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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-[(2R)-2-bromopropyl]-2-methoxyphenol —— C10H13BrO2
4-[(2R)-2-bromopropyl]-2-methoxyphenol
—— 4-[(2S)-2-bromopropyl]-2-methoxyphenol —— C10H13BrO2
4-[(2S)-2-bromopropyl]-2-methoxyphenol
—— 4-[(S)-hydroxy(pyridin-2-yl)methyl]benzene-1,2-diol —— C12H11NO3
4-[(S)-hydroxy(pyridin-2-yl)methyl]benzene-1,2-diol
—— (1R)-1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropan-2-one —— C11H14O4
(1R)-1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropan-2-one
—— 4-[(R)-hydroxy(pyridin-2-yl)methyl]benzene-1,2-diol —— C12H11NO3
4-[(R)-hydroxy(pyridin-2-yl)methyl]benzene-1,2-diol
—— (1S)-1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropan-2-one —— C11H14O4
(1S)-1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropan-2-one
—— 2-[[4-[(3-Chlorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol —— C19H25ClN2O2+2
2-[[4-[(3-Chlorophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol
—— 3-(3,4-Dimethylphenyl)-2-[(3,4-dimethylphenyl)imino]-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-thiazolidin-4-one —— C28H28N2O4S
3-(3,4-Dimethylphenyl)-2-[(3,4-dimethylphenyl)imino]-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-(3,4-dihydroxybenzylidene)-3-(2-methylphenyl)-2-[(2-methylphenyl)imino]-1,3-thiazolidin-4-one —— C24H20N2O3S
(2Z,5Z)-5-(3,4-dihydroxybenzylidene)-3-(2-methylphenyl)-2-[(2-methylphenyl)imino]-1,3-thiazolidin-4-one
—— N-[4-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]phenyl]acetamide —— C19H16N2O4S2
N-[4-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]phenyl]acetamide
—— (1R,2S)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid —— C12H14O5
(1R,2S)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid
—— (1S,2R)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid —— C12H14O5
(1S,2R)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid
—— rac-(1R,2R)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid —— C12H14O5
rac-(1R,2R)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid
—— (1S,2S)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid —— C12H14O5
(1S,2S)-2-(4-hydroxy-3,5-dimethoxyphenyl)cyclopropane-1-carboxylic acid
—— (E)-5-(4-hydroxybenzylidene)-3-(morpholinomethyl)-2-thioxothiazolidin-4-one —— C15H16N2O3S2
(E)-5-(4-hydroxybenzylidene)-3-(morpholinomethyl)-2-thioxothiazolidin-4-one
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H17N2O3S2+
(5E)-5-[(4-hydroxyphenyl)methylidene]-3-(morpholin-4-ium-4-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— methyl (2R)-2-(3-bromo-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H8BrF3O4
methyl (2R)-2-(3-bromo-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— methyl (2S)-3,3,3-trifluoro-2-(3-fluoro-4-hydroxyphenyl)-2-hydroxypropanoate —— C10H8F4O4
methyl (2S)-3,3,3-trifluoro-2-(3-fluoro-4-hydroxyphenyl)-2-hydroxypropanoate
—— methyl (2R)-2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H9F3O5
methyl (2R)-2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— methyl (2S)-2-(3-bromo-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H8BrF3O4
methyl (2S)-2-(3-bromo-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— methyl (2R)-3,3,3-trifluoro-2-(3-fluoro-4-hydroxyphenyl)-2-hydroxypropanoate —— C10H8F4O4
methyl (2R)-3,3,3-trifluoro-2-(3-fluoro-4-hydroxyphenyl)-2-hydroxypropanoate
—— (2S)-2-amino-2-(4-hydroxy-3-methoxyphenyl)acetic acid 54172-56-4 C9H11NO4
(2S)-2-amino-2-(4-hydroxy-3-methoxyphenyl)acetic acid
—— (E,4Z)-2,3-dichloro-4-[3-(4-hydroxyphenyl)propanoylhydrazinylidene]but-2-enoate —— C13H11Cl2N2O4-
(E,4Z)-2,3-dichloro-4-[3-(4-hydroxyphenyl)propanoylhydrazinylidene]but-2-enoate
—— Benzyl-[(3-hydroxy-4-methoxyphenyl)methyl]azanium —— C15H18NO2+
Benzyl-[(3-hydroxy-4-methoxyphenyl)methyl]azanium
—— 2-[(1S)-1-(2-cyclopentylethylamino)ethyl]phenol —— C15H23NO
2-[(1S)-1-(2-cyclopentylethylamino)ethyl]phenol
—— 2,6-dimethyl-3-[[(3S)-oxolan-3-yl]methylamino]phenol —— C13H19NO2
2,6-dimethyl-3-[[(3S)-oxolan-3-yl]methylamino]phenol
—— 4-[(1S)-1-(2-cyclopentylethylamino)ethyl]phenol —— C15H23NO
4-[(1S)-1-(2-cyclopentylethylamino)ethyl]phenol
—— (2R,4S)-2-(2-hydroxy-4-methoxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid —— C13H17NO4S
(2R,4S)-2-(2-hydroxy-4-methoxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
—— (2R,4S)-2-(2-hydroxy-4-methoxyphenyl)-5,5-dimethyl-1,3-thiazolidin-3-ium-4-carboxylate —— C13H17NO4S
(2R,4S)-2-(2-hydroxy-4-methoxyphenyl)-5,5-dimethyl-1,3-thiazolidin-3-ium-4-carboxylate
—— 2-(4-Hydroxy-3,5-dimethoxyphenyl)acetate —— C10H11O5-
2-(4-Hydroxy-3,5-dimethoxyphenyl)acetate
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-2-oxopyrido[1,2-a]pyrimidin-3-yl)-3-(2-oxo-1H-quinolin-3-yl)propanamide —— C28H24N4O6
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-2-oxopyrido[1,2-a]pyrimidin-3-yl)-3-(2-oxo-1H-quinolin-3-yl)propanamide
—— 3-(4-Hydroxyphenyl)-2-oxododecanamide —— C18H27NO3
3-(4-Hydroxyphenyl)-2-oxododecanamide
—— 2,6-dimethoxy-4-[[[(2S)-oxolan-2-yl]methylamino]methyl]phenol —— C14H21NO4
2,6-dimethoxy-4-[[[(2S)-oxolan-2-yl]methylamino]methyl]phenol
—— 2,5-Bis[6-(2-methoxybenzylamino)hexylamino]-[1,4]-benzoquinone —— C34H48N4O4
2,5-Bis[6-(2-methoxybenzylamino)hexylamino]-[1,4]-benzoquinone
—— 4-(4-Amino-2-methylcyclobuta-1,3-dien-1-yl)-2-ethylphenol —— C13H15NO
4-(4-Amino-2-methylcyclobuta-1,3-dien-1-yl)-2-ethylphenol
—— (2R,7R)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O4S
(2R,7R)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2R,7S)-7-tert-butyl-2-(2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H26N2O3S
(2R,7S)-7-tert-butyl-2-(2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— methyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methyl-5-nitrophenyl)propanoate —— C11H10F3NO6
methyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methyl-5-nitrophenyl)propanoate
—— methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methyl-5-nitrophenyl)propanoate —— C11H10F3NO6
methyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-3-methyl-5-nitrophenyl)propanoate
—— (2S,7S)-7-tert-butyl-2-(2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H26N2O3S
(2S,7S)-7-tert-butyl-2-(2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7R)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O4S
(2S,7R)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7S)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O4S
(2S,7S)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— [3-[4-(2-Hydroxyethyl)phenoxy]-3-phenylpropyl]-methylcarbamic acid —— C19H23NO4
[3-[4-(2-Hydroxyethyl)phenoxy]-3-phenylpropyl]-methylcarbamic acid
—— 5-Ethenyl-2,3-bis(hydroxymethyl)benzene-1,4-diol —— C10H12O4
5-Ethenyl-2,3-bis(hydroxymethyl)benzene-1,4-diol
—— [(E)-but-2-enyl] (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H19BrN2O5
[(E)-but-2-enyl] (4S)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-[(1S,2S,5R)-5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C16H20O3
2-[(1S,2S,5R)-5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-6-propylsulfanyl-3,4-dihydro-1H-pyridine-5-carbonitrile —— C16H18N2O3S
(4S)-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-6-propylsulfanyl-3,4-dihydro-1H-pyridine-5-carbonitrile
—— methyl (2S)-2-(3-chloro-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H8ClF3O4
methyl (2S)-2-(3-chloro-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— 4-[[4-[(4-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27BrN2O3+2
4-[[4-[(4-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— methyl (2R)-2-(3-chloro-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H8ClF3O4
methyl (2R)-2-(3-chloro-4-hydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate