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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
—— 4-(4-hydroxyphenyl)-N-[(2S)-1-pyrazol-1-ylpropan-2-yl]-3,6-dihydro-2H-pyridine-1-carboxamide —— C18H22N4O2
4-(4-hydroxyphenyl)-N-[(2S)-1-pyrazol-1-ylpropan-2-yl]-3,6-dihydro-2H-pyridine-1-carboxamide
—— N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]pyridine-3-carbohydrazide —— C15H15N3O3
N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]pyridine-3-carbohydrazide
—— 1-[1-(2,4-Dihydroxyphenyl)ethenylamino]-3-(2,6-dimethylphenyl)thiourea —— C17H19N3O2S
1-[1-(2,4-Dihydroxyphenyl)ethenylamino]-3-(2,6-dimethylphenyl)thiourea
—— (3E)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12BrNO3
(3E)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-1H-indol-2-one
—— 2,5-Bis(4-hydroxy-3,5-dimethoxybenzylidene)cyclopentanone —— C23H24O7
2,5-Bis(4-hydroxy-3,5-dimethoxybenzylidene)cyclopentanone
—— 4-(1,3-benzothiazol-2-ylsulfanylmethyl)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]benzohydrazide —— C24H21N3O3S2
4-(1,3-benzothiazol-2-ylsulfanylmethyl)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethenyl]benzohydrazide
—— 4-[[(Z)-2-bromo-3-phenylprop-2-enylidene]amino]phenol —— C15H12BrNO
4-[[(Z)-2-bromo-3-phenylprop-2-enylidene]amino]phenol
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-1-oxidopyridin-1-ium-4-carboxamide —— C14H13N3O4
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-1-oxidopyridin-1-ium-4-carboxamide
—— N-(furan-2-ylmethylideneamino)-3-(2-hydroxyphenyl)propanamide —— C14H14N2O3
N-(furan-2-ylmethylideneamino)-3-(2-hydroxyphenyl)propanamide
—— 4-(3-Morpholin-4-ylpropyliminomethyl)phenol —— C14H20N2O2
4-(3-Morpholin-4-ylpropyliminomethyl)phenol
—— (4-hydroxyphenyl)methylidene-(3-morpholin-4-ylpropyl)azanium —— C14H21N2O2+
(4-hydroxyphenyl)methylidene-(3-morpholin-4-ylpropyl)azanium
—— (7S)-3-(2-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H16FNO3S
(7S)-3-(2-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H16FNO3S
(7R)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H16FNO3S
(7S)-3-(3-fluorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-3-(2-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H16FNO3S
(7R)-3-(2-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO4S
(7S)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO4S
(7R)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-3-(4-chlorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H16ClNO3S
(7S)-3-(4-chlorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— 3-(1,4-dioxaspiro[4.5]decan-8-yl)-1-[(2-hydroxyphenyl)methyl]-1-methylurea —— C17H24N2O4
3-(1,4-dioxaspiro[4.5]decan-8-yl)-1-[(2-hydroxyphenyl)methyl]-1-methylurea
—— (7R)-3-(2-fluorophenyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H18FNO4S
(7R)-3-(2-fluorophenyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO4S
(7S)-7-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-3-(2-fluorophenyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H18FNO4S
(7S)-3-(2-fluorophenyl)-7-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-3-(4-chlorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H16ClNO3S
(7R)-3-(4-chlorophenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C21H19NO4S
(7R)-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(4-hydroxy-3-methoxyphenyl)-3-phenyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H17NO3S
(7S)-7-(4-hydroxy-3-methoxyphenyl)-3-phenyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7S)-7-(3-hydroxy-4-methoxyphenyl)-3-phenyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H17NO3S
(7S)-7-(3-hydroxy-4-methoxyphenyl)-3-phenyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C22H21NO5S
(7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-methoxyphenyl)-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— (7R)-7-(4-hydroxy-3-methoxyphenyl)-3-phenyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one —— C20H17NO3S
(7R)-7-(4-hydroxy-3-methoxyphenyl)-3-phenyl-6,7-dihydro-4H-thieno[3,2-b]pyridin-5-one
—— ethyl (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-[(4-methylbenzoyl)amino]-4-oxothiophene-3-carboxylate —— C22H18N2O7S
ethyl (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-[(4-methylbenzoyl)amino]-4-oxothiophene-3-carboxylate
—— (5Z)-3-ethyl-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C13H12INO3S2
(5Z)-3-ethyl-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 2-(4-Morpholin-4-ium-4-ylbutylsulfanyl)benzene-1,4-diol —— C14H22NO3S+
2-(4-Morpholin-4-ium-4-ylbutylsulfanyl)benzene-1,4-diol
—— 1-[2-(4-Hydroxyphenyl)ethyl]-3-prop-2-enylthiourea —— C12H16N2OS
1-[2-(4-Hydroxyphenyl)ethyl]-3-prop-2-enylthiourea
—— 3-(3-Chlorophenyl)-5-(4-hydroxy-3-iodobenzylidene)-1,3-thiazolidine-2,4-dione —— C16H9ClINO3S
3-(3-Chlorophenyl)-5-(4-hydroxy-3-iodobenzylidene)-1,3-thiazolidine-2,4-dione
—— (2E)-5-bromo-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-6,7-dimethyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one —— C19H15BrN2O3S
(2E)-5-bromo-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-6,7-dimethyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one
—— ethyl (2Z,5S)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2Z,5S)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2Z,5R)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Cl2N2O4S
ethyl (2Z,5R)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-5-(2,5-dimethoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2Z,5R)-5-(2,5-dimethoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4Z)-4-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]-1-(4-iodophenyl)pyrazolidine-3,5-dione —— C20H12IN3O6
(4Z)-4-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]-1-(4-iodophenyl)pyrazolidine-3,5-dione
—— ethyl (2E,5R)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17BrN2O4S2
ethyl (2E,5R)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(prop-2-EN-1-YL)-4,5-dihydro-1H-pyrrole-3-carboxylate —— C18H19NO5
Methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(prop-2-EN-1-YL)-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 2-[2-(4-methoxyphenyl)ethoxysulfanyl]-1H-benzimidazole —— C16H16N2O2S
2-[2-(4-methoxyphenyl)ethoxysulfanyl]-1H-benzimidazole
—— (4E)-1-(3-chlorophenyl)-4-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]pyrazolidine-3,5-dione —— C20H12ClN3O6
(4E)-1-(3-chlorophenyl)-4-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]pyrazolidine-3,5-dione
—— (4E)-1-(4-bromophenyl)-4-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C17H12BrClN2O4
(4E)-1-(4-bromophenyl)-4-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-3-(pyridin-3-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H12N2O2S2
(5E)-5-[(4-hydroxyphenyl)methylidene]-3-(pyridin-3-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one —— C17H9F3N2O4S2
(5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
—— (5E)-5-(3,5-dibromo-4-hydroxybenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9Br2NO3S
(5E)-5-(3,5-dibromo-4-hydroxybenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione
—— (5Z)-3-(3-chlorophenyl)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H8Br2ClNO2S2
(5Z)-3-(3-chlorophenyl)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-Benzyl-2-(benzylimino)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidin-4-one —— C25H21BrN2O3S
3-Benzyl-2-(benzylimino)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidin-4-one
—— (5E)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H9Br2NO2S2
(5E)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one