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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-bromo-2,5-dimethyl-1,4-hydroquinone 857974-40-4 C8H9BrO2
3-bromo-2,5-dimethyl-1,4-hydroquinone
—— p-Benzochinon*Resorcin 26734-94-1 C6H4O2*C6H6O2
p-Benzochinon*Resorcin
—— 4,5-dihydroxy-2,3-dimethoxybenzaldehyde 82835-24-3 C9H10O5
4,5-dihydroxy-2,3-dimethoxybenzaldehyde
—— 5-chloro-1,2-dihydroxy-3,4-dimethoxybenzene 109765-55-1 C8H9ClO4
5-chloro-1,2-dihydroxy-3,4-dimethoxybenzene
—— 2,3-Dibrom-6-hydroxy-toluol 55289-37-7 C7H6Br2O
2,3-Dibrom-6-hydroxy-toluol
—— 2-(perfluorohexyl)hydroquinone 135957-85-6 C12H5F13O2
2-(perfluorohexyl)hydroquinone
—— 6-amino-1,2,4-trioxy-benzene 1020719-19-0 C6H7NO3
6-amino-1,2,4-trioxy-benzene
—— 4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexyl]-2,6-dimethoxy-phenol 199851-14-4 C39H69NO9Si3
4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexyl]-2,6-dimethoxy-phenol
—— (3,4-Dihydroxyphenyl)-2-methoxyethanol 64349-53-7 C9H12O4
(3,4-Dihydroxyphenyl)-2-methoxyethanol
—— 2-hydroxy-3-[(tert-butyldimethylsilyl)oxy]-4-methoxybenzaldehyde 881877-68-5 C14H22O4Si
2-hydroxy-3-[(tert-butyldimethylsilyl)oxy]-4-methoxybenzaldehyde
—— 2-hydroxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde 1242060-69-0 C24H26O4Si
2-hydroxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde
—— 2-Allyloxy-3-hydroxy-4-methoxy-benzaldehyde 84018-96-2 C11H12O4
2-Allyloxy-3-hydroxy-4-methoxy-benzaldehyde
—— 3-benzyl-4-o-hydroxybenzylidenamino-4,5-dihydro-1,2,4-triazol-5-one 137182-51-5 C16H14N4O2
3-benzyl-4-o-hydroxybenzylidenamino-4,5-dihydro-1,2,4-triazol-5-one
—— (2S)-1-Amino-3-(4-hydroxy-phenoxy)-propan-2-ol 208459-22-7 C9H13NO3
(2S)-1-Amino-3-(4-hydroxy-phenoxy)-propan-2-ol
—— 2-ethyl-3,5,6-trimethoxy-phenol 103852-76-2 C11H16O4
2-ethyl-3,5,6-trimethoxy-phenol
—— 2-amino-5-chloro-4-hydroxy-3-methoxy-benzaldehyde 185416-61-9 C8H8ClNO3
2-amino-5-chloro-4-hydroxy-3-methoxy-benzaldehyde
—— 4-Benzyloxy-2-vinylphenol 403612-35-1 C15H14O2
4-Benzyloxy-2-vinylphenol
—— 2-amino-6-bromo-4-hydroxy-3-methoxy-benzaldehyde 500308-51-0 C8H8BrNO3
2-amino-6-bromo-4-hydroxy-3-methoxy-benzaldehyde
—— 3-bromo-2-chloro-4-hydroxy-5-methoxy-benzaldehyde 75024-38-3 C8H6BrClO3
3-bromo-2-chloro-4-hydroxy-5-methoxy-benzaldehyde
—— 1-(4-hydroxy-3-nitrophenyl)ethanol 134779-31-0 C8H9NO4
1-(4-hydroxy-3-nitrophenyl)ethanol
—— 4-(5,6-Dihydro-4H-pyran-2-yl)-phenol 143144-60-9 C11H12O2
4-(5,6-Dihydro-4H-pyran-2-yl)-phenol
—— (2,3-dihydroxy-benzyl)-carbamic acid tert-butyl ester 756900-98-8 C12H17NO4
(2,3-dihydroxy-benzyl)-carbamic acid tert-butyl ester
—— 2-amino-3-chloro-5-methoxyphenol 440123-51-3 C7H8ClNO2
2-amino-3-chloro-5-methoxyphenol
—— sodium o-hydroxyphenthiolate —— C6H5OS*Na
sodium o-hydroxyphenthiolate
—— bromo-bis-(3-hydroxy-phenyl)-arsine 6308-60-7 C12H10AsBrO2
bromo-bis-(3-hydroxy-phenyl)-arsine
—— bis-(3-hydroxy-phenyl)-arsinic acid 6308-62-9 C12H11AsO4
bis-(3-hydroxy-phenyl)-arsinic acid
—— 4-heptafluoroisopropyl-3-methylphenol 353273-03-7 C10H7F7O
4-heptafluoroisopropyl-3-methylphenol
—— 4-formyl-3-(2-oxoethyl)-4-hexenoic acid 2-(4-hydroxyphenyl)ethyl ester 151194-92-2 C17H20O5
4-formyl-3-(2-oxoethyl)-4-hexenoic acid 2-(4-hydroxyphenyl)ethyl ester
—— 1-(4-hydroxy-2-methylphenyl)-3-methyl-2-buten-1-one 142337-50-6 C12H14O2
1-(4-hydroxy-2-methylphenyl)-3-methyl-2-buten-1-one
—— 1-(2-hydroxy-4-methylphenyl)-3-methyl-2-buten-1-one 142337-65-3 C12H14O2
1-(2-hydroxy-4-methylphenyl)-3-methyl-2-buten-1-one
—— 5-Amino-4-fluoro-2-(1-methylcycloheptyl)phenol 873055-50-6 C14H20FNO
5-Amino-4-fluoro-2-(1-methylcycloheptyl)phenol
—— 4-n-butyl-2-fluoro-5-methylphenol 1256550-19-2 C11H15FO
4-n-butyl-2-fluoro-5-methylphenol
—— 4-butyl-5-methylbenzene-1,2-diol 1256550-15-8 C11H16O2
4-butyl-5-methylbenzene-1,2-diol
—— methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate 922151-72-2 C11H12O3
methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate
—— 3-methyl-2-(tetrahydro-2H-pyran-2-yl)phenol 117658-44-3 C12H16O2
3-methyl-2-(tetrahydro-2H-pyran-2-yl)phenol
—— 4-bromo-2-(5-propylisoxazol-3-yl)phenol 1375102-95-6 C12H12BrNO2
4-bromo-2-(5-propylisoxazol-3-yl)phenol
—— 4-allyl-2-(5-propylisoxazol-3-yl)phenol 1375102-93-4 C15H17NO2
4-allyl-2-(5-propylisoxazol-3-yl)phenol
—— 5-methyl-2-(tetrahydro-2H-pyran-2-yl)phenol 117658-45-4 C12H16O2
5-methyl-2-(tetrahydro-2H-pyran-2-yl)phenol
—— 4-[1,3]Dithiolan-2-yl-3-methyl-phenol 80193-36-8 C10H12OS2
4-[1,3]Dithiolan-2-yl-3-methyl-phenol
—— 2,4-dihydroxy-6-methoxy-3-methyl-benzaldehyde 856077-16-2 C9H10O4
2,4-dihydroxy-6-methoxy-3-methyl-benzaldehyde
—— methyl [3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene](4-hydroxyphenyl)acetate 54805-73-1 C19H14O6
methyl [3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene](4-hydroxyphenyl)acetate
—— 3-methylphenyl-E-(3-hydroxy-5-methoxy)-styryl ether 960069-03-8 C16H16O3
3-methylphenyl-E-(3-hydroxy-5-methoxy)-styryl ether
—— 2-(4,5-dihydro-3-(4-methoxyphenyl)-5-isoxazolyl)-6-methoxyphenol 58721-44-1 C17H17NO4
2-(4,5-dihydro-3-(4-methoxyphenyl)-5-isoxazolyl)-6-methoxyphenol
—— ethyl (3-hydroxyphenyl)methylphosphinate 1219741-36-2 C9H13O3P
ethyl (3-hydroxyphenyl)methylphosphinate
—— 2-(4'-hydroxyphenyl)-3-(pyrrol-1"-yl)propionic acid 111751-81-6 C13H13NO3
2-(4'-hydroxyphenyl)-3-(pyrrol-1"-yl)propionic acid
—— (4-Hydroxy-2,3,6-trimethyl)-phenylessigsaeure-ethylester 128926-29-4 C13H18O3
(4-Hydroxy-2,3,6-trimethyl)-phenylessigsaeure-ethylester
—— Dobutamine tartrate 101626-66-8 C22H29NO9
Dobutamine tartrate
—— 5-Methyl-2-(tetrahydro-furan-2-yl)-phenol 120649-47-0 C11H14O2
5-Methyl-2-(tetrahydro-furan-2-yl)-phenol
—— (E)-diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-(2-pyrimidinyl)-amino]-vinylphosphonate 407583-31-7 C18H24N3O5P
(E)-diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-(2-pyrimidinyl)-amino]-vinylphosphonate
—— 3-[hydroxy(2-hydroxyphenyl)phosphinoyl]propylphosphonic acid 1391838-61-1 C9H14O6P2
3-[hydroxy(2-hydroxyphenyl)phosphinoyl]propylphosphonic acid