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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
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-pentyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H19NO3S2
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-pentyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2S,5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one —— C19H19ClN2O3S
(2S,5E)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one
—— (3R)-8-chloro-3-methyl-2,3-dihydro-1,4-benzoxathiin-7-ol —— C9H9ClO2S
(3R)-8-chloro-3-methyl-2,3-dihydro-1,4-benzoxathiin-7-ol
—— (3S)-8-chloro-3-methyl-2,3-dihydro-1,4-benzoxathiin-7-ol —— C9H9ClO2S
(3S)-8-chloro-3-methyl-2,3-dihydro-1,4-benzoxathiin-7-ol
—— 5-[(2,4-Dihydroxy-3,5-diiodophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C10H5I2NO3S2
5-[(2,4-Dihydroxy-3,5-diiodophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(4-nitroanilino)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H13N3O5S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(4-nitroanilino)-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-[(3-bromophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H11BrN2O4
N-[(3-bromophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 2-(2-ethylsulfanyl-6-methylpyrimidin-4-yl)oxy-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H20N4O4S
2-(2-ethylsulfanyl-6-methylpyrimidin-4-yl)oxy-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-{(E)-[(2,5-dichlorophenyl)imino]methyl}-6-methoxyphenol 92103-43-0 C14H11Cl2NO2
2-{(E)-[(2,5-dichlorophenyl)imino]methyl}-6-methoxyphenol
—— 2,4-dihydroxybenzaldehyde 5-nitro2-pyridinylhydrazone 28058-38-0 C12H10N4O4
2,4-dihydroxybenzaldehyde 5-nitro2-pyridinylhydrazone
—— 2-Amino-5-(benzotriazol-1-ylmethyl)-3-nitrophenol —— C13H11N5O3
2-Amino-5-(benzotriazol-1-ylmethyl)-3-nitrophenol
—— 5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-[(3-methylphenyl)methyl]-1,3-thiazolidine-2,4-dione —— C20H19NO3S
5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-[(3-methylphenyl)methyl]-1,3-thiazolidine-2,4-dione
—— (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one
—— 2-amino-7-(furan-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile —— C21H18N2O5
2-amino-7-(furan-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
—— 2-Nitro-5-sulfanylbenzene-1,4-diol —— C6H5NO4S
2-Nitro-5-sulfanylbenzene-1,4-diol
—— 4-{[Ethyl(pyridin-4-ylmethyl)amino]methyl}benzene-1,2-diol —— C15H18N2O2
4-{[Ethyl(pyridin-4-ylmethyl)amino]methyl}benzene-1,2-diol
—— 2-(2-Hydroxyphenyl)-3,4,4a,5,6,7-hexahydrocyclopenta[b]pyridine-7a-carbonitrile —— C15H16N2O
2-(2-Hydroxyphenyl)-3,4,4a,5,6,7-hexahydrocyclopenta[b]pyridine-7a-carbonitrile
—— ethyl (5E)-2-(4-ethoxyanilino)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C26H27NO6S
ethyl (5E)-2-(4-ethoxyanilino)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 2-Methoxy-5-[(pyridin-3-ylmethylamino)methyl]phenol —— C14H16N2O2
2-Methoxy-5-[(pyridin-3-ylmethylamino)methyl]phenol
—— 3-(4-Hydroxyphenyl)propanimidamide —— C9H12N2O
3-(4-Hydroxyphenyl)propanimidamide
—— (Amino(3-hydroxy-4-methoxyphenyl)methyl)phosphonic acid —— C8H12NO5P
(Amino(3-hydroxy-4-methoxyphenyl)methyl)phosphonic acid
—— methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate —— C15H15NO5
methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1H-pyrrole-3-carboxylate
—— (2S)-3-benzyl-2-(4-hydroxy-3-nitrophenyl)-1,3-thiazolidin-4-one —— C16H14N2O4S
(2S)-3-benzyl-2-(4-hydroxy-3-nitrophenyl)-1,3-thiazolidin-4-one
—— (2R)-3-benzyl-2-(4-hydroxy-3-nitrophenyl)-1,3-thiazolidin-4-one —— C16H14N2O4S
(2R)-3-benzyl-2-(4-hydroxy-3-nitrophenyl)-1,3-thiazolidin-4-one
—— 5-[(5-Bromo-2-hydroxy-3-methylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H8BrNO2S2
5-[(5-Bromo-2-hydroxy-3-methylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-bromo-3-[(4-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H12BrNO3
5-bromo-3-[(4-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one
—— diethyl 4-(4-hydroxyphenyl)-6-methyl-2-methylidene-3,4-dihydro-1H-pyridine-3,5-dicarboxylate —— C19H23NO5
diethyl 4-(4-hydroxyphenyl)-6-methyl-2-methylidene-3,4-dihydro-1H-pyridine-3,5-dicarboxylate
—— 1-[4-[(3-Hydroxy-4-methoxyphenyl)methylideneamino]-5-(2-oxopropyl)-1,2,4-triazol-3-yl]propan-2-one —— C16H18N4O4
1-[4-[(3-Hydroxy-4-methoxyphenyl)methylideneamino]-5-(2-oxopropyl)-1,2,4-triazol-3-yl]propan-2-one
—— 5-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one —— C19H19ClN2O3S
5-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-ethylanilino)-1,3-thiazolidin-4-one
—— 2-fluoro-N-[[(2S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]-N-(2-morpholin-4-ylethyl)benzamide —— C26H34FN3O5
2-fluoro-N-[[(2S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]-N-(2-morpholin-4-ylethyl)benzamide
—— 2-fluoro-N-[[(2R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]-N-(2-morpholin-4-ylethyl)benzamide —— C26H34FN3O5
2-fluoro-N-[[(2R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]-N-(2-morpholin-4-ylethyl)benzamide
—— [4-[[(2R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]piperazin-1-yl]-(3,4,5-trimethoxyphenyl)methanone —— C27H37N3O7
[4-[[(2R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]piperazin-1-yl]-(3,4,5-trimethoxyphenyl)methanone
—— 2-methoxyethyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
2-methoxyethyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— [4-[[(2R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]piperazin-1-yl]-(2-methoxyphenyl)methanone —— C25H33N3O5
[4-[[(2R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]morpholin-2-yl]methyl]piperazin-1-yl]-(2-methoxyphenyl)methanone
—— 2-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-methylphenyl)acetamide —— C20H17BrN2O5S
2-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-methylphenyl)acetamide
—— N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]dodecanamide —— C20H32N2O3
N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]dodecanamide
—— 2-[3-(4-chlorophenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol —— C16H15ClN2O
2-[3-(4-chlorophenyl)-2,3-dihydro-1H-pyrazol-5-yl]-4-methylphenol
—— 2-chloro-6-(N-hydroxy-C-pentylcarbonimidoyl)phenol —— C12H16ClNO2
2-chloro-6-(N-hydroxy-C-pentylcarbonimidoyl)phenol
—— 2-[(benzylamino)methyl]-6-methoxyphenol —— C15H17NO2
2-[(benzylamino)methyl]-6-methoxyphenol
—— (2S)-N-[6-[4-[(2-hydroxy-3-methoxyphenyl)methyl]-1,4-diazepan-1-yl]pyridin-3-yl]-2-phenylbutanamide —— C28H34N4O3
(2S)-N-[6-[4-[(2-hydroxy-3-methoxyphenyl)methyl]-1,4-diazepan-1-yl]pyridin-3-yl]-2-phenylbutanamide
—— 2-Methoxy-6-[2-(2-methoxyphenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C25H26N2O4
2-Methoxy-6-[2-(2-methoxyphenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 2-Methoxy-6-[2-(2-methoxyphenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C25H27N2O4+
2-Methoxy-6-[2-(2-methoxyphenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— (2R)-N-[6-[4-[(2-hydroxy-3-methoxyphenyl)methyl]-1,4-diazepan-1-yl]pyridin-3-yl]-2-phenylbutanamide —— C28H34N4O3
(2R)-N-[6-[4-[(2-hydroxy-3-methoxyphenyl)methyl]-1,4-diazepan-1-yl]pyridin-3-yl]-2-phenylbutanamide
—— 2-[2-(4-Chlorophenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol —— C24H24ClN2O3+
2-[2-(4-Chlorophenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-6-methoxyphenol
—— 2-[2-(4-Chlorophenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol —— C24H23ClN2O3
2-[2-(4-Chlorophenyl)-6-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol
—— N-[(2S)-butan-2-yl]-2-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]methyl]-1,3-oxazole-4-carboxamide —— C21H30N4O4
N-[(2S)-butan-2-yl]-2-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]methyl]-1,3-oxazole-4-carboxamide
—— N-[(2R)-butan-2-yl]-2-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]methyl]-1,3-oxazole-4-carboxamide —— C21H30N4O4
N-[(2R)-butan-2-yl]-2-[[4-[(4-hydroxy-3-methoxyphenyl)methyl]piperazin-1-yl]methyl]-1,3-oxazole-4-carboxamide
—— 2,2,3,3,3-Pentafluoro-N-(2-hydroxy-4-nitro-phenyl)-propionamide —— C9H5F5N2O4
2,2,3,3,3-Pentafluoro-N-(2-hydroxy-4-nitro-phenyl)-propionamide
—— 2-[[[(1S,2R,3S)-2,3-dimethylcyclohexyl]amino]methyl]-4-methoxyphenol —— C16H25NO2
2-[[[(1S,2R,3S)-2,3-dimethylcyclohexyl]amino]methyl]-4-methoxyphenol