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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
—— (4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-3-prop-2-enylphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C24H26O3
(4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-3-prop-2-enylphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (1S,10S)-10-(4-hydroxy-3-methoxyphenyl)-4,13-dimethyl-2,4,6,11,13,15-hexazatetracyclo[7.7.0.02,6.011,15]hexadec-8-ene-3,5,12,14-tetrone —— C19H20N6O6
(1S,10S)-10-(4-hydroxy-3-methoxyphenyl)-4,13-dimethyl-2,4,6,11,13,15-hexazatetracyclo[7.7.0.02,6.011,15]hexadec-8-ene-3,5,12,14-tetrone
—— (4aS,5R,8aR)-6-ethenyl-5-(3-hydroxy-4-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H26O4
(4aS,5R,8aR)-6-ethenyl-5-(3-hydroxy-4-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-6-ethenyl-5-(2-hydroxy-6-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H26O4
(4aS,5R,8aR)-6-ethenyl-5-(2-hydroxy-6-methoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O4
(4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(4-hydroxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O3
(4aR,8R,8aS)-7-ethenyl-8-(4-hydroxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(2-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C18H12Cl4O3
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(2-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C18H12Cl4O3
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(2-hydroxy-3-methylphenyl)-5,8-dihydronaphthalene-1,4-dione —— C19H14Cl4O3
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(2-hydroxy-3-methylphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5S,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5,8-dihydronaphthalene-1,4-dione —— C21H16Cl4O4
(4aS,5S,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-5,8-dihydronaphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(3-hydroxy-4-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
(4aR,8R,8aS)-7-ethenyl-8-(3-hydroxy-4-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxy-2-methoxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C19H14Cl4O4
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxy-2-methoxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-6-ethenyl-5-(3-fluoro-2-hydroxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C22H23FO3
(4aS,5R,8aR)-6-ethenyl-5-(3-fluoro-2-hydroxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-8-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H18BrClO4
(4aS,8R,8aR)-8a-bromo-8-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(4-hydroxy-3,5-dimethylphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O3
(4aR,8R,8aS)-7-ethenyl-8-(4-hydroxy-3,5-dimethylphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(4-hydroxy-2,6-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21BrO5
(4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(4-hydroxy-2,6-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(4-hydroxy-3-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19BrO4
(4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(4-hydroxy-3-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8S,8aS)-7-ethenyl-8-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C24H26O4
(4aR,8S,8aS)-7-ethenyl-8-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(3-fluoro-2-hydroxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19FO3
(4aR,8R,8aS)-7-ethenyl-8-(3-fluoro-2-hydroxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21BrO5
(4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-6-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O4
(4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-6-methoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(3-hydroxy-4-methoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
(4aR,8R,8aS)-7-ethenyl-8-(3-hydroxy-4-methoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C23H26O5
(4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-4,6-dimethoxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19ClO3
(4aR,8R,8aS)-8-(5-chloro-2-hydroxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(2-hydroxy-4-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19BrO4
(4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(2-hydroxy-4-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H19F3O4
(4aR,8R,8aS)-7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H18Br2O4
(4aS,8R,8aR)-8a-bromo-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-7-ethenyl-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-Chloro-2-[2-ethyl-6-(4-ethylphenyl)-2-methyl-2,3,4,5-tetrahydropyrimidin-4-yl]phenol —— C21H25ClN2O
4-Chloro-2-[2-ethyl-6-(4-ethylphenyl)-2-methyl-2,3,4,5-tetrahydropyrimidin-4-yl]phenol
—— 6-Methoxybenzene-1,2,3,4,5-pentol —— C7H8O6
6-Methoxybenzene-1,2,3,4,5-pentol
—— 3-[(1R)-1-(1,3-thiazol-2-ylmethylamino)ethyl]phenol —— C12H14N2OS
3-[(1R)-1-(1,3-thiazol-2-ylmethylamino)ethyl]phenol
—— 4-(methylsulfonimidoyl)phenol —— C7H9NO2S
4-(methylsulfonimidoyl)phenol
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(4-ethoxyphenyl)-2-(3-nitrophenyl)-1,1-dioxo-1,3-thiazolidin-4-one —— C25H21BrN2O8S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(4-ethoxyphenyl)-2-(3-nitrophenyl)-1,1-dioxo-1,3-thiazolidin-4-one
—— 5-[(2-Hydroxy-3,5-dinitrophenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C14H10N4O7S
5-[(2-Hydroxy-3,5-dinitrophenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-amino-N-[(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboxamide —— C10H9N5O3
4-amino-N-[(3-hydroxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboxamide
—— 2-Chloro-6-(5-hydroxypent-1-ynyl)benzene-1,4-diol —— C11H11ClO3
2-Chloro-6-(5-hydroxypent-1-ynyl)benzene-1,4-diol
—— 3-[[(5-Phenyl-1,2,4-triazin-3-yl)hydrazinylidene]methyl]phenol —— C16H13N5O
3-[[(5-Phenyl-1,2,4-triazin-3-yl)hydrazinylidene]methyl]phenol
—— 5-[(5-Bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H7BrN2O4S2
5-[(5-Bromo-2-hydroxy-3-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2-hydroxy-5-nitrophenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C16H15N3O4S
2-(2-hydroxy-5-nitrophenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— 5-[(2-Hydroxy-3-prop-2-enylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H11NO2S2
5-[(2-Hydroxy-3-prop-2-enylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (3Z)-3-[7-(3-hydroxy-4-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
(3Z)-3-[7-(3-hydroxy-4-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— Lopac-E-4375 —— C13H19NO9
Lopac-E-4375
—— 4-fluoro-2-[(1S)-1-[[(2R)-1-hydroxypropan-2-yl]amino]ethyl]phenol —— C11H16FNO2
4-fluoro-2-[(1S)-1-[[(2R)-1-hydroxypropan-2-yl]amino]ethyl]phenol
—— 4-fluoro-2-[(1S)-1-[[(2R)-2-hydroxypropyl]amino]ethyl]phenol —— C11H16FNO2
4-fluoro-2-[(1S)-1-[[(2R)-2-hydroxypropyl]amino]ethyl]phenol
—— 2-[(1S)-1-(butylamino)ethyl]-4-fluorophenol —— C12H18FNO
2-[(1S)-1-(butylamino)ethyl]-4-fluorophenol
—— 4-fluoro-2-[(1R)-1-(propan-2-ylamino)ethyl]phenol —— C11H16FNO
4-fluoro-2-[(1R)-1-(propan-2-ylamino)ethyl]phenol
—— 2-[(1R)-1-(cyclopropylamino)ethyl]-4-fluorophenol —— C11H14FNO
2-[(1R)-1-(cyclopropylamino)ethyl]-4-fluorophenol
—— 2-[(1R)-1-(cyclopropylmethylamino)ethyl]-4-fluorophenol —— C12H16FNO
2-[(1R)-1-(cyclopropylmethylamino)ethyl]-4-fluorophenol
—— 2-[(1S)-1-[[(2R)-butan-2-yl]amino]ethyl]-4-fluorophenol —— C12H18FNO
2-[(1S)-1-[[(2R)-butan-2-yl]amino]ethyl]-4-fluorophenol
—— 2-[(1S)-1-(cyclopropylmethylamino)ethyl]-4-fluorophenol —— C12H16FNO
2-[(1S)-1-(cyclopropylmethylamino)ethyl]-4-fluorophenol
—— 4-fluoro-2-[(1R)-1-(2-hydroxyethylamino)ethyl]phenol —— C10H14FNO2
4-fluoro-2-[(1R)-1-(2-hydroxyethylamino)ethyl]phenol