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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
—— 2-Methoxy-5-{[(4-methyl-1-piperazinyl)imino]methyl}phenol —— C13H19N3O2
2-Methoxy-5-{[(4-methyl-1-piperazinyl)imino]methyl}phenol
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H17NO4S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-N'-[(Z)-(3-hydroxyphenyl)methylideneamino]hexanediamide —— C20H22N4O4
N-[(E)-(3-hydroxyphenyl)methylideneamino]-N'-[(Z)-(3-hydroxyphenyl)methylideneamino]hexanediamide
—— (3E)-3-[(E)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]-1-prop-2-enylindol-2-one —— C19H17N3O3
(3E)-3-[(E)-(3-hydroxy-4-methoxyphenyl)methylidenehydrazinylidene]-1-prop-2-enylindol-2-one
—— 5-[(E)-[3-[(4-chlorophenyl)methylsulfanyl]-5-propyl-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol —— C20H21ClN4O2S
5-[(E)-[3-[(4-chlorophenyl)methylsulfanyl]-5-propyl-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol
—— 5-[(E)-[3-[(4-bromophenyl)methylsulfanyl]-5-methyl-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol —— C18H17BrN4O2S
5-[(E)-[3-[(4-bromophenyl)methylsulfanyl]-5-methyl-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol
—— 3-[(E)-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-[[cyclohexyl(methyl)amino]methyl]triazole-4-carbonyl]hydrazinylidene]methyl]phenolate —— C20H25N9O3
3-[(E)-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-[[cyclohexyl(methyl)amino]methyl]triazole-4-carbonyl]hydrazinylidene]methyl]phenolate
—— 1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-[[3-(pyrazol-1-ylmethyl)phenyl]methyl]urea —— C22H26N4O2
1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-[[3-(pyrazol-1-ylmethyl)phenyl]methyl]urea
—— 2-(3,5-dimethyl-1H-pyrazol-1-yl)-N'-[(E)-(3-hydroxyphenyl)methylidene]acetohydrazide —— C14H16N4O2
2-(3,5-dimethyl-1H-pyrazol-1-yl)-N'-[(E)-(3-hydroxyphenyl)methylidene]acetohydrazide
—— N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]pyridine-4-carbohydrazide —— C13H10N4O4
N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]pyridine-4-carbohydrazide
—— (3R)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide —— C17H16N2O5
(3R)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
—— 2-[[4-[(3S)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methyl]-4-ethoxy-6-prop-2-enylphenol —— C20H30N2O4S
2-[[4-[(3S)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methyl]-4-ethoxy-6-prop-2-enylphenol
—— ethyl (2E,5R)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O5S
ethyl (2E,5R)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]pyridine-2-carbohydrazide —— C13H10N4O4
N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]pyridine-2-carbohydrazide
—— N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(2-thienyl)acetohydrazide —— C13H12N2O2S
N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(2-thienyl)acetohydrazide
—— N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(1H-1,2,4-triazol-1-yl)acetohydrazide —— C11H11N5O2
N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(1H-1,2,4-triazol-1-yl)acetohydrazide
—— 2-(5-amino-2H-tetrazol-2-yl)-N'-[(E)-(3-hydroxyphenyl)methylidene]acetohydrazide —— C10H11N7O2
2-(5-amino-2H-tetrazol-2-yl)-N'-[(E)-(3-hydroxyphenyl)methylidene]acetohydrazide
—— tert-butyl (2E)-2-(2,4,6-tribromo-3-hydroxybenzylidene)hydrazinecarboxylate —— C12H13Br3N2O3
tert-butyl (2E)-2-(2,4,6-tribromo-3-hydroxybenzylidene)hydrazinecarboxylate
—— N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide —— C16H13N3O6
N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide
—— N'-[(E)-(3-hydroxy-5-nitrophenyl)methylidene]-1,3,7-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbohydrazide —— C18H16N6O6
N'-[(E)-(3-hydroxy-5-nitrophenyl)methylidene]-1,3,7-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbohydrazide
—— 3-{[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-8-methyl-3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one —— C19H16N4O3
3-{[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-8-methyl-3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one
—— 2-{[3-cyano-4-(methoxymethyl)-6-methylpyridin-2-yl]oxy}-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide —— C19H20N4O5
2-{[3-cyano-4-(methoxymethyl)-6-methylpyridin-2-yl]oxy}-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1S,3R)-3-methylcyclohexyl]methyl]urea —— C18H28N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1S,3R)-3-methylcyclohexyl]methyl]urea
—— 1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1R,3S)-3-methylcyclohexyl]methyl]urea —— C18H28N2O3
1-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-3-[[(1R,3S)-3-methylcyclohexyl]methyl]urea
—— N'-(3-Hydroxybenzylidene)-2-(1-methyl-1H-pyrrol-2-YL)acetohydrazide —— C14H15N3O2
N'-(3-Hydroxybenzylidene)-2-(1-methyl-1H-pyrrol-2-YL)acetohydrazide
—— [(Z)-[3-[(E)-(carbamothioylhydrazinylidene)methyl]-5-hydroxy-4-methoxyphenyl]methylideneamino]thiourea —— C11H14N6O2S2
[(Z)-[3-[(E)-(carbamothioylhydrazinylidene)methyl]-5-hydroxy-4-methoxyphenyl]methylideneamino]thiourea
—— (5E)-3-[(3S)-1,1-dioxothiolan-3-yl]-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H13NO4S3
(5E)-3-[(3S)-1,1-dioxothiolan-3-yl]-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H9NO4S2
(5E)-5-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-{[(3-ethyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)imino]methyl}phenol —— C11H12N4OS
3-{[(3-ethyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)imino]methyl}phenol
—— 2-chloro-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide —— C15H13ClN2O3
2-chloro-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide
—— N'-(3-hydroxy-4-methoxybenzylidene)-5-({4-nitro-1H-pyrazol-1-yl}methyl)-2-furohydrazide —— C17H15N5O6
N'-(3-hydroxy-4-methoxybenzylidene)-5-({4-nitro-1H-pyrazol-1-yl}methyl)-2-furohydrazide
—— N'-[(E)-(2,3-dichlorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide —— C14H10Cl2N2O4
N'-[(E)-(2,3-dichlorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide
—— 3-{(2E)-2-[(2E)-benzylidenehydrazinylidene]-3-methyl-2,3-dihydro-1,3-thiazol-4-yl}phenol —— C17H15N3OS
3-{(2E)-2-[(2E)-benzylidenehydrazinylidene]-3-methyl-2,3-dihydro-1,3-thiazol-4-yl}phenol
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylfuran-3-carboxamide —— C14H14N2O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methylfuran-3-carboxamide
—— 4-chloro-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide —— C15H13ClN2O3
4-chloro-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide
—— 2-methoxy-5-[(E)-[3-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-4-yl]iminomethyl]phenol —— C18H18N4O2S
2-methoxy-5-[(E)-[3-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-4-yl]iminomethyl]phenol
—— 5-[(E)-[3-[(2-chlorophenyl)methylsulfanyl]-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol —— C17H15ClN4O2S
5-[(E)-[3-[(2-chlorophenyl)methylsulfanyl]-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol
—— 3-chloro-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide —— C15H13ClN2O3
3-chloro-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide
—— 2-(2,4-Dimethylphenoxy)-N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]acetohydrazide —— C17H17N3O5
2-(2,4-Dimethylphenoxy)-N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]acetohydrazide
—— 2,4-dichloro-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide —— C15H12Cl2N2O3
2,4-dichloro-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide
—— 3-{(E)-[2-({1-(4-amino-1,2,5-oxadiazol-3-yl)-5-[(dimethylammonio)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)hydrazinylidene]methyl}phenolate —— C15H17N9O3
3-{(E)-[2-({1-(4-amino-1,2,5-oxadiazol-3-yl)-5-[(dimethylammonio)methyl]-1H-1,2,3-triazol-4-yl}carbonyl)hydrazinylidene]methyl}phenolate
—— N'-(3-hydroxy-4-methoxybenzylidene)-2-nitrobenzohydrazide —— C15H13N3O5
N'-(3-hydroxy-4-methoxybenzylidene)-2-nitrobenzohydrazide
—— 5-bromo-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]pyridine-3-carbohydrazide —— C14H12BrN3O3
5-bromo-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]pyridine-3-carbohydrazide
—— N'-(3-hydroxy-4-methoxybenzylidene)-3-nitrobenzohydrazide —— C15H13N3O5
N'-(3-hydroxy-4-methoxybenzylidene)-3-nitrobenzohydrazide
—— 3-{[(E)-3-Mercapto-5-(5-methyl-2H-pyrazol-3-yl)-[1,2,4]triazol-4-ylimino]-methyl}-phenol —— C13H12N6OS
3-{[(E)-3-Mercapto-5-(5-methyl-2H-pyrazol-3-yl)-[1,2,4]triazol-4-ylimino]-methyl}-phenol
—— 3-[(E)-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]hydrazinylidene]methyl]phenolate —— C15H16N8O3
3-[(E)-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]hydrazinylidene]methyl]phenolate
—— (2S)-N-[(E)-(4-fluorophenyl)methylideneamino]-2-(2-hydroxy-5-nitroanilino)-2-phenylacetamide —— C21H17FN4O4
(2S)-N-[(E)-(4-fluorophenyl)methylideneamino]-2-(2-hydroxy-5-nitroanilino)-2-phenylacetamide
—— 4-{[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-6-methyl-3-sulfanyl-1,2,4-triazin-5(4H)-one —— C12H12N4O3S
4-{[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]amino}-6-methyl-3-sulfanyl-1,2,4-triazin-5(4H)-one
—— 3-[(E)-(2-{[1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(morpholin-4-ium-4-ylmethyl)-1H-1,2,3-triazol-4-yl]carbonyl}hydrazinylidene)methyl]phenolate —— C17H19N9O4
3-[(E)-(2-{[1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(morpholin-4-ium-4-ylmethyl)-1H-1,2,3-triazol-4-yl]carbonyl}hydrazinylidene)methyl]phenolate
—— 3-(3,5-dioxo-2H-1,2,4-triazin-6-yl)-N-[(E)-(3-hydroxyphenyl)methylideneamino]propanamide —— C13H13N5O4
3-(3,5-dioxo-2H-1,2,4-triazin-6-yl)-N-[(E)-(3-hydroxyphenyl)methylideneamino]propanamide