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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 (2'R,7S)-4-hydroxyspiro[bicyclo[4.2.0]octane-7,1'-cyclopropane]-1,3,5-triene-2'-carboxylate 1222090-79-0 C13H14O3
ethyl (2'R,7S)-4-hydroxyspiro[bicyclo[4.2.0]octane-7,1'-cyclopropane]-1,3,5-triene-2'-carboxylate
—— ethyl 4-hydroxyspiro[bicyclo[4.2.0]octane-7,1'-cyclopropane]-1,3,5-triene-2'-carboxylate —— C13H14O3
ethyl 4-hydroxyspiro[bicyclo[4.2.0]octane-7,1'-cyclopropane]-1,3,5-triene-2'-carboxylate
—— (S)-methyl 2-(5-hydroxy-1,2-dihydrocyclobutabenzen-1-yl)acetate 1187198-05-5 C11H12O3
(S)-methyl 2-(5-hydroxy-1,2-dihydrocyclobutabenzen-1-yl)acetate
—— (R)-methyl 2-(5-hydroxy-1,2-dihydrocyclobutabenzen-1-yl)acetate 1187198-04-4 C11H12O3
(R)-methyl 2-(5-hydroxy-1,2-dihydrocyclobutabenzen-1-yl)acetate
—— 4-(2-Hydroxybenzylideneamino)-3-methylphenol 84814-92-6 C14H13NO2
4-(2-Hydroxybenzylideneamino)-3-methylphenol
—— methyl[tris(4-hydroxyphenyl)]silane 183861-21-4 C19H18O3Si
methyl[tris(4-hydroxyphenyl)]silane
—— 4-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol 1026519-65-2 C12H16O3
4-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol
—— N,N,4-trimethylaniline;2,4,6-trinitrophenol 2739-03-9 C15H16N4O7
N,N,4-trimethylaniline;2,4,6-trinitrophenol
—— 3-allyl-4-nitrocatechol 189683-06-5 C9H9NO4
3-allyl-4-nitrocatechol
—— 2-Bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol 250284-68-5 C12H15BrO3
2-Bromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol
—— 4-(3,5-dimethylisoxazol-4-yl)-N'-hydroxy-5-(4-hydroxyphenyl)thiophene-3-carboximidamide 1360604-78-9 C16H15N3O3S
4-(3,5-dimethylisoxazol-4-yl)-N'-hydroxy-5-(4-hydroxyphenyl)thiophene-3-carboximidamide
—— 4-((pyridine-2-ylimino)methyl)benzene-1,3-diol 119004-79-4 C12H10N2O2
4-((pyridine-2-ylimino)methyl)benzene-1,3-diol
—— Tropane, picrate 6138-69-8 C14H18N4O7
Tropane, picrate
—— 5-[1,3]dioxan-2-yl-2-nitrophenol 200195-16-0 C10H11NO5
5-[1,3]dioxan-2-yl-2-nitrophenol
—— 2-Diethoxyphosphoryl-3-(4-hydroxyphenyl)propanenitrile 66324-65-0 C13H18NO4P
2-Diethoxyphosphoryl-3-(4-hydroxyphenyl)propanenitrile
—— 2-[(2,6-dimethylphenylimino)methyl]-4-nitrophenol 339991-46-7 C15H14N2O3
2-[(2,6-dimethylphenylimino)methyl]-4-nitrophenol
—— 3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenol 171368-15-3 C14H10N2O3
3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenol
—— ethyl 2-(3-(3-fluoro-4-hydroxyphenyl)oxetan-3-yl)acetate 1453862-19-5 C13H15FO4
ethyl 2-(3-(3-fluoro-4-hydroxyphenyl)oxetan-3-yl)acetate
—— 5-(1,2-dimethyl-2-propenyl)-4-hydroxy-2-methoxybenzaldehyde 1189552-11-1 C13H16O3
5-(1,2-dimethyl-2-propenyl)-4-hydroxy-2-methoxybenzaldehyde
—— 4-Hydroxy-chloromycetin 95173-06-1 C11H13Cl2NO4
4-Hydroxy-chloromycetin
—— 3,4-bis(benzyloxy)-2-fluorophenol 132178-20-2 C20H17FO3
3,4-bis(benzyloxy)-2-fluorophenol
—— 3,4,5-trihydroxyphenyl boronic acid 1285507-27-8 C6H7BO5
3,4,5-trihydroxyphenyl boronic acid
—— 2-(4-Hydroxyhydrocinnamoyl)-1,3-cyclopentanedione 37756-25-5 C14H14O4
2-(4-Hydroxyhydrocinnamoyl)-1,3-cyclopentanedione
—— 2-(4-Hydroxy-3-methoxyhydrocinnamoyl)-1,3-cyclopentanedione 37747-93-6 C15H16O5
2-(4-Hydroxy-3-methoxyhydrocinnamoyl)-1,3-cyclopentanedione
—— 2-(2-Hydroxyhydrocinnamoyl)-1,3-cyclopentanedione 37756-24-4 C14H14O4
2-(2-Hydroxyhydrocinnamoyl)-1,3-cyclopentanedione
—— 5,5'-((octane-1,8-diylbis(azanediyl))bis(methylene))bis(2-methoxyphenol) 1360453-47-9 C24H36N2O4
5,5'-((octane-1,8-diylbis(azanediyl))bis(methylene))bis(2-methoxyphenol)
—— 2-(3-Hydroxyhydrocinnamoyl)-1,3-cyclopentandion 37756-02-8 C14H14O4
2-(3-Hydroxyhydrocinnamoyl)-1,3-cyclopentandion
—— 2-OH-3-OMe-C6H3CHNC6H4CH3-3 94252-03-6 C15H15NO2
2-OH-3-OMe-C6H3CHNC6H4CH3-3
—— Ethyl 2-(3-formyl-4-hydroxy-5-methoxyphenyl)acetate 765302-60-1 C12H14O5
Ethyl 2-(3-formyl-4-hydroxy-5-methoxyphenyl)acetate
—— 1-{(4-methylphenylimino)-methyl}-2-hydroxy-3-methoxyphenol 20772-64-9 C15H15NO2
1-{(4-methylphenylimino)-methyl}-2-hydroxy-3-methoxyphenol
—— 2-[3-pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)sulfonyl]-4,5-dihydro-1H-pyrazol-5-yl]phenol 1035231-93-6 C23H18N4O3S2
2-[3-pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)sulfonyl]-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— 4-Methoxy-2-(3-methyl-but-2-enyloxy)-phenol 92720-64-4 C12H16O3
4-Methoxy-2-(3-methyl-but-2-enyloxy)-phenol
—— 2-(Ethylamino)ethanol-pentachlorophenol(1:1) 91818-14-3 C10H12Cl5NO2
2-(Ethylamino)ethanol-pentachlorophenol(1:1)
—— 4-(3-hydroxyphenyl)butyl alcohol 58081-14-4 C10H14O2
4-(3-hydroxyphenyl)butyl alcohol
—— 6-(3-hydroxy-4-methyl-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one 56872-35-6 C11H12N2O2
6-(3-hydroxy-4-methyl-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— 2-Propenyl-hydrochinon 1706-71-4 C9H10O2
2-Propenyl-hydrochinon
—— R-(-)-N-methyl-3-(2-methyl-4-hydroxyphenyloxy)-3-phenyl-1-aminopropane hydrochloride 457634-24-1 C17H21NO2*ClH
R-(-)-N-methyl-3-(2-methyl-4-hydroxyphenyloxy)-3-phenyl-1-aminopropane hydrochloride
—— (5-Chloro-2-Hydroxy-Phenyl)-Methanesulfonamide 519172-28-2 C7H8ClNO3S
(5-Chloro-2-Hydroxy-Phenyl)-Methanesulfonamide
—— (R)-2-[4-[3-(methylamino)-1-phenylpropoxy]phenyl]ethanol 1615654-47-1 C18H23NO2
(R)-2-[4-[3-(methylamino)-1-phenylpropoxy]phenyl]ethanol
—— (R)-2-[4-[3-(methylamino)-1-phenylpropoxy]phenyl]ethanol hydrochloride 1615654-08-4 C18H23NO2*ClH
(R)-2-[4-[3-(methylamino)-1-phenylpropoxy]phenyl]ethanol hydrochloride
—— 4-[3-(2-Chlorophenyl)-2-methyl-3,4-dihydropyrazol-5-yl]benzene-1,3-diol 1453488-28-2 C16H15ClN2O2
4-[3-(2-Chlorophenyl)-2-methyl-3,4-dihydropyrazol-5-yl]benzene-1,3-diol
—— 5,11,17,23-tetra-tert-butyl-26,27,28-tris((dimethyl(thiocarbamoyl)oxy))calix<4>arene-25-ol 173400-93-6 C53H71N3O4S3
5,11,17,23-tetra-tert-butyl-26,27,28-tris((dimethyl(thiocarbamoyl)oxy))calix<4>arene-25-ol
—— 4-{2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propylamino}-piperidine-1-carboxylic acid tert-butyl ester 890017-32-0 C22H36N2O5
4-{2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propylamino}-piperidine-1-carboxylic acid tert-butyl ester
—— (2'S,3'S)-N-{1,3-dihydroxy-4-[4-(2-methoxyethyl)phenoxy]-2-butyl}pivaloylamide 1032453-21-6 C18H29NO5
(2'S,3'S)-N-{1,3-dihydroxy-4-[4-(2-methoxyethyl)phenoxy]-2-butyl}pivaloylamide
—— (4S,5S)-4-(hydroxymethyl)-5-{[4-(2-methoxyethyl)phenoxy]methyl}oxazolidin-2-one 1032453-23-8 C14H19NO5
(4S,5S)-4-(hydroxymethyl)-5-{[4-(2-methoxyethyl)phenoxy]methyl}oxazolidin-2-one
—— 3-hydroxy-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide 1450923-59-7 C17H15N3O6S2
3-hydroxy-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide
—— 2-chloro-4-(α-hydroxyhexafluoroisopropyl)phenol 121058-41-1 C9H5ClF6O2
2-chloro-4-(α-hydroxyhexafluoroisopropyl)phenol
—— 2-[1,3,5]Trithian-2-yl-phenol 34119-68-1 C9H10OS3
2-[1,3,5]Trithian-2-yl-phenol
—— 3'-(4'''-bromophenyl)propanyl 3-(3''-hydroxy-4''-methoxyphenyl)propanoate 1146133-72-3 C19H21BrO4
3'-(4'''-bromophenyl)propanyl 3-(3''-hydroxy-4''-methoxyphenyl)propanoate
—— 2,6-Diaethyl-4-fluor-phenol 2928-20-3 C10H13FO
2,6-Diaethyl-4-fluor-phenol