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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
—— ethyl (2Z,5S)-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 (2Z,5S)-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
—— ethyl (2Z,5R)-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 (2Z,5R)-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
—— [amino-(2-fluoro-4-hydroxyphenyl)methylidene]azanium —— C7H8FN2O+
[amino-(2-fluoro-4-hydroxyphenyl)methylidene]azanium
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H13NO2S2
(5E)-5-[(4-hydroxyphenyl)methylidene]-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(S)-(3-hydroxyphenyl)-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile —— C14H12N4O2
2-[(S)-(3-hydroxyphenyl)-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile
—— 2-[(R)-(3-hydroxyphenyl)-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile —— C14H12N4O2
2-[(R)-(3-hydroxyphenyl)-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile
—— 2-[(S)-(3-hydroxyphenyl)-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile —— C14H12N4O2
2-[(S)-(3-hydroxyphenyl)-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile
—— ethyl (2Z,5S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26BrN3O5S
ethyl (2Z,5S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[(1S,2S,5R,6R,9S)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]-2-methoxyphenol —— C19H26O4
4-[(1S,2S,5R,6R,9S)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]-2-methoxyphenol
—— 2-[(R)-(3-hydroxyphenyl)-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile —— C14H12N4O2
2-[(R)-(3-hydroxyphenyl)-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]methyl]propanedinitrile
—— Benzyl-hydroxy-dimethylazanium;2,4,6-trinitrophenol —— C15H17N4O8+
Benzyl-hydroxy-dimethylazanium;2,4,6-trinitrophenol
—— 4-[(1S,2S,5R,6S,9S)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]-2-methoxyphenol —— C19H26O4
4-[(1S,2S,5R,6S,9S)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]-2-methoxyphenol
—— ethyl (2Z,5R)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z,5R)-2-[(3-bromo-4-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26BrN3O5S
ethyl (2Z,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5S)-5-(4-chlorophenyl)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17Br2ClN2O4S
ethyl (2Z,5S)-5-(4-chlorophenyl)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-Hydroxy-3,5-dinitrobenzene-1-diazonium —— C6H3N4O5+
2-Hydroxy-3,5-dinitrobenzene-1-diazonium
—— ethyl (2Z,5R)-5-(4-chlorophenyl)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17Br2ClN2O4S
ethyl (2Z,5R)-5-(4-chlorophenyl)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (6E)-2-fluoro-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C15H14FNO2
(6E)-2-fluoro-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— (6E)-6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one —— C17H15N3O3
(6E)-6-[5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,2-dihydro-1,2,4-triazol-3-ylidene]cyclohexa-2,4-dien-1-one
—— 5-[2-[2-(3,4-dihydroxy-5-methoxyphenyl)ethenylsulfonylmethylsulfonyl]ethenyl]-3-methoxybenzene-1,2-diol —— C19H20O10S2
5-[2-[2-(3,4-dihydroxy-5-methoxyphenyl)ethenylsulfonylmethylsulfonyl]ethenyl]-3-methoxybenzene-1,2-diol
—— (S)-(4-hydroxyphenyl)(imino)methyl-lambda6-sulfanone —— C7H9NO2S
(S)-(4-hydroxyphenyl)(imino)methyl-lambda6-sulfanone
—— (2E)-5-amino-7-(5-bromo-2-hydroxyphenyl)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile —— C22H12Br2N4O3S
(2E)-5-amino-7-(5-bromo-2-hydroxyphenyl)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile
—— 2-(4-chloro-3,5-dimethylphenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H19ClN2O4
2-(4-chloro-3,5-dimethylphenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-methoxy-5-[(Z)-[(3,5,6-trichloropyridin-2-yl)hydrazinylidene]methyl]phenol —— C13H10Cl3N3O2
2-methoxy-5-[(Z)-[(3,5,6-trichloropyridin-2-yl)hydrazinylidene]methyl]phenol
—— (2Z)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide —— C22H25BrN4O5S2
(2Z)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide
—— (2Z)-N-[2-[2-[[(2Z)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide —— C22H25BrN4O5S2
(2Z)-N-[2-[2-[[(2Z)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide
—— (2E)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide —— C22H25BrN4O5S2
(2E)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide
—— (2E)-N-[2-[2-[[(2Z)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide —— C22H25BrN4O5S2
(2E)-N-[2-[2-[[(2Z)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyimino-3-phenylpropanamide
—— 3-bromo-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H13BrN2O3
3-bromo-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— (5E)-3-benzyl-2-benzylimino-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C24H18Br2N2O2S
(5E)-3-benzyl-2-benzylimino-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H14Br2N2O2S
(5Z)-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H14Br2N2O2S
(5E)-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— (E)-2-hydroxy-3,5-dinitro-N'-(2-nitrobenzylidene)benzohydrazide —— C14H9N5O8
(E)-2-hydroxy-3,5-dinitro-N'-(2-nitrobenzylidene)benzohydrazide
—— (5Z)-3-benzyl-2-benzylimino-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C24H18Br2N2O2S
(5Z)-3-benzyl-2-benzylimino-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-(4-hydroxybenzylidene)-3-(3-phenylpropyl)-2-thioxo-1,3-thiazolidin-4-one —— C19H17NO2S2
(5Z)-5-(4-hydroxybenzylidene)-3-(3-phenylpropyl)-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H15FN2O2S
(5Z)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-1-(4-bromophenyl)-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H9Br2N3O5S
(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-1-(4-bromophenyl)-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-1-(4-bromophenyl)-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H9Br2N3O5S
(5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-1-(4-bromophenyl)-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (4Z)-4-[(5-bromo-2-hydroxyphenyl)methylidene]-1-(4-chlorophenyl)pyrazolidine-3,5-dione —— C16H10BrClN2O3
(4Z)-4-[(5-bromo-2-hydroxyphenyl)methylidene]-1-(4-chlorophenyl)pyrazolidine-3,5-dione
—— N-[(Z)-(2-chloro-5-phenylfuran-3-yl)methylideneamino]-3-(2-hydroxyphenyl)propanamide —— C20H17ClN2O3
N-[(Z)-(2-chloro-5-phenylfuran-3-yl)methylideneamino]-3-(2-hydroxyphenyl)propanamide
—— methyl (4Z)-4-(2-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C14H13NO4
methyl (4Z)-4-(2-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— (1R,10R)-5-hydroxytricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one —— C13H14O2
(1R,10R)-5-hydroxytricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one
—— N'-[(3,5-dimethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C16H16N2O7
N'-[(3,5-dimethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— (5E)-3-(3,4-dichlorobenzyl)-5-(4-hydroxy-3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione —— C17H10Cl2N2O5S
(5E)-3-(3,4-dichlorobenzyl)-5-(4-hydroxy-3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione
—— (Z)-3-(4-hydroxyphenyl)-5-((1-methyl-1H-pyrrol-2-yl)methylene)-2-thioxothiazolidin-4-one —— C15H12N2O2S2
(Z)-3-(4-hydroxyphenyl)-5-((1-methyl-1H-pyrrol-2-yl)methylene)-2-thioxothiazolidin-4-one
—— 3-[(Z)-[(4-amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]phenol —— C9H10N6O
3-[(Z)-[(4-amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]phenol
—— (E)-2-(1,3-benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enenitrile —— C16H10N4O4
(E)-2-(1,3-benzoxazol-2-yl)-3-(2-hydroxy-5-nitroanilino)prop-2-enenitrile
—— 3,4,5-Trihydroxy-N'-[(Z)-(2,4,5-trimethoxyphenyl)methylidene]benzohydrazide —— C17H18N2O7
3,4,5-Trihydroxy-N'-[(Z)-(2,4,5-trimethoxyphenyl)methylidene]benzohydrazide
—— (E)-N-[(1R)-2-(cyclohexylamino)-1-(2-fluorophenyl)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide —— C30H31FN2O5S
(E)-N-[(1R)-2-(cyclohexylamino)-1-(2-fluorophenyl)-2-oxoethyl]-4-(2-hydroxy-4-methoxyphenyl)-4-oxo-N-(thiophen-2-ylmethyl)but-2-enamide
—— 5-[(E)-1-(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolan-4-one —— C20H19BrN2O4S
5-[(E)-1-(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolan-4-one