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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
—— (5Z)-2-(3-chlorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C21H19ClN2O3S
(5Z)-2-(3-chlorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C21H21ClN2O3S
(5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— (5E)-3-ethyl-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H19FN2O2S
(5E)-3-ethyl-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— prop-2-enyl (4S)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate —— C26H24ClN3O5S
prop-2-enyl (4S)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
—— (5E)-3-ethyl-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H19FN2O2S
(5E)-3-ethyl-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C17H12BrFN2O2S
(5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-ethyl-2-(2-fluorophenyl)imino-1,3-thiazolidin-4-one —— C18H14ClFN2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-ethyl-2-(2-fluorophenyl)imino-1,3-thiazolidin-4-one
—— (5E)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C21H19FN2O3S
(5E)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(2,4-difluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C21H20F2N2O3S
(5E)-2-(2,4-difluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— (5E)-3-ethyl-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1,3-thiazolidin-4-one —— C22H21FN2O3S
(5E)-3-ethyl-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H15FN2O3S
(5E)-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(2-fluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H15FN2O3S
(5E)-2-(2-fluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C19H17ClN2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-2-phenylimino-3-propyl-1,3-thiazolidin-4-one —— C19H18N2O2S
(5E)-5-[(4-hydroxyphenyl)methylidene]-2-phenylimino-3-propyl-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-2-(3-methylsulfanylphenyl)imino-1,3-thiazolidin-4-one —— C20H20N2O2S2
(5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-2-(3-methylsulfanylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-(3-methylsulfanylphenyl)imino-1,3-thiazolidin-4-one —— C19H18N2O3S2
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-(3-methylsulfanylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C21H19FN2O3S
(5E)-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-ethyl-2-phenylimino-1,3-thiazolidin-4-one —— C18H15ClN2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-ethyl-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one —— C17H14N2O2S
(5E)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-2-(3,4-dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C20H20N2O3S
(5E)-2-(3,4-dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(3,4-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C21H22N2O2S
(5E)-2-(3,4-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-3-ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C20H20N2O3S
(5E)-3-ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one —— C17H14N2O2S
(5E)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one
—— (4R)-4-(4-hydroxy-3,5-dimethylphenyl)-1,4-dimethyl-1,3-diazinan-2-one —— C14H20N2O2
(4R)-4-(4-hydroxy-3,5-dimethylphenyl)-1,4-dimethyl-1,3-diazinan-2-one
—— (5E)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C22H22N2O3S
(5E)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— (4S)-4-(4-hydroxy-3,5-dimethylphenyl)-1,4-dimethyl-1,3-diazinan-2-one —— C14H20N2O2
(4S)-4-(4-hydroxy-3,5-dimethylphenyl)-1,4-dimethyl-1,3-diazinan-2-one
—— 3-[(2S,5S)-2-phenyl-1,3-oxazolidin-5-yl]phenol —— C15H15NO2
3-[(2S,5S)-2-phenyl-1,3-oxazolidin-5-yl]phenol
—— 3-[(2R,5R)-2-phenyl-1,3-oxazolidin-5-yl]phenol —— C15H15NO2
3-[(2R,5R)-2-phenyl-1,3-oxazolidin-5-yl]phenol
—— 3-[(2R,5S)-2-phenyl-1,3-oxazolidin-5-yl]phenol —— C15H15NO2
3-[(2R,5S)-2-phenyl-1,3-oxazolidin-5-yl]phenol
—— methyl (E,4S)-4-(4-hydroxyphenoxy)pent-2-enoate —— C12H14O4
methyl (E,4S)-4-(4-hydroxyphenoxy)pent-2-enoate
—— 2-methoxy-5-[(Z)-[(2,3,4,5,6-pentafluorophenyl)hydrazinylidene]methyl]phenol —— C14H9F5N2O2
2-methoxy-5-[(Z)-[(2,3,4,5,6-pentafluorophenyl)hydrazinylidene]methyl]phenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-tert-butylbenzamide —— C19H21BrN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-tert-butylbenzamide
—— 3-[(4-tert-butylphenoxy)methyl]-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C21H24N4O3S
3-[(4-tert-butylphenoxy)methyl]-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— N-[(3-chloro-2-hydroxy-4-methylphenyl)methyl]-N-hydroxyacetamide —— C10H12ClNO3
N-[(3-chloro-2-hydroxy-4-methylphenyl)methyl]-N-hydroxyacetamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide —— C16H15BrN2O3S
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide
—— N-hydroxy-N-[(2-hydroxy-4,6-dimethylphenyl)methyl]acetamide —— C11H15NO3
N-hydroxy-N-[(2-hydroxy-4,6-dimethylphenyl)methyl]acetamide
—— N-hydroxy-N-[(2-hydroxy-4,5-dimethylphenyl)methyl]acetamide —— C11H15NO3
N-hydroxy-N-[(2-hydroxy-4,5-dimethylphenyl)methyl]acetamide
—— 2-methoxy-5-[(Z)-[[4-(4-methylphenyl)sulfonylphenyl]hydrazinylidene]methyl]phenol —— C21H20N2O4S
2-methoxy-5-[(Z)-[[4-(4-methylphenyl)sulfonylphenyl]hydrazinylidene]methyl]phenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3,5-dimethoxybenzamide —— C17H17BrN2O5
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3,5-dimethoxybenzamide
—— 2-methoxy-5-[(E)-2-(1-methylbenzimidazol-2-yl)-2-(4-methyl-1,3-thiazol-2-yl)ethenyl]phenol —— C21H19N3O2S
2-methoxy-5-[(E)-2-(1-methylbenzimidazol-2-yl)-2-(4-methyl-1,3-thiazol-2-yl)ethenyl]phenol
—— 5-[(E)-2-(1,3-benzoxazol-2-yl)-2-chloroethenyl]-2-methoxyphenol —— C16H12ClNO3
5-[(E)-2-(1,3-benzoxazol-2-yl)-2-chloroethenyl]-2-methoxyphenol
—— 4-[2-(4-Fluorophenyl)-1,3-thiazol-4-yl]benzene-1,3-diol —— C15H10FNO2S
4-[2-(4-Fluorophenyl)-1,3-thiazol-4-yl]benzene-1,3-diol
—— 2-[(S)-hydroxy-[(2S)-pyrrolidin-2-yl]methyl]-5-nitrophenol —— C11H14N2O4
2-[(S)-hydroxy-[(2S)-pyrrolidin-2-yl]methyl]-5-nitrophenol
—— 2-[(R)-hydroxy-[(2R)-pyrrolidin-2-yl]methyl]-5-nitrophenol —— C11H14N2O4
2-[(R)-hydroxy-[(2R)-pyrrolidin-2-yl]methyl]-5-nitrophenol
—— 2-[(S)-hydroxy-[(2R)-pyrrolidin-2-yl]methyl]-5-nitrophenol —— C11H14N2O4
2-[(S)-hydroxy-[(2R)-pyrrolidin-2-yl]methyl]-5-nitrophenol
—— 2-[(S)-hydroxy-[(3S)-piperidin-3-yl]methyl]-5-nitrophenol —— C12H16N2O4
2-[(S)-hydroxy-[(3S)-piperidin-3-yl]methyl]-5-nitrophenol
—— 2-[(R)-hydroxy-[(2S)-pyrrolidin-2-yl]methyl]-5-nitrophenol —— C11H14N2O4
2-[(R)-hydroxy-[(2S)-pyrrolidin-2-yl]methyl]-5-nitrophenol
—— 2-[(R)-hydroxy-[(3S)-piperidin-3-yl]methyl]-5-nitrophenol —— C12H16N2O4
2-[(R)-hydroxy-[(3S)-piperidin-3-yl]methyl]-5-nitrophenol
—— 4-bromo-2-[(7R)-1,4-oxazepan-7-yl]phenol —— C11H14BrNO2
4-bromo-2-[(7R)-1,4-oxazepan-7-yl]phenol
—— 5-bromo-2-[(5R)-1,4-oxazepan-5-yl]phenol —— C11H14BrNO2
5-bromo-2-[(5R)-1,4-oxazepan-5-yl]phenol