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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
—— 7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— ethyl 5-(4-bromophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O5S
ethyl 5-(4-bromophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione —— C15H13NO3S
5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-prop-2-ynyl-1,3-thiazolidine-2,4-dione
—— (2-Oxoniophenyl)oxidanium;oxovanadium(2+) —— C12H16O5V+6
(2-Oxoniophenyl)oxidanium;oxovanadium(2+)
—— 6-[2-(5-bromo-2-hydroxy-3-nitrophenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione —— C12H7BrN4O7
6-[2-(5-bromo-2-hydroxy-3-nitrophenyl)ethenyl]-5-nitro-1H-pyrimidine-2,4-dione
—— 1-(3-Chlorophenyl)-4-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C17H12ClIN2O4
1-(3-Chlorophenyl)-4-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 2-methoxy-4-[[(2S)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
2-methoxy-4-[[(2S)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol
—— 2-methoxy-4-[[(2R)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
2-methoxy-4-[[(2R)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol
—— 5-methoxy-2-[[(2S)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
5-methoxy-2-[[(2S)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2S)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
2-methoxy-5-[[(2S)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2R)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
2-methoxy-5-[[(2R)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol
—— ethyl 2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17N3O6S2
ethyl 2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-methoxy-2-[[(2R)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
5-methoxy-2-[[(2R)-2-(3-propan-2-yl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenol
—— 7-ethenyl-8-(2-hydroxy-3-methylphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O3
7-ethenyl-8-(2-hydroxy-3-methylphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-chloro-1H-indol-2-one —— C16H11BrClNO3
3-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-chloro-1H-indol-2-one
—— 5-[(3-Bromo-4-hydroxyphenyl)methylidene]-3-[(2-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H11BrClNO3S
5-[(3-Bromo-4-hydroxyphenyl)methylidene]-3-[(2-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 3,4,5-trihydroxy-N-[1-(5-methylthiophen-2-yl)ethylideneamino]benzamide —— C14H14N2O4S
3,4,5-trihydroxy-N-[1-(5-methylthiophen-2-yl)ethylideneamino]benzamide
—— 3,4,5-trihydroxy-N-[1-(4-propylphenyl)ethylideneamino]benzamide —— C18H20N2O4
3,4,5-trihydroxy-N-[1-(4-propylphenyl)ethylideneamino]benzamide
—— 5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-phenoxyethyl)-1,3-thiazolidine-2,4-dione —— C20H19NO6S
5-[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-phenoxyethyl)-1,3-thiazolidine-2,4-dione
—— 5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-2-phenylimino-3-(3-phenylpropyl)-1,3-thiazolidin-4-one —— C27H26N2O2S
5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-2-phenylimino-3-(3-phenylpropyl)-1,3-thiazolidin-4-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-hydroxyphenyl)imino-1,3-thiazolidin-4-one —— C16H12N2O4S
5-[(3,4-Dihydroxyphenyl)methylidene]-2-(2-hydroxyphenyl)imino-1,3-thiazolidin-4-one
—— zinc;[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]-[oxoniumylidene(pyridin-4-yl)methyl]azanide —— C14H14N3O3Zn+3
zinc;[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]-[oxoniumylidene(pyridin-4-yl)methyl]azanide
—— 1-[(2R)-2-(4-hydroxy-3-methoxyphenyl)-5-phenyl-2H-1,3,4-oxadiazol-3-yl]ethanone —— C17H16N2O4
1-[(2R)-2-(4-hydroxy-3-methoxyphenyl)-5-phenyl-2H-1,3,4-oxadiazol-3-yl]ethanone
—— 1-[(2R)-5-(4-bromophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone —— C17H15BrN2O4
1-[(2R)-5-(4-bromophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
—— (4R)-4-(3,4-dihydroxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C13H13N3O3
(4R)-4-(3,4-dihydroxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C13H13N3O2
(4R)-4-(4-hydroxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— (4S)-4-(3-hydroxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one —— C13H13N3O2
(4S)-4-(3-hydroxyphenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
—— 5,11,17,23,29,35-Hexacyclopentylheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15,17,19(40),21(39),22,24,27(38),28,30,33(37),34-octadecaene-37,38,39,40,41,42-hexol —— C72H84O6
5,11,17,23,29,35-Hexacyclopentylheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15,17,19(40),21(39),22,24,27(38),28,30,33(37),34-octadecaene-37,38,39,40,41,42-hexol
—— 2-(benzotriazol-1-yl)-N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]propanamide —— C17H17N5O3
2-(benzotriazol-1-yl)-N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]propanamide
—— 5-(3-Bromo-4-hydroxy-5-methoxyphenyl)-6-ethenyl-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H25BrO4
5-(3-Bromo-4-hydroxy-5-methoxyphenyl)-6-ethenyl-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— 2-Bromo-6-methoxy-4-{[(2-methoxyethyl)amino]methyl}phenol —— C11H16BrNO3
2-Bromo-6-methoxy-4-{[(2-methoxyethyl)amino]methyl}phenol
—— Dimethyl 4-(4-HO-3-I-5-meo-PH)-2,6-DI-ME-1,4-dihydro-3,5-pyridinedicarboxylate —— C18H20INO6
Dimethyl 4-(4-HO-3-I-5-meo-PH)-2,6-DI-ME-1,4-dihydro-3,5-pyridinedicarboxylate
—— N-[2-(3,4-dihydroxyphenyl)ethyl]furan-2-carboxamide —— C13H13NO4
N-[2-(3,4-dihydroxyphenyl)ethyl]furan-2-carboxamide
—— 4-Chloro-2-[[(1,1-dioxo-1,2-benzothiazol-3-yl)-methylhydrazinylidene]methyl]-6-methoxyphenol —— C16H14ClN3O4S
4-Chloro-2-[[(1,1-dioxo-1,2-benzothiazol-3-yl)-methylhydrazinylidene]methyl]-6-methoxyphenol
—— Phenyl[2,2'-{(phenylphosphinediyl)bis[(hydroxy-kappao)methylene]}diphenolato(3-)-kappao]borate(1-) —— C26H21BO4P-
Phenyl[2,2'-{(phenylphosphinediyl)bis[(hydroxy-kappao)methylene]}diphenolato(3-)-kappao]borate(1-)
—— N-[1-(4-fluorophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H13FN2O4
N-[1-(4-fluorophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-(3-chloro-4-methoxyphenyl)-2-[5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H17ClN2O6S
N-(3-chloro-4-methoxyphenyl)-2-[5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 4-[[5-[(1R)-1-aminopentyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C14H19N3O2
4-[[5-[(1R)-1-aminopentyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— 4-[[5-[(1R)-1-aminopropyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C12H15N3O2
4-[[5-[(1R)-1-aminopropyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— 4-[[5-[(1S)-1-aminopropyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C12H15N3O2
4-[[5-[(1S)-1-aminopropyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— 4-[[5-[(1S)-1-aminopentyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C14H19N3O2
4-[[5-[(1S)-1-aminopentyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— (Z)-2-[4-(4-ethoxyphenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C21H18N2O3S
(Z)-2-[4-(4-ethoxyphenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— N'-hydroxy-3-(4-hydroxyphenyl)propanimidamide —— C9H12N2O2
N'-hydroxy-3-(4-hydroxyphenyl)propanimidamide
—— 4-Amino-6-tert-butyl-3-[2-[(4-hydroxyphenyl)methylidene]hydrazinyl]-1,2,4-triazin-5-one —— C14H18N6O2
4-Amino-6-tert-butyl-3-[2-[(4-hydroxyphenyl)methylidene]hydrazinyl]-1,2,4-triazin-5-one
—— (2Z)-5-[(3,4-dimethylphenyl)methyl]-2-[(4-hydroxy-3-methoxyphenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one —— C20H21N3O3S
(2Z)-5-[(3,4-dimethylphenyl)methyl]-2-[(4-hydroxy-3-methoxyphenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one
—— (Z)-2-cyano-3-[5-(2,3-dichlorophenyl)furan-2-yl]-N-(2-hydroxy-4-nitrophenyl)prop-2-enamide —— C20H11Cl2N3O5
(Z)-2-cyano-3-[5-(2,3-dichlorophenyl)furan-2-yl]-N-(2-hydroxy-4-nitrophenyl)prop-2-enamide
—— N-(4-bromophenyl)-N'-[(4-hydroxy-3-methoxyphenyl)methylideneamino]butanediamide —— C18H18BrN3O4
N-(4-bromophenyl)-N'-[(4-hydroxy-3-methoxyphenyl)methylideneamino]butanediamide
—— 3-[(2-Chloro-6-fluorophenyl)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H13ClFNO4S
3-[(2-Chloro-6-fluorophenyl)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 2-(2-Hydroxy-3-methylphenyl)-5-iodo-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C22H18IN3O5
2-(2-Hydroxy-3-methylphenyl)-5-iodo-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone