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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
—— (6S)-4-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-10-prop-2-enyl-1,4,10-triazaspiro[5.6]dodecan-9-one —— C21H31N3O3
(6S)-4-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-10-prop-2-enyl-1,4,10-triazaspiro[5.6]dodecan-9-one
—— (3S)-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide —— C16H13N3O6
(3S)-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
—— N-[(1R)-1-(4-hydroxyphenyl)ethyl]-4-piperidin-1-ylbutanamide —— C17H26N2O2
N-[(1R)-1-(4-hydroxyphenyl)ethyl]-4-piperidin-1-ylbutanamide
—— N-[(1S)-1-(4-hydroxyphenyl)ethyl]-4-piperidin-1-ylbutanamide —— C17H26N2O2
N-[(1S)-1-(4-hydroxyphenyl)ethyl]-4-piperidin-1-ylbutanamide
—— 1-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]propan-1-one —— C16H16N2O2S
1-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]propan-1-one
—— 1-[(3R)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]propan-1-one —— C16H16N2O2S
1-[(3R)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]propan-1-one
—— 4-[(R)-[1-(2-methoxyethyl)tetrazol-5-yl]-(4-methylpiperazin-1-yl)methyl]phenol —— C16H24N6O2
4-[(R)-[1-(2-methoxyethyl)tetrazol-5-yl]-(4-methylpiperazin-1-yl)methyl]phenol
—— phenyl (4S)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H15N3O5S
phenyl (4S)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— phenyl (4R)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H15N3O5S
phenyl (4R)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H20N2O6
ethyl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (4R)-N-(4-ethylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C21H23N3O4
(4R)-N-(4-ethylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— (4S)-N-(4-ethylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C21H23N3O4
(4S)-N-(4-ethylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— ethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-propyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19N3O5S
ethyl (4S)-4-(4-hydroxy-3-nitrophenyl)-6-propyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-propyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19N3O5S
ethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-propyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-bromo-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]benzamide —— C14H10BrN3O4
2-bromo-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]benzamide
—— 1-[(4-hydroxyphenyl)methyl]-1-methyl-3-[(1R)-1-thiophen-2-ylethyl]urea —— C15H18N2O2S
1-[(4-hydroxyphenyl)methyl]-1-methyl-3-[(1R)-1-thiophen-2-ylethyl]urea
—— 2-[[[(S)-furan-2-yl(phenyl)methyl]amino]methyl]-6-methoxyphenol —— C19H19NO3
2-[[[(S)-furan-2-yl(phenyl)methyl]amino]methyl]-6-methoxyphenol
—— 1-[(4-hydroxyphenyl)methyl]-1-methyl-3-[(1S)-1-thiophen-2-ylethyl]urea —— C15H18N2O2S
1-[(4-hydroxyphenyl)methyl]-1-methyl-3-[(1S)-1-thiophen-2-ylethyl]urea
—— 2-[[[(R)-furan-2-yl(phenyl)methyl]amino]methyl]-6-methoxyphenol —— C19H19NO3
2-[[[(R)-furan-2-yl(phenyl)methyl]amino]methyl]-6-methoxyphenol
—— (5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5E)-3-benzyl-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C18H15NO4S
(5E)-3-benzyl-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— 4-chloro-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H9ClN2O4
4-chloro-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 1-[(3S)-5-(3-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone —— C18H17ClN2O3
1-[(3S)-5-(3-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— 4-[(3S)-2-methylsulfonyl-5-phenyl-3,4-dihydropyrazol-3-yl]phenol —— C16H16N2O3S
4-[(3S)-2-methylsulfonyl-5-phenyl-3,4-dihydropyrazol-3-yl]phenol
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-(3-methylphenyl)-3,4-dihydropyrazol-2-yl]propan-1-one —— C20H22N2O3
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-(3-methylphenyl)-3,4-dihydropyrazol-2-yl]propan-1-one
—— 1-[(3R)-5-(3-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone —— C18H17ClN2O3
1-[(3R)-5-(3-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— 4-[(3R)-2-methylsulfonyl-5-phenyl-3,4-dihydropyrazol-3-yl]phenol —— C16H16N2O3S
4-[(3R)-2-methylsulfonyl-5-phenyl-3,4-dihydropyrazol-3-yl]phenol
—— 1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-(3-methylphenyl)-3,4-dihydropyrazol-2-yl]propan-1-one —— C20H22N2O3
1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-(3-methylphenyl)-3,4-dihydropyrazol-2-yl]propan-1-one
—— propan-2-yl (4R,5R,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4R,5R,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4R,5S,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4R,5S,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4S,5R,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4S,5R,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4R,5R,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4R,5R,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4S,5S,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4S,5S,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4R,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C19H24N2O6
propan-2-yl (4R,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4S,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C19H24N2O6
propan-2-yl (4S,5R,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4R,5S,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4R,5S,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4S,5S,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C19H24N2O6
propan-2-yl (4S,5S,6R)-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4S,5R,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4S,5R,6R)-6-hydroxy-4-(3-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— propan-2-yl (4S,5S,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate —— C18H22N2O5
propan-2-yl (4S,5S,6R)-6-hydroxy-4-(4-hydroxyphenyl)-6-methyl-3-oxo-2,4,5,7-tetrahydro-1H-indazole-5-carboxylate
—— [(4S)-2,2-dimethyloxan-4-yl]-[(4-hydroxy-3-methoxyphenyl)methyl]azanium —— C15H24NO3+
[(4S)-2,2-dimethyloxan-4-yl]-[(4-hydroxy-3-methoxyphenyl)methyl]azanium
—— (2S)-2-(5-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile —— C14H16BrN3O
(2S)-2-(5-bromo-2-hydroxyphenyl)-2-(3,5,5-trimethyl-4H-pyrazol-1-yl)acetonitrile
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile —— C23H22N2O4
(4R)-4-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-2-pyrrol-1-yl-6,8-dihydro-4H-chromene-3-carbonitrile
—— methyl (4S)-5-cyano-4-(4-hydroxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate —— C19H16N2O4
methyl (4S)-5-cyano-4-(4-hydroxyphenyl)-2-methyl-6-pyrrol-1-yl-4H-pyran-3-carboxylate
—— 2-[(4R)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-4-bromo-6-methoxyphenol —— C16H14BrN5O2
2-[(4R)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-4-bromo-6-methoxyphenol
—— 2-methoxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C22H23N3O5
2-methoxyethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— ethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-propyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C23H25N3O4
ethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-propyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— ethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-propyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C23H25N3O4
ethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-propyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— 2-(4-bromophenyl)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C15H12BrN3O4
2-(4-bromophenyl)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— propan-2-yl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate —— C23H25N3O5
propan-2-yl (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
—— 2-[[(3R)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]methyl]-6-methoxyphenol —— C23H22N2O2
2-[[(3R)-3,5-diphenyl-3,4-dihydropyrazol-2-yl]methyl]-6-methoxyphenol