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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
—— 5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-[(3-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H10BrN3O7S
5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-[(3-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21ClO3
8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one —— C23H29BrN2O3S
5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one
—— 2-{[4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-yl]sulfanyl}-N-(2-methylphenyl)acetamide —— C22H20BrN3O4S
2-{[4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-yl]sulfanyl}-N-(2-methylphenyl)acetamide
—— 2-methylpropyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C31H36N2O7S
2-methylpropyl 5-(4-butoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O6S
propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C36H30N2O6S
benzyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O6S
prop-2-enyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C32H30N2O6S
propan-2-yl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-phenylmethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Hydroxy-(2-hydroxy-5-methylphenyl)methanesulfonate —— C8H9O5S-
Hydroxy-(2-hydroxy-5-methylphenyl)methanesulfonate
—— 5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-methylphenyl)-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C26H24N2O4S
5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-methylphenyl)-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— 2,3,4a,8a-Tetrachloro-6-ethenyl-5-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5,8-dihydronaphthalene-1,4-dione —— C21H16Cl4O4
2,3,4a,8a-Tetrachloro-6-ethenyl-5-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5,8-dihydronaphthalene-1,4-dione
—— 5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one —— C14H15BrN2O3S
5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-methylfuran-2-carboxamide —— C14H14N2O4
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-methylfuran-2-carboxamide
—— N-[1-(2,4-dimethylphenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C17H18N2O4
N-[1-(2,4-dimethylphenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 4-Bromo-2-[2-(2-methylphenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C24H23BrN2O
4-Bromo-2-[2-(2-methylphenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Methyl-2-(5-methyl-2-pyrrolidin-1-yl-1,3-thiazol-4-yl)-6-nitrophenol —— C15H17N3O3S
4-Methyl-2-(5-methyl-2-pyrrolidin-1-yl-1,3-thiazol-4-yl)-6-nitrophenol
—— ethyl 2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19N3O6S
ethyl 2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-pyridin-3-ylimino-1,3-thiazolidin-4-one —— C16H13N3O3S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-pyridin-3-ylimino-1,3-thiazolidin-4-one
—— 6-tert-butyl-3-[2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-4H-1,2,4-triazin-5-one —— C15H19N5O3
6-tert-butyl-3-[2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-4H-1,2,4-triazin-5-one
—— N-[2-[(2-hydroxy-5-nitrophenyl)methylideneamino]phenyl]adamantane-1-carboxamide —— C24H25N3O4
N-[2-[(2-hydroxy-5-nitrophenyl)methylideneamino]phenyl]adamantane-1-carboxamide
—— N-[1-(4-aminophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H15N3O4
N-[1-(4-aminophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 8a-bromo-7-ethenyl-8-(3-hydroxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H17BrO3
8a-bromo-7-ethenyl-8-(3-hydroxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2,4-dibromo-6-[(4H-1,2,4-triazol-4-ylamino)methyl]phenol —— C9H8Br2N4O
2,4-dibromo-6-[(4H-1,2,4-triazol-4-ylamino)methyl]phenol
—— N,N'-Dodecamethylenebis(2-hydroxy-3-methoxybenzylamine) —— C28H44N2O4
N,N'-Dodecamethylenebis(2-hydroxy-3-methoxybenzylamine)
—— 8a-bromo-7-ethenyl-8-(4-hydroxy-3-methylphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19BrO3
8a-bromo-7-ethenyl-8-(4-hydroxy-3-methylphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3-(2-Benzothiazolylamino)-5-nitrophenol —— C13H9N3O3S
3-(2-Benzothiazolylamino)-5-nitrophenol
—— 3-[(1R)-1-[(1-oxothian-4-yl)amino]ethyl]phenol —— C13H19NO2S
3-[(1R)-1-[(1-oxothian-4-yl)amino]ethyl]phenol
—— 4-[(3S)-3-[(1-oxothian-4-yl)amino]butyl]phenol —— C15H23NO2S
4-[(3S)-3-[(1-oxothian-4-yl)amino]butyl]phenol
—— 4-[(3R)-3-[(1-oxothian-4-yl)amino]butyl]phenol —— C15H23NO2S
4-[(3R)-3-[(1-oxothian-4-yl)amino]butyl]phenol
—— ethyl 2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-(3,4,5-trimethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25N3O9S
ethyl 2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-(3,4,5-trimethoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-fluoro-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H13FN2O3
3-fluoro-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-4-methyl-3-nitrobenzamide —— C16H15N3O5
N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-4-methyl-3-nitrobenzamide
—— 4-[[(4-Amino-5-ethyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-2-chloro-6-methoxyphenol —— C12H15ClN6O2
4-[[(4-Amino-5-ethyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-2-chloro-6-methoxyphenol
—— 5-[(5-Chloro-2-hydroxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one —— C22H27ClN2O2S
5-[(5-Chloro-2-hydroxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one
—— 5-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]-2-methoxyphenol —— C15H17NO2S
5-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]-2-methoxyphenol
—— 5-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]-2-methoxyphenol —— C15H17NO2S
5-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]-2-methoxyphenol
—— 3-[(1R)-1-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol —— C16H19NOS
3-[(1R)-1-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol
—— 3-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]-2,6-dimethylphenol —— C16H19NOS
3-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]-2,6-dimethylphenol
—— 3-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]-2,6-dimethylphenol —— C16H19NOS
3-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]-2,6-dimethylphenol
—— 5-[(3-Chloro-4-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C19H17ClN2O3S
5-[(3-Chloro-4-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— 3-[(1R)-1-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol —— C16H19NOS
3-[(1R)-1-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol
—— 2-Bromo-6-methoxy-4-(morpholinomethyl)phenol —— C12H16BrNO3
2-Bromo-6-methoxy-4-(morpholinomethyl)phenol
—— 3-[(1S)-1-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol —— C16H19NOS
3-[(1S)-1-[[(S)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol
—— 3-[(1S)-1-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol —— C16H19NOS
3-[(1S)-1-[[(R)-cyclopropyl(thiophen-2-yl)methyl]amino]ethyl]phenol
—— 3,4,5-trihydroxy-N-[(2-methylphenyl)methylideneamino]benzamide —— C15H14N2O4
3,4,5-trihydroxy-N-[(2-methylphenyl)methylideneamino]benzamide
—— N-(2-adamantylideneamino)-3,4,5-trihydroxybenzamide —— C17H20N2O4
N-(2-adamantylideneamino)-3,4,5-trihydroxybenzamide
—— 4-(5-Phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)benzene-1,3-diol —— C14H12N2O2S
4-(5-Phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)benzene-1,3-diol
—— 2-(4-Chlorophenyl)sulfonyl-3-(2-hydroxy-5-methoxyphenyl)prop-2-enenitrile —— C16H12ClNO4S
2-(4-Chlorophenyl)sulfonyl-3-(2-hydroxy-5-methoxyphenyl)prop-2-enenitrile
—— 2-[(4-hydroxyphenyl)methylideneamino]-6-methyl-4H-1,3,4-thiadiazin-5-one —— C11H11N3O2S
2-[(4-hydroxyphenyl)methylideneamino]-6-methyl-4H-1,3,4-thiadiazin-5-one