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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
—— 4-[(5-Ethyl-2-methoxyphenyl)methoxy]phenol —— C16H18O3
4-[(5-Ethyl-2-methoxyphenyl)methoxy]phenol
—— 3-[2-(4-Ethoxyphenyl)ethoxy]aniline —— C16H19NO2
3-[2-(4-Ethoxyphenyl)ethoxy]aniline
—— 4-[3-(4-Ethylphenyl)propoxy]phenol —— C17H20O2
4-[3-(4-Ethylphenyl)propoxy]phenol
—— 4-[2-(4-Fluorophenoxy)ethoxy]phenol —— C14H13FO3
4-[2-(4-Fluorophenoxy)ethoxy]phenol
—— ethyl (4S,5S,6R)-4-hydroxy-6-(2-hydroxy-5-nitrophenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C14H14F3N3O6S
ethyl (4S,5S,6R)-4-hydroxy-6-(2-hydroxy-5-nitrophenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 2-[(2E,5S)-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate —— C18H14N3O4S-
2-[(2E,5S)-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate
—— (5Z)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5Z)-2-[(2S,6S)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— propan-2-yl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19ClN2O5
propan-2-yl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 3-[(1R)-1-[(3S)-3-aminopiperidin-1-yl]ethyl]phenol —— C13H20N2O
3-[(1R)-1-[(3S)-3-aminopiperidin-1-yl]ethyl]phenol
—— (7R)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide —— C21H22N6O4
(7R)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide
—— (7S)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C22H23N5O4
(7S)-N-(2-ethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— 2-[(1S)-1-[(3S)-3-aminopiperidin-1-yl]ethyl]phenol —— C13H20N2O
2-[(1S)-1-[(3S)-3-aminopiperidin-1-yl]ethyl]phenol
—— 4-[(1S)-1-(1,3-thiazol-2-ylmethylamino)ethyl]phenol —— C12H14N2OS
4-[(1S)-1-(1,3-thiazol-2-ylmethylamino)ethyl]phenol
—— 2-[(1S)-1-(1,3-thiazol-2-ylmethylamino)ethyl]phenol —— C12H14N2OS
2-[(1S)-1-(1,3-thiazol-2-ylmethylamino)ethyl]phenol
—— (5E)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5E)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (2R)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methoxyphenoxy)propanamide —— C18H20N2O5
(2R)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methoxyphenoxy)propanamide
—— 4-(2-bromo-4-methylphenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]butanamide —— C19H21BrN2O4
4-(2-bromo-4-methylphenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]butanamide
—— (7S)-7-(3-hydroxy-4-methoxyphenyl)-5-methyl-N-(4-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H21N5O3
(7S)-7-(3-hydroxy-4-methoxyphenyl)-5-methyl-N-(4-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (7R)-7-(3-hydroxy-4-methoxyphenyl)-5-methyl-N-(4-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide —— C21H21N5O3
(7R)-7-(3-hydroxy-4-methoxyphenyl)-5-methyl-N-(4-methylphenyl)-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide
—— (4R)-N-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C19H18ClN3O4
(4R)-N-(4-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— ethyl (7S)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(4-chlorophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C22H20BrClN4O4
ethyl (7S)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(4-chlorophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— ethyl (7R)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(4-chlorophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C22H20BrClN4O4
ethyl (7R)-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-(4-chlorophenyl)-5-methyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— [(1R,3R)-3-methylcyclohexyl] (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H26N2O5
[(1R,3R)-3-methylcyclohexyl] (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl 2-[[(4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanyl]acetate —— C17H18N2O5S
ethyl 2-[[(4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyridin-6-yl]sulfanyl]acetate
—— (2S)-2-hydroxy-4-(4-hydroxyphenyl)-2-methylbutanoic acid —— C11H14O4
(2S)-2-hydroxy-4-(4-hydroxyphenyl)-2-methylbutanoic acid
—— (2S)-2-bromo-N-[2-(4-hydroxyphenyl)ethyl]-3-methylbutanamide —— C13H18BrNO2
(2S)-2-bromo-N-[2-(4-hydroxyphenyl)ethyl]-3-methylbutanamide
—— (2R)-2-bromo-N-[2-(4-hydroxyphenyl)ethyl]-3-methylbutanamide —— C13H18BrNO2
(2R)-2-bromo-N-[2-(4-hydroxyphenyl)ethyl]-3-methylbutanamide
—— (2R)-2-hydroxy-2-(3-hydroxyphenyl)propanoic acid —— C9H10O4
(2R)-2-hydroxy-2-(3-hydroxyphenyl)propanoic acid
—— 3-[(S)-(3-bromo-4-hydroxy-5-methoxyphenyl)-(4-hydroxy-2-methyl-6-oxo-1H-pyridin-3-yl)methyl]-4-hydroxy-6-methyl-1H-pyridin-2-one —— C20H19BrN2O6
3-[(S)-(3-bromo-4-hydroxy-5-methoxyphenyl)-(4-hydroxy-2-methyl-6-oxo-1H-pyridin-3-yl)methyl]-4-hydroxy-6-methyl-1H-pyridin-2-one
—— 4-[(1S,2R,5S,6R,9S)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C17H22O2
4-[(1S,2R,5S,6R,9S)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— (5E)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H20N2O4S
(5E)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5E)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5E)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(2-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (2E)-3-(5-bromo-2-hydroxy-3-methoxyphenyl)-2-methylacrylaldehyde —— C11H11BrO3
(2E)-3-(5-bromo-2-hydroxy-3-methoxyphenyl)-2-methylacrylaldehyde
—— (4R)-4-(3-hydroxyphenyl)-6-methylsulfanyl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile —— C13H12N2O2S
(4R)-4-(3-hydroxyphenyl)-6-methylsulfanyl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile
—— 4-[(1R)-1-(2,2-dimethylpropylamino)ethyl]benzene-1,3-diol —— C13H21NO2
4-[(1R)-1-(2,2-dimethylpropylamino)ethyl]benzene-1,3-diol
—— 2-[[(4R)-5-acetyl-3-cyano-4-(4-hydroxyphenyl)-6-methyl-1,4-dihydropyridin-2-yl]sulfanyl]acetamide —— C17H17N3O3S
2-[[(4R)-5-acetyl-3-cyano-4-(4-hydroxyphenyl)-6-methyl-1,4-dihydropyridin-2-yl]sulfanyl]acetamide
—— 4-[(3S)-3-[[(1R,2S,3R)-2,3-dimethylcyclohexyl]amino]butyl]phenol —— C18H29NO
4-[(3S)-3-[[(1R,2S,3R)-2,3-dimethylcyclohexyl]amino]butyl]phenol
—— 2-[(1R,2S,5R)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C15H18O2
2-[(1R,2S,5R)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— (4R)-6-benzylsulfanyl-4-(4-hydroxyphenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile —— C19H16N2O2S
(4R)-6-benzylsulfanyl-4-(4-hydroxyphenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile
—— ethyl (7S)-7-(3-hydroxy-4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate —— C16H18N4O4
ethyl (7S)-7-(3-hydroxy-4-methoxyphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate
—— 5-[[(1R)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol —— C22H23FN2O2
5-[[(1R)-1-(4-fluorophenyl)-1,3,4,5-tetrahydropyrrolo[1,2-a][1,4]diazepin-2-yl]methyl]-2-methoxyphenol
—— tert-butyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C17H22N2O5
tert-butyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C15H17ClN2O5
ethyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-[(2S,7aS)-1-hydroxy-7a-methyl-4,5,6,7-tetrahydro-2H-benzimidazol-2-yl]phenol —— C14H18N2O2
2-[(2S,7aS)-1-hydroxy-7a-methyl-4,5,6,7-tetrahydro-2H-benzimidazol-2-yl]phenol
—— 2-anilino-4-(1H-pyrrol-3-yl) pyrimidine deriv. 8f —— C18H17N5O
2-anilino-4-(1H-pyrrol-3-yl) pyrimidine deriv. 8f
—— 4-hydroxy-3-methoxy-N'-[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide —— C16H16N2O5
4-hydroxy-3-methoxy-N'-[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzohydrazide
—— 5-Amino-7-(5-bromo-2-hydroxyphenyl)-2-[(5-bromo-2-hydroxyphenyl)methylene]-3-o xo-4,7-dihydro-1,3-thiazolidino[3,2-a]pyridine-6,8-dicarbonitrile —— C22H12Br2N4O3S
5-Amino-7-(5-bromo-2-hydroxyphenyl)-2-[(5-bromo-2-hydroxyphenyl)methylene]-3-o xo-4,7-dihydro-1,3-thiazolidino[3,2-a]pyridine-6,8-dicarbonitrile
—— N-(2-fluorophenyl)-2-[(5Z)-5-(2-hydroxy-5-nitrobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C18H12FN3O6S
N-(2-fluorophenyl)-2-[(5Z)-5-(2-hydroxy-5-nitrobenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 2-[(5Z)-5-(2-hydroxy-3-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methoxyphenyl)acetamide —— C20H18N2O6S
2-[(5Z)-5-(2-hydroxy-3-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]-N-(4-methoxyphenyl)acetamide
—— (5Z)-5-(5-chloro-2-hydroxy-3-iodobenzylidene)-3-(prop-2-en-1-yl)-1,3-thiazolidine-2,4-dione —— C13H9ClINO3S
(5Z)-5-(5-chloro-2-hydroxy-3-iodobenzylidene)-3-(prop-2-en-1-yl)-1,3-thiazolidine-2,4-dione