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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
—— (5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-cyclohexylimino-1,3-thiazolidin-4-one —— C16H17ClN2O3S
(5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-cyclohexylimino-1,3-thiazolidin-4-one
—— (E)-3-(2,5-dimethyl-1-propan-2-ylpyrrol-3-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C19H23NO3
(E)-3-(2,5-dimethyl-1-propan-2-ylpyrrol-3-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C17H13ClN2O3S
(5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— 4-[(E,3R)-3-hydroxybut-1-enyl]-2-methoxyphenol —— C11H14O3
4-[(E,3R)-3-hydroxybut-1-enyl]-2-methoxyphenol
—— 4-[(E,3S)-3-hydroxybut-1-enyl]-2-methoxyphenol —— C11H14O3
4-[(E,3S)-3-hydroxybut-1-enyl]-2-methoxyphenol
—— N-[(E)-[(1S)-cyclohex-3-en-1-yl]methylideneamino]-3,4,5-trihydroxybenzamide —— C14H16N2O4
N-[(E)-[(1S)-cyclohex-3-en-1-yl]methylideneamino]-3,4,5-trihydroxybenzamide
—— (5E)-2-amino-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C11H9ClN2O3S
(5E)-2-amino-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5E)-5-[(3-bromo-4,5-dihydroxyphenyl)methylidene]-2-(4-fluoroanilino)-1,3-thiazol-4-one —— C16H10BrFN2O3S
(5E)-5-[(3-bromo-4,5-dihydroxyphenyl)methylidene]-2-(4-fluoroanilino)-1,3-thiazol-4-one
—— (5E)-2-(3-chlorophenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13ClN2O3S
(5E)-2-(3-chlorophenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (1R,2S)-N-[(E)-1-(3-hydroxyphenyl)ethylideneamino]-2-phenylcyclopropane-1-carboxamide —— C18H18N2O2
(1R,2S)-N-[(E)-1-(3-hydroxyphenyl)ethylideneamino]-2-phenylcyclopropane-1-carboxamide
—— (1S,2S)-N-[(E)-1-(3-hydroxyphenyl)ethylideneamino]-2-phenylcyclopropane-1-carboxamide —— C18H18N2O2
(1S,2S)-N-[(E)-1-(3-hydroxyphenyl)ethylideneamino]-2-phenylcyclopropane-1-carboxamide
—— (5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H9ClN2O3S2
(5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-pyridin-3-yl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H10ClNO3S2
(5Z)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2E,5E)-2,5-bis[(3-chloro-4,5-dihydroxyphenyl)methylidene]cyclopentan-1-one —— C19H14Cl2O5
(2E,5E)-2,5-bis[(3-chloro-4,5-dihydroxyphenyl)methylidene]cyclopentan-1-one
—— 2-(4-methoxyphenyl)ethyl (Z)-3-[5-chloro-1-[(3S)-1,1-dioxothiolan-3-yl]-3-methylpyrazol-4-yl]prop-2-enoate —— C20H23ClN2O5S
2-(4-methoxyphenyl)ethyl (Z)-3-[5-chloro-1-[(3S)-1,1-dioxothiolan-3-yl]-3-methylpyrazol-4-yl]prop-2-enoate
—— 2-(4-methoxyphenyl)ethyl (Z)-3-[5-chloro-1-[(3R)-1,1-dioxothiolan-3-yl]-3-methylpyrazol-4-yl]prop-2-enoate —— C20H23ClN2O5S
2-(4-methoxyphenyl)ethyl (Z)-3-[5-chloro-1-[(3R)-1,1-dioxothiolan-3-yl]-3-methylpyrazol-4-yl]prop-2-enoate
—— (2S)-2-[4-[(R)-cyano-(3-hydroxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(3-hydroxyphenyl)acetonitrile —— C20H22N4O2+2
(2S)-2-[4-[(R)-cyano-(3-hydroxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(3-hydroxyphenyl)acetonitrile
—— (2S)-2-(3-hydroxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile —— C13H17N2O+
(2S)-2-(3-hydroxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile
—— (2R)-2-[4-[(S)-cyano-(3-hydroxyphenyl)methyl]piperazin-1-yl]-2-(3-hydroxyphenyl)acetonitrile —— C20H20N4O2
(2R)-2-[4-[(S)-cyano-(3-hydroxyphenyl)methyl]piperazin-1-yl]-2-(3-hydroxyphenyl)acetonitrile
—— (2S)-2-(3-hydroxyphenyl)-2-morpholin-4-ium-4-ylacetonitrile —— C12H15N2O2+
(2S)-2-(3-hydroxyphenyl)-2-morpholin-4-ium-4-ylacetonitrile
—— 2-methoxy-4-[[(3S)-3-methylmorpholin-4-yl]methyl]-6-prop-2-enylphenol —— C16H23NO3
2-methoxy-4-[[(3S)-3-methylmorpholin-4-yl]methyl]-6-prop-2-enylphenol
—— 2-methoxy-4-[[(3R)-3-methylmorpholin-4-yl]methyl]-6-prop-2-enylphenol —— C16H23NO3
2-methoxy-4-[[(3R)-3-methylmorpholin-4-yl]methyl]-6-prop-2-enylphenol
—— (4E)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-(3-bromophenyl)pyrazolidine-3,5-dione —— C16H10Br2N2O3
(4E)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-(3-bromophenyl)pyrazolidine-3,5-dione
—— 4-(4-hydroxyphenyl)-N-[(3R)-3-methyloxolan-3-yl]butanamide —— C15H21NO3
4-(4-hydroxyphenyl)-N-[(3R)-3-methyloxolan-3-yl]butanamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]furan-2-carboxamide —— C13H11BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]furan-2-carboxamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-methylbenzamide —— C16H15BrN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-methylbenzamide
—— (Z)-3-cyclopropyl-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methylbut-2-enamide —— C16H21NO2
(Z)-3-cyclopropyl-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N-methylbut-2-enamide
—— N-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3,4-dihydro-2H-pyran-5-carboxamide —— C16H21NO3
N-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3,4-dihydro-2H-pyran-5-carboxamide
—— N-[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]cyclopentene-1-carboxamide —— C15H19NO3
N-[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]cyclopentene-1-carboxamide
—— N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3,4-dihydro-2H-pyran-5-carboxamide —— C16H21NO3
N-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3,4-dihydro-2H-pyran-5-carboxamide
—— (Z)-3-cyclopropyl-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylbut-2-enamide —— C16H21NO2
(Z)-3-cyclopropyl-N-[(1S)-1-(2-hydroxyphenyl)ethyl]-N-methylbut-2-enamide
—— N-[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]cyclopentene-1-carboxamide —— C15H19NO3
N-[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]cyclopentene-1-carboxamide
—— 2-Methoxy-6-[[4-[(3-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-prop-2-enylphenol —— C23H32N2O2+2
2-Methoxy-6-[[4-[(3-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-prop-2-enylphenol
—— 2-[(4-cyclopropyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[(4-hydroxy-3,5-dimethylphenyl)methyl]acetamide —— C20H22N4O2S2
2-[(4-cyclopropyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]-N-[(4-hydroxy-3,5-dimethylphenyl)methyl]acetamide
—— 2-Bromo-6-methoxy-4-[[[4-(pyrrolidin-1-ylmethyl)phenyl]methylamino]methyl]phenol —— C20H25BrN2O2
2-Bromo-6-methoxy-4-[[[4-(pyrrolidin-1-ylmethyl)phenyl]methylamino]methyl]phenol
—— N-[(2-hydroxyphenyl)methyl]-2-(1,2-oxazol-3-yl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C17H20N2O4
N-[(2-hydroxyphenyl)methyl]-2-(1,2-oxazol-3-yl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— N-[(2-hydroxyphenyl)methyl]-2-(1,2-oxazol-3-yl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C17H20N2O4
N-[(2-hydroxyphenyl)methyl]-2-(1,2-oxazol-3-yl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— (5Z)-2-(4-ethylphenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(4-ethylphenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N-[(1R)-1-(2-ethyl-4-methyl-1,3-thiazol-5-yl)ethyl]-2-hydroxy-N-methyl-3-nitrobenzamide —— C16H19N3O4S
N-[(1R)-1-(2-ethyl-4-methyl-1,3-thiazol-5-yl)ethyl]-2-hydroxy-N-methyl-3-nitrobenzamide
—— N-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-2-hydroxy-3-nitrobenzamide —— C14H13N3O4S
N-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-2-hydroxy-3-nitrobenzamide
—— N-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-2-hydroxy-3-nitrobenzamide —— C14H13N3O4S
N-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-2-hydroxy-3-nitrobenzamide
—— N-[(1S)-1-(2-ethyl-4-methyl-1,3-thiazol-5-yl)ethyl]-2-hydroxy-N-methyl-3-nitrobenzamide —— C16H19N3O4S
N-[(1S)-1-(2-ethyl-4-methyl-1,3-thiazol-5-yl)ethyl]-2-hydroxy-N-methyl-3-nitrobenzamide
—— ethyl 1-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperidine-4-carboxylate —— C19H22N2O5S
ethyl 1-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperidine-4-carboxylate
—— 4-[(3S)-3-[[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol —— C16H23F3N2O
4-[(3S)-3-[[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol
—— 4-[(3S)-3-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol —— C16H23F3N2O
4-[(3S)-3-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol
—— 4-[(3R)-3-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol —— C16H23F3N2O
4-[(3R)-3-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol
—— 4-[(3R)-3-[[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol —— C16H23F3N2O
4-[(3R)-3-[[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]amino]butyl]phenol
—— (5E)-2-(3-bromoanilino)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H12BrClN2O3S
(5E)-2-(3-bromoanilino)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrClNO3S
(5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— (5Z)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione —— C13H7BrClNO3S
(5Z)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione