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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
—— 1-[(2S)-2-(dimethylamino)-2-thiophen-2-ylethyl]-3-[2-(3-hydroxyphenyl)ethyl]urea —— C17H23N3O2S
1-[(2S)-2-(dimethylamino)-2-thiophen-2-ylethyl]-3-[2-(3-hydroxyphenyl)ethyl]urea
—— 2-[(Z)-1-nitro-2-(propan-2-ylamino)ethenyl]benzene-1,4-diol —— C11H14N2O4
2-[(Z)-1-nitro-2-(propan-2-ylamino)ethenyl]benzene-1,4-diol
—— (3E)-3-[[2-(3,4-dihydroxyphenyl)ethylamino]methylidene]-1-ethylindol-2-one —— C19H20N2O3
(3E)-3-[[2-(3,4-dihydroxyphenyl)ethylamino]methylidene]-1-ethylindol-2-one
—— N-[[(3S,8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-yl]methyl]-3-(2-hydroxyphenyl)propanamide —— C17H24N2O3
N-[[(3S,8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-yl]methyl]-3-(2-hydroxyphenyl)propanamide
—— N-[[(3R,8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-yl]methyl]-3-(2-hydroxyphenyl)propanamide —— C17H24N2O3
N-[[(3R,8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-yl]methyl]-3-(2-hydroxyphenyl)propanamide
—— ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-5-(3-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-5-(3-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (4Z)-1-(furan-2-ylmethyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate —— C20H19NO6
methyl (4Z)-1-(furan-2-ylmethyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methylphenyl)-1,3-diazinane-2,4,6-trione —— C19H16N2O5
(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methylphenyl)-1,3-diazinane-2,4,6-trione
—— Ethyl 2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-A]pyrimidine-6(3H)-carboxylate —— C24H21ClN2O5S
Ethyl 2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-A]pyrimidine-6(3H)-carboxylate
—— ethyl (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C18H18N2O4S
(5Z)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H13ClN2O4S
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C14H11N3O5S
(5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— Methyl (4Z)-1-ethyl-4-[(3-hydroxyphenyl)methylidene]-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C16H17NO4
Methyl (4Z)-1-ethyl-4-[(3-hydroxyphenyl)methylidene]-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 2-[(2E)-2-[(E)-(3-hydroxyphenyl)methylidenehydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl]acetic acid —— C12H11N3O4S
2-[(2E)-2-[(E)-(3-hydroxyphenyl)methylidenehydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl]acetic acid
—— (5Z)-5-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H7BrN2O4S2
(5Z)-5-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (E)-6-(3-bromo-4-hydroxy-5-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione —— C13H10BrN3O6
(E)-6-(3-bromo-4-hydroxy-5-methoxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
—— N-[(Z)-(4-fluorophenyl)methylideneamino]-2-(2-hydroxy-5-nitroanilino)-2-phenylacetamide —— C21H17FN4O4
N-[(Z)-(4-fluorophenyl)methylideneamino]-2-(2-hydroxy-5-nitroanilino)-2-phenylacetamide
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H15NO4S2
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C12H9BrN2O4S
5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— Ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-[4-(methylsulfanyl)phenyl]-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C25H23BrN2O5S2
Ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-[4-(methylsulfanyl)phenyl]-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN4O6S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-(5-chloro-2-hydroxybenzylidene)-5-(4-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Cl2N2O4S
ethyl 2-(5-chloro-2-hydroxybenzylidene)-5-(4-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O4S2
ethyl (2E)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-5-(2,5-dimethoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2Z)-5-(2,5-dimethoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C26H25BrN2O7S
Ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— ethyl 2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-5-(2-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O6S
ethyl 2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-5-(2-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-5-(3,4-dimethoxyphenyl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2Z)-5-(3,4-dimethoxyphenyl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17ClN2O4S2
ethyl (2E)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C25H23BrN2O6S
Ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— (Z)-ethyl 2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H19BrN2O5S2
(Z)-ethyl 2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26BrN3O5S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[2-[(2S)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,3-diol —— C13H15NO3S
4-[2-[(2S)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,3-diol
—— (5E)-1-ethyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H16N2O5S
(5E)-1-ethyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-[2-[(2R)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,3-diol —— C13H15NO3S
4-[2-[(2R)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,3-diol
—— 5-[[5-(2-Hydroxy-5-nitrophenyl)furan-2-yl]methylidene]-1,3-diazinane-2,4,6-trione —— C15H9N3O7
5-[[5-(2-Hydroxy-5-nitrophenyl)furan-2-yl]methylidene]-1,3-diazinane-2,4,6-trione
—— 4-[2-[(2R)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol —— C13H15NO3S
4-[2-[(2R)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol
—— 4-[2-[(2S)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol —— C13H15NO3S
4-[2-[(2S)-1-methoxypropan-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-4-methyl-5-oxo-1,4-dihydropyrazole-3-carboxamide —— C12H12N4O3
N-[(E)-(3-hydroxyphenyl)methylideneamino]-4-methyl-5-oxo-1,4-dihydropyrazole-3-carboxamide
—— 1H-Cyclopenta[c]pyrazole-3-carbohydrazide, 5,6(4H)-dihydro-N2-(3-hydroxy-4-methoxybenzylidene)- —— C15H16N4O3
1H-Cyclopenta[c]pyrazole-3-carbohydrazide, 5,6(4H)-dihydro-N2-(3-hydroxy-4-methoxybenzylidene)-
—— 3-(3,5-dimethyl-1H-pyrazol-4-yl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]propanehydrazide —— C16H20N4O3
3-(3,5-dimethyl-1H-pyrazol-4-yl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]propanehydrazide
—— (2E,5Z)-5-benzylidene-2-[(2E)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one —— C23H17N3O2S
(2E,5Z)-5-benzylidene-2-[(2E)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O5S
ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[(5Z)-5-benzylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C18H13N3O5S2
2-[(5Z)-5-benzylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide
—— ethyl (2Z)-5-[4-(dimethylamino)phenyl]-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H27N3O5S
ethyl (2Z)-5-[4-(dimethylamino)phenyl]-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O4S
ethyl (2Z)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Ethyl (2Z)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C24H21ClN2O5S
Ethyl (2Z)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O5S
ethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(4-methylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate