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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
—— 26,27,28-Trihydroxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaen-25-olate —— C28H23O4-
26,27,28-Trihydroxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaen-25-olate
—— cyclohexyl (7R)-2-benzylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C26H27N5O5S
cyclohexyl (7R)-2-benzylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— cyclohexyl (7S)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C27H29FN4O4S
cyclohexyl (7S)-2-[(2-fluorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— cyclohexyl (7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C20H24N4O4
cyclohexyl (7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— N-(3,4-dimethylphenyl)-N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide —— C20H23N3O4
N-(3,4-dimethylphenyl)-N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide
—— cyclohexyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C20H24N4O4
cyclohexyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— propyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C23H22ClN5O5S
propyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— prop-2-enyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C24H23ClN4O4S
prop-2-enyl (7R)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— N-(2,4-dichlorophenyl)-N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide —— C18H17Cl2N3O4
N-(2,4-dichlorophenyl)-N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]butanediamide
—— prop-2-enyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C24H23ClN4O4S
prop-2-enyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— butyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C25H27ClN4O4S
butyl (7S)-2-[(2-chlorophenyl)methylsulfanyl]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— (7S)-N-(2-ethoxyphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H24N6O5S
(7S)-N-(2-ethoxyphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H24N6O4S
(7S)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide —— C20H19N7O5
(7S)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-N-(2-ethoxyphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C23H24N6O5S
(7R)-N-(2-ethoxyphenyl)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C24H26N6O4S
(7R)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-2-butylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C24H26N6O4S
(7R)-2-butylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C22H22N6O4S
(7S)-2-ethylsulfanyl-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C24H26N6O4S
(7S)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-2-propylsulfanyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide —— C20H19N7O4
(7S)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H20N6O4
(7S)-N-(2,3-dimethylphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C20H18N6O4
(7R)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-N-(3-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H20N6O5
(7R)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-nitrophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 1-[(2-hydroxyphenyl)methyl]-3-[(2S)-2-methyl-3-pyrazol-1-ylpropyl]-1-[[(2R)-oxolan-2-yl]methyl]urea —— C20H28N4O3
1-[(2-hydroxyphenyl)methyl]-3-[(2S)-2-methyl-3-pyrazol-1-ylpropyl]-1-[[(2R)-oxolan-2-yl]methyl]urea
—— 1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2R)-2-methyl-3-pyrazol-1-ylpropyl]urea —— C16H22N4O2
1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(2R)-2-methyl-3-pyrazol-1-ylpropyl]urea
—— 1-[(2-hydroxyphenyl)methyl]-3-[(2S)-2-methyl-3-pyrazol-1-ylpropyl]-1-[[(2S)-oxolan-2-yl]methyl]urea —— C20H28N4O3
1-[(2-hydroxyphenyl)methyl]-3-[(2S)-2-methyl-3-pyrazol-1-ylpropyl]-1-[[(2S)-oxolan-2-yl]methyl]urea
—— 1-benzyl-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-[[(2R)-oxolan-2-yl]methyl]urea —— C23H30N2O3
1-benzyl-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-[[(2R)-oxolan-2-yl]methyl]urea
—— 2-methoxyethyl 2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23N3O8S
2-methoxyethyl 2-[(4-hydroxy-3-nitrophenyl)methylidene]-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-benzyl-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-[[(2S)-oxolan-2-yl]methyl]urea —— C23H30N2O3
1-benzyl-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-1-[[(2S)-oxolan-2-yl]methyl]urea
—— (m-Hydroxyphenyl)trimethylphosphonium —— C9H14OP
(m-Hydroxyphenyl)trimethylphosphonium
—— [amino(oxoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;cobalt(2+);pyridine —— C14H17CoN4O3+3
[amino(oxoniumylidene)methyl]-[(Z)-(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;cobalt(2+);pyridine
—— 3-(2-Fluorophenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one —— C17H13FN2O3S
3-(2-Fluorophenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
—— 4-(2-hydroxy-5-nitrophenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C18H16N4O4S
4-(2-hydroxy-5-nitrophenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 4-[[5-[(R)-amino(cyclopropyl)methyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C13H15N3O2
4-[[5-[(R)-amino(cyclopropyl)methyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— 4-[[5-[(S)-amino(cyclopropyl)methyl]-1,2,4-oxadiazol-3-yl]methyl]phenol —— C13H15N3O2
4-[[5-[(S)-amino(cyclopropyl)methyl]-1,2,4-oxadiazol-3-yl]methyl]phenol
—— 6-hydroxy-7-[(6-hydroxy-8-oxo-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-7-yl)-(4-hydroxyphenyl)methyl]-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-8-one —— C21H24N4O5S2
6-hydroxy-7-[(6-hydroxy-8-oxo-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-7-yl)-(4-hydroxyphenyl)methyl]-3,4,9,9a-tetrahydro-2H-pyrimido[2,1-b][1,3]thiazin-8-one
—— 8a-bromo-7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21BrO5
8a-bromo-7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— N-[2-(3,4-dimethoxyphenyl)ethyl]-2-[4-(2-methoxyethyl)phenoxy]acetamide —— C21H27NO5
N-[2-(3,4-dimethoxyphenyl)ethyl]-2-[4-(2-methoxyethyl)phenoxy]acetamide
—— 4-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]benzene-1,3-diol —— C11H18N2O2
4-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]benzene-1,3-diol
—— 5-[(4-Chlorophenyl)sulfanylmethyl]-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylpyrazol-3-one —— C24H19ClN2O3S
5-[(4-Chlorophenyl)sulfanylmethyl]-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-phenylpyrazol-3-one
—— 4-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]phenol —— C11H18N2O
4-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]phenol
—— 2-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]phenol —— C11H18N2O
2-[(1S)-1-[2-aminoethyl(methyl)amino]ethyl]phenol
—— 3,4,5-trihydroxy-N-[(4-methylcyclohexylidene)amino]benzamide —— C14H18N2O4
3,4,5-trihydroxy-N-[(4-methylcyclohexylidene)amino]benzamide
—— 4-(2-Hydroxy-3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile —— C15H12N4O3
4-(2-Hydroxy-3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile
—— N-[(1S)-1-(4-hydroxyphenyl)ethyl]-N-methylpent-4-enamide —— C14H19NO2
N-[(1S)-1-(4-hydroxyphenyl)ethyl]-N-methylpent-4-enamide
—— N-[(1R)-1-(4-hydroxyphenyl)ethyl]-N-methylpent-4-enamide —— C14H19NO2
N-[(1R)-1-(4-hydroxyphenyl)ethyl]-N-methylpent-4-enamide
—— 4-[(1R)-1-[2-aminoethyl(methyl)amino]ethyl]phenol —— C11H18N2O
4-[(1R)-1-[2-aminoethyl(methyl)amino]ethyl]phenol
—— 1-(2-Hydroxy-5-nitro-phenyl)-3-<pyridyl-(2)>-propen-(2)-on-(1) 92060-75-8 C14H10N2O4
1-(2-Hydroxy-5-nitro-phenyl)-3-<pyridyl-(2)>-propen-(2)-on-(1)
—— 5-[(5-Chloro-2-hydroxyphenyl)methylidene]-2-(4-chlorophenyl)imino-1,3-thiazolidin-4-one —— C16H10Cl2N2O2S
5-[(5-Chloro-2-hydroxyphenyl)methylidene]-2-(4-chlorophenyl)imino-1,3-thiazolidin-4-one
—— N'-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-N-(4-methylphenyl)butanediamide —— C19H21N3O4
N'-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-N-(4-methylphenyl)butanediamide