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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
—— potassium (7-(4-hydroxy-3,5-dimethylphenyl)-6-nitro-1-oxidobenzo[c][1,2,5]oxadiazol-4(7H)-ylidene)azinate 105563-84-6 C14H11N4O7*K
potassium (7-(4-hydroxy-3,5-dimethylphenyl)-6-nitro-1-oxidobenzo[c][1,2,5]oxadiazol-4(7H)-ylidene)azinate
—— 2,4-di(2-cyclohexenyl)phenol 98382-16-2 C18H22O
2,4-di(2-cyclohexenyl)phenol
—— (2S,4S,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol 1292847-83-6 C18H24O5
(2S,4S,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol
—— 2-methoxy-4-methyl-6-propoxyphenol 1574215-76-1 C11H16O3
2-methoxy-4-methyl-6-propoxyphenol
—— 5-nitro-4-hydroxyphthalic acid 856806-22-9 C8H5NO7
5-nitro-4-hydroxyphthalic acid
—— 1-(1-Aethylmercapto-propyl)-4-hydroxy-3-methoxy-benzol 109041-66-9 C12H18O2S
1-(1-Aethylmercapto-propyl)-4-hydroxy-3-methoxy-benzol
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(1,3-thiazolidin-3-yl)-4,5-dihydro-1,3-thiazol-4-one 1181082-54-1 C13H12N2O2S2
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(1,3-thiazolidin-3-yl)-4,5-dihydro-1,3-thiazol-4-one
—— (5Z)-5-[(3-fluoro-2-hydroxyphenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-55-9 C15H15FN2O2S
(5Z)-5-[(3-fluoro-2-hydroxyphenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 5-methyl-3-((Ξ)-vanillylidene)-3<i>H</i>-furan-2-one 36805-02-4 C13H12O4
5-methyl-3-((Ξ)-vanillylidene)-3<i>H</i>-furan-2-one
—— (4S)-3-((1R,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclohex-3-enecarbonyl)-4-phenyloxazolidin-2-one 1595280-39-9 C23H23NO5
(4S)-3-((1R,2S)-2-(4-hydroxy-3-methoxyphenyl)cyclohex-3-enecarbonyl)-4-phenyloxazolidin-2-one
—— o-nitrophenol anion 16554-53-3 C6H5NO3
o-nitrophenol anion
—— 1,1'-di(salicylaldiminoethylaminocarbonylethyl)-2,2'-biimidazole 1100751-53-8 C30H34N8O4
1,1'-di(salicylaldiminoethylaminocarbonylethyl)-2,2'-biimidazole
—— 4-hydroxy-2-(9-hydroxy-5-oxanonyloxy)benzoic acid lactone 77376-53-5 C15H20O5
4-hydroxy-2-(9-hydroxy-5-oxanonyloxy)benzoic acid lactone
—— tert-butyl (2S)-2-[(R)-hydroxy-(2-hydroxy-5-methoxyphenyl)methyl]pyrrolidine-1-carboxylate 130832-50-7 C17H25NO5
tert-butyl (2S)-2-[(R)-hydroxy-(2-hydroxy-5-methoxyphenyl)methyl]pyrrolidine-1-carboxylate
—— 2-(2-Hydroxy-5-methoxy-3-methylphenyl)-propen 38102-60-2 C11H14O2
2-(2-Hydroxy-5-methoxy-3-methylphenyl)-propen
—— 4,4'-dihydroxy-5,5'-dinitrobiphenyl-3,3'-dicarbaldehyde 27344-30-5 C14H8N2O8
4,4'-dihydroxy-5,5'-dinitrobiphenyl-3,3'-dicarbaldehyde
—— 4-bromo-5-fluoro-2-(N-hydroxy-C-methylcarbonimidoyl)phenol 1263431-44-2 C8H7BrFNO2
4-bromo-5-fluoro-2-(N-hydroxy-C-methylcarbonimidoyl)phenol
—— N-[4-(3,4-Dihydroxyphenyl)-3-methyl-1,3-thiazol-2(3H)-ylidene]guanidine 694431-26-0 C11H12N4O2S
N-[4-(3,4-Dihydroxyphenyl)-3-methyl-1,3-thiazol-2(3H)-ylidene]guanidine
—— 4-Chloro-2-{[(Z)-2,3,5,6-tetrafluoro-phenylimino]-methyl}-phenol 26672-11-7 C13H6ClF4NO
4-Chloro-2-{[(Z)-2,3,5,6-tetrafluoro-phenylimino]-methyl}-phenol
—— 2-bromo-3,4-dimethoxyphenol 16276-35-0 C8H9BrO3
2-bromo-3,4-dimethoxyphenol
—— bis(2-hydroxy-3-methoxybenzylidene)succinohydrazide 346721-28-6 C20H22N4O6
bis(2-hydroxy-3-methoxybenzylidene)succinohydrazide
—— 2-{1-[(Z)-3-Methoxy-phenylimino]-ethyl}-4-methyl-6-nitro-phenol 112932-60-2 C16H16N2O4
2-{1-[(Z)-3-Methoxy-phenylimino]-ethyl}-4-methyl-6-nitro-phenol
—— 1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-hydroxy-5-methoxybenzene 118967-77-4 C17H20O7
1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-hydroxy-5-methoxybenzene
—— 4-[(2-Fluorophenyl)methoxy]phenol 1094247-88-7 C13H11FO2
4-[(2-Fluorophenyl)methoxy]phenol
—— 1,4-dimethyl-7-tert-butyl-8-hydroxy-10-(3',5'-di-tert-butyl-4'-hydroxyphenyl)-5,10-dihydrobenzo<g>phthalazine trifluoroacetate 111534-91-9 C2HF3O2*C32H42N2O2
1,4-dimethyl-7-tert-butyl-8-hydroxy-10-(3',5'-di-tert-butyl-4'-hydroxyphenyl)-5,10-dihydrobenzo<g>phthalazine trifluoroacetate
—— 2,6-Bis-{[(E)-4-chloro-phenylimino]-methyl}-4-methyl-phenol 213403-76-0 C21H16Cl2N2O
2,6-Bis-{[(E)-4-chloro-phenylimino]-methyl}-4-methyl-phenol
—— 2-{[(Z)-2,4,6-Tribromo-phenylimino]-methyl}-phenol 26672-07-1 C13H8Br3NO
2-{[(Z)-2,4,6-Tribromo-phenylimino]-methyl}-phenol
—— 2-(1-aminoethyl)-5-methoxyphenol 1021267-65-1 C9H13NO2
2-(1-aminoethyl)-5-methoxyphenol
—— 2,4-Di-tert-butyl-3-chloro-6-methoxy-phenol 34896-16-7 C15H23ClO2
2,4-Di-tert-butyl-3-chloro-6-methoxy-phenol
—— ethyl (2'S,7S)-4-hydroxyspiro[bicyclo[4.2.0]octane-7,1'-cyclopropane]-1,3,5-triene-2'-carboxylate 1222090-85-8 C13H14O3
ethyl (2'S,7S)-4-hydroxyspiro[bicyclo[4.2.0]octane-7,1'-cyclopropane]-1,3,5-triene-2'-carboxylate
—— bis-N,N'-(2-hydroxyacetophenylidine)-1,3-propanediamine 54216-01-2 C19H22N2O2
bis-N,N'-(2-hydroxyacetophenylidine)-1,3-propanediamine
—— 4-cyclopentyl-2,6-dinitro-phenol 20240-45-3 C11H12N2O5
4-cyclopentyl-2,6-dinitro-phenol
—— 2-Bromo-6-hydrazonomethyl-4-nitro-phenol 51084-77-6 C7H6BrN3O3
2-Bromo-6-hydrazonomethyl-4-nitro-phenol
—— tert-butyl N-[(3S)-1-[(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]pyrrolidin-3-yl]carbamate 1181082-60-9 C19H22FN3O4S
tert-butyl N-[(3S)-1-[(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]pyrrolidin-3-yl]carbamate
—— (Benzimidazol-2-ylmethyl)(2-hydroxy-5-nitrobenzyl)amine 155797-25-4 C15H14N4O3
(Benzimidazol-2-ylmethyl)(2-hydroxy-5-nitrobenzyl)amine
—— 163087-00-1 C34H32I2N8NdO6*I
—— 6-Tetralol-5-<3H> 33501-03-0 C10H12O
6-Tetralol-5-<3H>
—— 1,3-dihydroxy-5-hexadec-trans-1'-enylbenzene 117940-45-1 C22H36O2
1,3-dihydroxy-5-hexadec-trans-1'-enylbenzene
—— 1452925-49-3 C12H15FO3
—— N'-(2-hydroxybenzylidene)-3-sulfanylpropionohydrazide 1239460-65-1 C10H12N2O2S
N'-(2-hydroxybenzylidene)-3-sulfanylpropionohydrazide
—— 3-Triethylsilanyloxymethyl-phenol 78382-15-7 C13H22O2Si
3-Triethylsilanyloxymethyl-phenol
—— 4-(2-hydroxy-4,5-dimethoxyphenyl)-6-phenyl-4,5-dihydropyridazin-3(2H)-one 1416565-93-9 C18H18N2O4
4-(2-hydroxy-4,5-dimethoxyphenyl)-6-phenyl-4,5-dihydropyridazin-3(2H)-one
—— (E)-5-(5-bromo-2-hydroxyphenyl)pent-2-enyl acetate 1360054-22-3 C13H15BrO3
(E)-5-(5-bromo-2-hydroxyphenyl)pent-2-enyl acetate
—— 2-((1-hydroxybutan-2-ylimino)methyl)-6-methoxyphenol 1353118-90-7 C12H17NO3
2-((1-hydroxybutan-2-ylimino)methyl)-6-methoxyphenol
—— 2'-Hydroxy-4'-chlorbenzaldehyd-5-chlor-2-methylanil 34801-00-8 C14H11Cl2NO
2'-Hydroxy-4'-chlorbenzaldehyd-5-chlor-2-methylanil
—— N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-2-methoxy-acetamide 53671-94-6 C14H22N2O5
N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-2-methoxy-acetamide
—— 3,6-Bis(24-chlortetracosyl)brenzcatechin 72619-58-0 C54H100Cl2O2
3,6-Bis(24-chlortetracosyl)brenzcatechin
—— S-methyl-β-N-((2-hydroxy-3-methoxyphenyl)-methylene)-dithiocarbazate 42183-27-7 C10H12N2O2S2
S-methyl-β-N-((2-hydroxy-3-methoxyphenyl)-methylene)-dithiocarbazate
—— (R)-1-(3-hydroxyphenyl)-2-<N-methyl-N-(dimethylthiocarbamoyl)amino>ethanol 110193-50-5 C12H18N2O2S
(R)-1-(3-hydroxyphenyl)-2-<N-methyl-N-(dimethylthiocarbamoyl)amino>ethanol
—— [2-(2-Benzyloxy-phenoxy)-ethyl]-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine 10414-91-2 C25H29NO4
[2-(2-Benzyloxy-phenoxy)-ethyl]-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine