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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
—— Cycloheptyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C20H25BrN2O5
Cycloheptyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— ethyl 2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O6S
ethyl 2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-3-propyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H13NO3S2
5-[(3,4-Dihydroxyphenyl)methylidene]-3-propyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— methyl (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate —— C15H15NO5
methyl (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate
—— 5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione —— C14H15NO5S
5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione
—— (2-Hydroxy-3,5-dinitrophenyl)mercury —— C6H3HgN2O5
(2-Hydroxy-3,5-dinitrophenyl)mercury
—— 3-(3,4-Dichlorophenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H13Cl2NO4S2
3-(3,4-Dichlorophenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5,11,17,23-Tetrakis(1-methylcyclopentyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol —— C52H64O4
5,11,17,23-Tetrakis(1-methylcyclopentyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 2-(1,3-Benzothiazol-2-yl)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(4-methylphenyl)sulfanylmethyl]pyrazol-3-one —— C26H21N3O3S2
2-(1,3-Benzothiazol-2-yl)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-[(4-methylphenyl)sulfanylmethyl]pyrazol-3-one
—— (3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)(2-hydroxy-3-methoxyphenyl)acetonitrile —— C24H21N3O2
(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)(2-hydroxy-3-methoxyphenyl)acetonitrile
—— 3-benzyl-2-(4-hydroxy-3-methoxyphenyl)thiazolidin-4-one —— C17H17NO3S
3-benzyl-2-(4-hydroxy-3-methoxyphenyl)thiazolidin-4-one
—— 4-[(2-Hydroxy-5-nitrophenyl)methylidene]-3-(4-pentoxyphenyl)-1,2-oxazol-5-one —— C21H20N2O6
4-[(2-Hydroxy-5-nitrophenyl)methylidene]-3-(4-pentoxyphenyl)-1,2-oxazol-5-one
—— 2-Ethyl-5-[(2-hydroxy-5-nitrophenyl)amino]-5-oxopentanoic acid —— C13H16N2O6
2-Ethyl-5-[(2-hydroxy-5-nitrophenyl)amino]-5-oxopentanoic acid
—— 2-bromo-N-[(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide —— C14H10BrN3O4
2-bromo-N-[(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide
—— 2-(Azepan-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O3S
2-(Azepan-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (4R)-1-(6-ethoxy-1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C24H24N4O5S
(4R)-1-(6-ethoxy-1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(6-ethoxy-1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C24H24N4O5S
(4S)-1-(6-ethoxy-1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H18N4O4S
(4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C23H22N4O5S
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C22H20N4O5S
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C22H20N4O5S
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H19N7O4
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H19N7O4
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 2-methoxy-6-[[(2S)-2-(4-methoxyphenyl)azepan-1-yl]methyl]phenol —— C21H27NO3
2-methoxy-6-[[(2S)-2-(4-methoxyphenyl)azepan-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2S)-2-(3-methylphenyl)azepan-1-yl]methyl]phenol —— C21H27NO2
2-methoxy-6-[[(2S)-2-(3-methylphenyl)azepan-1-yl]methyl]phenol
—— 2-[5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-methylphenyl)acetamide —— C20H17BrN2O5S
2-[5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-methylphenyl)acetamide
—— 2-methoxy-6-[[(2R)-2-(4-methylphenyl)azepan-1-yl]methyl]phenol —— C21H27NO2
2-methoxy-6-[[(2R)-2-(4-methylphenyl)azepan-1-yl]methyl]phenol
—— 2-methoxy-4-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
2-methoxy-4-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
2-methoxy-5-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2R)-2-(4-methylphenyl)azepan-1-yl]methyl]phenol —— C21H27NO2
2-methoxy-5-[[(2R)-2-(4-methylphenyl)azepan-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2S)-2-(3-methylthiophen-2-yl)azepan-1-yl]methyl]phenol —— C19H25NO2S
2-methoxy-6-[[(2S)-2-(3-methylthiophen-2-yl)azepan-1-yl]methyl]phenol
—— 2-methoxy-4-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
2-methoxy-4-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-[[(2S)-2-(3-fluorophenyl)azepan-1-yl]methyl]-6-methoxyphenol —— C20H24FNO2
2-[[(2S)-2-(3-fluorophenyl)azepan-1-yl]methyl]-6-methoxyphenol
—— 2-methoxy-6-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
2-methoxy-6-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2R)-2-(3-methylthiophen-2-yl)azepan-1-yl]methyl]phenol —— C19H25NO2S
2-methoxy-5-[[(2R)-2-(3-methylthiophen-2-yl)azepan-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
2-methoxy-6-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2S)-2-(5-methylthiophen-2-yl)azepan-1-yl]methyl]phenol —— C19H25NO2S
2-methoxy-5-[[(2S)-2-(5-methylthiophen-2-yl)azepan-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2R)-2-(5-methylthiophen-2-yl)azepan-1-yl]methyl]phenol —— C19H25NO2S
2-methoxy-5-[[(2R)-2-(5-methylthiophen-2-yl)azepan-1-yl]methyl]phenol
—— 5-[[(2R)-2-(3-fluorophenyl)azepan-1-yl]methyl]-2-methoxyphenol —— C20H24FNO2
5-[[(2R)-2-(3-fluorophenyl)azepan-1-yl]methyl]-2-methoxyphenol
—— 2-methoxy-5-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
2-methoxy-5-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2R)-2-(3-methylphenyl)azepan-1-yl]methyl]phenol —— C21H27NO2
2-methoxy-6-[[(2R)-2-(3-methylphenyl)azepan-1-yl]methyl]phenol
—— 2,6-dimethoxy-4-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C19H25NO3S
2,6-dimethoxy-4-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2R)-2-(4-methoxyphenyl)azepan-1-yl]methyl]phenol —— C21H27NO3
2-methoxy-6-[[(2R)-2-(4-methoxyphenyl)azepan-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2S)-2-(4-methylphenyl)azepan-1-yl]methyl]phenol —— C21H27NO2
2-methoxy-5-[[(2S)-2-(4-methylphenyl)azepan-1-yl]methyl]phenol
—— 5-methoxy-2-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C18H23NO2S
5-methoxy-2-[[(2R)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2,6-dimethoxy-4-[[(2R)-2-(3-methylphenyl)azepan-1-yl]methyl]phenol —— C22H29NO3
2,6-dimethoxy-4-[[(2R)-2-(3-methylphenyl)azepan-1-yl]methyl]phenol
—— (7R)-2-ethylsulfanyl-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H25N5O4S
(7R)-2-ethylsulfanyl-7-(4-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 3-(2,4-Dimethylphenyl)-5-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H16INO3S2
3-(2,4-Dimethylphenyl)-5-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— methyl 2-anilino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C20H17NO5S
methyl 2-anilino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 4-fluoro-N-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide —— C18H13FN2O4S2
4-fluoro-N-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]benzamide