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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-[2-(3,3-dimethyl-3<i>H</i>-indol-2-yl)-vinyl]-4-nitro-phenol 68342-15-4 C18H16N2O3
2-[2-(3,3-dimethyl-3<i>H</i>-indol-2-yl)-vinyl]-4-nitro-phenol
—— 2-oxazolidin-2-yl-phenol 66670-97-1 C9H11NO2
2-oxazolidin-2-yl-phenol
—— 3-acetyl-2-(2-hydroxy-phenyl)-oxazolidine 4894-09-1 C11H13NO3
3-acetyl-2-(2-hydroxy-phenyl)-oxazolidine
—— (+/-)-(2-Hydroxyphenyl)methylphenylphosphine 160797-87-5 C13H13OP
(+/-)-(2-Hydroxyphenyl)methylphenylphosphine
—— 4-Bromo-2-(1-phenylethyliminomethyl)phenol 92425-37-1 C15H14BrNO
4-Bromo-2-(1-phenylethyliminomethyl)phenol
—— 2-(2,2-Difluoro-1-hydroxy-2-nitro-1-trifluoromethyl-ethyl)-5-methoxy-phenol 123716-14-3 C10H8F5NO5
2-(2,2-Difluoro-1-hydroxy-2-nitro-1-trifluoromethyl-ethyl)-5-methoxy-phenol
—— (S)-4-(4-hydroxybenzyl)-5,5-dimethyloxazolidinone 918164-76-8 C12H15NO3
(S)-4-(4-hydroxybenzyl)-5,5-dimethyloxazolidinone
—— (5R)-3-[(1S)-1-(4-hydroxyphenyl)ethyl]-5-[[[(1S)-1-(4-hydroxyphenyl)ethyl]amino]methyl]-1,3-oxazolidin-2-one 1351994-38-1 C20H24N2O4
(5R)-3-[(1S)-1-(4-hydroxyphenyl)ethyl]-5-[[[(1S)-1-(4-hydroxyphenyl)ethyl]amino]methyl]-1,3-oxazolidin-2-one
—— (3-Hydroxy-4-methoxyphenyl)(butyl)carbinol 6452-70-6 C12H18O3
(3-Hydroxy-4-methoxyphenyl)(butyl)carbinol
—— 4-[(1S)-1-[[2-hydroxy-3-[[(1S)-1-(4-hydroxyphenyl)ethyl]amino]propyl]amino]ethyl]phenol 1351994-20-1 C19H26N2O3
4-[(1S)-1-[[2-hydroxy-3-[[(1S)-1-(4-hydroxyphenyl)ethyl]amino]propyl]amino]ethyl]phenol
—— methyl-5-hydroxy-2-[4-[[5-(2-methoxycarbonylethyl)-2-methoxy]phenoxymethyl]-[5-(2-methoxycarbonylethyl)-2-methoxy]phenoxymethyl]-4-methoxyhydrocinnamate 147067-65-0 C35H42O12
methyl-5-hydroxy-2-[4-[[5-(2-methoxycarbonylethyl)-2-methoxy]phenoxymethyl]-[5-(2-methoxycarbonylethyl)-2-methoxy]phenoxymethyl]-4-methoxyhydrocinnamate
—— (+/-)-6-Fluoro-Epinephrine 115562-29-3 C9H12FNO3
(+/-)-6-Fluoro-Epinephrine
—— 4-chlorobenzylidene-2-amino-4-chlorophenol 64073-85-4 C13H9Cl2NO
4-chlorobenzylidene-2-amino-4-chlorophenol
—— (E)-4-chloro-2-((4-chlorobenzylidene)amino)phenol 1404220-82-1 C13H9Cl2NO
(E)-4-chloro-2-((4-chlorobenzylidene)amino)phenol
—— p-hydroxy-benzylidene-2-aminothiazole 114857-79-3 C10H8N2OS
p-hydroxy-benzylidene-2-aminothiazole
—— 4,5-Bis[(2-hydroxyphenyl)methylideneamino]pentane-1,2,3-triol 3673-13-0 C19H22N2O5
4,5-Bis[(2-hydroxyphenyl)methylideneamino]pentane-1,2,3-triol
—— 2-(3-ethoxyphenoxy)-N-(4-hydroxy-2-nitrophenyl)acetamide 1446338-26-6 C16H16N2O6
2-(3-ethoxyphenoxy)-N-(4-hydroxy-2-nitrophenyl)acetamide
—— 2-(5-methoxy-1H-indol-3-yl)ethanol;2,4,6-trinitrophenol 985-54-6 C17H16N4O9
2-(5-methoxy-1H-indol-3-yl)ethanol;2,4,6-trinitrophenol
—— ethyl (E)-8-(2-hydroxy-4-methoxyphenyl)oct-2-en-7-ynoate 1356471-35-6 C17H20O4
ethyl (E)-8-(2-hydroxy-4-methoxyphenyl)oct-2-en-7-ynoate
—— Guanidine-pentachlorophenol(1:1) 5944-83-2 C7H6Cl5N3O
Guanidine-pentachlorophenol(1:1)
—— 2-[[2-Hexyl-3-[(2-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol 6079-06-7 C26H38N2O4
2-[[2-Hexyl-3-[(2-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol
—— (E)-3-(dimethylamino)-1-(2-hydroxy-5-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)prop-2-en-1-one 1415914-34-9 C17H23NO5
(E)-3-(dimethylamino)-1-(2-hydroxy-5-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)prop-2-en-1-one
—— 4,5-Dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1196053-94-7 C14H21BO5
4,5-Dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— 1-[(2-Aminoethyl)amino]propan-2-ol-2,4,6-trinitrophenol(1:1) 25384-30-9 C11H17N5O8
1-[(2-Aminoethyl)amino]propan-2-ol-2,4,6-trinitrophenol(1:1)
—— mono(p-hydroxybenzilidene)-thiocarbohydrazone 63442-67-1 C8H10N4OS
mono(p-hydroxybenzilidene)-thiocarbohydrazone
—— ethyl 3-[3-chloro-4-hydroxy-5-5-(methyloxy)phenyl]propanoate 638214-98-9 C12H15ClO4
ethyl 3-[3-chloro-4-hydroxy-5-5-(methyloxy)phenyl]propanoate
—— 2-[Bis(2-chloroethyl)amino]ethanol;2,4,6-trinitrophenol 79395-70-3 C12H16Cl2N4O8
2-[Bis(2-chloroethyl)amino]ethanol;2,4,6-trinitrophenol
—— 4-Methyl-2-(3-methylsulfanyl-propyl)-phenol 17733-44-7 C11H16OS
4-Methyl-2-(3-methylsulfanyl-propyl)-phenol
—— 2-bis(3-tert-butylpyrazol-1-yl)methylphenol 1240795-93-0 C21H28N4O
2-bis(3-tert-butylpyrazol-1-yl)methylphenol
—— 2-[[3-[(2-Hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol 5767-44-2 C20H26N2O4
2-[[3-[(2-Hydroxy-3-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-6-methoxyphenol
—— 3-Oxy-1-methyl-2.4-diallyl-benzol 6630-76-8 C13H16O
3-Oxy-1-methyl-2.4-diallyl-benzol
—— N,N'-bis(5-nitrosalicylidene)-1,6-hexanediamine 212067-65-7 C20H22N4O6
N,N'-bis(5-nitrosalicylidene)-1,6-hexanediamine
—— 2-hydroxyphenyl heptyl selenide 217187-76-3 C13H20OSe
2-hydroxyphenyl heptyl selenide
—— 6-Chlor-5-brom-2-amino-vanillin 90221-44-6 C8H7BrClNO3
6-Chlor-5-brom-2-amino-vanillin
—— 4-(2-aminoethoxy)-3-methylphenol hydrochloride 1268609-78-4 C9H13NO2*ClH
4-(2-aminoethoxy)-3-methylphenol hydrochloride
—— 4-(1,3-dioxan-2-yl)-2-methoxyphenol 109816-39-9 C11H14O4
4-(1,3-dioxan-2-yl)-2-methoxyphenol
—— 2-((2-hydroxy-5-methoxybenzyloxy)methoxy)-5-methoxybenzaldehyde 1401070-98-1 C17H18O6
2-((2-hydroxy-5-methoxybenzyloxy)methoxy)-5-methoxybenzaldehyde
—— 5-Nitro-2-hydroxy-benzal-methylpentylhydrazin 1617-62-5 C13H19N3O3
5-Nitro-2-hydroxy-benzal-methylpentylhydrazin
—— [1,1-bis(hydroxymethyl)-3-(4-hydroxy-3-methylphenyl)propyl]carbamaic acid t-butyl ester 942400-16-0 C17H27NO5
[1,1-bis(hydroxymethyl)-3-(4-hydroxy-3-methylphenyl)propyl]carbamaic acid t-butyl ester
—— 2,4,6-Trinitrophenol-octahydro-1h-4,7-methanoinden-5-amine(1:1) 1052-60-4 C16H20N4O7
2,4,6-Trinitrophenol-octahydro-1h-4,7-methanoinden-5-amine(1:1)
—— 2-Methyl-4,6-di(thiomethoxymethyl)-phenol 15479-46-6 C11H16OS2
2-Methyl-4,6-di(thiomethoxymethyl)-phenol
—— 5-Hydroxy-oxprenolol 33712-14-0 C15H23NO4
5-Hydroxy-oxprenolol
—— 2-Methyl-4-thiomethoxymethyl-phenol 4526-48-1 C9H12OS
2-Methyl-4-thiomethoxymethyl-phenol
—— 2,5-Dibrom-6-chlor-vanillin, 2,5-Dibrom-6-chlor-4-hydroxy-3-methoxy-benzaldehyd 90001-46-0 C8H5Br2ClO3
2,5-Dibrom-6-chlor-vanillin, 2,5-Dibrom-6-chlor-4-hydroxy-3-methoxy-benzaldehyd
—— 5-tert-butyl-N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-(2-hydroxyphenyl)-1,3,4-thiadiazol-3(2H)-carboxamide 1190129-05-5 C19H25N5O2S2
5-tert-butyl-N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-(2-hydroxyphenyl)-1,3,4-thiadiazol-3(2H)-carboxamide
—— N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]dodecanamide 914491-26-2 C20H31Br2NO2
N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]dodecanamide
—— 1-Methylazepan-4-one;2,4,6-trinitrophenol 2006-44-2 C13H16N4O8
1-Methylazepan-4-one;2,4,6-trinitrophenol
—— 3-Pyridin-2-ylsulfanylbutan-2-one;2,4,6-trinitrophenol 5898-20-4 C15H14N4O8S
3-Pyridin-2-ylsulfanylbutan-2-one;2,4,6-trinitrophenol
—— (3-hydroxy-4-nitrophenyl)(pyrrolidin-1-yl)methanone 1390657-80-3 C11H12N2O4
(3-hydroxy-4-nitrophenyl)(pyrrolidin-1-yl)methanone
—— (3-hydroxy-4-nitrophenyl)(4-morpholinyl)methanone 129025-37-2 C11H12N2O5
(3-hydroxy-4-nitrophenyl)(4-morpholinyl)methanone