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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-hydroxyphenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H15NO3S2
(5Z)-5-[(3-hydroxyphenyl)methylidene]-3-[[(2S)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (4R)-4-(2-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C20H21N3O4S
(4R)-4-(2-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 2-(4-cyanophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C16H14N2O4
2-(4-cyanophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(2,4-dichlorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H13Cl2NO3
2-(2,4-dichlorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(4-bromo-2-methylphenyl)sulfanyl-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C16H16BrNO3S
2-(4-bromo-2-methylphenyl)sulfanyl-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-2-[2-(3-methylanilino)-2-oxoethyl]sulfanylacetamide —— C18H20N2O4S
N-(3-hydroxy-4-methoxyphenyl)-2-[2-(3-methylanilino)-2-oxoethyl]sulfanylacetamide
—— 2-[(Z)-2-(4-chloroanilino)-1-nitroethenyl]benzene-1,4-diol —— C14H11ClN2O4
2-[(Z)-2-(4-chloroanilino)-1-nitroethenyl]benzene-1,4-diol
—— 2-(1-ethylpiperidin-4-yl)-N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]acetamide —— C17H26N2O3
2-(1-ethylpiperidin-4-yl)-N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]acetamide
—— 2-(1-ethylpiperidin-4-yl)-N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]acetamide —— C17H26N2O3
2-(1-ethylpiperidin-4-yl)-N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]acetamide
—— 5-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate —— C20H19N2O4-
5-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate
—— 4-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate —— C19H17N2O4-
4-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate
—— 4-Methoxy-2-[[4-[(4-methylsulfanylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H28N2O2S+2
4-Methoxy-2-[[4-[(4-methylsulfanylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 5-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid —— C19H20N2O5S
5-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid
—— 4-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid —— C19H18N2O4
4-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid
—— 5-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate —— C19H19N2O5S-
5-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate
—— (4R)-N-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C19H18FN3O3S
(4R)-N-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— (4S)-N-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C19H18FN3O3S
(4S)-N-(4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— (4S)-N-(3,5-dimethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C21H23N3O3S
(4S)-N-(3,5-dimethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 2-[(2S,6S)-4-phenyl-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol —— C19H23N2O+
2-[(2S,6S)-4-phenyl-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol
—— 2-[(2R,6S)-4-phenyl-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol —— C19H23N2O+
2-[(2R,6S)-4-phenyl-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol
—— 2-[(2R,6S)-4-phenyl-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol —— C20H19N2OS+
2-[(2R,6S)-4-phenyl-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol
—— 2-[(2S,6S)-4-phenyl-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol —— C20H19N2OS+
2-[(2S,6S)-4-phenyl-2-thiophen-2-yl-1,2,5,6-tetrahydropyrimidin-1-ium-6-yl]phenol
—— 4-Methoxy-2-[[4-[(2-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H28N2O3+2
4-Methoxy-2-[[4-[(2-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 4-[[4-[[(1S)-cyclohex-3-en-1-yl]methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H32N2O3+2
4-[[4-[[(1S)-cyclohex-3-en-1-yl]methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— methyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C14H15N5O4
methyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— 3-[(5-Chloro-2-hydroxyphenyl)amino]-6-methyl-1,2,4-triazin-5-ol —— C10H9ClN4O2
3-[(5-Chloro-2-hydroxyphenyl)amino]-6-methyl-1,2,4-triazin-5-ol
—— 3-[(4-Hydroxy-2-methylphenyl)amino]-6-methyl-1,2,4-triazin-5-ol —— C11H12N4O2
3-[(4-Hydroxy-2-methylphenyl)amino]-6-methyl-1,2,4-triazin-5-ol
—— pentyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H21N3O6
pentyl (4R)-4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (3-Bromo-4-hydroxy-5-methoxyphenyl)methyl-(2-hydroxyethyl)-propylazanium —— C13H21BrNO3+
(3-Bromo-4-hydroxy-5-methoxyphenyl)methyl-(2-hydroxyethyl)-propylazanium
—— 2-[(4-Benzylpiperazine-1,4-diium-1-yl)methyl]-4-bromo-6-methoxyphenol —— C19H25BrN2O2+2
2-[(4-Benzylpiperazine-1,4-diium-1-yl)methyl]-4-bromo-6-methoxyphenol
—— Ethyl 4-[(4-hydroxy-3-methoxyphenyl)methyl]piperazin-4-ium-1-carboxylate —— C15H23N2O4+
Ethyl 4-[(4-hydroxy-3-methoxyphenyl)methyl]piperazin-4-ium-1-carboxylate
—— N-ethyl-2-(1-ethylpiperidin-4-yl)-N-[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]acetamide —— C19H30N2O3
N-ethyl-2-(1-ethylpiperidin-4-yl)-N-[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]acetamide
—— N-ethyl-2-(1-ethylpiperidin-4-yl)-N-[(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]acetamide —— C19H30N2O3
N-ethyl-2-(1-ethylpiperidin-4-yl)-N-[(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]acetamide
—— 2-(5-Bromo-2-hydroxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C20H31BrN2O2+2
2-(5-Bromo-2-hydroxyphenyl)-5,7-dipropyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide —— C18H28N2O3
N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide
—— N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide —— C18H28N2O3
N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide
—— N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propylpiperidin-4-yl)acetamide —— C18H28N2O3
N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propylpiperidin-4-yl)acetamide
—— N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propylpiperidin-4-yl)acetamide —— C18H28N2O3
N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(1-propylpiperidin-4-yl)acetamide
—— ethyl (5R)-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C17H17ClN2O5S
ethyl (5R)-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4R)-1-(3,5-dimethylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C23H23NO6
(4R)-1-(3,5-dimethylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 2-(Dimethylazaniumyl)ethyl-[(3-hydroxy-4-methoxyphenyl)methyl]-methylazanium —— C13H24N2O2+2
2-(Dimethylazaniumyl)ethyl-[(3-hydroxy-4-methoxyphenyl)methyl]-methylazanium
—— (4S)-1-(3,5-dimethylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C23H23NO6
(4S)-1-(3,5-dimethylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-methylphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C22H21NO6
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-methylphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(4-ethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C22H21NO5
(4R)-1-(4-ethylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-1-(4-ethylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C23H23NO6
(4S)-1-(4-ethylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— [(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone —— C19H16N2O3S2
[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-thiophen-2-ylmethanone
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]propan-1-one —— C17H18N2O3S
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]propan-1-one
—— N-ethyl-N-[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide —— C20H32N2O3
N-ethyl-N-[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide
—— N-ethyl-N-[(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide —— C20H32N2O3
N-ethyl-N-[(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-2-(1-propan-2-ylpiperidin-4-yl)acetamide
—— (2E,5E)-5-benzylidene-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one —— C23H17N3O2S
(2E,5E)-5-benzylidene-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one