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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
—— 1-[(5-Hydroxy-2-nitrophenyl)methylideneamino]-3-(2-methylphenyl)urea —— C15H14N4O4
1-[(5-Hydroxy-2-nitrophenyl)methylideneamino]-3-(2-methylphenyl)urea
—— (5Z)-5-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-3-(prop-2-YN-1-YL)-1,3-thiazolidine-2,4-dione —— C14H10ClNO4S
(5Z)-5-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-3-(prop-2-YN-1-YL)-1,3-thiazolidine-2,4-dione
—— 1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-pyridin-3-ylurea —— C16H19N3O2
1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-pyridin-3-ylurea
—— 2-[3-(1,3-Benzodioxol-5-ylmethyl)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-3-(4-ethylpiperazin-1-yl)-3-oxopropanenitrile —— C28H27BrN4O6S
2-[3-(1,3-Benzodioxol-5-ylmethyl)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-3-(4-ethylpiperazin-1-yl)-3-oxopropanenitrile
—— Ethyl 5-(1,3-benzodioxol-5-yl)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylene]-2,3-dihydro-7-methyl-3-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 309921-60-6 C25H21BrN2O7S
Ethyl 5-(1,3-benzodioxol-5-yl)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylene]-2,3-dihydro-7-methyl-3-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 6-Amino-3-(5-chlorothiophen-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C18H13ClN4O3S
6-Amino-3-(5-chlorothiophen-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— propan-2-yl 2-[(2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O4S
propan-2-yl 2-[(2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-(3-chloroanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H18ClNO5S
ethyl 2-(3-chloroanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 2-[(3-Bromo-4-hydroxyphenyl)methylidene]-5-imino-4-(1,3-thiazol-2-yl)thiolan-3-one —— C14H9BrN2O2S2
2-[(3-Bromo-4-hydroxyphenyl)methylidene]-5-imino-4-(1,3-thiazol-2-yl)thiolan-3-one
—— 4-{2-[(3-Chloro-4-methylphenyl)amino]-1,3-thiazol-4-yl}benzene-1,2-diol —— C16H13ClN2O2S
4-{2-[(3-Chloro-4-methylphenyl)amino]-1,3-thiazol-4-yl}benzene-1,2-diol
—— 6-(4-hydroxyphenyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione —— C12H7N3O3
6-(4-hydroxyphenyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione
—— 2-Bromo-4-{[ethyl(pyridin-4-ylmethyl)amino]methyl}-6-methoxyphenol —— C16H19BrN2O2
2-Bromo-4-{[ethyl(pyridin-4-ylmethyl)amino]methyl}-6-methoxyphenol
—— N-[(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2,4,6-tribromophenoxy)acetamide —— C15H10Br3N3O5
N-[(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2,4,6-tribromophenoxy)acetamide
—— methyl 4-(4-hydroxy-3-iodo-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C14H15IN2O4S
methyl 4-(4-hydroxy-3-iodo-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-N-[(3-nitrophenyl)methylideneamino]-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C20H19N5O5S
4-(4-hydroxy-3-methoxyphenyl)-6-methyl-N-[(3-nitrophenyl)methylideneamino]-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 2-[(3,4-dihydroxyphenyl)methylideneamino]-6-methyl-4H-1,3,4-thiadiazin-5-one —— C11H11N3O3S
2-[(3,4-dihydroxyphenyl)methylideneamino]-6-methyl-4H-1,3,4-thiadiazin-5-one
—— N-[(2,4-dichlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide —— C14H10Cl2N2O4
N-[(2,4-dichlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— 2-[(E)-[(4-Methoxyphenyl)imino]methyl]-6-nitrophenol —— C14H12N2O4
2-[(E)-[(4-Methoxyphenyl)imino]methyl]-6-nitrophenol
—— 2-[(E)-[(2-Methoxyphenyl)imino]methyl]-6-nitrophenol —— C14H12N2O4
2-[(E)-[(2-Methoxyphenyl)imino]methyl]-6-nitrophenol
—— (2-Hydroxy-3-methoxyphenyl)methylidene-(phenylcarbamothioylamino)azanium —— C15H16N3O2S+
(2-Hydroxy-3-methoxyphenyl)methylidene-(phenylcarbamothioylamino)azanium
—— 8a-bromo-7-ethenyl-8-(4-hydroxy-3-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19BrO4
8a-bromo-7-ethenyl-8-(4-hydroxy-3-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2-(4-Benzofuran-2-yl-3-methyl-isoxazol-5-yl)-5-methoxy-phenol 75960-81-5 C19H15NO4
2-(4-Benzofuran-2-yl-3-methyl-isoxazol-5-yl)-5-methoxy-phenol
—— N,N'-bis[1-(3-hydroxyphenyl)ethylideneamino]pentanediamide —— C21H24N4O4
N,N'-bis[1-(3-hydroxyphenyl)ethylideneamino]pentanediamide
—— [(Z)-[amino(nitramido)methylidene]amino]-[(3-hydroxy-4-methoxyphenyl)methylidene]azanium —— C9H12N5O4+
[(Z)-[amino(nitramido)methylidene]amino]-[(3-hydroxy-4-methoxyphenyl)methylidene]azanium
—— 2-[[(4-Amino-5-methyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-4-chlorophenol —— C10H11ClN6O
2-[[(4-Amino-5-methyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-4-chlorophenol
—— 5-[(4-Hydroxy-3-iodophenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H10INO2S2
5-[(4-Hydroxy-3-iodophenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— Ethyl 1-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperidine-3-carboxylate —— C19H22N2O5S
Ethyl 1-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperidine-3-carboxylate
—— ethyl 7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-[(2-nitrophenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl 7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-[(2-nitrophenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-(2-hydroxy-5-methoxy-benzylidene)-1,3-dihydro-indol-2-one —— C16H13NO3
3-(2-hydroxy-5-methoxy-benzylidene)-1,3-dihydro-indol-2-one
—— 3-Nitro-4-hydroxy benzaldoxime —— C7H6N2O4
3-Nitro-4-hydroxy benzaldoxime
—— 3-[(2-hydroxy-3-methyl-5-nitrophenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one —— C18H16N2O6
3-[(2-hydroxy-3-methyl-5-nitrophenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one
—— 2-bromo-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H13BrN2O3
2-bromo-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— [(3R)-2,3-dihydro-1,4-benzodioxin-3-yl]-[4-(3-hydroxy-4-nitrobenzoyl)piperazin-1-yl]methanone —— C20H19N3O7
[(3R)-2,3-dihydro-1,4-benzodioxin-3-yl]-[4-(3-hydroxy-4-nitrobenzoyl)piperazin-1-yl]methanone
—— [(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]-[4-(3-hydroxy-4-nitrobenzoyl)piperazin-1-yl]methanone —— C20H19N3O7
[(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]-[4-(3-hydroxy-4-nitrobenzoyl)piperazin-1-yl]methanone
—— 5-(5-Bromo-2-hydroxy-3-methoxyphenyl)-2,3,4a,8a-tetrachloro-6-ethenyl-5,8-dihydronaphthalene-1,4-dione —— C19H13BrCl4O4
5-(5-Bromo-2-hydroxy-3-methoxyphenyl)-2,3,4a,8a-tetrachloro-6-ethenyl-5,8-dihydronaphthalene-1,4-dione
—— 2-{[(4-Hydroxy-2-methylphenyl)amino]methylidene}-4,4-dimethyl-3-oxopentanenitrile —— C15H18N2O2
2-{[(4-Hydroxy-2-methylphenyl)amino]methylidene}-4,4-dimethyl-3-oxopentanenitrile
—— 2-Hydroxy-3-methoxy-5-(morpholin-4-ium-4-ylmethyl)benzaldehyde —— C13H18NO4+
2-Hydroxy-3-methoxy-5-(morpholin-4-ium-4-ylmethyl)benzaldehyde
—— 2-(3,4-Dimethylphenyl)imino-3-ethyl-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1,3-thiazolidin-4-one —— C24H26N2O3S
2-(3,4-Dimethylphenyl)imino-3-ethyl-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-1,3-thiazolidin-4-one
—— ethyl 2-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-5-(4-fluorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17BrFN3O6S
ethyl 2-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-5-(4-fluorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Diethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(3,4-dimethoxybenzyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C27H30BrNO8
Diethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(3,4-dimethoxybenzyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— N-[(2-hydroxyphenyl)methylideneamino]-6-methyl-8-oxo-3,8a-dihydropyrido[2,3-b][1,4]thiazine-2-carboxamide —— C16H14N4O3S
N-[(2-hydroxyphenyl)methylideneamino]-6-methyl-8-oxo-3,8a-dihydropyrido[2,3-b][1,4]thiazine-2-carboxamide
—— 5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-chlorophenyl)-1,3-thiazolidine-2,4-dione —— C17H11BrClNO4S
5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(3-chlorophenyl)-1,3-thiazolidine-2,4-dione
—— 8a-bromo-7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21BrO5
8a-bromo-7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 2-methoxyethyl (6R)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C18H21N3O6S
2-methoxyethyl (6R)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— ethyl (6S)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C17H19N3O5S
ethyl (6S)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— ethyl (6R)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C17H19N3O5S
ethyl (6R)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— 2-methoxyethyl (6S)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C18H21N3O6S
2-methoxyethyl (6S)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— methyl (6S)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate —— C16H17N3O5S
methyl (6S)-3-cyclopropyl-6-(4-hydroxy-3-nitrophenyl)-4-methyl-2-sulfanylidene-1,6-dihydropyrimidine-5-carboxylate
—— (ethylcarbamothioylamino)-[(3-hydroxyphenyl)methylidene]azanium —— C10H14N3OS+
(ethylcarbamothioylamino)-[(3-hydroxyphenyl)methylidene]azanium
—— 1-Ethyl-3-[(4-hydroxy-3-methoxyphenyl)methylideneamino]thiourea —— C11H15N3O2S
1-Ethyl-3-[(4-hydroxy-3-methoxyphenyl)methylideneamino]thiourea