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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
—— 2-[[(6R)-6-[(dimethylamino)methyl]-1,4-oxazepan-4-yl]methyl]-4-methoxyphenol —— C16H26N2O3
2-[[(6R)-6-[(dimethylamino)methyl]-1,4-oxazepan-4-yl]methyl]-4-methoxyphenol
—— N-[(3S)-1-[(3-fluorophenyl)methyl]-5-oxopyrrolidin-3-yl]-3-hydroxy-4-methoxybenzamide —— C19H19FN2O4
N-[(3S)-1-[(3-fluorophenyl)methyl]-5-oxopyrrolidin-3-yl]-3-hydroxy-4-methoxybenzamide
—— N-[(3R)-1-[(3-fluorophenyl)methyl]-5-oxopyrrolidin-3-yl]-3-hydroxy-4-methoxybenzamide —— C19H19FN2O4
N-[(3R)-1-[(3-fluorophenyl)methyl]-5-oxopyrrolidin-3-yl]-3-hydroxy-4-methoxybenzamide
—— 2-[[(6S)-1,11-dioxa-4,8-diazaspiro[5.6]dodecan-4-yl]methyl]-5-methoxyphenol —— C16H24N2O4
2-[[(6S)-1,11-dioxa-4,8-diazaspiro[5.6]dodecan-4-yl]methyl]-5-methoxyphenol
—— 2-[[(6R)-1,11-dioxa-4,8-diazaspiro[5.6]dodecan-4-yl]methyl]-5-methoxyphenol —— C16H24N2O4
2-[[(6R)-1,11-dioxa-4,8-diazaspiro[5.6]dodecan-4-yl]methyl]-5-methoxyphenol
—— 2-methoxy-4-[(12S)-13,14,16,18-tetrazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2,4,6,14,16-hexaen-12-yl]phenol —— C21H20N4O2
2-methoxy-4-[(12S)-13,14,16,18-tetrazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2,4,6,14,16-hexaen-12-yl]phenol
—— [(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-phenylmethanone —— C20H15N3O4S
[(3S)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-phenylmethanone
—— 2-methoxy-4-[(12R)-13,14,16,18-tetrazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2,4,6,14,16-hexaen-12-yl]phenol —— C21H20N4O2
2-methoxy-4-[(12R)-13,14,16,18-tetrazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2,4,6,14,16-hexaen-12-yl]phenol
—— 2,2,2-trifluoro-1-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone —— C15H11F3N2O2S
2,2,2-trifluoro-1-[(3S)-3-(2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]ethanone
—— N-(4-chloro-2-fluorophenyl)-2-[4-(2-methoxyethyl)phenoxy]acetamide —— C17H17ClFNO3
N-(4-chloro-2-fluorophenyl)-2-[4-(2-methoxyethyl)phenoxy]acetamide
—— 3-(2-Hydroxyphenyl)-1-(4-thiophen-2-ylsulfonylpiperazin-1-yl)propan-1-one —— C17H20N2O4S2
3-(2-Hydroxyphenyl)-1-(4-thiophen-2-ylsulfonylpiperazin-1-yl)propan-1-one
—— 3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-methyl-5-phenylthieno[2,3-d]pyrimidin-4-one —— C21H17N3O3S
3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-methyl-5-phenylthieno[2,3-d]pyrimidin-4-one
—— (5S)-7-(3-hydroxy-4-methoxybenzoyl)-3-methyl-1-oxa-3,7-diazaspiro[4.4]nonan-2-one —— C15H18N2O5
(5S)-7-(3-hydroxy-4-methoxybenzoyl)-3-methyl-1-oxa-3,7-diazaspiro[4.4]nonan-2-one
—— 3-[(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]benzoic acid —— C15H14N2O4
3-[(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]benzoic acid
—— (4R)-4-(3-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C14H15N3O2
(4R)-4-(3-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-4-(3-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C14H15N3O2
(4S)-4-(3-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C14H15N3O2
(4R)-4-(4-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 5-[(Z)-[(2-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H13ClN2O2
5-[(Z)-[(2-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 2-methoxy-4-[(7R)-5-phenyl-2-(trifluoromethyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]phenol —— C19H15F3N4O2
2-methoxy-4-[(7R)-5-phenyl-2-(trifluoromethyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]phenol
—— (4S)-4-(4-hydroxy-3-methoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C15H17N3O3
(4S)-4-(4-hydroxy-3-methoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 2-methoxy-4-[(7S)-5-phenyl-2-(trifluoromethyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]phenol —— C19H15F3N4O2
2-methoxy-4-[(7S)-5-phenyl-2-(trifluoromethyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]phenol
—— (4S)-4-(4-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C14H15N3O2
(4S)-4-(4-hydroxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C15H17N3O3
(4R)-4-(4-hydroxy-3-methoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (5Z)-2-(4-chloro-N-methylanilino)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazol-4-one —— C19H17ClN2O4S
(5Z)-2-(4-chloro-N-methylanilino)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-chloro-N-methylanilino)-1,3-thiazol-4-one —— C18H14Cl2N2O3S
(5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-chloro-N-methylanilino)-1,3-thiazol-4-one
—— (Z)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5H)-one —— C18H16N2O3S
(Z)-2-(benzylamino)-5-(3-hydroxy-4-methoxybenzylidene)thiazol-4(5H)-one
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1R)-1-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]urea —— C22H25F3N2O4
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1R)-1-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]urea
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1S)-1-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]urea —— C22H25F3N2O4
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1S)-1-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]urea
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2S)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea —— C22H29N3O3S
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2S)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1R)-1-[3-(trifluoromethyl)phenyl]ethyl]urea —— C21H23F3N2O3
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1R)-1-[3-(trifluoromethyl)phenyl]ethyl]urea
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1S)-1-[3-(trifluoromethyl)phenyl]ethyl]urea —— C21H23F3N2O3
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(1S)-1-[3-(trifluoromethyl)phenyl]ethyl]urea
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2R)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea —— C22H29N3O3S
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2R)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea
—— 2-[4-(2-methoxyethyl)phenoxy]-N-(2-methylphenyl)acetamide —— C18H21NO3
2-[4-(2-methoxyethyl)phenoxy]-N-(2-methylphenyl)acetamide
—— diethyl (2S,4S)-2,4-dicyano-3-(3,5-dibromo-2-hydroxyphenyl)pentanedioate —— C17H16Br2N2O5
diethyl (2S,4S)-2,4-dicyano-3-(3,5-dibromo-2-hydroxyphenyl)pentanedioate
—— 6-ethyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thieno[2,3-d]pyrimidin-4-one —— C16H15N3O3S
6-ethyl-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thieno[2,3-d]pyrimidin-4-one
—— 4-[2-[(2S)-4-benzylmorpholin-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol —— C20H20N2O3S
4-[2-[(2S)-4-benzylmorpholin-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol
—— 4-[2-[(2R)-4-benzylmorpholin-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol —— C20H20N2O3S
4-[2-[(2R)-4-benzylmorpholin-2-yl]-1,3-thiazol-4-yl]benzene-1,2-diol
—— 2,4-dibromo-6-[(5R)-3-(2-methylphenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]phenol —— C15H12Br2N2O2
2,4-dibromo-6-[(5R)-3-(2-methylphenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]phenol
—— 2,4-dibromo-6-[(5S)-3-(2-methylphenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]phenol —— C15H12Br2N2O2
2,4-dibromo-6-[(5S)-3-(2-methylphenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]phenol
—— 2-methoxyethyl (7R)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C15H17N5O4
2-methoxyethyl (7R)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— 2-methoxyethyl (7S)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate —— C15H17N5O4
2-methoxyethyl (7S)-7-(4-hydroxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
—— (4R)-2-hexyl-4-[[(4R)-1-hexyl-3-methyl-5-oxo-4H-pyrazol-4-yl]-(4-hydroxyphenyl)methyl]-5-methyl-4H-pyrazol-3-one —— C27H40N4O3
(4R)-2-hexyl-4-[[(4R)-1-hexyl-3-methyl-5-oxo-4H-pyrazol-4-yl]-(4-hydroxyphenyl)methyl]-5-methyl-4H-pyrazol-3-one
—— (4S)-2-hexyl-4-[[(4R)-1-hexyl-3-methyl-5-oxo-4H-pyrazol-4-yl]-(4-hydroxyphenyl)methyl]-5-methyl-4H-pyrazol-3-one —— C27H40N4O3
(4S)-2-hexyl-4-[[(4R)-1-hexyl-3-methyl-5-oxo-4H-pyrazol-4-yl]-(4-hydroxyphenyl)methyl]-5-methyl-4H-pyrazol-3-one
—— (4S)-2-hexyl-4-[[(4S)-1-hexyl-3-methyl-5-oxo-4H-pyrazol-4-yl]-(4-hydroxyphenyl)methyl]-5-methyl-4H-pyrazol-3-one —— C27H40N4O3
(4S)-2-hexyl-4-[[(4S)-1-hexyl-3-methyl-5-oxo-4H-pyrazol-4-yl]-(4-hydroxyphenyl)methyl]-5-methyl-4H-pyrazol-3-one
—— N-[(2S)-2-cyclopropyl-2-[3-(2-hydroxyphenyl)propanoylamino]ethyl]-3-(2-hydroxyphenyl)propanamide —— C23H28N2O4
N-[(2S)-2-cyclopropyl-2-[3-(2-hydroxyphenyl)propanoylamino]ethyl]-3-(2-hydroxyphenyl)propanamide
—— N-[(2R)-2-cyclopropyl-2-[3-(2-hydroxyphenyl)propanoylamino]ethyl]-3-(2-hydroxyphenyl)propanamide —— C23H28N2O4
N-[(2R)-2-cyclopropyl-2-[3-(2-hydroxyphenyl)propanoylamino]ethyl]-3-(2-hydroxyphenyl)propanamide
—— 5-[(Z)-[(3,4-dichlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H12Cl2N2O2
5-[(Z)-[(3,4-dichlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 2-(4-ethylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C17H19NO4
2-(4-ethylphenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-2-(2-nitrophenyl)acetamide —— C15H14N2O5
N-(3-hydroxy-4-methoxyphenyl)-2-(2-nitrophenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-2-(3-methylphenoxy)acetamide —— C16H17NO4
N-(3-hydroxy-4-methoxyphenyl)-2-(3-methylphenoxy)acetamide