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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
—— 3-[[[(3R)-1,1-dioxothiolan-3-yl]amino]methyl]benzene-1,2-diol —— C11H15NO4S
3-[[[(3R)-1,1-dioxothiolan-3-yl]amino]methyl]benzene-1,2-diol
—— 3-[[[(3S)-1,1-dioxothiolan-3-yl]amino]methyl]benzene-1,2-diol —— C11H15NO4S
3-[[[(3S)-1,1-dioxothiolan-3-yl]amino]methyl]benzene-1,2-diol
—— N-[(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-5-thiophen-2-yl-1H-pyrazole-3-carboxamide —— C17H16N4O4S
N-[(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-5-thiophen-2-yl-1H-pyrazole-3-carboxamide
—— 2-(2,5-Dimethylphenyl)imino-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C18H15N3O4S
2-(2,5-Dimethylphenyl)imino-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-methoxyethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrClN2O6S
2-methoxyethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(3-hydroxyphenyl)methylideneamino]decanamide —— C17H26N2O2
N-[(3-hydroxyphenyl)methylideneamino]decanamide
—— 2-[2-[(2,4-Dihydroxyphenyl)methylidenehydrazinylidene]-3-methyl-4-oxo-1,3-thiazolidin-5-yl]acetic acid —— C13H13N3O5S
2-[2-[(2,4-Dihydroxyphenyl)methylidenehydrazinylidene]-3-methyl-4-oxo-1,3-thiazolidin-5-yl]acetic acid
—— [Anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;nickel(2+);hydroxide —— C15H17N3NiO3S+2
[Anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;nickel(2+);hydroxide
—— 2-[(5-chloro-2-hydroxyanilino)methylidene]-5-(4-chlorophenyl)cyclohexane-1,3-dione —— C19H15Cl2NO3
2-[(5-chloro-2-hydroxyanilino)methylidene]-5-(4-chlorophenyl)cyclohexane-1,3-dione
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(4,5-dihydro-1,3-thiazol-2-ylsulfanylmethyl)-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]triazole-4-carboxamide —— C17H17N9O4S2
1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(4,5-dihydro-1,3-thiazol-2-ylsulfanylmethyl)-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]triazole-4-carboxamide
—— ethyl 2-(2,4-dichloroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H17Cl2NO5S
ethyl 2-(2,4-dichloroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— (2E,5Z)-5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-[(3-bromophenyl)imino]-1,3-thiazolidin-4-one —— C17H12Br2N2O3S
(2E,5Z)-5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-[(3-bromophenyl)imino]-1,3-thiazolidin-4-one
—— 8a-bromo-7-ethenyl-8-(3-fluoro-2-hydroxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H16BrFO3
8a-bromo-7-ethenyl-8-(3-fluoro-2-hydroxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]decanamide —— C18H28N2O3
N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]decanamide
—— N-(2,4-difluorophenyl)-2-[5-[(4-hydroxy-3-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C18H11F2N3O6S
N-(2,4-difluorophenyl)-2-[5-[(4-hydroxy-3-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 3-cyclopentyl-1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]urea —— C18H26N2O3
3-cyclopentyl-1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]urea
—— Ethyl 2-cyano-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]acetate —— C11H10N4O5
Ethyl 2-cyano-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]acetate
—— 3-(1,3-Benzodioxol-5-yl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H13NO5S2
3-(1,3-Benzodioxol-5-yl)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[3-(3-methoxyphenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol —— C17H18N2O2
2-[3-(3-methoxyphenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol
—— ethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-ethoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H29BrN2O7S
ethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-ethoxy-4-prop-2-enoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2,5-Bis(azepan-1-ium-1-ylmethyl)benzene-1,4-diol —— C20H34N2O2+2
2,5-Bis(azepan-1-ium-1-ylmethyl)benzene-1,4-diol
—— 4-Bromo-2-[2-(4-bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C23H21Br2N2O+
4-Bromo-2-[2-(4-bromophenyl)-6-(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 5-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C23H16Br2N2O3S
5-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— 4-(4-HO-3-I-5-Methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarbonitrile —— C16H14IN3O2
4-(4-HO-3-I-5-Methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarbonitrile
—— 5,7-dibromo-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H10Br2ClNO3
5,7-dibromo-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1H-indol-2-one
—— 4-[(4-Chlorophenyl)methylsulfanyl]-2,6-dinitrophenol —— C13H9ClN2O5S
4-[(4-Chlorophenyl)methylsulfanyl]-2,6-dinitrophenol
—— 5-[(2-Hydroxyphenyl)methylidene]-2-(4-methylpiperazin-4-ium-1-yl)-1,3-thiazol-4-one —— C15H18N3O2S+
5-[(2-Hydroxyphenyl)methylidene]-2-(4-methylpiperazin-4-ium-1-yl)-1,3-thiazol-4-one
—— N-[4-(2-hydroxy-5-methylphenyl)-1,3-thiazol-2-yl]dodecanamide —— C22H32N2O2S
N-[4-(2-hydroxy-5-methylphenyl)-1,3-thiazol-2-yl]dodecanamide
—— 2,3,4a,8a-Tetrachloro-6-ethenyl-5-(3-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C18H12Cl4O3
2,3,4a,8a-Tetrachloro-6-ethenyl-5-(3-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— 2-(3-chloroanilino)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H16ClN3O3
2-(3-chloroanilino)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]octanamide —— C16H24N2O3
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]octanamide
—— 4-[2-[[(2R)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,2-diol —— C14H16N2O3S
4-[2-[[(2R)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,2-diol
—— 4-[2-[[(2S)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,2-diol —— C14H16N2O3S
4-[2-[[(2S)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,2-diol
—— 4-[2-[[(2R)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,3-diol —— C14H16N2O3S
4-[2-[[(2R)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,3-diol
—— 4-[2-[[(2S)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,3-diol —— C14H16N2O3S
4-[2-[[(2S)-oxolan-2-yl]methylamino]-1,3-thiazol-4-yl]benzene-1,3-diol
—— 4-Hydroxy-3,5-dinitrophenyl benzenesulfonate 15174-03-5 C12H8N2O8S
4-Hydroxy-3,5-dinitrophenyl benzenesulfonate
—— N(3),N(5)-Bis(2,6-dimethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxamide —— C32H35N3O4
N(3),N(5)-Bis(2,6-dimethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxamide
—— 4-chloro-2-{(E)-[(2-methyl-5-nitrophenyl)imino]methyl}-6-nitrophenol —— C14H10ClN3O5
4-chloro-2-{(E)-[(2-methyl-5-nitrophenyl)imino]methyl}-6-nitrophenol
—— 4-Decyl-2-(pyridin-3-yldiazenyl)phenol —— C21H29N3O
4-Decyl-2-(pyridin-3-yldiazenyl)phenol
—— [(3-hydroxyphenyl)(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)methyl]propanedinitrile —— C14H12N4O2
[(3-hydroxyphenyl)(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)methyl]propanedinitrile
—— 6-[5-[(2-Hydroxy-5-nitrophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C16H16N2O6S2
6-[5-[(2-Hydroxy-5-nitrophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— 2-bromo-N-[(2-hydroxy-4-methoxyphenyl)methyl]-2-methylpropanamide —— C12H16BrNO3
2-bromo-N-[(2-hydroxy-4-methoxyphenyl)methyl]-2-methylpropanamide
—— 4-Chloro-2-(dimethoxymethyl)-6-nitrophenol —— C9H10ClNO5
4-Chloro-2-(dimethoxymethyl)-6-nitrophenol
—— 2-bromo-N-[(5-chloro-2-hydroxyphenyl)methyl]-N-methylacetamide —— C10H11BrClNO2
2-bromo-N-[(5-chloro-2-hydroxyphenyl)methyl]-N-methylacetamide
—— 5-(chloromethyl)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]furan-2-carboxamide —— C15H16ClNO4
5-(chloromethyl)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]furan-2-carboxamide
—— (2S)-2-bromo-N-[(5-chloro-2-hydroxyphenyl)methyl]-N-methylpropanamide —— C11H13BrClNO2
(2S)-2-bromo-N-[(5-chloro-2-hydroxyphenyl)methyl]-N-methylpropanamide
—— (2R)-2-bromo-N-[(5-chloro-2-hydroxyphenyl)methyl]-N-methylpropanamide —— C11H13BrClNO2
(2R)-2-bromo-N-[(5-chloro-2-hydroxyphenyl)methyl]-N-methylpropanamide
—— (2S)-2-chloro-N-[(2-hydroxy-4-methoxyphenyl)methyl]propanamide —— C11H14ClNO3
(2S)-2-chloro-N-[(2-hydroxy-4-methoxyphenyl)methyl]propanamide
—— (2R)-2-chloro-N-[(2-hydroxy-4-methoxyphenyl)methyl]propanamide —— C11H14ClNO3
(2R)-2-chloro-N-[(2-hydroxy-4-methoxyphenyl)methyl]propanamide
—— 2-bromo-N-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-2-methylpropanamide —— C13H18BrNO3
2-bromo-N-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-2-methylpropanamide