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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
—— (1R,2R)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride —— C10H11ClO4S
(1R,2R)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1S,2S)-2-(4-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1S,2S)-2-(4-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1S,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride —— C10H11ClO4S
(1S,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1R,2R)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1R,2R)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1R,2R)-2-(4-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1R,2R)-2-(4-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1S,2R)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1S,2R)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1R,2S)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1R,2S)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1S,2S)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1S,2S)-2-(3-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1S,2R)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride —— C10H11ClO4S
(1S,2R)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1R,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride —— C10H11ClO4S
(1R,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclopropane-1-sulfonyl chloride
—— (1R,2S)-2-(4-hydroxyphenyl)cyclopropane-1-sulfonyl chloride —— C9H9ClO3S
(1R,2S)-2-(4-hydroxyphenyl)cyclopropane-1-sulfonyl chloride
—— (5E)-3-[(2-chlorophenyl)methyl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C18H15ClN2O3S
(5E)-3-[(2-chlorophenyl)methyl]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (5E)-3-[(2-chlorophenyl)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C18H15ClN2O3S
(5E)-3-[(2-chlorophenyl)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— ethyl (2E,5S)-5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5S)-5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(2,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5S)-5-(2,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O6S
ethyl (2E,5S)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (1S,2R,3S,7Z,10R)-7-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C24H20N2O6S
methyl (1S,2R,3S,7Z,10R)-7-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
—— methyl (1S,2S,3S,7Z,10R)-7-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C24H20N2O6S
methyl (1S,2S,3S,7Z,10R)-7-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
—— ethyl (2E,5R)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O6S
ethyl (2E,5R)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-bromo-4-[[[(3S)-1,1-dioxothiolan-3-yl]methylamino]methyl]-6-methoxyphenol —— C13H18BrNO4S
2-bromo-4-[[[(3S)-1,1-dioxothiolan-3-yl]methylamino]methyl]-6-methoxyphenol
—— 2-methoxy-6-[[4-[(E)-3-phenylprop-2-enyl]piperazine-1,4-diium-1-yl]methyl]-4-prop-2-enylphenol —— C24H32N2O2+2
2-methoxy-6-[[4-[(E)-3-phenylprop-2-enyl]piperazine-1,4-diium-1-yl]methyl]-4-prop-2-enylphenol
—— ethyl (2E,5R)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H16Br2N2O4S2
ethyl (2E,5R)-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(1,3-benzoxazol-2-ylsulfanyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C16H13N3O5S
2-(1,3-benzoxazol-2-ylsulfanyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— ethyl (2E,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2E,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17BrN2O4S2
ethyl (2E,5S)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(3,4-dimethylphenyl)sulfanyl-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H18N2O4S
2-(3,4-dimethylphenyl)sulfanyl-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(4-chloro-2,6-dimethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C17H17ClN2O5
2-(4-chloro-2,6-dimethylphenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— ethyl (2E,5S)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl (2E,5S)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4E)-2-(4-bromophenyl)-4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methylpyrazol-3-one —— C17H13BrClN3O2
(4E)-2-(4-bromophenyl)-4-[(5-chloro-2-hydroxyanilino)methylidene]-5-methylpyrazol-3-one
—— 6-amino-5-[[4-amino-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidin-5-yl](4-hydroxy-3-methoxyphenyl)methyl]-2-(methylsulfanyl)pyrimidin-4(3H)-one —— C18H20N6O4S2
6-amino-5-[[4-amino-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidin-5-yl](4-hydroxy-3-methoxyphenyl)methyl]-2-(methylsulfanyl)pyrimidin-4(3H)-one
—— (5E)-2-(4-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C19H17ClN2O2S
(5E)-2-(4-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-chlorophenyl)imino-3-ethyl-1,3-thiazolidin-4-one —— C18H14Cl2N2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-chlorophenyl)imino-3-ethyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C17H12Cl2N2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(3-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C22H23ClN2O2S
(5E)-2-(3-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— (5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C21H19ClN2O3S
(5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(4-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C22H23ClN2O2S
(5E)-2-(4-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— (5E)-2-(4-chlorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H15ClN2O3S
(5E)-2-(4-chlorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(3-chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C17H12Cl2N2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(3-chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(2-chlorophenyl)imino-3-ethyl-1,3-thiazolidin-4-one —— C18H14Cl2N2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(2-chlorophenyl)imino-3-ethyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(2,4-difluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C17H11ClF2N2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(2,4-difluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(4-chlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H15ClN2O3S
(5E)-2-(4-chlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-ethyl-2-phenylimino-1,3-thiazolidin-4-one —— C18H15BrN2O2S
(5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-ethyl-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(4-fluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C17H12BrFN2O2S
(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(4-fluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-3-ethyl-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H17FN2O3S
(5E)-3-ethyl-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H15ClN2O3S
(5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one —— C17H12BrFN2O2S
(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(2-fluorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
—— (5E)-3-ethyl-5-[(4-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C18H16N2O2S
(5E)-3-ethyl-5-[(4-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-2-(4-ethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C20H20N2O3S
(5E)-2-(4-ethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(4-ethylphenyl)imino-5-[(3-hydroxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C19H18N2O2S
(5E)-2-(4-ethylphenyl)imino-5-[(3-hydroxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C19H17FN2O2S
(5E)-2-(2-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one