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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
—— ethyl 3-(2-hydroxy-5-nitrophenyl)propanoate 20921-11-3 C11H13NO5
ethyl 3-(2-hydroxy-5-nitrophenyl)propanoate
—— (1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol 84799-27-9 C10H14O5
(1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol
—— erythro 1-(4-hydroxy-3-methoxy)-phenyl-1,Z,3-propanetriol —— C10H14O5
erythro 1-(4-hydroxy-3-methoxy)-phenyl-1,Z,3-propanetriol
—— ethyl 2-hydroxy-3-nitrobenzenepropanoate 54892-94-3 C11H13NO5
ethyl 2-hydroxy-3-nitrobenzenepropanoate
—— 1,2,3,4-tetramethoxy-5-methyl-6-(2-methoxyethyl)benzene 84055-99-2 C14H22O5
1,2,3,4-tetramethoxy-5-methyl-6-(2-methoxyethyl)benzene
—— 4-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide 1350618-58-4 C15H21NO4
4-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
—— 2-(4-nitro-3-phenyl-4,5-dihydro-isoxazol-5-yl)-phenol 62260-75-7 C15H12N2O4
2-(4-nitro-3-phenyl-4,5-dihydro-isoxazol-5-yl)-phenol
—— 3-Hexadecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)- 104264-55-3 C23H38O4
3-Hexadecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-
—— 1-[1-(2-hydroxyphenyl)ethyl]piperidine 461389-79-7 C13H19NO
1-[1-(2-hydroxyphenyl)ethyl]piperidine
—— 1-[1-(3-hydroxyphenyl)ethyl]piperidine 124476-34-2 C13H19NO
1-[1-(3-hydroxyphenyl)ethyl]piperidine
—— 25,27-bis(diethylcarbamoyloxy)-26,28-dihydroxycalix[4]arene 261639-36-5 C38H42N2O6
25,27-bis(diethylcarbamoyloxy)-26,28-dihydroxycalix[4]arene
—— 4-(2-hydroxy-3,5-dinitrophenyl)-1,2,5-thiadiazole-3-carboxylic acid 119458-72-9 C9H4N4O7S
4-(2-hydroxy-3,5-dinitrophenyl)-1,2,5-thiadiazole-3-carboxylic acid
—— (5Z)-5-(4-fluoro-2-hydroxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one 1181083-06-6 C16H18FN3O3S
(5Z)-5-(4-fluoro-2-hydroxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one
—— Sawaranospirolide B 128508-29-2 C14H16O7
Sawaranospirolide B
—— (5Z)-2-(1,2-diazinan-1-yl)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one 1181082-85-8 C14H14FN3O2S
(5Z)-2-(1,2-diazinan-1-yl)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one
—— Sawaranospirolide D 128508-31-6 C14H16O7
Sawaranospirolide D
—— 5-Nitro-2-hydroxy-benzal-methylphenylhydrazin 2027-52-3 C14H13N3O3
5-Nitro-2-hydroxy-benzal-methylphenylhydrazin
—— 5-bromo-4-fluoro-2-methoxyphenol 1364606-67-6 C7H6BrFO2
5-bromo-4-fluoro-2-methoxyphenol
—— 4-(benzyloxy)-2-fluorophenol 84352-10-3 C13H11FO2
4-(benzyloxy)-2-fluorophenol
—— Phenol, 2(or 4)-sec-eicosyl- 233587-34-3 C26H46O
Phenol, 2(or 4)-sec-eicosyl-
—— o-Hydroxy-phenyl-propiolsaeure-N-methyl-amid 21315-51-5 C10H9NO2
o-Hydroxy-phenyl-propiolsaeure-N-methyl-amid
—— (R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic amide 251565-92-1 C28H33NO7S
(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic amide
—— 2-methoxy-4-(5-((2-methylbenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol 1391739-57-3 C17H16N2O3S
2-methoxy-4-(5-((2-methylbenzyl)thio)-1,3,4-oxadiazol-2-yl)phenol
—— 3-(2,3-difluoro-4-hydroxyphenyl)-4,4-dimethyl-1H-pyrazol-5(4H)-one 1010801-04-3 C11H10F2N2O2
3-(2,3-difluoro-4-hydroxyphenyl)-4,4-dimethyl-1H-pyrazol-5(4H)-one
—— 4-octyl-2,3-difluorophenol 124728-39-8 C14H20F2O
4-octyl-2,3-difluorophenol
—— 4-(tert-butoxy)-2,6-dimethylphenol 2460-81-3 C12H18O2
4-(tert-butoxy)-2,6-dimethylphenol
—— 2,6-dimethyl-3-morpholinomethyl-hydro-p-benzoquinone 910228-93-2 C13H19NO3
2,6-dimethyl-3-morpholinomethyl-hydro-p-benzoquinone
—— 2-bromo-3,5-dimethyl-hydroquinone 409316-82-1 C8H9BrO2
2-bromo-3,5-dimethyl-hydroquinone
—— 4-(3-hydroxypropyl)-2,6-dimethylphenol 122004-95-9 C11H16O2
4-(3-hydroxypropyl)-2,6-dimethylphenol
—— 2-(4-hydroxy-3,5-dimethyl-phenyl)-ethene-1,1,2-tricarbonitrile 25751-81-9 C13H9N3O
2-(4-hydroxy-3,5-dimethyl-phenyl)-ethene-1,1,2-tricarbonitrile
—— 2-allyl-3,5-dimethylhydroquinone 67883-66-3 C11H14O2
2-allyl-3,5-dimethylhydroquinone
—— 3,5-dimethyl-2-nitrophenol 5345-09-5 C8H9NO3
3,5-dimethyl-2-nitrophenol
—— 2-methoxy-6-sulfanylphenol 470454-10-5 C7H8O2S
2-methoxy-6-sulfanylphenol
—— 2-(S)-methyl-3-(2-hydroxy-3-methoxy-phenylthio)propan-1-ol 470454-12-7 C11H16O3S
2-(S)-methyl-3-(2-hydroxy-3-methoxy-phenylthio)propan-1-ol
—— 2-(1-Methylcyclohexylcarbonyloxy)-4,6-dinitrophenol 116314-94-4 C14H16N2O7
2-(1-Methylcyclohexylcarbonyloxy)-4,6-dinitrophenol
—— 2-(4-chlorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-4-thiazolidinone 358340-84-8 C17H13ClN2O3S
2-(4-chlorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-4-thiazolidinone
—— 5-(2-hydroxyphenyl)-3,3-spirocyclobutylbutyrolactone 1354358-77-2 C13H14O3
5-(2-hydroxyphenyl)-3,3-spirocyclobutylbutyrolactone
—— 4-Hydroxy-2,6-dimethoxy-benzenesulfonic acid 140650-67-5 C8H10O6S
4-Hydroxy-2,6-dimethoxy-benzenesulfonic acid
—— 5-(4-hydroxyphenyl)-3,3-spirocyclobutylbutyrolactone 1354358-76-1 C13H14O3
5-(4-hydroxyphenyl)-3,3-spirocyclobutylbutyrolactone
—— 4-(2-((4-bromophenyl)amino)ethoxy)phenol 1452855-66-1 C14H14BrNO2
4-(2-((4-bromophenyl)amino)ethoxy)phenol
—— 4-(pent-4-en-1-yl)phenol 52130-14-0 C11H14O
4-(pent-4-en-1-yl)phenol
—— 4-(1-Methylcyclopropyl)-2-nitrophenol 74387-09-0 C10H11NO3
4-(1-Methylcyclopropyl)-2-nitrophenol
—— 7,15,23-Trimethyl-3,11,19-tris(prop-2-enyl)-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13(26),14,16,21(25),22-nonaene-25,26,27-triol 301152-65-8 C36H45N3O3
7,15,23-Trimethyl-3,11,19-tris(prop-2-enyl)-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13(26),14,16,21(25),22-nonaene-25,26,27-triol
—— 2-(3-hydroxypropyl)-5-methylphenol 90926-15-1 C10H14O2
2-(3-hydroxypropyl)-5-methylphenol
—— 2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-5-methylphenol 300767-46-8 C16H26O2Si
2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-5-methylphenol
—— 6-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-2,3-dimethylphenol 300767-07-1 C17H28O2Si
6-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-2,3-dimethylphenol
—— 2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-6-methylphenol 300767-61-7 C16H26O2Si
2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-6-methylphenol
—— 2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-3,4,5-trimethylphenol 300767-31-1 C18H30O2Si
2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-3,4,5-trimethylphenol
—— 3-[β-(4'-Hydroxy-3'-methoxyphenyl)ethyl]-5-methylpyrazole 113464-95-2 C13H16N2O2
3-[β-(4'-Hydroxy-3'-methoxyphenyl)ethyl]-5-methylpyrazole
—— 2-[(Z)-3-hydroxy-1-propenyl]-5-methoxyphenol 300767-53-7 C10H12O3
2-[(Z)-3-hydroxy-1-propenyl]-5-methoxyphenol