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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
—— (2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methylphenyl)propanamide —— C18H18N2O3
(2R)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(3-methylphenyl)propanamide
—— (5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5E)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (2S)-2-but-3-enoxy-N-[(2-hydroxyphenyl)methyl]-N-methylpropanamide —— C15H21NO3
(2S)-2-but-3-enoxy-N-[(2-hydroxyphenyl)methyl]-N-methylpropanamide
—— (2R)-2-but-3-enoxy-N-[(2-hydroxyphenyl)methyl]-N-methylpropanamide —— C15H21NO3
(2R)-2-but-3-enoxy-N-[(2-hydroxyphenyl)methyl]-N-methylpropanamide
—— 3-hydroxy-N-methyl-N-[(4-methyl-1,3-thiazol-5-yl)methyl]-4-nitrobenzamide —— C13H13N3O4S
3-hydroxy-N-methyl-N-[(4-methyl-1,3-thiazol-5-yl)methyl]-4-nitrobenzamide
—— N-[(5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-ethyl-4-oxo-1,3-thiazolidin-2-ylidene]thiophene-2-sulfonamide —— C16H14N2O5S3
N-[(5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-3-ethyl-4-oxo-1,3-thiazolidin-2-ylidene]thiophene-2-sulfonamide
—— (2R)-2-ethoxy-N-[(3-hydroxyphenyl)methyl]-N-methylpropanamide —— C13H19NO3
(2R)-2-ethoxy-N-[(3-hydroxyphenyl)methyl]-N-methylpropanamide
—— ethyl (5R)-5-(4-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate —— C19H21N3O5S
ethyl (5R)-5-(4-hydroxy-3-methoxyphenyl)-3-oxo-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-diene-11-carboxylate
—— (5R)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H24N3O3S+
(5R)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6-diaza-11-azoniatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5S)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H23N3O3S
(5S)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (5R)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one —— C23H23N3O3S
(5R)-11-benzyl-5-(4-hydroxy-3-methoxyphenyl)-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-3-one
—— (3S)-6-tert-butyl-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide —— C20H21N3O6
(3S)-6-tert-butyl-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
—— (3R)-6-tert-butyl-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide —— C20H21N3O6
(3R)-6-tert-butyl-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
—— 2-(5-Bromo-2-hydroxyphenyl)-5-ethyl-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C17H23BrN2O2+2
2-(5-Bromo-2-hydroxyphenyl)-5-ethyl-7-methyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— (4R)-1-(3-chloro-4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H15ClFNO5
(4R)-1-(3-chloro-4-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-1-(3-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16FNO5
(4S)-1-(3-fluorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H19NO6
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-1-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H16ClNO5
(4S)-1-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(4-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18FNO6
(4R)-1-(4-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H17NO5
(4R)-4-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18ClNO6
(4R)-1-(4-chlorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H19NO6
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C20H17NO5
(4S)-4-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— (4S)-1-(3-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione —— C21H18FNO6
(4S)-1-(3-fluorophenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-4,7-dihydro-3H-furo[3,4-b]pyridine-2,5-dione
—— 1-[(3R)-1-ethylpiperidin-3-yl]-3-[2-(3-hydroxyphenyl)ethyl]urea —— C16H25N3O2
1-[(3R)-1-ethylpiperidin-3-yl]-3-[2-(3-hydroxyphenyl)ethyl]urea
—— 1-[(3S)-1-ethylpiperidin-3-yl]-3-[2-(3-hydroxyphenyl)ethyl]urea —— C16H25N3O2
1-[(3S)-1-ethylpiperidin-3-yl]-3-[2-(3-hydroxyphenyl)ethyl]urea
—— (3S)-N-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-pyrrolidin-1-ylpyrrolidine-1-carboxamide —— C18H27N3O4
(3S)-N-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-pyrrolidin-1-ylpyrrolidine-1-carboxamide
—— (3R)-N-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-pyrrolidin-1-ylpyrrolidine-1-carboxamide —— C18H27N3O4
(3R)-N-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-pyrrolidin-1-ylpyrrolidine-1-carboxamide
—— (2-Hydroxy-3-methoxyphenyl)methyl-(2-morpholin-4-ium-4-ylethyl)azanium —— C14H24N2O3+2
(2-Hydroxy-3-methoxyphenyl)methyl-(2-morpholin-4-ium-4-ylethyl)azanium
—— (8S,9R)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C26H29N5O6
(8S,9R)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— 1-[(3S)-5-(3-hydroxyphenyl)-3-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O2S
1-[(3S)-5-(3-hydroxyphenyl)-3-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-5-oxo-6,7-dihydro-4H-[1,2]thiazolo[4,5-b]pyridine-3-carboxylic acid —— C15H14N2O6S
(7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-5-oxo-6,7-dihydro-4H-[1,2]thiazolo[4,5-b]pyridine-3-carboxylic acid
—— (8R,9S)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C24H24ClN5O3
(8R,9S)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (8R,9R)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C24H24ClN5O3
(8R,9R)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— 1-[(3S)-5-(furan-2-yl)-3-(3-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O3
1-[(3S)-5-(furan-2-yl)-3-(3-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— (8S,9S)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C24H24ClN5O3
(8S,9S)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— methyl (7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C15H16N4O4
methyl (7S)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— (8R,9R)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C26H29N5O6
(8R,9R)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-5-oxo-6,7-dihydro-4H-[1,2]thiazolo[4,5-b]pyridine-3-carboxylic acid —— C15H14N2O6S
(7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-5-oxo-6,7-dihydro-4H-[1,2]thiazolo[4,5-b]pyridine-3-carboxylic acid
—— (8R,9S)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C26H29N5O6
(8R,9S)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— 1-[(3R)-5-(3-hydroxyphenyl)-3-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O2S
1-[(3R)-5-(3-hydroxyphenyl)-3-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— methyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C15H16N4O4
methyl (7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— (8S,9R)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C24H24ClN5O3
(8S,9R)-4-tert-butyl-10-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— 1-[(3R)-5-(furan-2-yl)-3-(3-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone —— C15H14N2O3
1-[(3R)-5-(furan-2-yl)-3-(3-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— (8S,9S)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C26H29N5O6
(8S,9S)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-(3-methoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (7R)-7-(3,4-dihydroxy-2,5-dimethoxyphenyl)-2-(methylamino)-6,7-dihydro-4H-[1,3]thiazolo[4,5-b]pyridin-5-one —— C15H17N3O5S
(7R)-7-(3,4-dihydroxy-2,5-dimethoxyphenyl)-2-(methylamino)-6,7-dihydro-4H-[1,3]thiazolo[4,5-b]pyridin-5-one
—— (4R)-4-(3-hydroxy-4-methoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C15H17N3O3
(4R)-4-(3-hydroxy-4-methoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (8S,9S)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-phenyl-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C25H27N5O5
(8S,9S)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-phenyl-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (7S)-7-(3,4-dihydroxy-2,5-dimethoxyphenyl)-2-(methylamino)-6,7-dihydro-4H-[1,3]thiazolo[4,5-b]pyridin-5-one —— C15H17N3O5S
(7S)-7-(3,4-dihydroxy-2,5-dimethoxyphenyl)-2-(methylamino)-6,7-dihydro-4H-[1,3]thiazolo[4,5-b]pyridin-5-one
—— (8S,9R)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-phenyl-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C25H27N5O5
(8S,9R)-4-tert-butyl-8-(3,4-dihydroxy-2,5-dimethoxyphenyl)-10-phenyl-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one