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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
—— (5Z)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H7Br2NO2S2
(5Z)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-(2-hydroxybenzylidene)-3-methyl-2-thioxo-1,3-oxazolidin-4-one —— C11H9NO3S
(5Z)-5-(2-hydroxybenzylidene)-3-methyl-2-thioxo-1,3-oxazolidin-4-one
—— (5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2,4-dimethylphenyl)-2-thioxo-1,3-thiazolidin-4-one —— C19H16BrNO3S2
(5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2,4-dimethylphenyl)-2-thioxo-1,3-thiazolidin-4-one
—— 3-(3-Fluorophenyl)-5-(2-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C17H12FNO3S2
3-(3-Fluorophenyl)-5-(2-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 3-(4-Chlorophenyl)-5-(2-hydroxy-3-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C17H12ClNO4S
3-(4-Chlorophenyl)-5-(2-hydroxy-3-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— ethyl (2Z,5R)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z,5R)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H9BrN2O4S2
(5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-3-(2,4-dimethylphenyl)-2-thioxo-1,3-thiazolidin-4-one —— C18H13BrN2O4S2
(5E)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-3-(2,4-dimethylphenyl)-2-thioxo-1,3-thiazolidin-4-one
—— ethyl (2Z,5S)-5-[4-(dimethylamino)phenyl]-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H27N3O5S
ethyl (2Z,5S)-5-[4-(dimethylamino)phenyl]-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-3-benzyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
(5E)-3-benzyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H9BrN2O4S2
(5E)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (2Z,5S)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21ClN2O5S
ethyl (2Z,5S)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4Z)-4-(2-hydroxy-3-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione —— C18H16N2O4
(4Z)-4-(2-hydroxy-3-methoxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione
—— ethyl (2Z,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O5S
ethyl (2Z,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H7BrClNO2S2
(5E)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-(4-hydroxyphenyl)-N-[[3-(1,2,4-triazol-1-ylmethyl)phenyl]methyl]-3,6-dihydro-2H-pyridine-1-carboxamide —— C22H23N5O2
4-(4-hydroxyphenyl)-N-[[3-(1,2,4-triazol-1-ylmethyl)phenyl]methyl]-3,6-dihydro-2H-pyridine-1-carboxamide
—— (5E)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H8N2O4S2
(5E)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-(4-methoxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12N2O5S2
(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-(4-methoxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H8ClNO2S2
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methylphenyl)-1,3-thiazol-4-one —— C18H14BrNO3S
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-methylphenyl)-1,3-thiazol-4-one
—— (4E)-4-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-1-(4-chlorophenyl)pyrazolidine-3,5-dione —— C16H9BrCl2N2O3
(4E)-4-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-1-(4-chlorophenyl)pyrazolidine-3,5-dione
—— (4E)-4-[(5-chloro-2-hydroxyphenyl)methylidene]-1-(3-chlorophenyl)pyrazolidine-3,5-dione —— C16H10Cl2N2O3
(4E)-4-[(5-chloro-2-hydroxyphenyl)methylidene]-1-(3-chlorophenyl)pyrazolidine-3,5-dione
—— (5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C11H8BrNO3S2
(5E)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— N-[(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-4-methylbenzenesulfonamide —— C17H13N3O6S2
N-[(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-4-methylbenzenesulfonamide
—— 2-[[(E)-3-(4-chlorophenyl)prop-2-enylidene]amino]-4-methylphenol —— C16H14ClNO
2-[[(E)-3-(4-chlorophenyl)prop-2-enylidene]amino]-4-methylphenol
—— 3-Allyl-5-(3-hydroxy-4-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C14H13NO3S2
3-Allyl-5-(3-hydroxy-4-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— ethyl (4S,5R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C16H20N2O6
ethyl (4S,5R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— benzyl (6R,7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methylidene-6,7-dihydro-1H-tetrazolo[1,5-a]pyrimidine-6-carboxylate —— C20H19N5O4
benzyl (6R,7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methylidene-6,7-dihydro-1H-tetrazolo[1,5-a]pyrimidine-6-carboxylate
—— methyl (4R,5S)-4-(2-bromo-3-hydroxy-4-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C14H15BrN2O5
methyl (4R,5S)-4-(2-bromo-3-hydroxy-4-methoxyphenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— methyl (4R,5S)-4-(3-bromo-2-hydroxy-5-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate —— C13H12BrN3O6
methyl (4R,5S)-4-(3-bromo-2-hydroxy-5-nitrophenyl)-6-methylidene-2-oxo-1,3-diazinane-5-carboxylate
—— 2-Bromo-4-({4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl}methyl)-6-methoxyphenol —— C16H25BrN2O4
2-Bromo-4-({4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl}methyl)-6-methoxyphenol
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-2-[4-[(5E)-5-[(4-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-yl]-1,3-thiazol-4-one —— C24H20N4O4S2
(5E)-5-[(4-hydroxyphenyl)methylidene]-2-[4-[(5E)-5-[(4-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-yl]-1,3-thiazol-4-one
—— ethyl (2E,5R)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17N3O6S2
ethyl (2E,5R)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-(2-Hydroxy-5-methylanilino)-1-(5-methylfuran-2-yl)but-3-en-1-one —— C16H17NO3
3-(2-Hydroxy-5-methylanilino)-1-(5-methylfuran-2-yl)but-3-en-1-one
—— (5Z)-5-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C11H9IN2O3S
(5Z)-5-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 4-amino-N'-[(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboximidamide —— C10H10N6O2
4-amino-N'-[(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboximidamide
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-(2-methylphenyl)-1,3-diazinane-2,4,6-trione —— C19H16N2O5
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-(2-methylphenyl)-1,3-diazinane-2,4,6-trione
—— 4-[[2-(1,3-Benzodioxol-5-yl)ethylamino]methyl]-2-methoxyphenol 801227-59-8 C17H19NO4
4-[[2-(1,3-Benzodioxol-5-yl)ethylamino]methyl]-2-methoxyphenol
—— (5Z)-1-ethyl-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C14H14N2O4S
(5Z)-1-ethyl-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5E)-3-ethyl-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1-methyl-2-sulfanylideneimidazolidin-4-one —— C13H13N3O4S
(5E)-3-ethyl-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1-methyl-2-sulfanylideneimidazolidin-4-one
—— (5E)-1-(4-ethylphenyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione —— C20H18N2O5
(5E)-1-(4-ethylphenyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
—— (5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-dimethyl-2-thioxoimidazolidin-4-one —— C13H13BrN2O3S
(5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-dimethyl-2-thioxoimidazolidin-4-one
—— (5Z)-5-(3-hydroxy-4-methoxybenzylidene)-3-(2-methylpropyl)-2-thioxo-1,3-thiazolidin-4-one —— C15H17NO3S2
(5Z)-5-(3-hydroxy-4-methoxybenzylidene)-3-(2-methylpropyl)-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-3-butyl-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C15H16ClNO4S
(5Z)-3-butyl-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— (5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyphenyl)-1,3-thiazolidine-2,4-dione —— C18H14BrNO5S
(5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyphenyl)-1,3-thiazolidine-2,4-dione
—— N-[(5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]acetamide —— C13H11BrN2O4S
N-[(5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]acetamide
—— (4Z)-1-(4-fluorophenyl)-4-(4-hydroxy-3-nitrobenzylidene)pyrazolidine-3,5-dione —— C16H10FN3O5
(4Z)-1-(4-fluorophenyl)-4-(4-hydroxy-3-nitrobenzylidene)pyrazolidine-3,5-dione
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-(4-methoxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H14ClNO4S2
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-(4-methoxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-benzyl-2-thioxo-5-(2,4,6-trichloro-3-hydroxybenzylidene)-1,3-thiazolidin-4-one —— C17H10Cl3NO2S2
(5Z)-3-benzyl-2-thioxo-5-(2,4,6-trichloro-3-hydroxybenzylidene)-1,3-thiazolidin-4-one
—— ethyl (Z)-5-(3-hydroxy-4-methoxybenzylidene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate —— C21H19NO5S
ethyl (Z)-5-(3-hydroxy-4-methoxybenzylidene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate