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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
—— 1-(2'-hydroxy-5'-methoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one 33268-84-7 C18H15NO3
1-(2'-hydroxy-5'-methoxyphenyl)-3-(1-indol-3-yl)-prop-2-en-1-one
—— 2-(tert-butyldimethylsilyl)-5,6-dimethyl-3-(triisopropylsiloxy)phenol 1006058-00-9 C23H44O2Si2
2-(tert-butyldimethylsilyl)-5,6-dimethyl-3-(triisopropylsiloxy)phenol
—— O,O-Di-isobutyl-1-(5-brom-2-hydroxyphenyl)-3-hydroxy-2-butenylphosphonat 40468-45-9 C18H28BrO5P
O,O-Di-isobutyl-1-(5-brom-2-hydroxyphenyl)-3-hydroxy-2-butenylphosphonat
—— (E,Z)-cyano-{3-ethyl-5-[(E,Z)-1-(4-hydroxy-3-methyl-phenylamino)-methylene]-4-oxo-thiazolidin-2-ylidene}-acetic acid ethyl ester 851646-14-5 C18H19N3O4S
(E,Z)-cyano-{3-ethyl-5-[(E,Z)-1-(4-hydroxy-3-methyl-phenylamino)-methylene]-4-oxo-thiazolidin-2-ylidene}-acetic acid ethyl ester
—— 2-thiocyanatobenzene-1,4-diol 1174416-06-8 C7H5NO2S
2-thiocyanatobenzene-1,4-diol
—— 2-(4-hydroxy-benzyl)-5-phenyl-1<i>H</i>-pyrimidine-4,6-dione 39696-05-4 C17H14N2O3
2-(4-hydroxy-benzyl)-5-phenyl-1<i>H</i>-pyrimidine-4,6-dione
—— 2-<3.5-Dimethyl-4-hydroxy-benzylmercapto>-ethylphosphonsaeure-diethylester 34446-22-5 C15H25O4PS
2-<3.5-Dimethyl-4-hydroxy-benzylmercapto>-ethylphosphonsaeure-diethylester
—— 3.4-Bis-(4-hydroxy-3-methoxy-phenyl)-5-(2-methoxy-phenoxy)-2-hexanon 25081-55-4 C27H30O7
3.4-Bis-(4-hydroxy-3-methoxy-phenyl)-5-(2-methoxy-phenoxy)-2-hexanon
—— [(2S)-1-[acetyl(propan-2-yl)amino]-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propan-2-yl] acetate 169613-97-2 C22H33NO5
[(2S)-1-[acetyl(propan-2-yl)amino]-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]propan-2-yl] acetate
—— N-(3-fluoro-4-hydroxybenzyl)-N-isopropylmethacrylamide 1612841-42-5 C14H18FNO2
N-(3-fluoro-4-hydroxybenzyl)-N-isopropylmethacrylamide
—— methyl 3-(2-hydroxy-5-methoxyphenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate 114106-34-2 C15H20O6S
methyl 3-(2-hydroxy-5-methoxyphenyl)-3-(3-methoxy-3-oxopropyl)sulfanylpropanoate
—— cis-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile 71750-10-2 C10H9NO2
cis-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile
—— 2-Chlor-4,5-dihydroxy-phenylessigsaeure-aethylester 17891-01-9 C10H11ClO4
2-Chlor-4,5-dihydroxy-phenylessigsaeure-aethylester
—— [(3-Bromo-4-hydroxy-5-methoxy-phenyl)-hydroxy-methyl]-phosphonic acid dipentyl ester 36971-45-6 C18H30BrO6P
[(3-Bromo-4-hydroxy-5-methoxy-phenyl)-hydroxy-methyl]-phosphonic acid dipentyl ester
—— 6-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-5-nitro-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 40189-00-2 C23H23NO8
6-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-5-nitro-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
—— 4-(3-chloro-4-hydroxyphenyl)-6-(cyclohexyloxymethyl)-5-propionyl3,4-dihydropyrimidin-2(1H)-one 1224683-78-6 C20H25ClN2O4
4-(3-chloro-4-hydroxyphenyl)-6-(cyclohexyloxymethyl)-5-propionyl3,4-dihydropyrimidin-2(1H)-one
—— 2-(thiazol-2-ylazo)-p-cresol 198827-08-6 C10H9N3OS
2-(thiazol-2-ylazo)-p-cresol
—— 4-hydroxy-5,7-dinitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxide 1459727-88-8 C12H12N4O6
4-hydroxy-5,7-dinitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxide
—— 4-Chloro-2-((Z)-2-chloro-2-nitro-vinyl)-phenol 117672-18-1 C8H5Cl2NO3
4-Chloro-2-((Z)-2-chloro-2-nitro-vinyl)-phenol
—— 2-(2,3-dihydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide 479513-53-6 C14H13N3O2S
2-(2,3-dihydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide
—— 2-[1-(3-bromo-4-hydroxy-5-methoxy-phenyl)-meth-(Z)-ylidene]-6-(2-methylpyridin-4-yl)-imidazo[2,1-b]thiazol-3-one 1567849-31-3 C19H14BrN3O3S
2-[1-(3-bromo-4-hydroxy-5-methoxy-phenyl)-meth-(Z)-ylidene]-6-(2-methylpyridin-4-yl)-imidazo[2,1-b]thiazol-3-one
—— o-hydroxybenzoylacetone dioxime 53824-21-8 C10H12N2O3
o-hydroxybenzoylacetone dioxime
—— 4-(2-(4-methoxyphenylhydrazono))-1-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one 1456804-38-8 C21H18N8O5S
4-(2-(4-methoxyphenylhydrazono))-1-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one
—— 4,6-bis(1-hydrazonoethyl)benzene-1,3-diol 115705-35-6 C10H14N4O2
4,6-bis(1-hydrazonoethyl)benzene-1,3-diol
—— meso-(2,3-dihydroxyphenyl)dipyrromethane 1219834-96-4 C15H14N2O2
meso-(2,3-dihydroxyphenyl)dipyrromethane
—— 3-(2'-fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione 110956-96-2 C12H9ClFNO4
3-(2'-fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione
—— 27421-58-5 C13H20N4OS
—— 5-Methoxy-4-nitroso-2-tert.-butyl-phenol 36150-67-1 C11H15NO3
5-Methoxy-4-nitroso-2-tert.-butyl-phenol
—— 6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose-(1,4) 109748-38-1 C34H41N3O13S2
6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose-(1,4)
—— 103375-94-6 C6H3N3O7*C11H16ClNS
—— N'-[(1E)-(m-hydroxyphenyl)methylene]phosphorohydrazidic acid diisopropyl ester 1237507-92-4 C13H21N2O4P
N'-[(1E)-(m-hydroxyphenyl)methylene]phosphorohydrazidic acid diisopropyl ester
—— 1-Hydroxy-5-(2-hydroxy-4,6-dimethyl-phenyl)-pentan-2-one 71862-25-4 C13H18O3
1-Hydroxy-5-(2-hydroxy-4,6-dimethyl-phenyl)-pentan-2-one
—— Phenol, 2-[(1S)-1-amino-2-cyclopropylethyl]-3-bromo-6-fluoro- 1336746-48-5 C11H13BrFNO
Phenol, 2-[(1S)-1-amino-2-cyclopropylethyl]-3-bromo-6-fluoro-
—— dimethylsulfoniopropionate picrate 1303567-81-8 C5H10O2S*C6H3N3O7
dimethylsulfoniopropionate picrate
—— 3,4-dibromo-5-chloro-phenol 855839-00-8 C6H3Br2ClO
3,4-dibromo-5-chloro-phenol
—— 2-(3',4'-dihydroxy)benzyl-3-fluoroallylamine 85278-81-5 C10H12FNO2
2-(3',4'-dihydroxy)benzyl-3-fluoroallylamine
—— (E)-3-(5-Chloro-1-methyl-1H-imidazol-2-yl)-1-(2-hydroxy-5-methoxy-phenyl)-propenone 122183-21-5 C14H13ClN2O3
(E)-3-(5-Chloro-1-methyl-1H-imidazol-2-yl)-1-(2-hydroxy-5-methoxy-phenyl)-propenone
—— 4-hydroxy-3-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-4-(4-hydroxyphenyl)pyridin-2-yl)-6-methyl-2H-pyran-2-one 1499931-23-5 C23H17NO7
4-hydroxy-3-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-4-(4-hydroxyphenyl)pyridin-2-yl)-6-methyl-2H-pyran-2-one
—— Ethyl-5-[2,5-dihydroxy-3,6-diallylphenyl]pent-2E,4E-dieneoate 103811-72-9 C19H22O4
Ethyl-5-[2,5-dihydroxy-3,6-diallylphenyl]pent-2E,4E-dieneoate
—— (+/-)-2-[7-(4-bromophenyl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-3-methoxyphenol 1196202-98-8 C18H15BrN4O2
(+/-)-2-[7-(4-bromophenyl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-3-methoxyphenol
—— 2,4-Dibromo-6-{[(E)-2-(5-methyl-3H-imidazol-4-ylmethylsulfanyl)-ethylimino]-methyl}-phenol 130106-90-0 C14H15Br2N3OS
2,4-Dibromo-6-{[(E)-2-(5-methyl-3H-imidazol-4-ylmethylsulfanyl)-ethylimino]-methyl}-phenol
—— N-[2-(3,4-dihydroxyphenyl)ethyl]guanidinium bromide 14279-98-2 BrH*C9H13N3O2
N-[2-(3,4-dihydroxyphenyl)ethyl]guanidinium bromide
—— 26,28-dihydroxy-25,27-dimethoxy-5,17-bis(propyldimethylsilyl)calix[4]arene 1092456-23-9 C40H52O4Si2
26,28-dihydroxy-25,27-dimethoxy-5,17-bis(propyldimethylsilyl)calix[4]arene
—— 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzenecarbothioamide 23238-76-8 C13H8Cl2N2O3S
5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzenecarbothioamide
—— 4-(5-Acetoxy-3-brom-4-methoxybenzyliden)-2-methyl-5-oxazolon 23354-31-6 C12H10BrNO4
4-(5-Acetoxy-3-brom-4-methoxybenzyliden)-2-methyl-5-oxazolon
—— 2-bromo-4-(1,3-dioxolan-2-yl)-6-trimethylsilylphenol 1276113-35-9 C12H17BrO3Si
2-bromo-4-(1,3-dioxolan-2-yl)-6-trimethylsilylphenol
—— 5-(4-amino-2-hydroxy-phenyl)-3-benzyl-3H-[1,3,4]oxadiazole-2-thione 15313-80-1 C15H13N3O2S
5-(4-amino-2-hydroxy-phenyl)-3-benzyl-3H-[1,3,4]oxadiazole-2-thione
—— 2-(4-hydroxy-benzyl)-1<i>H</i>-pyrimidine-4,6-dione 39696-04-3 C11H10N2O3
2-(4-hydroxy-benzyl)-1<i>H</i>-pyrimidine-4,6-dione
—— cyclohexylmethyl 4-(3-chloro-4,5-dihydroxyphenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 1224683-34-4 C20H25ClN2O5
cyclohexylmethyl 4-(3-chloro-4,5-dihydroxyphenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 2-methylimidazolinium picrate 24690-70-8 C4H6N2*C6H3N3O7
2-methylimidazolinium picrate