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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-(5-Bromothiophen-2-yl)-3-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-1,3-thiazolidin-4-one —— C16H16BrNO3S2
2-(5-Bromothiophen-2-yl)-3-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-1,3-thiazolidin-4-one
—— N-[(3-hydroxyphenyl)methylideneamino]nonanamide —— C16H24N2O2
N-[(3-hydroxyphenyl)methylideneamino]nonanamide
—— 3-Ethyl-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C12H11N3O4S
3-Ethyl-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 2-Tert-butyl-3-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-thiazolidin-4-one —— C15H21NO3S
2-Tert-butyl-3-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-thiazolidin-4-one
—— N'-(2,4-dimethylphenyl)-N'-[1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N-(1,3-thiazol-2-yl)butanediamide —— C29H30N4O5S2
N'-(2,4-dimethylphenyl)-N'-[1-(4-hydroxy-3-methoxyphenyl)-2-oxo-2-(thiophen-2-ylmethylamino)ethyl]-N-(1,3-thiazol-2-yl)butanediamide
—— 1-[(E)-[(2-Hydroxy-5-nitrophenyl)methylidene]amino]-3-phenylurea —— C14H12N4O4
1-[(E)-[(2-Hydroxy-5-nitrophenyl)methylidene]amino]-3-phenylurea
—— 3-amino-5-(3,4-dihydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C10H8N2O3S2
3-amino-5-(3,4-dihydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— ethyl 5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18FN3O6S
ethyl 5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(4-Hydroxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one —— C14H14N2O3S
5-[(4-Hydroxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-1,3-thiazolidine-2,4-dione —— C14H14BrNO4S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-propyl-1,3-thiazolidine-2,4-dione
—— N-(4-fluorophenyl)-2-[5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C19H15FN2O5S
N-(4-fluorophenyl)-2-[5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(pyridin-3-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H14N2O3S2
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(pyridin-3-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[(2-Cyclohexylimino-4-methyl-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,3-triol —— C17H21N3O3S
4-[(2-Cyclohexylimino-4-methyl-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,3-triol
—— 3-[(5Z)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C14H11BrNO5S2-
3-[(5Z)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
—— methyl (4R,5S)-4-(3,4-dihydroxyphenyl)-6-methylidene-2-sulfanylidene-1,3-diazinane-5-carboxylate —— C13H14N2O4S
methyl (4R,5S)-4-(3,4-dihydroxyphenyl)-6-methylidene-2-sulfanylidene-1,3-diazinane-5-carboxylate
—— (5E)-5-[(4-hydroxy-3-iodophenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione —— C13H8INO3S
(5E)-5-[(4-hydroxy-3-iodophenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione
—— (4Z)-4-(5-chloro-2-hydroxy-3-nitrobenzylidene)-1-(3,4-dimethylphenyl)pyrazolidine-3,5-dione —— C18H14ClN3O5
(4Z)-4-(5-chloro-2-hydroxy-3-nitrobenzylidene)-1-(3,4-dimethylphenyl)pyrazolidine-3,5-dione
—— (5Z)-5-[(4-hydroxy-3-iodophenyl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione —— C11H8INO3S
(5Z)-5-[(4-hydroxy-3-iodophenyl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione
—— ethyl (2Z,5S)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z,5S)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C11H9BrN2O3S
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5Z)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one —— C17H9F3N2O4S2
(5Z)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
—— (4E)-5-hydroxy-4-(4-hydroxybenzylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one —— C16H12N2O3
(4E)-5-hydroxy-4-(4-hydroxybenzylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
—— ethyl (2Z,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 (2Z,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
—— 1-[(3R)-5-butyl-3-hydroxy-3-(trifluoromethyl)-1H-pyrazol-2-yl]-3-(2-hydroxyphenyl)propan-1-one —— C17H21F3N2O3
1-[(3R)-5-butyl-3-hydroxy-3-(trifluoromethyl)-1H-pyrazol-2-yl]-3-(2-hydroxyphenyl)propan-1-one
—— ethyl (2Z,5S)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2Z,5S)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-({[4-(2,5-Dimethylphenyl)-5-propyl-1,3-thiazol-2-yl]amino}methyl)-6-methoxyphenol —— C22H26N2O2S
2-({[4-(2,5-Dimethylphenyl)-5-propyl-1,3-thiazol-2-yl]amino}methyl)-6-methoxyphenol
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-(2-methoxyphenyl)-1,3-diazinane-2,4,6-trione —— C19H16N2O6
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-(2-methoxyphenyl)-1,3-diazinane-2,4,6-trione
—— (5Z)-3-(furan-2-ylmethyl)-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C15H10N2O5S2
(5Z)-3-(furan-2-ylmethyl)-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 1-[(2-hydroxyphenyl)methyl]-3-[1-(2-methoxyethyl)pyrazol-4-yl]-1-[[(2R)-oxolan-2-yl]methyl]urea —— C19H26N4O4
1-[(2-hydroxyphenyl)methyl]-3-[1-(2-methoxyethyl)pyrazol-4-yl]-1-[[(2R)-oxolan-2-yl]methyl]urea
—— 1-[(2-hydroxyphenyl)methyl]-3-[1-(2-methoxyethyl)pyrazol-4-yl]-1-[[(2S)-oxolan-2-yl]methyl]urea —— C19H26N4O4
1-[(2-hydroxyphenyl)methyl]-3-[1-(2-methoxyethyl)pyrazol-4-yl]-1-[[(2S)-oxolan-2-yl]methyl]urea
—— (5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-[2-(4-methylphenoxy)ethyl]-1,3-thiazolidine-2,4-dione —— C20H18BrNO5S
(5Z)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-[2-(4-methylphenoxy)ethyl]-1,3-thiazolidine-2,4-dione
—— 3-(Octyliminomethyl)phenol 414895-75-3 C15H23NO
3-(Octyliminomethyl)phenol
—— (2Z,5E)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C20H19IN2O4S
(2Z,5E)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(3S)-1,1-dioxothiolan-3-yl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H14BrNO5S3
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(3S)-1,1-dioxothiolan-3-yl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2E,5R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-N-(2-methylphenyl)-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C27H23N3O4S2
(2E,5R)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-N-(2-methylphenyl)-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— ethyl (2E,5R)-2-[(2-hydroxy-5-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-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (2E,5S)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H20N2O5S
methyl (2E,5S)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (4E,5R,6S)-4-[(4-fluorophenyl)sulfonylmethylidene]-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxo-1,3-diazinane-5-carboxylate —— C22H23FN2O8S
ethyl (4E,5R,6S)-4-[(4-fluorophenyl)sulfonylmethylidene]-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxo-1,3-diazinane-5-carboxylate
—— (5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-propyl-2-thioxo-1,3-thiazolidin-4-one —— C14H15NO3S2
(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-propyl-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-5-(4-hydroxy-3-methoxybenzylidene)-2-[(4-hydroxyphenyl)(methyl)amino]-1,3-thiazol-4(5H)-one —— C18H16N2O4S
(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-2-[(4-hydroxyphenyl)(methyl)amino]-1,3-thiazol-4(5H)-one
—— 7-(4-Butylphenyl)-5-hydroxy-1,3-benzoxathiol-2-one —— C17H16O3S
7-(4-Butylphenyl)-5-hydroxy-1,3-benzoxathiol-2-one
—— (4S)-6-amino-4-(5-chloro-2-hydroxyphenyl)-3-(trifluoromethyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C14H8ClF3N4O2
(4S)-6-amino-4-(5-chloro-2-hydroxyphenyl)-3-(trifluoromethyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 6-[(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C17H19NO5S2
6-[(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— 4-[(5E)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]butanoic acid —— C14H13NO5S2
4-[(5E)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]butanoic acid
—— 2-(5-aminotetrazol-1-yl)-N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylideneamino]acetamide —— C11H12BrN7O3
2-(5-aminotetrazol-1-yl)-N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylideneamino]acetamide
—— ethyl (2Z,5S)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O5S2
ethyl (2Z,5S)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (3S)-1-(2,3-dihydro-1H-inden-5-yl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxamide —— C22H24N2O4
(3S)-1-(2,3-dihydro-1H-inden-5-yl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxamide
—— 5-(2-chlorophenyl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]furan-2-carboxamide —— C19H16ClNO4
5-(2-chlorophenyl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]furan-2-carboxamide
—— (2R)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-nitrophenyl)sulfanylpropanamide —— C17H18N2O5S
(2R)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-nitrophenyl)sulfanylpropanamide
—— (2S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-nitrophenyl)sulfanylpropanamide —— C17H18N2O5S
(2S)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(4-nitrophenyl)sulfanylpropanamide