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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-(5-Chloro-2-hydroxyphenyl)imino-5-[3-(furan-2-yl)prop-2-enylidene]-1,3-thiazolidin-4-one —— C16H11ClN2O3S
2-(5-Chloro-2-hydroxyphenyl)imino-5-[3-(furan-2-yl)prop-2-enylidene]-1,3-thiazolidin-4-one
—— 3-(4-Hydroxyphenyl)-5-[3-(4-hydroxyphenyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H10N2O4S4
3-(4-Hydroxyphenyl)-5-[3-(4-hydroxyphenyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-(3-Hydroxyphenyl)-5-[3-(3-hydroxyphenyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H10N2O4S4
3-(3-Hydroxyphenyl)-5-[3-(3-hydroxyphenyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-(3-hydroxyphenyl)-5-(1H-pyrrol-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H10N2O2S2
3-(3-hydroxyphenyl)-5-(1H-pyrrol-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(5-Chloro-2-hydroxyphenyl)imino-5-[(1-methylpyrrol-2-yl)methylidene]-1,3-thiazolidin-4-one —— C15H12ClN3O2S
2-(5-Chloro-2-hydroxyphenyl)imino-5-[(1-methylpyrrol-2-yl)methylidene]-1,3-thiazolidin-4-one
—— 2-[(5-chloro-2-hydroxyphenyl)amino]-1,3-thiazol-4(5H)-one —— C9H7ClN2O2S
2-[(5-chloro-2-hydroxyphenyl)amino]-1,3-thiazol-4(5H)-one
—— 2-(4-Ethoxyphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O4S
2-(4-Ethoxyphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-(3,4-Dichlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H12Cl2N2O3S
2-(3,4-Dichlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-(2,5-Dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
2-(2,5-Dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[4-(Diethylamino)phenyl]imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C21H23N3O3S
2-[4-(Diethylamino)phenyl]imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[2-Chloro-5-(trifluoromethyl)phenyl]imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H12ClF3N2O3S
2-[2-Chloro-5-(trifluoromethyl)phenyl]imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(4-ethoxyphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O4S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(4-ethoxyphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C17H14N2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one
—— 2-(3-Chloro-4-fluorophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H10ClFN2O3S
2-(3-Chloro-4-fluorophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-(4-Butylphenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H20N2O3S
2-(4-Butylphenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(3,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 2-(2-Fluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13FN2O3S
2-(2-Fluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2,4-dimethylbenzamide —— C20H18N2O4S2
N-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2,4-dimethylbenzamide
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-1,3-thiazolidin-4-one —— C16H11FN2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-1,3-thiazolidin-4-one
—— 2-(2-Chlorophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H11ClN2O3S
2-(2-Chlorophenyl)imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylphenyl)-1,3-thiazolidine-2,4-dione —— C18H15NO4S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylphenyl)-1,3-thiazolidine-2,4-dione
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-ethoxyphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O4S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-ethoxyphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-ethylphenyl)imino-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2,5-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2,5-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— N-(2-hydroxy-4-nitrophenyl)-2-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C21H17N3O5S2
N-(2-hydroxy-4-nitrophenyl)-2-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— N-(2-hydroxy-4-nitrophenyl)-4-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C23H21N3O5S2
N-(2-hydroxy-4-nitrophenyl)-4-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— N-(2-hydroxy-5-nitrophenyl)-2-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C21H17N3O5S2
N-(2-hydroxy-5-nitrophenyl)-2-[5-(2-methyl-3-phenylprop-2-enylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— 4-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-5-nitrophenyl)butanamide —— C22H19N3O5S2
4-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-5-nitrophenyl)butanamide
—— 4-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-4-nitrophenyl)butanamide —— C22H19N3O5S2
4-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-4-nitrophenyl)butanamide
—— 2-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-5-nitrophenyl)acetamide —— C20H15N3O5S2
2-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-5-nitrophenyl)acetamide
—— 2-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-4-nitrophenyl)acetamide —— C20H15N3O5S2
2-(5-cinnamylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-4-nitrophenyl)acetamide
—— 4-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)butanamide —— C18H15N3O6S2
4-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)butanamide
—— 6-[5-[(4-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide —— C22H20ClN3O5S2
6-[5-[(4-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide
—— 6-[5-[(4-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide —— C22H20ClN3O5S2
6-[5-[(4-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide
—— 6-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide —— C23H21N3O7S2
6-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide
—— 6-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide —— C23H21N3O7S2
6-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide
—— 6-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide —— C24H25N3O7S2
6-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)hexanamide
—— N-(2-hydroxy-4-nitrophenyl)-6-[5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide —— C23H23N3O6S2
N-(2-hydroxy-4-nitrophenyl)-6-[5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide
—— N-(2-hydroxy-5-nitrophenyl)-6-[5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide —— C23H23N3O6S2
N-(2-hydroxy-5-nitrophenyl)-6-[5-[(4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide
—— 6-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide —— C24H25N3O7S2
6-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)hexanamide
—— 6-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-5-nitrophenyl)hexanamide —— C22H21N3O5S2
6-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-5-nitrophenyl)hexanamide
—— 6-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-4-nitrophenyl)hexanamide —— C22H21N3O5S2
6-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-(2-hydroxy-4-nitrophenyl)hexanamide
—— N-(2-hydroxy-4-nitrophenyl)-6-[5-[(4-methylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide —— C23H23N3O5S2
N-(2-hydroxy-4-nitrophenyl)-6-[5-[(4-methylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide
—— 4-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)butanamide —— C21H17N3O7S2
4-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)butanamide
—— 4-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)butanamide —— C22H21N3O7S2
4-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)butanamide
—— 4-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)butanamide —— C22H21N3O7S2
4-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)butanamide
—— 2-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C20H17N3O7S2
2-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide
—— 2-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)acetamide —— C20H17N3O7S2
2-[5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)acetamide