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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
—— Ethane;phenol;propane —— C26H40O3
Ethane;phenol;propane
—— 2-(3,4,5-Trihydroxyphenyl)ethanesulfinic acid —— C8H10O5S
2-(3,4,5-Trihydroxyphenyl)ethanesulfinic acid
—— 4-Methoxy-2-propan-2-yl-3-thiophen-3-ylphenol —— C14H16O2S
4-Methoxy-2-propan-2-yl-3-thiophen-3-ylphenol
—— 4-[(4E)-7-(2,4-dihydroxy-3-methylphenyl)-4-[6-(2-ethylhexyl)-2-methoxy-8-methylidene-5H-benzo[7]annulen-9-ylidene]-6-methyl-1,5-dihydro-1,3-diazepin-2-ylidene]-3-hydroxy-2-methylcyclohexa-2,5-dien-1-one —— C41H48N2O5
4-[(4E)-7-(2,4-dihydroxy-3-methylphenyl)-4-[6-(2-ethylhexyl)-2-methoxy-8-methylidene-5H-benzo[7]annulen-9-ylidene]-6-methyl-1,5-dihydro-1,3-diazepin-2-ylidene]-3-hydroxy-2-methylcyclohexa-2,5-dien-1-one
—— 4-[2-[4-(Furan-2-yl)-2-methylbut-2-enyl]-4,5,5a,8-tetrahydro-1-benzothiepin-6-yl]phenol —— C25H26O2S
4-[2-[4-(Furan-2-yl)-2-methylbut-2-enyl]-4,5,5a,8-tetrahydro-1-benzothiepin-6-yl]phenol
—— Ethane;2-(ethylideneamino)phenol —— C10H15NO
Ethane;2-(ethylideneamino)phenol
—— (4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylphenyl)-1,3-oxazol-5-one —— C18H15NO4
(4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylphenyl)-1,3-oxazol-5-one
—— 2-Heptadec-1-enyl-6-methoxybenzene-1,4-diol —— C24H40O3
2-Heptadec-1-enyl-6-methoxybenzene-1,4-diol
—— 3-[4-[2-(4-Propan-2-ylpiperidin-1-yl)ethyl]-1,4-oxazin-2-yl]phenol —— C20H28N2O2
3-[4-[2-(4-Propan-2-ylpiperidin-1-yl)ethyl]-1,4-oxazin-2-yl]phenol
—— (6S)-1,2,6,7,8-pentahydroxy-1,8-bis(3,4,5-trihydroxyphenyl)octane-3,4,5-trione —— C20H20O14
(6S)-1,2,6,7,8-pentahydroxy-1,8-bis(3,4,5-trihydroxyphenyl)octane-3,4,5-trione
—— 4-(1-Diethoxyphosphoryl-2-pyridin-3-yliminoethyl)-2-methoxy-6-methylphenol —— C19H25N2O5P
4-(1-Diethoxyphosphoryl-2-pyridin-3-yliminoethyl)-2-methoxy-6-methylphenol
—— 3-Chloro-2-[hydroxy(pyridin-3-yl)methyl]phenol —— C12H10ClNO2
3-Chloro-2-[hydroxy(pyridin-3-yl)methyl]phenol
—— methyl (4Z)-1-allyl-4-(3-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C17H17NO4
methyl (4Z)-1-allyl-4-(3-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
—— 3-bromo-5-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H15BrN4O2
3-bromo-5-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— N-(3,4-Dichloro-phenyl)-2-(4-hydroxy-2-{[1-(4-hydroxy-3-methoxy-phenyl)-methylidene]-hydrazono}-2,5-dihydro-thiazol-5-yl)-acetamide —— C19H16Cl2N4O4S
N-(3,4-Dichloro-phenyl)-2-(4-hydroxy-2-{[1-(4-hydroxy-3-methoxy-phenyl)-methylidene]-hydrazono}-2,5-dihydro-thiazol-5-yl)-acetamide
—— 2-(1,3-benzothiazol-2-ylsulfanyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H15N3O3S2
2-(1,3-benzothiazol-2-ylsulfanyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (2-methoxypyridin-4-yl)methyl 7-[(3,5-difluoro-4-hydroxyphenyl)methyl]-9-methyl-6,8-dioxo-1H-pyrimido[6,1-c][1,4]thiazine-3-carboxylate —— C23H19F2N3O6S
(2-methoxypyridin-4-yl)methyl 7-[(3,5-difluoro-4-hydroxyphenyl)methyl]-9-methyl-6,8-dioxo-1H-pyrimido[6,1-c][1,4]thiazine-3-carboxylate
—— N-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-carboxamide —— C10H9N5O2
N-[(Z)-(3-hydroxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-carboxamide
—— N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-4-carboxamide —— C14H12BrN3O3
N-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-4-carboxamide
—— (5E)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H9NO2S2
(5E)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-(2-hydroxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one —— C16H19N3O3S
(5Z)-5-(2-hydroxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one
—— 2-(2-Butyl-4-hydroxyphenyl)acetic acid —— C12H16O3
2-(2-Butyl-4-hydroxyphenyl)acetic acid
—— 2-methoxy-4-[2-[(5-methyl-1H-imidazol-2-yl)amino]-1-(1-methyl-2-oxo-1,2lambda5-azaphosphinan-2-yl)ethyl]phenol —— C18H27N4O3P
2-methoxy-4-[2-[(5-methyl-1H-imidazol-2-yl)amino]-1-(1-methyl-2-oxo-1,2lambda5-azaphosphinan-2-yl)ethyl]phenol
—— (5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-propyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H15NO3S2
(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-propyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[2-[2-(4-Hydroxyphenyl)ethynylsulfonyl]ethyl]phenol —— C16H14O4S
4-[2-[2-(4-Hydroxyphenyl)ethynylsulfonyl]ethyl]phenol
—— 1-cyclohexyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea —— C15H21N3O2S
1-cyclohexyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea
—— 5-[(3-Bromo-2-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H13BrN2O4S
5-[(3-Bromo-2-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-[2-[2-(4-Hydroxy-3-methoxyphenyl)ethylamino]propoxy]-3,5-dimethylphenol —— C20H27NO4
4-[2-[2-(4-Hydroxy-3-methoxyphenyl)ethylamino]propoxy]-3,5-dimethylphenol
—— Hydroxy-[[[hydroxy(oxo)phosphaniumyl]-[2-(4-hydroxyphenyl)ethyl]amino]methyl]-oxophosphanium —— C9H13NO5P2+2
Hydroxy-[[[hydroxy(oxo)phosphaniumyl]-[2-(4-hydroxyphenyl)ethyl]amino]methyl]-oxophosphanium
—— (E)-2-(1,3-benzothiazol-2-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C17H12N2O2S
(E)-2-(1,3-benzothiazol-2-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 4-(3-Chloro-4-hydroxyphenyl)-6-(4-chlorophenyl)-2-methyl-3,4-dihydropyridine-3,5-dicarbonitrile —— C20H13Cl2N3O
4-(3-Chloro-4-hydroxyphenyl)-6-(4-chlorophenyl)-2-methyl-3,4-dihydropyridine-3,5-dicarbonitrile
—— 4-[1-(Pyridin-2-yldiazenyl)ethyl]benzene-1,3-diol —— C13H13N3O2
4-[1-(Pyridin-2-yldiazenyl)ethyl]benzene-1,3-diol
—— 3-[4-[(2,5-dihydroxy-3,6-dimethyl-4-methylidenecyclohexa-2,5-dien-1-ylidene)methyl]phenyl]-N-propan-2-ylpropanamide —— C22H27NO3
3-[4-[(2,5-dihydroxy-3,6-dimethyl-4-methylidenecyclohexa-2,5-dien-1-ylidene)methyl]phenyl]-N-propan-2-ylpropanamide
—— Ethane;phenol;propane —— C15H32O
Ethane;phenol;propane
—— Ethane;4-[3-(4-hydroperoxyphenyl)butan-2-yloxy]phenol —— C20H30O4
Ethane;4-[3-(4-hydroperoxyphenyl)butan-2-yloxy]phenol
—— 2-Methoxy-5-[[(7-methyl-6-phenylthieno[3,2-d]pyrimidin-4-yl)diazenyl]methyl]phenol —— C21H18N4O2S
2-Methoxy-5-[[(7-methyl-6-phenylthieno[3,2-d]pyrimidin-4-yl)diazenyl]methyl]phenol
—— [1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-(pyrimidin-5-ylamino)ethyl]phosphonic acid —— C14H18N3O5P
[1-(4-Hydroxy-3-methoxy-5-methylphenyl)-2-(pyrimidin-5-ylamino)ethyl]phosphonic acid
—— 2-[2,2-Bis(2,2-dimethylpropoxy)ethylperoxymethyl]phenol —— C19H32O5
2-[2,2-Bis(2,2-dimethylpropoxy)ethylperoxymethyl]phenol
—— (5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione —— C14H14BrNO5S
(5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyethyl)-1,3-thiazolidine-2,4-dione
—— Benzene-1,3-diol;ethane;propane;1,4-xylene —— C22H38O2
Benzene-1,3-diol;ethane;propane;1,4-xylene
—— 2,6-Ditert-butyl-4-[[dimethyl-(4-methylphenyl)silyl]methoxy]phenol —— C24H36O2Si
2,6-Ditert-butyl-4-[[dimethyl-(4-methylphenyl)silyl]methoxy]phenol
—— N-[N'-[ethylamino-(4-hydroxyphenyl)methyl]carbamimidoyl]-2-methylpropanamide —— C14H22N4O2
N-[N'-[ethylamino-(4-hydroxyphenyl)methyl]carbamimidoyl]-2-methylpropanamide
—— (5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-propyl-2-thioxo-1,3-thiazolidin-4-one —— C14H14BrNO3S2
(5E)-5-(2-bromo-4-hydroxy-5-methoxybenzylidene)-3-propyl-2-thioxo-1,3-thiazolidin-4-one
—— 4-[[6-Cycloheptylidene-4-(1-hydroxy-2-methylpropan-2-yl)oxycyclohexa-1,3-dien-1-yl]methyl]phenol —— C24H32O3
4-[[6-Cycloheptylidene-4-(1-hydroxy-2-methylpropan-2-yl)oxycyclohexa-1,3-dien-1-yl]methyl]phenol
—— 2-cyano-N-[(Z)-(3-hydroxyphenyl)methylideneamino]acetamide —— C10H9N3O2
2-cyano-N-[(Z)-(3-hydroxyphenyl)methylideneamino]acetamide
—— 1-(3,5-Dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-2-one —— C13H16Cl2O4
1-(3,5-Dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-2-one
—— 5-[2-(5-Chloro-2,4-dihydroxyphenyl)ethyl]-4-[4-[6-(hydroxyamino)-6-oxohexoxy]phenyl]-1,2-oxazole-3-carboxamide —— C24H26ClN3O7
5-[2-(5-Chloro-2,4-dihydroxyphenyl)ethyl]-4-[4-[6-(hydroxyamino)-6-oxohexoxy]phenyl]-1,2-oxazole-3-carboxamide
—— 2-(3-fluoro-4-hydroxyphenyl)-N-[2-(2-fluoro-4-methylanilino)-1,5-dimethyl-6-oxopyridin-3-yl]cyclopropane-1-sulfinamide —— C23H23F2N3O3S
2-(3-fluoro-4-hydroxyphenyl)-N-[2-(2-fluoro-4-methylanilino)-1,5-dimethyl-6-oxopyridin-3-yl]cyclopropane-1-sulfinamide
—— (4R,8R)-16-chloro-19-hydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(19),9,11,15,17-pentaene-2,13-dione —— C18H17ClO5
(4R,8R)-16-chloro-19-hydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(19),9,11,15,17-pentaene-2,13-dione
—— methyl (4Z)-4-(4-hydroxybenzylidene)-2-methyl-1-(2-methylpropyl)-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate —— C18H21NO4
methyl (4Z)-4-(4-hydroxybenzylidene)-2-methyl-1-(2-methylpropyl)-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate