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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
—— (8R,8aS)-6-amino-8-(3,4-dihydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile —— C19H17N5O2
(8R,8aS)-6-amino-8-(3,4-dihydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile
—— ethyl 2-(5-bromo-2-hydroxy-3-methoxyphenyl)-4-hydroxy-1,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(2H)-carboxylate —— C19H20BrN3O5S
ethyl 2-(5-bromo-2-hydroxy-3-methoxyphenyl)-4-hydroxy-1,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(2H)-carboxylate
—— 4-[bis(2-methyl-1H-indol-3-yl)methyl]-2-bromo-6-methoxyphenol —— C26H23BrN2O2
4-[bis(2-methyl-1H-indol-3-yl)methyl]-2-bromo-6-methoxyphenol
—— 2,3,4a,8a-Tetrachloro-6-ethenyl-5-(4-hydroxy-2,6-dimethoxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C20H16Cl4O5
2,3,4a,8a-Tetrachloro-6-ethenyl-5-(4-hydroxy-2,6-dimethoxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— 2,3,4a,8a-Tetrachloro-5-(2-chloro-4-hydroxyphenyl)-6-ethenyl-5,8-dihydronaphthalene-1,4-dione —— C18H11Cl5O3
2,3,4a,8a-Tetrachloro-5-(2-chloro-4-hydroxyphenyl)-6-ethenyl-5,8-dihydronaphthalene-1,4-dione
—— [1-(2-hydroxy-5-methylphenyl)dodecylideneamino] N-phenylcarbamate —— C26H36N2O3
[1-(2-hydroxy-5-methylphenyl)dodecylideneamino] N-phenylcarbamate
—— 2-(4-hydroxy-3-nitrophenyl)-N-[2-(2-thiophen-3-ylethylsulfanyl)-1,3-benzothiazol-6-yl]acetamide —— C21H17N3O4S3
2-(4-hydroxy-3-nitrophenyl)-N-[2-(2-thiophen-3-ylethylsulfanyl)-1,3-benzothiazol-6-yl]acetamide
—— 5-[(2,6-Dimethylpiperidin-1-yl)iminomethyl]-2-methoxyphenol —— C15H22N2O2
5-[(2,6-Dimethylpiperidin-1-yl)iminomethyl]-2-methoxyphenol
—— 2-methoxy-5-[(1R)-2-[(4-methylphenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol —— C23H26N2O2
2-methoxy-5-[(1R)-2-[(4-methylphenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]phenol
—— 5-[(1S)-2-[(3-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H23ClN2O2
5-[(1S)-2-[(3-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 5-[(1S)-2-[(4-fluorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H23FN2O2
5-[(1S)-2-[(4-fluorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 5-[(1R)-2-[(2,5-difluorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H22F2N2O2
5-[(1R)-2-[(2,5-difluorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 5-[(1S)-2-[(3-fluorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H23FN2O2
5-[(1S)-2-[(3-fluorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 5-[(1S)-2-[(4-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H23ClN2O2
5-[(1S)-2-[(4-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 2-[[(1S)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H22F2N2O2
2-[[(1S)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 5-[(1R)-2-[(4-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H23ClN2O2
5-[(1R)-2-[(4-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 4-[[(1R)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol —— C22H22F2N2O2
4-[[(1R)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol
—— 3-[[(1R)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol —— C21H20F2N2O2
3-[[(1R)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol
—— 5-[(1S)-2-[(4-ethylphenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C24H28N2O2
5-[(1S)-2-[(4-ethylphenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 5-[(1R)-2-[(3-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H23ClN2O2
5-[(1R)-2-[(3-chlorophenyl)methyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 5-[(1R)-2-benzyl-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol —— C22H24N2O2
5-[(1R)-2-benzyl-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-1-yl]-2-methoxyphenol
—— 4-[[(1S)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol —— C22H22F2N2O2
4-[[(1S)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol
—— 2-[[(1S)-1-(2-chloro-5-nitrophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H22ClN3O4
2-[[(1S)-1-(2-chloro-5-nitrophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 3-[[(1S)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol —— C21H20F2N2O2
3-[[(1S)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol
—— 2-methoxy-6-[[(1S)-1-(2,4,6-trimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C25H30N2O2
2-methoxy-6-[[(1S)-1-(2,4,6-trimethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-[[(1R)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H22F2N2O2
2-[[(1R)-1-(3,4-difluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 4-[[(1R)-1-(3-methoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,3-diol —— C22H24N2O3
4-[[(1R)-1-(3-methoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,3-diol
—— 4-[[(1S)-1-(3-methoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,3-diol —— C22H24N2O3
4-[[(1S)-1-(3-methoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,3-diol
—— 2-[[(1R)-1-(4-ethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,4-diol —— C23H26N2O2
2-[[(1R)-1-(4-ethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,4-diol
—— 2-[[(1R)-1-(2,3-dimethoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C24H28N2O4
2-[[(1R)-1-(2,3-dimethoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 4-[[(1S)-1-(4-ethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol —— C24H28N2O2
4-[[(1S)-1-(4-ethylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol
—— 2-[[(1S)-1-(2,3-dimethoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C24H28N2O4
2-[[(1S)-1-(2,3-dimethoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 2-[[(1S)-1-(4-tert-butylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C26H32N2O2
2-[[(1S)-1-(4-tert-butylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 3-[[(1S)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol —— C21H21FN2O2
3-[[(1S)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol
—— 2-methoxy-5-[[(1R)-1-(4-methoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C23H26N2O3
2-methoxy-5-[[(1R)-1-(4-methoxyphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-[[(1S)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H23FN2O2
2-[[(1S)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 3-[[(1R)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol —— C21H21FN2O2
3-[[(1R)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]benzene-1,2-diol
—— [Anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;cobalt(2+);pyridine;hydroxide —— C20H22CoN4O3S+2
[Anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;cobalt(2+);pyridine;hydroxide
—— (4-Hydroxy-3,5-dimethoxyphenyl)methyl-[(4-methoxyphenyl)methyl]azanium —— C17H22NO4+
(4-Hydroxy-3,5-dimethoxyphenyl)methyl-[(4-methoxyphenyl)methyl]azanium
—— 2-[(1,3-Benzothiazol-2-ylhydrazinylidene)methyl]-4,6-dinitrophenol —— C14H9N5O5S
2-[(1,3-Benzothiazol-2-ylhydrazinylidene)methyl]-4,6-dinitrophenol
—— 2-methoxy-6-[[(1R)-1-(4-nitrophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C22H23N3O4
2-methoxy-6-[[(1R)-1-(4-nitrophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-[[(1S)-1-(3-chlorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H23ClN2O2
2-[[(1S)-1-(3-chlorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 2-[[(1R)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H23FN2O2
2-[[(1R)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 2-methoxy-6-[[(1S)-1-(3-nitrophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C22H23N3O4
2-methoxy-6-[[(1S)-1-(3-nitrophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-methoxy-4-[[(1S)-1-[4-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C23H23F3N2O2
2-methoxy-4-[[(1S)-1-[4-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-methoxy-6-[[(1R)-1-[4-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C23H23F3N2O2
2-methoxy-6-[[(1R)-1-[4-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-[[(1R)-1-(3,4-dichlorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H22Cl2N2O2
2-[[(1R)-1-(3,4-dichlorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 2-methoxy-6-[[(1S)-1-(4-methylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol —— C23H26N2O2
2-methoxy-6-[[(1S)-1-(4-methylphenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]phenol
—— 2-[[(1R)-1-(4-chlorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol —— C22H23ClN2O2
2-[[(1R)-1-(4-chlorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-6-methoxyphenol
—— 2-(4-cyanophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide —— C18H17N3O4
2-(4-cyanophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide