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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
—— (4E)-2-amino-6-(3-chloro-2-hydroxy-5-methylphenyl)-4-(6-oxocyclohexa-2,4-dien-1-ylidene)-1H-pyridine-3-carbonitrile —— C19H14ClN3O2
(4E)-2-amino-6-(3-chloro-2-hydroxy-5-methylphenyl)-4-(6-oxocyclohexa-2,4-dien-1-ylidene)-1H-pyridine-3-carbonitrile
—— [4-(2,4-Dihydroxyphenyl)sulfanyl-2,5-dimethyl-3-oxocyclohexyl] octanoate —— C22H32O5S
[4-(2,4-Dihydroxyphenyl)sulfanyl-2,5-dimethyl-3-oxocyclohexyl] octanoate
—— 2-methoxy-5-[(Z)-[(5-nitropyridin-2-yl)hydrazinylidene]methyl]phenol —— C13H12N4O4
2-methoxy-5-[(Z)-[(5-nitropyridin-2-yl)hydrazinylidene]methyl]phenol
—— (5Z)-5-(3-hydroxybenzylidene)-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one —— C15H15NO3S2
(5Z)-5-(3-hydroxybenzylidene)-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-methyl-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H14Br2N2O2S
(5Z)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-methyl-2-(4-methylphenyl)imino-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-(3-bromo-4-hydroxy-5-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-(3-bromo-4-hydroxy-5-methoxybenzylidene)-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(5-Hydroxy-2-nitrophenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C14H11N3O5S
5-[(5-Hydroxy-2-nitrophenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (5E)-5-(3-bromo-4-hydroxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one —— C11H8BrNO2S2
(5E)-5-(3-bromo-4-hydroxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one
—— 4-[1-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-ylethenyl]-2-methoxy-6-methylphenol —— C21H28NO5P
4-[1-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-ylethenyl]-2-methoxy-6-methylphenol
—— 3-Hydroxy-2-methoxy-6-prop-1-enylbenzaldehyde —— C11H12O3
3-Hydroxy-2-methoxy-6-prop-1-enylbenzaldehyde
—— 2-(8,8-Diethoxyoctyl)phenol —— C18H30O3
2-(8,8-Diethoxyoctyl)phenol
—— ethyl (2Z)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2Z)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— tert-butyl N-[4-[1-(4-hydroxyphenyl)cyclobutyl]-3-methylbutyl]carbamate —— C20H31NO3
tert-butyl N-[4-[1-(4-hydroxyphenyl)cyclobutyl]-3-methylbutyl]carbamate
—— 4-[[(3S,4R)-4-methylpyrrolidin-3-yl]methyl]phenol;hydrochloride —— C12H18ClNO
4-[[(3S,4R)-4-methylpyrrolidin-3-yl]methyl]phenol;hydrochloride
—— N-[(Z)-(2,4-dibromo-5-hydroxyphenyl)methylideneamino]-2-thiophen-2-ylacetamide —— C13H10Br2N2O2S
N-[(Z)-(2,4-dibromo-5-hydroxyphenyl)methylideneamino]-2-thiophen-2-ylacetamide
—— 5-[(Z)-[(3,5-dichloropyridin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C13H11Cl2N3O2
5-[(Z)-[(3,5-dichloropyridin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— (2,5-Dihydroxypyrrol-1-yl) 3-(4-hydroxyphenoxy)propanoate —— C13H13NO6
(2,5-Dihydroxypyrrol-1-yl) 3-(4-hydroxyphenoxy)propanoate
—— 2-cyano-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C11H11N3O3
2-cyano-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— Ethyl 2-(3,4-dihydroxyphenyl)prop-2-enoate —— C11H12O4
Ethyl 2-(3,4-dihydroxyphenyl)prop-2-enoate
—— 3-(2-chloro-4-hydroxyphenyl)-N-propylpropanamide —— C12H16ClNO2
3-(2-chloro-4-hydroxyphenyl)-N-propylpropanamide
—— N-[(E)-2-(2,5-dihydroxyphenyl)vinyl]-N-methyl-formamide —— C10H11NO3
N-[(E)-2-(2,5-dihydroxyphenyl)vinyl]-N-methyl-formamide
—— 2,6-Diethyl-4,4-dimethoxy-2,3,6-trimethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]piperidine —— C25H41NO5
2,6-Diethyl-4,4-dimethoxy-2,3,6-trimethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]piperidine
—— Ethane;2-methylprop-1-ene;phenol —— C12H20O
Ethane;2-methylprop-1-ene;phenol
—— [(3S)-3-amino-3-carboxypropyl]-dihydroxy-(2-hydroxy-5-nitrobenzoyl)phosphanium —— C11H14N2O8P+
[(3S)-3-amino-3-carboxypropyl]-dihydroxy-(2-hydroxy-5-nitrobenzoyl)phosphanium
—— (5Z)-5-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-3-(4-nitrophenyl)-2-thioxo-1,3-thiazolidin-4-one —— C20H16N2O5S2
(5Z)-5-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-3-(4-nitrophenyl)-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-5-(2-hydroxybenzylidene)-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one —— C15H15NO3S2
(5Z)-5-(2-hydroxybenzylidene)-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one
—— 6-(3-Hydroxy-2-methylphenyl)hexanoic acid —— C13H18O3
6-(3-Hydroxy-2-methylphenyl)hexanoic acid
—— 2-(Ethoxymethoxy)benzene-1,3-diol —— C9H12O4
2-(Ethoxymethoxy)benzene-1,3-diol
—— 6-(3-bromo-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid —— C13H13BrN2O5
6-(3-bromo-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid
—— 3-[4-(Benzimidazol-1-yl)butan-2-ylamino]-2-methoxyphenol —— C18H21N3O2
3-[4-(Benzimidazol-1-yl)butan-2-ylamino]-2-methoxyphenol
—— (5E)-3-ethyl-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H10N2O4S2
(5E)-3-ethyl-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-cyclohexyl-5-(3,5-dibromo-2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C16H15Br2NO2S2
(5Z)-3-cyclohexyl-5-(3,5-dibromo-2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— N-cyclohexyl-N-[(2-hydroxyphenyl)methyl]-2-[(Z)-1-thiophen-2-ylethylideneamino]oxyacetamide —— C21H26N2O3S
N-cyclohexyl-N-[(2-hydroxyphenyl)methyl]-2-[(Z)-1-thiophen-2-ylethylideneamino]oxyacetamide
—— N'-[(2-hydroxy-5-methylphenyl)methyl]ethenesulfonohydrazide —— C10H14N2O3S
N'-[(2-hydroxy-5-methylphenyl)methyl]ethenesulfonohydrazide
—— 3-Hexadecyl-5-(4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C32H44N2O2S
3-Hexadecyl-5-(4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— [1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-(pyrimidin-2-ylamino)ethyl]phosphonic acid —— C14H18N3O5P
[1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-(pyrimidin-2-ylamino)ethyl]phosphonic acid
—— 3,5-bis(trifluoromethyl)phenol;4-methyl-2,6-bis(trifluoromethyl)aniline;N-[4-methyl-2,6-bis(trifluoromethyl)phenyl]propanamide;5-methyl-2-nitro-1,3-bis(trifluoromethyl)benzene;4-nitro-3,5-bis(trifluoromethyl)phenol;2-(2-piperazin-1-ylethylsulfanyl)-7-(trifluoromethyl)-1,3-benzoxazole —— C60H46F33N7O8S
3,5-bis(trifluoromethyl)phenol;4-methyl-2,6-bis(trifluoromethyl)aniline;N-[4-methyl-2,6-bis(trifluoromethyl)phenyl]propanamide;5-methyl-2-nitro-1,3-bis(trifluoromethyl)benzene;4-nitro-3,5-bis(trifluoromethyl)phenol;2-(2-piperazin-1-ylethylsulfanyl)-7-(trifluoromethyl)-1,3-benzoxazole
—— 4-Amino-6-(methylamino)benzene-1,3-diol —— C7H10N2O2
4-Amino-6-(methylamino)benzene-1,3-diol
—— 2-(2-Ethylheptyl)phenol —— C15H24O
2-(2-Ethylheptyl)phenol
—— 2-[2-(5-methyl-5-phenyl-2H-1,2-oxazol-3-yl)ethyl]phenol —— C18H19NO2
2-[2-(5-methyl-5-phenyl-2H-1,2-oxazol-3-yl)ethyl]phenol
—— methyl (4Z)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate —— C20H18N2O4
methyl (4Z)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate
—— 2-(2,6-Dimethylmorpholino)-5-[(E)-1-(2-hydroxyphenyl)methylidene]-1,3-thiazol-4(5H)-one —— C16H18N2O3S
2-(2,6-Dimethylmorpholino)-5-[(E)-1-(2-hydroxyphenyl)methylidene]-1,3-thiazol-4(5H)-one
—— 2-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C15H15NO5S2
2-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
—— 2-[3-Chloro-2-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]cyclohexane-1,3,5-trione —— C15H11ClO7
2-[3-Chloro-2-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]cyclohexane-1,3,5-trione
—— 4-[5-Phenyl-3-(2-phenylethyl)pent-3-en-1-ynyl]phenol —— C25H22O
4-[5-Phenyl-3-(2-phenylethyl)pent-3-en-1-ynyl]phenol
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-[2-(2-hydroxyphenyl)ethoxy]oxolane-2,3-dione —— C14H16O7
(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-[2-(2-hydroxyphenyl)ethoxy]oxolane-2,3-dione
—— (5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H10N2O4S2
(5E)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2E)-2-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C20H14N2O4S
(2E)-2-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 5-[[[6-(2-Aminophenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]-2-methoxyphenol —— C21H19N5O2S
5-[[[6-(2-Aminophenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]-2-methoxyphenol
—— (4S)-4-benzyl-3-[(3S)-3-(2,5-dihydro-1,2-oxazol-3-yl)-3-(4-hydroxyphenyl)propanoyl]-1,3-oxazolidin-2-one —— C22H22N2O5
(4S)-4-benzyl-3-[(3S)-3-(2,5-dihydro-1,2-oxazol-3-yl)-3-(4-hydroxyphenyl)propanoyl]-1,3-oxazolidin-2-one