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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
—— 5-[(1R)-2-amino-1-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl]-2-methoxyphenol —— C15H24N2O3
5-[(1R)-2-amino-1-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl]-2-methoxyphenol
—— (2E)-1-(4-chlorophenyl)-3-[(2-hydroxy-5-methylphenyl)amino]prop-2-en-1-one —— C16H14ClNO2
(2E)-1-(4-chlorophenyl)-3-[(2-hydroxy-5-methylphenyl)amino]prop-2-en-1-one
—— 4-[(1S)-2-amino-1-(N-methylanilino)ethyl]-2-methoxyphenol —— C16H20N2O2
4-[(1S)-2-amino-1-(N-methylanilino)ethyl]-2-methoxyphenol
—— 4-[(1R)-2-amino-1-(N-ethylanilino)ethyl]benzene-1,3-diol —— C16H20N2O2
4-[(1R)-2-amino-1-(N-ethylanilino)ethyl]benzene-1,3-diol
—— 4-[(1S)-2-amino-1-(4-hydroxy-N-methylanilino)ethyl]benzene-1,3-diol —— C15H18N2O3
4-[(1S)-2-amino-1-(4-hydroxy-N-methylanilino)ethyl]benzene-1,3-diol
—— 4-[(1R)-2-amino-1-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl]-2-methoxyphenol —— C15H24N2O3
4-[(1R)-2-amino-1-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl]-2-methoxyphenol
—— 5-[(1S)-2-amino-1-(N-methylanilino)ethyl]-2-methoxyphenol —— C16H20N2O2
5-[(1S)-2-amino-1-(N-methylanilino)ethyl]-2-methoxyphenol
—— 2-[(1S)-2-amino-1-(N-methylanilino)ethyl]-5-methoxyphenol —— C16H20N2O2
2-[(1S)-2-amino-1-(N-methylanilino)ethyl]-5-methoxyphenol
—— (Z)-3-(3-hydroxy-4-methoxyphenyl)-2-[(7S)-7-methyl-4-oxo-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-2-yl]prop-2-enenitrile —— C21H19N3O3S
(Z)-3-(3-hydroxy-4-methoxyphenyl)-2-[(7S)-7-methyl-4-oxo-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-2-yl]prop-2-enenitrile
—— 4-[(1S)-2-amino-1-morpholin-4-ylethyl]-2-methoxyphenol —— C13H20N2O3
4-[(1S)-2-amino-1-morpholin-4-ylethyl]-2-methoxyphenol
—— 2-[(1S)-2-amino-1-morpholin-4-ylethyl]phenol —— C12H18N2O2
2-[(1S)-2-amino-1-morpholin-4-ylethyl]phenol
—— (5Z)-1-(2-fluorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H10FN3O5S
(5Z)-1-(2-fluorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— (2E)-3-(4-bromo-1-methyl-1H-pyrazol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C14H13BrN2O3
(2E)-3-(4-bromo-1-methyl-1H-pyrazol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— 2-[(1S)-1-piperazin-1-ylethyl]phenol —— C12H18N2O
2-[(1S)-1-piperazin-1-ylethyl]phenol
—— tetrahydroxyketocalix[4]arene —— C44H48O8
tetrahydroxyketocalix[4]arene
—— 3-[(1R)-1-piperazin-1-ylethyl]phenol —— C12H18N2O
3-[(1R)-1-piperazin-1-ylethyl]phenol
—— 1-benzyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea —— C16H17N3O2S
1-benzyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea
—— (5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one —— C17H8BrF3N2O4S2
(5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
—— cyclopenta-1,3-diene;(E)-3-cyclopenta-2,4-dien-1-yl-1-(2-hydroxy-4-methylphenyl)prop-2-en-1-one;iron —— C20H10FeO2-10
cyclopenta-1,3-diene;(E)-3-cyclopenta-2,4-dien-1-yl-1-(2-hydroxy-4-methylphenyl)prop-2-en-1-one;iron
—— (Z)-2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C19H12Cl2N2O2S
(Z)-2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 3-[(Z)-1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enylidene]-6-methylpyran-2,4-dione —— C17H16O7
3-[(Z)-1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enylidene]-6-methylpyran-2,4-dione
—— (1S,6R)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]bicyclo[4.1.0]heptane-7-carboxamide —— C16H20N2O3
(1S,6R)-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]bicyclo[4.1.0]heptane-7-carboxamide
—— (5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H10BrClFNO3S
(5Z)-5-[(3-bromo-5-chloro-4-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— (5Z)-3-benzyl-5-[(E)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H16ClNO2S2
(5Z)-3-benzyl-5-[(E)-3-(5-chloro-2-hydroxyphenyl)-2-methylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 1-(2-Hydroxy-5-nitrophenyl)-3-(2-pyridinyl)-2-propen-1-one —— C14H10N2O4
1-(2-Hydroxy-5-nitrophenyl)-3-(2-pyridinyl)-2-propen-1-one
—— (2E)-2-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-[1,3]thiazolo[3,2-a]benzimidazol-1-one —— C16H8BrN3O4S
(2E)-2-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-[1,3]thiazolo[3,2-a]benzimidazol-1-one
—— (2Z,5Z)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-(nitromethylidene)-1,3-thiazolidin-4-one —— C12H10N2O4S
(2Z,5Z)-5-[(2-hydroxyphenyl)methylidene]-3-methyl-2-(nitromethylidene)-1,3-thiazolidin-4-one
—— methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate —— C21H20N2O5
methyl (4E)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate
—— methyl (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-propylpyrrole-3-carboxylate —— C18H21NO5
methyl (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-propylpyrrole-3-carboxylate
—— 2-nitro-4-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]phenol —— C20H23N3O3
2-nitro-4-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]phenol
—— 4-nitro-3-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]phenol —— C20H23N3O3
4-nitro-3-[[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]phenol
—— (5Z)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-(3,4-dichlorobenzyl)-1,3-thiazolidine-2,4-dione —— C18H12Cl3NO4S
(5Z)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-(3,4-dichlorobenzyl)-1,3-thiazolidine-2,4-dione
—— (2Z,5E)-2-[(3,5-Dimethylphenyl)imino]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(2Z,5E)-2-[(3,5-Dimethylphenyl)imino]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— Pseudopelletierinehydrochloride —— C11H10N2O3S
Pseudopelletierinehydrochloride
—— N-[(Z)-1-[3-(cyclopropanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide —— C19H19N3O5
N-[(Z)-1-[3-(cyclopropanecarbonylamino)phenyl]ethylideneamino]-3,4,5-trihydroxybenzamide
—— (14E)-11-(2-chlorophenyl)-14-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one —— C27H17ClN4O6S
(14E)-11-(2-chlorophenyl)-14-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one
—— (5E)-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C28H28N2O4S
(5E)-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 3,4,5-trihydroxy-N-[(E)-[phenyl(pyridin-3-yl)methylidene]amino]benzamide —— C19H15N3O4
3,4,5-trihydroxy-N-[(E)-[phenyl(pyridin-3-yl)methylidene]amino]benzamide
—— (3Z)-3-[(2-Hydroxy-5-nitrophenyl)methylidene]-2,3-dihydro-1H-indol-2-one —— C15H10N2O4
(3Z)-3-[(2-Hydroxy-5-nitrophenyl)methylidene]-2,3-dihydro-1H-indol-2-one
—— Ethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C25H24N2O6S
Ethyl (2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-[4-(4-nitrophenyl)-1,3-thiazol-2-YL]prop-2-enenitrile —— C19H13N3O4S
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-[4-(4-nitrophenyl)-1,3-thiazol-2-YL]prop-2-enenitrile
—— (E)-3-(5-hydroxy-2-nitrophenyl)-2-(6-methyl-1H-benzimidazol-2-yl)prop-2-enenitrile —— C17H12N4O3
(E)-3-(5-hydroxy-2-nitrophenyl)-2-(6-methyl-1H-benzimidazol-2-yl)prop-2-enenitrile
—— 2-[(5E)-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide —— C20H16Br2N2O5S
2-[(5E)-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methylphenyl)acetamide
—— (5Z)-2-amino-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C10H6Br2N2O2S
(5Z)-2-amino-5-[(3,5-dibromo-2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-(6-methyl-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C23H22N4O4S
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-(6-methyl-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C23H22N4O5S
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-1-methylpyrrolidine-2,3-dione —— C13H13NO4
(4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-1-methylpyrrolidine-2,3-dione
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H18N4O4S
(4S)-4-(4-hydroxy-3-methoxyphenyl)-1-(6-methoxy-1,3-benzothiazol-2-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 2,6-dimethoxy-4-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol —— C19H25NO3S
2,6-dimethoxy-4-[[(2S)-2-thiophen-2-ylazepan-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2S)-2-(5-methylthiophen-2-yl)azepan-1-yl]methyl]phenol —— C19H25NO2S
2-methoxy-6-[[(2S)-2-(5-methylthiophen-2-yl)azepan-1-yl]methyl]phenol