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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
—— 2,6-bis-[(3-hydroxy-propylimino)-methyl]-4-methyl-phenol 1356334-20-7 C15H22N2O3
2,6-bis-[(3-hydroxy-propylimino)-methyl]-4-methyl-phenol
—— 3-hydroxy-6,7-dimethylchromen-1-ylium 1609638-67-6 C11H11O2
3-hydroxy-6,7-dimethylchromen-1-ylium
—— methanesulfonic acid 3-[(1-carbamoylmethyl)but-3-enyl]-4-hydroxy-2-iodophenyl ester 1236071-36-5 C13H16INO5S
methanesulfonic acid 3-[(1-carbamoylmethyl)but-3-enyl]-4-hydroxy-2-iodophenyl ester
—— L-ornithinium dipicrate 6153-42-0 C5H12N2O2*2C6H3N3O7
L-ornithinium dipicrate
—— 5-(5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-methoxy phenol 1251485-66-1 C17H16N2O5
5-(5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-yl)-2-methoxy phenol
—— 2'-hydroxy-4',5'-dimethylacetophenone-4-methylthiosemicarbazone 147218-98-2 C12H17N3OS
2'-hydroxy-4',5'-dimethylacetophenone-4-methylthiosemicarbazone
—— 3,4,5-trihydroxy benzoic acid[1-(pyridyl)ethylidene]-hydrazone 551916-41-7 C14H13N3O4
3,4,5-trihydroxy benzoic acid[1-(pyridyl)ethylidene]-hydrazone
—— 2-[2-bromoethyliminomethyl]phenol 80622-20-4 C9H10BrNO
2-[2-bromoethyliminomethyl]phenol
—— H2(4-OMe-sal-3-NO2-ophen) 194794-34-8 C22H19N3O6
H2(4-OMe-sal-3-NO2-ophen)
—— 1-(2-hydroxy-4,6-dinitro-phenyl)-3-methyl-5-(1-methyl-1<i>H</i>-benzoimidazol-2-yl)-formazan 33883-61-3 C16H14N8O5
1-(2-hydroxy-4,6-dinitro-phenyl)-3-methyl-5-(1-methyl-1<i>H</i>-benzoimidazol-2-yl)-formazan
—— 4-nitro-3-([1,2,4]triazol-4-ylimino-methyl)-phenol 35605-11-9 C9H7N5O3
4-nitro-3-([1,2,4]triazol-4-ylimino-methyl)-phenol
—— β-Orcilaldehyde-4-(o-tolyl)thiosemicarbazone 19861-15-5 C17H19N3O2S
β-Orcilaldehyde-4-(o-tolyl)thiosemicarbazone
—— (2-[1-(3-methylamino-propylimino)-ethyl]-phenol) 1258211-23-2 C12H18N2O
(2-[1-(3-methylamino-propylimino)-ethyl]-phenol)
—— 4-methyl-2-(propylthio)phenol 1569262-77-6 C10H14OS
4-methyl-2-(propylthio)phenol
—— 6-[(1E,5E)-6-(5-bromo-2-hydroxy-3-nitrophenyl)-2,5-diazahexa-1,5-dienyl]-4-bro mo-2-nitrophenol 329070-67-9 C16H12Br2N4O6
6-[(1E,5E)-6-(5-bromo-2-hydroxy-3-nitrophenyl)-2,5-diazahexa-1,5-dienyl]-4-bro mo-2-nitrophenol
—— 5-(4-hydroxyphenyl)pyrazine-2,3-dicarbonitrile 67823-04-5 C12H6N4O
5-(4-hydroxyphenyl)pyrazine-2,3-dicarbonitrile
—— 2,3-dicyano-5,6-bis(4-hydroxyphenyl)pyrazine 935249-88-0 C18H10N4O2
2,3-dicyano-5,6-bis(4-hydroxyphenyl)pyrazine
—— 5-[2-(2-ethyl-[1,3]dithiolan-2-yl)-ethyl]-benzene-1,3-diol 34589-91-8 C13H18O2S2
5-[2-(2-ethyl-[1,3]dithiolan-2-yl)-ethyl]-benzene-1,3-diol
—— 4-bromo-5-chloro-2-fluorophenol 1805518-69-7 C6H3BrClFO
4-bromo-5-chloro-2-fluorophenol
—— 3-bromo-2-chloro-6-fluorophenol 943830-15-7 C6H3BrClFO
3-bromo-2-chloro-6-fluorophenol
—— 4-[4-butoxy-6-(4-chloro-phenyl)-[1,3,5]triazin-2-yl]-benzene-1,3-diol 4686-79-7 C19H18ClN3O3
4-[4-butoxy-6-(4-chloro-phenyl)-[1,3,5]triazin-2-yl]-benzene-1,3-diol
—— SR-ractopamine hydrochloride 235425-01-1 C18H23NO3*ClH
SR-ractopamine hydrochloride
—— 1,3-bis(2-hydroxy-5-bromosalicylideneamino)propan-2-ol 327065-06-5 C17H16Br2N2O3
1,3-bis(2-hydroxy-5-bromosalicylideneamino)propan-2-ol
—— diisopropyl (2-(4-hydroxy-3-methoxyphenyl)-3,6-dimethylhexahydropyrrolo[1,2-b]isoxazol-6-yl)phosphonate 1201808-97-0 C21H34NO6P
diisopropyl (2-(4-hydroxy-3-methoxyphenyl)-3,6-dimethylhexahydropyrrolo[1,2-b]isoxazol-6-yl)phosphonate
—— 2[(phenylthio)methyl]-4,5-dimethylphenol 54373-34-1 C15H16OS
2[(phenylthio)methyl]-4,5-dimethylphenol
—— 123903-00-4 3CNS*C82H114N6O12*3Na
—— 2,2'-(1,2-ethanediylbisnitrilomethylidine)bis-(4-hydroxyphenolato)nickel(II) 98052-47-2 C16H14N2NiO4
2,2'-(1,2-ethanediylbisnitrilomethylidine)bis-(4-hydroxyphenolato)nickel(II)
—— bis(2,4-dihydroxyacetophenone)ethylenediimine 75979-16-7 C18H20N2O4
bis(2,4-dihydroxyacetophenone)ethylenediimine
—— 4-(2-hexyldecyl)phenol 1228301-94-7 C22H38O
4-(2-hexyldecyl)phenol
—— 1361117-91-0 C13H18O4S
—— 4-Hydroxy-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-2,5-dihydro-thiophene-3-carboxylic acid ethyl ester 10281-87-5 C15H14O6S
4-Hydroxy-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-2,5-dihydro-thiophene-3-carboxylic acid ethyl ester
—— 4-(5-bromo-5-nitro-[1,3]dioxan-2-yl)-phenol 60766-61-2 C10H10BrNO5
4-(5-bromo-5-nitro-[1,3]dioxan-2-yl)-phenol
—— 2,4-dibromo-6-[(2-ethylaminoethylimino)methyl]phenol 1051457-01-2 C11H14Br2N2O
2,4-dibromo-6-[(2-ethylaminoethylimino)methyl]phenol
—— Methanesulfonic acid 3-(2-hydroxy-3,4,6-trimethyl-phenyl)-propyl ester 40614-14-0 C13H20O4S
Methanesulfonic acid 3-(2-hydroxy-3,4,6-trimethyl-phenyl)-propyl ester
—— Orcilaldehyde 4-(p-ethoxyphenyl)-thiosemicarbazone 21236-12-4 C17H19N3O3S
Orcilaldehyde 4-(p-ethoxyphenyl)-thiosemicarbazone
—— methyl 2-[(1R,3aS,4S,7aS)-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-5-oxo-2,3,3a,4,6,7-hexahydro-1H-inden-1-yl]propanoate 103596-05-0 C23H32O4
methyl 2-[(1R,3aS,4S,7aS)-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-5-oxo-2,3,3a,4,6,7-hexahydro-1H-inden-1-yl]propanoate
—— isovanillyl 7-methyloctanoate 1000377-98-9 C17H26O4
isovanillyl 7-methyloctanoate
—— 2-(p-hydroxyphenyl) α-diazoethyl ketone 66628-98-6 C11H12N2O2
2-(p-hydroxyphenyl) α-diazoethyl ketone
—— (R,S)-salen 257636-49-0 C20H22N2O2
(R,S)-salen
—— m-Hydroxy-benzaldehyd-dibenzylmercaptal 32188-40-2 C21H20OS2
m-Hydroxy-benzaldehyd-dibenzylmercaptal
—— amantadine-o-vanillin 57277-82-4 C18H23NO2
amantadine-o-vanillin
—— (Z)-2-amino-3-[1-(2-hydroxyphenyl)ethylideneamino]but-2-enedinitrile 55752-08-4 C12H10N4O
(Z)-2-amino-3-[1-(2-hydroxyphenyl)ethylideneamino]but-2-enedinitrile
—— amantadine-5-chloro-salicylaldehyde 532420-46-5 C17H20ClNO
amantadine-5-chloro-salicylaldehyde
—— N-salicylidene-2,3-diamino-cis-2-butenedinitrile 56029-20-0 C11H8N4O
N-salicylidene-2,3-diamino-cis-2-butenedinitrile
—— 2-hydroxyacetophenone N-methylthiosemicarbazone 166036-42-6 C10H13N3OS
2-hydroxyacetophenone N-methylthiosemicarbazone
—— N,N'-disalicylidene-1,3-diamino-4-nitrobenzene 1169932-65-3 C20H15N3O4
N,N'-disalicylidene-1,3-diamino-4-nitrobenzene
—— 25,26,27-tris<(trimethylsilyl)oxy>-28-hydroxycalix<4>arene 99033-42-8 C37H48O4Si3
25,26,27-tris<(trimethylsilyl)oxy>-28-hydroxycalix<4>arene
—— 4-bromo-2-[(2-hydroxyethyl)-iminomethyl]phenol 21974-51-6 C9H10BrNO2
4-bromo-2-[(2-hydroxyethyl)-iminomethyl]phenol
—— 2-(1-[1,2,4]triazol-4-ylimino-ethyl)-benzene-1,4-diol 35554-87-1 C10H10N4O2
2-(1-[1,2,4]triazol-4-ylimino-ethyl)-benzene-1,4-diol
—— 2,4-Di-(5-N-piperidyl-1,3-pentadiynyl)phenol 30462-86-3 C26H28N2O
2,4-Di-(5-N-piperidyl-1,3-pentadiynyl)phenol