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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-[(Cyclohexylamino)-pyridin-4-ylmethyl]-5-nitrophenol —— C18H21N3O3
2-[(Cyclohexylamino)-pyridin-4-ylmethyl]-5-nitrophenol
—— (5E)-5-(3-chloro-4-hydroxybenzylidene)-3-(propan-2-yl)-1,3-thiazolidine-2,4-dione —— C13H12ClNO3S
(5E)-5-(3-chloro-4-hydroxybenzylidene)-3-(propan-2-yl)-1,3-thiazolidine-2,4-dione
—— N-[(E)-[1-(2-anilino-2-oxoethyl)-2-oxoindol-3-ylidene]amino]-2-hydroxy-5-nitrobenzamide —— C23H17N5O6
N-[(E)-[1-(2-anilino-2-oxoethyl)-2-oxoindol-3-ylidene]amino]-2-hydroxy-5-nitrobenzamide
—— 5-Hydroxy-4-[(4-hydroxyphenyl)methyl]-1,2-oxazol-3-one —— C10H9NO4
5-Hydroxy-4-[(4-hydroxyphenyl)methyl]-1,2-oxazol-3-one
—— 4-[(3-Hydroxy-4-methoxyphenyl)methyldiazenyl]-7-methylthieno[3,2-d]pyrimidine-6-carboxylic acid —— C16H14N4O4S
4-[(3-Hydroxy-4-methoxyphenyl)methyldiazenyl]-7-methylthieno[3,2-d]pyrimidine-6-carboxylic acid
—— 3-[2-[(6-Iminocyclohexa-2,4-dien-1-ylidene)methyl]-4-[2-(2-methylprop-2-enoyloxy)ethyl]phenoxy]-2,2-dimethyl-3-oxopropanoic acid —— C24H25NO6
3-[2-[(6-Iminocyclohexa-2,4-dien-1-ylidene)methyl]-4-[2-(2-methylprop-2-enoyloxy)ethyl]phenoxy]-2,2-dimethyl-3-oxopropanoic acid
—— N-(2-hydroxy-4-nitrophenyl)-6-[(5Z)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]hexanamide —— C20H19N3O5S3
N-(2-hydroxy-4-nitrophenyl)-6-[(5Z)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]hexanamide
—— N-[(Z)-1-(3-bromophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C15H13BrN2O4
N-[(Z)-1-(3-bromophenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— N-[(Z)-(6-bromo-1,3-benzodioxol-5-yl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C15H10BrN3O6
N-[(Z)-(6-bromo-1,3-benzodioxol-5-yl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— N-[(E)-1-(5-bromothiophen-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C13H11BrN2O4S
N-[(E)-1-(5-bromothiophen-2-yl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 3-Amino-3,4,4-trihydroxy-4-(2,4,6-trihydroxyphenyl)butan-2-one —— C10H13NO7
3-Amino-3,4,4-trihydroxy-4-(2,4,6-trihydroxyphenyl)butan-2-one
—— 2-Bromo-6-prop-2-enylphenol;ethane —— C11H15BrO
2-Bromo-6-prop-2-enylphenol;ethane
—— 3-[4-[5-[Ethylsulfanyl-(2-hydroxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]phenyl]-1,2-oxazole-5-carbaldehyde —— C21H17N3O4S
3-[4-[5-[Ethylsulfanyl-(2-hydroxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]phenyl]-1,2-oxazole-5-carbaldehyde
—— Ethane;2-[1-[1-(2-hydroxyphenyl)ethyl-methylamino]ethyl]phenol —— C21H33NO2
Ethane;2-[1-[1-(2-hydroxyphenyl)ethyl-methylamino]ethyl]phenol
—— ethyl 4-(2-hydroxyphenyl)-6-propyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate —— C18H21N3O3
ethyl 4-(2-hydroxyphenyl)-6-propyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
—— 3-[(2S)-2-hydroxytridecyl]-5-methoxyphenol —— C20H34O3
3-[(2S)-2-hydroxytridecyl]-5-methoxyphenol
—— (4E)-4-(4-hydroxy-3-methyl-6-methylidenecyclohexa-2,4-dien-1-ylidene)-6-methyl-3-methylidenecyclohexa-1,5-dien-1-ol —— C16H16O2
(4E)-4-(4-hydroxy-3-methyl-6-methylidenecyclohexa-2,4-dien-1-ylidene)-6-methyl-3-methylidenecyclohexa-1,5-dien-1-ol
—— 2-Methyl-4-(3-methyl-1-methylsulfanylbut-1-enyl)phenol —— C13H18OS
2-Methyl-4-(3-methyl-1-methylsulfanylbut-1-enyl)phenol
—— (5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-(4-methylphenyl)-1,3-thiazolidine-2,4-dione —— C17H12N2O5S
(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-(4-methylphenyl)-1,3-thiazolidine-2,4-dione
—— (6E)-3-(diethylamino)-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C17H19N3O4
(6E)-3-(diethylamino)-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-[(4-Hydroxyphenyl)methyl]butanamide —— C11H15NO2
2-[(4-Hydroxyphenyl)methyl]butanamide
—— 4-[[[(9E)-10-imidazol-1-yl-6-methylideneundeca-1,7,9-trien-2-yl]amino]methyl]benzene-1,2-diol —— C22H26N3O2+
4-[[[(9E)-10-imidazol-1-yl-6-methylideneundeca-1,7,9-trien-2-yl]amino]methyl]benzene-1,2-diol
—— 4-(1-Diethoxyphosphoryl-2-pyrazin-2-yliminoethyl)-2-methoxy-6-methylphenol —— C18H24N3O5P
4-(1-Diethoxyphosphoryl-2-pyrazin-2-yliminoethyl)-2-methoxy-6-methylphenol
—— 5-[(2,4-dihydroxyphenyl)hydrazinylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C9H7N3O3S2
5-[(2,4-dihydroxyphenyl)hydrazinylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-Hydroxy-3-methoxy-4-methyl-2-(trifluoromethoxy)benzenesulfinic acid —— C9H9F3O5S
5-Hydroxy-3-methoxy-4-methyl-2-(trifluoromethoxy)benzenesulfinic acid
—— (10E)-7-(4-fluorophenyl)-10-(4-hydroxy-3,5-dinitrobenzylidene)-5,7-dihydro-6H-benzo[h][1,3]thiazolo[2,3-b]quinazolin-9(10H)-one —— C27H17FN4O6S
(10E)-7-(4-fluorophenyl)-10-(4-hydroxy-3,5-dinitrobenzylidene)-5,7-dihydro-6H-benzo[h][1,3]thiazolo[2,3-b]quinazolin-9(10H)-one
—— 4,4-Dicyclohexyloxy-2,2-diethyl-6,6-dimethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]piperidine —— C34H55NO5
4,4-Dicyclohexyloxy-2,2-diethyl-6,6-dimethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]piperidine
—— 6-(2-Ethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyldiazenyl]thieno[3,2-d]pyrimidin-7-ol —— C23H22N4O5S
6-(2-Ethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyldiazenyl]thieno[3,2-d]pyrimidin-7-ol
—— 4-[(4-chloro-1H-pyrrol-2-yl)methylidene]-5-[2-(4-hydroxyphenyl)ethylidene]pyrazolidin-3-one —— C16H14ClN3O2
4-[(4-chloro-1H-pyrrol-2-yl)methylidene]-5-[2-(4-hydroxyphenyl)ethylidene]pyrazolidin-3-one
—— N-[1-chloro-2-(4-hydroxyphenyl)ethyl]-N-iodoacetamide —— C10H11ClINO2
N-[1-chloro-2-(4-hydroxyphenyl)ethyl]-N-iodoacetamide
—— 6-(2-Ethoxyphenyl)-4-[(3-hydroxy-4-methoxyphenyl)methyldiazenyl]thieno[3,2-d]pyrimidine-7-carbonitrile —— C23H19N5O3S
6-(2-Ethoxyphenyl)-4-[(3-hydroxy-4-methoxyphenyl)methyldiazenyl]thieno[3,2-d]pyrimidine-7-carbonitrile
—— 2-[2-[5-(Diethylaminomethyl)furan-2-yl]-3,5-dihydroxyphenyl]acetic acid —— C17H21NO5
2-[2-[5-(Diethylaminomethyl)furan-2-yl]-3,5-dihydroxyphenyl]acetic acid
—— 3-(5-Chloro-2-hydroxyphenyl)-2-(4-(hydroxy(oxido)amino)cyclohexyl)acrylonitrile —— C15H15ClN2O3
3-(5-Chloro-2-hydroxyphenyl)-2-(4-(hydroxy(oxido)amino)cyclohexyl)acrylonitrile
—— Ethane;4-methylphenol;phenol;propane —— C18H28O2
Ethane;4-methylphenol;phenol;propane
—— (1'S,4R)-1,1-dioxo-2-propylspiro[1,2,5-thiadiazolidine-4,13'-tricyclo[8.2.1.03,8]trideca-3(8),4,6-triene]-5'-ol —— C17H24N2O3S
(1'S,4R)-1,1-dioxo-2-propylspiro[1,2,5-thiadiazolidine-4,13'-tricyclo[8.2.1.03,8]trideca-3(8),4,6-triene]-5'-ol
—— 2-(4-ethoxyphenyl)ethyl N-tert-butyl-N-[3-(2-oxoethylsulfanyl)propyl]carbamate —— C20H31NO4S
2-(4-ethoxyphenyl)ethyl N-tert-butyl-N-[3-(2-oxoethylsulfanyl)propyl]carbamate
—— 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-6-nitro-1H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one —— C14H11N5O5
5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-6-nitro-1H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one
—— N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]hexanamide —— C14H20N2O2
N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]hexanamide
—— (2Z,5Z)-2,5-bis[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enylidene]cyclopentanone —— C25H24O5
(2Z,5Z)-2,5-bis[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enylidene]cyclopentanone
—— 2-hydroxy-N-[(Z)-(2-methoxyphenyl)methylideneamino]-5-nitrobenzamide —— C15H13N3O5
2-hydroxy-N-[(Z)-(2-methoxyphenyl)methylideneamino]-5-nitrobenzamide
—— 2-(4-chlorophenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-oxopropanamide —— C18H18ClNO4
2-(4-chlorophenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-oxopropanamide
—— methyl (2Z)-2-(3-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H18N2O4S
methyl (2Z)-2-(3-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4E)-2-chloro-4-[(2-hydroxy-3-methoxy-phenyl)methylene]oxazol-5-one —— C11H8ClNO4
(4E)-2-chloro-4-[(2-hydroxy-3-methoxy-phenyl)methylene]oxazol-5-one
—— (5Z)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C15H13N3O3
(5Z)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 2-hydroxy-N'-[(Z)-(3-methoxy-5-nitro-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide —— C15H12N4O8
2-hydroxy-N'-[(Z)-(3-methoxy-5-nitro-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-5-nitrobenzohydrazide
—— N-[1-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-dienyl]acetamide —— C15H16N2O4
N-[1-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-dienyl]acetamide
—— (5E)-5-[(4-bromo-2-hydroxyphenyl)methylidene]-3-(4-methylphenyl)-1,3-thiazolidine-2,4-dione —— C17H12BrNO3S
(5E)-5-[(4-bromo-2-hydroxyphenyl)methylidene]-3-(4-methylphenyl)-1,3-thiazolidine-2,4-dione
—— (5Z)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-2-methylideneimidazolidin-4-one —— C12H12N2O2
(5Z)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-2-methylideneimidazolidin-4-one
—— 4-(2-hydroxyphenyl)-1-[(2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-5-[2-(4-hydroxyphenyl)ethyl]oxan-2-yl]butane-1,2-dione —— C23H26O9
4-(2-hydroxyphenyl)-1-[(2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-5-[2-(4-hydroxyphenyl)ethyl]oxan-2-yl]butane-1,2-dione
—— 3,3-dimethylbutan-2-yl 6-(3-cyano-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate —— C20H25N3O5
3,3-dimethylbutan-2-yl 6-(3-cyano-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate