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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
—— (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester 477980-80-6 C12H15ClO4
(S)-3-(3-Chloro-4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester
—— 2-Methyl-adrenalin 2887-78-7 C10H15NO3
2-Methyl-adrenalin
—— 2-Chlor-3,5-dihydroxybenzylalkohol 35354-28-0 C7H7ClO3
2-Chlor-3,5-dihydroxybenzylalkohol
—— 1,4-dihydro-2,6-dimethyl-4-(3',5'-dimethoxy-4'-hydroxyphenyl)-3,5-pyridinedicarboxylic acid, methyl ethyl ester 161187-64-0 C20H25NO7
1,4-dihydro-2,6-dimethyl-4-(3',5'-dimethoxy-4'-hydroxyphenyl)-3,5-pyridinedicarboxylic acid, methyl ethyl ester
—— 2-(N-hydroxy-C-methylcarbonimidoyl)-4-octylphenol 74604-09-4 C16H25NO2
2-(N-hydroxy-C-methylcarbonimidoyl)-4-octylphenol
—— 2-Allyl-5-ethoxy-4-methoxyphenol 522598-84-1 C12H16O3
2-Allyl-5-ethoxy-4-methoxyphenol
—— 3,5-dimethoxy-4-hydroxy-benzyl 2'-methoxy-4'-hydroxymethyl-phenyl ether 55525-43-4 C17H20O6
3,5-dimethoxy-4-hydroxy-benzyl 2'-methoxy-4'-hydroxymethyl-phenyl ether
—— 3-methoxy-2,5,6-trimethylphenol 34883-03-9 C10H14O2
3-methoxy-2,5,6-trimethylphenol
—— 3-(o-Hydroxyphenyl)-5-methylisoxazol 70423-62-0 C10H9NO2
3-(o-Hydroxyphenyl)-5-methylisoxazol
—— 2-(2-Hydroxy-5-methoxy-3-methylphenyl)-2-propanol 38102-59-9 C11H16O3
2-(2-Hydroxy-5-methoxy-3-methylphenyl)-2-propanol
—— 2-((tert-butyldimethylsilyl)methyl)phenol 1417315-92-4 C13H22OSi
2-((tert-butyldimethylsilyl)methyl)phenol
—— 3-Dodecyl-brenzcatechin 7573-08-2 C18H30O2
3-Dodecyl-brenzcatechin
—— 3-Cyclohexylidene-5-(4-hydroxy-phenyl)-3H-furan-2-one 959251-52-6 C16H16O3
3-Cyclohexylidene-5-(4-hydroxy-phenyl)-3H-furan-2-one
—— 2-(3',5'-Dihydroxyphenyl)-2-hydroxyethylamin 46049-55-2 C8H11NO3
2-(3',5'-Dihydroxyphenyl)-2-hydroxyethylamin
—— 3-Methyl-2-hydroxy-acetophenonimin 54758-47-3 C9H11NO
3-Methyl-2-hydroxy-acetophenonimin
—— 6-(2-Hydroxy-phenyl)-4,6-dimethyl-5-oxo-cyclohexa-1,3-dienecarboxylic acid methyl ester 40801-43-2 C16H16O4
6-(2-Hydroxy-phenyl)-4,6-dimethyl-5-oxo-cyclohexa-1,3-dienecarboxylic acid methyl ester
—— 4-(3-pyridylazo)resorcinol 16566-56-6 C11H9N3O2
4-(3-pyridylazo)resorcinol
—— salicylaldehydemethanesulfonylhydrazone 263009-12-7 C8H10N2O3S
salicylaldehydemethanesulfonylhydrazone
—— 2-(4-hydroxybenzylidene)-N-(2-hydroxyphenyl)hydrazine-1-carbothioamide 1097214-21-5 C14H13N3O2S
2-(4-hydroxybenzylidene)-N-(2-hydroxyphenyl)hydrazine-1-carbothioamide
—— piperidin-1-yl-[4-(hydroxy)phenyl]methanethione 58563-55-6 C12H15NOS
piperidin-1-yl-[4-(hydroxy)phenyl]methanethione
—— 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