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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
—— 6-[(S)-(2-hydroxy-3-methoxyphenyl)-pyrrolidin-1-ium-1-ylmethyl]-1,3-benzodioxol-5-ol —— C19H22NO5+
6-[(S)-(2-hydroxy-3-methoxyphenyl)-pyrrolidin-1-ium-1-ylmethyl]-1,3-benzodioxol-5-ol
—— 6-[(R)-(2-hydroxy-3-methoxyphenyl)-pyrrolidin-1-ium-1-ylmethyl]-1,3-benzodioxol-5-ol —— C19H22NO5+
6-[(R)-(2-hydroxy-3-methoxyphenyl)-pyrrolidin-1-ium-1-ylmethyl]-1,3-benzodioxol-5-ol
—— 4-[(3S)-3-[[1-(pyridin-3-ylmethyl)piperidin-4-yl]amino]butyl]phenol —— C21H29N3O
4-[(3S)-3-[[1-(pyridin-3-ylmethyl)piperidin-4-yl]amino]butyl]phenol
—— 4-[(3R)-3-[[1-(pyridin-4-ylmethyl)piperidin-4-yl]amino]butyl]phenol —— C21H29N3O
4-[(3R)-3-[[1-(pyridin-4-ylmethyl)piperidin-4-yl]amino]butyl]phenol
—— 4-[(3S)-3-[[1-(pyridin-4-ylmethyl)piperidin-4-yl]amino]butyl]phenol —— C21H29N3O
4-[(3S)-3-[[1-(pyridin-4-ylmethyl)piperidin-4-yl]amino]butyl]phenol
—— 4-[(3R)-3-[[1-(pyridin-3-ylmethyl)piperidin-4-yl]amino]butyl]phenol —— C21H29N3O
4-[(3R)-3-[[1-(pyridin-3-ylmethyl)piperidin-4-yl]amino]butyl]phenol
—— (3S)-3-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolane-2,4-dione —— C20H18O9
(3S)-3-[(R)-(6-hydroxy-1,3-benzodioxol-5-yl)-(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolane-2,4-dione
—— 5-[(Z)-[3-[(4-chlorophenyl)methylsulfanyl]-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol —— C17H15ClN4O2S
5-[(Z)-[3-[(4-chlorophenyl)methylsulfanyl]-1,2,4-triazol-4-yl]iminomethyl]-2-methoxyphenol
—— methyl (4R)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C13H13N3O6
methyl (4R)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— methyl (4S)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C13H13N3O6
methyl (4S)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-(4-methoxyphenyl)ethyl 4-[(1S)-1-hydroxyethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate —— C18H23NO4
2-(4-methoxyphenyl)ethyl 4-[(1S)-1-hydroxyethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate
—— 3-(diethylamino)-6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]cyclohexa-2,4-dien-1-one —— C18H21N3O4
3-(diethylamino)-6-[[(2-hydroxy-5-nitrophenyl)methylamino]methylidene]cyclohexa-2,4-dien-1-one
—— (5E)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(3-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C17H16N4O2S2
(5E)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(3-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— (5Z)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H15FN2O4S
(5Z)-2-(4-fluorophenyl)imino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-5-[(3,4-dihydroxyphenyl)methylidene]-2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C16H14N4O3S2
(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-2-[(5-methyl-1,3,4-thiadiazol-2-yl)imino]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— [4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]-[(4S)-4,5,6,7-tetrahydro-1H-indazol-4-yl]methanone —— C19H21N3O2
[4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]-[(4S)-4,5,6,7-tetrahydro-1H-indazol-4-yl]methanone
—— [4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]-[(4R)-4,5,6,7-tetrahydro-1H-indazol-4-yl]methanone —— C19H21N3O2
[4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]-[(4R)-4,5,6,7-tetrahydro-1H-indazol-4-yl]methanone
—— (5Z)-5-benzylidene-3-(2-hydroxyphenyl)-2-(2-hydroxyphenyl)imino-1,3-thiazolidin-4-one —— C22H16N2O3S
(5Z)-5-benzylidene-3-(2-hydroxyphenyl)-2-(2-hydroxyphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(4-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C17H16N4O2S2
(5E)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(4-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— (5E)-5-[(3-hydroxyphenyl)methylidene]-2-[[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]imino]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C19H20N4O2S2
(5E)-5-[(3-hydroxyphenyl)methylidene]-2-[[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]imino]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— (5Z)-3-(4-ethoxyphenyl)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H14N2O5S2
(5Z)-3-(4-ethoxyphenyl)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 1-[(1R,3S)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea —— C17H26N2O2S
1-[(1R,3S)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea
—— 1-[(1S,3R)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea —— C17H26N2O2S
1-[(1S,3R)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea
—— 1-[(1R,3R)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea —— C17H26N2O2S
1-[(1R,3R)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea
—— 1-[(1S,3S)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea —— C17H26N2O2S
1-[(1S,3S)-3-ethylsulfanylcyclopentyl]-3-[2-(4-hydroxyphenyl)ethyl]-1-methylurea
—— 1-[(4-chloro-1-methylpyrrol-2-yl)methyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea —— C18H24ClN3O2
1-[(4-chloro-1-methylpyrrol-2-yl)methyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea
—— 1-[(4-chloro-1-methylpyrrol-2-yl)methyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea —— C18H24ClN3O2
1-[(4-chloro-1-methylpyrrol-2-yl)methyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-1-methylurea
—— (4S)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16ClNO5
(4S)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 2-[(2-hydroxyphenyl)methyl]-1-(2-methoxyethyl)-3-[[(2R)-oxolan-2-yl]methyl]guanidine —— C16H25N3O3
2-[(2-hydroxyphenyl)methyl]-1-(2-methoxyethyl)-3-[[(2R)-oxolan-2-yl]methyl]guanidine
—— 2-[(2-hydroxyphenyl)methyl]-1-(2-methoxyethyl)-3-[[(2S)-oxolan-2-yl]methyl]guanidine —— C16H25N3O3
2-[(2-hydroxyphenyl)methyl]-1-(2-methoxyethyl)-3-[[(2S)-oxolan-2-yl]methyl]guanidine
—— 3-[(2S)-butan-2-yl]-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]-1,2-oxazole-5-carboxamide —— C17H22N2O4
3-[(2S)-butan-2-yl]-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]-1,2-oxazole-5-carboxamide
—— (4R)-N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methyl]-6,7-dihydro-4H-thieno[3,2-c]thiopyran-4-carboxamide —— C16H16BrNO3S2
(4R)-N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methyl]-6,7-dihydro-4H-thieno[3,2-c]thiopyran-4-carboxamide
—— 3-[(2R)-butan-2-yl]-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]-1,2-oxazole-5-carboxamide —— C17H22N2O4
3-[(2R)-butan-2-yl]-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]-1,2-oxazole-5-carboxamide
—— (4S)-N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methyl]-6,7-dihydro-4H-thieno[3,2-c]thiopyran-4-carboxamide —— C16H16BrNO3S2
(4S)-N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methyl]-6,7-dihydro-4H-thieno[3,2-c]thiopyran-4-carboxamide
—— (E)-1-(4-hydroxy-3-methoxyphenyl)-3-thiophen-3-ylprop-2-en-1-one —— C14H12O3S
(E)-1-(4-hydroxy-3-methoxyphenyl)-3-thiophen-3-ylprop-2-en-1-one
—— (E)-2-(1,3-benzothiazol-2-yl)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C17H11BrN2O2S
(E)-2-(1,3-benzothiazol-2-yl)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— (Z)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile —— C15H11BrN2O2
(Z)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile
—— (1S,2S)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide —— C19H19F2NO3
(1S,2S)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide
—— (1R,2R)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide —— C19H19F2NO3
(1R,2R)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide
—— (1R,2S)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide —— C19H19F2NO3
(1R,2S)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide
—— (1S,2R)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide —— C19H19F2NO3
(1S,2R)-2-(2,6-difluorophenyl)-N-[2-(2-hydroxy-3-methoxyphenyl)ethyl]cyclopropane-1-carboxamide
—— (1S,2R,4R)-N-(furan-2-ylmethyl)-N-[(4-hydroxyphenyl)methyl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide —— C19H21NO4
(1S,2R,4R)-N-(furan-2-ylmethyl)-N-[(4-hydroxyphenyl)methyl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide
—— (1S,2S,4R)-N-(furan-2-ylmethyl)-N-[(4-hydroxyphenyl)methyl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide —— C19H21NO4
(1S,2S,4R)-N-(furan-2-ylmethyl)-N-[(4-hydroxyphenyl)methyl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide
—— [(3S)-3-(furan-2-yl)pyrrolidin-1-yl]-(3-hydroxy-4-nitrophenyl)methanone —— C15H14N2O5
[(3S)-3-(furan-2-yl)pyrrolidin-1-yl]-(3-hydroxy-4-nitrophenyl)methanone
—— [(3R)-3-(furan-2-yl)pyrrolidin-1-yl]-(3-hydroxy-4-nitrophenyl)methanone —— C15H14N2O5
[(3R)-3-(furan-2-yl)pyrrolidin-1-yl]-(3-hydroxy-4-nitrophenyl)methanone
—— (2Z)-2-{[(4-hydroxy-2-methylphenyl)amino]methylidene}cyclopentanone —— C13H15NO2
(2Z)-2-{[(4-hydroxy-2-methylphenyl)amino]methylidene}cyclopentanone
—— 1-[[(2R)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-3-ylurea —— C20H26N4O2
1-[[(2R)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-3-ylurea
—— 1-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-2-ylurea —— C20H26N4O2
1-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-2-ylurea
—— 1-[[(2R)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-2-ylurea —— C20H26N4O2
1-[[(2R)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-2-ylurea
—— 1-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-3-ylurea —— C20H26N4O2
1-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-1-[(4-hydroxyphenyl)methyl]-3-pyridin-3-ylurea