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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-Bromoethyl 2-(3,5-dihydroxyphenyl)-2,2-difluoroacetate —— C10H9BrF2O4
2-Bromoethyl 2-(3,5-dihydroxyphenyl)-2,2-difluoroacetate
—— 2-Chloro-3-octylphenol —— C14H21ClO
2-Chloro-3-octylphenol
—— (5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-6-hydroxy-3-[4-(propan-2-yl)phenyl]pyrimidine-2,4(3H,5H)-dione —— C21H19BrN2O5
(5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-6-hydroxy-3-[4-(propan-2-yl)phenyl]pyrimidine-2,4(3H,5H)-dione
—— N-[(5E)-5-(6-bromo-2-oxo-1H-indol-3-ylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-4-hydroxy-3-methoxybenzamide —— C19H12BrN3O5S2
N-[(5E)-5-(6-bromo-2-oxo-1H-indol-3-ylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-4-hydroxy-3-methoxybenzamide
—— tert-butyl N-[(Z)-(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]carbamate —— C12H13Br3N2O3
tert-butyl N-[(Z)-(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]carbamate
—— 3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-8-methoxy-1,5-dihydropyrimido[5,4-b]indole-2,4-dione —— C19H16N4O5
3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-8-methoxy-1,5-dihydropyrimido[5,4-b]indole-2,4-dione
—— N-[(Z)-(3-hydroxy-5-nitrophenyl)methylideneamino]-1,3,7-trimethyl-2,4-dioxopyrido[2,3-d]pyrimidine-6-carboxamide —— C18H16N6O6
N-[(Z)-(3-hydroxy-5-nitrophenyl)methylideneamino]-1,3,7-trimethyl-2,4-dioxopyrido[2,3-d]pyrimidine-6-carboxamide
—— 2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-2,3,3a,4-tetrahydro-1H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C28H30ClN5O4
2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-2,3,3a,4-tetrahydro-1H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— [(Z)-2-(2,5-dihydroxyphenyl)-2-nitroethenyl]-propan-2-ylazanium —— C11H15N2O4+
[(Z)-2-(2,5-dihydroxyphenyl)-2-nitroethenyl]-propan-2-ylazanium
—— (5E)-1-(2,5-dimethoxyphenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione —— C20H18N2O7
(5E)-1-(2,5-dimethoxyphenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
—— 1-(3,4-Dihydroxyphenyl)-4-methylpentan-3-one —— C12H16O3
1-(3,4-Dihydroxyphenyl)-4-methylpentan-3-one
—— 2-[[(1R,4aR,6S,8aR)-6-bromo-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-ethenylbenzene-1,4-diol —— C23H31BrO2
2-[[(1R,4aR,6S,8aR)-6-bromo-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-ethenylbenzene-1,4-diol
—— 2-[[(1R,4aS,6S,8aR)-6-bromo-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-ethenylbenzene-1,4-diol —— C23H31BrO2
2-[[(1R,4aS,6S,8aR)-6-bromo-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-ethenylbenzene-1,4-diol
—— 2-[[(1R,4aR,6S,8aR)-6-bromo-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl]-5-ethylbenzene-1,4-diol —— C23H33BrO2
2-[[(1R,4aR,6S,8aR)-6-bromo-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl]-5-ethylbenzene-1,4-diol
—— Benzene-1,3,5-triol;boric acid —— C6H9BO6
Benzene-1,3,5-triol;boric acid
—— (3,5-Dihydroxyphenoxy)boronic acid —— C6H7BO5
(3,5-Dihydroxyphenoxy)boronic acid
—— [3-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide —— C13H20BNO5S
[3-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide
—— 2-(Dimethylamino)-2-[3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide —— C16H27BN2O5S
2-(Dimethylamino)-2-[3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide
—— 2,3,4,5,6-pentachlorophenol;(9Z,12Z)-N-(1-phenylethyl)octadeca-9,12-dienamide —— C32H42Cl5NO2
2,3,4,5,6-pentachlorophenol;(9Z,12Z)-N-(1-phenylethyl)octadeca-9,12-dienamide
—— 2-[3-cyano-4-(methoxymethyl)-6-methylpyridin-2-yl]oxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C19H20N4O5
2-[3-cyano-4-(methoxymethyl)-6-methylpyridin-2-yl]oxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— ethyl 3-[(2R,5R)-5-amino-6-(tert-butyldisulfanyl)-2-[(4-hydroxyphenyl)methyl]-4-oxohexanoyl]sulfanylpropanoate —— C22H33NO5S3
ethyl 3-[(2R,5R)-5-amino-6-(tert-butyldisulfanyl)-2-[(4-hydroxyphenyl)methyl]-4-oxohexanoyl]sulfanylpropanoate
—— Phenol;prop-2-enyl dihydrogen phosphate;sulfane —— C9H15O5PS
Phenol;prop-2-enyl dihydrogen phosphate;sulfane
—— 4-[3-[[[[[[[[[[[[[[[3-(4-Hydroxy-3-methoxyphenyl)propyl-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]propyl]-2-(hydroxymethyl)phenol —— C50H116O18Si15
4-[3-[[[[[[[[[[[[[[[3-(4-Hydroxy-3-methoxyphenyl)propyl-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]propyl]-2-(hydroxymethyl)phenol
—— 5-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-4-hydroxy-2,3-dimethoxy-6-methylbenzenesulfonic acid —— C25H44O6S
5-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-4-hydroxy-2,3-dimethoxy-6-methylbenzenesulfonic acid
—— 5-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-3-hydroxy-2,4-dimethoxy-6-methylbenzenesulfonic acid —— C25H44O6S
5-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-3-hydroxy-2,4-dimethoxy-6-methylbenzenesulfonic acid
—— 3-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-4,6-dimethoxy-5-propylbenzenesulfonic acid —— C27H48O6S
3-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-4,6-dimethoxy-5-propylbenzenesulfonic acid
—— 5-Ethyl-3-(2,2,4,4,6,6-hexamethylnonan-5-yl)-2-hydroxy-4,6-dimethoxybenzenesulfonic acid —— C25H44O6S
5-Ethyl-3-(2,2,4,4,6,6-hexamethylnonan-5-yl)-2-hydroxy-4,6-dimethoxybenzenesulfonic acid
—— 3-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-5,6-dimethoxy-4-propylbenzenesulfonic acid —— C27H48O6S
3-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-5,6-dimethoxy-4-propylbenzenesulfonic acid
—— 4-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-5,6-dimethoxy-3-propylbenzenesulfonic acid —— C27H48O6S
4-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-5,6-dimethoxy-3-propylbenzenesulfonic acid
—— 2-[[[(2S)-2-[(2-hydroxy-3-methoxyphenyl)methylamino]cyclohexyl]amino]methyl]-6-methoxyphenol —— C22H30N2O4
2-[[[(2S)-2-[(2-hydroxy-3-methoxyphenyl)methylamino]cyclohexyl]amino]methyl]-6-methoxyphenol
—— 4-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-3,6-dimethoxy-5-propylbenzenesulfonic acid —— C27H48O6S
4-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-3,6-dimethoxy-5-propylbenzenesulfonic acid
—— 2-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-5-hydroxy-3,6-dimethoxy-4-propylbenzenesulfonic acid —— C27H48O6S
2-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-5-hydroxy-3,6-dimethoxy-4-propylbenzenesulfonic acid
—— 5-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-3,4-dimethoxy-6-propylbenzenesulfonic acid —— C27H48O6S
5-(2,2,4,4,6,6,8-Heptamethylnonan-5-yl)-2-hydroxy-3,4-dimethoxy-6-propylbenzenesulfonic acid
—— 4-(4-Hydroxyphenyl)butan-2-one;1-phenylbutan-2-one —— C20H24O3
4-(4-Hydroxyphenyl)butan-2-one;1-phenylbutan-2-one
—— N-[2-(3-hydroxy-4-methoxyanilino)ethyl]methanesulfonamide —— C10H16N2O4S
N-[2-(3-hydroxy-4-methoxyanilino)ethyl]methanesulfonamide
—— (2E,5Z)-5-benzylidene-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one —— C23H17N3O2S
(2E,5Z)-5-benzylidene-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-[(Z)-(4-chlorophenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one —— C17H11Cl2N3O2S
(2Z,5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-[(Z)-(4-chlorophenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one
—— 4-[(2R,3R,6E)-6-[(2E)-2,4-dihydroxypenta-2,4-dienylidene]-3-hydroxyoxan-2-yl]benzene-1,2-diol —— C16H18O6
4-[(2R,3R,6E)-6-[(2E)-2,4-dihydroxypenta-2,4-dienylidene]-3-hydroxyoxan-2-yl]benzene-1,2-diol
—— (5E)-5-[(3-fluoro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-[(E)-2-nitroethenyl]imidazol-4-one —— C14H12FN3O5
(5E)-5-[(3-fluoro-4-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-[(E)-2-nitroethenyl]imidazol-4-one
—— 2-methoxy-3-pentyl-4-[(E)-prop-1-enyl]phenol —— C15H22O2
2-methoxy-3-pentyl-4-[(E)-prop-1-enyl]phenol
—— 4-Amino-1-[4-(2-methoxyethyl)phenoxy]-4-methylpentan-2-ol —— C15H25NO3
4-Amino-1-[4-(2-methoxyethyl)phenoxy]-4-methylpentan-2-ol
—— 3-chloro-2-[1-[(Z)-hydroxyiminomethyl]cyclopropyl]-5-methoxyphenol —— C11H12ClNO3
3-chloro-2-[1-[(Z)-hydroxyiminomethyl]cyclopropyl]-5-methoxyphenol
—— 3-Formamido-2-(4-hydroxyphenyl)propanoic acid —— C10H11NO4
3-Formamido-2-(4-hydroxyphenyl)propanoic acid
—— 2-[(2-Methylpropan-2-yl)oxymethyl]oxirane;phenol —— C13H20O3
2-[(2-Methylpropan-2-yl)oxymethyl]oxirane;phenol
—— Bis[4-(2-propoxyethyl)phenyl] carbonate —— C23H30O5
Bis[4-(2-propoxyethyl)phenyl] carbonate
—— Bis[4-[2-(2-ethoxyethoxy)ethyl]phenyl] carbonate —— C25H34O7
Bis[4-[2-(2-ethoxyethoxy)ethyl]phenyl] carbonate
—— 2-hexyl-N-(2,3,5-trihydroxyphenyl)decanamide —— C22H37NO4
2-hexyl-N-(2,3,5-trihydroxyphenyl)decanamide
—— 3-amino-2-[(Z)-(3-bromo-5-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-N-[(3,4,5-trihydroxyphenyl)methyl]prop-2-enethioamide —— C17H15BrN2O5S
3-amino-2-[(Z)-(3-bromo-5-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-N-[(3,4,5-trihydroxyphenyl)methyl]prop-2-enethioamide
—— (E)-3-(3-bromo-4,5-dimethylphenyl)-N-[(3,5-dihydroxyphenyl)methyl]-2-methanimidoylprop-2-enethioamide —— C19H19BrN2O2S
(E)-3-(3-bromo-4,5-dimethylphenyl)-N-[(3,5-dihydroxyphenyl)methyl]-2-methanimidoylprop-2-enethioamide
—— 4-(2-Aminoethyl)benzene-1,2-diol;phenol —— C14H17NO3
4-(2-Aminoethyl)benzene-1,2-diol;phenol