol —— C9H11NOS
3-[(2S)-1,3-thiazolidin-2-yl]phenol
—— 2-{[3-Cyano-4-(4-hydroxy-3-methoxyphenyl)-6-oxo-1,4,5,6-tetrahydropyridin-2-YL]sulfanyl}-N-(2,5-dimethylphenyl)acetamide —— C23H23N3O4S
2-{[3-Cyano-4-(4-hydroxy-3-methoxyphenyl)-6-oxo-1,4,5,6-tetrahydropyridin-2-YL]sulfanyl}-N-(2,5-dimethylphenyl)acetamide
—— 2-[(2-hydroxy-5-nitroanilino)methylidene]-1-benzothiophen-3-one —— C15H10N2O4S
2-[(2-hydroxy-5-nitroanilino)methylidene]-1-benzothiophen-3-one
—— N-[(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2-phenyl-1,3-thiazol-4-yl)acetamide —— C18H14N4O4S
N-[(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2-phenyl-1,3-thiazol-4-yl)acetamide
—— N'-(5-bromopyridin-2-yl)-N-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl]butanediamide —— C19H22BrN3O5
N'-(5-bromopyridin-2-yl)-N-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl]butanediamide
—— 2-(furan-2-ylmethylsulfonylmethyl)-N-[(3-hydroxy-4,5-dimethoxyphenyl)methylideneamino]-1,3-thiazole-4-carboxamide —— C19H19N3O7S2
2-(furan-2-ylmethylsulfonylmethyl)-N-[(3-hydroxy-4,5-dimethoxyphenyl)methylideneamino]-1,3-thiazole-4-carboxamide
—— 2-[(1S)-1-[[(3S)-hexan-3-yl]amino]ethyl]benzene-1,4-diol —— C14H23NO2
2-[(1S)-1-[[(3S)-hexan-3-yl]amino]ethyl]benzene-1,4-diol
—— 2-methoxy-4-[(1S)-1-[[(1S,2S)-2-methoxycyclopentyl]amino]ethyl]phenol —— C15H23NO3
2-methoxy-4-[(1S)-1-[[(1S,2S)-2-methoxycyclopentyl]amino]ethyl]phenol
—— 3-[(1R)-1-[[(1R,2S)-2-methoxycyclopentyl]amino]ethyl]phenol —— C14H21NO2
3-[(1R)-1-[[(1R,2S)-2-methoxycyclopentyl]amino]ethyl]phenol
—— 3-[(1S)-1-[[(1S,2S)-2-methoxycyclopentyl]amino]ethyl]phenol —— C14H21NO2
3-[(1S)-1-[[(1S,2S)-2-methoxycyclopentyl]amino]ethyl]phenol
—— 4-methoxy-2-[(1S)-1-[[(1S,2S)-2-methoxycyclopentyl]amino]ethyl]phenol —— C15H23NO3
4-methoxy-2-[(1S)-1-[[(1S,2S)-2-methoxycyclopentyl]amino]ethyl]phenol
—— 4-[[[(1S,2R)-2-methoxycyclopentyl]amino]methyl]benzene-1,2-diol —— C13H19NO3
4-[[[(1S,2R)-2-methoxycyclopentyl]amino]methyl]benzene-1,2-diol
—— 4-[[[(1R,2R)-2-methoxycyclopentyl]amino]methyl]benzene-1,2-diol —— C13H19NO3
4-[[[(1R,2R)-2-methoxycyclopentyl]amino]methyl]benzene-1,2-diol
—— 3-[(1S)-1-[[(1R)-1-thiophen-3-ylethyl]amino]ethyl]phenol —— C14H17NOS
3-[(1S)-1-[[(1R)-1-thiophen-3-ylethyl]amino]ethyl]phenol
—— (2-chloro-4-fluorophenyl)methyl N-[(4-hydroxy-3-methoxybenzoyl)amino]carbamate —— C16H14ClFN2O5
(2-chloro-4-fluorophenyl)methyl N-[(4-hydroxy-3-methoxybenzoyl)amino]carbamate
—— 3-[(1R)-1-[[(1S)-1-thiophen-3-ylethyl]amino]ethyl]phenol —— C14H17NOS
3-[(1R)-1-[[(1S)-1-thiophen-3-ylethyl]amino]ethyl]phenol
—— [1-(4-chlorophenyl)cyclopropyl]methyl N-[(4-hydroxy-3-methoxybenzoyl)amino]carbamate —— C19H19ClN2O5
[1-(4-chlorophenyl)cyclopropyl]methyl N-[(4-hydroxy-3-methoxybenzoyl)amino]carbamate
—— 4-chloro-2-[(1S)-1-(methylamino)ethyl]phenol —— C9H12ClNO
4-chloro-2-[(1S)-1-(methylamino)ethyl]phenol
—— 4-[[(3R)-3-(aminomethyl)pyrrolidin-1-yl]methyl]benzene-1,3-diol —— C12H18N2O2
4-[[(3R)-3-(aminomethyl)pyrrolidin-1-yl]methyl]benzene-1,3-diol
—— 5-[[(3R)-3-(aminomethyl)pyrrolidin-1-yl]methyl]-2-methoxyphenol —— C13H20N2O2
5-[[(3R)-3-(aminomethyl)pyrrolidin-1-yl]methyl]-2-methoxyphenol
—— 4-[[(3S)-3-(aminomethyl)pyrrolidin-1-yl]methyl]benzene-1,3-diol —— C12H18N2O2
4-[[(3S)-3-(aminomethyl)pyrrolidin-1-yl]methyl]benzene-1,3-diol
—— 4-[[(3S)-3-aminopyrrolidin-1-yl]methyl]benzene-1,3-diol —— C11H16N2O2
4-[[(3S)-3-aminopyrrolidin-1-yl]methyl]benzene-1,3-diol