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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'-hydroxy-3'-fluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione 95333-49-6 C10H9FN2OS
1-(4'-hydroxy-3'-fluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione
—— Benzeneethanol, 4-((5-(3,3-dimethyloxiranyl)-3-methyl-2-pentenyl)oxy)-, (E)- 52662-57-4 C18H26O3
Benzeneethanol, 4-((5-(3,3-dimethyloxiranyl)-3-methyl-2-pentenyl)oxy)-, (E)-
—— S-Metoprolol sorbate 111337-50-9 C21H33NO5
S-Metoprolol sorbate
—— 3-((E)-Heptadec-1-enyl)benzene-1,2-diol 76607-94-8 C23H38O2
3-((E)-Heptadec-1-enyl)benzene-1,2-diol
—— (E)-4-(2-hydroxyphenyl)-2-methylbut-2-en-1-ol 58732-19-7 C11H14O2
(E)-4-(2-hydroxyphenyl)-2-methylbut-2-en-1-ol
—— 3-(Heptadecatrienyl)-1,2-benzenediol 76607-96-0 C23H34O2
3-(Heptadecatrienyl)-1,2-benzenediol
—— 4-methyl-2-(2-methyltetrahydrofuran-2-yl)phenol 117658-55-6 C12H16O2
4-methyl-2-(2-methyltetrahydrofuran-2-yl)phenol
—— 1-[3-(4-Hydroxyphenyl)propyl]-2-mercaptoimidazole 95333-65-6 C12H14N2OS
1-[3-(4-Hydroxyphenyl)propyl]-2-mercaptoimidazole
—— methyl (3-chloro-5-hydroxyphenyl)acetate 942268-67-9 C9H9ClO3
methyl (3-chloro-5-hydroxyphenyl)acetate
—— 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy acetic acid hydrazide 137841-66-8 C16H26N2O3
3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy acetic acid hydrazide
—— 3-hydroxy-5-chlorophenyl acetic acid 149029-88-9 C8H7ClO3
3-hydroxy-5-chlorophenyl acetic acid
—— 2-(3-Brom-4-hydroxy-5-methoxyphenyl)-2-propanol 55182-68-8 C10H13BrO3
2-(3-Brom-4-hydroxy-5-methoxyphenyl)-2-propanol
—— 2-(3'-hydroxy-4'-methoxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl 898562-22-6 C14H19N2O4
2-(3'-hydroxy-4'-methoxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl
—— 2-(3'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl 163461-40-3 C13H17N2O3
2-(3'-hydroxyphenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl
—— 2-fluoro-4-methoxyphenethyl methanesulfonate 1147392-07-1 C10H13FO4S
2-fluoro-4-methoxyphenethyl methanesulfonate
—— 2-(2-fluoro-4-methoxyphenyl)ethanol 1147392-04-8 C9H11FO2
2-(2-fluoro-4-methoxyphenyl)ethanol
—— 2,6-dimethyl-4-(2,4,6-trimethylamino)phenol 89231-62-9 C17H21NO
2,6-dimethyl-4-(2,4,6-trimethylamino)phenol
—— (E)-2-(but-1-enyl)-4-methoxyphenol 252234-13-2 C11H14O2
(E)-2-(but-1-enyl)-4-methoxyphenol
—— Methyl 3-amino-5-(2-hydroxyphenyl)-1,2-oxazole-4-carboxylate 1092534-31-0 C11H10N2O4
Methyl 3-amino-5-(2-hydroxyphenyl)-1,2-oxazole-4-carboxylate
—— 2-methoxy-4-[2-(3-methyl-5-isothiazolyl)ethenyl]phenol 113465-63-7 C13H13NO2S
2-methoxy-4-[2-(3-methyl-5-isothiazolyl)ethenyl]phenol
—— 4-{2-[(3,4-Dimethylphenyl)amino]-1,3-thiazol-4-yl}benzene-1,2-diol 733801-78-0 C17H16N2O2S
4-{2-[(3,4-Dimethylphenyl)amino]-1,3-thiazol-4-yl}benzene-1,2-diol
—— 2,6-Dihydroxyphenoxy-radikal 54560-53-1 C6H5O3
2,6-Dihydroxyphenoxy-radikal
—— 4-(5-amino-4-methylisothiazol-3-yl)phenol 1050392-36-3 C10H10N2OS
4-(5-amino-4-methylisothiazol-3-yl)phenol
—— 4-[bis(1,2,4-triazol-1-yl)methyl]phenol 502158-53-4 C11H10N6O
4-[bis(1,2,4-triazol-1-yl)methyl]phenol
—— 4-(Triallylsilyl)phenol 206276-09-7 C15H20OSi
4-(Triallylsilyl)phenol
—— 5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione 1452877-29-0 C15H16O7
5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
—— <i>N</i>-(4-hydroxy-benzyl)-stearamide 101940-29-8 C25H43NO2
<i>N</i>-(4-hydroxy-benzyl)-stearamide
—— 1-(4'-hydroxy-3',5'-difluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione 95333-60-1 C10H8F2N2OS
1-(4'-hydroxy-3',5'-difluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione
—— 20-Methyltetracyclo[15.4.0.03,8.010,15]henicosa-1(17),3,5,7,10,12,14,18,20-nonaene-5,6,12,13,19-pentol 164929-01-5 C22H20O5
20-Methyltetracyclo[15.4.0.03,8.010,15]henicosa-1(17),3,5,7,10,12,14,18,20-nonaene-5,6,12,13,19-pentol
—— 3-undecyl-benzene-1,2,4,5-tetraol 850878-20-5 C17H28O4
3-undecyl-benzene-1,2,4,5-tetraol
—— 2-(4-chlorophenoxy)-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]acetamide 106825-49-4 C18H17ClN2O5S
2-(4-chlorophenoxy)-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]acetamide
—— 2-<2-Hydroxy-benzyl>-furan 91344-47-7 C11H10O2
2-<2-Hydroxy-benzyl>-furan
—— 2-(4-Hydroxy-3-methoxyphenyl)-2-propanol 51941-34-5 C10H14O3
2-(4-Hydroxy-3-methoxyphenyl)-2-propanol
—— 2-(4-chlorophenoxy)-N-[2-(4-hydroxy-3-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]acetamide 1191380-43-4 C19H19ClN2O5S
2-(4-chlorophenoxy)-N-[2-(4-hydroxy-3-methoxyphenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]acetamide
—— 1-(2-Hydroxy-4-methoxy-phenyl)-4-phenoxy-but-2-yn-1-one 154810-59-0 C17H14O4
1-(2-Hydroxy-4-methoxy-phenyl)-4-phenoxy-but-2-yn-1-one
—— (2-hydroxy-5-methyl-phenyl)-methanesulfonic acid 107951-25-7 C8H10O4S
(2-hydroxy-5-methyl-phenyl)-methanesulfonic acid
—— 2,6-dipentylphenol 116374-97-1 C16H26O
2,6-dipentylphenol
—— 4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)phenol 3314-44-1 C15H14N2O
4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)phenol
—— Pyrocatechol, 4-(2-(N-allylphenethylamino)ethyl)-, fumarate (1:1) 70045-08-8 C23H27NO6
Pyrocatechol, 4-(2-(N-allylphenethylamino)ethyl)-, fumarate (1:1)
—— 3-hydroxy-2-nitro-benzenesulfonic acid amide 855426-17-4 C6H6N2O5S
3-hydroxy-2-nitro-benzenesulfonic acid amide
—— Pyrocatechol, 4-(2-(N-methylphenethylamino)ethyl)-, fumarate (2:1) 70044-85-8 C38H46N2O8
Pyrocatechol, 4-(2-(N-methylphenethylamino)ethyl)-, fumarate (2:1)
—— 1H-Imidazole-1-butanoic acid, 4,5-dihydro-4-((3-hydroxy-4-methoxyphenyl)methylene)-2-methyl-5-oxo- 73043-37-5 C16H18N2O5
1H-Imidazole-1-butanoic acid, 4,5-dihydro-4-((3-hydroxy-4-methoxyphenyl)methylene)-2-methyl-5-oxo-
—— (Z,Z)-3-(heptadeca-8',11'-dienyl)benzene-1,2-diol 54954-21-1 C23H36O2
(Z,Z)-3-(heptadeca-8',11'-dienyl)benzene-1,2-diol
—— 2-butyl-6-pentylphenol 116375-04-3 C15H24O
2-butyl-6-pentylphenol
—— 2-heptyl-6-pentylphenol 116375-05-4 C18H30O
2-heptyl-6-pentylphenol
—— 4H-Imidazol-4-one, 3,5-dihydro-5-((4-hydroxy-3-methoxyphenyl)methylene)-2-methyl-3-(5-propyl-1,3,4-thiadiazol-2-yl)- 76834-53-2 C17H18N4O3S
4H-Imidazol-4-one, 3,5-dihydro-5-((4-hydroxy-3-methoxyphenyl)methylene)-2-methyl-3-(5-propyl-1,3,4-thiadiazol-2-yl)-
—— 5-((3-Hydroxy-4-methoxyphenyl)methylene)selenazolidine-2,4-dione 82085-55-0 C11H9NO4Se
5-((3-Hydroxy-4-methoxyphenyl)methylene)selenazolidine-2,4-dione
—— 4-tert-butyldimethylsilyloxy-3-methoxyphenol 402469-27-6 C13H22O3Si
4-tert-butyldimethylsilyloxy-3-methoxyphenol
—— 5-((4-Hydroxy-3-methoxyphenyl)methylene)selenazolidine-2,4-dione 82085-56-1 C11H9NO4Se
5-((4-Hydroxy-3-methoxyphenyl)methylene)selenazolidine-2,4-dione
—— 5-((5-Bromo-2-hydroxyphenyl)methylene)selenazolidine-2,4-dione 82085-58-3 C10H6BrNO3Se
5-((5-Bromo-2-hydroxyphenyl)methylene)selenazolidine-2,4-dione