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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
—— propyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19BrN2O5
propyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3S)-3-methylpiperazin-1-yl]propanoate —— C17H23F3N2O5
methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3S)-3-methylpiperazin-1-yl]propanoate
—— methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxyphenyl)propanoate —— C10H9F3O4
methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxyphenyl)propanoate
—— methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3S)-3-methylpiperazine-1,4-diium-1-yl]propanoate —— C17H25F3N2O5+2
methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3S)-3-methylpiperazine-1,4-diium-1-yl]propanoate
—— (5S)-5-(4-hydroxy-3-methoxyphenyl)-11-methyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C17H20N3O3S+
(5S)-5-(4-hydroxy-3-methoxyphenyl)-11-methyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— propyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19BrN2O5
propyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (5R)-5-(4-hydroxy-3-methoxyphenyl)-11-methyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C17H20N3O3S+
(5R)-5-(4-hydroxy-3-methoxyphenyl)-11-methyl-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— propyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17N3O6
propyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— prop-2-enyl (4R)-3-cyano-2-ethylsulfanyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3,4-dihydropyridine-5-carboxylate —— C20H22N2O4S
prop-2-enyl (4R)-3-cyano-2-ethylsulfanyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3,4-dihydropyridine-5-carboxylate
—— prop-2-enyl (4S)-3-cyano-2-ethylsulfanyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3,4-dihydropyridine-5-carboxylate —— C20H22N2O4S
prop-2-enyl (4S)-3-cyano-2-ethylsulfanyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3,4-dihydropyridine-5-carboxylate
—— 2-Methoxy-4-[[(3-nitropyridin-1-ium-4-yl)amino]methyl]phenol —— C13H14N3O4+
2-Methoxy-4-[[(3-nitropyridin-1-ium-4-yl)amino]methyl]phenol
—— 1-[(2S)-2-(5-bromo-2-hydroxyphenyl)-5-(3-bromophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C16H12Br2N2O3
1-[(2S)-2-(5-bromo-2-hydroxyphenyl)-5-(3-bromophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 5-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-2-[[(2S,6S)-2,6-dimethylmorpholin-4-yl]methyl]benzene-1,4-diol —— C20H32N2O4
5-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-2-[[(2S,6S)-2,6-dimethylmorpholin-4-yl]methyl]benzene-1,4-diol
—— 1-[(2R)-2-(5-bromo-2-hydroxyphenyl)-5-(3-bromophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C16H12Br2N2O3
1-[(2R)-2-(5-bromo-2-hydroxyphenyl)-5-(3-bromophenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 2,5-bis[[(2S,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]benzene-1,4-diol —— C20H34N2O4+2
2,5-bis[[(2S,6R)-2,6-dimethylmorpholin-4-ium-4-yl]methyl]benzene-1,4-diol
—— 2,5-bis[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]benzene-1,4-diol —— C20H32N2O4
2,5-bis[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]benzene-1,4-diol
—— (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C22H21NO7S2
(7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C22H21NO7S2
(7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO6S2
(7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO5S2
(7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C22H21NO6S2
(7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO6S2
(7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C21H16FNO5S
(7S)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7S)-3-(benzenesulfonyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H17NO5S2
(7S)-3-(benzenesulfonyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO5S2
(7S)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-3-(benzenesulfonyl)-7-(4-hydroxy-3-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H17NO5S2
(7S)-3-(benzenesulfonyl)-7-(4-hydroxy-3-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO5S2
(7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-3-(benzenesulfonyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO6S2
(7R)-3-(benzenesulfonyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C22H21NO6S2
(7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO5S2
(7R)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)sulfonyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-3-(benzenesulfonyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO6S2
(7S)-3-(benzenesulfonyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-3-(3-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C21H16FNO5S
(7R)-3-(3-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7R)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C21H16FNO5S
(7R)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7S)-3-(3-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C21H16FNO5S
(7S)-3-(3-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7R)-3-(benzenesulfonyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H17NO5S2
(7R)-3-(benzenesulfonyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C22H19NO5S
(7R)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— methyl (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate —— C15H15NO5
methyl (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-4-oxo-3H-pyrrole-3-carboxylate
—— (7S)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C22H19NO5S
(7S)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C23H21NO6S
(7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C22H19NO5S
(7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C23H21NO6S
(7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C22H19NO5S
(7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7S)-3-(4-chlorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C21H16ClNO5S
(7S)-3-(4-chlorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— (7R)-3-(4-chlorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid —— C21H16ClNO5S
(7R)-3-(4-chlorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-oxo-6,7-dihydro-4H-thieno[3,2-b]pyridine-2-carboxylic acid
—— 1,3-benzodioxol-5-ylmethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H19BrN2O7
1,3-benzodioxol-5-ylmethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-cyanoethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H17N3O5
2-cyanoethyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methylsulfanylethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17N3O6S
2-methylsulfanylethyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-methylsulfanylethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H20N2O5S
2-methylsulfanylethyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-propan-2-yloxyethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C18H23BrN2O6
2-propan-2-yloxyethyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 1,3-benzodioxol-5-ylmethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H19BrN2O7
1,3-benzodioxol-5-ylmethyl (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate