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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
—— (5E)-5-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrN2O5S
(5E)-5-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— (5Z)-3-(2-chloro-4-fluorobenzyl)-5-(3-hydroxy-4-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C18H13ClFNO4S
(5Z)-3-(2-chloro-4-fluorobenzyl)-5-(3-hydroxy-4-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— (6E)-4-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C15H14BrNO3
(6E)-4-bromo-6-[(2-hydroxy-5-methylanilino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N,5-diphenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C28H23N3O4S
(2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N,5-diphenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 3-(3,4-dihydroxyphenyl)-N-[(Z)-thiophen-2-ylmethylideneamino]propanamide —— C14H14N2O3S
3-(3,4-dihydroxyphenyl)-N-[(Z)-thiophen-2-ylmethylideneamino]propanamide
—— 2-N,4-N-bis[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3,5-dimethyl-1H-pyrrole-2,4-dicarboxamide —— C24H25N5O6
2-N,4-N-bis[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3,5-dimethyl-1H-pyrrole-2,4-dicarboxamide
—— (3-Hydroxy-5-methylphenyl)propanedinitrile —— C10H8N2O
(3-Hydroxy-5-methylphenyl)propanedinitrile
—— 5-[(Z)-[[2-chloro-5-(trifluoromethyl)phenyl]hydrazinylidene]methyl]-2-methoxyphenol —— C15H12ClF3N2O2
5-[(Z)-[[2-chloro-5-(trifluoromethyl)phenyl]hydrazinylidene]methyl]-2-methoxyphenol
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one —— C27H25BrN2O3S
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(4-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C18H13Cl2NO4S
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(4-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 4-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C16H19N3O4
4-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— N-[(Z)-(3-hydroxyphenyl)methylideneamino]-2-imidazo[2,1-b][1,3]thiazol-6-ylacetamide —— C14H12N4O2S
N-[(Z)-(3-hydroxyphenyl)methylideneamino]-2-imidazo[2,1-b][1,3]thiazol-6-ylacetamide
—— 3,4,5-trihydroxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H14N2O6
3,4,5-trihydroxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— N-[(Z)-1-[3-(cyclohexanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide —— C22H25N3O5
N-[(Z)-1-[3-(cyclohexanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide
—— (2E,5Z)-2-[(4-fluorophenyl)imino]-5-(2-hydroxy-3-methoxybenzylidene)-1,3-thiazolidin-4-one —— C17H13FN2O3S
(2E,5Z)-2-[(4-fluorophenyl)imino]-5-(2-hydroxy-3-methoxybenzylidene)-1,3-thiazolidin-4-one
—— (2Z)-2-(3-chloro-4-hydroxy-5-methoxybenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one —— C17H11ClN2O3S
(2Z)-2-(3-chloro-4-hydroxy-5-methoxybenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— 2-(2-Iodoethyl)-5-methylbenzene-1,4-diol —— C9H11IO2
2-(2-Iodoethyl)-5-methylbenzene-1,4-diol
—— 3,5-Dimethyl-2-[(methylamino)methyl]benzene-1,4-diol —— C10H15NO2
3,5-Dimethyl-2-[(methylamino)methyl]benzene-1,4-diol
—— 2-(2-Bromoethyl)-5-octylbenzene-1,4-diol —— C16H25BrO2
2-(2-Bromoethyl)-5-octylbenzene-1,4-diol
—— N-[(Z)-(2-chloro-6-fluorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H10ClFN2O4
N-[(Z)-(2-chloro-6-fluorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 3,4,5-trihydroxy-N'-[(1Z)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethyl]benzohydrazide —— C15H14N2O7
3,4,5-trihydroxy-N'-[(1Z)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethyl]benzohydrazide
—— (4Z)-1-(4-chlorophenyl)-4-[(3,5-dibromo-2-hydroxyphenyl)methylidene]pyrazolidine-3,5-dione —— C16H9Br2ClN2O3
(4Z)-1-(4-chlorophenyl)-4-[(3,5-dibromo-2-hydroxyphenyl)methylidene]pyrazolidine-3,5-dione
—— Ethyl (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-[2-(propan-2-yloxy)phenyl]-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C27H28N2O6S
Ethyl (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-[2-(propan-2-yloxy)phenyl]-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— (E)-1-(4-Hydroxy-3-methoxyphenyl)hexadec-3-en-5-one —— C23H36O3
(E)-1-(4-Hydroxy-3-methoxyphenyl)hexadec-3-en-5-one
—— (S)-1-(4-Hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl acetate —— C19H28O5
(S)-1-(4-Hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl acetate
—— (E)-1-(4-Hydroxy-3-methoxyphenyl)dodec-3-en-5-one —— C19H28O3
(E)-1-(4-Hydroxy-3-methoxyphenyl)dodec-3-en-5-one
—— 5-(1,3-dihydrobenzimidazol-2-ylidene)-6-(4-hydroxy-3-methoxyphenyl)-4-phenyl-1,6-dihydropyrimidin-2-one —— C24H20N4O3
5-(1,3-dihydrobenzimidazol-2-ylidene)-6-(4-hydroxy-3-methoxyphenyl)-4-phenyl-1,6-dihydropyrimidin-2-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(4-methoxy-N-methylanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H20N2O4S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[(4-methoxy-N-methylanilino)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 1-[(Z)-[1-(4-fluorophenyl)-3-methyl-5-oxopyrazol-4-ylidene]methyl]-3-(2-hydroxy-5-nitrophenyl)urea —— C18H14FN5O5
1-[(Z)-[1-(4-fluorophenyl)-3-methyl-5-oxopyrazol-4-ylidene]methyl]-3-(2-hydroxy-5-nitrophenyl)urea
—— (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-N-(2-methylphenyl)-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H23N3O4S2
(2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-N-(2-methylphenyl)-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— (5Z)-3-(4-bromobenzyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C19H16BrNO5S
(5Z)-3-(4-bromobenzyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— (5Z)-3-cyclohexyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H15Br2NO2S2
(5Z)-3-cyclohexyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C18H12BrClFNO4S
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(2-chloro-4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-3-phenylpropanamide —— C17H18N2O2
N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]-3-phenylpropanamide
—— 6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-nitropyrimidine-2,4-diol —— C12H9N3O6
6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-nitropyrimidine-2,4-diol
—— 3-(3,4-dihydroxyphenyl)-N'-[(Z)-[3-(4-methoxyphenyl)pyrazol-4-ylidene]methyl]propanehydrazide —— C20H20N4O4
3-(3,4-dihydroxyphenyl)-N'-[(Z)-[3-(4-methoxyphenyl)pyrazol-4-ylidene]methyl]propanehydrazide
—— (4E)-1-(3-bromophenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C18H15BrN2O5
(4E)-1-(3-bromophenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 6-ethyl 8-isopropyl 5-amino-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate —— C27H26N2O7S
6-ethyl 8-isopropyl 5-amino-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate
—— 3,4,5-trihydroxy-N'-[(Z)-pyrrol-2-ylidenemethyl]benzohydrazide —— C12H11N3O4
3,4,5-trihydroxy-N'-[(Z)-pyrrol-2-ylidenemethyl]benzohydrazide
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-(3-methylphenyl)-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C25H22N2O3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-(3-methylphenyl)-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— (4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methyl-2-(2,4,6-trichlorophenyl)pyrazol-3-one —— C17H11Cl4N3O2
(4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methyl-2-(2,4,6-trichlorophenyl)pyrazol-3-one
—— ethyl (2Z)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H32N2O8S
ethyl (2Z)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-prop-2-enoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H25BrN2O6S
ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-prop-2-enoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H8BrN3O6S2
(5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C20H20N2O4S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— (4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(3-chlorophenyl)-5-methylpyrazol-3-one —— C17H13Cl2N3O2
(4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(3-chlorophenyl)-5-methylpyrazol-3-one
—— (2Z)-5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H19FN4O5S
(2Z)-5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— (5Z)-2-amino-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C11H9BrN2O3S
(5Z)-2-amino-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— 3,4,5-trihydroxy-N'-[(4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide —— C14H12N2O5
3,4,5-trihydroxy-N'-[(4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide
—— N-(4-ethoxyphenyl)-2-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-(4-ethoxyphenyl)-2-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide