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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-(4-chlorophenyl)-3-(4-hydroxy-2-nitro-phenyl)urea 862014-82-2 C13H10ClN3O4
1-(4-chlorophenyl)-3-(4-hydroxy-2-nitro-phenyl)urea
—— 4-bromo-6-(hydroxymethyl)-3-methoxy-2-methylphenol 946860-99-7 C9H11BrO3
4-bromo-6-(hydroxymethyl)-3-methoxy-2-methylphenol
—— S-bromo-2-hydroxy-4-methoxy-3-methylbenzaldehyde 946860-98-6 C9H9BrO3
S-bromo-2-hydroxy-4-methoxy-3-methylbenzaldehyde
—— (4-allyl-3-hydroxyphenyl)acetic acid methyl ester 950514-52-0 C12H14O3
(4-allyl-3-hydroxyphenyl)acetic acid methyl ester
—— (2-allyl-3-hydroxyphenyl)acetic acid methyl ester 950514-53-1 C12H14O3
(2-allyl-3-hydroxyphenyl)acetic acid methyl ester
—— 6-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one 515141-37-4 C19H13ClN2O3S
6-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one
—— trimethylsilylcresol 1443366-07-1 C10H16OSi
trimethylsilylcresol
—— Ethyl 5-[(3-hydroxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-4-carboxylate 744195-93-5 C15H19NO3
Ethyl 5-[(3-hydroxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-4-carboxylate
—— 2-[1-(1H-1,2,3-benzotriazol-1-yl)ethyl]-4-nitrophenol 1379588-06-3 C14H12N4O3
2-[1-(1H-1,2,3-benzotriazol-1-yl)ethyl]-4-nitrophenol
—— 2-[(4-hydroxyphenyl)methyl]-3-oxobutanoic acid N-methylamide 361576-49-0 C12H15NO3
2-[(4-hydroxyphenyl)methyl]-3-oxobutanoic acid N-methylamide
—— 1-(3-Hydroxy-4-methoxyphenyl)cyclopropanecarboxylic acid 936728-04-0 C11H12O4
1-(3-Hydroxy-4-methoxyphenyl)cyclopropanecarboxylic acid
—— 1-(3-Chloro-4-hydroxyphenyl)cyclopropanecarboxylic acid 945244-31-5 C10H9ClO3
1-(3-Chloro-4-hydroxyphenyl)cyclopropanecarboxylic acid
—— 2-allyl-6-fluoro-3-methylphenol 1256257-63-2 C10H11FO
2-allyl-6-fluoro-3-methylphenol
—— 3-chloro-5-hydroxyphenethyl acetate 1042023-78-8 C10H11ClO3
3-chloro-5-hydroxyphenethyl acetate
—— 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methoxyacetamide 1207549-44-7 C19H20N2O6
2-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-methoxyacetamide
—— (4-bromo-2-chloro-5-hydroxyphenyl)boronic acid 1046861-50-0 C6H5BBrClO3
(4-bromo-2-chloro-5-hydroxyphenyl)boronic acid
—— tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate 1141782-09-3 C14H21NO4
tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate
—— 5-(4-Fluoro-3-hydroxyphenyl)-4,4-dimethyl-2,4-dihydropyrazol-3-one 1010801-09-8 C11H11FN2O2
5-(4-Fluoro-3-hydroxyphenyl)-4,4-dimethyl-2,4-dihydropyrazol-3-one
—— 5-(2-Fluoro-3-hydroxyphenyl)-4,4-dimethyl-2,4-dihydropyrazol-3-one 1010801-12-3 C11H11FN2O2
5-(2-Fluoro-3-hydroxyphenyl)-4,4-dimethyl-2,4-dihydropyrazol-3-one
—— 2,3-difluoro-4-methyl-5-nitro-phenol 1232506-08-9 C7H5F2NO3
2,3-difluoro-4-methyl-5-nitro-phenol
—— 2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetic acid 1233531-09-3 C13H15NO5
2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetic acid
—— methyl 2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetate 1233531-10-6 C14H17NO5
methyl 2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetate
—— 3-Cycloheptyl-1,1-dioxo-1-benzothiophen-6-ol 1032791-46-0 C15H18O3S
3-Cycloheptyl-1,1-dioxo-1-benzothiophen-6-ol
—— 2,3-difluoro-4-methyl-6-nitrophenol 1134197-64-0 C7H5F2NO3
2,3-difluoro-4-methyl-6-nitrophenol
—— 4-(4-hydroxyphenyl)thiophene-3-carbonitrile 1235035-55-8 C11H7NOS
4-(4-hydroxyphenyl)thiophene-3-carbonitrile
—— 2-(3,5-difluoro-4-hydroxybenzyl)cyclopropanecarboxylic acid ethyl ester 1224103-76-7 C13H14F2O3
2-(3,5-difluoro-4-hydroxybenzyl)cyclopropanecarboxylic acid ethyl ester
—— 3-fluoro-2-(3-hydroxypropyl)-6-methoxyphenol 951796-88-6 C10H13FO3
3-fluoro-2-(3-hydroxypropyl)-6-methoxyphenol
—— 2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoic acid 1246213-44-4 C14H19NO5
2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoic acid
—— 3-Methoxy-2-nitrosophenol 88331-64-0 C7H7NO3
3-Methoxy-2-nitrosophenol
—— 2-but-1-ynyl-5-fluoro-phenol 1170264-42-2 C10H9FO
2-but-1-ynyl-5-fluoro-phenol
—— 5-Chloro-I+/-,2-dihydroxybenzeneacetic acid 73289-76-6 C8H7ClO4
5-Chloro-I+/-,2-dihydroxybenzeneacetic acid
—— 3-(3-fluoro-4-hydroxy-5-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one 910814-29-8 C21H23FO3S
3-(3-fluoro-4-hydroxy-5-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one
—— 5-chloro-2-isopropyl-4-methoxy-phenol 865305-19-7 C10H13ClO2
5-chloro-2-isopropyl-4-methoxy-phenol
—— 3-nitro-5-ethylcatechol 71608-02-1 C8H9NO4
3-nitro-5-ethylcatechol
—— Decyl 5-hydroxy-6-[2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl]-1,3-dithian-2-yl]-3-oxohexanoate 1139819-31-0 C30H48O7S2
Decyl 5-hydroxy-6-[2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl]-1,3-dithian-2-yl]-3-oxohexanoate
—— 2-fluoro-4-trimethylsilanyl-phenol 1030382-91-2 C9H13FOSi
2-fluoro-4-trimethylsilanyl-phenol
—— 3-chloro-2-(3-hydroxypropyl)phenol. 1154740-52-9 C9H11ClO2
3-chloro-2-(3-hydroxypropyl)phenol.
—— 5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol 1000002-66-3 C16H13ClN2O2
5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol
—— 5-[5-(4-chloro-phenyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol 1000002-71-0 C15H11ClN2O2
5-[5-(4-chloro-phenyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol
—— 2,6-Diamino-4-methoxyphenol 38213-77-3 C7H10N2O2
2,6-Diamino-4-methoxyphenol
—— 4-hydroxy-2,6 dimethyl-dihydro-ethyl cinnamate 729590-61-8 C13H18O3
4-hydroxy-2,6 dimethyl-dihydro-ethyl cinnamate
—— 2-[[2-(4-Methoxyphenyl)ethoxy]methyl]pyrrolidine 933758-82-8 C14H21NO2
2-[[2-(4-Methoxyphenyl)ethoxy]methyl]pyrrolidine
—— 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(3-hydroxy-4-nitrophenyl)ethoxy]carbonyl]hydrazine 881404-76-8 C13H18ClN3O9S2
1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(3-hydroxy-4-nitrophenyl)ethoxy]carbonyl]hydrazine
—— 2-methoxy-4-({6-[4-(2-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}ethynyl)phenol 1029359-62-3 C24H22FN3O3
2-methoxy-4-({6-[4-(2-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}ethynyl)phenol
—— 2-methyl-4-(trimethylsilyl)phenol 58933-97-4 C10H16OSi
2-methyl-4-(trimethylsilyl)phenol
—— 4-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-5-fluoro-2-methoxy-phenol 1036383-61-5 C15H12ClFN2O2
4-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-5-fluoro-2-methoxy-phenol
—— 4-Fluoro-5-iodo-2-methylphenol 900175-53-3 C7H6FIO
4-Fluoro-5-iodo-2-methylphenol
—— 4-formyl-5-hydroxy-2-methoxy-N,N-diethylaniline 1034887-51-8 C12H17NO3
4-formyl-5-hydroxy-2-methoxy-N,N-diethylaniline
—— 5,11,17,23-Tetrakis(benzylideneamino)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol 934351-74-3 C56H44N4O4
5,11,17,23-Tetrakis(benzylideneamino)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— (I+/-S)-I+/--Amino-3-bromo-2-fluoro-6-hydroxy-5-methoxybenzeneacetic acid 1213379-15-7 C9H9BrFNO4
(I+/-S)-I+/--Amino-3-bromo-2-fluoro-6-hydroxy-5-methoxybenzeneacetic acid