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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
—— ethyl (2E)-2-[2-(5-chloro-2-hydroxyphenyl)ethylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20Cl2N2O4S
ethyl (2E)-2-[2-(5-chloro-2-hydroxyphenyl)ethylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[3-[(1S,15R)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide —— C25H31NO6
N-[3-[(1S,15R)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide
—— 3-Amino-4-aminooxybenzene-1,2-diol —— C6H8N2O3
3-Amino-4-aminooxybenzene-1,2-diol
—— 2-[(71-Hydroxy-5,7,13,19,21,27,33,35,41,47,49,55,63-tridecamethyl-2,10,16,24,30,38,44,52-octaoxo-58,61,65,68-tetraoxa-3,9,17,23,31,37,45,51-octazadecacyclo[27.27.13.14,8.111,15.118,22.132,36.139,43.146,50.025,69.053,57]pentaheptaconta-1(57),4,6,8(75),11(74),12,14,18(73),19,21,25(69),26,28,32,34,36(72),39,41,43(71),46(70),47,49,53,55-tetracosaen-63-yl)methoxy]ethyl 2-bromo-2-methylpropanoate —— C83H89BrN8O16
2-[(71-Hydroxy-5,7,13,19,21,27,33,35,41,47,49,55,63-tridecamethyl-2,10,16,24,30,38,44,52-octaoxo-58,61,65,68-tetraoxa-3,9,17,23,31,37,45,51-octazadecacyclo[27.27.13.14,8.111,15.118,22.132,36.139,43.146,50.025,69.053,57]pentaheptaconta-1(57),4,6,8(75),11(74),12,14,18(73),19,21,25(69),26,28,32,34,36(72),39,41,43(71),46(70),47,49,53,55-tetracosaen-63-yl)methoxy]ethyl 2-bromo-2-methylpropanoate
—— (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-nitrophenyl)-2-thioxothiazolidin-4-one —— C18H14N2O6S2
(Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-nitrophenyl)-2-thioxothiazolidin-4-one
—— 5-(Dichloromethyl)benzene-1,2,3-triol —— C7H6Cl2O3
5-(Dichloromethyl)benzene-1,2,3-triol
—— ethyl (2Z)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19N3O6S
ethyl (2Z)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2Z,5E)-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C20H18Br2N2O4S
(2Z,5E)-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— 4-[2-(4-Hydroxy-3,5-dimethoxyphenyl)ethylimino]-1,1-dioxo-5-phenyl-2-propan-2-yl-1,2-thiazolidin-3-one —— C22H26N2O6S
4-[2-(4-Hydroxy-3,5-dimethoxyphenyl)ethylimino]-1,1-dioxo-5-phenyl-2-propan-2-yl-1,2-thiazolidin-3-one
—— 2-[2-(4-Hydroxyphenyl)ethoxycarbonylamino]ethyl 2,2-dimethylbutanoate —— C17H25NO5
2-[2-(4-Hydroxyphenyl)ethoxycarbonylamino]ethyl 2,2-dimethylbutanoate
—— Methyl 1-(4-hydroxy-3,5-dimethylphenyl)cyclopropane-1-carboxylate —— C13H16O3
Methyl 1-(4-hydroxy-3,5-dimethylphenyl)cyclopropane-1-carboxylate
—— (5E)-5-(5-chloro-2-hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one —— C16H10ClNO2S2
(5E)-5-(5-chloro-2-hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one
—— 4-[[(6-Benzylthieno[2,3-d]pyrimidin-4-yl)diazenyl]methyl]-2-methoxyphenol —— C21H18N4O2S
4-[[(6-Benzylthieno[2,3-d]pyrimidin-4-yl)diazenyl]methyl]-2-methoxyphenol
—— 2-Bromo-6-prop-2-enylphenol;ethane;formonitrile —— C12H16BrNO
2-Bromo-6-prop-2-enylphenol;ethane;formonitrile
—— Ethane;ethyl propanoate;2-methylphenol —— C14H24O3
Ethane;ethyl propanoate;2-methylphenol
—— 2-methoxy-5-[(Z)-[[2-nitro-4-(trifluoromethyl)phenyl]hydrazinylidene]methyl]phenol —— C15H12F3N3O4
2-methoxy-5-[(Z)-[[2-nitro-4-(trifluoromethyl)phenyl]hydrazinylidene]methyl]phenol
—— 2,4-Di(nonyl)phenol;4-dodecyl-2-methylphenol —— C43H74O2
2,4-Di(nonyl)phenol;4-dodecyl-2-methylphenol
—— 3-[2-(3-Hydroxyphenyl)-1,4-oxazin-4-yl]propanoic acid —— C13H13NO4
3-[2-(3-Hydroxyphenyl)-1,4-oxazin-4-yl]propanoic acid
—— (2R)-1-(4-hydroxy-3-methoxy-5-propylbenzoyl)azetidine-2-carboxylic acid —— C15H19NO5
(2R)-1-(4-hydroxy-3-methoxy-5-propylbenzoyl)azetidine-2-carboxylic acid
—— [(Z)-(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]thiourea —— C8H6Br3N3OS
[(Z)-(2,4,6-tribromo-3-hydroxyphenyl)methylideneamino]thiourea
—— Ethyl 5-(4-hydroxyphenyl)-7-methyl-2-[(5-methyl-2-furyl)methylene]-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C22H20N2O5S
Ethyl 5-(4-hydroxyphenyl)-7-methyl-2-[(5-methyl-2-furyl)methylene]-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— 4-(4-Methylidenecyclohexyl)oxyphenol —— C13H16O2
4-(4-Methylidenecyclohexyl)oxyphenol
—— 3-(1-Diazenylethyl)phenol —— C8H10N2O
3-(1-Diazenylethyl)phenol
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-methylthiourea —— C9H11N3OS
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-methylthiourea
—— 4-(4-Amino-2-phenylbutan-2-yl)oxy-3-methylphenol —— C17H21NO2
4-(4-Amino-2-phenylbutan-2-yl)oxy-3-methylphenol
—— 4-[(Methyldiazenyl)methyl]benzene-1,2-diol —— C8H10N2O2
4-[(Methyldiazenyl)methyl]benzene-1,2-diol
—— 6-[(4-hydroxyphenyl)methyl]-1H-pyrazin-2-one —— C11H10N2O2
6-[(4-hydroxyphenyl)methyl]-1H-pyrazin-2-one
—— 4-[1-cyclohexyl-5-hydroxy-3-[(2-hydroxyphenyl)methyl]-2-oxoimidazol-4-yl]-N-hydroxybutanamide —— C20H27N3O5
4-[1-cyclohexyl-5-hydroxy-3-[(2-hydroxyphenyl)methyl]-2-oxoimidazol-4-yl]-N-hydroxybutanamide
—— 3-[3-(3-Hydroxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]propanoic acid —— C16H18O3
3-[3-(3-Hydroxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]propanoic acid
—— 2-Heptadeca-1,8,11-trienyl-3,5,6-trimethylbenzene-1,4-diol —— C26H40O2
2-Heptadeca-1,8,11-trienyl-3,5,6-trimethylbenzene-1,4-diol
—— 4-[2,3-Dihydroxy-6-methoxy-4-(methoxymethyl)benzoyl]-3-[(4-ethylphenyl)methoxy]-5-methylcyclohex-3-en-1-one —— C26H30O7
4-[2,3-Dihydroxy-6-methoxy-4-(methoxymethyl)benzoyl]-3-[(4-ethylphenyl)methoxy]-5-methylcyclohex-3-en-1-one
—— 5-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-2-cyano-N-[(3,4-dihydroxyphenyl)methyl]penta-2,4-dienamide —— C31H44N2O5Si2
5-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-2-cyano-N-[(3,4-dihydroxyphenyl)methyl]penta-2,4-dienamide
—— (1S,4S)-5-[(1S)-1-(4-hydroxy-2,3-dimethylphenyl)ethyl]-2,5-diazabicyclo[2.2.1]heptane-2-carbaldehyde —— C16H22N2O2
(1S,4S)-5-[(1S)-1-(4-hydroxy-2,3-dimethylphenyl)ethyl]-2,5-diazabicyclo[2.2.1]heptane-2-carbaldehyde
—— 2-Decyl-4-methylphenol;2,4-di(nonyl)phenol;4-hexylphenol;4-methylphenol —— C60H96O4
2-Decyl-4-methylphenol;2,4-di(nonyl)phenol;4-hexylphenol;4-methylphenol
—— 7-(4-Hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-5-imino-3-oxo-6,7-dihydro-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile —— C22H14N4O3S
7-(4-Hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-5-imino-3-oxo-6,7-dihydro-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile
—— N-[(Z)-1-[4-(cyclohexanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide —— C22H25N3O5
N-[(Z)-1-[4-(cyclohexanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide
—— 3-(2-Amino-1,1-dihydroxyethyl)benzene-1,2,4,5-tetrol —— C8H11NO6
3-(2-Amino-1,1-dihydroxyethyl)benzene-1,2,4,5-tetrol
—— (5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H10N2O4S2
(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-cyclohexyl-4-hydroxy-5-[(4-hydroxyphenyl)methyl]-1H-imidazole-2-thione —— C16H20N2O2S
3-cyclohexyl-4-hydroxy-5-[(4-hydroxyphenyl)methyl]-1H-imidazole-2-thione
—— 4H-1,2,3-benzothiadiazin-7-ol —— C7H6N2OS
4H-1,2,3-benzothiadiazin-7-ol
—— 12-(4-Hydroxy-3-methoxyphenyl)-10-oxododecanoic acid —— C19H28O5
12-(4-Hydroxy-3-methoxyphenyl)-10-oxododecanoic acid
—— (E)-2-[4-(2,4-dimethylphenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C21H18N2O2S
(E)-2-[4-(2,4-dimethylphenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 3-[3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]propanoic acid —— C18H22O5
3-[3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-bicyclo[2.2.1]hept-5-enyl]propanoic acid
—— 4-(2,2,2-Trifluoro-1-nitrosoethyl)benzene-1,3-diol —— C8H6F3NO3
4-(2,2,2-Trifluoro-1-nitrosoethyl)benzene-1,3-diol
—— 2-(9-Nitrononyl)phenol —— C15H23NO3
2-(9-Nitrononyl)phenol
—— 1-methoxy-4-prenylphloroglucin —— C12H16O3
1-methoxy-4-prenylphloroglucin
—— (5Z)-3-(2-methylphenyl)-2-(2-methylphenyl)imino-5-[(2,4,6-tribromo-3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C24H17Br3N2O2S
(5Z)-3-(2-methylphenyl)-2-(2-methylphenyl)imino-5-[(2,4,6-tribromo-3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— Ethyl 2-{[4-(benzyloxy)-3-methoxyphenyl]methylene}-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-A]pyrimidine-6(3H)-carboxylate —— C32H29ClN2O7S
Ethyl 2-{[4-(benzyloxy)-3-methoxyphenyl]methylene}-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-A]pyrimidine-6(3H)-carboxylate
—— 8-ethyl 6-methyl 5-amino-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate —— C25H22N2O7S
8-ethyl 6-methyl 5-amino-2-(4-hydroxybenzylidene)-7-(4-hydroxyphenyl)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarboxylate
—— 1-(1-adamantyl)-3-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]urea —— C19H24BrN3O3
1-(1-adamantyl)-3-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]urea