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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
—— (3S)-N-[4-(furan-2-yl)phenyl]-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidine-3-carboxamide —— C26H28N2O4
(3S)-N-[4-(furan-2-yl)phenyl]-1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidine-3-carboxamide
—— 2-methoxy-4-[(Z)-3-[(3S)-3-pyrrolidin-1-ylpiperidin-1-yl]prop-1-enyl]phenol —— C19H28N2O2
2-methoxy-4-[(Z)-3-[(3S)-3-pyrrolidin-1-ylpiperidin-1-yl]prop-1-enyl]phenol
—— 4-[(Z)-3-[(3R)-3-(2-hydroxyethyl)-4-(thiophen-3-ylmethyl)piperazin-1-yl]prop-1-enyl]-2-methoxyphenol —— C21H28N2O3S
4-[(Z)-3-[(3R)-3-(2-hydroxyethyl)-4-(thiophen-3-ylmethyl)piperazin-1-yl]prop-1-enyl]-2-methoxyphenol
—— (1S,5S,7S)-3-[(3-chlorophenyl)methyl]-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one —— C25H27ClN2O3
(1S,5S,7S)-3-[(3-chlorophenyl)methyl]-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one
—— (5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-[3-(trifluoromethyl)phenyl]imino-1,3-thiazolidin-4-one —— C18H13F3N2O3S
(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-[3-(trifluoromethyl)phenyl]imino-1,3-thiazolidin-4-one
—— (5E)-2-cyclohexylimino-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17N3O4S
(5E)-2-cyclohexylimino-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-cyclohexylimino-1,3-thiazolidin-4-one —— C17H19BrN2O3S
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-cyclohexylimino-1,3-thiazolidin-4-one
—— 4-[(2S)-2-(bromomethyl)-1,3-dioxol-4-yl]phenol —— C10H9BrO3
4-[(2S)-2-(bromomethyl)-1,3-dioxol-4-yl]phenol
—— (5E)-2-cyclohexylimino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H22N2O2S
(5E)-2-cyclohexylimino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (3Z)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-1-methylindol-2-one —— C17H14BrNO3
(3Z)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-1-methylindol-2-one
—— (3Z)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one —— C17H14ClNO3
(3Z)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one
—— (Z)-2-(2,5-dichlorophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile —— C16H11Cl2NO4S
(Z)-2-(2,5-dichlorophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— (Z)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(2,5-dichlorophenyl)sulfonylprop-2-enenitrile —— C16H10BrCl2NO4S
(Z)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(2,5-dichlorophenyl)sulfonylprop-2-enenitrile
—— (5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H14N2O4S2
(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C19H18N2O4S
(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-methylanilino)-1,3-thiazol-4-one —— C18H15BrN2O3S
(5E)-5-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-methylanilino)-1,3-thiazol-4-one
—— 6-[(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C18H21NO6S2
6-[(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-methylanilino)-1,3-thiazol-4-one —— C18H16N2O3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(2-methylanilino)-1,3-thiazol-4-one
—— (5E)-2-(2,5-dimethylanilino)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C19H18N2O3S
(5E)-2-(2,5-dimethylanilino)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (Z)-3-(3-hydroxy-4-methoxyphenyl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile —— C17H18N4O2
(Z)-3-(3-hydroxy-4-methoxyphenyl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile
—— (5E)-2-benzylimino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H16N2O3S
(5E)-2-benzylimino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylanilino)-1,3-thiazol-4-one —— C18H16N2O3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylanilino)-1,3-thiazol-4-one
—— (3Z)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one —— C16H11BrClNO3
(3Z)-3-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-6-chloro-1H-indol-2-one
—— (3Z)-5-chloro-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12ClNO3
(3Z)-5-chloro-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one
—— 2-methoxy-6-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]-4-prop-2-enylphenol —— C24H30N2O2
2-methoxy-6-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]-4-prop-2-enylphenol
—— (E)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile —— C15H11BrN2O2
(E)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H12ClNO3S2
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (3Z)-6-chloro-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12ClNO3
(3Z)-6-chloro-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one
—— (5Z)-3-ethyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H15NO2S2
(5Z)-3-ethyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (3Z)-5-chloro-3-[(4-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12ClNO3
(3Z)-5-chloro-3-[(4-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one
—— 2-[[(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile —— C18H10BrN3O5S
2-[[(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile
—— (5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C21H15ClN2O3S
(5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— 2-[[(5Z)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile —— C18H11N3O5S
2-[[(5Z)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile
—— (Z)-3-(4-chloro-2-methylpyrazol-3-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C14H13ClN2O3
(Z)-3-(4-chloro-2-methylpyrazol-3-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— 3-[[(S)-benzimidazol-1-yl-(2-hydroxy-5-nitrophenyl)methyl]amino]benzoic acid —— C21H16N4O5
3-[[(S)-benzimidazol-1-yl-(2-hydroxy-5-nitrophenyl)methyl]amino]benzoic acid
—— 3-[[(R)-benzimidazol-1-yl-(2-hydroxy-5-nitrophenyl)methyl]amino]benzoic acid —— C21H16N4O5
3-[[(R)-benzimidazol-1-yl-(2-hydroxy-5-nitrophenyl)methyl]amino]benzoic acid
—— methyl (2R)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-piperidin-1-ylpropanoate —— C17H22F3NO5
methyl (2R)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-piperidin-1-ylpropanoate
—— methyl (2R)-2-(3,4-dichloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C18H16Cl2F3NO5
methyl (2R)-2-(3,4-dichloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-piperidin-1-ylpropanoate —— C17H22F3NO5
methyl (2S)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-piperidin-1-ylpropanoate
—— methyl (2S)-2-(3,4-dichloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C18H16Cl2F3NO5
methyl (2S)-2-(3,4-dichloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— methyl (2S)-2-(3-chloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C18H17ClF3NO5
methyl (2S)-2-(3-chloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— methyl (2R)-2-(3-chloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C18H17ClF3NO5
methyl (2R)-2-(3-chloroanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— ethyl (2Z,7S)-2-(1,3-benzodioxol-5-ylmethylidene)-7-(2-hydroxy-5-methoxyphenyl)-5-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22N2O7S
ethyl (2Z,7S)-2-(1,3-benzodioxol-5-ylmethylidene)-7-(2-hydroxy-5-methoxyphenyl)-5-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,7R)-2-(1,3-benzodioxol-5-ylmethylidene)-7-(2-hydroxy-5-methoxyphenyl)-5-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22N2O7S
ethyl (2Z,7R)-2-(1,3-benzodioxol-5-ylmethylidene)-7-(2-hydroxy-5-methoxyphenyl)-5-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-2-(3H-1,3-benzothiazol-2-ylidenemethyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C19H14N2O3S2
(5Z)-2-(3H-1,3-benzothiazol-2-ylidenemethyl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-2-(3H-1,3-benzothiazol-2-ylidenemethyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazol-4-one —— C20H16N2O4S2
(5Z)-2-(3H-1,3-benzothiazol-2-ylidenemethyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(2-hydroxyphenyl)methylidene]-3-(prop-2-enylamino)-1,3-thiazolidin-4-one —— C17H17N5O2S2
(5Z)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(2-hydroxyphenyl)methylidene]-3-(prop-2-enylamino)-1,3-thiazolidin-4-one
—— 2,4,6-tribromo-3-[(Z)-(3,5-dimethyl-1,2,4-triazol-4-yl)iminomethyl]phenol —— C11H9Br3N4O
2,4,6-tribromo-3-[(Z)-(3,5-dimethyl-1,2,4-triazol-4-yl)iminomethyl]phenol
—— ethyl (2E,5R)-5-(3-ethoxy-4-hydroxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2E,5R)-5-(3-ethoxy-4-hydroxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(3-ethoxy-4-hydroxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2E,5S)-5-(3-ethoxy-4-hydroxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate