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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
—— (E)-3'-hydroxy-4'-methoxypropiophenone O-4-nitrobenzyl oxime 1072708-50-9 C17H18N2O5
(E)-3'-hydroxy-4'-methoxypropiophenone O-4-nitrobenzyl oxime
—— [(4-hydroxy-phenyl)-morpholin-4-yl-methylene]-malononitrile 3411-86-7 C14H13N3O2
[(4-hydroxy-phenyl)-morpholin-4-yl-methylene]-malononitrile
—— 2-Propen-1-one, 1-(2-hydroxy-5-methylphenyl)-3-(1-piperidinyl)-, (E)- 80031-00-1 C15H19NO2
2-Propen-1-one, 1-(2-hydroxy-5-methylphenyl)-3-(1-piperidinyl)-, (E)-
—— 2,3,4,5-tetrafluoro-6-methylphenol 113397-94-7 C7H4F4O
2,3,4,5-tetrafluoro-6-methylphenol
—— 3-(2,2,2-Trifluoroethyl)phenol 161611-53-6 C8H7F3O
3-(2,2,2-Trifluoroethyl)phenol
—— 2-(4-hydroxy-3,5-dimethoxybenzylidene)-1-benzothiophen-3(2H)-one 5659-88-1 C17H14O4S
2-(4-hydroxy-3,5-dimethoxybenzylidene)-1-benzothiophen-3(2H)-one
—— 2-[[(5-methyl-1H-pyrazol-3-yl)imino]methyl]-phenol 477878-35-6 C11H11N3O
2-[[(5-methyl-1H-pyrazol-3-yl)imino]methyl]-phenol
—— (4e)-4-(2-Hydroxy-3-methoxybenzylidene)-1-phenylpyrazolidine-3,5-dione 5617-08-3 C17H14N2O4
(4e)-4-(2-Hydroxy-3-methoxybenzylidene)-1-phenylpyrazolidine-3,5-dione
—— 4-[(5-Chloro-2-hydroxyanilino)methylidene]cyclohexa-2,5-dien-1-one 5473-57-4 C13H10ClNO2
4-[(5-Chloro-2-hydroxyanilino)methylidene]cyclohexa-2,5-dien-1-one
—— 2-[(5-Chloro-2-hydroxyphenyl)iminomethyl]-6-methylphenol 416885-38-6 C14H12ClNO2
2-[(5-Chloro-2-hydroxyphenyl)iminomethyl]-6-methylphenol
—— tert-butyl 2-(4-hydroxy-2-methoxyphenyl)propionate 948573-83-9 C14H20O4
tert-butyl 2-(4-hydroxy-2-methoxyphenyl)propionate
—— 2-[(2-Hydroxy-4-methylphenyl)iminomethyl]-6-methylphenol 5486-02-2 C15H15NO2
2-[(2-Hydroxy-4-methylphenyl)iminomethyl]-6-methylphenol
—— 2,9-DIMETHYL-2,9-DIMERCAPTO-5-(2-HYDROXYPHENYL)-4,7-DIAZADECANE 96929-53-2 C16H28N2OS2
2,9-DIMETHYL-2,9-DIMERCAPTO-5-(2-HYDROXYPHENYL)-4,7-DIAZADECANE
—— 1-(2-hydroxy-5-nitrophenyl)-3-(3-thienyl)-2-propen-1-one 118761-30-1 C13H9NO4S
1-(2-hydroxy-5-nitrophenyl)-3-(3-thienyl)-2-propen-1-one
—— N-(3,5-Dimethoxy-4-Hydroxybenzylidene)Aniline 58606-44-3 C15H15NO3
N-(3,5-Dimethoxy-4-Hydroxybenzylidene)Aniline
—— 2-Hydroxy-5-nitroacetophenon-oxim 87974-52-5 C8H8N2O4
2-Hydroxy-5-nitroacetophenon-oxim
—— 2-{1-[(E)-4-Bromo-phenylimino]-ethyl}-4-chloro-phenol 105533-45-7 C14H11BrClNO
2-{1-[(E)-4-Bromo-phenylimino]-ethyl}-4-chloro-phenol
—— 2-Hydroxy-5-nitro-ω-thiophenylideneacetophenone 76988-07-3 C13H9NO4S
2-Hydroxy-5-nitro-ω-thiophenylideneacetophenone
—— 2-((diethylamino)methyl)benzene-1,4-diol 2610-38-0 C11H17NO2
2-((diethylamino)methyl)benzene-1,4-diol
—— 5-[1-(3-Hydroxy-phenyl)-meth-(Z)-ylidene]-2-methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester 99761-82-7 C15H15NO4
5-[1-(3-Hydroxy-phenyl)-meth-(Z)-ylidene]-2-methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester
—— 2'-hydroxy-4'-methoxyacetophenone ethylene hemithioketal 136257-92-6 C11H14O3S
2'-hydroxy-4'-methoxyacetophenone ethylene hemithioketal
—— sinapyl acetate 94930-90-2 C13H16O5
sinapyl acetate
—— 4,4'-(dibutylsilanediyl)bis(2-methylphenol) 1446215-31-1 C22H32O2Si
4,4'-(dibutylsilanediyl)bis(2-methylphenol)
—— 4-Benzo[1,3]dioxol-5-yl-6-(2-hydroxy-4-methoxy-phenyl)-2,3a,4,5-tetrahydro-indazol-3-one 101986-23-6 C21H18N2O5
4-Benzo[1,3]dioxol-5-yl-6-(2-hydroxy-4-methoxy-phenyl)-2,3a,4,5-tetrahydro-indazol-3-one
—— normetanephrine 2282-54-4 C10H15NO3
normetanephrine
—— 2-(Tert-butyliminomethyl)-4-nitrophenol 215232-64-7 C11H14N2O3
2-(Tert-butyliminomethyl)-4-nitrophenol
—— 5-chloro-2,4,6-trimethyl-resorcinol 137324-48-2 C9H11ClO2
5-chloro-2,4,6-trimethyl-resorcinol
—— 2,5-Dihydroxy-4-methyl-octyl-benzol 21182-62-7 C15H24O2
2,5-Dihydroxy-4-methyl-octyl-benzol
—— 5-Hydroxy-1,3-benzoxathiol-2-thion 7735-70-8 C7H4O2S2
5-Hydroxy-1,3-benzoxathiol-2-thion
—— 2-{[(E)-2,5-Dimethoxy-phenylimino]-methyl}-4-nitro-phenol 90284-75-6 C15H14N2O5
2-{[(E)-2,5-Dimethoxy-phenylimino]-methyl}-4-nitro-phenol
—— Dimethyl 16,40-dihydroxy-12,20,36,44-tetrathianonacyclo[44.2.2.27,10.222,25.231,34.12,6.114,18.126,30.138,42]hexaconta-1(48),2(60),3,5,7(59),8,10(58),14(57),15,17,22(56),23,25(55),26,28,30(54),31,33,38,40,42(51),46,49,52-tetracosaene-54,60-dicarboxylate 177798-49-1 C60H52O6S4
Dimethyl 16,40-dihydroxy-12,20,36,44-tetrathianonacyclo[44.2.2.27,10.222,25.231,34.12,6.114,18.126,30.138,42]hexaconta-1(48),2(60),3,5,7(59),8,10(58),14(57),15,17,22(56),23,25(55),26,28,30(54),31,33,38,40,42(51),46,49,52-tetracosaene-54,60-dicarboxylate
—— 5,6-dibromo-2-methylphenol 77339-21-0 C7H6Br2O
5,6-dibromo-2-methylphenol
—— 4-(4-Methyl-4,5-dihydro-1H-pyrazol-3-yl)-phenol 123716-82-5 C10H12N2O
4-(4-Methyl-4,5-dihydro-1H-pyrazol-3-yl)-phenol
—— (6R)-N-(2-hydroxy-5-methylphenyl)-4-methoxy-6-phenyl-3,4-didehydropiperidin-2-one 910471-00-0 C19H19NO3
(6R)-N-(2-hydroxy-5-methylphenyl)-4-methoxy-6-phenyl-3,4-didehydropiperidin-2-one
—— (R)-fornicin A 908588-41-0 C16H18O4
(R)-fornicin A
—— 5-fluoro-3-hydroxy-2-methylbenzonitrile 1591829-03-6 C8H6FNO
5-fluoro-3-hydroxy-2-methylbenzonitrile
—— 2-{[(2-furanylmethyl)amino]methyl}-6-(methoxy)phenol 827328-42-7 C13H15NO3
2-{[(2-furanylmethyl)amino]methyl}-6-(methoxy)phenol
—— 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 329211-33-8 C24H27BrO5
9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
—— 9-(3,5-dibromo-4-hydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione 5626-17-5 C23H24Br2O4
9-(3,5-dibromo-4-hydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
—— 4-[(1S,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 1260153-11-4 C18H24O3
4-[(1S,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol
—— 4-[(1R,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 1260153-18-1 C18H24O3
4-[(1R,3aR,7aS)-1,3,3a,4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol
—— 4-[(3αR,7αS)-1,3,3α,4,5,7α-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 1352734-67-8 C18H24O3
4-[(3αR,7αS)-1,3,3α,4,5,7α-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol
—— 4-(4,5-di-p-tolyl-1H-imidazol-2-yl)phenol 24777-16-0 C23H20N2O
4-(4,5-di-p-tolyl-1H-imidazol-2-yl)phenol
—— 3-azido-2,4,6-trinitrophenol 1613311-04-8 C6H2N6O7
3-azido-2,4,6-trinitrophenol
—— [(R)-2-hydroxy-1-(4-hydroxy-2-methyl-phenyl)ethyl]carbamic acid tert-butyl ester 1286280-58-7 C14H21NO4
[(R)-2-hydroxy-1-(4-hydroxy-2-methyl-phenyl)ethyl]carbamic acid tert-butyl ester
—— 2-[[4-[(4-Ethoxyphenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol 6117-65-3 C21H28N2O3
2-[[4-[(4-Ethoxyphenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol
—— 6-Hydroxymethyl-2,3-dimethoxy-phenol 219918-14-6 C9H12O4
6-Hydroxymethyl-2,3-dimethoxy-phenol
—— (Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxothiazolidin-4-one —— C11H8BrNO3S2
(Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxothiazolidin-4-one
—— 4-(2-cyanoethyl)-2,6-dimethylphenol 58471-30-0 C11H13NO
4-(2-cyanoethyl)-2,6-dimethylphenol
—— 4-But-2-enyl-o-kresol 7572-85-2 C11H14O
4-But-2-enyl-o-kresol