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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
—— 3-(2-isothiocyanatoethyl)phenol 60114-06-9 C9H9NOS
3-(2-isothiocyanatoethyl)phenol
—— 2-(3,5-dihydroxyphenyl)-5-methoxypentane 99237-50-0 C12H18O3
2-(3,5-dihydroxyphenyl)-5-methoxypentane
—— 1,4-dimethoxy-2,5-bis(methoxymethoxy)-6-butyl-3{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-hydroxyphenyl]pentyl}benzene 99622-15-8 C33H52O13
1,4-dimethoxy-2,5-bis(methoxymethoxy)-6-butyl-3{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-hydroxyphenyl]pentyl}benzene
—— 2-(3,4-Dimethoxyphenyl)ethyl 5-nitrofuran-2-carboxylate 1419943-22-8 C15H15NO7
2-(3,4-Dimethoxyphenyl)ethyl 5-nitrofuran-2-carboxylate
—— 2-(furan-2-ylmethyl)iminomethyl-4-bromo phenol 418774-14-8 C12H10BrNO2
2-(furan-2-ylmethyl)iminomethyl-4-bromo phenol
—— N-[2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide 342901-86-4 C27H29Br2NO5
N-[2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide
—— 5-bromo-2-chloro-4-nitrophenol 48125-11-7 C6H3BrClNO3
5-bromo-2-chloro-4-nitrophenol
—— 4-nitro-2-(1H-1,2,4-triazol-5-yliminomethyl)phenol 202118-42-1 C9H7N5O3
4-nitro-2-(1H-1,2,4-triazol-5-yliminomethyl)phenol
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(methylsulfanyl)-4,5-dihydro-1,3-thiazol-4-one 1181081-70-8 C11H8FNO2S2
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(methylsulfanyl)-4,5-dihydro-1,3-thiazol-4-one
—— (5Z)-5-(3,5-dibromo-4-fluoro-2-hydroxybenzylidene)-2-(methylthio)thiazol-4(5H)-one 1181083-33-9 C11H6Br2FNO2S2
(5Z)-5-(3,5-dibromo-4-fluoro-2-hydroxybenzylidene)-2-(methylthio)thiazol-4(5H)-one
—— (5Z)-5-(5-bromo-4-fluoro-2-hydroxybenzylidene)-2-(methylthio)thiazol-4(5H)-one 1181083-32-8 C11H7BrFNO2S2
(5Z)-5-(5-bromo-4-fluoro-2-hydroxybenzylidene)-2-(methylthio)thiazol-4(5H)-one
—— (5Z)-2-(1,2-diazinan-1-yl)-5-[(3,5-dibromo-4-fluoro-2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one 1181082-15-4 C14H12Br2FN3O2S
(5Z)-2-(1,2-diazinan-1-yl)-5-[(3,5-dibromo-4-fluoro-2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one
—— (5Z)-5-[(5-bromo-4-fluoro-2-hydroxyphenyl)methylidene]-2-(1,2-diazinan-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181082-14-3 C14H13BrFN3O2S
(5Z)-5-[(5-bromo-4-fluoro-2-hydroxyphenyl)methylidene]-2-(1,2-diazinan-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 4-ethoxy-2,5-dimethylphenol 99172-75-5 C10H14O2
4-ethoxy-2,5-dimethylphenol
—— 2,6-diformyl-p-cresol-bis(4-phenyl thiosemicarbazone) 189126-13-4 C23H22N6OS2
2,6-diformyl-p-cresol-bis(4-phenyl thiosemicarbazone)
—— 5-(4-fluoro-2-hydroxyphenyl)furan-2-carbaldehyde 900515-33-5 C11H7FO3
5-(4-fluoro-2-hydroxyphenyl)furan-2-carbaldehyde
—— 4-n-pentyl-2-fluorophenol 78322-87-9 C11H15FO
4-n-pentyl-2-fluorophenol
—— 4,5-Dihydroxy-3-methoxy-hydrozimtsaeure-methylester (3-Methoxy-hydrokaffeesaeure-methylester) 2234-50-6 C11H14O5
4,5-Dihydroxy-3-methoxy-hydrozimtsaeure-methylester (3-Methoxy-hydrokaffeesaeure-methylester)
—— 3-nitro-4-hydroxyphenylacetyl chloride 10463-21-5 C8H6ClNO4
3-nitro-4-hydroxyphenylacetyl chloride
—— 2,4-dinitroso-5-methylresorcine 74061-37-3 C7H6N2O4
2,4-dinitroso-5-methylresorcine
—— 4-((tert-butyl(ethyl)(methyl)silyl)oxy)-3-methoxy-2-methylphenol 925451-68-9 C15H26O3Si
4-((tert-butyl(ethyl)(methyl)silyl)oxy)-3-methoxy-2-methylphenol
—— pyrrolizidinium picrate 14129-07-8 C6H3N3O7*C7H13N
pyrrolizidinium picrate
—— 2,2-dimethyl propionic acid 2-(4-tert-butylbenzyl)-3-[3-(4-hydroxy-3-methoxybenzyl)thioureido]propyl ester 289902-71-2 C28H40N2O4S
2,2-dimethyl propionic acid 2-(4-tert-butylbenzyl)-3-[3-(4-hydroxy-3-methoxybenzyl)thioureido]propyl ester
—— 3-hydroxy-4-methoxyphenylglyoxal 92765-61-2 C9H8O4
3-hydroxy-4-methoxyphenylglyoxal
—— 5-(3-hydroxy-4-methoxyphenyl)-4-(4-methoxyphenyl)isoxazole 1271728-01-8 C17H15NO4
5-(3-hydroxy-4-methoxyphenyl)-4-(4-methoxyphenyl)isoxazole
—— 2-chloro-5-hydroxy-3-methoxytoluene 78135-47-4 C8H9ClO2
2-chloro-5-hydroxy-3-methoxytoluene
—— 3,4-diamino-2-nitrophenol 147021-87-2 C6H7N3O3
3,4-diamino-2-nitrophenol
—— 3,5-dimethoxy-2,4-dinitrophenol 206120-79-8 C8H8N2O7
3,5-dimethoxy-2,4-dinitrophenol
—— 5-propylpyrogallol 861383-97-3 C9H12O3
5-propylpyrogallol
—— ethyl hydroxy(2-hydroxyphenyl)acetate 13511-31-4 C10H12O4
ethyl hydroxy(2-hydroxyphenyl)acetate
—— (5Z,5'Z)-2,2'-[piperazine-1,4-diylbis(ethane-2,1-diylimino)]bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one) 1415582-35-2 C28H30N6O4S2
(5Z,5'Z)-2,2'-[piperazine-1,4-diylbis(ethane-2,1-diylimino)]bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one)
—— 4-[(4,5-dimethyltriazol-1-yl)iminomethyl]phenol 113261-28-2 C11H12N4O
4-[(4,5-dimethyltriazol-1-yl)iminomethyl]phenol
—— 3-tert-butyl-2-hydroxy-5-nitrobenzonitrile 372137-85-4 C11H12N2O3
3-tert-butyl-2-hydroxy-5-nitrobenzonitrile
—— 4-(2-hydroxy-3-methoxy-phenyl)-butan-2-one 4221-49-2 C11H14O3
4-(2-hydroxy-3-methoxy-phenyl)-butan-2-one
—— 6-butyl-2-methoxyphenol 130223-24-4 C11H16O2
6-butyl-2-methoxyphenol
—— 3-(4-hydroxy-3-methylphenyl)propanenitrile 22516-99-0 C10H11NO
3-(4-hydroxy-3-methylphenyl)propanenitrile
—— 6-chloro-4-(3-hydroxypropyl)-2-methylphenol 839694-29-0 C10H13ClO2
6-chloro-4-(3-hydroxypropyl)-2-methylphenol
—— N-n-Butyl-N'-(2-hydroxy-3-nitrobenzoyl)-diaminoethan-1,2 86840-90-6 C13H19N3O4
N-n-Butyl-N'-(2-hydroxy-3-nitrobenzoyl)-diaminoethan-1,2
—— N-n-Butyl-N'-(2-hydroxy-5-nitrobenzoyl)-diaminoethan-1,2 86840-93-9 C13H19N3O4
N-n-Butyl-N'-(2-hydroxy-5-nitrobenzoyl)-diaminoethan-1,2
—— 1-n-Butyl-2-(2-hydroxy-5-nitrophenyl)-Δ<sup>2</sup>-imidazolin 86840-86-0 C13H17N3O3
1-n-Butyl-2-(2-hydroxy-5-nitrophenyl)-Δ<sup>2</sup>-imidazolin
—— Butyl 3-[[3-[(3-butoxy-3-oxopropyl)sulfanylmethyl]-2-hydroxy-5-methylphenyl]methylsulfanyl]propanoate 1192176-20-7 C23H36O5S2
Butyl 3-[[3-[(3-butoxy-3-oxopropyl)sulfanylmethyl]-2-hydroxy-5-methylphenyl]methylsulfanyl]propanoate
—— 4,4'-(pyrazine-2,6-diyl)diphenol 171820-09-0 C16H12N2O2
4,4'-(pyrazine-2,6-diyl)diphenol
—— Benzyl 4-(2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioate 125155-66-0 C19H22N2O3S2
Benzyl 4-(2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioate
—— (4-hydroxy-2-methyl-phenylsulfanyl)-acetic acid ethyl ester 30512-72-2 C11H14O3S
(4-hydroxy-2-methyl-phenylsulfanyl)-acetic acid ethyl ester
—— 2-(3-hydroxy-4-methoxybenzylsulfinyl)acetic acid 852285-79-1 C10H12O5S
2-(3-hydroxy-4-methoxybenzylsulfinyl)acetic acid
—— 3,3-dichloro-1-(2’-hydroxy-4’,6’-dimethoxyphenyl)prop-2-en-1-one 64964-84-7 C11H10Cl2O4
3,3-dichloro-1-(2’-hydroxy-4’,6’-dimethoxyphenyl)prop-2-en-1-one
—— dimethyl 5-(3-hydroxyphenyl)-4,6-dithianonanedioate 1040-71-7 C15H20O5S2
dimethyl 5-(3-hydroxyphenyl)-4,6-dithianonanedioate
—— [(E)-4-[3-hydroxy-2-(hydroxymethyl)-4-methoxy-5-methylphenyl]but-2-enyl] 2,2-dimethylpropanoate 351377-67-8 C18H26O5
[(E)-4-[3-hydroxy-2-(hydroxymethyl)-4-methoxy-5-methylphenyl]but-2-enyl] 2,2-dimethylpropanoate
—— Phenol, 2-[(1R,2S)-1,2-dimethyl-3-methylenecyclopentyl]-5-methyl- 63181-28-2 C15H20O
Phenol, 2-[(1R,2S)-1,2-dimethyl-3-methylenecyclopentyl]-5-methyl-
—— 1-(4-hydroxy-3-nitrophenyl)-cyclopropanecarboxylic acid methyl ester 945244-02-0 C11H11NO5
1-(4-hydroxy-3-nitrophenyl)-cyclopropanecarboxylic acid methyl ester