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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
—— N'-[(E)-(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-4-hydroxy-3-methoxybenzohydrazide —— C15H13ClN2O4
N'-[(E)-(3-chloro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-4-hydroxy-3-methoxybenzohydrazide
—— ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[(5Z)-5-(2,4-dichlorobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C18H11Cl2N3O6S
2-[(5Z)-5-(2,4-dichlorobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide
—— (5E)-5-[(3,4-dihydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H11NO4S
(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— (4Z)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one —— C18H17N3O2
(4Z)-4-[(4-hydroxy-2-methylanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one
—— (e)-6-(2-Hydroxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1h,3h)-dione —— C12H8N4O7
(e)-6-(2-Hydroxy-5-nitrostyryl)-5-nitropyrimidine-2,4(1h,3h)-dione
—— (4Z)-4-(3,4-dihydroxybenzylidene)-2-(3,4-dimethylphenyl)-5-hydroxy-2,4-dihydro-3H-pyrazol-3-one —— C18H16N2O4
(4Z)-4-(3,4-dihydroxybenzylidene)-2-(3,4-dimethylphenyl)-5-hydroxy-2,4-dihydro-3H-pyrazol-3-one
—— N'-[(Z)-(3-hydroxyphenyl)methylideneamino]pyridine-2-carboximidamide —— C13H12N4O
N'-[(Z)-(3-hydroxyphenyl)methylideneamino]pyridine-2-carboximidamide
—— N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-2-carboxamide —— C13H10N4O4
N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-2-carboxamide
—— 11-[(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]undecanoic acid —— C22H29NO5S2
11-[(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]undecanoic acid
—— (5S)-5-(2-hydroxy-3-methoxyphenyl)-3-methyl-2,4,5,6-tetrahydropyrazolo[4,3-d]pyrimidin-7-one —— C13H14N4O3
(5S)-5-(2-hydroxy-3-methoxyphenyl)-3-methyl-2,4,5,6-tetrahydropyrazolo[4,3-d]pyrimidin-7-one
—— (5R)-5-(2-hydroxy-3-methoxyphenyl)-3-methyl-2,4,5,6-tetrahydropyrazolo[4,3-d]pyrimidin-7-one —— C13H14N4O3
(5R)-5-(2-hydroxy-3-methoxyphenyl)-3-methyl-2,4,5,6-tetrahydropyrazolo[4,3-d]pyrimidin-7-one
—— 4-amino-N'-(3-hydroxybenzylidene)-1,2,5-oxadiazole-3-carbohydrazide —— C10H9N5O3
4-amino-N'-(3-hydroxybenzylidene)-1,2,5-oxadiazole-3-carbohydrazide
—— Cambridge id 5476375 —— C11H13NO4
Cambridge id 5476375
—— N-[(E)-cyclohex-3-en-1-ylmethylideneamino]-4-hydroxy-3-methoxybenzamide —— C15H18N2O3
N-[(E)-cyclohex-3-en-1-ylmethylideneamino]-4-hydroxy-3-methoxybenzamide
—— 4-hydroxy-N'-[(E)-indol-3-ylidenemethyl]-3-methoxybenzohydrazide —— C17H15N3O3
4-hydroxy-N'-[(E)-indol-3-ylidenemethyl]-3-methoxybenzohydrazide
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one —— C11H10N2O3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
—— (5E)-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C10H6N4O6S
(5E)-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— N-[(2S)-1-cyanopropan-2-yl]-3-(2-hydroxyphenyl)propanamide —— C13H16N2O2
N-[(2S)-1-cyanopropan-2-yl]-3-(2-hydroxyphenyl)propanamide
—— N-[(2R)-1-cyanopropan-2-yl]-3-(2-hydroxyphenyl)propanamide —— C13H16N2O2
N-[(2R)-1-cyanopropan-2-yl]-3-(2-hydroxyphenyl)propanamide
—— 1,3-dicyclohexyl-5-[(2-hydroxy-5-nitroanilino)methylidene]-1,3-diazinane-2,4,6-trione —— C23H28N4O6
1,3-dicyclohexyl-5-[(2-hydroxy-5-nitroanilino)methylidene]-1,3-diazinane-2,4,6-trione
—— 3-fluoro-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]benzohydrazide —— C14H10FN3O4
3-fluoro-N'-[(E)-(3-hydroxy-4-nitrophenyl)methylidene]benzohydrazide
—— 4-amino-N'-[(E)-(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboximidamide —— C10H10N6O2
4-amino-N'-[(E)-(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboximidamide
—— (6Z)-6-[(2-hydroxy-4-nitroanilino)methylidene]-2,4-diiodocyclohexa-2,4-dien-1-one —— C13H8I2N2O4
(6Z)-6-[(2-hydroxy-4-nitroanilino)methylidene]-2,4-diiodocyclohexa-2,4-dien-1-one
—— (5Z)-5-(4-hydroxy-3-methoxybenzylidene)-1-(prop-2-en-1-yl)-2-sulfanylpyrimidine-4,6(1H,5H)-dione —— C15H14N2O4S
(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-1-(prop-2-en-1-yl)-2-sulfanylpyrimidine-4,6(1H,5H)-dione
—— 2-(2-Hydroxy-phenyl)-5,5-dimethyl-4-phenyl-2,5-dihydro-imidazol-1-ol 122981-56-0 C17H18N2O2
2-(2-Hydroxy-phenyl)-5,5-dimethyl-4-phenyl-2,5-dihydro-imidazol-1-ol
—— 2-methoxy-5-[(E)-(4H-1,2,4-triazol-4-ylimino)methyl]phenol —— C10H10N4O2
2-methoxy-5-[(E)-(4H-1,2,4-triazol-4-ylimino)methyl]phenol
—— 2-(5-Hydroxynonan-5-yl)phenol —— C15H24O2
2-(5-Hydroxynonan-5-yl)phenol
—— N'-[(E)-(3-hydroxyphenyl)methylidene]-3-phenylpropanehydrazide —— C16H16N2O2
N'-[(E)-(3-hydroxyphenyl)methylidene]-3-phenylpropanehydrazide
—— (5Z)-5-(4-hydroxybenzylidene)-3-(3-methoxypropyl)-2-thioxo-1,3-thiazolidin-4-one —— C14H15NO3S2
(5Z)-5-(4-hydroxybenzylidene)-3-(3-methoxypropyl)-2-thioxo-1,3-thiazolidin-4-one
—— (3R)-1-(2,2-dimethylpropanoyl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide —— C19H28N2O4
(3R)-1-(2,2-dimethylpropanoyl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide
—— 4-(2-amino-1,3-thiazol-4-yl)benzene-1,3-diol Hydrochloride —— C9H9ClN2O2S
4-(2-amino-1,3-thiazol-4-yl)benzene-1,3-diol Hydrochloride
—— (3S)-1-(2,2-dimethylpropanoyl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide —— C19H28N2O4
(3S)-1-(2,2-dimethylpropanoyl)-N-[(4-hydroxy-3-methoxyphenyl)methyl]piperidine-3-carboxamide
—— methyl (5E)-5-[(3-hydroxyphenyl)methylidene]-2-methyl-4-oxo-1H-pyrrole-3-carboxylate —— C14H13NO4
methyl (5E)-5-[(3-hydroxyphenyl)methylidene]-2-methyl-4-oxo-1H-pyrrole-3-carboxylate
—— ethyl (2Z)-2-(5-chloro-2-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19ClN2O4S
ethyl (2Z)-2-(5-chloro-2-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-3-methyl-1H-pyrazole-5-carbohydrazide —— C12H11N5O4
N'-[(E)-(5-hydroxy-2-nitrophenyl)methylidene]-3-methyl-1H-pyrazole-5-carbohydrazide
—— (5Z)-5-(4-hydroxybenzylidene)-3-(propan-2-yl)-2-thioxo-1,3-thiazolidin-4-one —— C13H13NO2S2
(5Z)-5-(4-hydroxybenzylidene)-3-(propan-2-yl)-2-thioxo-1,3-thiazolidin-4-one
—— ethyl (2Z)-5-(2,5-dimethoxyphenyl)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2Z)-5-(2,5-dimethoxyphenyl)-2-(4-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 5-(1,3-benzodioxol-5-yl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22N2O7S
ethyl 5-(1,3-benzodioxol-5-yl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrN3O6S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20BrN3O7S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4Z)-1-(3-chloro-4-methylphenyl)-4-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]pyrazolidine-3,5-dione —— C21H14ClN3O6
(4Z)-1-(3-chloro-4-methylphenyl)-4-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]pyrazolidine-3,5-dione
—— Benzaldehyde [3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]hydrazone —— C16H13N3O2S
Benzaldehyde [3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]hydrazone
—— 5-[(E)-(2-{1-Benzyl-1H-pyrazolo[3,4-D]pyrimidin-4-YL}hydrazin-1-ylidene)methyl]-2-methoxyphenol —— C20H18N6O2
5-[(E)-(2-{1-Benzyl-1H-pyrazolo[3,4-D]pyrimidin-4-YL}hydrazin-1-ylidene)methyl]-2-methoxyphenol
—— (5E)-1-(2,4-dichlorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H9Cl2N3O5S
(5E)-1-(2,4-dichlorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12N2O5S2
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H11BrN2O5S2
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-1-(4-chlorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H10ClN3O5S
(5E)-1-(4-chlorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one —— C17H8BrF3N2O4S2
(5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12N2O5S2
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one