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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-(4-hydroxy-3-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid —— C13H14N2O5
6-(4-hydroxy-3-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid
—— 1,5-Dimethylimidazole;ethane;phenol —— C15H26N2O
1,5-Dimethylimidazole;ethane;phenol
—— 4-Butan-2-yl-2-methoxyphenol;(2-ethyl-2-adamantyl) 2,2-dimethylbutanoate —— C29H46O4
4-Butan-2-yl-2-methoxyphenol;(2-ethyl-2-adamantyl) 2,2-dimethylbutanoate
—— 2-(1H-benzimidazol-2-ylsulfanyl)-N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H15BrN4O3S
2-(1H-benzimidazol-2-ylsulfanyl)-N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2,4,5-Tris(prop-2-enyl)benzene-1,3-diol —— C15H18O2
2,4,5-Tris(prop-2-enyl)benzene-1,3-diol
—— (3E)-3-[7-(2-hydroxy-5-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
(3E)-3-[7-(2-hydroxy-5-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 1-N'-(ethoxymethyl)-3-N'-[2-(4-hydroxyphenyl)ethoxymethyl]propanedihydrazide —— C15H24N4O5
1-N'-(ethoxymethyl)-3-N'-[2-(4-hydroxyphenyl)ethoxymethyl]propanedihydrazide
—— Ethane;ethylbenzene;methylsulfonylmethane;phenol —— C22H40O3S
Ethane;ethylbenzene;methylsulfonylmethane;phenol
—— methyl (2Z)-2-[[2-(cyanomethoxy)phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H21N3O6S
methyl (2Z)-2-[[2-(cyanomethoxy)phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2,4-diethyl-3-[2-(2H-pyridin-1-yl)ethylideneamino]phenol —— C17H22N2O
2,4-diethyl-3-[2-(2H-pyridin-1-yl)ethylideneamino]phenol
—— 5-[(E)-1-(3,5-Dibromo-2-hydroxy-4-methoxyphenyl)methylidene]-2-thioxotetrahydro-4H-imidazol-4-one —— C11H8Br2N2O3S
5-[(E)-1-(3,5-Dibromo-2-hydroxy-4-methoxyphenyl)methylidene]-2-thioxotetrahydro-4H-imidazol-4-one
—— 2,5-Bis{3-[ethyl(2-methoxybenzyl)amino]propylamino}-[1,4]-benzoquinone —— C32H44N4O4
2,5-Bis{3-[ethyl(2-methoxybenzyl)amino]propylamino}-[1,4]-benzoquinone
—— 3-bromo-2-methoxy-5-[(Z)-[(2-nitrophenyl)hydrazinylidene]methyl]phenol —— C14H12BrN3O4
3-bromo-2-methoxy-5-[(Z)-[(2-nitrophenyl)hydrazinylidene]methyl]phenol
—— 3,4,5-trihydroxy-N'-[(1Z)-1-(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide —— C15H14N2O6
3,4,5-trihydroxy-N'-[(1Z)-1-(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide
—— 4-(4-Hydroxyphenyl)butan-2-one;4-methylphenol —— C17H20O3
4-(4-Hydroxyphenyl)butan-2-one;4-methylphenol
—— (4Z)-2-(2,4-dimethylphenyl)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methylpyrazol-3-one —— C19H18N4O4
(4Z)-2-(2,4-dimethylphenyl)-4-[(2-hydroxy-4-nitroanilino)methylidene]-5-methylpyrazol-3-one
—— 3-Butyl-5-(2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one —— C14H15NO2S2
3-Butyl-5-(2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one
—— Ethane;phenol;2,2,3-trimethyloctane —— C19H36O
Ethane;phenol;2,2,3-trimethyloctane
—— 4-Octylphenol;propane —— C48H82O3
4-Octylphenol;propane
—— 4-Amino-5-[2-(5-chloro-2,4-dihydroxyphenyl)ethyl]-1,2-oxazole-3-carboxamide —— C12H12ClN3O4
4-Amino-5-[2-(5-chloro-2,4-dihydroxyphenyl)ethyl]-1,2-oxazole-3-carboxamide
—— 9-(5-Bromo-2-hydroxyphenyl)-5,13-dioxa-2-azatricyclo[8.4.0.03,8]tetradeca-1,3(8)-diene-7,11-dione —— C17H14BrNO5
9-(5-Bromo-2-hydroxyphenyl)-5,13-dioxa-2-azatricyclo[8.4.0.03,8]tetradeca-1,3(8)-diene-7,11-dione
—— Ethane;ethanol;phenol;propane —— C13H26O2
Ethane;ethanol;phenol;propane
—— (5E)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-3-(4-fluorobenzyl)-1,3-thiazolidine-2,4-dione —— C17H10BrClFNO3S
(5E)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-3-(4-fluorobenzyl)-1,3-thiazolidine-2,4-dione
—— 3-Amino-4-(2,6-dihydroxy-4-methylphenyl)-4,4-dihydroxybutan-2-one —— C11H15NO5
3-Amino-4-(2,6-dihydroxy-4-methylphenyl)-4,4-dihydroxybutan-2-one
—— benzene;ethane;pentane;phenol;propane —— C71H120O4
benzene;ethane;pentane;phenol;propane
—— Azetidin-1-yl-(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methanone —— C14H17NO3
Azetidin-1-yl-(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methanone
—— (4-Ethyl-2-hydroxyphenyl)methanediol —— C9H12O3
(4-Ethyl-2-hydroxyphenyl)methanediol
—— 1-(2-Hydroxy-5-phenylmethoxyphenyl)-3-methyl-13-phenylmethoxytrideca-2,4-dien-1-one —— C34H40O4
1-(2-Hydroxy-5-phenylmethoxyphenyl)-3-methyl-13-phenylmethoxytrideca-2,4-dien-1-one
—— 5-(1-Amino-3-methylbutyl)-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde —— C13H17NO5
5-(1-Amino-3-methylbutyl)-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
—— 2-Methyl-5-(1,3,4-oxadiazol-2-yl)phenol —— C9H8N2O2
2-Methyl-5-(1,3,4-oxadiazol-2-yl)phenol
—— 4-[1-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-yliminoethyl]-2,6-dimethoxyphenol —— C21H29N2O6P
4-[1-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-yliminoethyl]-2,6-dimethoxyphenol
—— 4-methyl-3-[4-[(2,4,5-trihydroxyphenyl)methyldiazenyl]phenyl]-4,5-dihydro-1H-pyridazin-6-one —— C18H18N4O4
4-methyl-3-[4-[(2,4,5-trihydroxyphenyl)methyldiazenyl]phenyl]-4,5-dihydro-1H-pyridazin-6-one
—— 3-[(Z)-[(4-amino-5-methyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]phenol —— C10H12N6O
3-[(Z)-[(4-amino-5-methyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]phenol
—— 4-(3-Hydroxypent-1-enyl)-2-methoxyphenol —— C12H16O3
4-(3-Hydroxypent-1-enyl)-2-methoxyphenol
—— ethane;2-methyl-1H-imidazole;phenol —— C14H24N2O
ethane;2-methyl-1H-imidazole;phenol
—— 2-Amino-3-methylphenol;2-(2-hydroxy-6-methylanilino)-4-methylpentanenitrile —— C20H27N3O2
2-Amino-3-methylphenol;2-(2-hydroxy-6-methylanilino)-4-methylpentanenitrile
—— 5-Nitro-2-(pyridin-2-ylamino)phenol —— C11H9N3O3
5-Nitro-2-(pyridin-2-ylamino)phenol
—— 5-[[[4-(3-chloro-4-hydroxyanilino)-6-(cyclohexylmethylamino)-1,3,5-triazin-2-yl]amino]methyl]-4-hydroxy-3H-1,3-thiazol-2-one —— C20H24ClN7O3S
5-[[[4-(3-chloro-4-hydroxyanilino)-6-(cyclohexylmethylamino)-1,3,5-triazin-2-yl]amino]methyl]-4-hydroxy-3H-1,3-thiazol-2-one
—— 4-[2-[(2,6-Dimethylpyridin-3-yl)amino]-1-(1-methyl-2-oxo-1,2lambda5-azaphosphinan-2-yl)ethyl]-2-methoxyphenol —— C21H30N3O3P
4-[2-[(2,6-Dimethylpyridin-3-yl)amino]-1-(1-methyl-2-oxo-1,2lambda5-azaphosphinan-2-yl)ethyl]-2-methoxyphenol
—— (2E,5E)-5-(5-bromo-3-chloro-2-hydroxybenzylidene)-3-methyl-2-(methylimino)-1,3-thiazolidin-4-one —— C12H10BrClN2O2S
(2E,5E)-5-(5-bromo-3-chloro-2-hydroxybenzylidene)-3-methyl-2-(methylimino)-1,3-thiazolidin-4-one
—— 2-(Nitrosomethyl)-6-prop-2-enylphenol —— C10H11NO2
2-(Nitrosomethyl)-6-prop-2-enylphenol
—— 2,4,6-Trihydroxy-5-(3-methyl-1-nitrosobutyl)benzene-1,3-dicarbaldehyde —— C13H15NO6
2,4,6-Trihydroxy-5-(3-methyl-1-nitrosobutyl)benzene-1,3-dicarbaldehyde
—— (3Z)-2-amino-4-(5-bromo-2-hydroxy-3-methoxyphenyl)but-3-ene-1,1,3-tricarbonitrile —— C14H11BrN4O2
(3Z)-2-amino-4-(5-bromo-2-hydroxy-3-methoxyphenyl)but-3-ene-1,1,3-tricarbonitrile
—— 2-[3-(4-Hydroxyphenyl)-2,5-dihydro-1,2-oxazol-5-yl]acetic acid —— C11H11NO4
2-[3-(4-Hydroxyphenyl)-2,5-dihydro-1,2-oxazol-5-yl]acetic acid
—— 4-[3-(furan-3-yl)-2-(1H-pyrrol-2-yl)propyl]phenol —— C17H17NO2
4-[3-(furan-3-yl)-2-(1H-pyrrol-2-yl)propyl]phenol
—— 6-(2-Ethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyldiazenyl]thieno[3,2-d]pyrimidine-7-carbonitrile —— C24H21N5O4S
6-(2-Ethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyldiazenyl]thieno[3,2-d]pyrimidine-7-carbonitrile
—— N-[4-[4-[(3-hydroxy-4-methoxyphenyl)methyldiazenyl]-7-methylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide —— C23H21N5O3S
N-[4-[4-[(3-hydroxy-4-methoxyphenyl)methyldiazenyl]-7-methylthieno[3,2-d]pyrimidin-6-yl]phenyl]acetamide
—— 4-(2-Hydroxy-4-methoxy-phenyl)-4-oxo-but-2-enoic acid (cyclohexylcarbamoyl-pyridin-4-yl-methyl)-(2-methoxy-benzyl)-amide —— C32H35N3O6
4-(2-Hydroxy-4-methoxy-phenyl)-4-oxo-but-2-enoic acid (cyclohexylcarbamoyl-pyridin-4-yl-methyl)-(2-methoxy-benzyl)-amide
—— (E)-N-benzyl-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide —— C26H30N2O5
(E)-N-benzyl-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxobut-2-enamide
—— (E)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylphenyl)ethyl]-4-oxobut-2-enamide —— C28H34N2O5
(E)-N-[2-(cyclohexylamino)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-N-[2-(3-methylphenyl)ethyl]-4-oxobut-2-enamide