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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-(ethoxymethylidene)-3-(3-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H11NO3S2
(5Z)-5-(ethoxymethylidene)-3-(3-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-[(8E,11E)-pentadeca-8,11-dienyl]phenol;3-[(8E,11E)-pentadeca-8,11,14-trienyl]phenol;3-[(E)-pentadec-8-enyl]phenol —— C63H96O3
3-[(8E,11E)-pentadeca-8,11-dienyl]phenol;3-[(8E,11E)-pentadeca-8,11,14-trienyl]phenol;3-[(E)-pentadec-8-enyl]phenol
—— methyl (2Z)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H17ClN2O4S
methyl (2Z)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C14H13BrN2O4S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[4-[(5Z)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-yl]-1,3-thiazol-4-one —— C24H20N4O4S2
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[4-[(5Z)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-yl]-1,3-thiazol-4-one
—— (5E)-5-[(2,4-dihydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H11NO3S2
(5E)-5-[(2,4-dihydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2Z)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H10N2O5S
(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2Z)-2-(4-hydroxy-3-methoxybenzylidene)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (Z)-3-(5-Hydroxy-2-nitro-phenylcarbamoyl)-acrylic acid —— C10H8N2O6
(Z)-3-(5-Hydroxy-2-nitro-phenylcarbamoyl)-acrylic acid
—— (4E)-4-[3-[(4-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C22H20N2O4
(4E)-4-[3-[(4-hydroxy-3-methoxyphenyl)methyl]-1H-benzimidazol-2-ylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— ethyl (2Z)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O7S
ethyl (2Z)-5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Cambridge id 5877568 —— C13H11N3O6
Cambridge id 5877568
—— (4Z)-4-[(2-hydroxy-5-nitroanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one —— C18H16N4O4
(4Z)-4-[(2-hydroxy-5-nitroanilino)methylidene]-5-methyl-2-(4-methylphenyl)pyrazol-3-one
—— (5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C10H7N3O4S
(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (6E)-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]-2-methylcyclohexa-2,4-dien-1-one —— C16H17NO2
(6E)-6-[(2-hydroxy-4,5-dimethylanilino)methylidene]-2-methylcyclohexa-2,4-dien-1-one
—— 2-Bromo-6-methoxy-4-(thiomorpholin-4-ylmethyl)phenol —— C12H16BrNO2S
2-Bromo-6-methoxy-4-(thiomorpholin-4-ylmethyl)phenol
—— 5-[(E)-tridec-8-enyl]benzene-1,3-diol —— C19H30O2
5-[(E)-tridec-8-enyl]benzene-1,3-diol
—— N-(2-hydroxy-3-nitrobenzyl)-2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]acetamide —— C11H12N6O4S
N-(2-hydroxy-3-nitrobenzyl)-2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]acetamide
—— 5-[(3,5-dibromo-2-hydroxybenzyl)amino]-1H-pyrazole-4-carbonitrile —— C11H8Br2N4O
5-[(3,5-dibromo-2-hydroxybenzyl)amino]-1H-pyrazole-4-carbonitrile
—— (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-(6-methyl-1H-1,3-benzodiazol-2-YL)prop-2-enenitrile —— C18H15N3O2
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-(6-methyl-1H-1,3-benzodiazol-2-YL)prop-2-enenitrile
—— (5E)-5-(4-hydroxy-3-iodobenzylidene)-3-propyl-2-thioxo-1,3-thiazolidin-4-one —— C13H12INO2S2
(5E)-5-(4-hydroxy-3-iodobenzylidene)-3-propyl-2-thioxo-1,3-thiazolidin-4-one
—— (5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1-(4-methylphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione —— C20H18N2O6
(5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-1-(4-methylphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione
—— ethyl (2E)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20BrClN2O5S
ethyl (2E)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(9,12-Diphenyl-8,10,13-trioxa-12-phospha-9-boranuidatricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-yl)phenol;triethylazanium —— C32H37BNO4P
2-(9,12-Diphenyl-8,10,13-trioxa-12-phospha-9-boranuidatricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-yl)phenol;triethylazanium
—— (2E)-but-2-en-1-yl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C17H19BrN2O5
(2E)-but-2-en-1-yl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— (2Z)-5-hydroxy-4-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]furan-3-one —— C17H12O5
(2Z)-5-hydroxy-4-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]furan-3-one
—— 3-(4,5-diamino-1,2-oxazol-3-yl)phenol —— C9H9N3O2
3-(4,5-diamino-1,2-oxazol-3-yl)phenol
—— 2-[4-(3-Hydroxyphenyl)-1,2,5-oxadiazol-3-yl]acetic acid —— C10H8N2O4
2-[4-(3-Hydroxyphenyl)-1,2,5-oxadiazol-3-yl]acetic acid
—— 2-[2-(3-Bromo-4-fluorophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol —— C23H19BrClFN2O2
2-[2-(3-Bromo-4-fluorophenyl)-6-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]-6-methoxyphenol
—— Hydroxy-[(2-hydroxyphenyl)methylidene]azanium —— C7H8NO2+
Hydroxy-[(2-hydroxyphenyl)methylidene]azanium
—— (Z)-1-(2,4-dihydroxyphenyl)-3-[(1S)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one —— C16H16O4
(Z)-1-(2,4-dihydroxyphenyl)-3-[(1S)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one
—— (E)-1-(2,4-dihydroxyphenyl)-3-[(1R)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one —— C16H16O4
(E)-1-(2,4-dihydroxyphenyl)-3-[(1R)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one
—— (E)-1-(2,4-dihydroxyphenyl)-3-[(1S)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one —— C16H16O4
(E)-1-(2,4-dihydroxyphenyl)-3-[(1S)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one
—— (Z)-1-(2,4-dihydroxyphenyl)-3-[(1R)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one —— C16H16O4
(Z)-1-(2,4-dihydroxyphenyl)-3-[(1R)-4-methoxycyclohexa-2,4-dien-1-yl]prop-2-en-1-one
—— 2-(4-chloro-3,5-dimethylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H19ClN2O4
2-(4-chloro-3,5-dimethylphenoxy)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— [8-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-7-oxonaphthalen-1-yl]-methylcarbamic acid —— C18H13N5O8
[8-[(2-hydroxy-3,5-dinitrophenyl)hydrazinylidene]-7-oxonaphthalen-1-yl]-methylcarbamic acid
—— 5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C11H10N2O3S
5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— N-[(Z)-(1,2-dimethylindol-3-yl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C18H16N4O4
N-[(Z)-(1,2-dimethylindol-3-yl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— 2-[3-cyano-4-(methoxymethyl)-6-methyl-2-oxopyridin-1-yl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C19H20N4O5
2-[3-cyano-4-(methoxymethyl)-6-methyl-2-oxopyridin-1-yl]-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 5-[[[(1R)-1-(1H-benzimidazol-2-yl)-2-methylpropyl]amino]methyl]-2-methoxyphenol —— C19H23N3O2
5-[[[(1R)-1-(1H-benzimidazol-2-yl)-2-methylpropyl]amino]methyl]-2-methoxyphenol
—— 5-[(3-Bromo-4-hydroxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one —— C10H7BrN2O2S
5-[(3-Bromo-4-hydroxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
—— 2-(3-Hydroxyphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C19H16N2O3S
2-(3-Hydroxyphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 4-Bromo-2-[6-(4-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol —— C22H18Br2ClN2O+
4-Bromo-2-[6-(4-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]phenol
—— 2-methoxy-5-[[[(1R)-1-[4-(2-methylpropyl)phenyl]ethyl]amino]methyl]phenol —— C20H27NO2
2-methoxy-5-[[[(1R)-1-[4-(2-methylpropyl)phenyl]ethyl]amino]methyl]phenol
—— 4-Bromo-2-[6-(4-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol —— C22H17Br2ClN2O
4-Bromo-2-[6-(4-bromophenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidin-4-yl]phenol
—— 2-methoxy-5-[[[(1S)-1-[4-(2-methylpropyl)phenyl]ethyl]amino]methyl]phenol —— C20H27NO2
2-methoxy-5-[[[(1S)-1-[4-(2-methylpropyl)phenyl]ethyl]amino]methyl]phenol
—— 3-(1,3-Benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)but-3-enoic acid —— C18H15NO4S
3-(1,3-Benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)but-3-enoic acid
—— (2S)-2-(3-chlorophenoxy)-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide —— C17H18ClNO4
(2S)-2-(3-chlorophenoxy)-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide
—— (2R)-2-(4-bromophenoxy)-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide —— C17H18BrNO4
(2R)-2-(4-bromophenoxy)-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide