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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
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N'-(3-hydroxybenzylidene)-5-(1-pyrrolidinylmethyl)-1H-1,2,3-triazole-4-carbohydrazide —— C17H19N9O3
1-(4-amino-1,2,5-oxadiazol-3-yl)-N'-(3-hydroxybenzylidene)-5-(1-pyrrolidinylmethyl)-1H-1,2,3-triazole-4-carbohydrazide
—— N'-[(E)-(3-Hydroxy-4-nitrophenyl)methylidene]-6-methylpyridine-3-carbohydrazide —— C14H12N4O4
N'-[(E)-(3-Hydroxy-4-nitrophenyl)methylidene]-6-methylpyridine-3-carbohydrazide
—— 3,4,5-trihydroxy-N-[(E)-(4-propoxyphenyl)methylideneamino]benzamide —— C17H18N2O5
3,4,5-trihydroxy-N-[(E)-(4-propoxyphenyl)methylideneamino]benzamide
—— 2-hydroxy-5-nitro-N'-[(E)-thiophen-2-ylmethylidene]benzohydrazide —— C12H9N3O4S
2-hydroxy-5-nitro-N'-[(E)-thiophen-2-ylmethylidene]benzohydrazide
—— 3,4,5-trihydroxy-N-[(E)-1-(4-methylphenyl)ethylideneamino]benzamide —— C16H16N2O4
3,4,5-trihydroxy-N-[(E)-1-(4-methylphenyl)ethylideneamino]benzamide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-(2-methylpropoxy)benzamide —— C19H22N2O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-(2-methylpropoxy)benzamide
—— 2-(2-bromo-4-chlorophenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H14BrClN2O4
2-(2-bromo-4-chlorophenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-(2-bromo-4-tert-butylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C20H23BrN2O4
2-(2-bromo-4-tert-butylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-prop-2-enoxybenzamide —— C18H18N2O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-prop-2-enoxybenzamide
—— 3-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5,6-dimethylthieno[2,3-d]pyrimidin-4-one —— C16H15N3O3S
3-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5,6-dimethylthieno[2,3-d]pyrimidin-4-one
—— 3,4,5-trihydroxy-N-[(E)-(2-methoxyphenyl)methylideneamino]benzamide —— C15H14N2O5
3,4,5-trihydroxy-N-[(E)-(2-methoxyphenyl)methylideneamino]benzamide
—— 3,4,5-trihydroxy-N'-[(E)-(3-hydroxyphenyl)methylidene]benzohydrazide —— C14H12N2O5
3,4,5-trihydroxy-N'-[(E)-(3-hydroxyphenyl)methylidene]benzohydrazide
—— 3,4,5-trihydroxy-N-[(E)-[4-methoxy-3-[(3-nitro-1,2,4-triazol-1-yl)methyl]phenyl]methylideneamino]benzamide —— C18H16N6O7
3,4,5-trihydroxy-N-[(E)-[4-methoxy-3-[(3-nitro-1,2,4-triazol-1-yl)methyl]phenyl]methylideneamino]benzamide
—— 3,4,5-trihydroxy-N'-[(E)-(4-methylphenyl)methylidene]benzohydrazide —— C15H14N2O4
3,4,5-trihydroxy-N'-[(E)-(4-methylphenyl)methylidene]benzohydrazide
—— Methyl cyano({2-hydroxy-4-nitrophenyl}hydrazono)acetate —— C10H8N4O5
Methyl cyano({2-hydroxy-4-nitrophenyl}hydrazono)acetate
—— 5-[(E)-[(2,4-difluorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H12F2N2O2
5-[(E)-[(2,4-difluorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 2-Bromo-N'-(3-bromo-5-hydroxy-4-methoxybenzylidene)benzohydrazide —— C15H12Br2N2O3
2-Bromo-N'-(3-bromo-5-hydroxy-4-methoxybenzylidene)benzohydrazide
—— 3,4,5-trihydroxy-N-[(E)-(5-methylthiophen-2-yl)methylideneamino]benzamide —— C13H12N2O4S
3,4,5-trihydroxy-N-[(E)-(5-methylthiophen-2-yl)methylideneamino]benzamide
—— 3-bromo-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methoxybenzamide —— C16H15BrN2O4
3-bromo-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methoxybenzamide
—— 2-(2-bromo-4-ethylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H19BrN2O4
2-(2-bromo-4-ethylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methoxybenzamide —— C16H16N2O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methoxybenzamide
—— N-[(E)-(4-ethoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C16H16N2O5
N-[(E)-(4-ethoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— N-[(E)-1-(4-aminophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H15N3O4
N-[(E)-1-(4-aminophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— N-[(E)-(2-ethoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C16H16N2O5
N-[(E)-(2-ethoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 3-chloro-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-methyl-1-benzothiophene-2-carboxamide —— C18H15ClN2O3S
3-chloro-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-methyl-1-benzothiophene-2-carboxamide
—— 3-Bromo-5-hydroxy-4-methoxybenzaldehyde phenylhydrazone 302910-28-7 C14H13BrN2O2
3-Bromo-5-hydroxy-4-methoxybenzaldehyde phenylhydrazone
—— 4-[(2E)-2-(3-bromo-5-hydroxy-4-methoxybenzylidene)hydrazino]-N-(4-bromophenyl)-4-oxobutanamide —— C18H17Br2N3O4
4-[(2E)-2-(3-bromo-5-hydroxy-4-methoxybenzylidene)hydrazino]-N-(4-bromophenyl)-4-oxobutanamide
—— 1-[(3-Hydroxy-4-methoxy-benzylidene)amino]-3-(2-nitrophenyl)thiourea —— C15H14N4O4S
1-[(3-Hydroxy-4-methoxy-benzylidene)amino]-3-(2-nitrophenyl)thiourea
—— 2-(2,4-dimethylphenoxy)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide —— C18H20N2O4
2-(2,4-dimethylphenoxy)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide
—— 2-(2,4-dibromo-6-methylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H16Br2N2O4
2-(2,4-dibromo-6-methylphenoxy)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2-[(3-methylphenyl)amino]acetohydrazide (non-preferred name) —— C16H16N4O4
N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-2-[(3-methylphenyl)amino]acetohydrazide (non-preferred name)
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]undecanamide —— C19H30N2O3
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]undecanamide
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-5-{[methyl(phenyl)amino]methyl}-1H-1,2,3-triazole-4-carbohydrazide —— C21H21N9O4
1-(4-amino-1,2,5-oxadiazol-3-yl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-5-{[methyl(phenyl)amino]methyl}-1H-1,2,3-triazole-4-carbohydrazide
—— 3,4,5-trihydroxy-N-[(E)-1-(5-methylthiophen-2-yl)ethylideneamino]benzamide —— C14H14N2O4S
3,4,5-trihydroxy-N-[(E)-1-(5-methylthiophen-2-yl)ethylideneamino]benzamide
—— 3,4,5-trihydroxy-N-[(E)-1-(4-propylphenyl)ethylideneamino]benzamide —— C18H20N2O4
3,4,5-trihydroxy-N-[(E)-1-(4-propylphenyl)ethylideneamino]benzamide
—— N-[(E)-(4-ethoxy-3-methoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C17H18N2O6
N-[(E)-(4-ethoxy-3-methoxyphenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— N-[(E)-1-(4-chlorophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H13ClN2O4
N-[(E)-1-(4-chlorophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— N-[(E)-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]amino]-2-(2,4,5-trichlorophenoxy)acetamide —— C22H18Cl3N3O5S
N-[(E)-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]amino]-2-(2,4,5-trichlorophenoxy)acetamide
—— 1-Hexadecanesulfonic acid (M-hydroxy-alpha-morpholinobenzylidene)-hydrazide —— C27H47N3O4S
1-Hexadecanesulfonic acid (M-hydroxy-alpha-morpholinobenzylidene)-hydrazide
—— N'-[(E)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-(2-toluidino)acetohydrazide —— C17H18BrN3O3
N'-[(E)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-(2-toluidino)acetohydrazide
—— N-[(E)-heptylideneamino]-3,4,5-trihydroxybenzamide —— C14H20N2O4
N-[(E)-heptylideneamino]-3,4,5-trihydroxybenzamide
—— N-benzyl-N'-[(E)-(3-hydroxyphenyl)methylideneamino]butanediamide —— C18H19N3O3
N-benzyl-N'-[(E)-(3-hydroxyphenyl)methylideneamino]butanediamide
—— 2-hydroxy-N-[(E)-(3-hydroxyphenyl)methylideneamino]-3,5-dinitrobenzamide —— C14H10N4O7
2-hydroxy-N-[(E)-(3-hydroxyphenyl)methylideneamino]-3,5-dinitrobenzamide
—— 2-(1H-benzimidazol-2-ylsulfanyl)-N-[(E)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H15BrN4O3S
2-(1H-benzimidazol-2-ylsulfanyl)-N-[(E)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 3-(1H-benzimidazol-1-yl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-2-methylpropanohydrazide —— C19H20N4O3
3-(1H-benzimidazol-1-yl)-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-2-methylpropanohydrazide
—— 2-(2-ethylsulfanyl-6-methylpyrimidin-4-yl)oxy-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H20N4O4S
2-(2-ethylsulfanyl-6-methylpyrimidin-4-yl)oxy-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N'-[(E)-(4-Fluorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide —— C14H11FN2O4
N'-[(E)-(4-Fluorophenyl)methylidene]-3,4,5-trihydroxybenzohydrazide
—— N-[(E)-[2,5-bis(methylsulfanyl)-4-[(E)-[(3,4,5-trihydroxybenzoyl)hydrazinylidene]methyl]thiophen-3-yl]methylideneamino]-3,4,5-trihydroxybenzamide —— C22H20N4O8S3
N-[(E)-[2,5-bis(methylsulfanyl)-4-[(E)-[(3,4,5-trihydroxybenzoyl)hydrazinylidene]methyl]thiophen-3-yl]methylideneamino]-3,4,5-trihydroxybenzamide
—— 2-hydroxy-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylacetamide —— C16H16N2O4
2-hydroxy-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylacetamide
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]decanamide —— C17H26N2O2
N-[(E)-(3-hydroxyphenyl)methylideneamino]decanamide