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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
—— (3S)-1-butanoyl-N-[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]piperidine-3-carboxamide —— C19H28N2O4
(3S)-1-butanoyl-N-[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]piperidine-3-carboxamide
—— (3R)-1-butanoyl-N-[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]piperidine-3-carboxamide —— C19H28N2O4
(3R)-1-butanoyl-N-[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]piperidine-3-carboxamide
—— 2-[[4-[(4-Ethylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol —— C21H30N2O2+2
2-[[4-[(4-Ethylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol
—— 2-[[4-[(2-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol —— C19H25BrN2O2+2
2-[[4-[(2-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol
—— 2-(4-Methoxyphenyl)ethyl 2-[[5-(cyclohexylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetate —— C19H25N3O3S2
2-(4-Methoxyphenyl)ethyl 2-[[5-(cyclohexylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetate
—— 1-[(1R)-1-cyclopropylethyl]-3-[2-(3-hydroxyphenyl)ethyl]-1-methylurea —— C15H22N2O2
1-[(1R)-1-cyclopropylethyl]-3-[2-(3-hydroxyphenyl)ethyl]-1-methylurea
—— 1-[[(1R)-cyclohex-3-en-1-yl]methyl]-3-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]urea —— C17H24N2O4
1-[[(1R)-cyclohex-3-en-1-yl]methyl]-3-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]urea
—— (1S,3S)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide —— C17H22F3NO3
(1S,3S)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide
—— (1R,3S)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide —— C17H22F3NO3
(1R,3S)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide
—— (1R,3R)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide —— C17H22F3NO3
(1R,3R)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide
—— (1S,3R)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide —— C17H22F3NO3
(1S,3R)-N-[2-(2-hydroxy-4-methoxyphenyl)ethyl]-3-(trifluoromethyl)cyclohexane-1-carboxamide
—— (E)-3-(3-hydroxy-4-methoxyphenyl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile —— C17H18N4O2
(E)-3-(3-hydroxy-4-methoxyphenyl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile
—— 2,6-Dimethoxy-4-[[4-[(2-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C21H30N2O3+2
2,6-Dimethoxy-4-[[4-[(2-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 5-(2-Hydroxy-4-nitroanilino)-5-oxopentanoate —— C11H11N2O6-
5-(2-Hydroxy-4-nitroanilino)-5-oxopentanoate
—— (5Z)-5-[(3-hydroxyphenyl)methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H15NO3S2
(5Z)-5-[(3-hydroxyphenyl)methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (4S)-4-(2-chloro-4-hydroxy-5-methoxyphenyl)-6-propyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H21ClN2O4S
ethyl (4S)-4-(2-chloro-4-hydroxy-5-methoxyphenyl)-6-propyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (4S)-4-(2-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C20H21N3O4S
(4S)-4-(2-hydroxy-3-methoxyphenyl)-N-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 1-[(5R)-3-butyl-5-hydroxy-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one —— C17H21F3N2O3
1-[(5R)-3-butyl-5-hydroxy-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one
—— (4R)-N-(4-fluorophenyl)-4-(2-hydroxy-3-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C18H15FN4O4S
(4R)-N-(4-fluorophenyl)-4-(2-hydroxy-3-nitrophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 2-(4-fluorophenyl)sulfanyl-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H14FNO3S
2-(4-fluorophenyl)sulfanyl-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenoxy)propanamide —— C17H19NO4
N-(3-hydroxy-4-methoxyphenyl)-3-(4-methylphenoxy)propanamide
—— (E)-3-(furan-2-yl)-N-(3-hydroxy-4-methoxyphenyl)prop-2-enamide —— C14H13NO4
(E)-3-(furan-2-yl)-N-(3-hydroxy-4-methoxyphenyl)prop-2-enamide
—— 2-(2-bromo-4-fluorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H13BrFNO4
2-(2-bromo-4-fluorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(4-tert-butylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C19H23NO4
2-(4-tert-butylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(3,4-dichlorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H13Cl2NO3
2-(3,4-dichlorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(3,5-dimethylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C17H19NO4
2-(3,5-dimethylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]acetamide —— C19H21NO5
N-(3-hydroxy-4-methoxyphenyl)-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]acetamide
—— 2-(4-chlorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H14ClNO3
2-(4-chlorophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(2,3-dihydro-1H-inden-5-yloxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C18H19NO4
2-(2,3-dihydro-1H-inden-5-yloxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-2-(4-phenylmethoxyphenoxy)acetamide —— C22H21NO5
N-(3-hydroxy-4-methoxyphenyl)-2-(4-phenylmethoxyphenoxy)acetamide
—— 2-(4-bromophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H14BrNO3
2-(4-bromophenyl)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(4-chloro-3-methylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C16H16ClNO4
2-(4-chloro-3-methylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— (5Z)-3-(benzyliminomethyl)-5-[(4-hydroxyphenyl)methylidene]pyrrolidine-2,4-dione —— C19H16N2O3
(5Z)-3-(benzyliminomethyl)-5-[(4-hydroxyphenyl)methylidene]pyrrolidine-2,4-dione
—— N-(3-hydroxy-4-methoxyphenyl)-2-(2-methylphenyl)sulfanylacetamide —— C16H17NO3S
N-(3-hydroxy-4-methoxyphenyl)-2-(2-methylphenyl)sulfanylacetamide
—— 2-(4-bromophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H14BrNO4
2-(4-bromophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(2-bromo-4-chlorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H13BrClNO4
2-(2-bromo-4-chlorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— 2-(4-Chlorophenyl)ethyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]azanium —— C17H21ClNO3+
2-(4-Chlorophenyl)ethyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]azanium
—— ethyl (4S)-4-(2-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17BrN2O4S
ethyl (4S)-4-(2-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (4-hydroxy-3-methoxyphenyl)methyl-[(2S)-1-[(4-hydroxy-3-methoxyphenyl)methylazaniumyl]propan-2-yl]azanium —— C19H28N2O4+2
(4-hydroxy-3-methoxyphenyl)methyl-[(2S)-1-[(4-hydroxy-3-methoxyphenyl)methylazaniumyl]propan-2-yl]azanium
—— ethyl N-[(2Z)-2-[(5-chloro-2-hydroxyanilino)methylidene]-3-oxobutanoyl]carbamate —— C14H15ClN2O5
ethyl N-[(2Z)-2-[(5-chloro-2-hydroxyanilino)methylidene]-3-oxobutanoyl]carbamate
—— 1-[(3R)-5-(3-hydroxyphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C17H16N2O2
1-[(3R)-5-(3-hydroxyphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— 1-[(3S)-5-(3-hydroxyphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C17H16N2O2
1-[(3S)-5-(3-hydroxyphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— 5-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate —— C19H19N2O5S-
5-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate
—— 4-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid —— C19H18N2O4
4-[(3S)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid
—— 4-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid —— C18H18N2O5S
4-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-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-oxopentanoic acid —— C19H20N2O5S
5-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-5-oxopentanoic acid
—— 5-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate —— C20H19N2O4-
5-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5-oxopentanoate
—— 4-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate —— C18H17N2O5S-
4-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate
—— 4-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid —— C18H18N2O5S
4-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid
—— 4-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate —— C19H17N2O4-
4-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-4-oxobutanoate