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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
—— (2S)-2-(3-hydroxy-4-methoxyphenyl)-2-(prop-2-ynylamino)acetonitrile —— C12H12N2O2
(2S)-2-(3-hydroxy-4-methoxyphenyl)-2-(prop-2-ynylamino)acetonitrile
—— (2R)-2-(3,4-dihydroxyphenyl)-2-(prop-2-enylamino)acetonitrile —— C11H12N2O2
(2R)-2-(3,4-dihydroxyphenyl)-2-(prop-2-enylamino)acetonitrile
—— (2S)-2-[4-(2-methoxyethyl)phenoxy]-2-methylbutan-1-amine —— C14H23NO2
(2S)-2-[4-(2-methoxyethyl)phenoxy]-2-methylbutan-1-amine
—— (5-hydroxy-3,5-dimethyl-4H-pyrazol-1-yl)-(2-hydroxyphenyl)methanethione —— C12H14N2O2S
(5-hydroxy-3,5-dimethyl-4H-pyrazol-1-yl)-(2-hydroxyphenyl)methanethione
—— 3-[(1S)-1-[(1-ethylimidazol-2-yl)methylamino]ethyl]phenol —— C14H19N3O
3-[(1S)-1-[(1-ethylimidazol-2-yl)methylamino]ethyl]phenol
—— 3-[(1R)-1-[(1-ethylimidazol-2-yl)methylamino]ethyl]phenol —— C14H19N3O
3-[(1R)-1-[(1-ethylimidazol-2-yl)methylamino]ethyl]phenol
—— 3-(2-Hydroxy-4-nitrophenyl)-5-[(2-hydroxyphenyl)methylidene]-2-phenylimidazol-4-one —— C22H15N3O5
3-(2-Hydroxy-4-nitrophenyl)-5-[(2-hydroxyphenyl)methylidene]-2-phenylimidazol-4-one
—— 3-(4-Chlorophenyl)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12ClNO3S2
3-(4-Chlorophenyl)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O6S
ethyl 2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[Benzotriazol-1-yl-(4-methylanilino)methyl]-4-nitrophenol —— C20H17N5O3
2-[Benzotriazol-1-yl-(4-methylanilino)methyl]-4-nitrophenol
—— 2-(2,4-dichlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide —— C17H16Cl2N2O4
2-(2,4-dichlorophenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]propanamide
—— 4-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-2,6-dibromobenzene-1,3-diol —— C9H8Br2N6O2
4-[[(4-Amino-1,2,4-triazol-3-yl)hydrazinylidene]methyl]-2,6-dibromobenzene-1,3-diol
—— 3-Bromobenzoic acid 2-[(3-hydroxy-4-methoxyphenyl)methylene]hydrazide 303065-46-5 C15H13BrN2O3
3-Bromobenzoic acid 2-[(3-hydroxy-4-methoxyphenyl)methylene]hydrazide
—— 3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile —— C18H17NO5S
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile
—— 2-Methoxy-6-[(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylhydrazinylidene)methyl]phenol —— C18H18N4O2S
2-Methoxy-6-[(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylhydrazinylidene)methyl]phenol
—— 4-hydroxy-N-[(2R)-2-hydroxypropyl]-N-methyl-3-nitrobenzenesulfonamide —— C10H14N2O6S
4-hydroxy-N-[(2R)-2-hydroxypropyl]-N-methyl-3-nitrobenzenesulfonamide
—— 2-Sulfanylidene-5-[(2,4,6-trichloro-3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C10H4Cl3NO2S2
2-Sulfanylidene-5-[(2,4,6-trichloro-3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazolidine-2,4-dione —— C17H16BrN3O6S
5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazolidine-2,4-dione
—— 2-{(E)-[(4-bromo-2-methylphenyl)imino]methyl}-6-methoxyphenol 196081-76-2 C15H14BrNO2
2-{(E)-[(4-bromo-2-methylphenyl)imino]methyl}-6-methoxyphenol
—— Hydron;phenol —— C6H7O+
Hydron;phenol
—— Amino[(2,5-dihydroxyphenyl)sulfanyl]methaniminium —— C7H9N2O2S+
Amino[(2,5-dihydroxyphenyl)sulfanyl]methaniminium
—— 3'-Hydroxy-4'-methoxyacetophenonoxim 102879-56-1 C9H11NO3
3'-Hydroxy-4'-methoxyacetophenonoxim
—— N-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-6-carboxamide —— C16H12BrN3O6
N-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-6-carboxamide
—— Methyl 7-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazole-6-carboxylate —— C15H15NO5S2
Methyl 7-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazole-6-carboxylate
—— 5-[(3-Bromo-2-hydroxy-5-methoxyphenyl)methylidene]-2-(4-bromophenyl)imino-1,3-thiazolidin-4-one —— C17H12Br2N2O3S
5-[(3-Bromo-2-hydroxy-5-methoxyphenyl)methylidene]-2-(4-bromophenyl)imino-1,3-thiazolidin-4-one
—— 2,3,4a,8a-Tetrachloro-6-ethenyl-5-(3-fluoro-4-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C18H11Cl4FO3
2,3,4a,8a-Tetrachloro-6-ethenyl-5-(3-fluoro-4-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— 5-(3-Chloro-4-hydroxy-5-methoxyphenyl)-6-ethenyl-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H25ClO4
5-(3-Chloro-4-hydroxy-5-methoxyphenyl)-6-ethenyl-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— Copper;[2-[[2-hydroxy-3-[(2-oxoniophenyl)methylideneamino]propyl]iminomethyl]phenyl]oxidanium —— C17H20CuN2O3+4
Copper;[2-[[2-hydroxy-3-[(2-oxoniophenyl)methylideneamino]propyl]iminomethyl]phenyl]oxidanium
—— dioxido(dioxo)uranium;[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]-[oxoniumylidene(pyridin-4-yl)methyl]azanide —— C28H28N6O10U
dioxido(dioxo)uranium;[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]-[oxoniumylidene(pyridin-4-yl)methyl]azanide
—— 2-(2-Hydroxy-3-methoxyphenyl)-7-(propan-2-yl)-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol —— C19H23N3O3S
2-(2-Hydroxy-3-methoxyphenyl)-7-(propan-2-yl)-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol
—— 4-(3-Hydroxypyridin-1-ium-1-yl)benzene-1,2-diol —— C11H10NO3+
4-(3-Hydroxypyridin-1-ium-1-yl)benzene-1,2-diol
—— N-cyclohexyl-N'-[(3-hydroxyphenyl)methylideneamino]butanediamide —— C17H23N3O3
N-cyclohexyl-N'-[(3-hydroxyphenyl)methylideneamino]butanediamide
—— [5-[(2-Hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]urea —— C11H9N3O3S2
[5-[(2-Hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]urea
—— 2-[[Ethyl(2-methylprop-2-enyl)amino]methyl]-5-methoxyphenol —— C14H21NO2
2-[[Ethyl(2-methylprop-2-enyl)amino]methyl]-5-methoxyphenol
—— 42,43,46,47,50,51,54,55-Octakis(1-butylcyclopentyl)nonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentaconta-1(41),3(56),4,6(55),8(54),9,11(53),13(52),14,16(51),18(50),19,21(49),23(48),24,26(47),28(46),29,31(45),33(44),34,36(43),38(42),39-tetracosaene-4,10,14,20,24,30,34,40-octol —— C128H176O8
42,43,46,47,50,51,54,55-Octakis(1-butylcyclopentyl)nonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentaconta-1(41),3(56),4,6(55),8(54),9,11(53),13(52),14,16(51),18(50),19,21(49),23(48),24,26(47),28(46),29,31(45),33(44),34,36(43),38(42),39-tetracosaene-4,10,14,20,24,30,34,40-octol
—— ,47,49,51,53,55-Tetracosaene-4,10,14,20,24,30,34,40-oct —— C104H128O8
,47,49,51,53,55-Tetracosaene-4,10,14,20,24,30,34,40-oct
—— 2,2,2-Trifluoro-1-[2-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methylidene]cyclohexen-1-yl]ethanone —— C16H15F3O4
2,2,2-Trifluoro-1-[2-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methylidene]cyclohexen-1-yl]ethanone
—— 3,4,5-trihydroxy-N-(3-methylbutan-2-ylideneamino)benzamide —— C12H16N2O4
3,4,5-trihydroxy-N-(3-methylbutan-2-ylideneamino)benzamide
—— 16,22,28,34,40,47,55,56-Octatert-butylnonacyclo[42.2.2.29,12.13,7.114,18.120,24.126,30.132,36.138,42]hexapentaconta-1(47),3,5,7(56),9(55),10,12(54),14,16,18(53),20,22,24(52),26(51),27,29,32(50),33,35,38(49),39,41,44(48),45-tetracosaene-5,11,45,49,50,51,52,53-octol —— C88H112O8
16,22,28,34,40,47,55,56-Octatert-butylnonacyclo[42.2.2.29,12.13,7.114,18.120,24.126,30.132,36.138,42]hexapentaconta-1(47),3,5,7(56),9(55),10,12(54),14,16,18(53),20,22,24(52),26(51),27,29,32(50),33,35,38(49),39,41,44(48),45-tetracosaene-5,11,45,49,50,51,52,53-octol
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(2,3-dihydroindol-1-ylmethyl)-N-[1-(4-hydroxy-3-methoxyphenyl)ethylideneamino]triazole-4-carboxamide —— C23H23N9O4
1-(4-amino-1,2,5-oxadiazol-3-yl)-5-(2,3-dihydroindol-1-ylmethyl)-N-[1-(4-hydroxy-3-methoxyphenyl)ethylideneamino]triazole-4-carboxamide
—— 6-Amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(trifluoromethyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C15H10BrF3N4O3
6-Amino-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(trifluoromethyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 2-(2,4-Dihydroxyphenyl)-3-[2-(furan-2-ylmethylsulfanyl)ethyl]-1,3-thiazinan-4-one —— C17H19NO4S2
2-(2,4-Dihydroxyphenyl)-3-[2-(furan-2-ylmethylsulfanyl)ethyl]-1,3-thiazinan-4-one
—— 2-[5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C16H17NO5S2
2-[5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
—— 3-(2-Hydroxy-4-nitrophenyl)-5-[(4-hydroxyphenyl)methylidene]-2-phenylimidazol-4-one —— C22H15N3O5
3-(2-Hydroxy-4-nitrophenyl)-5-[(4-hydroxyphenyl)methylidene]-2-phenylimidazol-4-one
—— N-[2-(4-hydroxyphenyl)ethyl]-3-phenylbutanamide —— C18H21NO2
N-[2-(4-hydroxyphenyl)ethyl]-3-phenylbutanamide
—— 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)propanamide —— C18H18N2O4
2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methoxyphenyl)propanamide
—— 3-Amino-4-hydroxy-5-nitrobenzenesulfonate —— C6H5N2O6S-
3-Amino-4-hydroxy-5-nitrobenzenesulfonate
—— Dimethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(4-fluorobenzyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C23H21BrFNO6
Dimethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-1-(4-fluorobenzyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— 3-(3-Hydroxy-4-methoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile —— C15H12N2O2
3-(3-Hydroxy-4-methoxyphenyl)-2-pyridin-2-ylprop-2-enenitrile
—— 4-amino-N-[(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboxamide —— C10H6Br3N5O3
4-amino-N-[(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboxamide