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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
—— (5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-2-(4-fluoroanilino)-1,3-thiazol-4-one —— C16H9BrClFN2O2S
(5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-2-(4-fluoroanilino)-1,3-thiazol-4-one
—— (1R,2S)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide —— C15H15NO4
(1R,2S)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-3-[(1R)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5E)-5-[(3-hydroxyphenyl)methylidene]-3-[(1R)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (1S,2S)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide —— C15H15NO4
(1S,2S)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide
—— (5Z)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione —— C14H14BrNO5S
(5Z)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5E)-5-[(3-hydroxyphenyl)methylidene]-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (1S,2R)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide —— C15H15NO4
(1S,2R)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide
—— (1R,2R)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide —— C15H15NO4
(1R,2R)-2-(furan-2-yl)-N-(2-hydroxy-5-methoxyphenyl)cyclopropane-1-carboxamide
—— (5R)-N-[(2-hydroxy-5-nitrophenyl)methyl]-5-methyl-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide —— C17H18N2O4S
(5R)-N-[(2-hydroxy-5-nitrophenyl)methyl]-5-methyl-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide
—— 1-benzyl-N-[(2-hydroxy-5-nitrophenyl)methyl]-3,5-dimethylpyrazole-4-carboxamide —— C20H20N4O4
1-benzyl-N-[(2-hydroxy-5-nitrophenyl)methyl]-3,5-dimethylpyrazole-4-carboxamide
—— (2R)-2-(4-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methylbutanamide —— C18H19ClN2O4
(2R)-2-(4-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methylbutanamide
—— 3-[3-(4-hydroxyphenyl)propyl]-1-methyl-1-[(1R,3R)-3-methylsulfanylcyclopentyl]urea —— C17H26N2O2S
3-[3-(4-hydroxyphenyl)propyl]-1-methyl-1-[(1R,3R)-3-methylsulfanylcyclopentyl]urea
—— 3-[3-(4-hydroxyphenyl)propyl]-1-methyl-1-[(1S,3S)-3-methylsulfanylcyclopentyl]urea —— C17H26N2O2S
3-[3-(4-hydroxyphenyl)propyl]-1-methyl-1-[(1S,3S)-3-methylsulfanylcyclopentyl]urea
—— 3-[3-(4-hydroxyphenyl)propyl]-1-methyl-1-[(1S,3R)-3-methylsulfanylcyclopentyl]urea —— C17H26N2O2S
3-[3-(4-hydroxyphenyl)propyl]-1-methyl-1-[(1S,3R)-3-methylsulfanylcyclopentyl]urea
—— 4-[2-(2,4-Dihydroxyphenyl)ethylamino]-4-oxobutanoate —— C12H14NO5-
4-[2-(2,4-Dihydroxyphenyl)ethylamino]-4-oxobutanoate
—— 4-[(4-Hydroxyphenyl)methylamino]-4-oxobutanoic acid —— C11H13NO4
4-[(4-Hydroxyphenyl)methylamino]-4-oxobutanoic acid
—— 4-[2-(3-Hydroxyphenyl)ethylamino]-4-oxobutanoate —— C12H14NO4-
4-[2-(3-Hydroxyphenyl)ethylamino]-4-oxobutanoate
—— 4-{[2-(3-Hydroxyphenyl)ethyl]amino}-4-oxobutanoic acid —— C12H15NO4
4-{[2-(3-Hydroxyphenyl)ethyl]amino}-4-oxobutanoic acid
—— 4-[(2,4-Dihydroxyphenyl)methylamino]-4-oxobutanoate —— C11H12NO5-
4-[(2,4-Dihydroxyphenyl)methylamino]-4-oxobutanoate
—— 4-[2-(4-Hydroxyphenyl)ethylamino]-4-oxobutanoate —— C12H14NO4-
4-[2-(4-Hydroxyphenyl)ethylamino]-4-oxobutanoate
—— 4-[(2,4-Dihydroxyphenyl)methylamino]-4-oxobutanoic acid —— C11H13NO5
4-[(2,4-Dihydroxyphenyl)methylamino]-4-oxobutanoic acid
—— 4-[(3-Hydroxyphenyl)methylamino]-4-oxobutanoic acid —— C11H13NO4
4-[(3-Hydroxyphenyl)methylamino]-4-oxobutanoic acid
—— 4-[(2-Hydroxy-3-methoxyphenyl)methylamino]-4-oxobutanoic acid —— C12H15NO5
4-[(2-Hydroxy-3-methoxyphenyl)methylamino]-4-oxobutanoic acid
—— 2-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylamino]-4-methyl-1,3-thiazole-5-carboxylate —— C13H12BrN2O4S-
2-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylamino]-4-methyl-1,3-thiazole-5-carboxylate
—— 2-[2-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylamino]-1,3-thiazol-4-yl]acetate —— C13H12BrN2O4S-
2-[2-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylamino]-1,3-thiazol-4-yl]acetate
—— 2-[2-[2-[(2,4-Dihydroxyphenyl)methylamino]-2-oxoethyl]-1,3-thiazol-4-yl]acetic acid —— C14H14N2O5S
2-[2-[2-[(2,4-Dihydroxyphenyl)methylamino]-2-oxoethyl]-1,3-thiazol-4-yl]acetic acid
—— 2-[2-[(2,4-Dihydroxyphenyl)methylamino]-1,3-thiazol-4-yl]acetate —— C12H11N2O4S-
2-[2-[(2,4-Dihydroxyphenyl)methylamino]-1,3-thiazol-4-yl]acetate
—— 2-[(2-Hydroxy-3-methoxyphenyl)methylamino]-4-methyl-1,3-thiazole-5-carboxylate —— C13H13N2O4S-
2-[(2-Hydroxy-3-methoxyphenyl)methylamino]-4-methyl-1,3-thiazole-5-carboxylate
—— 2-[2-[(2-Hydroxy-3-methoxyphenyl)methylamino]-2-oxoethyl]-4-methyl-1,3-thiazole-5-carboxylate —— C15H15N2O5S-
2-[2-[(2-Hydroxy-3-methoxyphenyl)methylamino]-2-oxoethyl]-4-methyl-1,3-thiazole-5-carboxylate
—— (3R)-1-[(2-hydroxy-3-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylate —— C13H14NO5-
(3R)-1-[(2-hydroxy-3-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylate
—— 3-[(1S)-1-[ethyl-[(2S)-2-hydroxybutyl]amino]ethyl]phenol —— C14H23NO2
3-[(1S)-1-[ethyl-[(2S)-2-hydroxybutyl]amino]ethyl]phenol
—— 3-[(1S)-1-[ethyl(prop-2-ynyl)amino]ethyl]phenol —— C13H17NO
3-[(1S)-1-[ethyl(prop-2-ynyl)amino]ethyl]phenol
—— 1-[2-[ethyl-[(1S)-1-(3-hydroxyphenyl)ethyl]amino]ethyl]pyrrolidine-2,5-dione —— C16H22N2O3
1-[2-[ethyl-[(1S)-1-(3-hydroxyphenyl)ethyl]amino]ethyl]pyrrolidine-2,5-dione
—— 3-[(1R)-1-[ethyl(prop-2-ynyl)amino]ethyl]phenol —— C13H17NO
3-[(1R)-1-[ethyl(prop-2-ynyl)amino]ethyl]phenol
—— 3-[(1S)-1-[ethyl-[(2R)-2-hydroxybutyl]amino]ethyl]phenol —— C14H23NO2
3-[(1S)-1-[ethyl-[(2R)-2-hydroxybutyl]amino]ethyl]phenol
—— 3-[(1R)-1-[ethyl(2-methylsulfonylethyl)amino]ethyl]phenol —— C13H21NO3S
3-[(1R)-1-[ethyl(2-methylsulfonylethyl)amino]ethyl]phenol
—— 1-[2-[ethyl-[(1R)-1-(3-hydroxyphenyl)ethyl]amino]ethyl]pyrrolidine-2,5-dione —— C16H22N2O3
1-[2-[ethyl-[(1R)-1-(3-hydroxyphenyl)ethyl]amino]ethyl]pyrrolidine-2,5-dione
—— 2-(4-Methoxyphenyl)ethyl 2-(4-methoxyphenyl)-1,3-thiazole-4-carboxylate —— C20H19NO4S
2-(4-Methoxyphenyl)ethyl 2-(4-methoxyphenyl)-1,3-thiazole-4-carboxylate
—— 2-methoxy-5-[[[(3R)-thian-3-yl]amino]methyl]phenol —— C13H19NO2S
2-methoxy-5-[[[(3R)-thian-3-yl]amino]methyl]phenol
—— (2S)-2-(1-benzofuran-2-yl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C19H19NO4
(2S)-2-(1-benzofuran-2-yl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (2R)-2-(1-benzofuran-2-yl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide —— C19H19NO4
(2R)-2-(1-benzofuran-2-yl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]propanamide
—— N-[(2R)-2-anilinopropyl]-3-hydroxy-4-nitrobenzamide —— C16H17N3O4
N-[(2R)-2-anilinopropyl]-3-hydroxy-4-nitrobenzamide
—— N-[(2S)-2-anilinopropyl]-3-hydroxy-4-nitrobenzamide —— C16H17N3O4
N-[(2S)-2-anilinopropyl]-3-hydroxy-4-nitrobenzamide
—— N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-pyridin-2-ylpropanamide —— C18H22N2O2
N-ethyl-N-[(1R)-1-(3-hydroxyphenyl)ethyl]-3-pyridin-2-ylpropanamide
—— N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-2-(6-methylpyridin-3-yl)acetamide —— C18H22N2O2
N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-2-(6-methylpyridin-3-yl)acetamide
—— N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-pyridin-2-ylpropanamide —— C18H22N2O2
N-ethyl-N-[(1S)-1-(3-hydroxyphenyl)ethyl]-3-pyridin-2-ylpropanamide
—— 1-[3-(4-hydroxyphenyl)propyl]-3-[(2S,3R)-2-phenyloxolan-3-yl]urea —— C20H24N2O3
1-[3-(4-hydroxyphenyl)propyl]-3-[(2S,3R)-2-phenyloxolan-3-yl]urea
—— 1-[3-(4-hydroxyphenyl)propyl]-3-[(2R,3R)-2-phenyloxolan-3-yl]urea —— C20H24N2O3
1-[3-(4-hydroxyphenyl)propyl]-3-[(2R,3R)-2-phenyloxolan-3-yl]urea
—— 1-[3-(4-hydroxyphenyl)propyl]-3-[(2R,3S)-2-phenyloxolan-3-yl]urea —— C20H24N2O3
1-[3-(4-hydroxyphenyl)propyl]-3-[(2R,3S)-2-phenyloxolan-3-yl]urea
—— 1-[3-(4-hydroxyphenyl)propyl]-3-[(2S,3S)-2-phenyloxolan-3-yl]urea —— C20H24N2O3
1-[3-(4-hydroxyphenyl)propyl]-3-[(2S,3S)-2-phenyloxolan-3-yl]urea