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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
—— 4-[(E)-[(3-Chloro-6-hydroxy-2,4-dimethyl-5-nitrophenyl)methylidene]amino]benzoic acid —— C16H13ClN2O5
4-[(E)-[(3-Chloro-6-hydroxy-2,4-dimethyl-5-nitrophenyl)methylidene]amino]benzoic acid
—— ethyl 2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl 2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R,4S)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(morpholine-4-carbonyl)-2,4-diphenylcyclobutane-1-carboxamide —— C29H29N3O4
(2R,4S)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(morpholine-4-carbonyl)-2,4-diphenylcyclobutane-1-carboxamide
—— Diethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(4-methoxybenzyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C26H28BrNO7
Diethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(4-methoxybenzyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— N-[(E)-1-(4-ethylphenyl)ethylideneamino]-2-hydroxy-3,5-dinitrobenzamide —— C17H16N4O6
N-[(E)-1-(4-ethylphenyl)ethylideneamino]-2-hydroxy-3,5-dinitrobenzamide
—— 2-methoxy-5-[(Z)-[[4-morpholin-4-yl-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]phenol —— C21H22N8O5
2-methoxy-5-[(Z)-[[4-morpholin-4-yl-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]phenol
—— (2R,4R)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(morpholine-4-carbonyl)-2,4-diphenylcyclobutane-1-carboxamide —— C29H29N3O4
(2R,4R)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(morpholine-4-carbonyl)-2,4-diphenylcyclobutane-1-carboxamide
—— (2S,4S)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(morpholine-4-carbonyl)-2,4-diphenylcyclobutane-1-carboxamide —— C29H29N3O4
(2S,4S)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-(morpholine-4-carbonyl)-2,4-diphenylcyclobutane-1-carboxamide
—— (4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(4-chlorophenyl)-5-methylpyrazol-3-one —— C17H13Cl2N3O2
(4Z)-4-[(5-chloro-2-hydroxyanilino)methylidene]-2-(4-chlorophenyl)-5-methylpyrazol-3-one
—— 4-[1-({1-ethyl-4-nitro-1H-pyrazol-3-yl}carbonyl)-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2-methoxyphenol —— C22H21N5O6
4-[1-({1-ethyl-4-nitro-1H-pyrazol-3-yl}carbonyl)-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2-methoxyphenol
—— 4-hydroxy-2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-5-nitro-1H-pyrimidin-6-one —— C14H13N3O7
4-hydroxy-2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-5-nitro-1H-pyrimidin-6-one
—— Dimethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(4-chlorobenzyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C23H21BrClNO6
Dimethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(4-chlorobenzyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— 8a-bromo-7-ethenyl-8-(3-fluoro-4-hydroxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H16BrFO3
8a-bromo-7-ethenyl-8-(3-fluoro-4-hydroxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(5-Bromo-2,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C10H6BrNO3S2
5-[(5-Bromo-2,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2S)-5-(2-hydroxy-5-nitroanilino)-5-oxo-2-propylpentanoic acid —— C14H18N2O6
(2S)-5-(2-hydroxy-5-nitroanilino)-5-oxo-2-propylpentanoic acid
—— ethyl 5-(3,4-diethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl 5-(3,4-diethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-5-(2-hydroxy-5-nitroanilino)-5-oxo-2-propylpentanoic acid —— C14H18N2O6
(2R)-5-(2-hydroxy-5-nitroanilino)-5-oxo-2-propylpentanoic acid
—— 5-[(2,4-Dihydroxyphenyl)methylidene]-3-[(4-methoxyphenyl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO4S2
5-[(2,4-Dihydroxyphenyl)methylidene]-3-[(4-methoxyphenyl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[5-(5-chloro-2-hydroxyphenyl)-2,3-dihydro-1H-pyrazol-3-yl]-2-methoxyphenol —— C16H15ClN2O3
4-[5-(5-chloro-2-hydroxyphenyl)-2,3-dihydro-1H-pyrazol-3-yl]-2-methoxyphenol
—— 1-[7-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethanone —— C15H15BrN4O3
1-[7-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethanone
—— 5-[[(4,6-Dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H16N4O2
5-[[(4,6-Dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— 2-{(E)-[(4-bromo-3-methylphenyl)imino]methyl}-6-methoxyphenol —— C15H14BrNO2
2-{(E)-[(4-bromo-3-methylphenyl)imino]methyl}-6-methoxyphenol
—— 3-Cyclohexyl-5-[(2-hydroxyphenyl)methylidene]-2-prop-2-enylimino-1,3-thiazolidin-4-one —— C19H22N2O2S
3-Cyclohexyl-5-[(2-hydroxyphenyl)methylidene]-2-prop-2-enylimino-1,3-thiazolidin-4-one
—— 2-[(4-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
2-[(4-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
—— 5-[(3-Bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C27H25BrN2O3S
5-[(3-Bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 2-(2,3-dichlorophenoxy)-N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]acetamide —— C16H14Cl2N2O4
2-(2,3-dichlorophenoxy)-N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]acetamide
—— 2-[Benzotriazol-1-yl(hydroxy)methyl]-6-methoxyphenol —— C14H13N3O3
2-[Benzotriazol-1-yl(hydroxy)methyl]-6-methoxyphenol
—— 1-Hydroxy-2-(3-hydroxyphenyl)-1,2,3,4-tetrahydro-1,2,4-benzotriazin-3-one —— C13H11N3O3
1-Hydroxy-2-(3-hydroxyphenyl)-1,2,3,4-tetrahydro-1,2,4-benzotriazin-3-one
—— N-Cyclohexyl-Na(2)-[2-(3,4-dihydroxyphenyl)ethyl]urea 710292-27-6 C15H22N2O3
N-Cyclohexyl-Na(2)-[2-(3,4-dihydroxyphenyl)ethyl]urea
—— 3-[(3,4-Dichlorophenyl)methyl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H13Cl2NO4S
3-[(3,4-Dichlorophenyl)methyl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— N-(2-hydroxy-5-nitrophenyl)-N'-(2-methyl-5-nitrophenyl)urea —— C14H12N4O6
N-(2-hydroxy-5-nitrophenyl)-N'-(2-methyl-5-nitrophenyl)urea
—— [Amino-(3-hydroxy-4-methoxyphenyl)methylidene]-hydroxyazanium —— C8H11N2O3+
[Amino-(3-hydroxy-4-methoxyphenyl)methylidene]-hydroxyazanium
—— N-[4-acetyl-5-(5-chloro-2-hydroxyphenyl)-5-methyl-1,3,4-thiadiazol-2-yl]acetamide —— C13H14ClN3O3S
N-[4-acetyl-5-(5-chloro-2-hydroxyphenyl)-5-methyl-1,3,4-thiadiazol-2-yl]acetamide
—— 6-Amino-5,7-dicyano-8-(3-hydroxyphenyl)-2-methyl-2,3,8,8A-tetrahydro-7(1H)-isoquinolinyl cyanide —— C19H17N5O
6-Amino-5,7-dicyano-8-(3-hydroxyphenyl)-2-methyl-2,3,8,8A-tetrahydro-7(1H)-isoquinolinyl cyanide
—— 6-amino-8-(3-hydroxyphenyl)-2-methyl-2,3,8,8a-tetrahydro-1H-isoquinolin-2-ium-5,7,7-tricarbonitrile —— C19H18N5O+
6-amino-8-(3-hydroxyphenyl)-2-methyl-2,3,8,8a-tetrahydro-1H-isoquinolin-2-ium-5,7,7-tricarbonitrile
—— 2-(4-chlorophenoxy)-N'-[1-(2,5-dihydroxyphenyl)ethenyl]acetohydrazide —— C16H15ClN2O4
2-(4-chlorophenoxy)-N'-[1-(2,5-dihydroxyphenyl)ethenyl]acetohydrazide
—— 2-(2-cyanophenoxy)-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C16H12N4O5
2-(2-cyanophenoxy)-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— 5-[(3-Bromo-4-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C19H17BrN2O3S
5-[(3-Bromo-4-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— N'-[1-(2,5-dihydroxyphenyl)ethenyl]-2-(2,6-dimethylphenoxy)acetohydrazide —— C18H20N2O4
N'-[1-(2,5-dihydroxyphenyl)ethenyl]-2-(2,6-dimethylphenoxy)acetohydrazide
—— 6-Bromo-2-(4-hydroxy-3,5-dimethylphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C23H20BrN3O5
6-Bromo-2-(4-hydroxy-3,5-dimethylphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— 7-ethenyl-8-(4-hydroxy-2,6-dimethoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O5
7-ethenyl-8-(4-hydroxy-2,6-dimethoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3-(2-hydroxyphenyl)-5-(1,1,2,2-tetrafluoroethyl)-2H-1,2-oxazol-5-ol —— C11H9F4NO3
3-(2-hydroxyphenyl)-5-(1,1,2,2-tetrafluoroethyl)-2H-1,2-oxazol-5-ol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one —— C14H15BrN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one
—— 5-(2-Hydroxyphenyl)-3-(trifluoromethyl)-1,2-dihydropyrazol-3-ol —— C10H9F3N2O2
5-(2-Hydroxyphenyl)-3-(trifluoromethyl)-1,2-dihydropyrazol-3-ol
—— 2-(4-Bromophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H11BrN2O3S
2-(4-Bromophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[2-(4-Fluorophenyl)-6-(3-methoxyphenyl)-2,3,4,5-tetrahydropyrimidin-4-yl]-5-methoxyphenol —— C24H23FN2O3
2-[2-(4-Fluorophenyl)-6-(3-methoxyphenyl)-2,3,4,5-tetrahydropyrimidin-4-yl]-5-methoxyphenol
—— N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]-2-(tetrazol-1-yl)acetamide —— C13H14N6O2
N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]-2-(tetrazol-1-yl)acetamide
—— 5-[(5-Aminotetrazol-1-yl)iminomethyl]-3-bromo-2-methoxyphenol —— C9H9BrN6O2
5-[(5-Aminotetrazol-1-yl)iminomethyl]-3-bromo-2-methoxyphenol
—— 2-Phenylethyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C21H22N2O5
2-Phenylethyl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 3-(3,4-Dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C26H23N3O4S
3-(3,4-Dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one