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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-[(5Z)-5-[(2,6-dichlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide —— C18H11Cl2N3O6S
2-[(5Z)-5-[(2,6-dichlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-5-nitrophenyl)acetamide
—— 1-{2-[cyclopropyl(4-hydroxy-3-methoxybenzyl)amino]ethyl}-1,3-dihydro-2H-imidazol-2-one —— C16H21N3O3
1-{2-[cyclopropyl(4-hydroxy-3-methoxybenzyl)amino]ethyl}-1,3-dihydro-2H-imidazol-2-one
—— Methyl cyano[5-(3-hydroxyphenyl)-3-methyl-1,3-oxazolidin-2-ylidene]acetate —— C14H14N2O4
Methyl cyano[5-(3-hydroxyphenyl)-3-methyl-1,3-oxazolidin-2-ylidene]acetate
—— (2E)-1-(4-bromophenyl)-3-[(2-hydroxy-5-methylphenyl)amino]prop-2-en-1-one —— C16H14BrNO2
(2E)-1-(4-bromophenyl)-3-[(2-hydroxy-5-methylphenyl)amino]prop-2-en-1-one
—— (3Z)-2-amino-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile —— C15H12N4O3
(3Z)-2-amino-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile
—— 5-(4-Hydroxy-3-methoxybenzylidene)-3-pentyl-2-thioxo-1,3-thiazolidin-4-one 611185-80-9 C16H19NO3S2
5-(4-Hydroxy-3-methoxybenzylidene)-3-pentyl-2-thioxo-1,3-thiazolidin-4-one
—— 2-(2-ethylsulfanyl-6-methylpyrimidin-4-yl)oxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H20N4O4S
2-(2-ethylsulfanyl-6-methylpyrimidin-4-yl)oxy-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 2-((Dimethylamino)methyl)-3-(10-heptadecenyl)-5-methoxy-1,4-benzenediol hydrochloride —— C27H47NO3
2-((Dimethylamino)methyl)-3-(10-heptadecenyl)-5-methoxy-1,4-benzenediol hydrochloride
—— (2E,5E)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-2-(phenylimino)-1,3-thiazolidin-4-one —— C18H16N2O3S
(2E,5E)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-2-(phenylimino)-1,3-thiazolidin-4-one
—— (5Z)-5-[(2,3-dihydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O4S2
(5Z)-5-[(2,3-dihydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3,4,5-trihydroxy-N'-[(Z)-(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide —— C14H12N2O5
3,4,5-trihydroxy-N'-[(Z)-(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]benzohydrazide
—— 3-Chloro-4-fluoro-5-nitrophenol —— C6H3ClFNO3
3-Chloro-4-fluoro-5-nitrophenol
—— (E)-3-chloro-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methylprop-2-enamide —— C12H14ClNO3
(E)-3-chloro-N-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methylprop-2-enamide
—— lithium;cobalt;(2E)-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-3-oxo-N-phenylbutanamide —— C32H28CoLiN8O10+
lithium;cobalt;(2E)-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-3-oxo-N-phenylbutanamide
—— disodium;3-[(2Z)-2-(1-anilino-1,3-dioxobutan-2-ylidene)hydrazinyl]-4-hydroxy-5-nitrobenzenesulfonic acid;cobalt;(2E)-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-3-oxo-N-phenylbutanamide —— C32H28CoN8Na2O13S+2
disodium;3-[(2Z)-2-(1-anilino-1,3-dioxobutan-2-ylidene)hydrazinyl]-4-hydroxy-5-nitrobenzenesulfonic acid;cobalt;(2E)-2-[(2-hydroxy-5-nitrophenyl)hydrazinylidene]-3-oxo-N-phenylbutanamide
—— (2E,5Z)-2-[(2-chlorophenyl)imino]-5-(3-hydroxy-4-methoxybenzylidene)-1,3-thiazolidin-4-one —— C17H13ClN2O3S
(2E,5Z)-2-[(2-chlorophenyl)imino]-5-(3-hydroxy-4-methoxybenzylidene)-1,3-thiazolidin-4-one
—— (5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-[(4-nitrophenyl)amino]-2-thioxo-1,3-thiazolidin-4-one —— C17H13N3O5S2
(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-[(4-nitrophenyl)amino]-2-thioxo-1,3-thiazolidin-4-one
—— 2,4-Difluoro-5-hydroxyanisole —— C7H6F2O2
2,4-Difluoro-5-hydroxyanisole
—— 4-[(2S)-3-(azetidin-3-yl)-2-hydroxypropoxy]phenol —— C12H17NO3
4-[(2S)-3-(azetidin-3-yl)-2-hydroxypropoxy]phenol
—— 3,4,5-Trihydroxy-2-methylbenzaldehyde —— C8H8O4
3,4,5-Trihydroxy-2-methylbenzaldehyde
—— 1-(2-Hydroxyphenyl)butane-1,1,2,2,3,3-hexol —— C10H14O7
1-(2-Hydroxyphenyl)butane-1,1,2,2,3,3-hexol
—— (4E)-4-[3-(4-hydroxyphenyl)propylidene]cyclohex-2-en-1-one —— C15H16O2
(4E)-4-[3-(4-hydroxyphenyl)propylidene]cyclohex-2-en-1-one
—— 3-methoxy-6-(5,6,7-trimethoxy-1H-inden-2-yl)benzene-1,2-diol —— C19H20O6
3-methoxy-6-(5,6,7-trimethoxy-1H-inden-2-yl)benzene-1,2-diol
—— (5E)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one —— C12H10BrClN2O2S
(5E)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one
—— 2,3-Bis(2-phenylethynyl)phenol —— C22H14O
2,3-Bis(2-phenylethynyl)phenol
—— Benzyl-(2,3-dihydroxyphenyl)-methylideneazanium —— C14H14NO2+
Benzyl-(2,3-dihydroxyphenyl)-methylideneazanium
—— diethyl 2-[amino-[(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]methylidene]propanedioate —— C16H21N3O6
diethyl 2-[amino-[(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]methylidene]propanedioate
—— 5-[(Z)-[(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C16H16N4O2S
5-[(Z)-[(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— 3,4,5-Trihydroxybenzenesulfinate —— C6H5O5S-
3,4,5-Trihydroxybenzenesulfinate
—— 4-(2-Amino-3-hydroxy-6-methylphenyl)butan-2-one —— C11H15NO2
4-(2-Amino-3-hydroxy-6-methylphenyl)butan-2-one
—— 4-(3-methyl-5H-1,2,4-oxadiazol-2-yl)phenol —— C9H10N2O2
4-(3-methyl-5H-1,2,4-oxadiazol-2-yl)phenol
—— 3-[1-(Trifluoromethyl)diazirin-1-ium-1-yl]phenol —— C8H6F3N2O+
3-[1-(Trifluoromethyl)diazirin-1-ium-1-yl]phenol
—— 4-Chloro-2-fluoro-5-methoxyphenol —— C7H6ClFO2
4-Chloro-2-fluoro-5-methoxyphenol
—— 3,4,5-trihydroxy-N-[(E)-(2-methyl-1-phenylpropylidene)amino]benzamide —— C17H18N2O4
3,4,5-trihydroxy-N-[(E)-(2-methyl-1-phenylpropylidene)amino]benzamide
—— (2E,5E)-5-(2-hydroxy-3-methoxybenzylidene)-3-methyl-2-(phenylimino)-1,3-thiazolidin-4-one —— C18H16N2O3S
(2E,5E)-5-(2-hydroxy-3-methoxybenzylidene)-3-methyl-2-(phenylimino)-1,3-thiazolidin-4-one
—— [(1S)-2-(tert-butylamino)-1-(3,5-dihydroxyphenyl)ethyl] hydrogen sulfate;[(1R)-2-(tert-butylamino)-1-(3,5-dihydroxyphenyl)ethyl] hydrogen sulfate —— C24H38N2O12S2
[(1S)-2-(tert-butylamino)-1-(3,5-dihydroxyphenyl)ethyl] hydrogen sulfate;[(1R)-2-(tert-butylamino)-1-(3,5-dihydroxyphenyl)ethyl] hydrogen sulfate
—— N-[(Z)-[4-(diethylamino)phenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide —— C18H20N4O4
N-[(Z)-[4-(diethylamino)phenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide
—— N-[rac-(1S,5S,6R,7R)-7-cyclopentyl-2-oxabicyclo[3.2.0]hept-6-yl]-3-hydroxy-4-methoxybenzamide —— C19H25NO4
N-[rac-(1S,5S,6R,7R)-7-cyclopentyl-2-oxabicyclo[3.2.0]hept-6-yl]-3-hydroxy-4-methoxybenzamide
—— 3-hydroxy-4-methoxy-N-[rac-(1S,5S,6R,7S)-7-(methoxymethyl)-2-oxabicyclo[3.2.0]hept-6-yl]benzamide —— C16H21NO5
3-hydroxy-4-methoxy-N-[rac-(1S,5S,6R,7S)-7-(methoxymethyl)-2-oxabicyclo[3.2.0]hept-6-yl]benzamide
—— (6E)-4-bromo-6-[(2-hydroxy-5-nitroanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one —— C13H8BrN3O6
(6E)-4-bromo-6-[(2-hydroxy-5-nitroanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one
—— (5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C18H16N2O2S
(5Z)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(5-bromo-2,4-dihydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C16H11BrN2O3S
(5E)-5-[(5-bromo-2,4-dihydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— (5Z)-3-(4-bromobenzyl)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C18H13Br2NO4S
(5Z)-3-(4-bromobenzyl)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— N-[cyclopropyl(1-ethyl-1H-1,2,4-triazol-5-yl)methyl]-3-hydroxy-4-methoxybenzamide —— C16H20N4O3
N-[cyclopropyl(1-ethyl-1H-1,2,4-triazol-5-yl)methyl]-3-hydroxy-4-methoxybenzamide
—— N'-[(E)-(3-bromo-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C15H13BrN2O6
N'-[(E)-(3-bromo-5-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— 4-(3-Chloro-4-hydroxybenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one —— C14H18ClNO3
4-(3-Chloro-4-hydroxybenzyl)-1-(2-methoxyethyl)pyrrolidin-2-one
—— (2E)-2-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C19H13ClN2O2S
(2E)-2-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 3-(3-Hydroxyphenyl)-N-[2-(4-hydroxypiperidin-1-YL)ethyl]propanamide —— C16H24N2O3
3-(3-Hydroxyphenyl)-N-[2-(4-hydroxypiperidin-1-YL)ethyl]propanamide
—— N-{trans-3-[(3,5-dimethylisoxazol-4-yl)methoxy]tetrahydro-2H-pyran-4-yl}-3-(4-hydroxyphenyl)propanamide —— C20H26N2O5
N-{trans-3-[(3,5-dimethylisoxazol-4-yl)methoxy]tetrahydro-2H-pyran-4-yl}-3-(4-hydroxyphenyl)propanamide
—— N-[(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-4-nitrobenzenesulfonamide —— C16H10N4O8S2
N-[(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-4-nitrobenzenesulfonamide