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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
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-(2,5-dimethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-(2,5-dimethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-tert-butyl-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H15NO2S2
(5Z)-3-tert-butyl-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(4-butylphenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO3S2
(5Z)-3-(4-butylphenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-[4-(dimethylamino)phenyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H16N2O3S2
(5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-[4-(dimethylamino)phenyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrClNO3S
(5Z)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(5-nitrofuran-2-yl)prop-2-en-1-one —— C14H11NO6
(E)-1-(4-hydroxy-3-methoxyphenyl)-3-(5-nitrofuran-2-yl)prop-2-en-1-one
—— (5E)-5-[(2-hydroxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one —— C10H8N2O2S
(5E)-5-[(2-hydroxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3,4-dimethylphenyl)acetamide —— C21H19ClN2O5S
2-[(5Z)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(3,4-dimethylphenyl)acetamide
—— 2-imino-3-phenyl-5-salicylidene-thiazolidin-4-one —— C16H12N2O2S
2-imino-3-phenyl-5-salicylidene-thiazolidin-4-one
—— 5-methoxy-2-[(E,2S)-pent-3-en-2-yl]phenol —— C12H16O2
5-methoxy-2-[(E,2S)-pent-3-en-2-yl]phenol
—— 2-[[(3R)-3-(2-hydroxyethyl)-4-(thiophen-2-ylmethyl)piperazin-1-yl]methyl]-4-methoxyphenol —— C19H26N2O3S
2-[[(3R)-3-(2-hydroxyethyl)-4-(thiophen-2-ylmethyl)piperazin-1-yl]methyl]-4-methoxyphenol
—— (3S,4R)-4-(4-hydroxyphenoxy)pyrrolidin-3-ol —— C10H13NO3
(3S,4R)-4-(4-hydroxyphenoxy)pyrrolidin-3-ol
—— 4-[(E,2S)-5-hydroxypent-3-en-2-yl]oxyphenol —— C11H14O3
4-[(E,2S)-5-hydroxypent-3-en-2-yl]oxyphenol
—— (E,4S)-4-(4-hydroxyphenoxy)pent-2-enoic acid —— C11H12O4
(E,4S)-4-(4-hydroxyphenoxy)pent-2-enoic acid
—— N'-[(Z)-(3-bromo-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C15H13BrN2O6
N'-[(Z)-(3-bromo-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— (4R,6S)-4-(2-hydroxyphenyl)-3,6-dimethyl-1,3-oxazinan-2-one —— C12H15NO3
(4R,6S)-4-(2-hydroxyphenyl)-3,6-dimethyl-1,3-oxazinan-2-one
—— (4S,6R)-4-(2-hydroxyphenyl)-3,6-dimethyl-1,3-oxazinan-2-one —— C12H15NO3
(4S,6R)-4-(2-hydroxyphenyl)-3,6-dimethyl-1,3-oxazinan-2-one
—— (6E)-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H10N2O4
(6E)-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— (3E)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-ethylthiophen-2-one —— C13H11ClO2S
(3E)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-ethylthiophen-2-one
—— (3E)-5-ethyl-3-[(2-hydroxy-3-methoxyphenyl)methylidene]thiophen-2-one —— C14H14O3S
(3E)-5-ethyl-3-[(2-hydroxy-3-methoxyphenyl)methylidene]thiophen-2-one
—— (3E)-5-ethyl-3-[(2-hydroxyphenyl)methylidene]thiophen-2-one —— C13H12O2S
(3E)-5-ethyl-3-[(2-hydroxyphenyl)methylidene]thiophen-2-one
—— 2-[(2R,3S)-3-methyloxiran-2-yl]phenol —— C9H10O2
2-[(2R,3S)-3-methyloxiran-2-yl]phenol
—— (5Z)-3-(5,6-dichloro-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one —— C24H15Cl2N3O3S
(5Z)-3-(5,6-dichloro-1,3-benzothiazol-2-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylimidazol-4-one
—— 2-[(5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C21H20N2O6S
2-[(5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— (2Z)-2-[(5Z)-3-(1,3-benzodioxol-5-ylmethyl)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-3-(4-ethylpiperazin-1-yl)-3-oxopropanenitrile —— C28H27BrN4O6S
(2Z)-2-[(5Z)-3-(1,3-benzodioxol-5-ylmethyl)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-3-(4-ethylpiperazin-1-yl)-3-oxopropanenitrile
—— 4-[(2S)-3-amino-2-hydroxypropoxy]-2,3,6-trimethylphenol —— C12H19NO3
4-[(2S)-3-amino-2-hydroxypropoxy]-2,3,6-trimethylphenol
—— 4-[(1S)-1-(methylamino)-2-(propan-2-ylamino)ethyl]benzene-1,2-diol —— C12H20N2O2
4-[(1S)-1-(methylamino)-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
—— 2-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]benzene-1,3-diol —— C12H17NO3
2-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]benzene-1,3-diol
—— 4-[(S)-hydroxy-[(2R)-piperazin-2-yl]methyl]benzene-1,2-diol —— C11H16N2O3
4-[(S)-hydroxy-[(2R)-piperazin-2-yl]methyl]benzene-1,2-diol
—— 5-[[(2S)-butan-2-yl]-propylamino]benzene-1,3-diol —— C13H21NO2
5-[[(2S)-butan-2-yl]-propylamino]benzene-1,3-diol
—— (7S,8S)-7,8-diethoxybicyclo[4.2.0]octa-1(6),2,4-trien-2-ol —— C12H16O3
(7S,8S)-7,8-diethoxybicyclo[4.2.0]octa-1(6),2,4-trien-2-ol
—— 4-[(2R)-1-(cyclopropylamino)-3-hydroxypropan-2-yl]benzene-1,2-diol —— C12H17NO3
4-[(2R)-1-(cyclopropylamino)-3-hydroxypropan-2-yl]benzene-1,2-diol
—— 5-[(S)-hydroxy-[(2R)-piperidin-2-yl]methyl]benzene-1,3-diol —— C12H17NO3
5-[(S)-hydroxy-[(2R)-piperidin-2-yl]methyl]benzene-1,3-diol
—— 5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-ethylphenyl)-2-[(2-ethylphenyl)imino]-1,3-thiazolidin-4-one —— C27H25BrN2O3S
5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-ethylphenyl)-2-[(2-ethylphenyl)imino]-1,3-thiazolidin-4-one
—— 5-[[[(2R)-oxolan-2-yl]methylamino]methyl]benzene-1,3-diol —— C12H17NO3
5-[[[(2R)-oxolan-2-yl]methylamino]methyl]benzene-1,3-diol
—— 5-[[[(2S)-oxolan-2-yl]methylamino]methyl]benzene-1,3-diol —— C12H17NO3
5-[[[(2S)-oxolan-2-yl]methylamino]methyl]benzene-1,3-diol
—— 4-[(R)-hydroxy-[(2R)-piperazin-2-yl]methyl]benzene-1,2-diol —— C11H16N2O3
4-[(R)-hydroxy-[(2R)-piperazin-2-yl]methyl]benzene-1,2-diol
—— 4-[(2S)-1-hydroxy-3-(propan-2-ylamino)propan-2-yl]benzene-1,2-diol —— C12H19NO3
4-[(2S)-1-hydroxy-3-(propan-2-ylamino)propan-2-yl]benzene-1,2-diol
—— (2R)-2-(4-fluoro-2,3-dihydroxyphenyl)-2-hydroxyacetic acid —— C8H7FO5
(2R)-2-(4-fluoro-2,3-dihydroxyphenyl)-2-hydroxyacetic acid
—— (2S)-2-(3,4-dihydroxyphenyl)-4-methylpentanenitrile —— C12H15NO2
(2S)-2-(3,4-dihydroxyphenyl)-4-methylpentanenitrile
—— 5-[(1S,2S)-2-amino-1-hydroxypropyl]-2-methoxybenzene-1,3-diol —— C10H15NO4
5-[(1S,2S)-2-amino-1-hydroxypropyl]-2-methoxybenzene-1,3-diol
—— (4E)-1-(4-chlorophenyl)-4-(3,5-dibromo-2-hydroxybenzylidene)pyrazolidine-3,5-dione —— C16H9Br2ClN2O3
(4E)-1-(4-chlorophenyl)-4-(3,5-dibromo-2-hydroxybenzylidene)pyrazolidine-3,5-dione
—— (2R)-2-(3-fluoro-4,5-dihydroxyphenyl)-2-hydroxyacetic acid —— C8H7FO5
(2R)-2-(3-fluoro-4,5-dihydroxyphenyl)-2-hydroxyacetic acid
—— 4-[(1S)-1-(methylaminomethylsulfanyl)ethyl]benzene-1,2-diol —— C10H15NO2S
4-[(1S)-1-(methylaminomethylsulfanyl)ethyl]benzene-1,2-diol
—— 4-[(1R)-1-hydroxyethyl]-6-methylbenzene-1,2,3,5-tetrol —— C9H12O5
4-[(1R)-1-hydroxyethyl]-6-methylbenzene-1,2,3,5-tetrol
—— (4S)-4-[(3,4-dihydroxyphenyl)methyl]imidazolidin-2-one —— C10H12N2O3
(4S)-4-[(3,4-dihydroxyphenyl)methyl]imidazolidin-2-one
—— (7R)-7-[(propan-2-ylamino)methyl]bicyclo[4.2.0]octa-1,3,5-triene-3,4-diol —— C12H17NO2
(7R)-7-[(propan-2-ylamino)methyl]bicyclo[4.2.0]octa-1,3,5-triene-3,4-diol
—— 4-[(1S)-1-hydroxy-2-[(2S)-2-methyloxiran-2-yl]ethyl]benzene-1,3-diol —— C11H14O4
4-[(1S)-1-hydroxy-2-[(2S)-2-methyloxiran-2-yl]ethyl]benzene-1,3-diol
—— 4-[(1S)-1-hydroxyethyl]-6-methylbenzene-1,2,3,5-tetrol —— C9H12O5
4-[(1S)-1-hydroxyethyl]-6-methylbenzene-1,2,3,5-tetrol
—— 4-[(3S)-3-aminobutyl]-2-methoxybenzene-1,3-diol —— C11H17NO3
4-[(3S)-3-aminobutyl]-2-methoxybenzene-1,3-diol