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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-[7-[[2-(2,3-difluorophenyl)-7,8-dihydro-6H-imidazo[4,5-c]azocin-6-yl]methyl]-4-methyl-2,3-dihydrooxepin-5-yl]-5-methoxyphenol —— C29H27F2N3O3
2-[7-[[2-(2,3-difluorophenyl)-7,8-dihydro-6H-imidazo[4,5-c]azocin-6-yl]methyl]-4-methyl-2,3-dihydrooxepin-5-yl]-5-methoxyphenol
—— 1-(3,4-Dihydroxyphenyl)dodecan-4-one —— C18H28O3
1-(3,4-Dihydroxyphenyl)dodecan-4-one
—— (E)-3-Benzofuran-2-yl-1-(2-hydroxy-4-methoxy-phenyl)-propenone 67262-08-2 C18H14O4
(E)-3-Benzofuran-2-yl-1-(2-hydroxy-4-methoxy-phenyl)-propenone
—— 2-[[[6-Amino-2-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]diazenyl]methyl]-4-methylphenol —— C18H24N6O3
2-[[[6-Amino-2-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]diazenyl]methyl]-4-methylphenol
—— [2-Hydroxy-1-[(2-hydroxyphenyl)methylamino]ethyl]-methyl-methylidenephosphanium —— C11H17NO2P+
[2-Hydroxy-1-[(2-hydroxyphenyl)methylamino]ethyl]-methyl-methylidenephosphanium
—— N-[(Z)-[4-(dimethylamino)phenyl]methylideneamino]-2-hydroxy-3,5-dinitrobenzamide —— C16H15N5O6
N-[(Z)-[4-(dimethylamino)phenyl]methylideneamino]-2-hydroxy-3,5-dinitrobenzamide
—— 4-(Dihexylamino)-2-hexoxyphenol;4-(dihexylamino)-2-hexylphenol;4-(dihexylamino)-2-methoxy-6-methylphenol;4-methyl-2-pentan-3-yloxyphenol —— C80H139N3O7
4-(Dihexylamino)-2-hexoxyphenol;4-(dihexylamino)-2-hexylphenol;4-(dihexylamino)-2-methoxy-6-methylphenol;4-methyl-2-pentan-3-yloxyphenol
—— 4-(1-Nitrosopentyl)phenol —— C11H15NO2
4-(1-Nitrosopentyl)phenol
—— 2-Decyl-5-heptyl-6-hexyl-3-nonyl-4-octylphenol —— C46H86O
2-Decyl-5-heptyl-6-hexyl-3-nonyl-4-octylphenol
—— 4-(21-Thia-22,23,24-triazapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1(20),2,4,6,8,10,12,14,16,18-decaen-2-yl)phenol —— C26H19N3OS
4-(21-Thia-22,23,24-triazapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1(20),2,4,6,8,10,12,14,16,18-decaen-2-yl)phenol
—— ethyl (2Z)-5-(3-ethoxy-4-methoxyphenyl)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O7S
ethyl (2Z)-5-(3-ethoxy-4-methoxyphenyl)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2Z,5Z)-5-[(4-Hydroxyphenyl)methylidene]-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one —— C22H16N2O2S
(2Z,5Z)-5-[(4-Hydroxyphenyl)methylidene]-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one
—— [2-Amino-2-ethyl-3-(2-hydroxyphenyl)diaziridin-2-ium-1-yl]-(4-ethyl-4-nitrocyclohexa-1,5-dien-1-yl)methanone —— C18H23N4O4+
[2-Amino-2-ethyl-3-(2-hydroxyphenyl)diaziridin-2-ium-1-yl]-(4-ethyl-4-nitrocyclohexa-1,5-dien-1-yl)methanone
—— diethyl (2Z)-5-amino-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate —— C26H24N2O7S
diethyl (2Z)-5-amino-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate
—— ethane;2-(3H-pyrrol-5-yl)phenol —— C14H21NO
ethane;2-(3H-pyrrol-5-yl)phenol
—— (5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-(4-methylphenyl)-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C24H19N3O4S
(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-(4-methylphenyl)-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— ethyl (2Z)-5-amino-6-cyano-2-(4-hydroxy-3-methoxybenzylidene)-7-(4-hydroxy-3-methoxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate —— C26H23N3O7S
ethyl (2Z)-5-amino-6-cyano-2-(4-hydroxy-3-methoxybenzylidene)-7-(4-hydroxy-3-methoxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate
—— (5E)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H9BrN2O5S
(5E)-5-(3-bromo-2-hydroxy-5-nitrobenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione
—— [2-(2-Hydroxy-3-nitrophenyl)ethyl-propylsulfamoyl]methyl-(2-methylbutyl)carbamic acid —— C18H29N3O7S
[2-(2-Hydroxy-3-nitrophenyl)ethyl-propylsulfamoyl]methyl-(2-methylbutyl)carbamic acid
—— 3,5-Dimethylphenol;2-(methylideneamino)benzene-1,4-diol —— C15H17NO3
3,5-Dimethylphenol;2-(methylideneamino)benzene-1,4-diol
—— 5-[(Z)-[[4,6-di(piperidin-1-yl)-1,3,5-triazin-2-yl]-methylhydrazinylidene]methyl]-2-methoxyphenol —— C22H31N7O2
5-[(Z)-[[4,6-di(piperidin-1-yl)-1,3,5-triazin-2-yl]-methylhydrazinylidene]methyl]-2-methoxyphenol
—— 5-[2-[(3-Hydroxy-4-methoxyphenyl)methylidene]heptylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C22H26N2O4S
5-[2-[(3-Hydroxy-4-methoxyphenyl)methylidene]heptylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— Benzene;ethane;phenol;propane —— C21H38O
Benzene;ethane;phenol;propane
—— S-ethyl 3-(3-hydroxyphenyl)propanethioate —— C11H14O2S
S-ethyl 3-(3-hydroxyphenyl)propanethioate
—— Ethane;2-prop-2-enylphenol —— C11H16O
Ethane;2-prop-2-enylphenol
—— (5E)-3-(2-hydroxy-4-nitrophenyl)-5-[(2-methoxyphenyl)methylidene]-2-phenylimidazol-4-one —— C23H17N3O5
(5E)-3-(2-hydroxy-4-nitrophenyl)-5-[(2-methoxyphenyl)methylidene]-2-phenylimidazol-4-one
—— 3-(2,4-Dichloro-benzoyl)-5-(4-hydroxy-3-methoxy-benzylidene)-2-thioxo-imidazolidin-4-one —— C18H12Cl2N2O4S
3-(2,4-Dichloro-benzoyl)-5-(4-hydroxy-3-methoxy-benzylidene)-2-thioxo-imidazolidin-4-one
—— 2-Methoxy-5-[[[7-methyl-6-(2-propoxyphenyl)thieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]phenol —— C24H24N4O3S
2-Methoxy-5-[[[7-methyl-6-(2-propoxyphenyl)thieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]phenol
—— (5E)-2-[(4,5-dimethyl-1,3-thiazol-2-yl)hydrazinylidene]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C16H16N4O3S2
(5E)-2-[(4,5-dimethyl-1,3-thiazol-2-yl)hydrazinylidene]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-(3,4-Dihydro-1,2-benzodioxin-3-ylmethyl)-2,6-dimethoxyphenol —— C17H18O5
4-(3,4-Dihydro-1,2-benzodioxin-3-ylmethyl)-2,6-dimethoxyphenol
—— ethyl (2Z)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2Z)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methoxy-5-[(Z)-(pyridin-2-ylhydrazinylidene)methyl]phenol —— C13H13N3O2
2-methoxy-5-[(Z)-(pyridin-2-ylhydrazinylidene)methyl]phenol
—— 3,4,5-trihydroxy-N-[(Z)-1-(3-nitrophenyl)ethylideneamino]benzamide —— C15H13N3O6
3,4,5-trihydroxy-N-[(Z)-1-(3-nitrophenyl)ethylideneamino]benzamide
—— (2Z,6E)-2,6-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]-4-methylcyclohexan-1-one —— C27H28O5
(2Z,6E)-2,6-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]-4-methylcyclohexan-1-one
—— Diethyl 4-(2-hydroxy-3-nitrophenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate —— C19H22N2O7
Diethyl 4-(2-hydroxy-3-nitrophenyl)-2,6-dimethyl-3,4-dihydropyridine-3,5-dicarboxylate
—— 1-N,1-N'-dimethyl-1-N,1-N'-di(propan-2-yl)ethane-1,1-diamine;ethane;phenol —— C26H48N2O2
1-N,1-N'-dimethyl-1-N,1-N'-di(propan-2-yl)ethane-1,1-diamine;ethane;phenol
—— 2-[2-[1-(4-Chloro-2,3,5,6-tetrahydroxyphenyl)cyclobutyl]-2-(dimethylamino)-1,1-dihydroxyethyl]propane-1,1,1,2,3,3,3-heptol —— C17H26ClNO13
2-[2-[1-(4-Chloro-2,3,5,6-tetrahydroxyphenyl)cyclobutyl]-2-(dimethylamino)-1,1-dihydroxyethyl]propane-1,1,1,2,3,3,3-heptol
—— 3-[5-[(3,4-Dihydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]heptanedioic acid —— C18H19NO8S2
3-[5-[(3,4-Dihydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]heptanedioic acid
—— ethyl (2Z)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19N3O6S
ethyl (2Z)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H19BrN2O5S2
ethyl (2Z)-2-(5-bromo-2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[[Ditert-butyl-(4-methoxyphenyl)silyl]methylsulfanyl]-2,6-dimethylphenol —— C24H36O2SSi
4-[[Ditert-butyl-(4-methoxyphenyl)silyl]methylsulfanyl]-2,6-dimethylphenol
—— 4-(3,3-Dimethyl-4-pyridin-2-ylbutan-2-yl)oxy-3,5-dimethylphenol;ethane —— C23H37NO2
4-(3,3-Dimethyl-4-pyridin-2-ylbutan-2-yl)oxy-3,5-dimethylphenol;ethane
—— (3E)-3-[[2-(3,4-dihydroxyphenyl)ethylamino]methylidene]-1H-indol-2-one —— C17H16N2O3
(3E)-3-[[2-(3,4-dihydroxyphenyl)ethylamino]methylidene]-1H-indol-2-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(1-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO3S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(1-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-(3-Chloro-4-hydroxyphenyl)-6-(furan-2-yl)-2-methyl-3,4-dihydropyridine-3,5-dicarbonitrile —— C18H12ClN3O2
4-(3-Chloro-4-hydroxyphenyl)-6-(furan-2-yl)-2-methyl-3,4-dihydropyridine-3,5-dicarbonitrile
—— 2-[(4-Hydroxyphenoxy)methyl]butanamide —— C11H15NO3
2-[(4-Hydroxyphenoxy)methyl]butanamide
—— 5-tert-butyl-1-(3,3-dimethylbutyl)-3-(1-ethoxy-6-hydroxy-1-oxo-2,4-dihydro-2,4,1λ5-benzodiazaphosphinin-3-ylidene)-4-hydroxypyrrol-2-one —— C23H34N3O5P
5-tert-butyl-1-(3,3-dimethylbutyl)-3-(1-ethoxy-6-hydroxy-1-oxo-2,4-dihydro-2,4,1λ5-benzodiazaphosphinin-3-ylidene)-4-hydroxypyrrol-2-one
—— 2-Ethyl-6-methyltricyclo[9.4.0.03,7]pentadeca-1,3(7),10,12,14-pentaen-14-ol —— C18H22O
2-Ethyl-6-methyltricyclo[9.4.0.03,7]pentadeca-1,3(7),10,12,14-pentaen-14-ol
—— 1,2,4,5-Tetrafluoro-3-(2-hexyldecoxy)-6-(trioxidanylsulfanyl)benzene;1,2,5-trifluoro-3-methoxy-4-(trifluoromethyl)-6-(trioxidanylsulfanyl)benzene;2,4,5-trifluoro-3-methoxy-6-(trioxidanylsulfanyl)phenol —— C37H43F13O13S3
1,2,4,5-Tetrafluoro-3-(2-hexyldecoxy)-6-(trioxidanylsulfanyl)benzene;1,2,5-trifluoro-3-methoxy-4-(trifluoromethyl)-6-(trioxidanylsulfanyl)benzene;2,4,5-trifluoro-3-methoxy-6-(trioxidanylsulfanyl)phenol
—— 2-(5-Amino-1-hydroxypent-2-enylidene)-5-[(4-hydroxyphenyl)methylidene]-3-methylimidazolidin-4-one —— C16H19N3O3
2-(5-Amino-1-hydroxypent-2-enylidene)-5-[(4-hydroxyphenyl)methylidene]-3-methylimidazolidin-4-one