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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-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-ethylphenoxy)acetamide —— C18H19BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(4-ethylphenoxy)acetamide
—— [2-[1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-4-yl]oxyphenyl]-pyrrolidin-1-ylmethanone —— C26H32N2O4
[2-[1-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]piperidin-4-yl]oxyphenyl]-pyrrolidin-1-ylmethanone
—— (2S)-N-(2-hydroxy-4-nitrophenyl)-2-(3-methylphenoxy)propanamide —— C16H16N2O5
(2S)-N-(2-hydroxy-4-nitrophenyl)-2-(3-methylphenoxy)propanamide
—— 6-[(3R)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-4-one —— C20H24ClN3O2
6-[(3R)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-4-one
—— 6-[(3S)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-4-one —— C20H24ClN3O2
6-[(3S)-1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-4-one
—— (5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(2,6-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H15ClN2O3S
(5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(2,6-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 4-chloro-2-[(Z)-3-[(3R)-3,4-dimethylpiperazin-1-yl]-2-methylprop-1-enyl]phenol —— C16H23ClN2O
4-chloro-2-[(Z)-3-[(3R)-3,4-dimethylpiperazin-1-yl]-2-methylprop-1-enyl]phenol
—— 4-chloro-2-[(Z)-3-[(3S)-3,4-dimethylpiperazin-1-yl]-2-methylprop-1-enyl]phenol —— C16H23ClN2O
4-chloro-2-[(Z)-3-[(3S)-3,4-dimethylpiperazin-1-yl]-2-methylprop-1-enyl]phenol
—— (E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-thiophen-2-ylprop-2-enamide —— C17H11N3O3S2
(E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-thiophen-2-ylprop-2-enamide
—— (E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(2-methyl-1,3-thiazol-4-yl)prop-2-enamide —— C17H12N4O3S2
(E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(2-methyl-1,3-thiazol-4-yl)prop-2-enamide
—— (2E,4E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-5-phenylpenta-2,4-dienamide —— C21H15N3O3S
(2E,4E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-5-phenylpenta-2,4-dienamide
—— (E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(furan-2-yl)prop-2-enamide —— C17H11N3O4S
(E)-2-cyano-N-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(furan-2-yl)prop-2-enamide
—— 2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C24H21BrClFN2O
2-[(2S,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— 4-bromo-2-[(2S,6R)-4-(4-chlorophenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C22H17BrClFN2O
4-bromo-2-[(2S,6R)-4-(4-chlorophenyl)-2-(3-fluorophenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 2-[(2R,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol —— C24H21BrClFN2O
2-[(2R,6R)-2-(3-bromo-4-fluorophenyl)-4-(4-ethylphenyl)-1,2,5,6-tetrahydropyrimidin-6-yl]-4-chlorophenol
—— [4-[(2-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]piperazin-1-yl]-thiophen-2-ylmethanone —— C20H24N2O3S
[4-[(2-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]piperazin-1-yl]-thiophen-2-ylmethanone
—— 2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-ium-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol —— C20H28N3O5S+
2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-ium-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol
—— [4-[(2-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]piperazin-4-ium-1-yl]-thiophen-2-ylmethanone —— C20H25N2O3S+
[4-[(2-Hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]piperazin-4-ium-1-yl]-thiophen-2-ylmethanone
—— 2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-ium-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C20H28N3O5S+
2-[[4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-ium-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol
—— N-(2-hydroxy-4-nitrophenyl)-2-[(3-methylphenyl)methylsulfanyl]acetamide —— C16H16N2O4S
N-(2-hydroxy-4-nitrophenyl)-2-[(3-methylphenyl)methylsulfanyl]acetamide
—— 2-(2-chlorophenyl)-N-(2-hydroxy-4-nitrophenyl)acetamide —— C14H11ClN2O4
2-(2-chlorophenyl)-N-(2-hydroxy-4-nitrophenyl)acetamide
—— N-(2-hydroxy-4-nitrophenyl)-2-thiophen-2-ylacetamide —— C12H10N2O4S
N-(2-hydroxy-4-nitrophenyl)-2-thiophen-2-ylacetamide
—— (2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl-methyl-[[4-(methylcarbamoyl)phenyl]methyl]azanium —— C21H27N2O3+
(2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl-methyl-[[4-(methylcarbamoyl)phenyl]methyl]azanium
—— 3-cyclohexyl-N-(2-hydroxy-4-nitrophenyl)propanamide —— C15H20N2O4
3-cyclohexyl-N-(2-hydroxy-4-nitrophenyl)propanamide
—— 2-ethyl-N-(2-hydroxy-4-nitrophenyl)butanamide —— C12H16N2O4
2-ethyl-N-(2-hydroxy-4-nitrophenyl)butanamide
—— 2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-(2-methylpropyl)-3H-thieno[2,3-d]pyrimidin-4-one —— C19H20N2O3S
2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-(2-methylpropyl)-3H-thieno[2,3-d]pyrimidin-4-one
—— [4-[(2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl]piperazin-1-yl]-thiophen-2-ylmethanone —— C20H24N2O3S
[4-[(2-Hydroxy-5-methoxy-3-prop-2-enylphenyl)methyl]piperazin-1-yl]-thiophen-2-ylmethanone
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyphenoxy)acetamide —— C17H17BrN2O5
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyphenoxy)acetamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-chlorophenoxy)acetamide —— C16H14BrClN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-chlorophenoxy)acetamide
—— 2-[(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3,4-dimethylphenyl)acetamide —— C20H16BrN3O6S
2-[(5Z)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3,4-dimethylphenyl)acetamide
—— 5-[(Z)-([1]benzofuro[3,2-d]pyrimidin-4-ylhydrazinylidene)methyl]-2-methoxyphenol —— C18H14N4O3
5-[(Z)-([1]benzofuro[3,2-d]pyrimidin-4-ylhydrazinylidene)methyl]-2-methoxyphenol
—— 3-(2-cyclohexylethyl)-4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C17H22N4OS
3-(2-cyclohexylethyl)-4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— 3-O-ethyl 4-O-[2-(4-methoxyphenyl)ethyl] (4R)-2,6-dimethyl-3,4-dihydropyridine-3,4-dicarboxylate —— C20H25NO5
3-O-ethyl 4-O-[2-(4-methoxyphenyl)ethyl] (4R)-2,6-dimethyl-3,4-dihydropyridine-3,4-dicarboxylate
—— (1S,5S,7S)-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[(4-methoxyphenyl)methyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one —— C26H30N2O4
(1S,5S,7S)-7-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[(4-methoxyphenyl)methyl]-3,8-diazatricyclo[6.3.0.01,5]undecan-2-one
—— 2-methoxy-4-[(Z)-3-[[1-[2-(2-methoxyphenyl)ethyl]piperidin-4-yl]methyl-methylamino]prop-1-enyl]phenol —— C26H36N2O3
2-methoxy-4-[(Z)-3-[[1-[2-(2-methoxyphenyl)ethyl]piperidin-4-yl]methyl-methylamino]prop-1-enyl]phenol
—— 2-[1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-4-yl]-N-methylacetamide —— C18H25ClN2O2
2-[1-[(Z)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enyl]piperidin-4-yl]-N-methylacetamide
—— 2-[[4-[(3-Fluoro-4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol —— C23H31FN2O3+2
2-[[4-[(3-Fluoro-4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol
—— (Z)-2-[4-(2,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(furan-2-yl)prop-2-enenitrile —— C16H10N2O3S
(Z)-2-[4-(2,4-dihydroxyphenyl)-1,3-thiazol-2-yl]-3-(furan-2-yl)prop-2-enenitrile
—— (Z)-3-(1-benzyl-3,5-dimethylpyrazol-4-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C22H22N2O3
(Z)-3-(1-benzyl-3,5-dimethylpyrazol-4-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (Z)-1-(4-hydroxy-3-methoxyphenyl)-3-pyridin-3-ylprop-2-en-1-one —— C15H13NO3
(Z)-1-(4-hydroxy-3-methoxyphenyl)-3-pyridin-3-ylprop-2-en-1-one
—— 4-[(Z)-3-(4-hydroxy-3-methoxyphenyl)-3-oxoprop-1-enyl]-1,5-dimethylpyrrole-2-carbonitrile —— C17H16N2O3
4-[(Z)-3-(4-hydroxy-3-methoxyphenyl)-3-oxoprop-1-enyl]-1,5-dimethylpyrrole-2-carbonitrile
—— (3E)-3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]thiochromen-4-one —— C17H13BrO3S
(3E)-3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]thiochromen-4-one
—— (3E)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1,1-dioxothiochromen-4-one —— C17H13ClO5S
(3E)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1,1-dioxothiochromen-4-one
—— (Z)-3-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C19H14ClNO3S
(Z)-3-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (3E)-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one —— C17H14O3S
(3E)-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one
—— (3E)-3-[(4-hydroxy-3-nitrophenyl)methylidene]thiochromen-4-one —— C16H11NO4S
(3E)-3-[(4-hydroxy-3-nitrophenyl)methylidene]thiochromen-4-one
—— 2-methoxy-5-[(Z)-2-(6-methoxy-1,3-benzothiazol-2-yl)ethenyl]phenol —— C17H15NO3S
2-methoxy-5-[(Z)-2-(6-methoxy-1,3-benzothiazol-2-yl)ethenyl]phenol
—— methyl 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate —— C18H15ClN2O5S
methyl 2-[(E)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate
—— ethyl 2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate —— C19H18N2O5S
ethyl 2-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate
—— (3E)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,1-dioxothiochromen-4-one —— C18H16O6S
(3E)-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,1-dioxothiochromen-4-one