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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
—— 2-(1-hydroxy-7a-methyl-4,5,6,7-tetrahydro-2H-benzimidazol-2-yl)phenol —— C14H18N2O2
2-(1-hydroxy-7a-methyl-4,5,6,7-tetrahydro-2H-benzimidazol-2-yl)phenol
—— 3-[1-[2-(2-Bromo-4-hydroxy-5-methoxyphenyl)acetyl]piperidin-4-yl]-5-(phenoxymethyl)-1,3-oxazolidin-2-one —— C24H27BrN2O6
3-[1-[2-(2-Bromo-4-hydroxy-5-methoxyphenyl)acetyl]piperidin-4-yl]-5-(phenoxymethyl)-1,3-oxazolidin-2-one
—— 8a-bromo-8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H16BrClO3
8a-bromo-8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 1-[(4R)-3,4-dihydro-2H-thiochromen-4-yl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea —— C18H20N2O3S
1-[(4R)-3,4-dihydro-2H-thiochromen-4-yl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea
—— 1-[(4S)-3,4-dihydro-2H-thiochromen-4-yl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea —— C18H20N2O3S
1-[(4S)-3,4-dihydro-2H-thiochromen-4-yl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea
—— Ethyl 4-(2-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C15H18N2O5
Ethyl 4-(2-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— N-[(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-2-methylbenzamide —— C19H16N2O4S2
N-[(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-2-methylbenzamide
—— ethyl (2Z,5S)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O4S2
ethyl (2Z,5S)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E)-2-[(5E)-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)acetonitrile —— C22H19Br2N5O2S
(2E)-2-[(5E)-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)acetonitrile
—— ethyl (2Z,5S)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O5S
ethyl (2Z,5S)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-[(2S)-3-(3,5-dimethylpyrazol-1-yl)-2-methylpropyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea —— C18H26N4O3
1-[(2S)-3-(3,5-dimethylpyrazol-1-yl)-2-methylpropyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea
—— 1-[[(3S)-3,4-dihydro-2H-chromen-3-yl]methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea —— C19H22N2O4
1-[[(3S)-3,4-dihydro-2H-chromen-3-yl]methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea
—— (4S)-4-(4-hydroxyphenyl)-2-oxo-6-propylsulfanyl-3,4-dihydro-1H-pyridine-5-carbonitrile —— C15H16N2O2S
(4S)-4-(4-hydroxyphenyl)-2-oxo-6-propylsulfanyl-3,4-dihydro-1H-pyridine-5-carbonitrile
—— (5E)-5-[(2-bromo-5-hydroxyphenyl)methylidene]-3-(4-methylphenyl)-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C24H19BrN2O2S
(5E)-5-[(2-bromo-5-hydroxyphenyl)methylidene]-3-(4-methylphenyl)-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— 5-(3,5-Dibromo-4-hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one —— C16H9Br2NO2S2
5-(3,5-Dibromo-4-hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one
—— 1-[[(3R)-3,4-dihydro-2H-chromen-3-yl]methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea —— C19H22N2O4
1-[[(3R)-3,4-dihydro-2H-chromen-3-yl]methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea
—— 5-[(2-Hydroxyphenyl)methylidene]-3-methyl-2-(nitromethylidene)-1,3-thiazolidin-4-one —— C12H10N2O4S
5-[(2-Hydroxyphenyl)methylidene]-3-methyl-2-(nitromethylidene)-1,3-thiazolidin-4-one
—— 1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]-3-(1H-pyrazol-5-ylmethyl)urea —— C17H22N4O3
1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]-3-(1H-pyrazol-5-ylmethyl)urea
—— 4-amino-5-N-benzyl-5-N-[1-(4-hydroxy-3-methoxyphenyl)-2-(3-methylbutylamino)-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide —— C26H31N5O5S
4-amino-5-N-benzyl-5-N-[1-(4-hydroxy-3-methoxyphenyl)-2-(3-methylbutylamino)-2-oxoethyl]-1,2-thiazole-3,5-dicarboxamide
—— 1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-(6-methylsulfonylpyridin-3-yl)urea —— C17H21N3O4S
1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-(6-methylsulfonylpyridin-3-yl)urea
—— 4-[(2-Propan-2-ylimino-4-thiophen-2-yl-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,3-triol —— C17H17N3O3S2
4-[(2-Propan-2-ylimino-4-thiophen-2-yl-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,3-triol
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-3-[(2S)-1-pyrazol-1-ylpropan-2-yl]urea —— C15H20N4O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-3-[(2S)-1-pyrazol-1-ylpropan-2-yl]urea
—— methyl (4S,5R)-4-(2-hydroxy-5-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C13H13N3O6
methyl (4S,5R)-4-(2-hydroxy-5-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione —— C14H13ClO6
5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 5-(3-Bromo-5-chloro-2-hydroxybenzylidene)-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one —— C22H14BrClN2O2S
5-(3-Bromo-5-chloro-2-hydroxybenzylidene)-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one
—— (4E)-1-(3,5-dichlorophenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C18H14Cl2N2O5
(4E)-1-(3,5-dichlorophenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— N-[(3R)-1,1-dioxothiolan-3-yl]-4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxamide —— C16H20N2O4S
N-[(3R)-1,1-dioxothiolan-3-yl]-4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxamide
—— 1-[(3S)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-1,3-dihydropyrazol-2-yl]ethanone —— C15H14N2O2S
1-[(3S)-3-(4-hydroxyphenyl)-5-thiophen-2-yl-1,3-dihydropyrazol-2-yl]ethanone
—— 1-cyclopropyl-1-[(4-hydroxyphenyl)methyl]-3-[(2S)-1-pyrazol-1-ylpropan-2-yl]urea —— C17H22N4O2
1-cyclopropyl-1-[(4-hydroxyphenyl)methyl]-3-[(2S)-1-pyrazol-1-ylpropan-2-yl]urea
—— (3E,5E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-1-propylpiperidin-1-ium-4-one —— C24H28NO5+
(3E,5E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-1-propylpiperidin-1-ium-4-one
—— 1-cyclopropyl-1-[(4-hydroxyphenyl)methyl]-3-[(2R)-1-pyrazol-1-ylpropan-2-yl]urea —— C17H22N4O2
1-cyclopropyl-1-[(4-hydroxyphenyl)methyl]-3-[(2R)-1-pyrazol-1-ylpropan-2-yl]urea
—— 4-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,3-diol —— C15H18N2O2
4-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,3-diol
—— 2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,4-diol —— C15H18N2O2
2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,4-diol
—— 3-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C15H18N2O
3-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 4-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,3-diol —— C15H18N2O2
4-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,3-diol
—— 4-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C15H18N2O
4-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 4-methyl-2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C16H20N2O
4-methyl-2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 2-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C15H18N2O
2-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 5-methyl-2-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C16H20N2O
5-methyl-2-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 5-methyl-2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C16H20N2O
5-methyl-2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 3-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C15H18N2O
3-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol —— C15H18N2O
2-[(1R)-1-(2-pyridin-4-ylethylamino)ethyl]phenol
—— 2-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,4-diol —— C15H18N2O2
2-[(1S)-1-(2-pyridin-4-ylethylamino)ethyl]benzene-1,4-diol
—— Methyl (4Z)-4-[(3-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(2-phenylethyl)-4,5-dihydro-1H-pyrrole-3-carboxylate —— C22H21NO4
Methyl (4Z)-4-[(3-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(2-phenylethyl)-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 5-(4-Hydroxy-3-methoxybenzylidene)-3-[2-(4-morpholinyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione —— C17H18N2O6S
5-(4-Hydroxy-3-methoxybenzylidene)-3-[2-(4-morpholinyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione
—— 5-(2,4-Dihydroxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one —— C12H11NO3S2
5-(2,4-Dihydroxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-5-(3,4-dihydroxybenzylidene)-2-[(2,3-dimethylphenyl)amino]-1,3-thiazol-4(5H)-one —— C18H16N2O3S
(5Z)-5-(3,4-dihydroxybenzylidene)-2-[(2,3-dimethylphenyl)amino]-1,3-thiazol-4(5H)-one
—— 8-O-ethyl 6-O-methyl (2Z,7S)-5-amino-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate —— C25H22N2O7S
8-O-ethyl 6-O-methyl (2Z,7S)-5-amino-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate
—— 6-benzyl-3-[2-[1-(2,4-dihydroxyphenyl)ethylidene]hydrazinyl]-4H-1,2,4-triazin-5-one —— C18H17N5O3
6-benzyl-3-[2-[1-(2,4-dihydroxyphenyl)ethylidene]hydrazinyl]-4H-1,2,4-triazin-5-one
—— 2-[(3-Iodosalicylidene)amino]-4-methylphenol —— C14H12INO2
2-[(3-Iodosalicylidene)amino]-4-methylphenol