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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
—— 4-hydroxy-2-(4-hydroxy-3,5-dinitrophenyl)sulfanyl-1H-pyrimidin-6-one —— C10H6N4O7S
4-hydroxy-2-(4-hydroxy-3,5-dinitrophenyl)sulfanyl-1H-pyrimidin-6-one
—— 2-hydroxy-N-(2-hydroxy-5-nitrophenyl)-2-phenylacetamide —— C14H12N2O5
2-hydroxy-N-(2-hydroxy-5-nitrophenyl)-2-phenylacetamide
—— Methyl 4-[(3-hydroxyphenyl)methylidene]-1-(2-methoxyethyl)-2-methyl-5-oxopyrrole-3-carboxylate —— C17H19NO5
Methyl 4-[(3-hydroxyphenyl)methylidene]-1-(2-methoxyethyl)-2-methyl-5-oxopyrrole-3-carboxylate
—— Methyl 4-[(4-hydroxyphenyl)methylidene]-1-(2-methoxyethyl)-2-methyl-5-oxopyrrole-3-carboxylate —— C17H19NO5
Methyl 4-[(4-hydroxyphenyl)methylidene]-1-(2-methoxyethyl)-2-methyl-5-oxopyrrole-3-carboxylate
—— 5-[[(2,4-Dinitrophenyl)-methylhydrazinylidene]methyl]-2-methoxyphenol —— C15H14N4O6
5-[[(2,4-Dinitrophenyl)-methylhydrazinylidene]methyl]-2-methoxyphenol
—— 8a-bromo-8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H16BrClO3
8a-bromo-8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-[(4-hydroxy-3-methoxyphenyl)-(5-oxo-1,3-diphenyl-4H-pyrazol-4-yl)methyl]-2,5-diphenyl-4H-pyrazol-3-one —— C38H30N4O4
4-[(4-hydroxy-3-methoxyphenyl)-(5-oxo-1,3-diphenyl-4H-pyrazol-4-yl)methyl]-2,5-diphenyl-4H-pyrazol-3-one
—— ethyl 2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O6S
ethyl 2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-2-(cyclopropylmethylamino)-2-(4-hydroxyphenyl)acetonitrile —— C12H14N2O
(2R)-2-(cyclopropylmethylamino)-2-(4-hydroxyphenyl)acetonitrile
—— (2S)-2-(cyclopropylmethylamino)-4-(4-hydroxyphenyl)-2-methylbutanenitrile —— C15H20N2O
(2S)-2-(cyclopropylmethylamino)-4-(4-hydroxyphenyl)-2-methylbutanenitrile
—— Diethyl 4-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate —— C23H29NO7
Diethyl 4-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— (2R)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(cyclopropylmethylamino)acetonitrile —— C13H15BrN2O2
(2R)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(cyclopropylmethylamino)acetonitrile
—— (2R)-2-(cyclopropylmethylamino)-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C13H16N2O2
(2R)-2-(cyclopropylmethylamino)-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (2R)-2-(cyclopropylmethylamino)-2-(3,4-dihydroxyphenyl)acetonitrile —— C12H14N2O2
(2R)-2-(cyclopropylmethylamino)-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2S)-2-(cyclopropylmethylamino)-2-(3-hydroxyphenyl)acetonitrile —— C12H14N2O
(2S)-2-(cyclopropylmethylamino)-2-(3-hydroxyphenyl)acetonitrile
—— (2R)-2-(cyclopropylmethylamino)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile —— C13H16N2O2
(2R)-2-(cyclopropylmethylamino)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile
—— diethyl 4-(3-hydroxyphenyl)-6-methyl-2-methylidene-3,4-dihydro-1H-pyridine-3,5-dicarboxylate —— C19H23NO5
diethyl 4-(3-hydroxyphenyl)-6-methyl-2-methylidene-3,4-dihydro-1H-pyridine-3,5-dicarboxylate
—— (2S)-2-(cyclopropylmethylamino)-2-(3,4-dihydroxyphenyl)acetonitrile —— C12H14N2O2
(2S)-2-(cyclopropylmethylamino)-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2R)-2-(cyclopropylmethylamino)-4-(4-hydroxyphenyl)-2-methylbutanenitrile —— C15H20N2O
(2R)-2-(cyclopropylmethylamino)-4-(4-hydroxyphenyl)-2-methylbutanenitrile
—— 2-{[4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-cyano-6-hydroxy-4,5-dihydropyridin-2-yl]sulfanyl}-N-(4-fluorophenyl)acetamide —— C21H17BrFN3O4S
2-{[4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-cyano-6-hydroxy-4,5-dihydropyridin-2-yl]sulfanyl}-N-(4-fluorophenyl)acetamide
—— (2R)-2-(cyclopropylmethylamino)-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile —— C14H18N2O
(2R)-2-(cyclopropylmethylamino)-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile
—— (2S)-2-(cyclopropylmethylamino)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile —— C13H16N2O2
(2S)-2-(cyclopropylmethylamino)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile
—— 3-(2-Aminoethyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C13H14N2O4S
3-(2-Aminoethyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 2-[5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]ethylazanium —— C13H15N2O4S+
2-[5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]ethylazanium
—— 3-Benzyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C19H17NO3S
3-Benzyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 2-[5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid —— C13H13NO6S3
2-[5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanesulfonic acid
—— 5-[(5-Chloro-2-hydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one —— C18H15ClN2O2S
5-[(5-Chloro-2-hydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (2S)-2-[2-(diethylamino)ethylamino]-2-(3,4-dihydroxyphenyl)acetonitrile —— C14H21N3O2
(2S)-2-[2-(diethylamino)ethylamino]-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2S)-2-[2-(diethylamino)ethylamino]-2-(3-hydroxyphenyl)acetonitrile —— C14H21N3O
(2S)-2-[2-(diethylamino)ethylamino]-2-(3-hydroxyphenyl)acetonitrile
—— (2S)-2-[2-(diethylamino)ethylamino]-2-(4-hydroxyphenyl)acetonitrile —— C14H21N3O
(2S)-2-[2-(diethylamino)ethylamino]-2-(4-hydroxyphenyl)acetonitrile
—— (2R)-2-[2-(diethylamino)ethylamino]-2-(4-hydroxyphenyl)acetonitrile —— C14H21N3O
(2R)-2-[2-(diethylamino)ethylamino]-2-(4-hydroxyphenyl)acetonitrile
—— (2S)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-[2-(dimethylamino)ethylamino]acetonitrile —— C13H18BrN3O2
(2S)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-[2-(dimethylamino)ethylamino]acetonitrile
—— (2S)-2-[2-(dimethylamino)ethylamino]-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile —— C14H21N3O
(2S)-2-[2-(dimethylamino)ethylamino]-2-(4-hydroxy-3,5-dimethylphenyl)acetonitrile
—— (2S)-2-(1,4-diazepan-1-yl)-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C14H19N3O2
(2S)-2-(1,4-diazepan-1-yl)-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (2S)-2-(1,4-diazepan-1-yl)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile —— C14H19N3O2
(2S)-2-(1,4-diazepan-1-yl)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile
—— 5-methoxy-2-[[(3-propan-2-yl-1H-benzimidazol-3-ium-2-yl)amino]methyl]phenol —— C18H22N3O2+
5-methoxy-2-[[(3-propan-2-yl-1H-benzimidazol-3-ium-2-yl)amino]methyl]phenol
—— (2S)-2-(4-hydroxy-3-methoxyphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile —— C14H18N2O3
(2S)-2-(4-hydroxy-3-methoxyphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile
—— 2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C28H22N4O6S
2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— (2R)-2-(4-hydroxy-3,5-dimethylphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile —— C15H20N2O2
(2R)-2-(4-hydroxy-3,5-dimethylphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile
—— (2R)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-[2-(dimethylamino)ethylamino]acetonitrile —— C13H18BrN3O2
(2R)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-[2-(dimethylamino)ethylamino]acetonitrile
—— (2R)-2-(3,4-dihydroxyphenyl)-2-[2-(dimethylamino)ethylamino]acetonitrile —— C12H17N3O2
(2R)-2-(3,4-dihydroxyphenyl)-2-[2-(dimethylamino)ethylamino]acetonitrile
—— (2R)-2-[2-(dimethylamino)ethylamino]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C13H19N3O2
(2R)-2-[2-(dimethylamino)ethylamino]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (2S)-2-[2-(dimethylamino)ethylamino]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C13H19N3O2
(2S)-2-[2-(dimethylamino)ethylamino]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (2R)-2-(1,4-diazepan-1-yl)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile —— C14H19N3O2
(2R)-2-(1,4-diazepan-1-yl)-2-(3-hydroxy-4-methoxyphenyl)acetonitrile
—— (2R)-2-(1,4-diazepan-1-yl)-2-(3,4-dihydroxyphenyl)acetonitrile —— C13H17N3O2
(2R)-2-(1,4-diazepan-1-yl)-2-(3,4-dihydroxyphenyl)acetonitrile
—— (2S)-2-(4-hydroxy-3,5-dimethylphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile —— C15H20N2O2
(2S)-2-(4-hydroxy-3,5-dimethylphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile
—— (2S)-2-(4-hydroxyphenyl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile —— C13H16N2O2
(2S)-2-(4-hydroxyphenyl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile
—— (2S)-2-(4-hydroxyphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile —— C13H16N2O2
(2S)-2-(4-hydroxyphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile
—— (2S)-2-(3-hydroxyphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile —— C13H16N2O2
(2S)-2-(3-hydroxyphenyl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile
—— (2S)-2-(3-hydroxy-4-methoxyphenyl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile —— C14H18N2O3
(2S)-2-(3-hydroxy-4-methoxyphenyl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile