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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
—— (5E)-3-(4-chlorophenyl)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12ClNO3S2
(5E)-3-(4-chlorophenyl)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2E,5Z)-5-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-methyl-2-(methylimino)-1,3-thiazolidin-4-one —— C12H10BrClN2O2S
(2E,5Z)-5-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-methyl-2-(methylimino)-1,3-thiazolidin-4-one
—— methyl (4E)-4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2R)-oxolan-2-yl]methyl]pyrrole-3-carboxylate —— C19H21NO5
methyl (4E)-4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2R)-oxolan-2-yl]methyl]pyrrole-3-carboxylate
—— (5Z)-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— methyl (4E)-4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2S)-oxolan-2-yl]methyl]pyrrole-3-carboxylate —— C19H21NO5
methyl (4E)-4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-[[(2S)-oxolan-2-yl]methyl]pyrrole-3-carboxylate
—— (5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-ethyl-1,3-thiazolidine-2,4-dione —— C12H9BrClNO3S
(5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-ethyl-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H18BrNO3S2
(5E)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO3S2
(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(4-Chlorophenyl)imino-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C16H10ClN3O4S
2-(4-Chlorophenyl)imino-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO3S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 6-[5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C17H19NO5S2
6-[5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-[(2E)-2-[(4-nitrophenyl)methylidene]hydrazinyl]-1,3-thiazol-4-one —— C17H11N5O6S
(5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-[(2E)-2-[(4-nitrophenyl)methylidene]hydrazinyl]-1,3-thiazol-4-one
—— 6-Amino-4-(3,4-dihydroxyphenyl)-3-(pyridin-4-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C18H13N5O3
6-Amino-4-(3,4-dihydroxyphenyl)-3-(pyridin-4-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]hexanamide —— C14H20N2O3
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]hexanamide
—— (5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-2-(2-chloroanilino)-1,3-thiazol-4-one —— C16H9BrClN3O4S
(5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-2-(2-chloroanilino)-1,3-thiazol-4-one
—— Cyclooctyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C21H27BrN2O5
Cyclooctyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— N-(cyclohexylideneamino)-3,4,5-trihydroxybenzamide —— C13H16N2O4
N-(cyclohexylideneamino)-3,4,5-trihydroxybenzamide
—— (Z)-1-(2-hydroxy-4-methylphenyl)-3-pyridin-3-ylprop-2-en-1-one —— C15H13NO2
(Z)-1-(2-hydroxy-4-methylphenyl)-3-pyridin-3-ylprop-2-en-1-one
—— 1-(2-Furoyl)-2-(3,4,5-trihydroxybenzoyl)hydrazine —— C12H10N2O6
1-(2-Furoyl)-2-(3,4,5-trihydroxybenzoyl)hydrazine
—— 2-[(4-Hydroxy-3-iodo-5-methoxyphenyl)methylidene]-1-benzothiophen-3-one —— C16H11IO3S
2-[(4-Hydroxy-3-iodo-5-methoxyphenyl)methylidene]-1-benzothiophen-3-one
—— (5Z)-5-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H11NO3S2
(5Z)-5-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-propan-2-yl-1,3-thiazolidine-2,4-dione —— C13H11BrClNO3S
(5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-propan-2-yl-1,3-thiazolidine-2,4-dione
—— methyl 2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19IN2O5S
methyl 2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— diethyl 2-[amino-[2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]methylidene]propanedioate —— C16H21N3O6
diethyl 2-[amino-[2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]methylidene]propanedioate
—— 5-[[(4,6-Dichloropyridin-2-yl)hydrazinylidene]methyl]-2-nitrophenol —— C12H8Cl2N4O3
5-[[(4,6-Dichloropyridin-2-yl)hydrazinylidene]methyl]-2-nitrophenol
—— 4-(1,3-Benzoxazol-2-ylsulfanyl)-2,6-dinitrophenol —— C13H7N3O6S
4-(1,3-Benzoxazol-2-ylsulfanyl)-2,6-dinitrophenol
—— N-[(3-hydroxyphenyl)methylideneamino]-2-(3-methylidene-5-oxopyrazolidin-4-yl)acetamide —— C13H14N4O3
N-[(3-hydroxyphenyl)methylideneamino]-2-(3-methylidene-5-oxopyrazolidin-4-yl)acetamide
—— methyl 6-acetyl-7-(4-hydroxy-3-methoxyphenyl)-1,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylate —— C15H15N5O5
methyl 6-acetyl-7-(4-hydroxy-3-methoxyphenyl)-1,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylate
—— 6-[(Z)-2-(2,3-dibromo-4-hydroxy-5-methoxyphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione —— C13H9Br2N3O6
6-[(Z)-2-(2,3-dibromo-4-hydroxy-5-methoxyphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione
—— alpha-(2-Chloro-5-(trifluoromethyl)phenylimino)-6-methoxy-O-cresol —— C15H11ClF3NO2
alpha-(2-Chloro-5-(trifluoromethyl)phenylimino)-6-methoxy-O-cresol
—— (2Z,5E)-2-[(E)-benzylidenehydrazinylidene]-3-[(1R)-cyclopent-2-en-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C22H19N3O2S
(2Z,5E)-2-[(E)-benzylidenehydrazinylidene]-3-[(1R)-cyclopent-2-en-1-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[[(5,6-Dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C16H16N4O2S
5-[[(5,6-Dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— N-[(2-hydroxy-5-nitrophenyl)methylideneamino]-2-oxopiperidine-3-carboxamide —— C13H14N4O5
N-[(2-hydroxy-5-nitrophenyl)methylideneamino]-2-oxopiperidine-3-carboxamide
—— 5-[(Z)-2-(1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C16H13NO2S
5-[(Z)-2-(1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— N-[(3-bromo-5-ethoxy-4-methoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C17H16BrN3O6
N-[(3-bromo-5-ethoxy-4-methoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— methyl (4E)-1-cyclohexyl-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate —— C21H25NO5
methyl (4E)-1-cyclohexyl-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— 4-[(1R)-1-hydroxy-2-(2-hydroxyethylamino)ethyl]benzene-1,2-diol —— C10H15NO4
4-[(1R)-1-hydroxy-2-(2-hydroxyethylamino)ethyl]benzene-1,2-diol
—— 4-[(1S)-1-hydroxy-2-(2-methylpropylamino)ethyl]phenol —— C12H19NO2
4-[(1S)-1-hydroxy-2-(2-methylpropylamino)ethyl]phenol
—— 4-[(1R)-1-hydroxy-2-(2-methylpropylamino)ethyl]phenol —— C12H19NO2
4-[(1R)-1-hydroxy-2-(2-methylpropylamino)ethyl]phenol
—— 4-hydroxy-3-methoxy-N-[5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide —— C19H16N2O5S2
4-hydroxy-3-methoxy-N-[5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide
—— dimethyl 4-[(Z)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate —— C21H25NO7
dimethyl 4-[(Z)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— 2-[(5Z)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C20H17BrN2O5S
2-[(5Z)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— 7-ethenyl-8-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C24H26O5
7-ethenyl-8-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(3-hydroxyphenyl)methylideneamino]-3H-1,3,4-thiadiazole-2-thione —— C9H7N3OS2
5-[(3-hydroxyphenyl)methylideneamino]-3H-1,3,4-thiadiazole-2-thione
—— 3-[bis[(2S)-2-hydroxypropyl]amino]-2-methylphenol —— C13H21NO3
3-[bis[(2S)-2-hydroxypropyl]amino]-2-methylphenol
—— 2,3,5,6-Tetrabromo-4-tert-butoxy-phenol —— C10H10Br4O2
2,3,5,6-Tetrabromo-4-tert-butoxy-phenol
—— Ditert-butyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate —— C25H35NO7
Ditert-butyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— 4-[(1R,3S)-1,3-dihydroxybutyl]-3-[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol —— C14H22O6
4-[(1R,3S)-1,3-dihydroxybutyl]-3-[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol
—— 4-[(1R,3R)-1,3-dihydroxybutyl]-3-[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol —— C14H22O6
4-[(1R,3R)-1,3-dihydroxybutyl]-3-[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol
—— (4S)-4-butyl-4-(hydroxymethyl)-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione —— C20H22N2O4
(4S)-4-butyl-4-(hydroxymethyl)-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione