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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
—— (3Z)-3-[(5-tert-butyl-2-hydroxy-3-nitrophenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one —— C21H22N2O6
(3Z)-3-[(5-tert-butyl-2-hydroxy-3-nitrophenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one
—— 7-tert-butyl-N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-2,3-dihydro-1,4-benzodioxine-2-carbohydrazide —— C20H21N3O6
7-tert-butyl-N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-2,3-dihydro-1,4-benzodioxine-2-carbohydrazide
—— (2E)-2-[(2-hydroxy-5-nitroanilino)methylidene]-1-benzothiophen-3-one —— C15H10N2O4S
(2E)-2-[(2-hydroxy-5-nitroanilino)methylidene]-1-benzothiophen-3-one
—— ethyl (2Z)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O6S
ethyl (2Z)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one —— C16H17NO4S2
(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one
—— (6E)-4-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H12ClNO2
(6E)-4-chloro-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— [Anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;chloroplatinum(1+) —— C15H16ClN3O2PtS+2
[Anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;chloroplatinum(1+)
—— (2E,5Z)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-[(3-bromophenyl)imino]-1,3-thiazolidin-4-one —— C17H12Br2N2O3S
(2E,5Z)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-[(3-bromophenyl)imino]-1,3-thiazolidin-4-one
—— ethyl (2Z)-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 (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (3E)-3-[(2-hydroxy-5-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H13NO3
(3E)-3-[(2-hydroxy-5-methoxyphenyl)methylidene]-1H-indol-2-one
—— 1,3-Diethyl-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H15N3O5S
1,3-Diethyl-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 5-((<i>Z</i>)-3-hydroxy-benzylidene)-2-phenyl-3,5-dihydro-imidazol-4-one —— C16H12N2O2
5-((<i>Z</i>)-3-hydroxy-benzylidene)-2-phenyl-3,5-dihydro-imidazol-4-one
—— 3-(3,4-dihydroxyphenyl)-N-[(Z)-(3-methoxy-4-phenylmethoxyphenyl)methylideneamino]propanamide —— C24H24N2O5
3-(3,4-dihydroxyphenyl)-N-[(Z)-(3-methoxy-4-phenylmethoxyphenyl)methylideneamino]propanamide
—— (4Z)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-(3-chloro-4-methylphenyl)pyrazolidine-3,5-dione —— C17H12BrClN2O3
(4Z)-4-[(2-bromo-5-hydroxyphenyl)methylidene]-1-(3-chloro-4-methylphenyl)pyrazolidine-3,5-dione
—— (5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one —— C13H13N3O4S
(5Z)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-propyl-2-sulfanylideneimidazolidin-4-one
—— 3-(3,4-dihydroxyphenyl)-N-[(Z)-(3-methoxy-4-propoxyphenyl)methylideneamino]propanamide —— C20H24N2O5
3-(3,4-dihydroxyphenyl)-N-[(Z)-(3-methoxy-4-propoxyphenyl)methylideneamino]propanamide
—— 3,4,5-trihydroxy-N'-[(1Z)-1-(4-nitrophenyl)ethylidene]benzohydrazide —— C15H13N3O6
3,4,5-trihydroxy-N'-[(1Z)-1-(4-nitrophenyl)ethylidene]benzohydrazide
—— propan-2-yl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O5S2
propan-2-yl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-3-(3-chlorophenyl)-5-(3-hydroxy-4-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C17H12ClNO3S2
(5Z)-3-(3-chlorophenyl)-5-(3-hydroxy-4-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 2-(2,6-dimethyl-4-morpholinyl)-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4(5H)-one —— C17H20N2O4S
2-(2,6-dimethyl-4-morpholinyl)-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4(5H)-one
—— N-[(Z)-(3-hydroxyphenyl)methylideneamino]-2-(2-methylimidazol-1-yl)acetamide —— C13H14N4O2
N-[(Z)-(3-hydroxyphenyl)methylideneamino]-2-(2-methylimidazol-1-yl)acetamide
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-3-(piperidin-1-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H18N2O2S2
(5Z)-5-[(2-hydroxyphenyl)methylidene]-3-(piperidin-1-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2,4-dimethylphenoxy)-N'-[(Z)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide —— C17H17N3O5
2-(2,4-dimethylphenoxy)-N'-[(Z)-(3-hydroxy-4-nitrophenyl)methylidene]acetohydrazide
—— 2-(4-Ethylpiperazino)-5-[(E)-1-(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4(5H)-one —— C17H21N3O3S
2-(4-Ethylpiperazino)-5-[(E)-1-(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4(5H)-one
—— 4-bromo-2-methoxy-6-[(E)-2-nitroprop-1-enyl]phenol —— C10H10BrNO4
4-bromo-2-methoxy-6-[(E)-2-nitroprop-1-enyl]phenol
—— (2Z,5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C20H19BrN2O4S
(2Z,5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione —— C12H11NO4S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione
—— ethyl (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylanilino)-4-oxothiophene-3-carboxylate —— C22H21NO5S
ethyl (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylanilino)-4-oxothiophene-3-carboxylate
—— 3,4,5-trihydroxy-N-[(Z)-(3-nitrophenyl)methylideneamino]benzamide —— C14H11N3O6
3,4,5-trihydroxy-N-[(Z)-(3-nitrophenyl)methylideneamino]benzamide
—— 5-(4-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C11H7N3O5S
5-(4-hydroxy-3-nitrobenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— methyl (1Z)-2-(3,5-dihydroxyphenyl)ethanehydrazonate —— C9H12N2O3
methyl (1Z)-2-(3,5-dihydroxyphenyl)ethanehydrazonate
—— (NE)-N-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]thiophene-2-sulfonamide —— C18H16N2O5S3
(NE)-N-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene]thiophene-2-sulfonamide
—— (3Z)-2-amino-4-(3-chloro-4-hydroxy-5-methoxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile —— C14H9ClN4O2
(3Z)-2-amino-4-(3-chloro-4-hydroxy-5-methoxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile
—— 2-hydroxy-N'-[(Z)-(3-methoxyphenyl)methylidene]-3,5-dinitrobenzohydrazide —— C15H12N4O7
2-hydroxy-N'-[(Z)-(3-methoxyphenyl)methylidene]-3,5-dinitrobenzohydrazide
—— 3-Thiazolidineacetamide, N-(2-hydroxy-4-nitrophenyl)-5-[(3-methoxyphenyl)methylene]-4-oxo-2-thioxo-, (5Z)- —— C19H15N3O6S2
3-Thiazolidineacetamide, N-(2-hydroxy-4-nitrophenyl)-5-[(3-methoxyphenyl)methylene]-4-oxo-2-thioxo-, (5Z)-
—— (6Z)-4-(diethylamino)-6-[(2-hydroxy-3-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C17H19N3O4
(6Z)-4-(diethylamino)-6-[(2-hydroxy-3-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— N-[(Z)-(4-chlorophenyl)methylideneamino]-2-hydroxy-3,5-dinitrobenzamide —— C14H9ClN4O6
N-[(Z)-(4-chlorophenyl)methylideneamino]-2-hydroxy-3,5-dinitrobenzamide
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-[(2-methylpiperidin-1-yl)methyl]triazole-4-carboxamide —— C20H25N9O4
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-[(2-methylpiperidin-1-yl)methyl]triazole-4-carboxamide
—— 2-((5-(3-Hydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)methylene)malonamide —— C14H11N3O4S2
2-((5-(3-Hydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)methylene)malonamide
—— N'-[(Z)-(4-chloro-3-nitrophenyl)methylidene]-2-hydroxy-5-nitrobenzohydrazide —— C14H9ClN4O6
N'-[(Z)-(4-chloro-3-nitrophenyl)methylidene]-2-hydroxy-5-nitrobenzohydrazide
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(hydroxymethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H11NO4S2
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(hydroxymethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2Z,5E)-2-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazinylidene]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H16N4O4S2
(2Z,5E)-2-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)hydrazinylidene]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N'-[(Z)-(3-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C16H16N2O6
N'-[(Z)-(3-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— 2-bromo-4-(6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl)-6-methoxyphenol —— C21H16BrN3O2
2-bromo-4-(6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl)-6-methoxyphenol
—— (4Z)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5-one —— C11H8N2O5
(4Z)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5-one
—— (E)-3-[5-[(R)-amino-(2-fluoro-4-hydroxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]prop-2-enoic acid —— C12H10FN3O4
(E)-3-[5-[(R)-amino-(2-fluoro-4-hydroxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]prop-2-enoic acid
—— N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-1,3-benzodioxole-5-carbohydrazide —— C15H11N3O6
N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-1,3-benzodioxole-5-carbohydrazide
—— 5-(6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl)-2-methoxyphenol —— C21H17N3O2
5-(6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl)-2-methoxyphenol
—— (2E)-1-(4-ethylphenyl)-3-[(2-hydroxy-5-methylphenyl)amino]prop-2-en-1-one —— C18H19NO2
(2E)-1-(4-ethylphenyl)-3-[(2-hydroxy-5-methylphenyl)amino]prop-2-en-1-one
—— 2-(1-adamantyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C20H26N2O3
2-(1-adamantyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide