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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
—— (E)-3-(5-bromothiophen-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C14H11BrO3S
(E)-3-(5-bromothiophen-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— ethyl (2Z)-2-[(5Z)-5-[(3-hydroxyphenyl)methylidene]-3-(2-morpholin-4-yl-2-oxoethyl)-4-oxo-1,3-thiazolidin-2-ylidene]acetate —— C20H22N2O6S
ethyl (2Z)-2-[(5Z)-5-[(3-hydroxyphenyl)methylidene]-3-(2-morpholin-4-yl-2-oxoethyl)-4-oxo-1,3-thiazolidin-2-ylidene]acetate
—— N-[4-[(E)-3-(4-hydroxy-3-methoxyphenyl)-3-oxoprop-1-enyl]-1,3-thiazol-2-yl]-N-phenylacetamide —— C21H18N2O4S
N-[4-[(E)-3-(4-hydroxy-3-methoxyphenyl)-3-oxoprop-1-enyl]-1,3-thiazol-2-yl]-N-phenylacetamide
—— (E)-3-[5-chloro-1-[(3R)-1,1-dioxothiolan-3-yl]-3-methylpyrazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C18H19ClN2O5S
(E)-3-[5-chloro-1-[(3R)-1,1-dioxothiolan-3-yl]-3-methylpyrazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (E)-3-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C15H11ClN2O3S
(E)-3-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (E)-1-(4-hydroxy-3-methoxyphenyl)-3-thiophen-2-ylprop-2-en-1-one —— C14H12O3S
(E)-1-(4-hydroxy-3-methoxyphenyl)-3-thiophen-2-ylprop-2-en-1-one
—— (E)-3-[5-chloro-1-[(4-fluorophenyl)methyl]-3-methylpyrazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C21H18ClFN2O3
(E)-3-[5-chloro-1-[(4-fluorophenyl)methyl]-3-methylpyrazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— 4-bromo-2-methoxy-5-[(E)-2-(6-methoxy-1,3-benzothiazol-2-yl)ethenyl]phenol —— C17H14BrNO3S
4-bromo-2-methoxy-5-[(E)-2-(6-methoxy-1,3-benzothiazol-2-yl)ethenyl]phenol
—— ethyl (2Z)-2-[(5Z)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-ylidene]acetate —— C14H13NO3S2
ethyl (2Z)-2-[(5Z)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-ylidene]acetate
—— (2E,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H17NO3S
(2E,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[(Z)-2-chloro-2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol —— C17H12Cl2N2O3
5-[(Z)-2-chloro-2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol
—— 4-bromo-5-[(E)-2-(5-chloro-1,3-benzoxazol-2-yl)ethenyl]-2-methoxyphenol —— C16H11BrClNO3
4-bromo-5-[(E)-2-(5-chloro-1,3-benzoxazol-2-yl)ethenyl]-2-methoxyphenol
—— 2-(2-chloro-4-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H12ClFN2O5
2-(2-chloro-4-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— (E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(5-methylthiophen-2-yl)prop-2-enamide —— C15H14N2O4S
(E)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-(5-methylthiophen-2-yl)prop-2-enamide
—— 7-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-1,3-benzodioxole-5-carboxamide —— C15H11ClN2O6
7-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-1,3-benzodioxole-5-carboxamide
—— (E)-3-[5-(2-fluorophenyl)furan-2-yl]-N-[(2-hydroxy-5-nitrophenyl)methyl]prop-2-enamide —— C20H15FN2O5
(E)-3-[5-(2-fluorophenyl)furan-2-yl]-N-[(2-hydroxy-5-nitrophenyl)methyl]prop-2-enamide
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(3-morpholin-4-ylpropyl)thiourea —— C16H24N4O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(3-morpholin-4-ylpropyl)thiourea
—— 1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea —— C14H18BrN3O3S
1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea
—— 1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea —— C14H18BrN3O3S
1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea —— C14H19N3O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea —— C13H17N3O2S
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea
—— 4-bromo-5-[(Z)-[(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C16H15BrN4O2S
4-bromo-5-[(Z)-[(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— 2-methoxy-5-[(Z)-(7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraen-12-ylhydrazinylidene)methyl]phenol —— C17H16N4O2S
2-methoxy-5-[(Z)-(7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraen-12-ylhydrazinylidene)methyl]phenol
—— 4-[(4-chlorophenoxy)methyl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C22H19ClN2O4
4-[(4-chlorophenoxy)methyl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 2-(4-methoxyphenyl)ethyl 4-acetyl-1H-pyrrole-2-carboxylate —— C16H17NO4
2-(4-methoxyphenyl)ethyl 4-acetyl-1H-pyrrole-2-carboxylate
—— 2-bromo-3-[(1S)-2-(ethylamino)-1-hydroxyethyl]phenol —— C10H14BrNO2
2-bromo-3-[(1S)-2-(ethylamino)-1-hydroxyethyl]phenol
—— 4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methyl-1H-1,2,4-triazole-5-thione —— C11H12N4O2S
4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methyl-1H-1,2,4-triazole-5-thione
—— 3-cyclopropyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C13H14N4O2S
3-cyclopropyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— 3-cyclopropyl-4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C12H12N4OS
3-cyclopropyl-4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— 5-(benzenesulfonylmethyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]furan-2-carboxamide —— C20H18N2O6S
5-(benzenesulfonylmethyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]furan-2-carboxamide
—— (5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C17H13ClN2O3S
(5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C16H11ClN2O3S
(5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (2E,4E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-4-methyl-5-phenylpenta-2,4-dienamide —— C22H17N3O3S
(2E,4E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-4-methyl-5-phenylpenta-2,4-dienamide
—— (E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-thiophen-3-ylprop-2-enamide —— C17H11N3O3S2
(E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-thiophen-3-ylprop-2-enamide
—— 2-[[(5-Chloro-2-methoxyphenyl)methyl-methylamino]methyl]-4-methoxy-6-prop-2-enylphenol —— C20H24ClNO3
2-[[(5-Chloro-2-methoxyphenyl)methyl-methylamino]methyl]-4-methoxy-6-prop-2-enylphenol
—— (5-Chloro-2-methoxyphenyl)methyl-[(2-hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl]-methylazanium —— C20H25ClNO3+
(5-Chloro-2-methoxyphenyl)methyl-[(2-hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl]-methylazanium
—— 2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C20H27N3O5S
2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol
—— 2-(2-chlorophenyl)-N-(2-hydroxy-5-nitrophenyl)acetamide —— C14H11ClN2O4
2-(2-chlorophenyl)-N-(2-hydroxy-5-nitrophenyl)acetamide
—— N-(2-hydroxy-4-nitrophenyl)-2-(2-methoxyphenoxy)acetamide —— C15H14N2O6
N-(2-hydroxy-4-nitrophenyl)-2-(2-methoxyphenoxy)acetamide
—— N-(2-hydroxy-4-nitrophenyl)-2-(4-methylphenoxy)acetamide —— C15H14N2O5
N-(2-hydroxy-4-nitrophenyl)-2-(4-methylphenoxy)acetamide
—— (2S)-N-(2-hydroxy-4-nitrophenyl)oxolane-2-carboxamide —— C11H12N2O5
(2S)-N-(2-hydroxy-4-nitrophenyl)oxolane-2-carboxamide
—— [4-[(2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl]piperazin-4-ium-1-yl]-thiophen-2-ylmethanone —— C20H25N2O3S+
[4-[(2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl]piperazin-4-ium-1-yl]-thiophen-2-ylmethanone
—— 2-[[4-[(3-Fluoro-4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C23H31FN2O3+2
2-[[4-[(3-Fluoro-4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-fluorophenoxy)acetamide —— C16H14BrFN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-fluorophenoxy)acetamide
—— 3-ethyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C12H14N4O2S
3-ethyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-cyanophenoxy)acetamide —— C17H14BrN3O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-cyanophenoxy)acetamide
—— 4-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-ethyl-1H-1,2,4-triazole-5-thione —— C12H13BrN4O2S
4-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-ethyl-1H-1,2,4-triazole-5-thione
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-methoxyphenoxy)acetamide —— C17H17BrN2O5
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-methoxyphenoxy)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)sulfonylpropanamide —— C17H19NO5S
N-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)sulfonylpropanamide
—— 2-(4-bromo-2-chloro-6-methylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C16H15BrClNO4
2-(4-bromo-2-chloro-6-methylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide