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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
—— (2E,5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-cyclopentyl-2-(phenylimino)-1,3-thiazolidin-4-one —— C22H21BrN2O3S
(2E,5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-cyclopentyl-2-(phenylimino)-1,3-thiazolidin-4-one
—— ethyl (2E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O4S2
ethyl (2E)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H16Br2N2O4S2
ethyl (2E)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E)-but-2-en-1-yl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C17H19ClN2O5
(2E)-but-2-en-1-yl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— (E)-ethyl 2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O5S
(E)-ethyl 2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18Br2N2O4S
ethyl (2E)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(2-Hydroxy-5-nitrophenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H12N2O4S2
5-[(2-Hydroxy-5-nitrophenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— Synephrinium —— C9H13NO2*H
Synephrinium
—— [3-(Dihydroxymethyl)-5-hydroxyphenyl]methanediol;dysprosium;dodecahydrate —— C16H44Dy3O22
[3-(Dihydroxymethyl)-5-hydroxyphenyl]methanediol;dysprosium;dodecahydrate
—— [3-(Dihydroxymethyl)-5-hydroxyphenyl]methanediol;terbium;dodecahydrate —— C16H44O22Tb3
[3-(Dihydroxymethyl)-5-hydroxyphenyl]methanediol;terbium;dodecahydrate
—— 2-Chlorophenol;2-chlorophenolate;zirconium —— C36H28Cl6O6Zr-2
2-Chlorophenol;2-chlorophenolate;zirconium
—— 6-(2-Hydroxy-4,6-dimethylphenyl)-5-methyl-1-(1-phenylethyl)-3,4-dihydropyridin-2-one —— C22H25NO2
6-(2-Hydroxy-4,6-dimethylphenyl)-5-methyl-1-(1-phenylethyl)-3,4-dihydropyridin-2-one
—— 4-[2-Hydroxy-3-[3-(2-methoxyphenoxy)propylamino]propoxy]-2,3,6-trimethylphenol —— C22H31NO5
4-[2-Hydroxy-3-[3-(2-methoxyphenoxy)propylamino]propoxy]-2,3,6-trimethylphenol
—— 2-[2-(3-Bromo-4-fluorophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C23H20BrClFN2O2+
2-[2-(3-Bromo-4-fluorophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— N-[(3-chlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H11ClN2O4
N-[(3-chlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19ClO3
8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— Aminobenzene, N-trifluoroacetyl-2-hydroxy-3,5-dinitro- —— C8H4F3N3O6
Aminobenzene, N-trifluoroacetyl-2-hydroxy-3,5-dinitro-
—— 2-Methoxy-4-(oxan-4-yliminomethyl)phenol —— C13H17NO3
2-Methoxy-4-(oxan-4-yliminomethyl)phenol
—— 3-(3-Hydroxy-4-methoxyphenyl)-2-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]prop-2-enenitrile —— C19H13N3O4S
3-(3-Hydroxy-4-methoxyphenyl)-2-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]prop-2-enenitrile
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-5-[(N-methylanilino)methyl]triazole-4-carboxamide —— C22H23N9O5
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-5-[(N-methylanilino)methyl]triazole-4-carboxamide
—— 2-[2,6-Bis(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-bromophenol —— C22H17BrCl2N2O
2-[2,6-Bis(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-4-bromophenol
—— 3-Benzyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H11Br2NO2S2
3-Benzyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-(4-ethoxyphenyl)-N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide —— C20H23N3O5
N-(4-ethoxyphenyl)-N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide
—— Methyl 4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-prop-2-enylpyrrole-3-carboxylate —— C17H17NO4
Methyl 4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-prop-2-enylpyrrole-3-carboxylate
—— 8a-bromo-7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H16BrF3O4
8a-bromo-7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 5-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-ethyl-1,3-thiazolidine-2,4-dione —— C12H9BrClNO3S
5-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-ethyl-1,3-thiazolidine-2,4-dione
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO3S2
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-methoxyethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
2-methoxyethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one —— C21H22N2O5S
5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
—— Ethyl 2-hydrazinyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate —— C15H20N4O4
Ethyl 2-hydrazinyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate
—— 2-(1-ethylbenzimidazol-2-yl)sulfanyl-N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]acetohydrazide —— C20H22N4O3S
2-(1-ethylbenzimidazol-2-yl)sulfanyl-N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]acetohydrazide
—— 3-Benzyl-2-benzylimino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C25H22N2O3S
3-Benzyl-2-benzylimino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-(4-Hydroxyphenyl)imino-5-(2-methyl-3-phenylprop-2-enylidene)-3-prop-2-enyl-1,3-thiazolidin-4-one —— C22H20N2O2S
2-(4-Hydroxyphenyl)imino-5-(2-methyl-3-phenylprop-2-enylidene)-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 3-Cyclopentyl-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C22H20Br2N2O3S
3-Cyclopentyl-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— 2-[5-(6-Methylpyridin-3-yl)-1,3-oxazolidin-3-ium-2-yl]phenol —— C15H17N2O2+
2-[5-(6-Methylpyridin-3-yl)-1,3-oxazolidin-3-ium-2-yl]phenol
—— ethyl 2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H16BrClN2O4S2
ethyl 2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 7-Ethyl-2-(3-hydroxy-4-methoxyphenyl)-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol —— C18H21N3O3S
7-Ethyl-2-(3-hydroxy-4-methoxyphenyl)-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol
—— ethyl 5-(2-ethoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H32N2O7S
ethyl 5-(2-ethoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(4-Hydroxy-3,5-dimethylphenyl)-6,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C24H23N3O5
2-(4-Hydroxy-3,5-dimethylphenyl)-6,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— 2-[5-[(2,6-dichlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C18H11Cl2N3O5S2
2-[5-[(2,6-dichlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide
—— 1-ethyl-5-[(1-ethyl-6-hydroxy-2-methylsulfanyl-4-oxopyrimidin-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]-6-hydroxy-2-methylsulfanylpyrimidin-4-one —— C22H26N4O6S2
1-ethyl-5-[(1-ethyl-6-hydroxy-2-methylsulfanyl-4-oxopyrimidin-5-yl)-(3-hydroxy-4-methoxyphenyl)methyl]-6-hydroxy-2-methylsulfanylpyrimidin-4-one
—— 2-[2-(Benzylidenehydrazinylidene)-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate —— C18H14N3O4S-
2-[2-(Benzylidenehydrazinylidene)-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate
—— 2-[(2-hydroxy-4-nitroanilino)methylidene]-3-methyl-1-oxopyrido[1,2-a]benzimidazole-4-carbonitrile —— C20H13N5O4
2-[(2-hydroxy-4-nitroanilino)methylidene]-3-methyl-1-oxopyrido[1,2-a]benzimidazole-4-carbonitrile
—— 2-Methoxy-6-{[(5-methyl-1,2-oxazol-3-yl)amino]methyl}phenol —— C12H14N2O3
2-Methoxy-6-{[(5-methyl-1,2-oxazol-3-yl)amino]methyl}phenol
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(piperidin-1-ium-1-ylmethyl)-1,3-thiazolidine-2,4-dione —— C17H21N2O4S+
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(piperidin-1-ium-1-ylmethyl)-1,3-thiazolidine-2,4-dione
—— methyl (1R,2R,3S)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3-methyl-2,3-dihydro-1H-indene-2-carboxylate —— C20H22O6
methyl (1R,2R,3S)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3-methyl-2,3-dihydro-1H-indene-2-carboxylate
—— 5-(3-methoxy-4-hydroxy-5-bromo-benzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione —— C14H15BrO6
5-(3-methoxy-4-hydroxy-5-bromo-benzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 5-[1-Hydroxy-2-(2-methylbutan-2-ylamino)ethyl]benzene-1,3-diol;hydrobromide —— C13H22BrNO3
5-[1-Hydroxy-2-(2-methylbutan-2-ylamino)ethyl]benzene-1,3-diol;hydrobromide
—— Bis(2-hydroxyphenyl) telluride 152943-38-9 C12H10O2Te
Bis(2-hydroxyphenyl) telluride