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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
—— 3-[(1S,2S)-2-amino-1-hydroxybutyl]phenol —— C10H15NO2
3-[(1S,2S)-2-amino-1-hydroxybutyl]phenol
—— 2-[(1S)-1-hydroxybutyl]phenol —— C10H14O2
2-[(1S)-1-hydroxybutyl]phenol
—— 2-[(1R)-1-hydroxybutyl]phenol —— C10H14O2
2-[(1R)-1-hydroxybutyl]phenol
—— 2-[2-[(2S)-1,3-thiazolidin-2-yl]ethyl]phenol —— C11H15NOS
2-[2-[(2S)-1,3-thiazolidin-2-yl]ethyl]phenol
—— 2-(3,5-Dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H20N2O2S
2-(3,5-Dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 1-(Furan-2-ylmethyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione —— C17H14N2O6
1-(Furan-2-ylmethyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
—— 4-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-chlorophenyl)pyrazolidine-3,5-dione —— C17H12Cl2N2O4
4-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-chlorophenyl)pyrazolidine-3,5-dione
—— 5-[(4-Hydroxy-3-iodophenyl)methylidene]-3-(oxolan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H14INO3S2
5-[(4-Hydroxy-3-iodophenyl)methylidene]-3-(oxolan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (Z)-N-(1,3-benzodioxol-5-ylmethyl)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide —— C27H30N2O7
(Z)-N-(1,3-benzodioxol-5-ylmethyl)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide
—— (Z)-N-benzyl-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide —— C26H30N2O5
(Z)-N-benzyl-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide
—— (Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylphenyl)ethyl]-4-oxobut-2-enamide —— C28H34N2O5
(Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylphenyl)ethyl]-4-oxobut-2-enamide
—— (Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-N-(furan-2-ylmethyl)-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide —— C24H28N2O6
(Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-N-(furan-2-ylmethyl)-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide
—— (Z)-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylbutylamino)-2-oxoethyl]-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide —— C23H28N2O5S
(Z)-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylbutylamino)-2-oxoethyl]-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide
—— (Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-N-[(4-fluorophenyl)methyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide —— C26H29FN2O5
(Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-N-[(4-fluorophenyl)methyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide
—— (Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-N-[(2-methoxyphenyl)methyl]-4-oxobut-2-enamide —— C27H32N2O6
(Z)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-N-[(2-methoxyphenyl)methyl]-4-oxobut-2-enamide
—— methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2S)-oxolan-2-yl]methyl]pyrrole-3-carboxylate —— C20H23NO6
methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2S)-oxolan-2-yl]methyl]pyrrole-3-carboxylate
—— methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2R)-oxolan-2-yl]methyl]pyrrole-3-carboxylate —— C20H23NO6
methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2R)-oxolan-2-yl]methyl]pyrrole-3-carboxylate
—— methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methoxypropyl)-2-methyl-5-oxopyrrole-3-carboxylate —— C19H23NO6
methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methoxypropyl)-2-methyl-5-oxopyrrole-3-carboxylate
—— 2-(3-Hydroxy-4-methoxyphenylmethylene)hydrazine —— C8H10N2O2
2-(3-Hydroxy-4-methoxyphenylmethylene)hydrazine
—— 2-bromo-4-(di-1H-indol-3-ylmethyl)-6-methoxyphenol —— C24H19BrN2O2
2-bromo-4-(di-1H-indol-3-ylmethyl)-6-methoxyphenol
—— dioxidanium;manganese(2+);2-(pyridin-2-yliminomethyl)phenolate —— C24H24MnN4O4+2
dioxidanium;manganese(2+);2-(pyridin-2-yliminomethyl)phenolate
—— 6-[(Z)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione —— C13H10ClN3O6
6-[(Z)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione
—— methyl N-[[3-[[(E)-[amino(methylsulfanyl)methylidene]hydrazinylidene]methyl]-2-hydroxy-5-methylphenyl]methylideneamino]ethanimidothioate —— C14H19N5OS2
methyl N-[[3-[[(E)-[amino(methylsulfanyl)methylidene]hydrazinylidene]methyl]-2-hydroxy-5-methylphenyl]methylideneamino]ethanimidothioate
—— 3-[(5S)-3-ethyl-2-imino-1,3-thiazolidin-5-yl]phenol —— C11H14N2OS
3-[(5S)-3-ethyl-2-imino-1,3-thiazolidin-5-yl]phenol
—— 4-[(2S)-1-amino-2-hydroxypropan-2-yl]phenol —— C9H13NO2
4-[(2S)-1-amino-2-hydroxypropan-2-yl]phenol
—— (5Z,8Z,11E,14E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide —— C28H41NO3
(5Z,8Z,11E,14E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide
—— (5Z,8Z,11Z,14E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide —— C28H41NO3
(5Z,8Z,11Z,14E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide
—— 4-[(2R)-1-amino-2-hydroxypropan-2-yl]phenol —— C9H13NO2
4-[(2R)-1-amino-2-hydroxypropan-2-yl]phenol
—— (Z)-3-(3-chloro-1-benzofuran-2-yl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one —— C18H13ClO4
(Z)-3-(3-chloro-1-benzofuran-2-yl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one
—— 5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C21H22N2O3S
5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— 5-[(5-Bromo-2-hydroxy-3-iodophenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C19H16BrIN2O3S
5-[(5-Bromo-2-hydroxy-3-iodophenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— 2-(2-Chlorophenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13ClN2O3S
2-(2-Chlorophenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[(2,4-Dihydroxyphenyl)methylidene]-4-(5-ethyl-1,3,4-thiadiazol-2-yl)-5-iminothiolan-3-one —— C15H13N3O3S2
2-[(2,4-Dihydroxyphenyl)methylidene]-4-(5-ethyl-1,3,4-thiadiazol-2-yl)-5-iminothiolan-3-one
—— (3R)-3-[(dimethylamino)methyl]-6-hydroxy-3H-2-benzothiophen-1-one —— C11H13NO2S
(3R)-3-[(dimethylamino)methyl]-6-hydroxy-3H-2-benzothiophen-1-one
—— Methyl 3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methyl-5-nitrophenyl)propanoate —— C11H10F3NO6
Methyl 3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methyl-5-nitrophenyl)propanoate
—— N-[(8R,8aR)-5,7,7-tricyano-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinolin-6-yl]-2-chloroacetamide —— C21H18ClN5O2
N-[(8R,8aR)-5,7,7-tricyano-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinolin-6-yl]-2-chloroacetamide
—— N-[(8R,8aS)-5,7,7-tricyano-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinolin-6-yl]-2-chloroacetamide —— C21H18ClN5O2
N-[(8R,8aS)-5,7,7-tricyano-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinolin-6-yl]-2-chloroacetamide
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(4-nitroanilino)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H13N3O5S2
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(4-nitroanilino)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-({[5-(1-Adamantyl)-2-methylphenyl]imino}methyl)-2-methoxyphenol —— C25H29NO2
4-({[5-(1-Adamantyl)-2-methylphenyl]imino}methyl)-2-methoxyphenol
—— (5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-(2,3-dichlorophenyl)imino-1,3-thiazolidin-4-one —— C16H8BrCl2N3O4S
(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-(2,3-dichlorophenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-3-ethyl-2-(2-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H20N2O2S
(5Z)-3-ethyl-2-(2-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— ethyl (2E,5S)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Cl2N2O4S
ethyl (2E,5S)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Cl2N2O4S
ethyl (2E,5R)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(5R)-2,2-dimethyl-1,3-oxazolidin-5-yl]phenol —— C11H15NO2
3-[(5R)-2,2-dimethyl-1,3-oxazolidin-5-yl]phenol
—— (2S,5E)-2-(4-ethylanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H20N2O3S
(2S,5E)-2-(4-ethylanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 3-(3-Hydroxyphenyl)-5-[(1-methylpyrrol-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H12N2O2S2
3-(3-Hydroxyphenyl)-5-[(1-methylpyrrol-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (Z)-1-(2-hydroxy-5-nitrophenyl)-3-pyridin-2-ylprop-2-en-1-one —— C14H10N2O4
(Z)-1-(2-hydroxy-5-nitrophenyl)-3-pyridin-2-ylprop-2-en-1-one
—— Methyl 1-butyl-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate —— C18H21NO4
Methyl 1-butyl-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— 3-Benzyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C25H22N2O2S
3-Benzyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— 2-[[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile —— C18H12N2O4S
2-[[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile