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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
—— (<i>S</i>)-2-(4-hydroxy-phenyl)-propionic acid methyl ester 124508-78-7 C10H12O3
(<i>S</i>)-2-(4-hydroxy-phenyl)-propionic acid methyl ester
—— spoxazomicin C 1337978-34-3 C10H11NO3
spoxazomicin C
—— 2-allyl-4-[(tert-butyl(dimethyl)silyloxy)methyl]phenol 137314-07-9 C16H26O2Si
2-allyl-4-[(tert-butyl(dimethyl)silyloxy)methyl]phenol
—— 4-Hexyl-2-(N-(o-hydroxyphenyl)formimidoyl)phenol 16704-09-9 C19H23NO2
4-Hexyl-2-(N-(o-hydroxyphenyl)formimidoyl)phenol
—— 5-chloro-2-hydroxyphenyl isocyanate 122020-63-7 C7H4ClNO2
5-chloro-2-hydroxyphenyl isocyanate
—— 2-(4,5-dihydrooxazol-2-yl)-5-methylphenol 24201-15-8 C10H11NO2
2-(4,5-dihydrooxazol-2-yl)-5-methylphenol
—— 3-(4-hydroxy-2-methoxyphenyl)propanol 106800-27-5 C10H14O3
3-(4-hydroxy-2-methoxyphenyl)propanol
—— 2-(4-hydroxy-2-methylphenyl)-2-methyl-1,3-dioxolane 1171247-69-0 C11H14O3
2-(4-hydroxy-2-methylphenyl)-2-methyl-1,3-dioxolane
—— 4-methoxy-2-(methoxymethoxy)phenol 123913-92-8 C9H12O4
4-methoxy-2-(methoxymethoxy)phenol
—— 3-(2-hydroxy-4-methoxyphenyl)propanol 106800-26-4 C10H14O3
3-(2-hydroxy-4-methoxyphenyl)propanol
—— (2-Fluoro-4-hydroxy-benzyl)-carbamic acid tert-butyl ester 392636-92-9 C12H16FNO3
(2-Fluoro-4-hydroxy-benzyl)-carbamic acid tert-butyl ester
—— 5-(adamantan-1-ylaminomethyl)-2-methoxyphenol 1019579-53-3 C18H25NO2
5-(adamantan-1-ylaminomethyl)-2-methoxyphenol
—— 3-methyl-4-methoxy-1,2-dihydroxybenzene 77357-51-8 C8H10O3
3-methyl-4-methoxy-1,2-dihydroxybenzene
—— 5-isopropoxy-2,4-dimethoxy-3-methylphenol 105104-02-7 C12H18O4
5-isopropoxy-2,4-dimethoxy-3-methylphenol
—— 4-(4-hydroxy-3-methoxyphenyl)-2-methylenebutyrolactone 1447662-19-2 C12H12O4
4-(4-hydroxy-3-methoxyphenyl)-2-methylenebutyrolactone
—— 2,4,5-trimethoxy-3-methylphenol 105104-01-6 C10H14O4
2,4,5-trimethoxy-3-methylphenol
—— p-tert-butylcalix[5]PNMe2(OH)3 202530-58-3 C57H74NO5P
p-tert-butylcalix[5]PNMe2(OH)3
—— (1S,4S,5R,6R)-4-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-2-oxo-6-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester 641627-93-2 C34H50N2O7Si
(1S,4S,5R,6R)-4-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-2-oxo-6-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester
—— 5-(2-acetoxyethyl)-2-(benzyloxy)benzoic acid 1237517-67-7 C18H18O5
5-(2-acetoxyethyl)-2-(benzyloxy)benzoic acid
—— 6-(4-hydroxyphenyl)hexan-2-one 169334-30-9 C12H16O2
6-(4-hydroxyphenyl)hexan-2-one
—— 2,5-diphosphinohydroquinone 1220997-34-1 C6H8O2P2
2,5-diphosphinohydroquinone
—— (5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 1181081-68-4 C10H6FNO2S2
(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (Z)-5-(3-hydroxybenzylidene)-2-thioxo-thiazolidine-4-one 37530-35-1 C10H7NO2S2
(Z)-5-(3-hydroxybenzylidene)-2-thioxo-thiazolidine-4-one
—— 3-Hydroxy-4-methoxybenzyliden-rhodanin 69505-47-1 C11H9NO3S2
3-Hydroxy-4-methoxybenzyliden-rhodanin
—— (5Z)-5-(2-hydroxybenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 1181081-33-3 C15H17N3O2S
(5Z)-5-(2-hydroxybenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
—— (5Z)-5-[(3-hydroxyphenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181082-26-7 C15H16N2O2S
(5Z)-5-[(3-hydroxyphenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(pyrrolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-32-2 C14H14N2O2S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(pyrrolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 2-<2-hydroxy-3-(phenylthio)propyl>-4-methylphenol 126734-04-1 C16H18O2S
2-<2-hydroxy-3-(phenylthio)propyl>-4-methylphenol
—— (3R)-1-[(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]-N,N-dimethylpyrrolidin-3-aminium chloride 1181081-45-7 C16H18FN3O2S*ClH
(3R)-1-[(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]-N,N-dimethylpyrrolidin-3-aminium chloride
—— 2-<3-hydroxy-2-(phenylthio)propyl>-6-methylphenol 126708-13-2 C16H18O2S
2-<3-hydroxy-2-(phenylthio)propyl>-6-methylphenol
—— 2-Cyclopropylmethyl-6-methyl-phenol 36161-15-6 C11H14O
2-Cyclopropylmethyl-6-methyl-phenol
—— 1-(3,5-dibromo-4-hydroxyphenyl)-6-methyluracil 83809-83-0 C11H8Br2N2O3
1-(3,5-dibromo-4-hydroxyphenyl)-6-methyluracil
—— 1-(3,5-dibromo-4-hydroxyphenyl)-5-bromo-6-methyldihydrouracil 83809-79-4 C11H9Br3N2O3
1-(3,5-dibromo-4-hydroxyphenyl)-5-bromo-6-methyldihydrouracil
—— 2-allylphenol dibromide 84767-98-6 C9H10Br2O
2-allylphenol dibromide
—— 4-[3-methyl-4-(4-methoxyphenyl)isoxazol-5-yl]benzene-1,3-diol 747412-79-9 C17H15NO4
4-[3-methyl-4-(4-methoxyphenyl)isoxazol-5-yl]benzene-1,3-diol
—— (E)-2-Cyano-N-(1-(4-hydroxyphenyl)butyl)-3-(1H-imidazol-2-yl)acrylamide 1369406-19-8 C17H18N4O2
(E)-2-Cyano-N-(1-(4-hydroxyphenyl)butyl)-3-(1H-imidazol-2-yl)acrylamide
—— 2-Hydroxy-5,6-dimethyl-hydrochinon 4382-97-2 C8H10O3
2-Hydroxy-5,6-dimethyl-hydrochinon
—— 3-n-Propyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion 93959-13-8 C13H13NO2S2
3-n-Propyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion
—— 2-n-dodecyl-mercaptohydroquinone 57322-72-2 C18H30O2S
2-n-dodecyl-mercaptohydroquinone
—— N-3-methylsalicylidene-o-hydroxyaniline 1761-43-9 C14H13NO2
N-3-methylsalicylidene-o-hydroxyaniline
—— 2-dodecanoxy-2-(3-hydroxyphenyl)-1,1-diisopropylethene 172024-49-6 C26H44O2
2-dodecanoxy-2-(3-hydroxyphenyl)-1,1-diisopropylethene
—— bis-(2-hydroxy-3-methyl-benzylidene)-<i>o</i>-phenylenediamine 6943-14-2 C22H20N2O2
bis-(2-hydroxy-3-methyl-benzylidene)-<i>o</i>-phenylenediamine
—— (2E,5E)-2,5-bis(2-hydroxy-3-methoxylbenzylidene)cyclopentanone 1261266-22-1 C21H20O5
(2E,5E)-2,5-bis(2-hydroxy-3-methoxylbenzylidene)cyclopentanone
—— (S)-N-(4-hydroxybenzyl)-3-mercapto-2-methylpropanamide 1521158-55-3 C11H15NO2S
(S)-N-(4-hydroxybenzyl)-3-mercapto-2-methylpropanamide
—— 2-methoxy-4,6-dimethylbenzene-1,3,5-triol 1609641-44-2 C9H12O4
2-methoxy-4,6-dimethylbenzene-1,3,5-triol
—— N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-4-hydroxy-5-chlorobenzamide 31526-12-2 C15H21ClN2O3
N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-4-hydroxy-5-chlorobenzamide
—— 2,6-Dimethyl-3-(methylthio)-phenol 90033-59-3 C9H12OS
2,6-Dimethyl-3-(methylthio)-phenol
—— Morpholine, 4-(2,6-dimethoxybenzyl)-, picrate 29175-70-0 C19H22N4O10
Morpholine, 4-(2,6-dimethoxybenzyl)-, picrate
—— 3,4-dibromo-2,5,6-trimethylphenol 96089-14-4 C9H10Br2O
3,4-dibromo-2,5,6-trimethylphenol
—— O-<2-(p-methoxyphenyl)ethyl> N-chlorobenzohydroxamate 112403-69-7 C16H16ClNO3
O-<2-(p-methoxyphenyl)ethyl> N-chlorobenzohydroxamate