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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
—— 6-tert-butyl-8-[(Z)-(3-hydroxyphenyl)methylideneamino]-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one —— C15H16N6O2
6-tert-butyl-8-[(Z)-(3-hydroxyphenyl)methylideneamino]-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one
—— (E)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[1-(4-methylphenyl)sulfonylindol-3-yl]prop-2-enamide —— C25H18N4O6S
(E)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[1-(4-methylphenyl)sulfonylindol-3-yl]prop-2-enamide
—— 5-(2-hydroxy-5-nitrobenzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione 202063-68-1 C11H7N3O5S
5-(2-hydroxy-5-nitrobenzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27BrN2O6S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3,4,5-trihydroxy-N-[(Z)-1-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]ethylideneamino]benzamide —— C17H14F3N3O5
3,4,5-trihydroxy-N-[(Z)-1-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]ethylideneamino]benzamide
—— N'-[(E)-(3-bromo-5-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxy-5-nitrobenzohydrazide —— C16H14BrN3O6
N'-[(E)-(3-bromo-5-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxy-5-nitrobenzohydrazide
—— ethyl (2Z)-5-(3,4-diethoxyphenyl)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl (2Z)-5-(3,4-diethoxyphenyl)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H16N4O2
5-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— (5E)-5-[(3-bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C27H25BrN2O3S
(5E)-5-[(3-bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(E)-1-(3-Bromo-4-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolan-4-one —— C19H17BrN2O3S
5-[(E)-1-(3-Bromo-4-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolan-4-one
—— (6Z)-6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one —— C17H15N3O3
(6Z)-6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one
—— 5-[(Z)-(5-aminotetrazol-1-yl)iminomethyl]-3-bromo-2-methoxyphenol —— C9H9BrN6O2
5-[(Z)-(5-aminotetrazol-1-yl)iminomethyl]-3-bromo-2-methoxyphenol
—— (4Z)-1-(4-bromophenyl)-4-[(4-hydroxy-3-nitrophenyl)methylidene]pyrazolidine-3,5-dione —— C16H10BrN3O5
(4Z)-1-(4-bromophenyl)-4-[(4-hydroxy-3-nitrophenyl)methylidene]pyrazolidine-3,5-dione
—— Methyl 2-[(2-hydroxy-5-nitrophenyl)methylene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-A]pyrimidine-6(3H)-carboxylate —— C22H17N3O6S
Methyl 2-[(2-hydroxy-5-nitrophenyl)methylene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-A]pyrimidine-6(3H)-carboxylate
—— (4Z)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-(4-bromophenyl)pyrazolidine-3,5-dione —— C16H10Br2N2O3
(4Z)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-(4-bromophenyl)pyrazolidine-3,5-dione
—— (6E)-6-[(2-hydroxy-3-methylanilino)methylidene]-2,4-dinitrocyclohexa-2,4-dien-1-one —— C14H11N3O6
(6E)-6-[(2-hydroxy-3-methylanilino)methylidene]-2,4-dinitrocyclohexa-2,4-dien-1-one
—— (5E)-1-benzyl-5-[(5-chloro-2-hydroxyanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C21H16ClN3O3
(5E)-1-benzyl-5-[(5-chloro-2-hydroxyanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— (2E)-3-(2-hydroxy-3-methyl-5-nitrophenyl)acrylaldehyde —— C10H9NO4
(2E)-3-(2-hydroxy-3-methyl-5-nitrophenyl)acrylaldehyde
—— (2E)-3-(2-hydroxy-3-methyl-5-nitrophenyl)-2-methylacrylaldehyde —— C11H11NO4
(2E)-3-(2-hydroxy-3-methyl-5-nitrophenyl)-2-methylacrylaldehyde
—— (2E)-3-(2,3-dibromo-6-hydroxy-5-methoxyphenyl)acrylaldehyde —— C10H8Br2O3
(2E)-3-(2,3-dibromo-6-hydroxy-5-methoxyphenyl)acrylaldehyde
—— (4E)-4-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C16H10Br2N2O3
(4E)-4-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— (3Z)-2-amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)but-3-ene-1,1,3-tricarbonitrile —— C14H11BrN4O2
(3Z)-2-amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)but-3-ene-1,1,3-tricarbonitrile
—— 4-Amino-2-chloro-6-ethylphenol —— C8H10ClNO
4-Amino-2-chloro-6-ethylphenol
—— 4-Amino-2-bromo-6-ethylphenol —— C8H10BrNO
4-Amino-2-bromo-6-ethylphenol
—— ethyl (2Z)-2-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-5-(2-methoxynaphthalen-1-yl)-3-oxo-7-propyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H26N4O9S
ethyl (2Z)-2-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-5-(2-methoxynaphthalen-1-yl)-3-oxo-7-propyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(3,4-dihydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C16H12N2O3S
(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— 2-Hydroxymethyl-6-methyl-4-nitro-phenol —— C8H9NO4
2-Hydroxymethyl-6-methyl-4-nitro-phenol
—— 2-Amino-4-isopropyl-6-nitrophenol —— C9H12N2O3
2-Amino-4-isopropyl-6-nitrophenol
—— 3-Bromo-5-ethoxy-2-hydroxybenzaldehyde —— C9H9BrO3
3-Bromo-5-ethoxy-2-hydroxybenzaldehyde
—— 4-Amino-2-(hydroxymethyl)-6-methylphenol —— C8H11NO2
4-Amino-2-(hydroxymethyl)-6-methylphenol
—— 3-Chloro-5-ethoxy-2-hydroxybenzaldehyde —— C9H9ClO3
3-Chloro-5-ethoxy-2-hydroxybenzaldehyde
—— (5Z)-3-(2-chloro-4-fluorobenzyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C19H15ClFNO5S
(5Z)-3-(2-chloro-4-fluorobenzyl)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— ethyl 2-(4-hydroxy-3-methoxybenzylidene)-5-(4-isopropoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl 2-(4-hydroxy-3-methoxybenzylidene)-5-(4-isopropoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C10H7N5O5S
5-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-cyclohexyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H18BrNO3S2
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-cyclohexyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-methoxy-5-[(Z)-(7H-purin-6-ylhydrazinylidene)methyl]phenol —— C13H12N6O2
2-methoxy-5-[(Z)-(7H-purin-6-ylhydrazinylidene)methyl]phenol
—— 4-[(E,3S)-3-hydroxy-4,4-dimethylpent-1-enyl]-2-methoxyphenol —— C14H20O3
4-[(E,3S)-3-hydroxy-4,4-dimethylpent-1-enyl]-2-methoxyphenol
—— 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;dihydrochloride —— C18H28Cl2N2O6
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;4-[(1S)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;dihydrochloride
—— 4-[(E,3R)-3-hydroxy-4,4-dimethylpent-1-enyl]-2-methoxyphenol —— C14H20O3
4-[(E,3R)-3-hydroxy-4,4-dimethylpent-1-enyl]-2-methoxyphenol
—— disodium;(1Z)-1-[(5-chloro-2-hydroxyphenyl)hydrazinylidene]naphthalen-2-one;chromium;(4Z)-4-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-7-(4-methoxyanilino)-3-oxonaphthalene-2-sulfonic acid —— C39H28ClCrN7Na2O12S+2
disodium;(1Z)-1-[(5-chloro-2-hydroxyphenyl)hydrazinylidene]naphthalen-2-one;chromium;(4Z)-4-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-7-(4-methoxyanilino)-3-oxonaphthalene-2-sulfonic acid
—— (2Z,5E)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-2-[(4-fluorophenyl)imino]-1,3-thiazolidin-4-one —— C16H9BrClFN2O2S
(2Z,5E)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-2-[(4-fluorophenyl)imino]-1,3-thiazolidin-4-one
—— (2E,5E)-5-(3-chloro-4-hydroxybenzylidene)-2-[(4-methylphenyl)imino]-1,3-thiazolidin-4-one —— C17H13ClN2O2S
(2E,5E)-5-(3-chloro-4-hydroxybenzylidene)-2-[(4-methylphenyl)imino]-1,3-thiazolidin-4-one
—— (E)-2-cyano-3-[5-(3,4-dichlorophenyl)furan-2-yl]-N-(2-hydroxy-4-nitrophenyl)prop-2-enamide —— C20H11Cl2N3O5
(E)-2-cyano-3-[5-(3,4-dichlorophenyl)furan-2-yl]-N-(2-hydroxy-4-nitrophenyl)prop-2-enamide
—— 4-[3-[[(1S,4R)-4-(hydroxymethyl)cyclopent-2-en-1-yl]amino]butyl]phenol —— C16H23NO2
4-[3-[[(1S,4R)-4-(hydroxymethyl)cyclopent-2-en-1-yl]amino]butyl]phenol
—— 4-[3-[(2,5-Dimethylpyrazol-3-yl)amino]butyl]phenol —— C15H21N3O
4-[3-[(2,5-Dimethylpyrazol-3-yl)amino]butyl]phenol
—— 3-(4-Hydroxyphenyl)-1-[2-methyl-2-(1-methylpyrazol-4-yl)morpholin-4-yl]propan-1-one —— C18H23N3O3
3-(4-Hydroxyphenyl)-1-[2-methyl-2-(1-methylpyrazol-4-yl)morpholin-4-yl]propan-1-one
—— 2-methoxy-5-[(E)-2-[4-(4-methylphenyl)-1,3-thiazol-2-yl]ethenyl]phenol —— C19H17NO2S
2-methoxy-5-[(E)-2-[4-(4-methylphenyl)-1,3-thiazol-2-yl]ethenyl]phenol
—— Potassium trifluoro(5-fluoro-2-hydroxyphenyl)borate —— C6H4BF4O*K
Potassium trifluoro(5-fluoro-2-hydroxyphenyl)borate
—— (5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C10H6ClNO3S2
(5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C16H17NO5S2
5-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid