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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
—— 5-[(2,3-Dibromo-6-hydroxy-5-methoxyphenyl)methylidene]-2-phenyl-1,3-thiazol-4-one —— C17H11Br2NO3S
5-[(2,3-Dibromo-6-hydroxy-5-methoxyphenyl)methylidene]-2-phenyl-1,3-thiazol-4-one
—— 2-[[(4-Amino-5-methyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-6-bromo-4-nitrophenol —— C10H10BrN7O3
2-[[(4-Amino-5-methyl-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-6-bromo-4-nitrophenol
—— 7-(4-hydroxy-3-nitrophenyl)-N-(2-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C20H18N6O5
7-(4-hydroxy-3-nitrophenyl)-N-(2-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 7-ethenyl-8-(2-hydroxy-6-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
7-ethenyl-8-(2-hydroxy-6-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C15H17N3O4
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C15H17N3O4
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(3-chloro-2-methylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H18ClN3O3
(4S)-1-(3-chloro-2-methylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C14H15N3O3
(4S)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(3-chloro-2-methylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H20ClN3O4
(4S)-1-(3-chloro-2-methylphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-1-(3-chloro-2-methylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H18ClN3O3
(4R)-1-(3-chloro-2-methylphenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methylimino-3-[(Z)-(4-methylphenyl)methylideneamino]-1,3-thiazolidin-4-one —— C20H19N3O3S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methylimino-3-[(Z)-(4-methylphenyl)methylideneamino]-1,3-thiazolidin-4-one
—— ethyl (2E,5R)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17N3O6S2
ethyl (2E,5R)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[(2S)-5-ethyl-3-[N-(5-ethyl-1,3,4-thiadiazol-2-yl)-C-piperidin-1-ylcarbonimidoyl]-2H-1,3,4-thiadiazol-2-yl]phenol —— C20H26N6OS2
2-[(2S)-5-ethyl-3-[N-(5-ethyl-1,3,4-thiadiazol-2-yl)-C-piperidin-1-ylcarbonimidoyl]-2H-1,3,4-thiadiazol-2-yl]phenol
—— 2-[(2R)-5-ethyl-3-[N-(5-ethyl-1,3,4-thiadiazol-2-yl)-C-piperidin-1-ylcarbonimidoyl]-2H-1,3,4-thiadiazol-2-yl]phenol —— C20H26N6OS2
2-[(2R)-5-ethyl-3-[N-(5-ethyl-1,3,4-thiadiazol-2-yl)-C-piperidin-1-ylcarbonimidoyl]-2H-1,3,4-thiadiazol-2-yl]phenol
—— 4-(3-HO-4,5-Dimethoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarbonitrile —— C17H17N3O3
4-(3-HO-4,5-Dimethoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarbonitrile
—— 6-Ethenyl-5-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C24H28O5
6-Ethenyl-5-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— 1-(3-Chloro-4-methylphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]pyrazolidine-3,5-dione —— C17H13ClN2O4
1-(3-Chloro-4-methylphenyl)-4-[(3,4-dihydroxyphenyl)methylidene]pyrazolidine-3,5-dione
—— tert-butyl (7R)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C16H19N5O3
tert-butyl (7R)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— tert-butyl (7S)-7-(3-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C16H19N5O3
tert-butyl (7S)-7-(3-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— tert-butyl (7R)-7-(3-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C16H19N5O3
tert-butyl (7R)-7-(3-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— (2S,5E)-2-(4-ethylanilino)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one —— C18H17N3O4S
(2S,5E)-2-(4-ethylanilino)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidin-4-one
—— tert-butyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C17H21N5O4
tert-butyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— (4S)-1-(4-ethylphenyl)-4-(4-hydroxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H19NO4
(4S)-1-(4-ethylphenyl)-4-(4-hydroxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 2-bromo-4-[[[(1S)-1-cyclopropylethyl]amino]methyl]-6-methoxyphenol —— C13H18BrNO2
2-bromo-4-[[[(1S)-1-cyclopropylethyl]amino]methyl]-6-methoxyphenol
—— 4-[[[(2S)-heptan-2-yl]amino]methyl]benzene-1,2-diol —— C14H23NO2
4-[[[(2S)-heptan-2-yl]amino]methyl]benzene-1,2-diol
—— 2-bromo-4-[[[(1R)-1-cyclopropylethyl]amino]methyl]-6-methoxyphenol —— C13H18BrNO2
2-bromo-4-[[[(1R)-1-cyclopropylethyl]amino]methyl]-6-methoxyphenol
—— 2-bromo-4-[[[(2R)-heptan-2-yl]amino]methyl]-6-methoxyphenol —— C15H24BrNO2
2-bromo-4-[[[(2R)-heptan-2-yl]amino]methyl]-6-methoxyphenol
—— 2-bromo-4-[[[(2S)-heptan-2-yl]amino]methyl]-6-methoxyphenol —— C15H24BrNO2
2-bromo-4-[[[(2S)-heptan-2-yl]amino]methyl]-6-methoxyphenol
—— N-[(1S)-1-cyclopropylethyl]-4-hydroxy-3-nitrobenzenesulfonamide —— C11H14N2O5S
N-[(1S)-1-cyclopropylethyl]-4-hydroxy-3-nitrobenzenesulfonamide
—— 2,4-Dibromo-6-[[methyl-[6-(trifluoromethyl)pyridin-2-yl]hydrazinylidene]methyl]phenol —— C14H10Br2F3N3O
2,4-Dibromo-6-[[methyl-[6-(trifluoromethyl)pyridin-2-yl]hydrazinylidene]methyl]phenol
—— (5E)-3-cyclopentyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H17NO3S2
(5E)-3-cyclopentyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 6-Amino-4-(4-hydroxyphenyl)-3-(4-pyridinyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C18H13N5O2
6-Amino-4-(4-hydroxyphenyl)-3-(4-pyridinyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 4-[[[(2S)-2-hydroxypropyl]amino]methyl]benzene-1,2-diol —— C10H15NO3
4-[[[(2S)-2-hydroxypropyl]amino]methyl]benzene-1,2-diol
—— 5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-[(4-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C19H16N2O7S
5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-[(4-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 5-[[[(2R)-2-hydroxy-2-phenylethyl]amino]methyl]-2-methoxyphenol —— C16H19NO3
5-[[[(2R)-2-hydroxy-2-phenylethyl]amino]methyl]-2-methoxyphenol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C19H17BrN2O3S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 2-[Anilino(benzotriazol-1-yl)methyl]-4-nitrophenol —— C19H15N5O3
2-[Anilino(benzotriazol-1-yl)methyl]-4-nitrophenol
—— 4-Chloro-2-[[4-(2-phenylethynyl)phenyl]methylideneamino]phenol —— C21H14ClNO
4-Chloro-2-[[4-(2-phenylethynyl)phenyl]methylideneamino]phenol
—— 3-Ethyl-2-ethylimino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H20N2O2S
3-Ethyl-2-ethylimino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[(4-Hydroxy-3-methoxyphenyl)methylidenehydrazinylidene]-5-pentyl-1,3-thiazolidin-4-one —— C16H21N3O3S
2-[(4-Hydroxy-3-methoxyphenyl)methylidenehydrazinylidene]-5-pentyl-1,3-thiazolidin-4-one
—— 5-[(Z)-2-(5,6-dimethyl-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C18H17NO2S
5-[(Z)-2-(5,6-dimethyl-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— 4-bromo-2-{(E)-[(tetrahydrofuran-2-ylmethyl)imino]methyl}phenol —— C12H14BrNO2
4-bromo-2-{(E)-[(tetrahydrofuran-2-ylmethyl)imino]methyl}phenol
—— 5,11,17,23-Tetracyclopentylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol —— C48H56O4
5,11,17,23-Tetracyclopentylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 5-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one —— C19H16Br2N2O3S
5-[(2,3-Dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (2-Hydroxy-3,5-diiodobenzylidene)propanedinitrile 727656-13-5 C10H4I2N2O
(2-Hydroxy-3,5-diiodobenzylidene)propanedinitrile
—— N-[(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetamide —— C20H18N2O5S2
N-[(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-2-phenylacetamide
—— 11-[(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid —— C23H31NO6S2
11-[(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid
—— 4-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]-N-[2-(diethylamino)ethyl]benzamide —— C20H23BrN4O4
4-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]-N-[2-(diethylamino)ethyl]benzamide
—— 11-[(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid —— C21H27NO5S2
11-[(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]undecanoic acid
—— (5E)-3-(furan-2-ylmethyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H11NO3S2
(5E)-3-(furan-2-ylmethyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one