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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)-2-[2-(4,5-dimethylthiazol-2-yl)hydrazino]-5-[(2-hydroxy-3-methoxy-phenyl)methylene]thiazol-4-one —— C16H16N4O3S2
(5Z)-2-[2-(4,5-dimethylthiazol-2-yl)hydrazino]-5-[(2-hydroxy-3-methoxy-phenyl)methylene]thiazol-4-one
—— (4Z)-4-[(5Z)-5-(anilinomethylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-nitrofuran-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C25H20N2O7
(4Z)-4-[(5Z)-5-(anilinomethylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-nitrofuran-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— (E)-2-diethoxyphosphoryl-3-(2-hydroxyphenyl)prop-2-enenitrile —— C13H16NO4P
(E)-2-diethoxyphosphoryl-3-(2-hydroxyphenyl)prop-2-enenitrile
—— 2-(5-Hydroxy-2-methoxyphenyl)acetate —— C9H9O4-
2-(5-Hydroxy-2-methoxyphenyl)acetate
—— (S)-4-Hydroxymandelate —— C8H7O4-
(S)-4-Hydroxymandelate
—— N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2,3,6-trimethylphenoxy)acetamide —— C18H19N3O5
N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2,3,6-trimethylphenoxy)acetamide
—— ethyl (2Z,7S)-7-(4-hydroxy-3-methoxyphenyl)-2-[(3-hydroxyphenyl)methylidene]-5-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O6S
ethyl (2Z,7S)-7-(4-hydroxy-3-methoxyphenyl)-2-[(3-hydroxyphenyl)methylidene]-5-methyl-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(Z)-(3-hydroxy-2-methoxyphenyl)methylideneamino]-2-(2-methylimidazol-1-yl)acetamide —— C14H16N4O3
N-[(Z)-(3-hydroxy-2-methoxyphenyl)methylideneamino]-2-(2-methylimidazol-1-yl)acetamide
—— 2-(2,3-dimethylphenoxy)-N'-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide —— C18H20N2O4
2-(2,3-dimethylphenoxy)-N'-[(Z)-(3-hydroxy-4-methoxyphenyl)methylidene]acetohydrazide
—— (5E)-2-[bis(2-hydroxyethyl)amino]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C14H16N2O4S
(5E)-2-[bis(2-hydroxyethyl)amino]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methylbenzamide —— C16H16N2O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-methylbenzamide
—— N-[(Z)-furan-2-ylmethylideneamino]-4-hydroxy-3-methoxybenzamide —— C13H12N2O4
N-[(Z)-furan-2-ylmethylideneamino]-4-hydroxy-3-methoxybenzamide
—— (1R,6R)-4-chloro-6-[(2-hydroxy-5-nitrophenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid —— C14H13ClN2O6
(1R,6R)-4-chloro-6-[(2-hydroxy-5-nitrophenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid
—— (6E)-6-[(2-hydroxy-5-methylanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one —— C14H12N2O4
(6E)-6-[(2-hydroxy-5-methylanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one
—— (5Z)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-ethyl-2-thioxoimidazolidin-4-one —— C13H13ClN2O3S
(5Z)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-ethyl-2-thioxoimidazolidin-4-one
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-phenylpropanamide —— C17H18N2O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-phenylpropanamide
—— 2-(2,4-dimethylphenoxy)-N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]acetohydrazide —— C17H17N3O5
2-(2,4-dimethylphenoxy)-N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]acetohydrazide
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-methyl-1H-pyrazole-3-carboxamide —— C13H14N4O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-methyl-1H-pyrazole-3-carboxamide
—— 3-[(Z)-1,2,4-triazol-4-yliminomethyl]phenol —— C9H8N4O
3-[(Z)-1,2,4-triazol-4-yliminomethyl]phenol
—— 5-cyclopropyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-pyrazole-3-carboxamide —— C15H16N4O3
5-cyclopropyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-pyrazole-3-carboxamide
—— N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-2-[(2-methylphenyl)amino]acetohydrazide (non-preferred name) —— C16H16N4O4
N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-2-[(2-methylphenyl)amino]acetohydrazide (non-preferred name)
—— (3S)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide —— C16H13N3O6
(3S)-N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
—— 3-(3,5-dioxo-2H-1,2,4-triazin-6-yl)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]propanamide —— C13H13N5O4
3-(3,5-dioxo-2H-1,2,4-triazin-6-yl)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]propanamide
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile —— C16H15N3O3
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile
—— 4-(4-hydroxy-phenyl)-butan-2-one semicarbazone —— C11H15N3O2
4-(4-hydroxy-phenyl)-butan-2-one semicarbazone
—— (2E)-2-(3-hydroxy-4-methoxybenzylidene)-8-methyl[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one —— C18H14N2O3S
(2E)-2-(3-hydroxy-4-methoxybenzylidene)-8-methyl[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-3-carboxamide —— C13H10N4O4
N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-3-carboxamide
—— 1-amino-3-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]urea —— C9H12N4O2
1-amino-3-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]urea
—— Cinnamaldehyde, alpha-[4-(2-formylvinyl)-2-methoxyphenoxy]-4-hydroxy-3-methoxy- —— C20H18O6
Cinnamaldehyde, alpha-[4-(2-formylvinyl)-2-methoxyphenoxy]-4-hydroxy-3-methoxy-
—— (6E)-6-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(trifluoromethyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7-dione —— C13H5BrF3N3O3S
(6E)-6-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(trifluoromethyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7-dione
—— 3-[(Z)-[(Z)-(3-hydroxyphenyl)methylidenehydrazinylidene]methyl]phenol 18428-76-7 C14H12N2O2
3-[(Z)-[(Z)-(3-hydroxyphenyl)methylidenehydrazinylidene]methyl]phenol
—— <i>N</i>-(4-hydroxy-3-methoxy-<i>trans</i>-styryl)-benzamide —— C16H15NO3
<i>N</i>-(4-hydroxy-3-methoxy-<i>trans</i>-styryl)-benzamide
—— ethyl (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-methyl-4-oxo-1H-pyrrole-3-carboxylate —— C15H15NO4
ethyl (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-methyl-4-oxo-1H-pyrrole-3-carboxylate
—— (4E)-4-[(3-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione —— C16H12N2O3
(4E)-4-[(3-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— ethyl (2Z)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2Z)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-(2-hydroxy-3,5-dinitrobenzylidene)-1-(prop-2-en-1-yl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C14H10N4O7S
(5Z)-5-(2-hydroxy-3,5-dinitrobenzylidene)-1-(prop-2-en-1-yl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— methyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H18N2O4S
methyl (2Z)-2-(4-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O5S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl 2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-5-(4-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20BrClN2O5S
ethyl 2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-5-(4-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-5-[4-(methylsulfanyl)phenyl]-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O5S2
ethyl (2Z)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-5-[4-(methylsulfanyl)phenyl]-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-5-[4-(dimethylamino)phenyl]-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H27N3O5S
ethyl (2Z)-5-[4-(dimethylamino)phenyl]-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-5-(4-chlorophenyl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21ClN2O5S
ethyl (2Z)-5-(4-chlorophenyl)-2-(3-hydroxy-4-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-cyclopropyl-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-1H-pyrazole-5-carbohydrazide —— C15H16N4O3
3-cyclopropyl-N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-1H-pyrazole-5-carbohydrazide
—— (5E)-5-[(3-Bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-(prop-2-EN-1-YL)-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H9BrClNO2S2
(5E)-5-[(3-Bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-(prop-2-EN-1-YL)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (4E)-1-(3,4-dichlorophenyl)-4-[(2-hydroxy-5-nitrophenyl)methylidene]pyrazolidine-3,5-dione —— C16H9Cl2N3O5
(4E)-1-(3,4-dichlorophenyl)-4-[(2-hydroxy-5-nitrophenyl)methylidene]pyrazolidine-3,5-dione
—— (E)-N'-(3-hydroxy-4-methoxybenzylidene)-3-methyl-1H-pyrazole-5-carbohydrazide —— C13H14N4O3
(E)-N'-(3-hydroxy-4-methoxybenzylidene)-3-methyl-1H-pyrazole-5-carbohydrazide
—— [(3aR)-9-formyl-6-methyl-3-methylidene-2,7-dioxo-4,5,8,9,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate —— C23H22O7
[(3aR)-9-formyl-6-methyl-3-methylidene-2,7-dioxo-4,5,8,9,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
—— 2-methoxy-5-propyl-hydroquinone —— C10H14O3
2-methoxy-5-propyl-hydroquinone
—— methyl 5-cyano-4-(4-hydroxyphenyl)-2-methyl-6-(1H-pyrrol-1-yl)-4H-pyran-3-carboxylate —— C19H16N2O4
methyl 5-cyano-4-(4-hydroxyphenyl)-2-methyl-6-(1H-pyrrol-1-yl)-4H-pyran-3-carboxylate
—— Phenol, 2-[4-amino-6-(2-pyridin-4-ylvinyl)-[1,3,5]triazin-2-yl]- —— C16H13N5O
Phenol, 2-[4-amino-6-(2-pyridin-4-ylvinyl)-[1,3,5]triazin-2-yl]-