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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
—— 2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-thiophen-2-ylprop-2-enamide —— C14H9N3O4S
2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-thiophen-2-ylprop-2-enamide
—— 5-[(E)-2-chloro-2-(6-nitro-1H-benzimidazol-2-yl)ethenyl]-2-methoxyphenol —— C16H12ClN3O4
5-[(E)-2-chloro-2-(6-nitro-1H-benzimidazol-2-yl)ethenyl]-2-methoxyphenol
—— 2-(3,4-Dihydroxyphenyl)-5,7-di(propan-2-yl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C20H30N2O3+2
2-(3,4-Dihydroxyphenyl)-5,7-di(propan-2-yl)-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 2-[5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3-chloro-4-methylphenyl)acetamide —— C20H16BrClN2O5S
2-[5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3-chloro-4-methylphenyl)acetamide
—— 4-(4-Hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamide —— C16H19N3O4
4-(4-Hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamide
—— 2-[[3-(3-carboxypropyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl]-4-nitrophenolate —— C14H11N2O6S2-
2-[[3-(3-carboxypropyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl]-4-nitrophenolate
—— Methyl 4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(oxolan-2-ylmethyl)pyrrole-3-carboxylate —— C19H21NO5
Methyl 4-[(4-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(oxolan-2-ylmethyl)pyrrole-3-carboxylate
—— 5-[(3-Bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one —— C26H22BrClN2O2S
5-[(3-Bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one
—— 2-[5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-3-(4-propan-2-ylphenyl)-1,3-thiazolidin-2-ylidene]propanedinitrile —— C23H18BrN3O3S
2-[5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-3-(4-propan-2-ylphenyl)-1,3-thiazolidin-2-ylidene]propanedinitrile
—— 5-[[(4,6-Dimorpholin-4-yl-1,3,5-triazin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C19H25N7O4
5-[[(4,6-Dimorpholin-4-yl-1,3,5-triazin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— ethyl (2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)propanoate —— C12H16O5
ethyl (2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)propanoate
—— ethyl (2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)propanoate —— C12H16O5
ethyl (2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)propanoate
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-cyclopentylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H20BrNO3S2
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2-cyclopentylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— methyl (2S)-2-hydroxy-2-(3-hydroxyphenyl)acetate —— C9H10O4
methyl (2S)-2-hydroxy-2-(3-hydroxyphenyl)acetate
—— (2R)-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methyloxane-2-carboxamide —— C15H21NO3
(2R)-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methyloxane-2-carboxamide
—— (2S)-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methyloxane-2-carboxamide —— C15H21NO3
(2S)-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methyloxane-2-carboxamide
—— (2R)-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methyloxane-2-carboxamide —— C15H21NO3
(2R)-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methyloxane-2-carboxamide
—— ethyl N-[(2-hydroxy-5-nitrophenyl)carbamothioyl]carbamate —— C10H11N3O5S
ethyl N-[(2-hydroxy-5-nitrophenyl)carbamothioyl]carbamate
—— propan-2-yl 2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20Cl2N2O4S
propan-2-yl 2-[(5-chloro-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-3-oxopropanoic acid —— C11H13NO4
3-[[(1R)-1-(3-hydroxyphenyl)ethyl]amino]-3-oxopropanoic acid
—— 3-[[(2S)-4-(4-hydroxyphenyl)butan-2-yl]amino]-3-oxopropanoic acid —— C13H17NO4
3-[[(2S)-4-(4-hydroxyphenyl)butan-2-yl]amino]-3-oxopropanoic acid
—— 3-[[(1S)-1-(3-hydroxyphenyl)ethyl]amino]-3-oxopropanoic acid —— C11H13NO4
3-[[(1S)-1-(3-hydroxyphenyl)ethyl]amino]-3-oxopropanoic acid
—— 2-(Ethylsulfanyl)ethyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C17H21ClN2O5S
2-(Ethylsulfanyl)ethyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 2-[(1S)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methylphenol —— C15H25NO
2-[(1S)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methylphenol
—— 2-[[[(2S)-hexan-2-yl]amino]methyl]-5-methoxyphenol —— C14H23NO2
2-[[[(2S)-hexan-2-yl]amino]methyl]-5-methoxyphenol
—— 2-[(1S)-1-[[(2S)-hexan-2-yl]amino]ethyl]-4-methylphenol —— C15H25NO
2-[(1S)-1-[[(2S)-hexan-2-yl]amino]ethyl]-4-methylphenol
—— 2-[(1R)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methylphenol —— C15H25NO
2-[(1R)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methylphenol
—— 2-[(1S)-1-[[(2S)-hexan-2-yl]amino]ethyl]-4-methoxyphenol —— C15H25NO2
2-[(1S)-1-[[(2S)-hexan-2-yl]amino]ethyl]-4-methoxyphenol
—— 2-[(1R)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methoxyphenol —— C15H25NO2
2-[(1R)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methoxyphenol
—— 2-bromo-4-[[[(2S)-hexan-2-yl]amino]methyl]-6-methoxyphenol —— C14H22BrNO2
2-bromo-4-[[[(2S)-hexan-2-yl]amino]methyl]-6-methoxyphenol
—— 2-[[[(2R)-hexan-2-yl]amino]methyl]-5-methoxyphenol —— C14H23NO2
2-[[[(2R)-hexan-2-yl]amino]methyl]-5-methoxyphenol
—— 4-[(1R)-1-[[(2R)-hexan-2-yl]amino]ethyl]benzene-1,3-diol —— C14H23NO2
4-[(1R)-1-[[(2R)-hexan-2-yl]amino]ethyl]benzene-1,3-diol
—— 2-[(1S)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methoxyphenol —— C15H25NO2
2-[(1S)-1-[[(2R)-hexan-2-yl]amino]ethyl]-4-methoxyphenol
—— 4-[(1R)-1-[[(2S)-hexan-2-yl]amino]ethyl]benzene-1,3-diol —— C14H23NO2
4-[(1R)-1-[[(2S)-hexan-2-yl]amino]ethyl]benzene-1,3-diol
—— 4-[(1S)-1-[[(2S)-hexan-2-yl]amino]ethyl]benzene-1,3-diol —— C14H23NO2
4-[(1S)-1-[[(2S)-hexan-2-yl]amino]ethyl]benzene-1,3-diol
—— (5Z)-5-[(4-hydroxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO2S2
(5Z)-5-[(4-hydroxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2,2,2-Trifluoro-1-[2-hydroxy-3-[(4-hydroxyphenyl)methylidene]cyclopenten-1-yl]ethanone —— C14H11F3O3
2,2,2-Trifluoro-1-[2-hydroxy-3-[(4-hydroxyphenyl)methylidene]cyclopenten-1-yl]ethanone
—— propan-2-yl 5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20ClN3O6S
propan-2-yl 5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[3-(4-Hydroxy-2-methylphenyl)-2,2-dioxo-1,2lambda6-benzoxathiol-3-yl]-3-methylphenol —— C21H18O5S
4-[3-(4-Hydroxy-2-methylphenyl)-2,2-dioxo-1,2lambda6-benzoxathiol-3-yl]-3-methylphenol
—— ethyl 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 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
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO3S2
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H18BrNO3S2
(5Z)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-phenylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-Cyclohexyl-1-ethyl-1-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]thiourea —— C17H26N2O2S
3-Cyclohexyl-1-ethyl-1-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]thiourea
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]dodecanamide —— C20H32N2O3
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]dodecanamide
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-nitrophenyl)acetamide —— C16H15N3O5
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-nitrophenyl)acetamide
—— 2-((2,5-Dimethoxy-benzylidene)-amino)-5-nitro-phenol —— C15H14N2O5
2-((2,5-Dimethoxy-benzylidene)-amino)-5-nitro-phenol
—— N,N'-bis[(3-hydroxy-4-methoxyphenyl)methylideneamino]oxamide —— C18H18N4O6
N,N'-bis[(3-hydroxy-4-methoxyphenyl)methylideneamino]oxamide
—— 6-[2-(2-hydroxy-5-methylphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione —— C13H11N3O5
6-[2-(2-hydroxy-5-methylphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione
—— 2-(4-Fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H15FN2O2S
2-(4-Fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 3-[5-[(1S)-1-(methylamino)ethyl]-1,3,4-oxadiazol-2-yl]phenol —— C11H13N3O2
3-[5-[(1S)-1-(methylamino)ethyl]-1,3,4-oxadiazol-2-yl]phenol