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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
—— (5Z)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-3-propan-2-yl-1,3-thiazolidine-2,4-dione —— C13H12ClNO3S
(5Z)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-3-propan-2-yl-1,3-thiazolidine-2,4-dione
—— (5S)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H24N3O3S+
(5S)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— ethyl (5S)-5-(4-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate —— C19H21N3O5S
ethyl (5S)-5-(4-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate
—— (4S)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18ClNO6
(4S)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16FNO5
(4S)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(3-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18FNO6
(4R)-1-(3-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16ClNO5
(4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-1-(3-chloro-4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H15ClFNO5
(4S)-1-(3-chloro-4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16FNO5
(4R)-1-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 4-[(2R,4R)-2-chloro-4,6,6-trimethyl-2-methylsulfanyl-1,3-diazinane-1,3-diium-4-yl]benzene-1,3-diol —— C14H23ClN2O2S+2
4-[(2R,4R)-2-chloro-4,6,6-trimethyl-2-methylsulfanyl-1,3-diazinane-1,3-diium-4-yl]benzene-1,3-diol
—— 4-[(2R,4R)-2-chloro-4,6,6-trimethyl-2-methylsulfanyl-1,3-diazinan-4-yl]benzene-1,3-diol —— C14H21ClN2O2S
4-[(2R,4R)-2-chloro-4,6,6-trimethyl-2-methylsulfanyl-1,3-diazinan-4-yl]benzene-1,3-diol
—— 5-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid —— C18H18N2O4S
5-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid
—— 4-[(3R)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid —— C17H16N2O4S
4-[(3R)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid
—— (2R)-2-(4-hydroxy-3-methoxyphenyl)-5,6-dimethyl-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one —— C15H16N2O3S
(2R)-2-(4-hydroxy-3-methoxyphenyl)-5,6-dimethyl-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one
—— 2-(4-Methoxyphenyl)ethyl 2-(5,6-dimethyl-1-benzofuran-3-yl)acetate —— C21H22O4
2-(4-Methoxyphenyl)ethyl 2-(5,6-dimethyl-1-benzofuran-3-yl)acetate
—— (7R)-N-(4-chlorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C20H18ClN5O3
(7R)-N-(4-chlorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 5-bromo-2-methoxy-4-[[methyl-[[(3R)-oxolan-3-yl]methyl]amino]methyl]phenol —— C14H20BrNO3
5-bromo-2-methoxy-4-[[methyl-[[(3R)-oxolan-3-yl]methyl]amino]methyl]phenol
—— 4-[[methyl-[(2S)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol —— C12H18N2O3S
4-[[methyl-[(2S)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol
—— 5-[[methyl-[(2S)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol —— C12H18N2O3S
5-[[methyl-[(2S)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol
—— 5-[[methyl-[(2R)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol —— C12H18N2O3S
5-[[methyl-[(2R)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol
—— 4-[[methyl-[(2R)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol —— C12H18N2O3S
4-[[methyl-[(2R)-1-methylsulfanylpropan-2-yl]amino]methyl]-2-nitrophenol
—— 3-[[Benzyl(oxan-4-ylmethyl)amino]methyl]-4-nitrophenol —— C20H24N2O4
3-[[Benzyl(oxan-4-ylmethyl)amino]methyl]-4-nitrophenol
—— 2-hydroxyethyl-[(1S)-1-(2-hydroxyphenyl)ethyl]azanium —— C10H16NO2+
2-hydroxyethyl-[(1S)-1-(2-hydroxyphenyl)ethyl]azanium
—— N-[(2S,6S)-2,6-dimethyloxan-4-yl]-3-hydroxy-4-nitrobenzamide —— C14H18N2O5
N-[(2S,6S)-2,6-dimethyloxan-4-yl]-3-hydroxy-4-nitrobenzamide
—— N-[(2R,6R)-2,6-dimethyloxan-4-yl]-3-hydroxy-4-nitrobenzamide —— C14H18N2O5
N-[(2R,6R)-2,6-dimethyloxan-4-yl]-3-hydroxy-4-nitrobenzamide
—— N-[(2S,6R)-2,6-dimethyloxan-4-yl]-3-hydroxy-4-nitrobenzamide —— C14H18N2O5
N-[(2S,6R)-2,6-dimethyloxan-4-yl]-3-hydroxy-4-nitrobenzamide
—— 5-[[(2S,6R)-2,6-dimethylthiomorpholin-4-yl]methyl]-2-methoxyphenol —— C14H21NO2S
5-[[(2S,6R)-2,6-dimethylthiomorpholin-4-yl]methyl]-2-methoxyphenol
—— 5-[[(2R,6R)-2,6-dimethylthiomorpholin-4-yl]methyl]-2-methoxyphenol —— C14H21NO2S
5-[[(2R,6R)-2,6-dimethylthiomorpholin-4-yl]methyl]-2-methoxyphenol
—— 5-[[(2S,6S)-2,6-dimethylthiomorpholin-4-yl]methyl]-2-methoxyphenol —— C14H21NO2S
5-[[(2S,6S)-2,6-dimethylthiomorpholin-4-yl]methyl]-2-methoxyphenol
—— 2-[2-[1-(2-hydroxyethyl)-3,3-dimethylindol-1-ium-2-yl]ethenyl]-6-methoxyphenol —— C21H24NO3+
2-[2-[1-(2-hydroxyethyl)-3,3-dimethylindol-1-ium-2-yl]ethenyl]-6-methoxyphenol
—— (4S,7S)-2-amino-7-(furan-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile —— C21H18N2O5
(4S,7S)-2-amino-7-(furan-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
—— 2-ethylsulfanylethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H21ClN2O5S
2-ethylsulfanylethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (2R)-3-benzylimino-2-(3,4-dichloro-2,5-dihydroxyphenyl)butanoate —— C19H19Cl2NO4
ethyl (2R)-3-benzylimino-2-(3,4-dichloro-2,5-dihydroxyphenyl)butanoate
—— 1-[(7R)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethanone —— C15H15BrN4O3
1-[(7R)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethanone
—— (3S)-1-(cyclohexylmethyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methyl-6-oxopiperidine-3-carboxamide —— C22H32N2O4
(3S)-1-(cyclohexylmethyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methyl-6-oxopiperidine-3-carboxamide
—— (3R)-1-(cyclohexylmethyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methyl-6-oxopiperidine-3-carboxamide —— C22H32N2O4
(3R)-1-(cyclohexylmethyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]-N-methyl-6-oxopiperidine-3-carboxamide
—— 4-[(1S)-1-hydroxy-2-[4-[4-(pyrrolidin-1-ylmethyl)thiophen-2-yl]triazol-1-yl]ethyl]phenol —— C19H22N4O2S
4-[(1S)-1-hydroxy-2-[4-[4-(pyrrolidin-1-ylmethyl)thiophen-2-yl]triazol-1-yl]ethyl]phenol
—— 4-[(1R)-1-hydroxy-2-[4-[4-(pyrrolidin-1-ylmethyl)thiophen-2-yl]triazol-1-yl]ethyl]phenol —— C19H22N4O2S
4-[(1R)-1-hydroxy-2-[4-[4-(pyrrolidin-1-ylmethyl)thiophen-2-yl]triazol-1-yl]ethyl]phenol
—— (2S)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methoxypropylimino)-4-oxo-1,3-thiazinane-5-carbonitrile —— C16H19N3O4S
(2S)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methoxypropylimino)-4-oxo-1,3-thiazinane-5-carbonitrile
—— (2R)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methoxypropylimino)-4-oxo-1,3-thiazinane-5-carbonitrile —— C16H19N3O4S
(2R)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methoxypropylimino)-4-oxo-1,3-thiazinane-5-carbonitrile
—— 2-Hydroxy-5-methoxy-3,4-dimethylbenzaldehyde —— C10H12O3
2-Hydroxy-5-methoxy-3,4-dimethylbenzaldehyde
—— (2S)-2-[4-[(S)-cyano-(4-hydroxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(4-hydroxyphenyl)acetonitrile —— C20H22N4O2+2
(2S)-2-[4-[(S)-cyano-(4-hydroxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(4-hydroxyphenyl)acetonitrile
—— 1-[(3R)-3-(2-hydroxyphenyl)-5-pyridin-3-yl-3,4-dihydropyrazol-2-yl]ethanone —— C16H15N3O2
1-[(3R)-3-(2-hydroxyphenyl)-5-pyridin-3-yl-3,4-dihydropyrazol-2-yl]ethanone
—— (2S)-2-(4-hydroxyphenoxy)propanehydrazide —— C9H12N2O3
(2S)-2-(4-hydroxyphenoxy)propanehydrazide
—— (4R)-5-acetyl-4-(2,4-dihydroxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one —— C13H14N2O4
(4R)-5-acetyl-4-(2,4-dihydroxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
—— ethyl (4R,5S,6S)-4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C15H17F3N2O5S
ethyl (4R,5S,6S)-4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— ethyl (4R,5R,6R)-6-(3,4-dihydroxyphenyl)-4-hydroxy-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C14H15F3N2O5S
ethyl (4R,5R,6R)-6-(3,4-dihydroxyphenyl)-4-hydroxy-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— ethyl (4R,5S,6R)-6-(3,4-dihydroxyphenyl)-4-hydroxy-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C14H15F3N2O5S
ethyl (4R,5S,6R)-6-(3,4-dihydroxyphenyl)-4-hydroxy-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— ethyl (4R,5S,6R)-4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C15H17F3N2O5S
ethyl (4R,5S,6R)-4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 2-methoxy-4-[[[(1R)-1-phenylethyl]amino]methyl]phenol —— C16H19NO2
2-methoxy-4-[[[(1R)-1-phenylethyl]amino]methyl]phenol