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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
—— N-[(E)-1-(2-chlorophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H13ClN2O4
N-[(E)-1-(2-chlorophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 3,4,5-trihydroxy-N-[(E)-(3-methoxy-4-phenylmethoxyphenyl)methylideneamino]benzamide —— C22H20N2O6
3,4,5-trihydroxy-N-[(E)-(3-methoxy-4-phenylmethoxyphenyl)methylideneamino]benzamide
—— N-(2,5-dimethylphenyl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide —— C20H23N3O4
N-(2,5-dimethylphenyl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide
—— 3,4,5-trihydroxy-N'-[(E)-thiophen-3-ylmethylidene]benzohydrazide —— C12H10N2O4S
3,4,5-trihydroxy-N'-[(E)-thiophen-3-ylmethylidene]benzohydrazide
—— 5-[(E)-[(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C16H16N4O2S
5-[(E)-[(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— 5-[(E)-[(4,6-dichloropyridin-2-yl)hydrazinylidene]methyl]-2-nitrophenol —— C12H8Cl2N4O3
5-[(E)-[(4,6-dichloropyridin-2-yl)hydrazinylidene]methyl]-2-nitrophenol
—— N'-[(1E)-1-(3-chlorophenyl)propylidene]-3,4,5-trihydroxybenzohydrazide —— C16H15ClN2O4
N'-[(1E)-1-(3-chlorophenyl)propylidene]-3,4,5-trihydroxybenzohydrazide
—— 5-[(E)-[benzyl(phenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C21H20N2O2
5-[(E)-[benzyl(phenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— (3E,6E)-3,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]piperazine-2,5-dione —— C20H18N2O6
(3E,6E)-3,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]piperazine-2,5-dione
—— 2-bromo-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide —— C15H13BrN2O3
2-bromo-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide
—— 3,4,5-trihydroxy-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide —— C15H14N2O6
3,4,5-trihydroxy-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide
—— N'-[(E)-(2-chloro-6-fluorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide —— C14H10ClFN2O4
N'-[(E)-(2-chloro-6-fluorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide
—— 3-[(E)-[[4-[(E)-(3-hydroxyphenyl)methylideneamino]-1,2,4-triazol-3-yl]hydrazinylidene]methyl]phenol —— C16H14N6O2
3-[(E)-[[4-[(E)-(3-hydroxyphenyl)methylideneamino]-1,2,4-triazol-3-yl]hydrazinylidene]methyl]phenol
—— 2-(3-Chloroanilino)-N'-(3-hydroxy-4-methoxybenzylidene)acetohydrazide —— C16H16ClN3O3
2-(3-Chloroanilino)-N'-(3-hydroxy-4-methoxybenzylidene)acetohydrazide
—— 4-HO-N'-(2-((4-HO-3-Nitrobenzoyl)hydrazono)ethylidene)-3-nitrobenzohydrazide —— C16H12N6O8
4-HO-N'-(2-((4-HO-3-Nitrobenzoyl)hydrazono)ethylidene)-3-nitrobenzohydrazide
—— 3,4,5-trihydroxy-N-[(E)-(2,3,4-trimethoxyphenyl)methylideneamino]benzamide —— C17H18N2O7
3,4,5-trihydroxy-N-[(E)-(2,3,4-trimethoxyphenyl)methylideneamino]benzamide
—— 3,4,5-trihydroxy-N-[(E)-[(E)-3-phenylprop-2-enylidene]amino]benzamide —— C16H14N2O4
3,4,5-trihydroxy-N-[(E)-[(E)-3-phenylprop-2-enylidene]amino]benzamide
—— 2-cyano-N-[(E)-(3-hydroxyphenyl)methylideneamino]acetamide —— C10H9N3O2
2-cyano-N-[(E)-(3-hydroxyphenyl)methylideneamino]acetamide
—— N'~1~,N'~4~-bis[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]butanedihydrazide —— C20H22N4O6
N'~1~,N'~4~-bis[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]butanedihydrazide
—— (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17NO3S
(2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H19NO4S
(2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H19NO4S
(2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17NO3S
(2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17NO3S
(2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17NO3S
(2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17NO3S
(2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2E,5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one —— C17H18BrNO4S
(2E,5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one
—— 5-[(E)-[(3,5-dichloropyridin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C13H11Cl2N3O2
5-[(E)-[(3,5-dichloropyridin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— (1S,9R,13Z,16R)-16-acetyl-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one —— C22H17N3O6S
(1S,9R,13Z,16R)-16-acetyl-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one
—— N-[(E)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyanilino)acetamide —— C17H18BrN3O4
N-[(E)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyanilino)acetamide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methylbutanamide —— C13H18N2O3
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methylbutanamide
—— N'-[(E)-(3-Hydroxyphenyl)methylidene]methanesulfonohydrazide —— C8H10N2O3S
N'-[(E)-(3-Hydroxyphenyl)methylidene]methanesulfonohydrazide
—— (2E)-2-(2,4,6-tribromo-3-hydroxybenzylidene)hydrazinecarbothioamide —— C8H6Br3N3OS
(2E)-2-(2,4,6-tribromo-3-hydroxybenzylidene)hydrazinecarbothioamide
—— N'-[(E)-{3-[(4-Chloro-3,5-dimethylphenoxy)methyl]-4-methoxyphenyl}methylidene]-3,4,5-trihydroxybenzohydrazide —— C24H23ClN2O6
N'-[(E)-{3-[(4-Chloro-3,5-dimethylphenoxy)methyl]-4-methoxyphenyl}methylidene]-3,4,5-trihydroxybenzohydrazide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-nitrophenyl)acetamide —— C16H15N3O5
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-nitrophenyl)acetamide
—— 2-(4-chloro-2-methylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H17ClN2O4
2-(4-chloro-2-methylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-(3-chloro-2-methylanilino)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H18ClN3O3
2-(3-chloro-2-methylanilino)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 3,4,5-trihydroxy-N'-[(E)-(4-methoxyphenyl)methylidene]benzohydrazide —— C15H14N2O5
3,4,5-trihydroxy-N'-[(E)-(4-methoxyphenyl)methylidene]benzohydrazide
—— 2-{4-[(E)-{2-[3-(3,4-dihydroxyphenyl)propanoyl]hydrazinylidene}methyl]-2-methoxyphenoxy}acetamide —— C19H21N3O6
2-{4-[(E)-{2-[3-(3,4-dihydroxyphenyl)propanoyl]hydrazinylidene}methyl]-2-methoxyphenoxy}acetamide
—— 3,4,5-trihydroxy-N-[(E)-(3-hydroxy-2,2-dimethylpropylidene)amino]benzamide —— C12H16N2O5
3,4,5-trihydroxy-N-[(E)-(3-hydroxy-2,2-dimethylpropylidene)amino]benzamide
—— 2-hydroxy-N-[(E)-(4-methoxyphenyl)methylideneamino]-5-nitrobenzamide —— C15H13N3O5
2-hydroxy-N-[(E)-(4-methoxyphenyl)methylideneamino]-5-nitrobenzamide
—— N-[(E)-(2-chlorophenyl)methylideneamino]-2-hydroxy-3,5-dinitrobenzamide —— C14H9ClN4O6
N-[(E)-(2-chlorophenyl)methylideneamino]-2-hydroxy-3,5-dinitrobenzamide
—— 3,4,5-trihydroxy-N-[(E)-3-methylbutan-2-ylideneamino]benzamide —— C12H16N2O4
3,4,5-trihydroxy-N-[(E)-3-methylbutan-2-ylideneamino]benzamide
—— 3-bromo-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide —— C15H13BrN2O3
3-bromo-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]benzohydrazide
—— N-[(E)-(3-fluorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H11FN2O4
N-[(E)-(3-fluorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— N'1,N'4-bis(3-hydroxybenzylidene)succinohydrazide —— C18H18N4O4
N'1,N'4-bis(3-hydroxybenzylidene)succinohydrazide
—— N-[(E)-1-(4-bromophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H13BrN2O4
N-[(E)-1-(4-bromophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 4-[2-[1-[(1S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]piperidin-4-yl]ethyl]phenol —— C23H27N3O2
4-[2-[1-[(1S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]piperidin-4-yl]ethyl]phenol
—— 4-[2-[1-[(1R)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]piperidin-4-yl]ethyl]phenol —— C23H27N3O2
4-[2-[1-[(1R)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]piperidin-4-yl]ethyl]phenol
—— 2-[(3-Hydroxy-4-methoxybenzylidene)hydrazino]-4-morpholino-6-(1-pyrrolidinyl)-1,3,5-triazine —— C19H25N7O3
2-[(3-Hydroxy-4-methoxybenzylidene)hydrazino]-4-morpholino-6-(1-pyrrolidinyl)-1,3,5-triazine