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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-(4-hydroxybenzylidene)-N-(3-hydroxyphenyl)hydrazine-1-carbothioamide 1097214-22-6 C14H13N3O2S
2-(4-hydroxybenzylidene)-N-(3-hydroxyphenyl)hydrazine-1-carbothioamide
—— 2-(2,6-Dihydroxy-3-pyridylazo)-phenol 21269-89-6 C11H9N3O3
2-(2,6-Dihydroxy-3-pyridylazo)-phenol
—— 4-(2,2-Dichloro-cyclopropyl)-2-nitro-phenol 74387-10-3 C9H7Cl2NO3
4-(2,2-Dichloro-cyclopropyl)-2-nitro-phenol
—— 2,6-dicyclopentyl-4-methylphenol 41505-40-2 C17H24O
2,6-dicyclopentyl-4-methylphenol
—— (RS)-1-(2-azido-propyl)-7-hydroxy-1,4-dihydro-indeno[1,2-b]pyrrole 170495-90-6 C14H14N4O
(RS)-1-(2-azido-propyl)-7-hydroxy-1,4-dihydro-indeno[1,2-b]pyrrole
—— 1-(3,5-dibromo-4-hydroxyphenyl)-5-bromodihydrouracil 83809-78-3 C10H7Br3N2O3
1-(3,5-dibromo-4-hydroxyphenyl)-5-bromodihydrouracil
—— 3-bromo-2,5-dimethoxyphenol 202735-34-0 C8H9BrO3
3-bromo-2,5-dimethoxyphenol
—— 2-{4,5-dimethoxy-2-[(triisopropylsilanyl)ethynyl]phenyl}ethanol 863324-10-1 C21H34O3Si
2-{4,5-dimethoxy-2-[(triisopropylsilanyl)ethynyl]phenyl}ethanol
—— 2,2,3,3,4,4,4-Heptafluoro-N-(2,2,3,3,4,4,4-heptafluorobutanoyl)-N-[2-(3-hydroxy-4-methoxyphenyl)ethyl]butanamide 55429-09-9 C17H11F14NO4
2,2,3,3,4,4,4-Heptafluoro-N-(2,2,3,3,4,4,4-heptafluorobutanoyl)-N-[2-(3-hydroxy-4-methoxyphenyl)ethyl]butanamide
—— 2-(2-aminoethyl)-5-nitrohydroquinone 41241-39-8 C8H10N2O4
2-(2-aminoethyl)-5-nitrohydroquinone
—— 2-fluoro-5-((triisopropylsilyl)ethynyl)phenol 1065167-92-1 C17H25FOSi
2-fluoro-5-((triisopropylsilyl)ethynyl)phenol
—— 1-(3,5-dibromo-4-hydroxyphenyl)-5,5-dibromodihydrouracil 83809-80-7 C10H6Br4N2O3
1-(3,5-dibromo-4-hydroxyphenyl)-5,5-dibromodihydrouracil
—— 1-(2-formyl-5-methyl-3-thienyl)-2-(4-hydroxy-2,6-dimethylphenyl)-3,3,4,4,5,5-hexafluorocyclopentene 1607796-27-9 C19H14F6O2S
1-(2-formyl-5-methyl-3-thienyl)-2-(4-hydroxy-2,6-dimethylphenyl)-3,3,4,4,5,5-hexafluorocyclopentene
—— 4-Bromo-5-(chloromethyl)-2-methoxyphenol 655238-40-7 C8H8BrClO2
4-Bromo-5-(chloromethyl)-2-methoxyphenol
—— methyl 2-(4-hydroxyphenyl)acetate 208644-94-4 C9H10O3
methyl 2-(4-hydroxyphenyl)acetate
—— 2-(4-hydroxyphenyl)acetic acid 208644-93-3 C8H8O3
2-(4-hydroxyphenyl)acetic acid
—— Phenol, 2-[[(4-bromophenyl)imino]methyl]-4-methyl- 106038-85-1 C14H12BrNO
Phenol, 2-[[(4-bromophenyl)imino]methyl]-4-methyl-
—— 2,6-Dichlor-3,5-dicyanhydrochinon 85979-36-8 C8H2Cl2N2O2
2,6-Dichlor-3,5-dicyanhydrochinon
—— 3-(4-hydroxy-3-methoxy-phenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole 1252008-13-1 C19H22N2O5
3-(4-hydroxy-3-methoxy-phenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
—— 1-acetyl-3-(4-hydroxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole 1252008-24-4 C21H24N2O6
1-acetyl-3-(4-hydroxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
—— methyl-2-([2-(2-hydroxyphenyl)ethylidynenitrilo]ethyl)amino-1-cyclopentenedithiocarboxylate 1234511-16-0 C17H22N2OS2
methyl-2-([2-(2-hydroxyphenyl)ethylidynenitrilo]ethyl)amino-1-cyclopentenedithiocarboxylate
—— methyl-2-([2-(2-hydroxy-5-nitro-phenyl)methylidynenitrilo]ethyl)amino-1-cyclopentenedithiocarboxylate 1234511-15-9 C16H19N3O3S2
methyl-2-([2-(2-hydroxy-5-nitro-phenyl)methylidynenitrilo]ethyl)amino-1-cyclopentenedithiocarboxylate
—— 5-(3-hydroxyphenyl)thiophene-2-carbaldehyde 893740-93-7 C11H8O2S
5-(3-hydroxyphenyl)thiophene-2-carbaldehyde
—— 4-hydroxy-3-methoxy-benzaldehyde 4-furfuryl-thiosemicarbazone 27031-94-3 C14H15N3O3S
4-hydroxy-3-methoxy-benzaldehyde 4-furfuryl-thiosemicarbazone
—— 2-[(2-methylphenylimino)methyl]-4-nitrophenol 119740-58-8 C14H12N2O3
2-[(2-methylphenylimino)methyl]-4-nitrophenol
—— 2-[(3,5-Dimethyl-1,2,4-triazol-4-yl)iminomethyl]phenol 185130-02-3 C11H12N4O
2-[(3,5-Dimethyl-1,2,4-triazol-4-yl)iminomethyl]phenol
—— 4-methoxyphenethyl chloromethyl ether 215252-00-9 C10H13ClO2
4-methoxyphenethyl chloromethyl ether
—— 4-Bromo-2-[(3,5-dimethyl-1,2,4-triazol-4-yl)iminomethyl]phenol 304907-55-9 C11H11BrN4O
4-Bromo-2-[(3,5-dimethyl-1,2,4-triazol-4-yl)iminomethyl]phenol
—— 4-hydroxy-3-methoxybenzaldehyde picoloylhydrazone 6434-07-7 C14H13N3O3
4-hydroxy-3-methoxybenzaldehyde picoloylhydrazone
—— 3-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-dihydro-furan-2-one 58165-19-8 C11H10O3
3-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-dihydro-furan-2-one
—— 2-bromo-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-5-methoxybenzamide 1372167-70-8 C18H17BrN2O5S
2-bromo-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-5-methoxybenzamide
—— 2-bromo-N'-[(1Z)-(4-hydroxy-3-methoxyphenyl)methylene]-5-methoxybenzohydrazide 1372167-86-6 C16H15BrN2O4
2-bromo-N'-[(1Z)-(4-hydroxy-3-methoxyphenyl)methylene]-5-methoxybenzohydrazide
—— 4-((phenylimino)methyl)benzene-1,2-diol 93445-12-6 C13H11NO2
4-((phenylimino)methyl)benzene-1,2-diol
—— 1,3-Benzenediol, 4-[[(2,4-dimethylphenyl)imino]methyl]- 141875-36-7 C15H15NO2
1,3-Benzenediol, 4-[[(2,4-dimethylphenyl)imino]methyl]-
—— 1400584-04-4 C20H20N2O2S
—— 1400583-97-2 C20H20N2O2S
—— 4-bromo-2,3,6-trifluorophenol 192446-70-1 C6H2BrF3O
4-bromo-2,3,6-trifluorophenol
—— 4-Chloro-2-{1-[(E)-p-tolylimino]-ethyl}-phenol 105533-44-6 C15H14ClNO
4-Chloro-2-{1-[(E)-p-tolylimino]-ethyl}-phenol
—— Cambridge id 5429409 416896-93-0 C13H22N2O2
Cambridge id 5429409
—— syn-4-hydroxy-N,N-diisopropyl-5-triethylsilyl-2-[2.2]paracyclophanecarboxamide 360049-45-2 C29H43NO2Si
syn-4-hydroxy-N,N-diisopropyl-5-triethylsilyl-2-[2.2]paracyclophanecarboxamide
—— 4-chloro-2-{(E)-[(3-chlorophenyl)imino]methyl}phenol 5278-80-8 C13H9Cl2NO
4-chloro-2-{(E)-[(3-chlorophenyl)imino]methyl}phenol
—— 5-hydroxy-4-methoxymethyleneoxy[2.2]paracyclophane 588717-64-0 C18H20O3
5-hydroxy-4-methoxymethyleneoxy[2.2]paracyclophane
—— 2-bromo-4-t-butyl-6-methoxyphenol 21237-43-4 C11H15BrO2
2-bromo-4-t-butyl-6-methoxyphenol
—— 7-hydroxy[2.2]paracyclophane-4-carbaldehyde 874566-75-3 C17H16O2
7-hydroxy[2.2]paracyclophane-4-carbaldehyde
—— 4-((2-Hydroxy-5-nitro-benzylidene)-amino)-benzonitrile 5265-04-3 C14H9N3O3
4-((2-Hydroxy-5-nitro-benzylidene)-amino)-benzonitrile
—— 3-bromo-N'-(4-hydroxy-3-methoxybenzylidene)benzohydrazide 300358-17-2 C15H13BrN2O3
3-bromo-N'-(4-hydroxy-3-methoxybenzylidene)benzohydrazide
—— 5-Methyl-2-[(2-methylbenzylidene)amino]phenol 303761-91-3 C15H15NO
5-Methyl-2-[(2-methylbenzylidene)amino]phenol
—— 3-[(2-Hydroxy-5-nitrobenzylidene)amino]benzamide 5322-30-5 C14H11N3O4
3-[(2-Hydroxy-5-nitrobenzylidene)amino]benzamide
—— 2,6-Dimethyl-α,α-bis-(trifluormethyl)-p-kresol 16867-77-9 C11H10F6O
2,6-Dimethyl-α,α-bis-(trifluormethyl)-p-kresol
—— 1-bromo-2,5-dihydroxy-4-nitrobenzene 151252-61-8 C6H4BrNO4
1-bromo-2,5-dihydroxy-4-nitrobenzene