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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-[(2-Chloro-4-fluorophenyl)methyl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H13ClFNO4S
3-[(2-Chloro-4-fluorophenyl)methyl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— Dimethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate —— C19H23NO7
Dimethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— 4-[(1S)-2-amino-1-hydroxyethyl]benzene-1,3-diol —— C8H11NO3
4-[(1S)-2-amino-1-hydroxyethyl]benzene-1,3-diol
—— 4-[(1R)-2-amino-1-hydroxyethyl]-2,6-dimethylphenol —— C10H15NO2
4-[(1R)-2-amino-1-hydroxyethyl]-2,6-dimethylphenol
—— 4-[(1S)-2-amino-1-hydroxyethyl]-2,6-dimethylphenol —— C10H15NO2
4-[(1S)-2-amino-1-hydroxyethyl]-2,6-dimethylphenol
—— 4-Bromo-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C23H20BrClN2O
4-Bromo-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 4-Bromo-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C23H21BrClN2O+
4-Bromo-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Chloro-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C23H21Cl2N2O+
4-Chloro-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 4-Chloro-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C23H20Cl2N2O
4-Chloro-2-[2-(4-chlorophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]furan-2-carboxamide —— C13H12N2O4
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]furan-2-carboxamide
—— Methyl 13-[(2-hydroxy-3-methoxyphenyl)methylidene]-9-methyl-14-oxo-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraene-16-carboxylate —— C23H20N2O6S
Methyl 13-[(2-hydroxy-3-methoxyphenyl)methylidene]-9-methyl-14-oxo-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraene-16-carboxylate
—— 2-N,4-N-bis[(3-hydroxy-4-methoxyphenyl)methylideneamino]-3,5-dimethyl-1H-pyrrole-2,4-dicarboxamide —— C24H25N5O6
2-N,4-N-bis[(3-hydroxy-4-methoxyphenyl)methylideneamino]-3,5-dimethyl-1H-pyrrole-2,4-dicarboxamide
—— 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N,5-diphenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C28H23N3O4S
2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N,5-diphenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 3-Cyclohexyl-1-ethyl-1-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]urea —— C17H26N2O3
3-Cyclohexyl-1-ethyl-1-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]urea
—— 3-(3,4-dihydroxyphenyl)-N-(thiophen-2-ylmethylideneamino)propanamide —— C14H14N2O3S
3-(3,4-dihydroxyphenyl)-N-(thiophen-2-ylmethylideneamino)propanamide
—— 2-(4-chloro-2-methylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide —— C18H19ClN2O4
2-(4-chloro-2-methylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide
—— 3-(3-Bromo-4-hydroxy-5-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile —— C17H14BrNO4S
3-(3-Bromo-4-hydroxy-5-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile
—— 3-(4-Hydroxyphenyl)-2-(2-methylpropane-2-sulfonyl)prop-2-enenitrile —— C13H15NO3S
3-(4-Hydroxyphenyl)-2-(2-methylpropane-2-sulfonyl)prop-2-enenitrile
—— 5-[[[2-Chloro-5-(trifluoromethyl)phenyl]hydrazinylidene]methyl]-2-methoxyphenol —— C15H12ClF3N2O2
5-[[[2-Chloro-5-(trifluoromethyl)phenyl]hydrazinylidene]methyl]-2-methoxyphenol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one —— C27H25BrN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(5-Bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-cyclohexyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H20BrN3O4S
5-[(5-Bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-cyclohexyl-2-phenylimino-1,3-thiazolidin-4-one
—— 5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(4-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C18H13Cl2NO4S
5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(4-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 5-[(5-Chloro-2-hydroxyphenyl)methylidene]-2-(3-chloro-2-methylphenyl)imino-3-ethyl-1,3-thiazolidin-4-one —— C19H16Cl2N2O2S
5-[(5-Chloro-2-hydroxyphenyl)methylidene]-2-(3-chloro-2-methylphenyl)imino-3-ethyl-1,3-thiazolidin-4-one
—— 2-(2-cyanophenoxy)-N-[(2-hydroxy-3-nitrophenyl)methylideneamino]acetamide —— C16H12N4O5
2-(2-cyanophenoxy)-N-[(2-hydroxy-3-nitrophenyl)methylideneamino]acetamide
—— 8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19ClO3
8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]-2-(7-methyl-4-oxo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-3-yl)acetamide —— C21H22N4O4S
N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]-2-(7-methyl-4-oxo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-3-yl)acetamide
—— N,N'-bis[(3-hydroxyphenyl)methylideneamino]octanediamide —— C22H26N4O4
N,N'-bis[(3-hydroxyphenyl)methylideneamino]octanediamide
—— N-[(3-hydroxyphenyl)methylideneamino]-2-imidazo[2,1-b][1,3]thiazol-6-ylacetamide —— C14H12N4O2S
N-[(3-hydroxyphenyl)methylideneamino]-2-imidazo[2,1-b][1,3]thiazol-6-ylacetamide
—— 4-cyano-N-[(3-hydroxyphenyl)methylideneamino]-5-oxo-1,4-dihydropyrazole-3-carboxamide —— C12H9N5O3
4-cyano-N-[(3-hydroxyphenyl)methylideneamino]-5-oxo-1,4-dihydropyrazole-3-carboxamide
—— 4-(2-amino-4,10-dihydro-1H-[1,3,5]triazino[1,2-a]benzimidazol-5-ium-4-yl)-2-methoxyphenol —— C16H16N5O2+
4-(2-amino-4,10-dihydro-1H-[1,3,5]triazino[1,2-a]benzimidazol-5-ium-4-yl)-2-methoxyphenol
—— 3,4,5-trihydroxy-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H14N2O6
3,4,5-trihydroxy-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 4-Benzylsulfanyl-2,6-dinitrophenol —— C13H10N2O5S
4-Benzylsulfanyl-2,6-dinitrophenol
—— N-(butan-2-ylideneamino)-3,4,5-trihydroxybenzamide —— C11H14N2O4
N-(butan-2-ylideneamino)-3,4,5-trihydroxybenzamide
—— 2-{(E)-[(4-chloro-2-methylphenyl)imino]methyl}-6-methoxyphenol —— C15H14ClNO2
2-{(E)-[(4-chloro-2-methylphenyl)imino]methyl}-6-methoxyphenol
—— 3,4,5-trihydroxy-N-(pentan-2-ylideneamino)benzamide —— C12H16N2O4
3,4,5-trihydroxy-N-(pentan-2-ylideneamino)benzamide
—— 3-(3,4-dihydroxyphenyl)-N-[(3-methoxy-4-phenylmethoxyphenyl)methylideneamino]propanamide —— C24H24N2O5
3-(3,4-dihydroxyphenyl)-N-[(3-methoxy-4-phenylmethoxyphenyl)methylideneamino]propanamide
—— 2-(4-Fluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13FN2O3S
2-(4-Fluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C27H25IN2O3S
3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (4R)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18ClN3O3S
(4R)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— 4-hydroxy-3-methoxy-N-[(4-phenylcyclohexylidene)amino]benzamide —— C20H22N2O3
4-hydroxy-3-methoxy-N-[(4-phenylcyclohexylidene)amino]benzamide
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-3,4-dimethylbenzamide —— C17H18N2O3
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-3,4-dimethylbenzamide
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methylphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C26H23N3O3
(4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methylphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— N-[1-[3-(cyclohexanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide —— C22H25N3O5
N-[1-[3-(cyclohexanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide
—— 2-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-[1,3]thiazolo[3,2-a]benzimidazol-1-one —— C17H11ClN2O3S
2-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-[1,3]thiazolo[3,2-a]benzimidazol-1-one
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methylphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C26H23N3O3
(4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methylphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H16N4O3S
(4R)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H16N4O3S
(4S)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H18N4O3S
(4S)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 2-[[(2R)-2-(5-ethyl-3-methyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-6-methoxyphenol —— C18H24N2O3
2-[[(2R)-2-(5-ethyl-3-methyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-6-methoxyphenol
—— 4-[[(2R)-2-(5-ethyl-3-methyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-2-methoxyphenol —— C18H24N2O3
4-[[(2R)-2-(5-ethyl-3-methyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-2-methoxyphenol