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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
—— 5,11-dichlorotetracyclo[13.3.1.13,7.19,13]henicosa-1(19),3(21),4,6,9,11,13(20),15,17-nonaene-19,20,21-triol 83142-72-7 C21H16Cl2O3
5,11-dichlorotetracyclo[13.3.1.13,7.19,13]henicosa-1(19),3(21),4,6,9,11,13(20),15,17-nonaene-19,20,21-triol
—— 3-(2,2-dimethoxyethyl)-2-iodo-6-methoxyphenol 916225-97-3 C11H15IO4
3-(2,2-dimethoxyethyl)-2-iodo-6-methoxyphenol
—— 1-Butyl-3-{3-[(3-butyl-thioureido)-methyl]-2-hydroxy-benzyl}-thiourea 321898-65-1 C18H30N4OS2
1-Butyl-3-{3-[(3-butyl-thioureido)-methyl]-2-hydroxy-benzyl}-thiourea
—— 5-bromo-3-methoxy-2-hydroxybenzaldehyde thiosemicarbazone 119748-38-8 C9H10BrN3O2S
5-bromo-3-methoxy-2-hydroxybenzaldehyde thiosemicarbazone
—— 4-(4-(4-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)pyridin-3-ol 1616763-20-2 C20H13FN4O
4-(4-(4-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)pyridin-3-ol
—— 4-phenyl-N'-(2,3,4-trihydroxybenzyl)butanehydrazide —— C17H20N2O4
4-phenyl-N'-(2,3,4-trihydroxybenzyl)butanehydrazide
—— 4-[1,3,4]thiadiazol-2-yl-phenol —— C8H6N2OS
4-[1,3,4]thiadiazol-2-yl-phenol
—— octanedioic acid bis-(2,3-dihydroxybenzylamide) —— C22H28N2O6
octanedioic acid bis-(2,3-dihydroxybenzylamide)
—— (Z)-5-(3,5-dibromo-4-hydroxybenzylidene)-2-(methylsulfanyl)thiazol-4-one —— C11H7Br2NO2S2
(Z)-5-(3,5-dibromo-4-hydroxybenzylidene)-2-(methylsulfanyl)thiazol-4-one
—— N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-nitrofuran-2-carboxamide —— C16H15N5O6
N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-nitrofuran-2-carboxamide
—— N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-6-(4-methoxyphenyl)imidazo [2,1-b]thiazole-3-carboxamide —— C24H22N6O4S
N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-6-(4-methoxyphenyl)imidazo [2,1-b]thiazole-3-carboxamide
—— 6-(4-fluorophenyl)-N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)imidazo [2,1-b]thiazole-3-carboxamide —— C23H19FN6O3S
6-(4-fluorophenyl)-N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)imidazo [2,1-b]thiazole-3-carboxamide
—— N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)benzo[d]imidazo[2,1-b]thiazole-2-carboxamide —— C21H18N6O3S
N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)benzo[d]imidazo[2,1-b]thiazole-2-carboxamide
—— (5S)-4-allyloxy-5-(p-hydroxybenzyl)pyrrolin-2-one —— C14H15NO3
(5S)-4-allyloxy-5-(p-hydroxybenzyl)pyrrolin-2-one
—— 4-hydroxy-6-hydroxymethyl-3-phenylthiomethoxynitrobenzene —— C14H13NO5S
4-hydroxy-6-hydroxymethyl-3-phenylthiomethoxynitrobenzene
—— 4-ethylthio-3-hydroxy-6-hydroxymethylnitrobenzene —— C9H11NO4S
4-ethylthio-3-hydroxy-6-hydroxymethylnitrobenzene
—— 5-butyl-2,4-dihydro-4-(4-hydroxybenzyl)-3H-1,2,4-triazole-3-thione —— C13H17N3OS
5-butyl-2,4-dihydro-4-(4-hydroxybenzyl)-3H-1,2,4-triazole-3-thione
—— 3-(2-fluoro-4-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil —— C12H8F4N2O3
3-(2-fluoro-4-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil
—— 4-methoxy-(E,E)-2,6-bis(3-methoxy-4-hydroxystyryl)pyridine —— C24H23NO5
4-methoxy-(E,E)-2,6-bis(3-methoxy-4-hydroxystyryl)pyridine
—— 2,4-difluoro-6-methylphenol —— C7H6F2O
2,4-difluoro-6-methylphenol
—— pyridine-2,6-dicarboxylic acid bis-vanillylidenehydrazide —— C23H21N5O6
pyridine-2,6-dicarboxylic acid bis-vanillylidenehydrazide
—— 1-(3,4-dihydroxybenzyl)-1,2,3,6-tetrahydropyridine —— C12H15NO2
1-(3,4-dihydroxybenzyl)-1,2,3,6-tetrahydropyridine
—— 2-(4-hydroxybenzyl)pyrrole —— C11H11NO
2-(4-hydroxybenzyl)pyrrole
—— 2-dimethylamino-4-(2'-hydroxy-5'-methylphenyl)-thiazole —— C12H14N2OS
2-dimethylamino-4-(2'-hydroxy-5'-methylphenyl)-thiazole
—— sinapyl acetate —— C13H16O5
sinapyl acetate
—— (+)-ipalbidine —— C15H19NO
(+)-ipalbidine
—— 2-[{[(6-methylpyridin-2-yl)methyl](pyridyn-2-ylmethyl)amino}methyl]-4-nitrophenol —— C20H20N4O3
2-[{[(6-methylpyridin-2-yl)methyl](pyridyn-2-ylmethyl)amino}methyl]-4-nitrophenol
—— 2,6-dimethoxy-4-(3-methoxypropyl)phenol —— C12H18O4
2,6-dimethoxy-4-(3-methoxypropyl)phenol
—— (E)-4,4'-(but-2-ene-1,4-diyl)diphenol —— C16H16O2
(E)-4,4'-(but-2-ene-1,4-diyl)diphenol
—— (-)-2-hydroxy-2'-hydroxymethyl-3,4-dimethoxymethoxymethyl-4',5'-methylenedioxy-1,1'-biphenyl —— C19H22O8
(-)-2-hydroxy-2'-hydroxymethyl-3,4-dimethoxymethoxymethyl-4',5'-methylenedioxy-1,1'-biphenyl
—— 4-[diallyl(ethoxy)silyl]phenol —— C14H20O2Si
4-[diallyl(ethoxy)silyl]phenol
—— 5-bromo-2-N-[(4-hydroxy-3-fluorophenyl)]-4-N-[(tetrahydrofuran-2-yl)methyl]pyrimidine-2,4-diamine —— C15H16BrFN4O2
5-bromo-2-N-[(4-hydroxy-3-fluorophenyl)]-4-N-[(tetrahydrofuran-2-yl)methyl]pyrimidine-2,4-diamine
—— 1-(5-(5-chloro-2-hydroxy-phenyl)-3-methyl-4,5-dihydro-pyrazol-1-yl)ethanone-2-imidazole —— C15H15ClN4O2
1-(5-(5-chloro-2-hydroxy-phenyl)-3-methyl-4,5-dihydro-pyrazol-1-yl)ethanone-2-imidazole
—— tert-butyl (trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate —— C14H19NO3
tert-butyl (trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate
—— 3-(1-methylcyclopropyl)phenol —— C10H12O
3-(1-methylcyclopropyl)phenol
—— 4-bromo-2-dodecylphenol —— C18H29BrO
4-bromo-2-dodecylphenol
—— 4-hydroxy-3-phenylthiomethoxynitrobenzene —— C13H11NO4S
4-hydroxy-3-phenylthiomethoxynitrobenzene
—— (±)-3-(1-(dimethylamino)ethyl)-5-methoxyphenol —— C11H17NO2
(±)-3-(1-(dimethylamino)ethyl)-5-methoxyphenol
—— 12-((2-hydroxy-5-ethoxybenzyl)oxy)dodecanoic acid ethyl ester —— C23H38O5
12-((2-hydroxy-5-ethoxybenzyl)oxy)dodecanoic acid ethyl ester
—— 2,6-dipropyl-4-nitrophenol —— C12H17NO3
2,6-dipropyl-4-nitrophenol
—— [4-(Benzyloxy)phenethoxy](tert-butyl)dimethylsilane —— C21H30O2Si
[4-(Benzyloxy)phenethoxy](tert-butyl)dimethylsilane
—— 2-[4'-(triethylsilyloxy)phenyl]ethanol —— C14H24O2Si
2-[4'-(triethylsilyloxy)phenyl]ethanol
—— jiangrine D —— C17H21NO5
jiangrine D
—— jiangrine C —— C17H21NO5
jiangrine C
—— (3S,4E)-4-formyl-3-(2-hydroxyethyl)hex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester —— C17H22O5
(3S,4E)-4-formyl-3-(2-hydroxyethyl)hex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester
—— 4-(2-hydroxyethyl)-2-nitro-5-n-octylphenol —— C16H25NO4
4-(2-hydroxyethyl)-2-nitro-5-n-octylphenol
—— 11,23-dimethyl-5-tert-butyl-15,19-dithiatetracyclo[19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>]heptacosa-1(24),3(26),4,6,9(27),10,12,21(25),22-nonaene-25,26,27-triol —— C31H38O3S2
11,23-dimethyl-5-tert-butyl-15,19-dithiatetracyclo[19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>]heptacosa-1(24),3(26),4,6,9(27),10,12,21(25),22-nonaene-25,26,27-triol
—— 2,6-bis((1H-imidazol-1-yl)methyl)-4-methylphenol —— C15H16N4O
2,6-bis((1H-imidazol-1-yl)methyl)-4-methylphenol
—— 2,3-dihydro-6-(3-(4-(2-hydroxyethyl)phenoxy)propyl)-5-benzofuranol —— C19H22O4
2,3-dihydro-6-(3-(4-(2-hydroxyethyl)phenoxy)propyl)-5-benzofuranol
—— (S)-2-(4-(3-(1, 1-dimethylethyl)-2-phenyl-5-oxazolidinylmethoxy)phenyl)ethanol —— C22H29NO3
(S)-2-(4-(3-(1, 1-dimethylethyl)-2-phenyl-5-oxazolidinylmethoxy)phenyl)ethanol