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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
—— 2-Methoxy-6-methylsulfanyl-benzene-1,4-diol 139553-43-8 C8H10O3S
2-Methoxy-6-methylsulfanyl-benzene-1,4-diol
—— 2-fluoro-4,6-diiodo-phenol 767-82-8 C6H3FI2O
2-fluoro-4,6-diiodo-phenol
—— 14-C-labelled p-coumaric acid 4120-62-1 C9H8O3
14-C-labelled p-coumaric acid
—— 2-(2-hydroxy-3-methoxybenzylidene)-N-methylhydrazine-1-carboxamide 1231766-71-4 C10H13N3O3
2-(2-hydroxy-3-methoxybenzylidene)-N-methylhydrazine-1-carboxamide
—— (S)-methyl 4-(4-fluorophenyl)-6-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate 1332624-47-1 C13H13FO4
(S)-methyl 4-(4-fluorophenyl)-6-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
—— N''-[1-(2-hydroxy-5-methylphenyl)ethylidene]-N'''-[1-(2-hydroxy-5-methyl-3-nitrophenyl)ethylidene]carnonohydrazide 1402135-57-2 C19H21N5O5
N''-[1-(2-hydroxy-5-methylphenyl)ethylidene]-N'''-[1-(2-hydroxy-5-methyl-3-nitrophenyl)ethylidene]carnonohydrazide
—— 4-(3-chloro-4-hydroxyphenyl)-1,4-dihydro-2-methyl-6-phenyl-3,5-pyridinedicarbonitrile 1033770-24-9 C20H14ClN3O
4-(3-chloro-4-hydroxyphenyl)-1,4-dihydro-2-methyl-6-phenyl-3,5-pyridinedicarbonitrile
—— Vanillinsaeure-<N-hydroxy-methyl-amid> 6043-62-5 C9H11NO4
Vanillinsaeure-<N-hydroxy-methyl-amid>
—— N-(3-(2-hydroxy-5-methylphenyl)propyl)methanesulfonamide 1261034-03-0 C11H17NO3S
N-(3-(2-hydroxy-5-methylphenyl)propyl)methanesulfonamide
—— 1-(2-hydroxy-phenyl)-4-methyl-pent-2-yne-1,4-diol 100117-69-9 C12H14O3
1-(2-hydroxy-phenyl)-4-methyl-pent-2-yne-1,4-diol
—— Ethyl 2-cyano-3-(3,4-dihydroxyphenyl)propanoate 132464-99-4 C12H13NO4
Ethyl 2-cyano-3-(3,4-dihydroxyphenyl)propanoate
—— 4,7-dihydro-4-(4-hydroxybenzylidene)-3,5-dimethyl-7-oxo-1H-1,2-diazepine-6-carbonitrile 127382-00-7 C15H13N3O2
4,7-dihydro-4-(4-hydroxybenzylidene)-3,5-dimethyl-7-oxo-1H-1,2-diazepine-6-carbonitrile
—— 1-(2-Hydroxy-phenyl)-2,2-dimethyl-propane-1,3-diol 91352-60-2 C11H16O3
1-(2-Hydroxy-phenyl)-2,2-dimethyl-propane-1,3-diol
—— (2α,5aα,6β,11β,11aα)-2-acetyl-6,11-diacetoxy-1,2,3,4,5a,6,11,11a,12-decahydronaphthacene 82167-67-7 C24H28O5
(2α,5aα,6β,11β,11aα)-2-acetyl-6,11-diacetoxy-1,2,3,4,5a,6,11,11a,12-decahydronaphthacene
—— 3-[5-chloro-2-[2-(4-methoxy-phenyl)-ethoxy]-phenoxy]-azetidine 1227621-35-3 C18H20ClNO3
3-[5-chloro-2-[2-(4-methoxy-phenyl)-ethoxy]-phenoxy]-azetidine
—— 2-(4,6-bis-octylsulfanyl-[1,3,5]triazin-2-ylamino)-4-methyl-phenol 1258-78-2 C26H42N4OS2
2-(4,6-bis-octylsulfanyl-[1,3,5]triazin-2-ylamino)-4-methyl-phenol
—— 7-methoxymethyl-5-methyl-4-indanol 1089665-67-7 C12H16O2
7-methoxymethyl-5-methyl-4-indanol
—— 3,3'-((1E,1'E)-(((1R,2S)-1,2-bis(2-hydroxyphenyl)ethane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(benzene-1,2-diol) 1217898-14-0 C28H24N2O6
3,3'-((1E,1'E)-(((1R,2S)-1,2-bis(2-hydroxyphenyl)ethane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(benzene-1,2-diol)
—— 2-(Chloromethyl)-5-methoxyphenol 529502-40-7 C8H9ClO2
2-(Chloromethyl)-5-methoxyphenol
—— (((4-(2-ethoxyethyl)-1,2-phenylene)bis(oxy))bis(methylene))dibenzene 1191117-27-7 C24H26O3
(((4-(2-ethoxyethyl)-1,2-phenylene)bis(oxy))bis(methylene))dibenzene
—— (2-14C)Tyramin 13171-11-4 C8H11NO
(2-14C)Tyramin
—— α-<p-Hydroxy-phenylimino>-<pyridyl-(3)>-acetonitril 21553-29-7 C13H9N3O
α-<p-Hydroxy-phenylimino>-<pyridyl-(3)>-acetonitril
—— N-(5-methyl-2-hydroxyphenyl)-2,4-dimethoxybenzaldimine 77491-06-6 C16H17NO3
N-(5-methyl-2-hydroxyphenyl)-2,4-dimethoxybenzaldimine
—— 3-bromo-4-hydroxy-thiobenzamide 25984-64-9 C7H6BrNOS
3-bromo-4-hydroxy-thiobenzamide
—— 5-Nitro-2-hydroxy-benzal-methylallylhydrazin 91332-49-9 C11H13N3O3
5-Nitro-2-hydroxy-benzal-methylallylhydrazin
—— 5,5'-bis-(2-hydroxy-3,5-dimethyl-benzyl)-octahydro-3,3'-methanediyl-bis-[1,3,5]oxadiazin-4-one 114280-20-5 C25H32N4O6
5,5'-bis-(2-hydroxy-3,5-dimethyl-benzyl)-octahydro-3,3'-methanediyl-bis-[1,3,5]oxadiazin-4-one
—— diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate 188357-92-8 C19H22O6
diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate
—— 2-butyl-4-fluoro-phenol 325-86-0 C10H13FO
2-butyl-4-fluoro-phenol
—— 6-(3-methoxyl-4-hydroxybenzyl)-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one 1529781-55-2 C19H15N3O4S
6-(3-methoxyl-4-hydroxybenzyl)-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one
—— 3,19-Dihydroxy-9,10-seco-androsta-1,3,5(10)-trien-9,17-dion 1944-48-5 C19H24O4
3,19-Dihydroxy-9,10-seco-androsta-1,3,5(10)-trien-9,17-dion
—— (5-Hydroxy-2-nitro-benzyl)-diicosyl-methyl-ammonium; bromide 128971-02-8 Br*C48H91N2O3
(5-Hydroxy-2-nitro-benzyl)-diicosyl-methyl-ammonium; bromide
—— 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(1-hydroxy-cyclopentylethynyl)-6-methoxy-phenol 343309-55-7 C21H32O4Si
4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(1-hydroxy-cyclopentylethynyl)-6-methoxy-phenol
—— 153245-60-4 C13H18CuN4O5
—— 2-Methyl-6-(1-methyl-heptyl)-phenol 40211-08-3 C15H24O
2-Methyl-6-(1-methyl-heptyl)-phenol
—— 4-Tetradecyl-6-nitroso-resorcin 1892-45-1 C20H33NO3
4-Tetradecyl-6-nitroso-resorcin
—— 3,4-dihydroxybenzoyl cyanide 857369-24-5 C8H5NO3
3,4-dihydroxybenzoyl cyanide
—— 4-<3-methyl-buten-(2)-yl>-m-kresol 879-77-6 C12H16O
4-<3-methyl-buten-(2)-yl>-m-kresol
—— 3-(3,4-Dihydroxy-phenyl)-2-pyridin-2-yl-thiopropionamide 35583-56-3 C14H14N2O2S
3-(3,4-Dihydroxy-phenyl)-2-pyridin-2-yl-thiopropionamide
—— 3-Methoxy-4-hydroxy-benzaldehyd-<4-oxo-3-o-tolyl-5-phenyl-thiazolin-2-yl-hydrazon> 913-65-5 C24H21N3O3S
3-Methoxy-4-hydroxy-benzaldehyd-<4-oxo-3-o-tolyl-5-phenyl-thiazolin-2-yl-hydrazon>
—— 4-hydroxy-3,5-diiodo-benzamidine 2315-75-5 C7H6I2N2O
4-hydroxy-3,5-diiodo-benzamidine
—— 2-(4-Hydroxy-3-methoxybenzylidenhydrazono)-4-oxo-5-phenyl-3-p-tolyl-thiazolidin 101656-62-6 C24H21N3O3S
2-(4-Hydroxy-3-methoxybenzylidenhydrazono)-4-oxo-5-phenyl-3-p-tolyl-thiazolidin
—— 1310796-58-7 C19H24N2O4
—— 2(3,5-Dibrom-2-hydroxybenzylidenamino)-2-methyl-propan-1-ol 5067-36-7 C11H13Br2NO2
2(3,5-Dibrom-2-hydroxybenzylidenamino)-2-methyl-propan-1-ol
—— (5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(4-tetrahydro-furan-2-yl-butyryl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-13-4 C41H57N3O9Si
(5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(4-tetrahydro-furan-2-yl-butyryl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— 2-Palmitoylamino-5-nitrophenol 29338-07-6 C22H36N2O4
2-Palmitoylamino-5-nitrophenol
—— 2-Azido-6-methoxyphenol 1268445-25-5 C7H7N3O2
2-Azido-6-methoxyphenol
—— 2-Bromo-3,6-dimethyl-4-nitro-phenol 72373-75-2 C8H8BrNO3
2-Bromo-3,6-dimethyl-4-nitro-phenol
—— 4-(2-chloroethyl)-2-iodophenol 1243680-57-0 C8H8ClIO
4-(2-chloroethyl)-2-iodophenol
—— (5R)-(E)-epi-epicoccarine A 1401427-76-6 C23H31NO4
(5R)-(E)-epi-epicoccarine A
—— 2-(2-fluoro-4-hydroxyphenyl)-1-morpholin-4-ylethanethione 1204310-38-2 C12H14FNO2S
2-(2-fluoro-4-hydroxyphenyl)-1-morpholin-4-ylethanethione