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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
—— 5-[(2,4-Dihydroxy-5-nitrophenyl)methylidene]-1-phenyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H11N3O6S
5-[(2,4-Dihydroxy-5-nitrophenyl)methylidene]-1-phenyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(1,1-dioxothiolan-3-yl)-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C19H17BrN2O6S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(1,1-dioxothiolan-3-yl)-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— 2-[[4-(diethylazaniumyl)-6-oxocyclohexa-2,4-dien-1-ylidene]methylamino]-5-nitrophenolate —— C17H19N3O4
2-[[4-(diethylazaniumyl)-6-oxocyclohexa-2,4-dien-1-ylidene]methylamino]-5-nitrophenolate
—— 3-[7-(4-hydroxy-3-nitrophenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C17H16N2O6S
3-[7-(4-hydroxy-3-nitrophenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-[(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H10N4O7S2
5-[(2-hydroxy-5-nitrophenyl)methylidene]-3-[(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4-[(5-chloro-2-hydroxyanilino)methylidene]-2-methyl-5-(trifluoromethyl)pyrazol-3-one —— C12H9ClF3N3O2
4-[(5-chloro-2-hydroxyanilino)methylidene]-2-methyl-5-(trifluoromethyl)pyrazol-3-one
—— 3-[(7R)-7-(2-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
3-[(7R)-7-(2-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 3-[(7R)-7-(5-bromo-2-hydroxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C17H16BrNO4S
3-[(7R)-7-(5-bromo-2-hydroxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 6-[(2-hydroxy-5-methylanilino)methylidene]-2-methylcyclohexa-2,4-dien-1-one —— C15H15NO2
6-[(2-hydroxy-5-methylanilino)methylidene]-2-methylcyclohexa-2,4-dien-1-one
—— 2,4-dichloro-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H8Cl2N2O4
2,4-dichloro-6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 3-hydroxy-4-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,5-dien-1-one —— C13H10N2O5
3-hydroxy-4-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,5-dien-1-one
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(4-methoxyphenyl)-1,3-diazinane-2,4,6-trione —— C19H15BrN2O6
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(4-methoxyphenyl)-1,3-diazinane-2,4,6-trione
—— 2-phenylpropyl N-[2-(4-hydroxyphenyl)ethyl]carbamate —— C18H21NO3
2-phenylpropyl N-[2-(4-hydroxyphenyl)ethyl]carbamate
—— 2-(1-Chloroethenyl)but-2-enyl carbamimidothioate;3,4,6-trichloro-2-nitrophenol —— C13H13Cl4N3O3S
2-(1-Chloroethenyl)but-2-enyl carbamimidothioate;3,4,6-trichloro-2-nitrophenol
—— 2-[(1S,2S,5S)-5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol —— C16H20O3
2-[(1S,2S,5S)-5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
—— 2-[(5R,7R)-3-[5-chloro-4-(5-chloro-2-hydroxyanilino)-6-oxopyridazin-1-yl]-1-adamantyl]acetic acid —— C22H23Cl2N3O4
2-[(5R,7R)-3-[5-chloro-4-(5-chloro-2-hydroxyanilino)-6-oxopyridazin-1-yl]-1-adamantyl]acetic acid
—— 2-[(5S,7S)-3-[5-chloro-4-(5-chloro-2-hydroxyanilino)-6-oxopyridazin-1-yl]-1-adamantyl]acetic acid —— C22H23Cl2N3O4
2-[(5S,7S)-3-[5-chloro-4-(5-chloro-2-hydroxyanilino)-6-oxopyridazin-1-yl]-1-adamantyl]acetic acid
—— (4aS,8R,8aR)-3,8a-dibromo-8-(5-bromo-2-hydroxy-3-methoxyphenyl)-7-ethenyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H15Br3O4
(4aS,8R,8aR)-3,8a-dibromo-8-(5-bromo-2-hydroxy-3-methoxyphenyl)-7-ethenyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-3,8a-dibromo-7-ethenyl-8-(2-hydroxyphenyl)-5,8-dihydro-4aH-naphthalene-1,4-dione —— C18H14Br2O3
(4aS,8R,8aR)-3,8a-dibromo-7-ethenyl-8-(2-hydroxyphenyl)-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-3,8a-dibromo-7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H13Br2F3O4
(4aS,8R,8aR)-3,8a-dibromo-7-ethenyl-8-[2-hydroxy-5-(trifluoromethoxy)phenyl]-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-3,8a-dibromo-7-ethenyl-8-(4-hydroxyphenyl)-5,8-dihydro-4aH-naphthalene-1,4-dione —— C18H14Br2O3
(4aS,8R,8aR)-3,8a-dibromo-7-ethenyl-8-(4-hydroxyphenyl)-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-2-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C19H16BrClO3
(4aS,8R,8aR)-8a-bromo-8-(2-chloro-4-hydroxyphenyl)-7-ethenyl-2-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (2S,10R)-2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-5,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C26H25N3O7
(2S,10R)-2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-5,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2R,10R)-2-(2-hydroxyphenyl)-6,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C22H19N3O5
(2R,10R)-2-(2-hydroxyphenyl)-6,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2R,10R)-6-bromo-2-(2-hydroxy-3-methoxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C22H18BrN3O6
(2R,10R)-6-bromo-2-(2-hydroxy-3-methoxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2R,10R)-2-[2-hydroxy-5-(trifluoromethoxy)phenyl]-5,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C23H18F3N3O6
(2R,10R)-2-[2-hydroxy-5-(trifluoromethoxy)phenyl]-5,13-dimethyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2S,10R)-6-bromo-2-(3-hydroxy-4-methoxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C22H18BrN3O6
(2S,10R)-6-bromo-2-(3-hydroxy-4-methoxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2S,10R)-6-bromo-2-(4-hydroxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C21H16BrN3O5
(2S,10R)-6-bromo-2-(4-hydroxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2R,10R)-6-bromo-2-(2-hydroxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C21H16BrN3O5
(2R,10R)-6-bromo-2-(2-hydroxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2R,10R)-2-(4-hydroxy-2,6-dimethoxyphenyl)-5-iodo-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C23H20IN3O7
(2R,10R)-2-(4-hydroxy-2,6-dimethoxyphenyl)-5-iodo-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (2R,10R)-6-bromo-2-(2-hydroxy-4,6-dimethoxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone —— C23H20BrN3O7
(2R,10R)-6-bromo-2-(2-hydroxy-4,6-dimethoxyphenyl)-13-methyl-11,13,15-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),5-triene-4,7,12,14-tetrone
—— (1S,10R)-10-(4-hydroxy-2,6-dimethoxyphenyl)-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 —— C20H22N6O7
(1S,10R)-10-(4-hydroxy-2,6-dimethoxyphenyl)-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
—— (1S,10R)-10-(2-hydroxy-3-prop-2-enylphenyl)-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 —— C21H22N6O5
(1S,10R)-10-(2-hydroxy-3-prop-2-enylphenyl)-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)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(2-hydroxy-4-methoxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C19H14Cl4O4
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(2-hydroxy-4-methoxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxy-3,5-dimethylphenyl)-5,8-dihydronaphthalene-1,4-dione —— C20H16Cl4O3
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxy-3,5-dimethylphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-6-ethenyl-5-(4-hydroxy-2,6-dimethoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C24H28O5
(4aS,5R,8aR)-6-ethenyl-5-(4-hydroxy-2,6-dimethoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxy-3-methylphenyl)-5,8-dihydronaphthalene-1,4-dione —— C19H14Cl4O3
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(4-hydroxy-3-methylphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (1S,10S)-10-(4-hydroxy-3-methylphenyl)-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 —— C19H20N6O5
(1S,10S)-10-(4-hydroxy-3-methylphenyl)-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
—— (1S,10R)-10-(2-chloro-4-hydroxyphenyl)-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 —— C18H17ClN6O5
(1S,10R)-10-(2-chloro-4-hydroxyphenyl)-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
—— (4aR,8R,8aS)-7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O5
(4aR,8R,8aS)-7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-8-(5-bromo-2-hydroxy-3-methoxyphenyl)-7-ethenyl-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21BrO4
(4aR,8R,8aS)-8-(5-bromo-2-hydroxy-3-methoxyphenyl)-7-ethenyl-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O5
(4aR,8R,8aS)-7-ethenyl-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(4-hydroxy-2-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19BrO4
(4aS,8R,8aR)-8a-bromo-7-ethenyl-8-(4-hydroxy-2-methoxyphenyl)-3-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(3-fluoro-2-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C18H11Cl4FO3
(4aS,5R,8aR)-2,3,4a,8a-tetrachloro-6-ethenyl-5-(3-fluoro-2-hydroxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(3-fluoro-4-hydroxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C20H19FO3
(4aR,8R,8aS)-7-ethenyl-8-(3-fluoro-4-hydroxyphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O4
(4aR,8R,8aS)-7-ethenyl-8-(2-hydroxy-5-methoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4aS,5R,8aR)-6-ethenyl-5-(2-hydroxy-3-prop-2-enylphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C25H28O3
(4aS,5R,8aR)-6-ethenyl-5-(2-hydroxy-3-prop-2-enylphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— (4aR,8R,8aS)-7-ethenyl-8-(3-hydroxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O3
(4aR,8R,8aS)-7-ethenyl-8-(3-hydroxyphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— (4S)-4-[(4-hydroxy-2-methoxyphenyl)-[(4R)-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl]methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C28H26N4O4
(4S)-4-[(4-hydroxy-2-methoxyphenyl)-[(4R)-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl]methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— 5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione —— C13H12N2O5
5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione