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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
—— N-[(3-hydroxy-5-nitrophenyl)methylideneamino]-1,3,7-trimethyl-2,4-dioxopyrido[2,3-d]pyrimidine-6-carboxamide —— C18H16N6O6
N-[(3-hydroxy-5-nitrophenyl)methylideneamino]-1,3,7-trimethyl-2,4-dioxopyrido[2,3-d]pyrimidine-6-carboxamide
—— (2Z)-2-[(2-hydroxy-5-methoxyphenyl)methylidene]-6,7-dimethyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one —— C19H16N2O3S
(2Z)-2-[(2-hydroxy-5-methoxyphenyl)methylidene]-6,7-dimethyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one
—— 3-[(2-Hydroxy-3-methoxyphenyl)methylideneamino]-1,5-dihydropyrimido[5,4-b]indole-2,4-dione —— C18H14N4O4
3-[(2-Hydroxy-3-methoxyphenyl)methylideneamino]-1,5-dihydropyrimido[5,4-b]indole-2,4-dione
—— 3-[(2-Hydroxy-3-methoxyphenyl)methylideneamino]-8-methyl-1,5-dihydropyrimido[5,4-b]indole-2,4-dione —— C19H16N4O4
3-[(2-Hydroxy-3-methoxyphenyl)methylideneamino]-8-methyl-1,5-dihydropyrimido[5,4-b]indole-2,4-dione
—— 4-[(2-Hydroxyethyl)sulfonyl]-2,6-dinitrophenol —— C8H8N2O8S
4-[(2-Hydroxyethyl)sulfonyl]-2,6-dinitrophenol
—— tert-butyl (4S,5R)-4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-sulfanylidene-1,3-diazinane-5-carboxylate —— C17H22N2O4S
tert-butyl (4S,5R)-4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-sulfanylidene-1,3-diazinane-5-carboxylate
—— (5Z)-3-benzyl-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H12N2O4S2
(5Z)-3-benzyl-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(4-Bromo-2-hydroxyphenyl)-5,7-dimethyl-1,3-diazatricyclo[3.3.1.1~3,7~]decan-6-one —— C16H19BrN2O2
2-(4-Bromo-2-hydroxyphenyl)-5,7-dimethyl-1,3-diazatricyclo[3.3.1.1~3,7~]decan-6-one
—— (2S)-2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propane-2-sulfonic acid —— C10H14O6S
(2S)-2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propane-2-sulfonic acid
—— 3-(2-hydroxyphenyl)-N-[(1S)-1-pyridin-2-ylethyl]propanamide —— C16H18N2O2
3-(2-hydroxyphenyl)-N-[(1S)-1-pyridin-2-ylethyl]propanamide
—— 3-((E)-((Z)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid —— C19H15ClN2O5S
3-((E)-((Z)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid
—— 4-((E)-((Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-3-ethyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid —— C20H17BrN2O5S
4-((E)-((Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-3-ethyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid
—— ethyl (2Z,5R)-5-[4-(dimethylamino)phenyl]-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H27N3O5S
ethyl (2Z,5R)-5-[4-(dimethylamino)phenyl]-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-<i>p</i>-toluidino-5-vanillylidene-thiazol-4-one —— C18H16N2O3S
2-<i>p</i>-toluidino-5-vanillylidene-thiazol-4-one
—— methyl (2E,7R)-5-amino-6-cyano-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate —— C23H17N3O5S
methyl (2E,7R)-5-amino-6-cyano-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate
—— (4R)-4-(3,5-dibromo-4-hydroxyphenyl)-6-methylsulfanyl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile —— C13H10Br2N2O2S
(4R)-4-(3,5-dibromo-4-hydroxyphenyl)-6-methylsulfanyl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile
—— 1-[(1S)-1-(2-hydroxyphenyl)ethyl]-1,3-dimethylthiourea —— C11H16N2OS
1-[(1S)-1-(2-hydroxyphenyl)ethyl]-1,3-dimethylthiourea
—— 1-[(1R)-1-(2-hydroxyphenyl)ethyl]-1,3-dimethylthiourea —— C11H16N2OS
1-[(1R)-1-(2-hydroxyphenyl)ethyl]-1,3-dimethylthiourea
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]-5-[(N-methylanilino)methyl]triazole-4-carbohydrazide —— C22H23N9O4
1-(4-amino-1,2,5-oxadiazol-3-yl)-N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]-5-[(N-methylanilino)methyl]triazole-4-carbohydrazide
—— (1Z)-4-hydroxy-1-[(2-hydroxy-5-nitrophenyl)methylidene]-6-methylfuro[3,4-c]pyridin-3-one —— C15H10N2O6
(1Z)-4-hydroxy-1-[(2-hydroxy-5-nitrophenyl)methylidene]-6-methylfuro[3,4-c]pyridin-3-one
—— ethyl (2Z,5S)-2-[(4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O4S2
ethyl (2Z,5S)-2-[(4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H11NO3S2
(5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H14BrN3O4S
(5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— (2E,5E)-2-[(3,4-dimethylphenyl)imino]-5-(2-hydroxy-3-methoxybenzylidene)-3-methyl-1,3-thiazolidin-4-one —— C20H20N2O3S
(2E,5E)-2-[(3,4-dimethylphenyl)imino]-5-(2-hydroxy-3-methoxybenzylidene)-3-methyl-1,3-thiazolidin-4-one
—— 3-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(3,4-dihydroxyphenyl)methylideneamino]-5-methyltriazole-4-carboxamide —— C13H12N8O4
3-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(3,4-dihydroxyphenyl)methylideneamino]-5-methyltriazole-4-carboxamide
—— ethyl (2E,5S)-5-(2-ethoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H32N2O7S
ethyl (2E,5S)-5-(2-ethoxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-(4-Hydroxy-3-methoxybenzylidene)-3-isobutyl-2-[(4-methoxyphenyl)imino]-1,3-thiazolidin-4-one —— C22H24N2O4S
5-(4-Hydroxy-3-methoxybenzylidene)-3-isobutyl-2-[(4-methoxyphenyl)imino]-1,3-thiazolidin-4-one
—— (5E)-2-(4-ethoxyphenyl)imino-3-ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C21H22N2O4S
(5E)-2-(4-ethoxyphenyl)imino-3-ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— ethyl (2Z,5S)-2-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17BrCl2N2O4S
ethyl (2Z,5S)-2-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-(2-Bromo-4-hydroxy-5-methoxybenzylidene)-3-(2,4-dichlorobenzyl)-1,3-thiazolidine-2,4-dione —— C18H12BrCl2NO4S
5-(2-Bromo-4-hydroxy-5-methoxybenzylidene)-3-(2,4-dichlorobenzyl)-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazolidine-2,4-dione —— C17H18N2O6S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazolidine-2,4-dione
—— (5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H11BrFNO3S
(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 2-[(4-Ethoxyphenyl)imino]-3-ethyl-5-{4-hydroxy-3-nitrobenzylidene}-1,3-thiazolidin-4-one —— C20H19N3O5S
2-[(4-Ethoxyphenyl)imino]-3-ethyl-5-{4-hydroxy-3-nitrobenzylidene}-1,3-thiazolidin-4-one
—— (5E)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H10Br2FNO3S
(5E)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 5-(5-Bromo-3-chloro-2-hydroxybenzylidene)-3-(4-chlorobenzyl)-1,3-thiazolidine-2,4-dione —— C17H10BrCl2NO3S
5-(5-Bromo-3-chloro-2-hydroxybenzylidene)-3-(4-chlorobenzyl)-1,3-thiazolidine-2,4-dione
—— (5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H11ClFNO3S
(5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— ethyl (2Z,5S)-2-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-5-(4-fluorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17BrFN3O6S
ethyl (2Z,5S)-2-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-5-(4-fluorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— [(4S)-4-(4-hydroxyphenyl)-2-methylpentan-2-yl] carbamate —— C13H19NO3
[(4S)-4-(4-hydroxyphenyl)-2-methylpentan-2-yl] carbamate
—— ethyl (2E,5R)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2E,5R)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18FN3O6S
ethyl (2E,5S)-5-(4-fluorophenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21ClN2O5S
ethyl (2E,5R)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(1,3-dimethylpyrazol-4-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H22N4O4S
ethyl (2E,5R)-2-[(1,3-dimethylpyrazol-4-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21ClN2O5S
ethyl (2E,5S)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2,3,4-trihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C26H24N2O4S
(5E)-3-(3,4-dimethylphenyl)-2-(3,4-dimethylphenyl)imino-5-[(2,3,4-trihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-2-[(4-chlorophenyl)imino]-3-methyl-1,3-thiazolidin-4-one —— C18H14BrClN2O3S
5-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-2-[(4-chlorophenyl)imino]-3-methyl-1,3-thiazolidin-4-one
—— (3Z)-3-(2-hydroxy-3-methoxybenzylidene)-5,6-dimethoxy-1,3-dihydro-2H-indol-2-one —— C18H17NO5
(3Z)-3-(2-hydroxy-3-methoxybenzylidene)-5,6-dimethoxy-1,3-dihydro-2H-indol-2-one
—— (5E)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-(4-ethylphenyl)-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one —— C26H22Br2N2O2S
(5E)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-(4-ethylphenyl)-2-(4-ethylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-methylphenyl)-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C26H24N2O4S
(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-3-(2-methylphenyl)-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— 3-[(1R)-1-(cyclobutylamino)ethyl]phenol —— C12H17NO
3-[(1R)-1-(cyclobutylamino)ethyl]phenol
—— (5E)-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C26H24N2O2S
(5E)-3-(2-ethylphenyl)-2-(2-ethylphenyl)imino-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one