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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
—— 3-[(5R)-5-methyl-4,5-dihydro-1H-imidazol-2-yl]phenol —— C10H12N2O
3-[(5R)-5-methyl-4,5-dihydro-1H-imidazol-2-yl]phenol
—— ethyl 2-(furan-3-ylmethylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O5S
ethyl 2-(furan-3-ylmethylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-Ethyl-6-[1-(hydroxyamino)-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]benzene-1,3-diol —— C14H16N2O3S
4-Ethyl-6-[1-(hydroxyamino)-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]benzene-1,3-diol
—— 4-[(2R)-butan-2-yl]-2-nitrophenol —— C10H13NO3
4-[(2R)-butan-2-yl]-2-nitrophenol
—— 4-[(2S)-butan-2-yl]-2-nitrophenol —— C10H13NO3
4-[(2S)-butan-2-yl]-2-nitrophenol
—— 5-[(2-Hydroxy-3-methylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H9NO2S2
5-[(2-Hydroxy-3-methylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-Cyclohexyl-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one —— C16H16N2O5
2-Cyclohexyl-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one
—— (8S,8aS)-6-amino-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile —— C19H17N5O
(8S,8aS)-6-amino-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile
—— (8S,8aS)-6-amino-8-(3,4-dihydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile —— C19H17N5O2
(8S,8aS)-6-amino-8-(3,4-dihydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile
—— N-[(8S,8aR)-5,7,7-tricyano-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinolin-6-yl]-2-chloroacetamide —— C21H18ClN5O2
N-[(8S,8aR)-5,7,7-tricyano-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinolin-6-yl]-2-chloroacetamide
—— (8S,8aR)-6-amino-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile —— C19H17N5O
(8S,8aR)-6-amino-8-(4-hydroxyphenyl)-2-methyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile
—— 2-methoxyethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
2-methoxyethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 6-[2-(3,5-dibromo-2,4-dihydroxyphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione —— C12H7Br2N3O6
6-[2-(3,5-dibromo-2,4-dihydroxyphenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione
—— 1-benzyl-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C18H22N2O2
1-benzyl-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 1-benzyl-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C18H22N2O2
1-benzyl-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— Methyl 5-[[5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]furan-2-carboxylate —— C18H14BrNO7S
Methyl 5-[[5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]furan-2-carboxylate
—— 4-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C17H12Br2N2O4
4-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— N-(hexan-2-ylideneamino)-3,4,5-trihydroxybenzamide —— C13H18N2O4
N-(hexan-2-ylideneamino)-3,4,5-trihydroxybenzamide
—— Dimethyl 1-(4-chlorobenzyl)-4-(4-hydroxy-3-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C23H22ClNO6
Dimethyl 1-(4-chlorobenzyl)-4-(4-hydroxy-3-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— 5-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one —— C22H26BrClN2O2S
5-[(3-Bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one
—— 3-[5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C13H9Br2NO4S2
3-[5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— Ethyl 6-amino-4-(2-hydroxy-5-nitrophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carboxylate —— C16H16N4O6
Ethyl 6-amino-4-(2-hydroxy-5-nitrophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carboxylate
—— 2-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-imino-4-(1,3-thiazol-2-yl)thiolan-3-one —— C15H11BrN2O3S2
2-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-imino-4-(1,3-thiazol-2-yl)thiolan-3-one
—— N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-[(3,5-dimethylpyrazol-1-yl)methyl]benzamide —— C21H21BrN4O3
N-[(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-[(3,5-dimethylpyrazol-1-yl)methyl]benzamide
—— N-[2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-methylpropyl]-3-hydroxy-4-nitrobenzamide —— C17H25N3O5
N-[2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-methylpropyl]-3-hydroxy-4-nitrobenzamide
—— 3-hydroxy-4-nitro-N-[(1S)-1-pyridin-2-ylethyl]benzamide —— C14H13N3O4
3-hydroxy-4-nitro-N-[(1S)-1-pyridin-2-ylethyl]benzamide
—— 3-hydroxy-N-[(2R)-2-(5-methylfuran-2-yl)-2-morpholin-4-ylethyl]-4-nitrobenzamide —— C18H21N3O6
3-hydroxy-N-[(2R)-2-(5-methylfuran-2-yl)-2-morpholin-4-ylethyl]-4-nitrobenzamide
—— ethyl 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H20N2O5S2
ethyl 2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C16H10Br2N2O2S
5-[(3,5-Dibromo-4-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— 3-hydroxy-4-nitro-N-[(1R)-1-pyridin-3-ylethyl]benzamide —— C14H13N3O4
3-hydroxy-4-nitro-N-[(1R)-1-pyridin-3-ylethyl]benzamide
—— Methyl 1-cyclopentyl-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate —— C20H23NO5
Methyl 1-cyclopentyl-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— N-[(2S)-4-(furan-2-yl)butan-2-yl]-3-hydroxy-4-nitrobenzamide —— C15H16N2O5
N-[(2S)-4-(furan-2-yl)butan-2-yl]-3-hydroxy-4-nitrobenzamide
—— 3-hydroxy-4-nitro-N-[(1S)-1-pyridin-3-ylethyl]benzamide —— C14H13N3O4
3-hydroxy-4-nitro-N-[(1S)-1-pyridin-3-ylethyl]benzamide
—— N-[(2R)-4-(furan-2-yl)butan-2-yl]-3-hydroxy-4-nitrobenzamide —— C15H16N2O5
N-[(2R)-4-(furan-2-yl)butan-2-yl]-3-hydroxy-4-nitrobenzamide
—— N-[(2S)-2-(dimethylamino)-2-thiophen-2-ylethyl]-3-hydroxy-4-nitrobenzamide —— C15H17N3O4S
N-[(2S)-2-(dimethylamino)-2-thiophen-2-ylethyl]-3-hydroxy-4-nitrobenzamide
—— N-[[(2S)-4-benzylmorpholin-2-yl]methyl]-3-hydroxy-4-nitrobenzamide —— C19H21N3O5
N-[[(2S)-4-benzylmorpholin-2-yl]methyl]-3-hydroxy-4-nitrobenzamide
—— 3-hydroxy-4-nitro-N-[(2S)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]benzamide —— C17H19N3O4S
3-hydroxy-4-nitro-N-[(2S)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]benzamide
—— 4-oxazolidin-2-yl-phenol —— C9H11NO2
4-oxazolidin-2-yl-phenol
—— Ethyl 4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-thioxo-4-(trifluoromethyl)hexahydropyrimidine-5-carboxylate —— C16H19F3N2O6S
Ethyl 4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-thioxo-4-(trifluoromethyl)hexahydropyrimidine-5-carboxylate
—— 3-hydroxy-4-nitro-N-[(1S)-1-pyridin-4-ylethyl]benzamide —— C14H13N3O4
3-hydroxy-4-nitro-N-[(1S)-1-pyridin-4-ylethyl]benzamide
—— 3-hydroxy-4-nitro-N-[(1R)-1-pyridin-4-ylethyl]benzamide —— C14H13N3O4
3-hydroxy-4-nitro-N-[(1R)-1-pyridin-4-ylethyl]benzamide
—— 4-(Benzyliminomethyl)benzene-1,2-diol —— C14H13NO2
4-(Benzyliminomethyl)benzene-1,2-diol
—— 6-hydroxy-5-[(2-hydroxy-4-nitrophenyl)iminomethyl]-4-methyl-2-oxo-1H-pyridine-3-carbonitrile —— C14H10N4O5
6-hydroxy-5-[(2-hydroxy-4-nitrophenyl)iminomethyl]-4-methyl-2-oxo-1H-pyridine-3-carbonitrile
—— N-[(3R)-1-benzylpyrrolidin-3-yl]-3-hydroxy-4-nitrobenzamide —— C18H19N3O4
N-[(3R)-1-benzylpyrrolidin-3-yl]-3-hydroxy-4-nitrobenzamide
—— N-[(2,4-dihydroxy-5-nitrophenyl)methylideneamino]-2-(2-methyl-1,3-dioxolan-2-yl)acetamide —— C13H15N3O7
N-[(2,4-dihydroxy-5-nitrophenyl)methylideneamino]-2-(2-methyl-1,3-dioxolan-2-yl)acetamide
—— 2-(1,3-Benzothiazol-2-ylsulfanyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile —— C17H12N2O2S2
2-(1,3-Benzothiazol-2-ylsulfanyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— 4-[bis(5-hydroxy-3-methyl-1H-pyrazol-4-yl)methyl]-2,6-dibromobenzene-1,3-diol —— C15H14Br2N4O4
4-[bis(5-hydroxy-3-methyl-1H-pyrazol-4-yl)methyl]-2,6-dibromobenzene-1,3-diol
—— 2-(4-Hydroxy-3,5-dimethoxyphenyl)ethanimidamide —— C10H14N2O3
2-(4-Hydroxy-3,5-dimethoxyphenyl)ethanimidamide
—— 2-[(2-Hydroxyphenyl)methylidene]-5-imino-4-(1,3-thiazol-2-yl)thiolan-3-one —— C14H10N2O2S2
2-[(2-Hydroxyphenyl)methylidene]-5-imino-4-(1,3-thiazol-2-yl)thiolan-3-one
—— 3-hydroxy-4-nitro-N-[(1R,3S)-3-(trifluoromethyl)cyclohexyl]benzamide —— C14H15F3N2O4
3-hydroxy-4-nitro-N-[(1R,3S)-3-(trifluoromethyl)cyclohexyl]benzamide