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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
—— (5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO2S2
(5E)-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (3E)-3-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-chloro-1H-indol-2-one —— C16H11BrClNO3
(3E)-3-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-chloro-1H-indol-2-one
—— 2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-phenyl-3H-thieno[2,3-d]pyrimidin-4-one —— C21H15ClN2O3S
2-[(Z)-1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-phenyl-3H-thieno[2,3-d]pyrimidin-4-one
—— N-[(1R)-5-fluoro-2,3-dihydro-1H-inden-1-yl]-2-hydroxy-4-nitrobenzamide —— C16H13FN2O4
N-[(1R)-5-fluoro-2,3-dihydro-1H-inden-1-yl]-2-hydroxy-4-nitrobenzamide
—— (2Z,5Z)-2-[2-(furan-2-yl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H13NO5S
(2Z,5Z)-2-[2-(furan-2-yl)-2-oxoethylidene]-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-[(2Z)-2-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-5-chloro-1H-pyridazin-6-one —— C12H10BrClN4O3
4-[(2Z)-2-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-5-chloro-1H-pyridazin-6-one
—— 3-benzylsulfanyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione —— C17H16N4O2S2
3-benzylsulfanyl-4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-1,2,4-triazole-5-thione
—— 5-[(Z)-[ethyl-(4-methylphenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C17H20N2O2
5-[(Z)-[ethyl-(4-methylphenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-(4-fluorophenyl)thiourea —— C15H13BrFN3O2S
1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-(4-fluorophenyl)thiourea
—— 4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(2R)-oxolan-2-yl]-1H-1,2,4-triazole-5-thione —— C14H16N4O3S
4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(2R)-oxolan-2-yl]-1H-1,2,4-triazole-5-thione
—— 1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-butylthiourea —— C13H18BrN3O2S
1-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-butylthiourea
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyanilino)acetamide —— C17H18BrN3O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-methoxyanilino)acetamide
—— (E)-3-(1,3-benzoxazol-2-yl)-4-(2-bromo-5-hydroxy-4-methoxyphenyl)but-3-enoate —— C18H13BrNO5-
(E)-3-(1,3-benzoxazol-2-yl)-4-(2-bromo-5-hydroxy-4-methoxyphenyl)but-3-enoate
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methoxyanilino)acetamide —— C17H19N3O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(3-methoxyanilino)acetamide
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-pentylthiourea —— C14H21N3O2S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-pentylthiourea
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-oxoazepan-1-yl)acetamide —— C16H20BrN3O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-oxoazepan-1-yl)acetamide
—— 4-[2-(4-Ethoxyanilino)-1,3-thiazol-4-yl]benzene-1,3-diol —— C17H16N2O3S
4-[2-(4-Ethoxyanilino)-1,3-thiazol-4-yl]benzene-1,3-diol
—— (5Z)-2-(2,5-dimethylphenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(2,5-dimethylphenyl)imino-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-[2-(3,5-Dimethylanilino)-1,3-thiazol-4-yl]benzene-1,3-diol —— C17H16N2O2S
4-[2-(3,5-Dimethylanilino)-1,3-thiazol-4-yl]benzene-1,3-diol
—— (2E)-1-(4-hydroxy-3-methoxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one —— C15H14O3S
(2E)-1-(4-hydroxy-3-methoxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
—— (E)-5-(4-hydroxy-3-methoxybenzylidene)-2-(4-(2-hydroxyethyl)piperazin-1-yl)thiazol-4(5H)-one —— C17H21N3O4S
(E)-5-(4-hydroxy-3-methoxybenzylidene)-2-(4-(2-hydroxyethyl)piperazin-1-yl)thiazol-4(5H)-one
—— (4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxyphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C24H21N5O2
(4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxyphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H21N3O4
(4R)-4-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4S)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxyphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C24H21N5O2
(4S)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxyphenyl)-3-phenyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C18H18N2O3
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— (4S,6S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3,6-dimethyl-4,8-dihydro-2H-pyrazolo[3,4-e][1,4]thiazepin-7-one —— C16H19N3O4S
(4S,6S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3,6-dimethyl-4,8-dihydro-2H-pyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S,6R)-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-4,8-dihydro-2H-pyrazolo[3,4-e][1,4]thiazepin-7-one —— C15H17N3O3S
(4S,6R)-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-4,8-dihydro-2H-pyrazolo[3,4-e][1,4]thiazepin-7-one
—— [(3R)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-phenylmethanone —— C20H15N3O4S
[(3R)-3-(2-hydroxy-5-nitrophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-phenylmethanone
—— 2,2,2-trifluoro-1-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone —— C17H13F3N2O2
2,2,2-trifluoro-1-[(3R)-3-(2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
—— 5-[(Z)-[[2,6-dinitro-4-(trifluoromethyl)phenyl]hydrazinylidene]methyl]-2-methoxyphenol —— C15H11F3N4O6
5-[(Z)-[[2,6-dinitro-4-(trifluoromethyl)phenyl]hydrazinylidene]methyl]-2-methoxyphenol
—— (5Z)-2-(4-chloro-N-methylanilino)-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C17H13ClN2O3S
(5Z)-2-(4-chloro-N-methylanilino)-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-5-[(2-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-chloro-N-methylanilino)-1,3-thiazol-4-one —— C18H14Cl2N2O3S
(5Z)-5-[(2-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-chloro-N-methylanilino)-1,3-thiazol-4-one
—— diethyl (2R,4R)-2,4-dicyano-3-(3,5-dibromo-2-hydroxyphenyl)pentanedioate —— C17H16Br2N2O5
diethyl (2R,4R)-2,4-dicyano-3-(3,5-dibromo-2-hydroxyphenyl)pentanedioate
—— N-(3-hydroxy-4-methoxyphenyl)-3-phenylpropanamide —— C16H17NO3
N-(3-hydroxy-4-methoxyphenyl)-3-phenylpropanamide
—— 2-(2-fluorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide —— C15H14FNO4
2-(2-fluorophenoxy)-N-(3-hydroxy-4-methoxyphenyl)acetamide
—— N-(3-hydroxy-4-methoxyphenyl)-2-phenylsulfanylacetamide —— C15H15NO3S
N-(3-hydroxy-4-methoxyphenyl)-2-phenylsulfanylacetamide
—— (5E)-2-[4-(1-ethyl-3-methylpyrazol-4-yl)sulfonylpiperazin-1-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C20H23N5O4S2
(5E)-2-[4-(1-ethyl-3-methylpyrazol-4-yl)sulfonylpiperazin-1-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (1S,10R,13R)-13-aminotricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-5-ol —— C13H17NO
(1S,10R,13R)-13-aminotricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-5-ol
—— (5Z,8Z,11E,14Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide —— C28H41NO3
(5Z,8Z,11E,14Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide
—— 4-[(3,5-dimethyl-4H-pyrazol-4-yl)methyl]phenol —— C12H14N2O
4-[(3,5-dimethyl-4H-pyrazol-4-yl)methyl]phenol
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(4-methoxyphenyl)thiourea —— C16H17N3O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-(4-methoxyphenyl)thiourea
—— 1-(2,6-dimethylphenyl)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea —— C17H19N3O2S
1-(2,6-dimethylphenyl)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea
—— 4-[(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C14H12ClNO4S2
4-[(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
—— 2-(4-Methoxyphenyl)ethyl 3-(phenoxymethyl)-1-benzofuran-2-carboxylate —— C25H22O5
2-(4-Methoxyphenyl)ethyl 3-(phenoxymethyl)-1-benzofuran-2-carboxylate
—— 2-(4-Methoxyphenyl)ethyl 2-(1,3-benzothiazol-2-ylsulfanyl)acetate —— C18H17NO3S2
2-(4-Methoxyphenyl)ethyl 2-(1,3-benzothiazol-2-ylsulfanyl)acetate
—— ethyl (4R,5R,6R)-4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C16H19F3N2O6S
ethyl (4R,5R,6R)-4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 2-[(2S)-2-ethyl-1,3-thiazolidin-2-yl]phenol —— C11H15NOS
2-[(2S)-2-ethyl-1,3-thiazolidin-2-yl]phenol
—— ethyl (4R,5R,6S)-4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C16H19F3N2O6S
ethyl (4R,5R,6S)-4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— 4-methyl-2,6-bis[(2S)-octadecan-2-yl]phenol —— C43H80O
4-methyl-2,6-bis[(2S)-octadecan-2-yl]phenol
—— 4-methyl-2,6-bis[(2R)-octadecan-2-yl]phenol —— C43H80O
4-methyl-2,6-bis[(2R)-octadecan-2-yl]phenol