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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
—— 4,6-bis[5-(4-methoxyphenyl)-1,2-oxazol-3-yl]benzene-1,3-diol 137369-35-8 C26H20N2O6
4,6-bis[5-(4-methoxyphenyl)-1,2-oxazol-3-yl]benzene-1,3-diol
—— 4-Brom-2-methoxy-5-(2-nitro-prop-1-enyl)-phenol 7396-74-9 C10H10BrNO4
4-Brom-2-methoxy-5-(2-nitro-prop-1-enyl)-phenol
—— 4-bromo-2-[(Z)-4-hydroxy-3-methylbut-2-enyl]-6-methoxyphenol 866535-33-3 C12H15BrO3
4-bromo-2-[(Z)-4-hydroxy-3-methylbut-2-enyl]-6-methoxyphenol
—— 2-(benzyloxy)-4-bromo-6-methoxyphenol 1395922-41-4 C14H13BrO3
2-(benzyloxy)-4-bromo-6-methoxyphenol
—— 4-Bromo-2-(1-hydroxyprop-2-en-1-yl)-6-methoxyphenol 1253197-90-8 C10H11BrO3
4-Bromo-2-(1-hydroxyprop-2-en-1-yl)-6-methoxyphenol
—— 4-(5-bromo-2-hydroxy-3-methoxyphenyl)-3-methyl-1,4,7,8-tetrahydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one 1309571-39-8 C16H14BrN3O4
4-(5-bromo-2-hydroxy-3-methoxyphenyl)-3-methyl-1,4,7,8-tetrahydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one
—— 2-(2-hydroxy-3-methoxyhydrocinnamoyl)-1,3-cyclopentanedione 37748-01-9 C15H16O5
2-(2-hydroxy-3-methoxyhydrocinnamoyl)-1,3-cyclopentanedione
—— 5-(benzo[b]thiophen-3-yl)-2-hydroxy-3-methoxybenzaldehyde 1093118-59-2 C16H12O3S
5-(benzo[b]thiophen-3-yl)-2-hydroxy-3-methoxybenzaldehyde
—— 2-{(E)-[(2-chlorophenyl)imino]methyl}-6-methoxyphenol 112628-73-6 C14H12ClNO2
2-{(E)-[(2-chlorophenyl)imino]methyl}-6-methoxyphenol
—— 2-hydroxy-3-methoxybenzaldehyde O-methyloxime 859738-08-2 C9H11NO3
2-hydroxy-3-methoxybenzaldehyde O-methyloxime
—— vanillinidene-2-methyl-1-aminobenzene 19264-42-7 C15H15NO2
vanillinidene-2-methyl-1-aminobenzene
—— 4-bromo-2-hydroxy-3-methoxybenzaldehyde 1427439-23-3 C8H7BrO3
4-bromo-2-hydroxy-3-methoxybenzaldehyde
—— (E)-3-(2-hydroxy-3-methoxybenzylidene)-6-chloroindolin-2-one 1612883-04-1 C16H12ClNO3
(E)-3-(2-hydroxy-3-methoxybenzylidene)-6-chloroindolin-2-one
—— 3-[(5-cyano-1H-indol-3-yl)(2-hydroxy-3-methoxyphenyl)methyl]-1H-indole-5-carbonitrile 1429404-72-7 C26H18N4O2
3-[(5-cyano-1H-indol-3-yl)(2-hydroxy-3-methoxyphenyl)methyl]-1H-indole-5-carbonitrile
—— (E)-2-(hydroxyimino)-3-(4-hydroxyphenyl)-N-(2-mercaptoethyl)propanamide 1356930-03-4 C11H14N2O3S
(E)-2-(hydroxyimino)-3-(4-hydroxyphenyl)-N-(2-mercaptoethyl)propanamide
—— 3-hydroxy-4-(4-hydroxyphenyl)-5-pentylfuran-2(5H)-one 1198427-20-1 C15H18O4
3-hydroxy-4-(4-hydroxyphenyl)-5-pentylfuran-2(5H)-one
—— 2-(2,2,2-trifluoroethyl)phenol 440659-12-1 C8H7F3O
2-(2,2,2-trifluoroethyl)phenol
—— 2-(1-hydroxy-2,2,2-trifluoroethyl)phenol 201996-23-8 C8H7F3O2
2-(1-hydroxy-2,2,2-trifluoroethyl)phenol
—— stephanosporin 350985-53-4 C10H10ClN3O6
stephanosporin
—— 2,6-dimethoxy-4-[(E)-3-phenoxyprop-1-enyl]phenol 94930-86-6 C17H18O4
2,6-dimethoxy-4-[(E)-3-phenoxyprop-1-enyl]phenol
—— 3-methylsulfanyl-4-nitro-phenol 771-94-8 C7H7NO3S
3-methylsulfanyl-4-nitro-phenol
—— 2-methylthio-5-nitrophenol 772-42-9 C7H7NO3S
2-methylthio-5-nitrophenol
—— 2-(2,2-bis(trifluoromethylsulfonyl)ethyl)phenol 1360543-91-4 C10H8F6O5S2
2-(2,2-bis(trifluoromethylsulfonyl)ethyl)phenol
—— 4-(2,2-bis(trifluoromethylsulfonyl)ethyl)phenol 1360543-89-0 C10H8F6O5S2
4-(2,2-bis(trifluoromethylsulfonyl)ethyl)phenol
—— 2-O-methyl-1-O-((2-(3,4,5-trimethoxy)phenyl))ethyl glycerin 128401-04-7 C15H24O6
2-O-methyl-1-O-((2-(3,4,5-trimethoxy)phenyl))ethyl glycerin
—— 5-[[3,5-Bis[(4-ethenylphenyl)methoxy]phenyl]methoxy]-3-tert-butyl-2-hydroxybenzaldehyde 360784-98-1 C36H36O5
5-[[3,5-Bis[(4-ethenylphenyl)methoxy]phenyl]methoxy]-3-tert-butyl-2-hydroxybenzaldehyde
—— 2-Hydroxy-3,5-dimethoxy-1-t-butyl-benzol 26037-86-5 C12H18O3
2-Hydroxy-3,5-dimethoxy-1-t-butyl-benzol
—— tert-butyl-2-methoxyphenol 18515-07-6 C11H16O2
tert-butyl-2-methoxyphenol
—— 4-Benzyloxy-2,6-bis-morpholinomethyl-phenol 95434-45-0 C23H30N2O4
4-Benzyloxy-2,6-bis-morpholinomethyl-phenol
—— 2-Hydroxy-3-methoxy-5-methylbenzylalkohol 7452-08-6 C9H12O3
2-Hydroxy-3-methoxy-5-methylbenzylalkohol
—— 3-(4-hydroxy-3-iodophenyl)propanoate 53937-20-5 C10H11IO3
3-(4-hydroxy-3-iodophenyl)propanoate
—— 4-cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran 179420-74-7 C12H13NO2
4-cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran
—— (4-Hydroxy-3-methoxy-5-methylbenzyl)-methylaether 60824-65-9 C10H14O3
(4-Hydroxy-3-methoxy-5-methylbenzyl)-methylaether
—— 1-(4-Hydroxyphenyl)-6-phenylhexane 113795-46-3 C18H22O
1-(4-Hydroxyphenyl)-6-phenylhexane
—— ethyl 6-(4-hydroxyphenoxy)hexanoate 1365836-17-4 C14H20O4
ethyl 6-(4-hydroxyphenoxy)hexanoate
—— 2,5,6-tribromovanillin 854873-00-0 C8H5Br3O3
2,5,6-tribromovanillin
—— 2-<(p-hydroxyphenyl)methyl>-4-methylimidazole 102151-86-0 C11H12N2O
2-<(p-hydroxyphenyl)methyl>-4-methylimidazole
—— 4-bromo-2-<2-(p-hydroxyphenyl)ethyl>-5-(trifluoromethyl)imidazole 102151-98-4 C11H11BrN2O
4-bromo-2-<2-(p-hydroxyphenyl)ethyl>-5-(trifluoromethyl)imidazole
—— 2-<2-(p-hydroxyphenyl)ethyl>-4-(2-thienyl)imidazole 102151-95-1 C15H14N2OS
2-<2-(p-hydroxyphenyl)ethyl>-4-(2-thienyl)imidazole
—— 2-(4-hydroxyphenoxy)acetamide 22446-14-6 C8H9NO3
2-(4-hydroxyphenoxy)acetamide
—— 4-{[2-(4-hydroxyphenoxy)ethyl]-[1,2,4]triazol-4-yl-amino}benzonitrile 537674-31-0 C17H15N5O2
4-{[2-(4-hydroxyphenoxy)ethyl]-[1,2,4]triazol-4-yl-amino}benzonitrile
—— N-<2-(4-hydroxyphenoxy)ethyl>acetamide 140662-59-5 C10H13NO3
N-<2-(4-hydroxyphenoxy)ethyl>acetamide
—— 4-bromo-3-fluoro-2-nitrophenol 889939-22-4 C6H3BrFNO3
4-bromo-3-fluoro-2-nitrophenol
—— 3-Tert-butyl-4-dodecoxyphenol 140466-95-1 C22H38O2
3-Tert-butyl-4-dodecoxyphenol
—— 3-dodecyloxy-2-methoxyphenol 130442-18-1 C19H32O3
3-dodecyloxy-2-methoxyphenol
—— 4-methoxy-3-propylphenol 141989-05-1 C10H14O2
4-methoxy-3-propylphenol
—— 2-ethyl-4-tetradecylphenol 118469-77-5 C22H38O
2-ethyl-4-tetradecylphenol
—— 2-Tert-butyl-4-dodecoxyphenol 3251-44-3 C22H38O2
2-Tert-butyl-4-dodecoxyphenol
—— 3,5-bis(mercaptomethyl)phenol 135990-07-7 C8H10OS2
3,5-bis(mercaptomethyl)phenol
—— diethyl (5-methyl-2-thienyl)-(4-hydroxy-1-phenyl)-methyl-phosphonate 141191-30-2 C16H21O4PS
diethyl (5-methyl-2-thienyl)-(4-hydroxy-1-phenyl)-methyl-phosphonate