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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
—— 4-Allyl-benzene-1,2,3-triol 58169-21-4 C9H10O3
4-Allyl-benzene-1,2,3-triol
—— 2-Hydroxy-1-heptadecyl-benzol 96850-26-9 C23H40O
2-Hydroxy-1-heptadecyl-benzol
—— 25,27-{2,2'-[2,2'-((2,5,8-triaza)nonyl)diphenoxyl]diethyl}-p-tert-butylcalix[4]arene 189892-51-1 C66H85N3O6
25,27-{2,2'-[2,2'-((2,5,8-triaza)nonyl)diphenoxyl]diethyl}-p-tert-butylcalix[4]arene
—— 2-Nitro-4-sec-pentylphenol 91247-91-5 C11H15NO3
2-Nitro-4-sec-pentylphenol
—— (2S,3R)-3-tert-Butoxy-2-(2-hydroxy-4-methoxy-benzylamino)-butyric acid 166881-52-3 C16H25NO5
(2S,3R)-3-tert-Butoxy-2-(2-hydroxy-4-methoxy-benzylamino)-butyric acid
—— 2-[2-(2-hydroxyethyl)but-3-ynyl]phenol 1426384-70-4 C12H14O2
2-[2-(2-hydroxyethyl)but-3-ynyl]phenol
—— 3-hydroxy-2-nitrophenyl acetate 662138-32-1 C8H7NO5
3-hydroxy-2-nitrophenyl acetate
—— 1-(4-hydroxybenzylidene)-2-(pyridin-2-yl)hydrazine 10335-61-2 C12H11N3O
1-(4-hydroxybenzylidene)-2-(pyridin-2-yl)hydrazine
—— 4-Butoxy-2-[(dimethylamino)methyl]phenol 55955-89-0 C13H21NO2
4-Butoxy-2-[(dimethylamino)methyl]phenol
—— 4-hydroxysalicylaldehyde-2-pyridylhydrazone —— C12H11N3O2
4-hydroxysalicylaldehyde-2-pyridylhydrazone
—— 5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol 936368-39-7 C21H27NO2
5-[(3R,3aR,4R,6aS,8R,9bR)-3,6,8-trimethyl-2,3a,4,6a,7,8,9,9b-octahydro-3H-benzo[de]quinolin-4-yl]benzene-1,3-diol
—— 4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol hydrochloride 1237512-83-2 C11H17NO3*ClH
4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol hydrochloride
—— 4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol acetate 1237512-84-3 C2H4O2*C11H17NO3
4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol acetate
—— 4,5-bis[2-(ethyloxycarbonyl)ethyl]catechol 217975-35-4 C16H22O6
4,5-bis[2-(ethyloxycarbonyl)ethyl]catechol
—— 2-nitro-6-([1,2,4]triazol-4-ylimino-methyl)-phenol 35546-56-6 C9H7N5O3
2-nitro-6-([1,2,4]triazol-4-ylimino-methyl)-phenol
—— 1,2-Benzenediol, 4-[2-hydroxy-2-[(1-methylethyl)amino]ethyl]- 93128-02-0 C11H17NO3
1,2-Benzenediol, 4-[2-hydroxy-2-[(1-methylethyl)amino]ethyl]-
—— 4-[3-(Tert-butylamino)-2-hydroxypropoxy]-3-fluorobenzene-1,2-diol 132178-18-8 C13H20FNO4
4-[3-(Tert-butylamino)-2-hydroxypropoxy]-3-fluorobenzene-1,2-diol
—— 4-(3-tert-Butylamino-2-hydroxy-propoxy)-benzene-1,2-diol 64309-38-2 C13H21NO4
4-(3-tert-Butylamino-2-hydroxy-propoxy)-benzene-1,2-diol
—— 5-chloro-2,3-dihydroxybenzaldehyde 73275-96-4 C7H5ClO3
5-chloro-2,3-dihydroxybenzaldehyde
—— (R)-3-(4-Hydroxy-2,6-dimethyl-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one 955406-34-5 C20H25N3O2
(R)-3-(4-Hydroxy-2,6-dimethyl-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one
—— N'-[(5-hydroxy-2-nitrophenyl)-methylidene]pyridine-4-carbohydrazide 327987-95-1 C13H10N4O4
N'-[(5-hydroxy-2-nitrophenyl)-methylidene]pyridine-4-carbohydrazide
—— (R)-N-isopropyl-1-cyano-2-(3-hydroxyphenyl)cycloprop-2-enecarboxamide 1268853-78-6 C14H14N2O2
(R)-N-isopropyl-1-cyano-2-(3-hydroxyphenyl)cycloprop-2-enecarboxamide
—— ethyl (R)-1-cyano-2-(3-hydroxyphenyl)cycloprop-2-enecarboxylate 1268853-79-7 C13H11NO3
ethyl (R)-1-cyano-2-(3-hydroxyphenyl)cycloprop-2-enecarboxylate
—— 3-(3-methyl-3-phenylcyclobut-1-enyl)phenol 1235453-96-9 C17H16O
3-(3-methyl-3-phenylcyclobut-1-enyl)phenol
—— 2-ethylsulfonylmethylphenol 53380-27-1 C9H12O3S
2-ethylsulfonylmethylphenol
—— 1-benzyl-3,4-bis((3-hydroxyphenyl)ethynyl)-1H-pyrrole-2,5-dione 1380307-83-4 C27H17NO4
1-benzyl-3,4-bis((3-hydroxyphenyl)ethynyl)-1H-pyrrole-2,5-dione
—— o-Hydroxybutyrophenonoxim 21667-43-6 C10H13NO2
o-Hydroxybutyrophenonoxim
—— 5-{amino[1-(benzo[d][1,3]dioxol-5-yl)-1H-tetrazol-5-yl]methyl}-2-methoxyphenol 1268445-64-2 C16H15N5O4
5-{amino[1-(benzo[d][1,3]dioxol-5-yl)-1H-tetrazol-5-yl]methyl}-2-methoxyphenol
—— 4-(5,7-Dimethoxy-2,3-dihydro-benzo[1,4]oxathiin-2-yl)-benzene-1,2-diol 865541-38-4 C16H16O5S
4-(5,7-Dimethoxy-2,3-dihydro-benzo[1,4]oxathiin-2-yl)-benzene-1,2-diol
—— 2-Hydroxy-5-methyl-phenylnonylketoxim 71491-29-7 C17H27NO2
2-Hydroxy-5-methyl-phenylnonylketoxim
—— (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester 477980-80-6 C12H15ClO4
(S)-3-(3-Chloro-4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester
—— 2-Methyl-adrenalin 2887-78-7 C10H15NO3
2-Methyl-adrenalin
—— 2-Chlor-3,5-dihydroxybenzylalkohol 35354-28-0 C7H7ClO3
2-Chlor-3,5-dihydroxybenzylalkohol
—— 1,4-dihydro-2,6-dimethyl-4-(3',5'-dimethoxy-4'-hydroxyphenyl)-3,5-pyridinedicarboxylic acid, methyl ethyl ester 161187-64-0 C20H25NO7
1,4-dihydro-2,6-dimethyl-4-(3',5'-dimethoxy-4'-hydroxyphenyl)-3,5-pyridinedicarboxylic acid, methyl ethyl ester
—— 2-(N-hydroxy-C-methylcarbonimidoyl)-4-octylphenol 74604-09-4 C16H25NO2
2-(N-hydroxy-C-methylcarbonimidoyl)-4-octylphenol
—— 2-Allyl-5-ethoxy-4-methoxyphenol 522598-84-1 C12H16O3
2-Allyl-5-ethoxy-4-methoxyphenol
—— 3,5-dimethoxy-4-hydroxy-benzyl 2'-methoxy-4'-hydroxymethyl-phenyl ether 55525-43-4 C17H20O6
3,5-dimethoxy-4-hydroxy-benzyl 2'-methoxy-4'-hydroxymethyl-phenyl ether
—— 3-methoxy-2,5,6-trimethylphenol 34883-03-9 C10H14O2
3-methoxy-2,5,6-trimethylphenol
—— 3-(o-Hydroxyphenyl)-5-methylisoxazol 70423-62-0 C10H9NO2
3-(o-Hydroxyphenyl)-5-methylisoxazol
—— 2-(2-Hydroxy-5-methoxy-3-methylphenyl)-2-propanol 38102-59-9 C11H16O3
2-(2-Hydroxy-5-methoxy-3-methylphenyl)-2-propanol
—— 2-((tert-butyldimethylsilyl)methyl)phenol 1417315-92-4 C13H22OSi
2-((tert-butyldimethylsilyl)methyl)phenol
—— 3-Dodecyl-brenzcatechin 7573-08-2 C18H30O2
3-Dodecyl-brenzcatechin
—— 3-Cyclohexylidene-5-(4-hydroxy-phenyl)-3H-furan-2-one 959251-52-6 C16H16O3
3-Cyclohexylidene-5-(4-hydroxy-phenyl)-3H-furan-2-one
—— 2-(3',5'-Dihydroxyphenyl)-2-hydroxyethylamin 46049-55-2 C8H11NO3
2-(3',5'-Dihydroxyphenyl)-2-hydroxyethylamin
—— 3-Methyl-2-hydroxy-acetophenonimin 54758-47-3 C9H11NO
3-Methyl-2-hydroxy-acetophenonimin
—— 6-(2-Hydroxy-phenyl)-4,6-dimethyl-5-oxo-cyclohexa-1,3-dienecarboxylic acid methyl ester 40801-43-2 C16H16O4
6-(2-Hydroxy-phenyl)-4,6-dimethyl-5-oxo-cyclohexa-1,3-dienecarboxylic acid methyl ester
—— 4-(3-pyridylazo)resorcinol 16566-56-6 C11H9N3O2
4-(3-pyridylazo)resorcinol
—— salicylaldehydemethanesulfonylhydrazone 263009-12-7 C8H10N2O3S
salicylaldehydemethanesulfonylhydrazone
—— 2-(4-hydroxybenzylidene)-N-(2-hydroxyphenyl)hydrazine-1-carbothioamide 1097214-21-5 C14H13N3O2S
2-(4-hydroxybenzylidene)-N-(2-hydroxyphenyl)hydrazine-1-carbothioamide
—— piperidin-1-yl-[4-(hydroxy)phenyl]methanethione 58563-55-6 C12H15NOS
piperidin-1-yl-[4-(hydroxy)phenyl]methanethione