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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
—— (2R)-2-(3,4-dihydroxyphenyl)-2-(3-methylanilino)acetonitrile —— C15H14N2O2
(2R)-2-(3,4-dihydroxyphenyl)-2-(3-methylanilino)acetonitrile
—— (2R)-2-(4-chloroanilino)-2-(3,4-dihydroxyphenyl)acetonitrile —— C14H11ClN2O2
(2R)-2-(4-chloroanilino)-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2S)-2-(4-chloroanilino)-2-(3,4-dihydroxyphenyl)acetonitrile —— C14H11ClN2O2
(2S)-2-(4-chloroanilino)-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2S)-2-(4-bromoanilino)-2-(3,4-dihydroxyphenyl)acetonitrile —— C14H11BrN2O2
(2S)-2-(4-bromoanilino)-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2R)-2-(3,4-dihydroxyphenyl)-2-(4-fluoroanilino)acetonitrile —— C14H11FN2O2
(2R)-2-(3,4-dihydroxyphenyl)-2-(4-fluoroanilino)acetonitrile
—— (2S)-2-anilino-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile —— C16H16N2O
(2S)-2-anilino-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile
—— (2R)-2-anilino-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile —— C16H16N2O
(2R)-2-anilino-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile
—— (2R)-2-anilino-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C15H14N2O2
(2R)-2-anilino-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (2S)-2-(3,4-dihydroxyphenyl)-2-(4-methylanilino)acetonitrile —— C15H14N2O2
(2S)-2-(3,4-dihydroxyphenyl)-2-(4-methylanilino)acetonitrile
—— (2R)-2-anilino-2-(3-hydroxy-4-methoxyphenyl)acetonitrile —— C15H14N2O2
(2R)-2-anilino-2-(3-hydroxy-4-methoxyphenyl)acetonitrile
—— (2R)-2-(3,4-dihydroxyphenyl)-2-(4-methylanilino)acetonitrile —— C15H14N2O2
(2R)-2-(3,4-dihydroxyphenyl)-2-(4-methylanilino)acetonitrile
—— (2S)-2-anilino-2-(3-hydroxy-4-methoxyphenyl)acetonitrile —— C15H14N2O2
(2S)-2-anilino-2-(3-hydroxy-4-methoxyphenyl)acetonitrile
—— (2S)-2-anilino-2-(3,4-dihydroxyphenyl)acetonitrile —— C14H12N2O2
(2S)-2-anilino-2-(3,4-dihydroxyphenyl)acetonitrile
—— 2-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-4-(5-ethyl-1,3,4-thiadiazol-2-yl)-5-iminothiolan-3-one —— C16H14ClN3O3S2
2-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-4-(5-ethyl-1,3,4-thiadiazol-2-yl)-5-iminothiolan-3-one
—— 2-[3-[4-(dimethylamino)phenyl]-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol —— C18H21N3O
2-[3-[4-(dimethylamino)phenyl]-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol
—— 2-[3-(3-bromo-4-methoxyphenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol —— C17H17BrN2O2
2-[3-(3-bromo-4-methoxyphenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol
—— 4-methyl-2-(3-pyridin-2-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol —— C15H15N3O
4-methyl-2-(3-pyridin-2-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol
—— 2-[3-(3-ethoxy-4-methoxyphenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol —— C19H22N2O3
2-[3-(3-ethoxy-4-methoxyphenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2-chlorophenyl)imino-1,3-thiazolidin-4-one —— C17H12BrClN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2-chlorophenyl)imino-1,3-thiazolidin-4-one
—— 4-methyl-2-(3-thiophen-2-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol —— C14H14N2OS
4-methyl-2-(3-thiophen-2-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol
—— 3-[2-[(2-Hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]benzoic acid —— C15H14N2O4
3-[2-[(2-Hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]benzoic acid
—— 5-[(3-Bromo-4-hydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H10BrNO2S2
5-[(3-Bromo-4-hydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-methoxy-2-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C12H16N4O2
5-methoxy-2-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 2-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C11H14N4O
2-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 4-methyl-2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C12H16N4O
4-methyl-2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 5-methoxy-2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C12H16N4O2
5-methoxy-2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 4-[(3R)-3-(1H-1,2,4-triazol-5-ylmethylamino)butyl]phenol —— C13H18N4O
4-[(3R)-3-(1H-1,2,4-triazol-5-ylmethylamino)butyl]phenol
—— 5-methyl-2-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C12H16N4O
5-methyl-2-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 3-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C11H14N4O
3-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C11H14N4O
2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 4-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]benzene-1,3-diol —— C11H14N4O2
4-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]benzene-1,3-diol
—— 2-methoxy-4-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C12H16N4O2
2-methoxy-4-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]benzene-1,4-diol —— C11H14N4O2
2-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]benzene-1,4-diol
—— 4-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C11H14N4O
4-[(1S)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 4-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol —— C11H14N4O
4-[(1R)-1-(1H-1,2,4-triazol-5-ylmethylamino)ethyl]phenol
—— 3,4,5-trihydroxy-N-[(2-methylcyclohexylidene)amino]benzamide —— C14H18N2O4
3,4,5-trihydroxy-N-[(2-methylcyclohexylidene)amino]benzamide
—— 6-Methoxy-alpha-(2,4,6-trimethylphenylimino)-O-cresol —— C17H19NO2
6-Methoxy-alpha-(2,4,6-trimethylphenylimino)-O-cresol
—— 3,4,5-trihydroxy-N-[(5-methylthiophen-2-yl)methylideneamino]benzamide —— C13H12N2O4S
3,4,5-trihydroxy-N-[(5-methylthiophen-2-yl)methylideneamino]benzamide
—— propan-2-yl 2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23N3O7S
propan-2-yl 2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(5-Bromo-2-hydroxy-3-methoxyphenyl)-7-ethyl-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol —— C18H20BrN3O3S
2-(5-Bromo-2-hydroxy-3-methoxyphenyl)-7-ethyl-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol
—— 8a-bromo-7-ethenyl-8-(2-hydroxy-4-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19BrO4
8a-bromo-7-ethenyl-8-(2-hydroxy-4-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-[(2R)-2-methylpyrrolidin-1-yl]sulfonyl-2-nitrophenol —— C11H14N2O5S
4-[(2R)-2-methylpyrrolidin-1-yl]sulfonyl-2-nitrophenol
—— 4-(2-amino-4,10-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl)-2,6-dimethoxyphenol —— C17H17N5O3
4-(2-amino-4,10-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl)-2,6-dimethoxyphenol
—— 4-[(2S)-2-methylpyrrolidin-1-yl]sulfonyl-2-nitrophenol —— C11H14N2O5S
4-[(2S)-2-methylpyrrolidin-1-yl]sulfonyl-2-nitrophenol
—— 3-[(4-hydroxy-3-nitrophenyl)methylidene]-2,3-dihydro-1H-indol-2-one —— C15H10N2O4
3-[(4-hydroxy-3-nitrophenyl)methylidene]-2,3-dihydro-1H-indol-2-one
—— 2-bromo-N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H12Br2N2O3
2-bromo-N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— [5-(3,4-dimethoxyphenyl)-3-(2-hydroxy-4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl](phenyl)methanone —— C25H24N2O5
[5-(3,4-dimethoxyphenyl)-3-(2-hydroxy-4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl](phenyl)methanone
—— 3-[N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate —— C16H18N8O3
3-[N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate
—— 3-[(1S)-1-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol —— C13H17N3O
3-[(1S)-1-[[(1S)-1-(1H-pyrazol-5-yl)ethyl]amino]ethyl]phenol
—— 2-[5-[(3-bromophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C18H12BrN3O5S2
2-[5-[(3-bromophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide