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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;1-(4-hydroxy-3-methylphenyl)-4-methylpentan-2-one —— C15H24O2
Ethane;1-(4-hydroxy-3-methylphenyl)-4-methylpentan-2-one
—— 3-(2,3-Dihydroxyphenyl)propylcarbamic acid —— C10H13NO4
3-(2,3-Dihydroxyphenyl)propylcarbamic acid
—— (4Z)-1-(3,4-dimethylphenyl)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C19H18N2O4
(4Z)-1-(3,4-dimethylphenyl)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 4-(4,5,5-Trichloro-2-hexyl-4-methyl-1,2-thiazolidin-2-ium-2-yl)phenol —— C16H23Cl3NOS+
4-(4,5,5-Trichloro-2-hexyl-4-methyl-1,2-thiazolidin-2-ium-2-yl)phenol
—— 7-(5-Bromo-2-hydroxyphenyl)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-imino-3-oxo-6,7-dihydro-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile —— C22H12Br2N4O3S
7-(5-Bromo-2-hydroxyphenyl)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-imino-3-oxo-6,7-dihydro-[1,3]thiazolo[3,2-a]pyridine-6,8-dicarbonitrile
—— 2-[1-Hydroxy-2-(propylamino)ethyl]phenol —— C11H17NO2
2-[1-Hydroxy-2-(propylamino)ethyl]phenol
—— 2-(2,4-dichlorophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C16H14Cl2N2O4
2-(2,4-dichlorophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— [6-(4-Hydroxy-3,5-dimethylphenyl)-2-[4-(4-hydroxy-3,5-dimethylphenyl)-2-oxobutyl]-2-[3-(4-hydroxy-3,5-dimethylphenyl)propanoyloxymethyl]-4-oxohexyl] 3-(4-hydroxy-3,5-dimethylphenyl)propanoate;dihydrate —— C49H64O12
[6-(4-Hydroxy-3,5-dimethylphenyl)-2-[4-(4-hydroxy-3,5-dimethylphenyl)-2-oxobutyl]-2-[3-(4-hydroxy-3,5-dimethylphenyl)propanoyloxymethyl]-4-oxohexyl] 3-(4-hydroxy-3,5-dimethylphenyl)propanoate;dihydrate
—— (4Z)-4-[[[(4-hydroxy-3-methoxyphenyl)-[[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino]methyl]amino]methylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C24H24N2O6
(4Z)-4-[[[(4-hydroxy-3-methoxyphenyl)-[[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino]methyl]amino]methylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-butyl-2-[(4-hydroxy-3,5-dimethylphenyl)methyl]propanedioate;2-[4-[3-(4-hydroxy-3,5-dimethylphenyl)propylperoxy]-2,2,6,6-tetramethylpiperidin-1-yl]ethyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate —— C69H109N3O11
Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-butyl-2-[(4-hydroxy-3,5-dimethylphenyl)methyl]propanedioate;2-[4-[3-(4-hydroxy-3,5-dimethylphenyl)propylperoxy]-2,2,6,6-tetramethylpiperidin-1-yl]ethyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate
—— Acetamide;ethane;phenol —— C10H17NO2
Acetamide;ethane;phenol
—— 4-[(4,5-Dimethoxy-15-methyl-12,14,15-triazatetracyclo[8.7.0.02,7.013,17]heptadeca-2(7),3,10,12-tetraen-14-yl)methyl]phenol —— C24H29N3O3
4-[(4,5-Dimethoxy-15-methyl-12,14,15-triazatetracyclo[8.7.0.02,7.013,17]heptadeca-2(7),3,10,12-tetraen-14-yl)methyl]phenol
—— ethyl (2Z)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2Z)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 6-(3-chloro-4-hydroxyphenyl)-5-(2-cyclohexyloxyacetyl)-4-ethyl-5,6-dihydro-1H-pyrimidin-2-one —— C20H25ClN2O4
6-(3-chloro-4-hydroxyphenyl)-5-(2-cyclohexyloxyacetyl)-4-ethyl-5,6-dihydro-1H-pyrimidin-2-one
—— 4-[[1-[(4-Hydroxyphenyl)methyl]cyclohexyl]methyl]phenol —— C20H24O2
4-[[1-[(4-Hydroxyphenyl)methyl]cyclohexyl]methyl]phenol
—— (5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C10H7N3O4S
(5E)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (2E,5E)-5-(5-bromo-2-hydroxy-3-nitrobenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C16H10BrN3O4S
(2E,5E)-5-(5-bromo-2-hydroxy-3-nitrobenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (5E)-5-[(3-bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H10BrNO3S2
(5E)-5-[(3-bromo-2-hydroxy-5-methoxyphenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[[[6-(2-Fluoroanilino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]diazenyl]methyl]-2-methoxyphenol —— C18H14FN7O3
4-[[[6-(2-Fluoroanilino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]diazenyl]methyl]-2-methoxyphenol
—— 4-[2-(6-Cyclopentyl-2,3-dihydropyran-6-yl)ethyl]-2-ethyl-6-fluorophenol —— C20H27FO2
4-[2-(6-Cyclopentyl-2,3-dihydropyran-6-yl)ethyl]-2-ethyl-6-fluorophenol
—— (5Z)-2-(2,6-dimethylmorpholin-4-yl)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5Z)-2-(2,6-dimethylmorpholin-4-yl)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— 4-(3-Chloro-4-hydroxyphenyl)-2-methyl-6-thiophen-2-yl-3,4-dihydropyridine-3,5-dicarbonitrile —— C18H12ClN3OS
4-(3-Chloro-4-hydroxyphenyl)-2-methyl-6-thiophen-2-yl-3,4-dihydropyridine-3,5-dicarbonitrile
—— 2-Bromo-3-(4-hydroxyphenyl)-5-methylidene-2,4,6,6a-tetrahydropentalen-1-one —— C15H13BrO2
2-Bromo-3-(4-hydroxyphenyl)-5-methylidene-2,4,6,6a-tetrahydropentalen-1-one
—— 1-dec-1-enyl-4-(diazonioamino)-2,5-dihydroxy-6-methoxy-3-methylbenzene —— C18H28N3O3+
1-dec-1-enyl-4-(diazonioamino)-2,5-dihydroxy-6-methoxy-3-methylbenzene
—— Ethoxyphosphane;phenol —— C8H13O2P
Ethoxyphosphane;phenol
—— 3-[(Z)-N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propyltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate —— C16H18N8O3
3-[(Z)-N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propyltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate
—— Ethane;phenol;propane —— C19H32O2
Ethane;phenol;propane
—— 2-[6-(2-Chloro-6-fluoro-3,4,5-trihydroxyanilino)-2-methyl-3-(trihydroxymethyl)phenyl]-2-hydroxyacetic acid —— C16H15ClFNO9
2-[6-(2-Chloro-6-fluoro-3,4,5-trihydroxyanilino)-2-methyl-3-(trihydroxymethyl)phenyl]-2-hydroxyacetic acid
—— (2E)-6-[(4-fluorophenyl)methyl]-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-[1,3]thiazolo[3,2-b][1,2,4]triazine-3,7-dione —— C20H14FN3O4S
(2E)-6-[(4-fluorophenyl)methyl]-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-[1,3]thiazolo[3,2-b][1,2,4]triazine-3,7-dione
—— 4,4-Dibutoxy-2,2,6,6-tetramethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]piperidine —— C28H47NO5
4,4-Dibutoxy-2,2,6,6-tetramethyl-1-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]piperidine
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione —— C17H13NO4S
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-phenyl-1,3-thiazolidine-2,4-dione
—— 4-(1-Diethoxyphosphoryl-2-pyrazin-2-yliminoethyl)-2,6-dimethylphenol —— C18H24N3O4P
4-(1-Diethoxyphosphoryl-2-pyrazin-2-yliminoethyl)-2,6-dimethylphenol
—— N'-[(E)-(3-bromo-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide —— C14H11BrN2O5
N'-[(E)-(3-bromo-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]-3,4,5-trihydroxybenzohydrazide
—— (2Z,5E)-5-(5-chloro-2-hydroxybenzylidene)-3-cyclohexyl-2-(phenylimino)-1,3-thiazolidin-4-one —— C22H21ClN2O2S
(2Z,5E)-5-(5-chloro-2-hydroxybenzylidene)-3-cyclohexyl-2-(phenylimino)-1,3-thiazolidin-4-one
—— 4-(2-Deuteriooxyethyl)-1,2-dimethoxybenzene —— C10H14O3
4-(2-Deuteriooxyethyl)-1,2-dimethoxybenzene
—— 4-[2-[2-Methyl-5-(3,3,3-trifluoro-2-phenylpropyl)pyrrol-1-yl]ethyl]phenol —— C22H22F3NO
4-[2-[2-Methyl-5-(3,3,3-trifluoro-2-phenylpropyl)pyrrol-1-yl]ethyl]phenol
—— ethyl (2Z)-5-(3-ethoxy-4-methoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O7S
ethyl (2Z)-5-(3-ethoxy-4-methoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-5-[4-(methylsulfanyl)phenyl]-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O6S2
ethyl (2Z)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-5-[4-(methylsulfanyl)phenyl]-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— [5-(3-hydroxy-5-nitrophenyl)-3-oxo-1-(N'-phenylmethoxycarbonylcarbamimidoyl)-2-(propan-2-ylamino)-2H-pyrazin-4-yl] 3-phenylpropanoate —— C31H32N6O8
[5-(3-hydroxy-5-nitrophenyl)-3-oxo-1-(N'-phenylmethoxycarbonylcarbamimidoyl)-2-(propan-2-ylamino)-2H-pyrazin-4-yl] 3-phenylpropanoate
—— ethyl (2Z)-5-(2,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2Z)-5-(2,5-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[4-[Methyl-phenyl-(3-trimethylsilylpentan-3-yloxy)silyl]hexyl]phenol —— C27H44O2Si2
2-[4-[Methyl-phenyl-(3-trimethylsilylpentan-3-yloxy)silyl]hexyl]phenol
—— 2-[(2-chloro-4-hydroxyphenyl)methyl]-N-ethyl-3-(1-phenylethylimino)propanamide —— C20H23ClN2O2
2-[(2-chloro-4-hydroxyphenyl)methyl]-N-ethyl-3-(1-phenylethylimino)propanamide
—— 7-[2-(4-Phenylcyclohexyl)ethyl]-5,6,7,8,9,10-hexahydrobenzo[8]annulene-2,5-diol —— C26H34O2
7-[2-(4-Phenylcyclohexyl)ethyl]-5,6,7,8,9,10-hexahydrobenzo[8]annulene-2,5-diol
—— 2-Bromo-4-methoxyphenol;ethane —— C9H13BrO2
2-Bromo-4-methoxyphenol;ethane
—— Phosphanyl 2-tert-butyl-2-[(4-hydroxyphenyl)methyl]-3,3-dimethylbutanoate —— C17H27O3P
Phosphanyl 2-tert-butyl-2-[(4-hydroxyphenyl)methyl]-3,3-dimethylbutanoate
—— Ethane;2-methyl-1,3-oxazole;phenol —— C14H23NO2
Ethane;2-methyl-1,3-oxazole;phenol
—— ethyl (Z)-3-(benzylamino)-2-(3,4-dichloro-2,5-dihydroxyphenyl)but-2-enoate —— C19H19Cl2NO4
ethyl (Z)-3-(benzylamino)-2-(3,4-dichloro-2,5-dihydroxyphenyl)but-2-enoate
—— 4-Amino-2-methylphenol;ethane —— C9H15NO
4-Amino-2-methylphenol;ethane
—— ethyl (2Z)-5-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23N3O8S
ethyl (2Z)-5-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C10H7N3O4S
(5E)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one