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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
—— cyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate 1193988-39-4 C21H30N2O5
cyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate
—— 3-tert.-Butyl-2,6-dimethoxyphenol 49746-11-4 C12H18O3
3-tert.-Butyl-2,6-dimethoxyphenol
—— 2-(3-Ethyl-isoxazol-5-yl)-4-methyl-phenol 104516-58-7 C12H13NO2
2-(3-Ethyl-isoxazol-5-yl)-4-methyl-phenol
—— tert-butyl N-[2-(2-hydroxy-5-nitrophenyl)ethyl]carbamate 129295-71-2 C13H18N2O5
tert-butyl N-[2-(2-hydroxy-5-nitrophenyl)ethyl]carbamate
—— N-(5-ethoxycarbonyl)-2-nitro-3-hydroxy-4-methylbenzamide 121018-28-8 C16H22N2O6
N-(5-ethoxycarbonyl)-2-nitro-3-hydroxy-4-methylbenzamide
—— 4-(1-Cyclohexyl-pentyl)-phenol 19810-22-1 C17H26O
4-(1-Cyclohexyl-pentyl)-phenol
—— 2-Chloro-4-(2-methylthiophen-3-yl)phenol 1261982-92-6 C11H9ClOS
2-Chloro-4-(2-methylthiophen-3-yl)phenol
—— 2-((3,4-dimethylisoxazol-5-ylimino)methyl)-4-chlorophenol 1426400-31-8 C12H11ClN2O2
2-((3,4-dimethylisoxazol-5-ylimino)methyl)-4-chlorophenol
—— N-<2-Hydroxy-3,5-dinitro-benzyliden>-<2,5>-xylidin 5188-68-1 C15H13N3O5
N-<2-Hydroxy-3,5-dinitro-benzyliden>-<2,5>-xylidin
—— 2-(2-methoxycarbonylmethylthio)hydroquinone 136670-04-7 C9H10O4S
2-(2-methoxycarbonylmethylthio)hydroquinone
—— 3,5-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenol 1073480-25-7 C22H12F26O
3,5-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenol
—— 2-Chlor-1.1.1.3.3.3-hexafluor-2-(4-hydroxy-phenyl)-propan 722-91-8 C9H5ClF6O
2-Chlor-1.1.1.3.3.3-hexafluor-2-(4-hydroxy-phenyl)-propan
—— 4-[2-(6,7-dihydro-4<i>H</i>-furo[3,2-<i>c</i>]pyridin-5-yl)-1-hydroxy-ethyl]-phenol 53885-52-2 C15H17NO3
4-[2-(6,7-dihydro-4<i>H</i>-furo[3,2-<i>c</i>]pyridin-5-yl)-1-hydroxy-ethyl]-phenol
—— 9-(2-Hydroxy-phenyl)-bisdesundecyl-anhydrovilangin 1053-41-4 C19H10O8
9-(2-Hydroxy-phenyl)-bisdesundecyl-anhydrovilangin
—— 6-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole 916606-30-9 C15H12FNO3S
6-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole
—— Thailandamide lactone 1253291-39-2 C43H55NO8
Thailandamide lactone
—— 4-(o-hydroxybenzylideneamine)-5-<2-(2-pyridyl)ethenyl>-3-methylisoxazole 127501-66-0 C18H15N3O2
4-(o-hydroxybenzylideneamine)-5-<2-(2-pyridyl)ethenyl>-3-methylisoxazole
—— 4-[6-(Benzimidazol-1-yl)pyrazin-2-yl]-2-methoxyphenol 853887-75-9 C18H14N4O2
4-[6-(Benzimidazol-1-yl)pyrazin-2-yl]-2-methoxyphenol
—— 3-Methyl-4-<2-hydroxy-phenyl>-5-aethyl-isoxazol 14714-54-6 C12H13NO2
3-Methyl-4-<2-hydroxy-phenyl>-5-aethyl-isoxazol
—— 2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-4-methyl-phenol 651021-80-6 C16H12ClNO2
2-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-4-methyl-phenol
—— 6-Brom-2,5-dichlor-vanillin, 6-Brom-2,5-dichlor-4-hydroxy-3-methoxy-benzaldehyd 89892-19-3 C8H5BrCl2O3
6-Brom-2,5-dichlor-vanillin, 6-Brom-2,5-dichlor-4-hydroxy-3-methoxy-benzaldehyd
—— [2-Hydroxy-benzyliden]-4-rhodan-anilin 3378-58-3 C14H10N2OS
[2-Hydroxy-benzyliden]-4-rhodan-anilin
—— 6,6'-dichloro-4,4'-dinitro-3,3'-disulfanediyl-di-phenol 855839-22-4 C12H6Cl2N2O6S2
6,6'-dichloro-4,4'-dinitro-3,3'-disulfanediyl-di-phenol
—— 2,2-Bis-<3,5-dimethyl-4-hydroxy-phenyl>-glutarsaeure-anhydrid 94968-29-3 C21H22O5
2,2-Bis-<3,5-dimethyl-4-hydroxy-phenyl>-glutarsaeure-anhydrid
—— 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenol 179632-68-9 C9H9F3O2
4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenol
—— 5,11,17,23-tetrahexylcalix<4>arene 133732-47-5 C52H72O4
5,11,17,23-tetrahexylcalix<4>arene
—— 4-[2-(Diethylamino)ethyl]-2-(2-hydroxyphenyl)-1,3,4-oxadiazin-5-one;hydrochloride 53995-41-8 C15H22ClN3O3
4-[2-(Diethylamino)ethyl]-2-(2-hydroxyphenyl)-1,3,4-oxadiazin-5-one;hydrochloride
—— 2,4-Dibromo-6-[(E)-2-(3-methyl-4-nitro-isoxazol-5-yl)-vinyl]-phenol 80610-06-6 C12H8Br2N2O4
2,4-Dibromo-6-[(E)-2-(3-methyl-4-nitro-isoxazol-5-yl)-vinyl]-phenol
—— 1235459-56-9 C15H13NO3
—— pachydermin 878552-35-3 C13H8ClNO6
pachydermin
—— (S)-N-(2-hydroxy-4-nitrophenyl)-N'-(methyl benzyl)urea 201466-90-2 C15H15N3O4
(S)-N-(2-hydroxy-4-nitrophenyl)-N'-(methyl benzyl)urea
—— 5-allyl-6-(4-hydroxyphenyl)-8,9-dihydro-7H-benzocyclohepten-2-ol 1143509-79-8 C20H20O2
5-allyl-6-(4-hydroxyphenyl)-8,9-dihydro-7H-benzocyclohepten-2-ol
—— 4-(5-Undecyl-[1,3,4]thiadiazol-2-yl)-phenol 135605-51-5 C19H28N2OS
4-(5-Undecyl-[1,3,4]thiadiazol-2-yl)-phenol
—— 2-[[2-[bis(2-hydroxyethyl)amino]ethylamino]methyl]-4-nitrophenol 188289-03-4 C13H21N3O5
2-[[2-[bis(2-hydroxyethyl)amino]ethylamino]methyl]-4-nitrophenol
—— (3-hydroxy-2-methoxy-phenyl)boronic acid 2121512-62-5 C7H9BO4
(3-hydroxy-2-methoxy-phenyl)boronic acid
—— 2,5-Dihydroxy-benzaldehyd-octadecylthiosemicarbazon 96770-20-6 C26H45N3O2S
2,5-Dihydroxy-benzaldehyd-octadecylthiosemicarbazon
—— <4-Hydroxy-benzaldehyd>-2,6-dinitrophenylhydrazon 19266-12-7 C13H10N4O5
<4-Hydroxy-benzaldehyd>-2,6-dinitrophenylhydrazon
—— 4-<5-(dimethylamino)-6-nitro-3-cyclohexen-1-yl>-2-methoxyphenol 141944-27-6 C15H20N2O4
4-<5-(dimethylamino)-6-nitro-3-cyclohexen-1-yl>-2-methoxyphenol
—— 5-(2-thienyl)-4,5-dihydro-3-(2-hydroxyphenyl)pyrazole 55557-62-5 C13H12N2OS
5-(2-thienyl)-4,5-dihydro-3-(2-hydroxyphenyl)pyrazole
—— 2-(2-ethyl-hex-2-enylideneamino)-phenol 70299-36-4 C14H19NO
2-(2-ethyl-hex-2-enylideneamino)-phenol
—— 2,4-Dihydro-4-[[(4-hydroxy-3-methoxyphenyl)methylene]amino]-5-(1H-indol-3-ylmethyl)-3H-1,2,4-triazole-3-thione 957760-23-5 C19H17N5O2S
2,4-Dihydro-4-[[(4-hydroxy-3-methoxyphenyl)methylene]amino]-5-(1H-indol-3-ylmethyl)-3H-1,2,4-triazole-3-thione
—— 1062672-53-0 C21H26N4O2
—— 5-(1-cyclohexyl-1H-tetrazol-5-yl)-4-((4-hydroxyphenyl)ethyl)-5-methylthiomorpholin-3-one 1451408-78-8 C20H27N5O2S
5-(1-cyclohexyl-1H-tetrazol-5-yl)-4-((4-hydroxyphenyl)ethyl)-5-methylthiomorpholin-3-one
—— 5-<4-Methoxy-phenyl>-3-<2-hydroxy-5-acetamino-phenyl>-Δ<sup>2</sup>-cyclohexenon-(1)-carbonsaeure-(6)-ethylester 95623-32-8 C24H25NO6
5-<4-Methoxy-phenyl>-3-<2-hydroxy-5-acetamino-phenyl>-Δ<sup>2</sup>-cyclohexenon-(1)-carbonsaeure-(6)-ethylester
—— 2-phenol diazonium hexafluorophosphate 39151-46-7 C6H5N2O*F6P
2-phenol diazonium hexafluorophosphate
—— (R)-2-((1-hydroxy-3,3-dimethylbutan-2-ylimino)methyl)-4,6-diiodophenol 778625-56-2 C13H17I2NO2
(R)-2-((1-hydroxy-3,3-dimethylbutan-2-ylimino)methyl)-4,6-diiodophenol
—— 2-(3,3-dimethoxypropyl)phenol 1367759-93-0 C11H16O3
2-(3,3-dimethoxypropyl)phenol
—— 2-Cyano-5-hydroxyindane 149506-43-4 C10H9NO
2-Cyano-5-hydroxyindane
—— 4-(3,4-Dihydroxyphenyl)-2-(β-phenylethylamino)thiazole hydrochloride 79571-71-4 C17H16N2O2S*ClH
4-(3,4-Dihydroxyphenyl)-2-(β-phenylethylamino)thiazole hydrochloride
—— 4-(3,4-Dihydroxyphenyl)-2-(p-chlorophenylamino)thiazole hydrochloride 17927-78-5 C15H11ClN2O2S*ClH
4-(3,4-Dihydroxyphenyl)-2-(p-chlorophenylamino)thiazole hydrochloride