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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
—— 3,4,5-trihydroxy-N'-[1-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide —— C16H16N2O6
3,4,5-trihydroxy-N'-[1-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide
—— 1-[(5-cyano-4-methyl-2,6-dioxopyridin-3-ylidene)methyl]-3-(2-hydroxy-4-nitrophenyl)urea —— C15H11N5O6
1-[(5-cyano-4-methyl-2,6-dioxopyridin-3-ylidene)methyl]-3-(2-hydroxy-4-nitrophenyl)urea
—— 3-[[(8-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)hydrazinylidene]methyl]-4-nitrophenol —— C17H13N7O3
3-[[(8-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)hydrazinylidene]methyl]-4-nitrophenol
—— N'-[(3-bromo-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C14H11BrN2O5
N'-[(3-bromo-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— (1S)-1-cyclopropyl-N-[2-[4-(2-methoxyethyl)phenoxy]ethyl]ethanamine —— C16H25NO2
(1S)-1-cyclopropyl-N-[2-[4-(2-methoxyethyl)phenoxy]ethyl]ethanamine
—— (1R)-1-cyclopropyl-N-[2-[4-(2-methoxyethyl)phenoxy]ethyl]ethanamine —— C16H25NO2
(1R)-1-cyclopropyl-N-[2-[4-(2-methoxyethyl)phenoxy]ethyl]ethanamine
—— 5-[(5-chloro-2-hydroxyanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C14H10ClN3O3
5-[(5-chloro-2-hydroxyanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 3,4,5-trihydroxy-N'-[(3-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide —— C14H12N2O6
3,4,5-trihydroxy-N'-[(3-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide
—— 6-[(2-hydroxy-5-methylanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one —— C14H12N2O4
6-[(2-hydroxy-5-methylanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one
—— 2,4-dibromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H8Br2N2O4
2,4-dibromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 6-[5-(4-hydroxy-3-methoxyphenyl)pyrazolidin-3-ylidene]cyclohexa-2,4-dien-1-one —— C16H16N2O3
6-[5-(4-hydroxy-3-methoxyphenyl)pyrazolidin-3-ylidene]cyclohexa-2,4-dien-1-one
—— 4-[(4-hydroxy-2-methylanilino)methylidene]-3-(trifluoromethyl)-1H-pyrazol-5-one —— C12H10F3N3O2
4-[(4-hydroxy-2-methylanilino)methylidene]-3-(trifluoromethyl)-1H-pyrazol-5-one
—— 2-(3,4-dimethylphenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one —— C20H21N3O2
2-(3,4-dimethylphenyl)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methylpyrazol-3-one
—— 4-bromo-2-[(2R,6S)-4-(4-ethylphenyl)-2-pyridin-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H22BrN3O
4-bromo-2-[(2R,6S)-4-(4-ethylphenyl)-2-pyridin-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6S)-2-(3-bromo-4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H19Br2FN2O
4-bromo-2-[(2R,6S)-2-(3-bromo-4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6S)-2-(3-bromo-4-fluorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C24H21BrClFN2O
2-[(2S,6S)-2-(3-bromo-4-fluorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-pyridin-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H22BrN3O
4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-pyridin-3-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-4-(4-bromophenyl)-2-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17Br2ClN2O
4-bromo-2-[(2S,6R)-4-(4-bromophenyl)-2-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-4-(4-chlorophenyl)-2-(3-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[(2R,6R)-4-(4-chlorophenyl)-2-(3-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2R,6R)-2-(3-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H20BrFN2O
4-bromo-2-[(2R,6R)-2-(3-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6S)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[(2S,6S)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2R,6R)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17Br2ClN2O
4-bromo-2-[(2R,6R)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6S)-4-(4-chlorophenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H20ClFN2O2
2-[(2R,6S)-4-(4-chlorophenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2R,6S)-4-(4-chlorophenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17BrClFN2O
4-bromo-2-[(2R,6S)-4-(4-chlorophenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6S)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H17BrCl2N2O
2-[(2R,6S)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 4-bromo-2-[(2R,6S)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17Br2ClN2O
4-bromo-2-[(2R,6S)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6R)-4-(3-bromophenyl)-2-(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H17Br2ClN2O
2-[(2S,6R)-4-(3-bromophenyl)-2-(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 4-bromo-2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(3-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H16Br3FN2O
4-bromo-2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(3-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6S)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17Br2ClN2O
4-bromo-2-[(2S,6S)-2-(4-bromophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6R)-2,4-bis(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol —— C22H17Br3N2O
2-[(2S,6R)-2,4-bis(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol
—— 2-[(2R,6S)-2-(3-bromo-4-methoxyphenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H22BrClN2O3
2-[(2R,6S)-2-(3-bromo-4-methoxyphenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2S,6R)-4-(3-bromophenyl)-2-(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17Br3N2O
4-bromo-2-[(2S,6R)-4-(3-bromophenyl)-2-(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6S)-4-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17BrClFN2O
4-bromo-2-[(2R,6S)-4-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H19BrClFN2O2
2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2R,6R)-2-(3-bromo-4-fluorophenyl)-4-(3-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H16Br3FN2O
4-bromo-2-[(2R,6R)-2-(3-bromo-4-fluorophenyl)-4-(3-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-chloro-2-[(2R,6R)-4-(4-ethylphenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22ClFN2O
4-chloro-2-[(2R,6R)-4-(4-ethylphenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2S,6S)-2-(3-bromo-4-fluorophenyl)-4-(3-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C22H16Br2ClFN2O
2-[(2S,6S)-2-(3-bromo-4-fluorophenyl)-4-(3-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 2-[(2S,6R)-4-(4-chlorophenyl)-2-(3-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[(2S,6R)-4-(4-chlorophenyl)-2-(3-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-hydroxy-5-nitro-N'-[(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide —— C14H10N4O7
2-hydroxy-5-nitro-N'-[(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide
—— 4-chloro-2-[(2S,6S)-2-(3-chlorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22Cl2N2O
4-chloro-2-[(2S,6S)-2-(3-chlorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-2,4-bis(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol —— C22H17Br3N2O
2-[(2R,6R)-2,4-bis(4-bromophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-bromophenol
—— 4-bromo-2-[(2S,6R)-2-(3-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22Br2N2O
4-bromo-2-[(2S,6R)-2-(3-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[(2R,6R)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2S,6S)-2-(3-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22Br2N2O
4-bromo-2-[(2S,6S)-2-(3-bromophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C23H19BrClFN2O2
2-[(2R,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-chlorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2S,6R)-4-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17BrClFN2O
4-bromo-2-[(2S,6R)-4-(4-chlorophenyl)-2-(4-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C23H19Br2FN2O
4-bromo-2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-(4-chlorophenyl)-2-(3-fluorophenyl)-6-(2-hydroxy-3-methoxyphenyl)-1,2,5,6-tetrahydropyrimidine —— C23H20ClFN2O2
4-(4-chlorophenyl)-2-(3-fluorophenyl)-6-(2-hydroxy-3-methoxyphenyl)-1,2,5,6-tetrahydropyrimidine
—— 4-chloro-2-[(2S,6S)-4-(4-ethylphenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C24H22ClFN2O
4-chloro-2-[(2S,6S)-4-(4-ethylphenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-chloro-2-[(2R,6R)-4-(4-ethylphenyl)-2-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C25H25ClN2O
4-chloro-2-[(2R,6R)-4-(4-ethylphenyl)-2-(4-methylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol