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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
—— (1R,2S,4S)-N-[2-(4-hydroxyphenyl)ethyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide —— C16H19NO2
(1R,2S,4S)-N-[2-(4-hydroxyphenyl)ethyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide
—— (1R,2R,4S)-N-[(3-hydroxyphenyl)methyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide —— C15H17NO2
(1R,2R,4S)-N-[(3-hydroxyphenyl)methyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide
—— N-(3,4-dichlorophenyl)-2-[4-(2-methoxyethyl)phenoxy]acetamide —— C17H17Cl2NO3
N-(3,4-dichlorophenyl)-2-[4-(2-methoxyethyl)phenoxy]acetamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methylphenoxy)acetamide —— C17H17BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methylphenoxy)acetamide
—— (1S,5S)-N-[(4-hydroxyphenyl)methyl]-9-oxobicyclo[3.3.1]nonane-3-carboxamide —— C17H21NO3
(1S,5S)-N-[(4-hydroxyphenyl)methyl]-9-oxobicyclo[3.3.1]nonane-3-carboxamide
—— (1R,5R)-N-[(4-hydroxyphenyl)methyl]-9-oxobicyclo[3.3.1]nonane-3-carboxamide —— C17H21NO3
(1R,5R)-N-[(4-hydroxyphenyl)methyl]-9-oxobicyclo[3.3.1]nonane-3-carboxamide
—— N-(2-hydroxy-4-nitrophenyl)-2-[(5E)-5-[(4-methylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C19H15N3O5S2
N-(2-hydroxy-4-nitrophenyl)-2-[(5E)-5-[(4-methylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— 1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-(2-methoxyphenyl)thiourea —— C16H16BrN3O3S
1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-(2-methoxyphenyl)thiourea
—— 5-[(Z)-(1H-benzimidazol-2-ylhydrazinylidene)methyl]-4-bromo-2-methoxyphenol —— C15H13BrN4O2
5-[(Z)-(1H-benzimidazol-2-ylhydrazinylidene)methyl]-4-bromo-2-methoxyphenol
—— (Z)-1-(2-hydroxy-5-nitrophenyl)-3-pyridin-4-ylprop-2-en-1-one —— C14H10N2O4
(Z)-1-(2-hydroxy-5-nitrophenyl)-3-pyridin-4-ylprop-2-en-1-one
—— (Z)-1-(2-hydroxy-5-methoxyphenyl)-3-pyridin-2-ylprop-2-en-1-one —— C15H13NO3
(Z)-1-(2-hydroxy-5-methoxyphenyl)-3-pyridin-2-ylprop-2-en-1-one
—— 3-amino-5-(4-chlorophenyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiophene-2-carboxamide —— C19H16ClN3O3S
3-amino-5-(4-chlorophenyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiophene-2-carboxamide
—— methyl (2R)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3R)-3-methylpiperazin-1-yl]propanoate —— C17H23F3N2O5
methyl (2R)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)-2-[(3R)-3-methylpiperazin-1-yl]propanoate
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]benzamide —— C19H19N5O3S
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]benzamide
—— (4R,6R)-4-(4-hydroxyphenyl)-3,6-dimethyl-4,8-dihydro-2H-pyrazolo[3,4-e][1,4]thiazepin-7-one —— C14H15N3O2S
(4R,6R)-4-(4-hydroxyphenyl)-3,6-dimethyl-4,8-dihydro-2H-pyrazolo[3,4-e][1,4]thiazepin-7-one
—— 4-chloro-2-[(5R,7S)-7-(4-fluorophenyl)-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidin-5-yl]phenol —— C16H13ClFN5O
4-chloro-2-[(5R,7S)-7-(4-fluorophenyl)-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidin-5-yl]phenol
—— (4R)-2-amino-4-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile —— C16H12N2O6
(4R)-2-amino-4-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile
—— (4S)-2-amino-4-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile —— C16H12N2O6
(4S)-2-amino-4-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile
—— 2,2,2-trifluoro-1-[(3R)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H11F3N2O2S
2,2,2-trifluoro-1-[(3R)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— 2,2,2-trifluoro-1-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C17H13F3N2O2
2,2,2-trifluoro-1-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— diethyl (2S,4R)-2,4-dicyano-3-(3,5-dibromo-2-hydroxyphenyl)pentanedioate —— C17H16Br2N2O5
diethyl (2S,4R)-2,4-dicyano-3-(3,5-dibromo-2-hydroxyphenyl)pentanedioate
—— 5-[(Z)-[(4-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H13ClN2O2
5-[(Z)-[(4-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— (5Z)-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxoimidazolidin-4-one —— C10H7N3O4S
(5Z)-5-(4-hydroxy-3-nitrobenzylidene)-2-thioxoimidazolidin-4-one
—— (2E,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C16H16N2O5S
(2E,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— (E)-2-(2,5-dichlorophenyl)sulfonyl-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C16H11Cl2NO4S
(E)-2-(2,5-dichlorophenyl)sulfonyl-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— (3E)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one —— C17H14ClNO3
(3E)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-methylindol-2-one
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(2-morpholin-4-ylethyl)thiourea —— C15H22N4O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(2-morpholin-4-ylethyl)thiourea
—— 3-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C14H12NO5S2-
3-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
—— 2-Amino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4,6-dimethylcyclopenta[b]pyridin-1-ium-3,7-dicarbonitrile —— C20H17N4O2+
2-Amino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4,6-dimethylcyclopenta[b]pyridin-1-ium-3,7-dicarbonitrile
—— 2-Methoxy-4-methyl-6-[(4-phenyl-1,2,3,6-tetrahydropyridin-1-ium-1-yl)methyl]phenol —— C20H24NO2+
2-Methoxy-4-methyl-6-[(4-phenyl-1,2,3,6-tetrahydropyridin-1-ium-1-yl)methyl]phenol
—— 2-(4-Methoxyphenyl)ethyl 5-nitrothiophene-2-carboxylate —— C14H13NO5S
2-(4-Methoxyphenyl)ethyl 5-nitrothiophene-2-carboxylate
—— [(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-[(3-methylthiophen-2-yl)methyl]azanium —— C14H18NO2S+
[(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-[(3-methylthiophen-2-yl)methyl]azanium
—— 2-(4-Methoxyphenyl)ethyl 3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate —— C20H17ClFNO4
2-(4-Methoxyphenyl)ethyl 3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate
—— [(4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]-phenylmethanone —— C19H18N2O3S
[(4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]-phenylmethanone
—— (4R)-4-(2-bromo-5-hydroxy-4-methoxyphenyl)-3-cyano-2,6-dimethyl-3,4-dihydropyridine-5-carboxamide —— C16H16BrN3O3
(4R)-4-(2-bromo-5-hydroxy-4-methoxyphenyl)-3-cyano-2,6-dimethyl-3,4-dihydropyridine-5-carboxamide
—— 2-(5-chloro-2-hydroxyphenyl)-1,3-thiazolidin-3-ium-5-carboxylate —— C10H10ClNO3S
2-(5-chloro-2-hydroxyphenyl)-1,3-thiazolidin-3-ium-5-carboxylate
—— (4S)-4-(2-bromo-5-hydroxy-4-methoxyphenyl)-3-cyano-2,6-dimethyl-3,4-dihydropyridine-5-carboxamide —— C16H16BrN3O3
(4S)-4-(2-bromo-5-hydroxy-4-methoxyphenyl)-3-cyano-2,6-dimethyl-3,4-dihydropyridine-5-carboxamide
—— prop-2-enyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H18N2O4S
prop-2-enyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (E)-1-(2-Hydroxy-5-methyl-phenyl)-3-pyridin-2-yl-propenone 5250-18-0 C15H13NO2
(E)-1-(2-Hydroxy-5-methyl-phenyl)-3-pyridin-2-yl-propenone
—— (E)-3-(5-bromofuran-2-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one —— C14H11BrO3
(E)-3-(5-bromofuran-2-yl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
—— (1R,2S,3R,4R)-3-[(3-hydroxy-4-methoxyphenyl)carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid —— C16H17NO5
(1R,2S,3R,4R)-3-[(3-hydroxy-4-methoxyphenyl)carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
—— (5Z)-3-[4-(diethylamino)phenyl]-5-[(2,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H20N2O3S2
(5Z)-3-[4-(diethylamino)phenyl]-5-[(2,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2R)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate —— C16H16NO5S2-
(2R)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-1,3-thiazolidin-4-one —— C16H11FN2O3S
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-1,3-thiazolidin-4-one
—— (2R)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C18H21NO6S2
(2R)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— (4R)-2-amino-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methyl-1,4-dihydroimidazol-3-ium-5-one —— C12H16N3O3+
(4R)-2-amino-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methyl-1,4-dihydroimidazol-3-ium-5-one
—— 6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]-3-propoxycyclohexa-2,4-dien-1-one —— C17H18N2O5
6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]-3-propoxycyclohexa-2,4-dien-1-one
—— 6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]cyclohexa-2,4-dien-1-one —— C14H12N2O4
6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]cyclohexa-2,4-dien-1-one