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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
—— 2-bromo-4,5-dihydroxyisophthalonitrile —— C8H3BrN2O2
2-bromo-4,5-dihydroxyisophthalonitrile
—— 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-2,8,14,20-tetrathiacalix[4]arene-monocrown-4 —— C46H58O6S4
5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-2,8,14,20-tetrathiacalix[4]arene-monocrown-4
—— p-tert-butylsulfinylcalix[4]arene —— C40H48O8S4
p-tert-butylsulfinylcalix[4]arene
—— p-tert-butylthiacalix[5]arene —— C50H60O5S5
p-tert-butylthiacalix[5]arene
—— 9H-2,6-dimethyl-9-(2-hydroxyphenyl)-bis[1,3,4]thiadiazolo[3,2-a:3',2'-d]-[1,3,5]triazin-8-ium chloride —— C13H12N5OS2*Cl
9H-2,6-dimethyl-9-(2-hydroxyphenyl)-bis[1,3,4]thiadiazolo[3,2-a:3',2'-d]-[1,3,5]triazin-8-ium chloride
—— 4-hydroxymethyl-5-catechol —— C8H10O3
4-hydroxymethyl-5-catechol
—— 3-decylcatechol —— C16H26O2
3-decylcatechol
—— dimethyl 4-hydroxy-2-methylphenyl phosphate —— C9H13O5P
dimethyl 4-hydroxy-2-methylphenyl phosphate
—— (4-chlorophenoxymethyl)-1,4-hydroquinone —— C13H11ClO3
(4-chlorophenoxymethyl)-1,4-hydroquinone
—— 2-(1-amino-2-cyclopropylethyl)-4-fluorophenol —— C11H14FNO
2-(1-amino-2-cyclopropylethyl)-4-fluorophenol
—— (E)-narain —— C3H10N3*C8H7O6S
(E)-narain
—— 2-chloro-4-(2-pyridon-1-yl)-methylphenol —— C12H10ClNO2
2-chloro-4-(2-pyridon-1-yl)-methylphenol
—— 3-benzylamino-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one —— C17H13F3N2O4
3-benzylamino-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one
—— 3-anilino-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one —— C16H11F3N2O4
3-anilino-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one
—— 4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one —— C12H11F3N2O5
4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one
—— 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-(2,5-dihydroxyphenyl)ethoxy)ethanesulfonic acid —— C10H6F8O6S
1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-(2,5-dihydroxyphenyl)ethoxy)ethanesulfonic acid
—— 3-(4-hydroxyphenyl)cyclopentanone —— C11H12O2
3-(4-hydroxyphenyl)cyclopentanone
—— N-(5-(2,3-dihydroxyphenyl)-1,3,4-thiadiazol-2-yl)-2-phenoxyacetamide —— C16H13N3O4S
N-(5-(2,3-dihydroxyphenyl)-1,3,4-thiadiazol-2-yl)-2-phenoxyacetamide
—— 2-(triethylsilylethynyl)phenol —— C14H20OSi
2-(triethylsilylethynyl)phenol
—— TX-1918 —— C14H12O3
TX-1918
—— 2-fluoro-6-(trimethylsilyl)phenol —— C9H13FOSi
2-fluoro-6-(trimethylsilyl)phenol
—— 4-(1-hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2-fluorophenol —— C10H8F4O4
4-(1-hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2-fluorophenol
—— 3-chloromethylcatechol —— C7H7ClO2
3-chloromethylcatechol
—— 3-(2-chloroethyl)catechol —— C8H9ClO2
3-(2-chloroethyl)catechol
—— 4-(3-fluoro-4-hydroxyphenyl)butan-2-one —— C10H11FO2
4-(3-fluoro-4-hydroxyphenyl)butan-2-one
—— 3-hydroxy-4-methoxyphenyl propyl carbonate —— C11H14O5
3-hydroxy-4-methoxyphenyl propyl carbonate
—— 2-tetrahydrogeranyl-5-methyl resorcinol —— C17H28O2
2-tetrahydrogeranyl-5-methyl resorcinol
—— 6-methylmercaptoorcinol —— C8H10O2S
6-methylmercaptoorcinol
—— 3-methyl-5-((triisopropylsilyl)oxy)phenol —— C16H28O2Si
3-methyl-5-((triisopropylsilyl)oxy)phenol
—— ethyl 5-(4-hydroxy-3-methylbenzylidene)-4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylate —— C21H19NO5
ethyl 5-(4-hydroxy-3-methylbenzylidene)-4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylate
—— 1,5-bis(5-bromosalicylidene)carbohydrazide 339242-77-2 C15H12Br2N4O3
1,5-bis(5-bromosalicylidene)carbohydrazide
—— 2-hydroxymethyl-3,4,6-trimethylphenol —— C10H14O2
2-hydroxymethyl-3,4,6-trimethylphenol
—— 2-(3-amino-3-methylbutyl)phenol —— C11H17NO
2-(3-amino-3-methylbutyl)phenol
—— 4-(m-hydroxyphenyl)-1,2-dithiole-3-thione —— C9H6OS3
4-(m-hydroxyphenyl)-1,2-dithiole-3-thione
—— (3-hydroxy-4,5-dimethoxy-phenyl)-acetic acid methyl ester —— C11H14O5
(3-hydroxy-4,5-dimethoxy-phenyl)-acetic acid methyl ester
—— 2-bromo-5-isopropyl-4-methoxy-phenol —— C10H13BrO2
2-bromo-5-isopropyl-4-methoxy-phenol
—— 2-((5-(2,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-yl)methyl)-5,6-diphenyl-1,2,4-triazin-3(2H)-one —— C24H17N5O4
2-((5-(2,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-yl)methyl)-5,6-diphenyl-1,2,4-triazin-3(2H)-one
—— 4-((4-aminocyclohexyl)methyl)phenol —— C13H19NO
4-((4-aminocyclohexyl)methyl)phenol
—— 1-nitro-2,4-dihydroxy-3,6-dimethylbenzene —— C8H9NO4
1-nitro-2,4-dihydroxy-3,6-dimethylbenzene
—— 2.6-dinitro-4-amino-3-oxy-toluene —— C7H7N3O5
2.6-dinitro-4-amino-3-oxy-toluene
—— 2-hydroxy-4-methyl-3,5-dinitro-benzoic acid —— C8H6N2O7
2-hydroxy-4-methyl-3,5-dinitro-benzoic acid
—— (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one —— C15H17NO3
(Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one
—— 3-(2-hydroxyphenyl)quinuclidin-2-ene —— C13H15NO
3-(2-hydroxyphenyl)quinuclidin-2-ene
—— 3,3'-(biphenyl-4,4'-diyl)bis(2-(2-hydroxyphenyl)thiazolidin-4-one) —— C30H24N2O4S2
3,3'-(biphenyl-4,4'-diyl)bis(2-(2-hydroxyphenyl)thiazolidin-4-one)
—— 5,6,7,8,9-penthathiabenzocycloheptane-1,2-diol —— C6H4O2S5
5,6,7,8,9-penthathiabenzocycloheptane-1,2-diol
—— 2-(1-methyl-decyl)-hydroquinone —— C17H28O2
2-(1-methyl-decyl)-hydroquinone
—— 3,4-dimercapto-benzene-1,2-diol —— C6H6O2S2
3,4-dimercapto-benzene-1,2-diol
—— 3-mercaptobenzene-1,2-diol —— C6H6O2S
3-mercaptobenzene-1,2-diol
—— N'-[(1E)-2-hydroxybenzylidene]-3-phenylpropanohydrazide —— C16H16N2O2
N'-[(1E)-2-hydroxybenzylidene]-3-phenylpropanohydrazide
—— 6-chloro-2-hydroxy-N,N-dimethyl-3-nitrobenzamide —— C9H9ClN2O4
6-chloro-2-hydroxy-N,N-dimethyl-3-nitrobenzamide