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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
—— N-but-2-enyl-N-(2,2-diethoxyethyl)-3-hydroxy-2-nitrobenzamide 94295-89-3 C17H24N2O6
N-but-2-enyl-N-(2,2-diethoxyethyl)-3-hydroxy-2-nitrobenzamide
—— ethyl (5-chloro-2-hydroxyphenyl)acetate 76322-41-3 C10H11ClO3
ethyl (5-chloro-2-hydroxyphenyl)acetate
—— 4-(4-hydroxyphenyl)-3,6-dimethyl-N-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 1349163-70-7 C21H20N4O2
4-(4-hydroxyphenyl)-3,6-dimethyl-N-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
—— 1-(2-hydroxy-5-nitrophenyl)prop-2-yn-1-ol 206664-21-3 C9H7NO4
1-(2-hydroxy-5-nitrophenyl)prop-2-yn-1-ol
—— 7-(4-hydroxy-3-methoxyphenyl)-5-methyl-N6-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide 951999-89-6 C22H21N5O4
7-(4-hydroxy-3-methoxyphenyl)-5-methyl-N6-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide
—— 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide 378785-21-8 C19H19N3O4
4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
—— 4-bromo-2-methoxy-3-methylphenol 287117-36-6 C8H9BrO2
4-bromo-2-methoxy-3-methylphenol
—— 2-(bromomethyl)-4-methoxyphenol 1013914-85-6 C8H9BrO2
2-(bromomethyl)-4-methoxyphenol
—— 2-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenol 24392-96-9 C13H18O3
2-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenol
—— 2-(tert-butyl)-4-(2-hydroxyethyl)phenol 176308-57-9 C12H18O2
2-(tert-butyl)-4-(2-hydroxyethyl)phenol
—— 2-[4-(2,2-diethoxyethoxy)phenyl]ethanol 1000506-05-7 C14H22O4
2-[4-(2,2-diethoxyethoxy)phenyl]ethanol
—— 2-bromo-5-fluoro-4-methylphenol 1268511-85-8 C7H6BrFO
2-bromo-5-fluoro-4-methylphenol
—— 8-Hydroxy<2.2>metaparacyclophane 145223-55-8 C16H16O
8-Hydroxy<2.2>metaparacyclophane
—— 4-tert-Butyl-3-nitrophenol 70634-30-9 C10H13NO3
4-tert-Butyl-3-nitrophenol
—— 4-[3-(1H-1,2,4-triazol-1-yl)propoxy]phenol 80200-03-9 C11H13N3O2
4-[3-(1H-1,2,4-triazol-1-yl)propoxy]phenol
—— 4-[2-(1H-1,2,4-triazol-1-yl)ethoxy]phenol 80200-01-7 C10H11N3O2
4-[2-(1H-1,2,4-triazol-1-yl)ethoxy]phenol
—— 5-tert-Butyl-8-hydroxy<2.2>metaparacyclophane 145223-52-5 C20H24O
5-tert-Butyl-8-hydroxy<2.2>metaparacyclophane
—— 9,16,25,32-Tetrahydroxy<3.1.3.1>metacyclophane 142836-06-4 C32H32O4
9,16,25,32-Tetrahydroxy<3.1.3.1>metacyclophane
—— 3-Hydroxy-I+/--[[(2-thienylmethyl)amino]methyl]benzenemethanol 869951-28-0 C13H15NO2S
3-Hydroxy-I+/--[[(2-thienylmethyl)amino]methyl]benzenemethanol
—— 2-hydroxy-4-methoxy-2',2'-dimethylallylbenzene 25974-59-8 C12H16O2
2-hydroxy-4-methoxy-2',2'-dimethylallylbenzene
—— ethyl 3-((4-hydroxyphenyl)methylthio)propionate 478162-98-0 C12H16O3S
ethyl 3-((4-hydroxyphenyl)methylthio)propionate
—— 3-(dec-1-ynyl)phenol 1418137-01-5 C16H22O
3-(dec-1-ynyl)phenol
—— 2-(2',5'-dihydroxyphenyl)-5-phenylpentane 75632-03-0 C17H20O2
2-(2',5'-dihydroxyphenyl)-5-phenylpentane
—— 2,4-dibromo-5-chlorophenol 89284-48-0 C6H3Br2ClO
2,4-dibromo-5-chlorophenol
—— 2-(3-Chloro-2-propenyl)phenol 86694-60-2 C9H9ClO
2-(3-Chloro-2-propenyl)phenol
—— 2,6-di(3-chloro-2-propenyl)phenol 102117-73-7 C12H12Cl2O
2,6-di(3-chloro-2-propenyl)phenol
—— 2,6-difluoro-3-nitrophenol 1393179-72-0 C6H3F2NO3
2,6-difluoro-3-nitrophenol
—— 5-chlorosalicylaldehyde 6-methyl-4-hydroxypyrimidinyl hydrazone 91398-46-8 C12H11ClN4O2
5-chlorosalicylaldehyde 6-methyl-4-hydroxypyrimidinyl hydrazone
—— 5-bromosalicylaldehyde 6-methyl-4-hydroxypyrimidinyl hydrazone 220164-57-8 C12H11BrN4O2
5-bromosalicylaldehyde 6-methyl-4-hydroxypyrimidinyl hydrazone
—— 5-(5-bromo-2-hydroxyphenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazole 1049130-30-4 C15H12BrFN2O
5-(5-bromo-2-hydroxyphenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazole
—— bis-(5-chlorosalicylidene)thiocarbohydrazone 6956-36-1 C15H12Cl2N4O2S
bis-(5-chlorosalicylidene)thiocarbohydrazone
—— 2-amino-5-chloro-3-nitrophenol 924274-94-2 C6H5ClN2O3
2-amino-5-chloro-3-nitrophenol
—— 5-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)-4,5-dihydropyrazole 1049130-24-6 C15H12Cl2N2O
5-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)-4,5-dihydropyrazole
—— 5-(5-chloro-2-hydroxyphenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazole 1049117-55-6 C15H12ClFN2O
5-(5-chloro-2-hydroxyphenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazole
—— 4-[6-(4-Hydroxyphenyl)-1,2-dihydro-1,2,4,5-tetrazin-3-yl]phenol 53876-71-4 C14H12N4O2
4-[6-(4-Hydroxyphenyl)-1,2-dihydro-1,2,4,5-tetrazin-3-yl]phenol
—— 4-[(Dichloroamino)methyl]phenol 1158998-90-3 C7H7Cl2NO
4-[(Dichloroamino)methyl]phenol
—— 2-((pyrrolidin-1-yl)methyleneamino)phenol 1323158-66-2 C11H14N2O
2-((pyrrolidin-1-yl)methyleneamino)phenol
—— 4-bromo-2-(((4-chlorophenyl)imino)methyl)phenol 16434-76-7 C13H9BrClNO
4-bromo-2-(((4-chlorophenyl)imino)methyl)phenol
—— 2,6-Dimethyl-3-(2,2,2-trifluoroethylamino)phenol —— C10H12F3NO
2,6-Dimethyl-3-(2,2,2-trifluoroethylamino)phenol
—— 3-chloro-4-(2-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol —— C12H11ClN2OS
3-chloro-4-(2-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol
—— 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-3-methylphenol —— C12H12N2OS
4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-3-methylphenol
—— 3-methyl-4-(2-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol —— C13H14N2OS
3-methyl-4-(2-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol
—— 3-chloro-4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol —— C11H9ClN2OS
3-chloro-4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol
—— 3-[6-Cyclohexyl-2-[(dimethylamino)methyl]cyclohepten-1-yl]phenol —— C22H33NO
3-[6-Cyclohexyl-2-[(dimethylamino)methyl]cyclohepten-1-yl]phenol
—— 2-dimethylaminoethyl-5-(3-hydroxy-4-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one 519015-00-0 C16H23N3O3S
2-dimethylaminoethyl-5-(3-hydroxy-4-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one
—— (E,E)-2-acetaminocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile 368836-85-5 C14H14N2O4
(E,E)-2-acetaminocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile
—— 2-(2-hydroxy-5-nitrobenzyl)-5-methoxy-1-(4-trifluoro-methoxybenzenesulphonyl)-1,2-dihydroindazol-3-one —— C22H16F3N3O8S
2-(2-hydroxy-5-nitrobenzyl)-5-methoxy-1-(4-trifluoro-methoxybenzenesulphonyl)-1,2-dihydroindazol-3-one
—— N-(4-[2-(2-hydroxy-5-nitrobenzyl)-5-methoxy-3-oxo-2,3-dihydroindazol-1-sulphonyl]phenyl)acetamide —— C23H20N4O8S
N-(4-[2-(2-hydroxy-5-nitrobenzyl)-5-methoxy-3-oxo-2,3-dihydroindazol-1-sulphonyl]phenyl)acetamide
—— (Z,2S)-2-(4-hydroxy-3-methoxyphenyl)icos-11-enamide —— C27H45NO3
(Z,2S)-2-(4-hydroxy-3-methoxyphenyl)icos-11-enamide
—— 4-[4-[(Dimethylamino)methyl]-3-(3-hydroxyphenyl)cyclohept-3-en-1-yl]-2,6-dimethylphenol —— C24H31NO2
4-[4-[(Dimethylamino)methyl]-3-(3-hydroxyphenyl)cyclohept-3-en-1-yl]-2,6-dimethylphenol