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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
—— (1R,9S,13E,16S)-16-acetyl-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one —— C22H17N3O6S
(1R,9S,13E,16S)-16-acetyl-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one
—— methyl (1S,9R,13E,16R)-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-14-oxo-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraene-16-carboxylate —— C22H17N3O7S
methyl (1S,9R,13E,16R)-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-14-oxo-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraene-16-carboxylate
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]acetamide —— C13H14N4O3
N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-[(4R)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]acetamide
—— (1R,9S,13E,16R)-16-acetyl-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one —— C22H17N3O6S
(1R,9S,13E,16R)-16-acetyl-13-[(2-hydroxy-5-nitrophenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one
—— N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]acetamide —— C13H14N4O3
N-[(E)-(3-hydroxyphenyl)methylideneamino]-2-[(4S)-3-methyl-5-oxo-1,4-dihydropyrazol-4-yl]acetamide
—— (1R,9S,13E,16R)-16-acetyl-13-[(2-hydroxy-3-methoxyphenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one —— C23H20N2O5S
(1R,9S,13E,16R)-16-acetyl-13-[(2-hydroxy-3-methoxyphenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one
—— (4E)-4-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(4-fluorophenyl)pyrazolidine-3,5-dione —— C17H11Br2FN2O4
(4E)-4-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(4-fluorophenyl)pyrazolidine-3,5-dione
—— 1-(2-Ethylphenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea —— C16H17N3O3S
1-(2-Ethylphenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea
—— (5E)-3-(3-chlorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C16H9ClN2O5S
(5E)-3-(3-chlorophenyl)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— (4E)-1-(3-chloro-4-methylphenyl)-4-[(2,4-dihydroxyphenyl)methylidene]pyrazolidine-3,5-dione —— C17H13ClN2O4
(4E)-1-(3-chloro-4-methylphenyl)-4-[(2,4-dihydroxyphenyl)methylidene]pyrazolidine-3,5-dione
—— (4E)-4-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(3-chloro-4-methylphenyl)pyrazolidine-3,5-dione —— C18H14BrClN2O4
(4E)-4-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(3-chloro-4-methylphenyl)pyrazolidine-3,5-dione
—— (4E)-1-(3-chloro-4-methylphenyl)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C18H15ClN2O4
(4E)-1-(3-chloro-4-methylphenyl)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— (4E)-1-(3-chloro-4-methylphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione —— C18H15ClN2O4
(4E)-1-(3-chloro-4-methylphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]pyrazolidine-3,5-dione
—— ethyl (2E,5S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26BrN3O5S
ethyl (2E,5S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26BrN3O5S
ethyl (2E,5R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-[4-(dimethylamino)phenyl]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (E)-5-(1,3-benzothiazol-2-yl)-6-(3-hydroxy-4-methoxyphenyl)hex-5-enoic acid —— C20H19NO4S
(E)-5-(1,3-benzothiazol-2-yl)-6-(3-hydroxy-4-methoxyphenyl)hex-5-enoic acid
—— (5Z)-2-anilino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-oxofuran-3-carboxylic acid —— C20H17NO5
(5Z)-2-anilino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-4-oxofuran-3-carboxylic acid
—— 2-methoxy-4-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
2-methoxy-4-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 2-methoxy-4-[[[(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
2-methoxy-4-[[[(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 2-methoxy-5-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
2-methoxy-5-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 4-[2-cyclopropylimino-3-[(Z)-(3-methylthiophen-2-yl)methylideneamino]-1,3-thiazol-4-yl]benzene-1,3-diol —— C18H17N3O2S2
4-[2-cyclopropylimino-3-[(Z)-(3-methylthiophen-2-yl)methylideneamino]-1,3-thiazol-4-yl]benzene-1,3-diol
—— 2-methoxy-5-[[[(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
2-methoxy-5-[[[(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 2-methoxy-6-[[[(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
2-methoxy-6-[[[(1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 4-methoxy-2-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
4-methoxy-2-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 2-methoxy-6-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol —— C17H26N2O2
2-methoxy-6-[[[(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]methylamino]methyl]phenol
—— 1-(3,5-Dichlorophenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea —— C14H11Cl2N3O3S
1-(3,5-Dichlorophenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea
—— (2E,6Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-(thiophen-2-ylmethylidene)cyclohexan-1-one —— C19H17BrO3S
(2E,6Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-(thiophen-2-ylmethylidene)cyclohexan-1-one
—— (3S)-N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-1,1-dioxothiolane-3-carboxamide —— C13H15BrN2O5S
(3S)-N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-1,1-dioxothiolane-3-carboxamide
—— 3-[(E)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile —— C15H12BrN3O3
3-[(E)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile
—— (2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H21NO3S
(2Z,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— (2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H21NO3S
(2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-[(2R)-5-chloro-2,3-dihydro-1,3-benzothiazol-2-yl]-2,6-dimethoxyphenol —— C15H14ClNO3S
4-[(2R)-5-chloro-2,3-dihydro-1,3-benzothiazol-2-yl]-2,6-dimethoxyphenol
—— 4-[(2S)-5-chloro-2,3-dihydro-1,3-benzothiazol-2-yl]-2,6-dimethoxyphenol —— C15H14ClNO3S
4-[(2S)-5-chloro-2,3-dihydro-1,3-benzothiazol-2-yl]-2,6-dimethoxyphenol
—— (5E)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,4-dichloroanilino)-1,3-thiazol-4-one —— C17H11BrCl2N2O3S
(5E)-5-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,4-dichloroanilino)-1,3-thiazol-4-one
—— methyl (1R,2S,3R,7E,10R)-7-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C24H20N2O6S
methyl (1R,2S,3R,7E,10R)-7-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
—— (3Z)-3-[1-(2-hydroxy-5-methylanilino)ethylidene]-6-methylpyran-2,4-dione —— C15H15NO4
(3Z)-3-[1-(2-hydroxy-5-methylanilino)ethylidene]-6-methylpyran-2,4-dione
—— (3Z)-1-(1,3-benzodioxol-5-yl)-3-[(4-hydroxy-3-methoxyphenyl)methylidene]pyrrolidine-2,5-dione —— C19H15NO6
(3Z)-1-(1,3-benzodioxol-5-yl)-3-[(4-hydroxy-3-methoxyphenyl)methylidene]pyrrolidine-2,5-dione
—— (3Z)-1-cyclohexyl-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]pyrrolidine-2,5-dione —— C18H21NO5
(3Z)-1-cyclohexyl-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]pyrrolidine-2,5-dione
—— 3-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C15H15NO6S2
3-[(5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— 4-[(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C14H12BrNO4S2
4-[(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
—— 5-[(5E)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C15H15NO4S2
5-[(5E)-5-[(3-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
—— (5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C17H13ClN2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— (1R,2R,4S)-N-[(4-hydroxyphenyl)methyl]-N-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide —— C16H19NO2
(1R,2R,4S)-N-[(4-hydroxyphenyl)methyl]-N-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide
—— (E)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile —— C17H17BrN4O2
(E)-3-(2-bromo-5-hydroxy-4-methoxyphenyl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile
—— 4-[(E)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one —— C16H17BrN2O3
4-[(E)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one
—— 4-[(E)-2-(4-hydroxy-3,5-dimethylphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one —— C17H20N2O2
4-[(E)-2-(4-hydroxy-3,5-dimethylphenyl)ethenyl]-2-propan-2-yl-1H-pyrimidin-6-one
—— (3S)-1-[2-(4-hydroxyphenyl)ethyl]-3-methylpyrrolidine-2,5-dione —— C13H15NO3
(3S)-1-[2-(4-hydroxyphenyl)ethyl]-3-methylpyrrolidine-2,5-dione
—— (1R,2R,4S)-N-[2-(4-hydroxyphenyl)ethyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide —— C16H19NO2
(1R,2R,4S)-N-[2-(4-hydroxyphenyl)ethyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide
—— (1R,2S,4S)-N-[(3-hydroxyphenyl)methyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide —— C15H17NO2
(1R,2S,4S)-N-[(3-hydroxyphenyl)methyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide