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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
—— 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-chloro-6-methoxyphenol 1321513-87-4 C16H13ClN4O2
4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-chloro-6-methoxyphenol
—— 3-[4]pyridyl-propionic acid-(4-hydroxy-benzylidenehydrazide) 101091-58-1 C15H15N3O2
3-[4]pyridyl-propionic acid-(4-hydroxy-benzylidenehydrazide)
—— 2-{[(E)-3-(1-Hydroxy-ethyl)-phenylimino]-methyl}-4,6-diiodo-phenol 20099-20-1 C15H13I2NO2
2-{[(E)-3-(1-Hydroxy-ethyl)-phenylimino]-methyl}-4,6-diiodo-phenol
—— 6-Hydroxy-2,3,4-trimethyl-benzaldehyd-oxim 91012-33-8 C10H13NO2
6-Hydroxy-2,3,4-trimethyl-benzaldehyd-oxim
—— 5,8-Dimethyl-2,4-dinitro-5,6,7,8-tetrahydro-naphthalen-1-ol 41059-20-5 C12H14N2O5
5,8-Dimethyl-2,4-dinitro-5,6,7,8-tetrahydro-naphthalen-1-ol
—— 2-Bromo-4-(phenyliminomethyl)phenol 897754-18-6 C13H10BrNO
2-Bromo-4-(phenyliminomethyl)phenol
—— N'-hydroxy-4-(4-hydroxyphenyl)-3-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboximidamide 1360604-96-1 C15H14N4O2S
N'-hydroxy-4-(4-hydroxyphenyl)-3-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboximidamide
—— 2-(2,2-dichlorovinyl)-4-fluorophenol 91703-50-3 C8H5Cl2FO
2-(2,2-dichlorovinyl)-4-fluorophenol
—— 5,5-dimethylcyclohexane-2-(2'-hydroxyphenyl)hydrazono-1,3-dione 16623-42-0 C14H16N2O3
5,5-dimethylcyclohexane-2-(2'-hydroxyphenyl)hydrazono-1,3-dione
—— 3-(4-Ethylthiophen-2-yl)-5-methylphenol 1261977-51-8 C13H14OS
3-(4-Ethylthiophen-2-yl)-5-methylphenol
—— 5-Phenyl-4-<2-hydroxy-phenyl>-isoxazol 92497-79-5 C15H11NO2
5-Phenyl-4-<2-hydroxy-phenyl>-isoxazol
—— zinc(II) (2-aminoethyl)(5-nitro-2-oxidobenzoyl)amide hydrate 1196131-94-8 C9H9N3O4*H2O*Zn
zinc(II) (2-aminoethyl)(5-nitro-2-oxidobenzoyl)amide hydrate
—— 123385-73-9 C26H24N4NiO6
—— bis(o-vanillin) S-methylisothiosemicarbazone 1561173-95-2 C18H19N3O4S
bis(o-vanillin) S-methylisothiosemicarbazone
—— 2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-hept-2-en-6-ynyl)-phenol 403696-87-7 C22H28O3
2-((E)-(S)-1-Hydroxy-3-methyl-hexa-2,5-dienyl)-4-methoxy-5-((Z)-2-methyl-hept-2-en-6-ynyl)-phenol
—— ethyl 2-(4,5-dimethoxy-2-hydroxyphenyl)-4-(furan-2-yl)-4-oxobutanoate 1416565-87-1 C18H20O7
ethyl 2-(4,5-dimethoxy-2-hydroxyphenyl)-4-(furan-2-yl)-4-oxobutanoate
—— 1394125-00-8 C19H15N3O2
—— H2cd5OMesalpd 1239496-50-4 C18H24N2O2S2
H2cd5OMesalpd
—— 2-Methyl-4-(4-methylisoxazol-5-yl)phenol 1399653-23-6 C11H11NO2
2-Methyl-4-(4-methylisoxazol-5-yl)phenol
—— 4-{[6-Bromo-7-methyl-2,3-dihydro-1H-[1,8]naphthyridin-(4E)-ylidene]-hydrazonomethyl}-2-methoxy-phenol 82070-81-3 C17H17BrN4O2
4-{[6-Bromo-7-methyl-2,3-dihydro-1H-[1,8]naphthyridin-(4E)-ylidene]-hydrazonomethyl}-2-methoxy-phenol
—— Dimer von 4-Isopropenyl-phenol 94265-09-5 C18H22O2
Dimer von 4-Isopropenyl-phenol
—— 3-[2-(tert-Butyl-methyl-amino)-1-hydroxy-ethyl]-phenol 14185-33-2 C13H21NO2
3-[2-(tert-Butyl-methyl-amino)-1-hydroxy-ethyl]-phenol
—— 2-[[3-[(2-Hydroxy-3,5-dinitrophenyl)methylideneamino]-2,4,6-tri(propan-2-yl)phenyl]iminomethyl]-4,6-dinitrophenol 927895-02-1 C29H30N6O10
2-[[3-[(2-Hydroxy-3,5-dinitrophenyl)methylideneamino]-2,4,6-tri(propan-2-yl)phenyl]iminomethyl]-4,6-dinitrophenol
—— (Z)-diethyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-vinylphosphonate 407583-16-8 C18H24N3O6P
(Z)-diethyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-vinylphosphonate
—— 8-(2-hydroxyphenyl)-1,5-diazabicyclo[3.2.1]octane 116865-23-7 C12H16N2O
8-(2-hydroxyphenyl)-1,5-diazabicyclo[3.2.1]octane
—— (2-hydroxyphenyl)diisopropylphosphine oxide 129529-23-3 C12H19O2P
(2-hydroxyphenyl)diisopropylphosphine oxide
—— homovanillyl 7-methyloctanoate 951221-78-6 C18H28O4
homovanillyl 7-methyloctanoate
—— N-cyclohexyl-5-(4-hydroxy-3-methoxybenzylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide 1224941-04-1 C21H25N5O3
N-cyclohexyl-5-(4-hydroxy-3-methoxybenzylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide
—— 6-amino-7-(1H-benzo[d]imidazol-2-yl)-5-(3-hydroxy-4-methoxybenzyl)-5H-pyrrolo[3,2-b]pyrazine-2,3-dicarbonitrile 1620085-95-1 C23H16N8O2
6-amino-7-(1H-benzo[d]imidazol-2-yl)-5-(3-hydroxy-4-methoxybenzyl)-5H-pyrrolo[3,2-b]pyrazine-2,3-dicarbonitrile
—— 3-(4-hydroxy-phenyl)-2-thiazol-2-yl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104633-81-9 C17H15NO2S
3-(4-hydroxy-phenyl)-2-thiazol-2-yl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— (R)-6,6'-((1E,1'E)-((1S,2S)-cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(3,5-dibromo-2-(((S)-1-phenylethyl)amino)phenol) 1582779-33-6 C36H36Br4N4O2
(R)-6,6'-((1E,1'E)-((1S,2S)-cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(3,5-dibromo-2-(((S)-1-phenylethyl)amino)phenol)
—— 945842-39-7 C26H22N4O6
—— 3,4-dimethoxy-phenethylamine; picrate 14456-33-8 C6H3N3O7*C10H15NO2
3,4-dimethoxy-phenethylamine; picrate
—— 2-acetamido-2-(4-hydroxyphenethyl)-propane-1,3-diyl diacetate 162360-77-2 C17H23NO6
2-acetamido-2-(4-hydroxyphenethyl)-propane-1,3-diyl diacetate
—— 4-(Chloromethyl)-2-methyl-6-nitrophenol 40638-49-1 C8H8ClNO3
4-(Chloromethyl)-2-methyl-6-nitrophenol
—— 2-Chloro-5-(4-ethylthiophen-2-yl)phenol 1261972-23-9 C12H11ClOS
2-Chloro-5-(4-ethylthiophen-2-yl)phenol
—— 6-(5-chloro-2-hydroxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one 62902-82-3 C10H9ClN2O2
6-(5-chloro-2-hydroxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— N-(p-hydroxybenzylidene)aniline 40339-41-1 C13H11NO
N-(p-hydroxybenzylidene)aniline
—— 2-bromo-4,5-dimethoxy-6-methyl-3-(4-methyl-2,4-pentadienyl)phenol 109034-97-1 C15H19BrO3
2-bromo-4,5-dimethoxy-6-methyl-3-(4-methyl-2,4-pentadienyl)phenol
—— 4-(2-thiazolylazo)resorcinol 101515-17-7 C21H31N3O2S
4-(2-thiazolylazo)resorcinol
—— 5-Nitro-2-hydroxy-benzal-methylbutylhydrazin 1617-61-4 C12H17N3O3
5-Nitro-2-hydroxy-benzal-methylbutylhydrazin
—— 4-[4-(Oxetan-3-yloxy)-butoxy]-phenol 202983-48-0 C13H18O4
4-[4-(Oxetan-3-yloxy)-butoxy]-phenol
—— 2,6-Bis[(3-chlorophenyl)iminomethyl]-4-methylphenol 213403-71-5 C21H16Cl2N2O
2,6-Bis[(3-chlorophenyl)iminomethyl]-4-methylphenol
—— 2-(5-pyridin-2-yl-isoxazol-3-yl)-phenol 54209-93-7 C14H10N2O2
2-(5-pyridin-2-yl-isoxazol-3-yl)-phenol
—— Endosidin2 1839524-44-5 C15H12FIN2O3
Endosidin2
—— 2-<2-Hydroxy-benzyl>-1-semicarbazono-cyclohexan 24195-35-5 C14H19N3O2
2-<2-Hydroxy-benzyl>-1-semicarbazono-cyclohexan
—— 2-[(Z)-1-(4-hydroxyphenyl)ethylideneamino]guanidine;nitric acid 13308-97-9 C9H13N5O4
2-[(Z)-1-(4-hydroxyphenyl)ethylideneamino]guanidine;nitric acid
—— 2-(1-hydroxyallyl)-6-methoxyphenol 1429628-97-6 C10H12O3
2-(1-hydroxyallyl)-6-methoxyphenol
—— 4-<1-aethyl-cyclohexyl>-o-kresol 6800-86-8 C15H22O
4-<1-aethyl-cyclohexyl>-o-kresol
—— 3-[4]pyridyl-propionic acid vanillylidenehydrazide 107057-07-8 C16H17N3O3
3-[4]pyridyl-propionic acid vanillylidenehydrazide