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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-(2-Hydroxy-5-nitro-phenyl)-6-(4-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 40188-98-5 C22H21NO7
4-(2-Hydroxy-5-nitro-phenyl)-6-(4-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
—— 3-(2,5-Dichloro-3,6-dihydroxy-phenyl)-pentane-2,4-dione 93645-28-4 C11H10Cl2O4
3-(2,5-Dichloro-3,6-dihydroxy-phenyl)-pentane-2,4-dione
—— 4-(Pentafluorchlor-2-hydroxy-2-propyl)-phenol 2093-09-6 C9H6ClF5O2
4-(Pentafluorchlor-2-hydroxy-2-propyl)-phenol
—— 41350-40-7 C20H16N2O2S2
—— 2,6-Dimethyl-4-(trifluoromethoxy)phenol 1262415-43-9 C9H9F3O2
2,6-Dimethyl-4-(trifluoromethoxy)phenol
—— 2-(1-(1-methyl-1H-pyrrol-2-yl)ethyl)phenol 1295507-40-2 C13H15NO
2-(1-(1-methyl-1H-pyrrol-2-yl)ethyl)phenol
—— 181932-38-7 C14H12BrN3O3
—— 92550-89-5 C15H15BrN2O2
—— 2,2'-(2-methyl-2-(pyridin-2-yl)propane-1,3-diyl)bis(azanediyl)bis(methylene)bis(4-nitrophenol) 1345342-23-5 C23H25N5O6
2,2'-(2-methyl-2-(pyridin-2-yl)propane-1,3-diyl)bis(azanediyl)bis(methylene)bis(4-nitrophenol)
—— Glyoxal-bis-<2-hydroxy-4-methyl-anil> 37841-70-6 C16H16N2O2
Glyoxal-bis-<2-hydroxy-4-methyl-anil>
—— 2-(β-Hydroxyethylamino)-4.6-bis-(2.4-dihydroxyphenyl)-1.3.5-triazin 1853-78-7 C19H20N4O6
2-(β-Hydroxyethylamino)-4.6-bis-(2.4-dihydroxyphenyl)-1.3.5-triazin
—— 4,N-dihydroxy-3-methoxy-5-methyl-benzamidine 1011264-23-5 C9H12N2O3
4,N-dihydroxy-3-methoxy-5-methyl-benzamidine
—— 2-(4-hydroxy-benzylideneamino)butyramide 1412763-20-2 C11H14N2O2
2-(4-hydroxy-benzylideneamino)butyramide
—— 2,2-Dimethyl-propionic acid 3-hydroxy-2-(4-hydroxy-phenyl)-propyl ester 881672-56-6 C14H20O4
2,2-Dimethyl-propionic acid 3-hydroxy-2-(4-hydroxy-phenyl)-propyl ester
—— Acetic acid (E)-6-(2-hydroxy-4,5-dimethoxy-phenyl)-2-methyl-hept-2-enyl ester 118343-53-6 C18H26O5
Acetic acid (E)-6-(2-hydroxy-4,5-dimethoxy-phenyl)-2-methyl-hept-2-enyl ester
—— 4-(2-iodo)benzyloxyphenol 398142-27-3 C13H11IO2
4-(2-iodo)benzyloxyphenol
—— bis(5-bromo-2-hydroxybenzylidene)succinohydrazide 329905-64-8 C18H16Br2N4O4
bis(5-bromo-2-hydroxybenzylidene)succinohydrazide
—— 35,75-di-tert-butyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,15,32,52,55,72-hexaol 1237538-96-3 C36H40O6
35,75-di-tert-butyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,15,32,52,55,72-hexaol
—— 4-Bromo-2-{[(Z)-2-dodecylsulfanyl-ethylimino]-methyl}-phenol 95000-86-5 C21H34BrNOS
4-Bromo-2-{[(Z)-2-dodecylsulfanyl-ethylimino]-methyl}-phenol
—— 2,5-Dichlor-4-hydroxy-3-nitro-benzonitril 3861-52-7 C7H2Cl2N2O3
2,5-Dichlor-4-hydroxy-3-nitro-benzonitril
—— 2,3,5,6-tetrafluoro-4-hydroxyphenylacetylene 73732-48-6 C8H2F4O
2,3,5,6-tetrafluoro-4-hydroxyphenylacetylene
—— 5-acetyl-4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-3-carbonitrile 1350309-97-5 C15H14N2O3
5-acetyl-4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-3-carbonitrile
—— 131225-75-7 C104H116O12
—— 2-cyano-N,N-diethyl-5-hydroxy-4-methoxybenzamide 1202894-34-5 C13H16N2O3
2-cyano-N,N-diethyl-5-hydroxy-4-methoxybenzamide
—— 5-[(4-hydroxy-3-methoxyphenyl)-(1H-indol-3-yl)methyl]-1,3-dimethyl-1,3-diazinane-2,4,6-trione 1228563-15-2 C22H21N3O5
5-[(4-hydroxy-3-methoxyphenyl)-(1H-indol-3-yl)methyl]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
—— 1-(benzyloxy)-4-(2-octyloxyethyl)benzene 1327337-35-8 C23H32O2
1-(benzyloxy)-4-(2-octyloxyethyl)benzene
—— 2,4-dibromo-5-methoxyresorcinol 121869-53-2 C7H6Br2O3
2,4-dibromo-5-methoxyresorcinol
—— (E)-5-(((2-hydroxyphenyl)imino)methyl)-2-methoxyphenol 1415567-41-7 C14H13NO3
(E)-5-(((2-hydroxyphenyl)imino)methyl)-2-methoxyphenol
—— 4-(bis(3,4-diethyl-5-methyl-1H-pyrrol-2-yl)methyl)phenol 1267502-26-0 C25H34N2O
4-(bis(3,4-diethyl-5-methyl-1H-pyrrol-2-yl)methyl)phenol
—— thiazolidine-2,4-dione-2-[1-(2,4-dihydroxy-phenyl)-ethylLiDenehydrazone] 109847-33-8 C11H11N3O3S
thiazolidine-2,4-dione-2-[1-(2,4-dihydroxy-phenyl)-ethylLiDenehydrazone]
—— 2-[4-[2-(3,4-Dichlorophenyl)ethoxy]phenyl]acetic acid 900515-72-2 C16H14Cl2O3
2-[4-[2-(3,4-Dichlorophenyl)ethoxy]phenyl]acetic acid
—— Benzenepropanol, I(3)-amino-4-hydroxy-3-iodo- 1273664-74-6 C9H12INO2
Benzenepropanol, I(3)-amino-4-hydroxy-3-iodo-
—— 5,5'-bis-(3-methoxy-4-hydroxy-benzylidene)-3,3'-<i>p</i>-phenylenedimethyl-bis-thiazolidine-2,4-dione 69258-68-0 C30H24N2O8S2
5,5'-bis-(3-methoxy-4-hydroxy-benzylidene)-3,3'-<i>p</i>-phenylenedimethyl-bis-thiazolidine-2,4-dione
—— 3-amino-6-fluoro-2-methylphenol 1784742-57-9 C7H8FNO
3-amino-6-fluoro-2-methylphenol
—— 2-[(2-hydroxyphenyl)methylideneamino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophene-3-carbonitrile 1428543-69-4 C17H16N2OSe
2-[(2-hydroxyphenyl)methylideneamino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophene-3-carbonitrile
—— 3,4-Dibromotrifluorophenol 19758-05-5 C6HBr2F3O
3,4-Dibromotrifluorophenol
—— 3-(4-hydroxy-phenyl)-2-prop-1-ynyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104633-74-0 C17H16O2
3-(4-hydroxy-phenyl)-2-prop-1-ynyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— 5,8-Dimethyl-4-nitro-5,6,7,8-tetrahydro-naphthalen-1-ol 41059-19-2 C12H15NO3
5,8-Dimethyl-4-nitro-5,6,7,8-tetrahydro-naphthalen-1-ol
—— 4-(2-tert-Butylamino-1-hydroxy-ethyl)-3-methyl-benzene-1,2-diol; compound with benzoic acid 24008-05-7 C7H6O2*C13H21NO3
4-(2-tert-Butylamino-1-hydroxy-ethyl)-3-methyl-benzene-1,2-diol; compound with benzoic acid
—— 2,4,6-Tribromo-3-(dimethyl-hydrazonomethyl)-phenol 14395-32-5 C9H9Br3N2O
2,4,6-Tribromo-3-(dimethyl-hydrazonomethyl)-phenol
—— 2,4-Dibromo-6-(dimethyl-hydrazonomethyl)-phenol 14395-33-6 C9H10Br2N2O
2,4-Dibromo-6-(dimethyl-hydrazonomethyl)-phenol
—— 2-Amino-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylene]-4,6-dimethyl-5H-cyclopenta[b]pyridine-3,7-dicarbonitrile 340319-16-6 C20H15BrN4O2
2-Amino-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylene]-4,6-dimethyl-5H-cyclopenta[b]pyridine-3,7-dicarbonitrile
—— ethyl 2-formyl-3-hydroxy-4-methoxyphenylacetate 155270-97-6 C12H14O5
ethyl 2-formyl-3-hydroxy-4-methoxyphenylacetate
—— 1452925-50-6 C12H14BrFO3
—— 3-Hydroxy-N-p-tolyl-thiobenzamide 38309-95-4 C14H13NOS
3-Hydroxy-N-p-tolyl-thiobenzamide
—— 5-Nitro-salicylaldehyd-<-4-nitro-benzolsulfonylhydrazon> 5446-50-4 C13H10N4O7S
5-Nitro-salicylaldehyd-<-4-nitro-benzolsulfonylhydrazon>
—— Diethyl(2-hydroxy-3-methoxybenzyliden)dicarbamat 23121-80-4 C14H20N2O6
Diethyl(2-hydroxy-3-methoxybenzyliden)dicarbamat
—— N-(5-Nitrosalicyliden)-D-cycloserin 28831-99-4 C10H9N3O5
N-(5-Nitrosalicyliden)-D-cycloserin
—— 4-{2-[4-((1R,3R)-3-amino-3-hydroxymethyl-cyclopentyl)-phenoxy]-ethyl}-phenol 1036391-68-0 C20H25NO3
4-{2-[4-((1R,3R)-3-amino-3-hydroxymethyl-cyclopentyl)-phenoxy]-ethyl}-phenol
—— 2,2'-dibromo-6,6'-dinitro-4,4'-sec-butylidene-di-phenol 860766-78-5 C16H14Br2N2O6
2,2'-dibromo-6,6'-dinitro-4,4'-sec-butylidene-di-phenol