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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
—— N-[(2-hydroxyphenyl)methyl]-2-(1-methylpyrazol-4-yl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C18H23N3O3
N-[(2-hydroxyphenyl)methyl]-2-(1-methylpyrazol-4-yl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]-3-(1,3-thiazol-2-yl)propanamide —— C18H22N2O3S
N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]-3-(1,3-thiazol-2-yl)propanamide
—— N-[(2-hydroxyphenyl)methyl]-3-(1-methylpyrazol-4-yl)-N-[[(2S)-oxolan-2-yl]methyl]propanamide —— C19H25N3O3
N-[(2-hydroxyphenyl)methyl]-3-(1-methylpyrazol-4-yl)-N-[[(2S)-oxolan-2-yl]methyl]propanamide
—— 3-cyclopropyl-1-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]urea —— C18H27N3O2
3-cyclopropyl-1-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]urea
—— 3-cyclopropyl-1-[[(2R)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]urea —— C18H27N3O2
3-cyclopropyl-1-[[(2R)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]urea
—— N-ethyl-3-hydroxy-4-nitro-N-[(1R)-1-pyridin-3-ylethyl]benzamide —— C16H17N3O4
N-ethyl-3-hydroxy-4-nitro-N-[(1R)-1-pyridin-3-ylethyl]benzamide
—— 2-[[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]-6-(trifluoromethyl)pyridine-3-carbonitrile —— C16H14F3N3O2
2-[[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]-6-(trifluoromethyl)pyridine-3-carbonitrile
—— 2-[[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]-6-(trifluoromethyl)pyridine-3-carbonitrile —— C16H14F3N3O2
2-[[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]amino]-6-(trifluoromethyl)pyridine-3-carbonitrile
—— (2E,6S)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C20H19ClO3
(2E,6S)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— (2E,6R)-2-[(4-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C19H18O2
(2E,6R)-2-[(4-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— 5-[(Z)-2-chloro-2-[5-(5-methyl-3-phenyl-1,2-oxazol-4-yl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol —— C21H16ClN3O4
5-[(Z)-2-chloro-2-[5-(5-methyl-3-phenyl-1,2-oxazol-4-yl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol
—— (5E)-2-cyclopentylimino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H22N2O3S
(5E)-2-cyclopentylimino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylideneimidazolidin-4-one —— C16H13BrN2O4S
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylideneimidazolidin-4-one
—— (5Z)-3-(furan-2-ylmethyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C17H16N2O5S
(5Z)-3-(furan-2-ylmethyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 4-bromo-2-methoxy-5-[(E)-2-(4-methyl-1,3-thiazol-2-yl)ethenyl]phenol —— C13H12BrNO2S
4-bromo-2-methoxy-5-[(E)-2-(4-methyl-1,3-thiazol-2-yl)ethenyl]phenol
—— (5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H9BrN2O2S2
(5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-2-cyclopentylimino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H18N2O3S
(5E)-2-cyclopentylimino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 3-[(Z)-2-chloro-2-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)ethenyl]phenol —— C14H9ClN2O2S
3-[(Z)-2-chloro-2-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)ethenyl]phenol
—— (5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H14N2O2S2
(5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-N-methyl-1,3-thiazole-5-carboxamide —— C14H14N2O3S
2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-N-methyl-1,3-thiazole-5-carboxamide
—— 2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,3-thiazole-5-carboxylic acid —— C13H11NO4S
2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,3-thiazole-5-carboxylic acid
—— (Z)-1-(4-hydroxy-3-methoxyphenyl)-3-(2-phenylpyrimidin-5-yl)prop-2-en-1-one —— C20H16N2O3
(Z)-1-(4-hydroxy-3-methoxyphenyl)-3-(2-phenylpyrimidin-5-yl)prop-2-en-1-one
—— (5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-methyl-6,7-dihydroindazol-4-one —— C17H18N2O4
(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-methyl-6,7-dihydroindazol-4-one
—— 2-methoxy-5-[(E)-2-(4-nitrophenyl)sulfonylethenyl]phenol —— C15H13NO6S
2-methoxy-5-[(E)-2-(4-nitrophenyl)sulfonylethenyl]phenol
—— 2-methoxy-4-[(E)-2-(4-nitrophenyl)sulfonylethenyl]phenol —— C15H13NO6S
2-methoxy-4-[(E)-2-(4-nitrophenyl)sulfonylethenyl]phenol
—— 5-[(Z)-2-(5-chloro-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C16H12ClNO2S
5-[(Z)-2-(5-chloro-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— 5-[(Z)-2-[5-(2-bromophenyl)-1,3,4-oxadiazol-2-yl]-2-chloroethenyl]-2-methoxyphenol —— C17H12BrClN2O3
5-[(Z)-2-[5-(2-bromophenyl)-1,3,4-oxadiazol-2-yl]-2-chloroethenyl]-2-methoxyphenol
—— 5-[(Z)-2-chloro-2-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol —— C18H15ClN2O3
5-[(Z)-2-chloro-2-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol
—— 5-[(Z)-2-chloro-2-[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol —— C20H19ClN2O6
5-[(Z)-2-chloro-2-[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol
—— (2E,6S)-2-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-6-methylcyclohexan-1-one —— C14H15ClO3
(2E,6S)-2-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-6-methylcyclohexan-1-one
—— (2E,6R)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-6-methylcyclohexan-1-one —— C16H20O4
(2E,6R)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-6-methylcyclohexan-1-one
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-pyrrole-2-carboxamide —— C13H13N3O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-pyrrole-2-carboxamide
—— 5-[(Z)-benzimidazol-1-yliminomethyl]-4-bromo-2-methoxyphenol —— C15H12BrN3O2
5-[(Z)-benzimidazol-1-yliminomethyl]-4-bromo-2-methoxyphenol
—— 2-[(3S)-2-tert-butyloxaziridin-3-yl]phenol —— C11H15NO2
2-[(3S)-2-tert-butyloxaziridin-3-yl]phenol
—— 2-[(3R)-2-tert-butyloxaziridin-3-yl]phenol —— C11H15NO2
2-[(3R)-2-tert-butyloxaziridin-3-yl]phenol
—— (3E,5E)-6-(3,4-dihydroxyphenyl)hexa-3,5-dien-2-one —— C12H12O3
(3E,5E)-6-(3,4-dihydroxyphenyl)hexa-3,5-dien-2-one
—— (S)-chloro-(4-hydroxyphenyl)methanesulfonic acid —— C7H7ClO4S
(S)-chloro-(4-hydroxyphenyl)methanesulfonic acid
—— 4-[(3S)-3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-1,3-thiazol-2-one —— C18H14BrN3O2S
4-[(3S)-3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-1,3-thiazol-2-one
—— 4-[(3R)-3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-1,3-thiazol-2-one —— C18H14BrN3O2S
4-[(3R)-3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-1,3-thiazol-2-one
—— 2-[(2S)-pent-3-yn-2-yl]phenol —— C11H12O
2-[(2S)-pent-3-yn-2-yl]phenol
—— (1S,4S,6S,7R,9S)-4-tert-butyl-9-(4-hydroxy-3-methoxyphenyl)-12-imino-10,11-dioxatricyclo[5.3.2.01,6]dodecane-7,8,8-tricarbonitrile —— C24H26N4O4
(1S,4S,6S,7R,9S)-4-tert-butyl-9-(4-hydroxy-3-methoxyphenyl)-12-imino-10,11-dioxatricyclo[5.3.2.01,6]dodecane-7,8,8-tricarbonitrile
—— 2-[(2R)-pent-3-yn-2-yl]phenol —— C11H12O
2-[(2R)-pent-3-yn-2-yl]phenol
—— (1S,4R,6S,7R,9S)-4-tert-butyl-9-(4-hydroxy-3-methoxyphenyl)-12-imino-10,11-dioxatricyclo[5.3.2.01,6]dodecane-7,8,8-tricarbonitrile —— C24H26N4O4
(1S,4R,6S,7R,9S)-4-tert-butyl-9-(4-hydroxy-3-methoxyphenyl)-12-imino-10,11-dioxatricyclo[5.3.2.01,6]dodecane-7,8,8-tricarbonitrile
—— 2-bromo-N-[4-[(1S)-1-[[(2R)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide —— C27H37BrN2O4
2-bromo-N-[4-[(1S)-1-[[(2R)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide
—— 4-(2-aminoethyl)-5-[(2R)-2-aminopropyl]sulfanylbenzene-1,2-diol —— C11H18N2O2S
4-(2-aminoethyl)-5-[(2R)-2-aminopropyl]sulfanylbenzene-1,2-diol
—— 2-bromo-N-[4-[(1S)-1-[[(2S)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide —— C27H37BrN2O4
2-bromo-N-[4-[(1S)-1-[[(2S)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide
—— (2R,4R)-4-amino-2-(3,4-dihydroxyphenyl)-3-oxo-5-sulfanylpentanoic acid —— C11H13NO5S
(2R,4R)-4-amino-2-(3,4-dihydroxyphenyl)-3-oxo-5-sulfanylpentanoic acid
—— (2S,4R)-4-amino-2-(3,4-dihydroxyphenyl)-3-oxo-5-sulfanylpentanoic acid —— C11H13NO5S
(2S,4R)-4-amino-2-(3,4-dihydroxyphenyl)-3-oxo-5-sulfanylpentanoic acid
—— 2-bromo-N-[4-[(1R)-1-[[(2R)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide —— C27H37BrN2O4
2-bromo-N-[4-[(1R)-1-[[(2R)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide
—— (2R,3R)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C24H21NO8
(2R,3R)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide