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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
—— (5E)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-pentylcyclopent-2-en-1-one —— C18H21BrO3
(5E)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-2-pentylcyclopent-2-en-1-one
—— (5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-pentylcyclopent-2-en-1-one —— C17H19NO4
(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-pentylcyclopent-2-en-1-one
—— 3-(3,5-dimethylpyrazol-1-yl)-4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C14H14N6OS
3-(3,5-dimethylpyrazol-1-yl)-4-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— [4-(2-methoxyethyl)phenyl] (3R)-2,3-dihydro-1,4-benzodioxine-3-carboxylate —— C18H18O5
[4-(2-methoxyethyl)phenyl] (3R)-2,3-dihydro-1,4-benzodioxine-3-carboxylate
—— [4-(2-Methoxyethyl)phenyl] 1-benzofuran-2-carboxylate —— C18H16O4
[4-(2-Methoxyethyl)phenyl] 1-benzofuran-2-carboxylate
—— 2-[(3R)-1,1-dioxothiolan-3-yl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C14H18N2O5S
2-[(3R)-1,1-dioxothiolan-3-yl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-[(3S)-1,1-dioxothiolan-3-yl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C14H18N2O5S
2-[(3S)-1,1-dioxothiolan-3-yl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4-propan-2-ylphenoxy)methyl]-1H-1,2,4-triazole-5-thione —— C20H22N4O3S
4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4-propan-2-ylphenoxy)methyl]-1H-1,2,4-triazole-5-thione
—— 3-[(2,4-dimethylphenoxy)methyl]-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C19H20N4O3S
3-[(2,4-dimethylphenoxy)methyl]-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— N-(5-chloro-2-methylphenyl)-2-[4-(2-methoxyethyl)phenoxy]acetamide —— C18H20ClNO3
N-(5-chloro-2-methylphenyl)-2-[4-(2-methoxyethyl)phenoxy]acetamide
—— (2E,5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-[2-(2-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C19H14N2O6S
(2E,5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-[2-(2-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— 5-[(E)-2-(5-chloro-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C16H12ClNO2S
5-[(E)-2-(5-chloro-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— (2Z,5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-[2-(2-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C20H17NO5S
(2Z,5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-[2-(2-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C21H18ClNO4S
(2Z,5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C20H16N2O5S
(2Z,5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-[2-(2-methylphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-2-(2-oxo-2-thiophen-2-ylethylidene)-1,3-thiazolidin-4-one —— C19H17NO3S2
(2Z,5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-2-(2-oxo-2-thiophen-2-ylethylidene)-1,3-thiazolidin-4-one
—— (2Z,5Z)-2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C20H16ClNO4S
(2Z,5Z)-2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-2-(2-oxo-2-thiophen-2-ylethylidene)-1,3-thiazolidin-4-one —— C18H15NO4S2
(2Z,5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-2-(2-oxo-2-thiophen-2-ylethylidene)-1,3-thiazolidin-4-one
—— (2Z,5Z)-2-[2-(4-tert-butylphenyl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C23H23NO4S
(2Z,5Z)-2-[2-(4-tert-butylphenyl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2Z,5Z)-2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H16ClNO3S
(2Z,5Z)-2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-methoxy-5-[(E)-2-(5-methyl-1,3-benzothiazol-2-yl)ethenyl]phenol —— C17H15NO2S
2-methoxy-5-[(E)-2-(5-methyl-1,3-benzothiazol-2-yl)ethenyl]phenol
—— (2Z,5Z)-2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H14ClNO4S
(2Z,5Z)-2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2Z)-2-[(5E)-5-[(3-hydroxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile —— C13H10N2O2S
(2Z)-2-[(5E)-5-[(3-hydroxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
—— (2E,5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C21H19NO6S
(2E,5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (2Z)-2-[(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile —— C13H9N3O4S
(2Z)-2-[(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
—— (2Z)-2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile —— C14H12N2O3S
(2Z)-2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
—— (2Z)-2-[(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile —— C14H11ClN2O3S
(2Z)-2-[(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
—— (2Z)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile —— C15H14N2O2S
(2Z)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
—— (2Z)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile —— C15H14N2O4S
(2Z)-2-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
—— (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-methylsulfonylprop-2-enenitrile —— C12H13NO5S
(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-methylsulfonylprop-2-enenitrile
—— (E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-methylsulfonylprop-2-enenitrile —— C11H10BrNO4S
(E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-methylsulfonylprop-2-enenitrile
—— (2Z)-2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-N-(2-methoxyphenyl)acetamide —— C21H20N2O5S
(2Z)-2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]-N-(2-methoxyphenyl)acetamide
—— (E)-3-(3-hydroxyphenyl)-2-methylsulfonylprop-2-enenitrile —— C10H9NO3S
(E)-3-(3-hydroxyphenyl)-2-methylsulfonylprop-2-enenitrile
—— (3Z)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-6-fluorothiochromen-4-one —— C17H12ClFO3S
(3Z)-3-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-6-fluorothiochromen-4-one
—— (6Z)-6-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-1-propyl-7H-pyrrolo[2,3-d]pyrimidine-2,4,5-trione —— C19H21N3O6
(6Z)-6-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-methyl-1-propyl-7H-pyrrolo[2,3-d]pyrimidine-2,4,5-trione
—— 2-(4-Methoxyphenyl)ethyl 2-(5,7-dimethyl-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate —— C19H22N4O3S
2-(4-Methoxyphenyl)ethyl 2-(5,7-dimethyl-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate
—— (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H21NO4S
(2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (10E)-10-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5-dimethyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one —— C19H18N2O3S
(10E)-10-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5-dimethyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one
—— (E)-3-(3-hydroxy-4-methoxyanilino)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C14H13N3O2S
(E)-3-(3-hydroxy-4-methoxyanilino)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
—— (E)-3-(2-hydroxy-4-methylanilino)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C14H13N3OS
(E)-3-(2-hydroxy-4-methylanilino)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
—— 3-cyclohexyl-1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]thiourea —— C19H28N2O2S
3-cyclohexyl-1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]thiourea
—— 1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]-3-prop-2-enylthiourea —— C16H22N2O2S
1-[(2-hydroxyphenyl)methyl]-1-[[(2R)-oxolan-2-yl]methyl]-3-prop-2-enylthiourea
—— 3-Benzyl-1-(furan-2-ylmethyl)-1-[(2-hydroxyphenyl)methyl]thiourea —— C20H20N2O2S
3-Benzyl-1-(furan-2-ylmethyl)-1-[(2-hydroxyphenyl)methyl]thiourea
—— 1-(Furan-2-ylmethyl)-1-[(2-hydroxyphenyl)methyl]-3-prop-2-enylthiourea —— C16H18N2O2S
1-(Furan-2-ylmethyl)-1-[(2-hydroxyphenyl)methyl]-3-prop-2-enylthiourea
—— 1-[(3R)-5-(furan-2-yl)-3-(2-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]propan-1-one —— C17H18N2O4
1-[(3R)-5-(furan-2-yl)-3-(2-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]propan-1-one
—— 1-[(3R)-3-(3-hydroxy-4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C18H18N2O3
1-[(3R)-3-(3-hydroxy-4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— 2-(2-chlorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H13ClN2O5
2-(2-chlorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-methoxyphenoxy)acetamide —— C16H16N2O6
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-methoxyphenoxy)acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(4-phenylmethoxyphenoxy)acetamide —— C22H20N2O6
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(4-phenylmethoxyphenoxy)acetamide
—— 1-(1,3-Benzodioxol-5-ylmethyl)-3-(2-hydroxy-5-nitrophenyl)thiourea —— C15H13N3O5S
1-(1,3-Benzodioxol-5-ylmethyl)-3-(2-hydroxy-5-nitrophenyl)thiourea