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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-bromo-N-[4-[(1R)-1-[[(2S)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide —— C27H37BrN2O4
2-bromo-N-[4-[(1R)-1-[[(2S)-3-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]phenyl]acetamide
—— (2S,3S)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C24H21NO8
(2S,3S)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2R,3S)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C24H21NO8
(2R,3S)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— [(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]urea —— C9H10BrN3O3
[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]urea
—— (2S,3R)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C24H21NO8
(2S,3R)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2S,3R)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C22H18ClNO6
(2S,3R)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2S,3S)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C22H18ClNO6
(2S,3S)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2R,3S)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C22H18ClNO6
(2R,3S)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2R,3S)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C25H25NO9
(2R,3S)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2S,3R)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C25H25NO9
(2S,3R)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (2R,3R)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C25H25NO9
(2R,3R)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— methyl (3S)-3-(3-hydroxy-4-methoxyphenyl)-3-[3-hydroxy-6-[(4-methoxyphenyl)sulfanylmethyl]-4-oxopyran-2-yl]propanoate —— C24H24O8S
methyl (3S)-3-(3-hydroxy-4-methoxyphenyl)-3-[3-hydroxy-6-[(4-methoxyphenyl)sulfanylmethyl]-4-oxopyran-2-yl]propanoate
—— methyl (3S)-3-[6-[(2,4-difluorophenyl)sulfanylmethyl]-3-hydroxy-4-oxopyran-2-yl]-3-(3-hydroxy-4-methoxyphenyl)propanoate —— C23H20F2O7S
methyl (3S)-3-[6-[(2,4-difluorophenyl)sulfanylmethyl]-3-hydroxy-4-oxopyran-2-yl]-3-(3-hydroxy-4-methoxyphenyl)propanoate
—— methyl (3R)-3-[6-[(4-fluorophenyl)sulfanylmethyl]-3-hydroxy-4-oxopyran-2-yl]-3-(3-hydroxy-4-methoxyphenyl)propanoate —— C23H21FO7S
methyl (3R)-3-[6-[(4-fluorophenyl)sulfanylmethyl]-3-hydroxy-4-oxopyran-2-yl]-3-(3-hydroxy-4-methoxyphenyl)propanoate
—— methyl (3R)-3-[6-[(2,4-difluorophenyl)sulfanylmethyl]-3-hydroxy-4-oxopyran-2-yl]-3-(3-hydroxy-4-methoxyphenyl)propanoate —— C23H20F2O7S
methyl (3R)-3-[6-[(2,4-difluorophenyl)sulfanylmethyl]-3-hydroxy-4-oxopyran-2-yl]-3-(3-hydroxy-4-methoxyphenyl)propanoate
—— methyl (3R)-3-(3-hydroxy-4-methoxyphenyl)-3-[3-hydroxy-6-[(4-methoxyphenyl)sulfanylmethyl]-4-oxopyran-2-yl]propanoate —— C24H24O8S
methyl (3R)-3-(3-hydroxy-4-methoxyphenyl)-3-[3-hydroxy-6-[(4-methoxyphenyl)sulfanylmethyl]-4-oxopyran-2-yl]propanoate
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C16H19N3O4
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (2S,3S)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C25H25NO9
(2S,3S)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-N-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— (4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C16H19N3O4
(4S)-4-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— methyl (2R,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate —— C18H18O8
methyl (2R,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate
—— (2R,3R)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide —— C22H18ClNO6
(2R,3R)-N-(4-chlorophenyl)-3-(3-hydroxy-4-methoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxamide
—— methyl (2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate —— C18H18O8
methyl (2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate
—— methyl (2S,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate —— C18H18O8
methyl (2S,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate
—— methyl (2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate —— C18H18O8
methyl (2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-4-oxo-2,3-dihydrofuro[3,2-c]pyran-2-carboxylate
—— [2-[(2R)-butan-2-yl]-3-hydroxy-4,6-dinitroanilino] 2,5-dichlorobenzoate —— C17H15Cl2N3O7
[2-[(2R)-butan-2-yl]-3-hydroxy-4,6-dinitroanilino] 2,5-dichlorobenzoate
—— 3-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]phenol —— C13H14N4O
3-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]phenol
—— 4-bromo-5-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H15BrN4O2
4-bromo-5-[(Z)-[(4,6-dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— [2-[(2S)-butan-2-yl]-3-hydroxy-4,6-dinitroanilino] 2,5-dichlorobenzoate —— C17H15Cl2N3O7
[2-[(2S)-butan-2-yl]-3-hydroxy-4,6-dinitroanilino] 2,5-dichlorobenzoate
—— 4-[(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]benzoic acid —— C15H14N2O4
4-[(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]benzoic acid
—— 4-[(2Z)-2-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]benzoic acid —— C15H13BrN2O4
4-[(2Z)-2-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]benzoic acid
—— (3E,5E)-3,5-bis[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-(cyclopropylmethyl)piperidin-4-one —— C25H25Cl2NO5
(3E,5E)-3,5-bis[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-1-(cyclopropylmethyl)piperidin-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1-methyl-6,7-dihydroindazol-4-one —— C16H16N2O3
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1-methyl-6,7-dihydroindazol-4-one
—— 4-[(3S)-4,4-difluoro-3-hydroxybutyl]phenol —— C10H12F2O2
4-[(3S)-4,4-difluoro-3-hydroxybutyl]phenol
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-methyl-6,7-dihydroindazol-4-one —— C16H16N2O3
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-methyl-6,7-dihydroindazol-4-one
—— 2-[(3R,5R)-5-phenylpyrazolidin-3-yl]phenol —— C15H16N2O
2-[(3R,5R)-5-phenylpyrazolidin-3-yl]phenol
—— 2-[(3R,5S)-5-phenylpyrazolidin-3-yl]phenol —— C15H16N2O
2-[(3R,5S)-5-phenylpyrazolidin-3-yl]phenol
—— 2-[(3S,5R)-5-phenylpyrazolidin-3-yl]phenol —— C15H16N2O
2-[(3S,5R)-5-phenylpyrazolidin-3-yl]phenol
—— (2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C17H19NO3S
(2E,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (2E,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C17H19NO3S
(2E,5E)-2-(3,3-dimethyl-2-oxobutylidene)-5-[(4-hydroxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (E)-3-(3-hydroxy-4-methoxyphenyl)-2-[1-(2,2,2-trifluoroethyl)imidazol-2-yl]prop-2-enenitrile —— C15H12F3N3O2
(E)-3-(3-hydroxy-4-methoxyphenyl)-2-[1-(2,2,2-trifluoroethyl)imidazol-2-yl]prop-2-enenitrile
—— (5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-cyclopentylimino-1,3-thiazolidin-4-one —— C15H15ClN2O2S
(5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-cyclopentylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-cyclopentylimino-1,3-thiazolidin-4-one —— C16H17ClN2O3S
(5E)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-cyclopentylimino-1,3-thiazolidin-4-one
—— (5E)-2-cyclopentylimino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C17H20N2O4S
(5E)-2-cyclopentylimino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 4-(1,2,3,6-Tetrahydropyridin-1-ium-4-yl)phenol —— C11H14NO+
4-(1,2,3,6-Tetrahydropyridin-1-ium-4-yl)phenol
—— N-[(4-ethylphenyl)methyl]-3-(2-hydroxyphenyl)-N-(pyridin-3-ylmethyl)propanamide —— C24H26N2O2
N-[(4-ethylphenyl)methyl]-3-(2-hydroxyphenyl)-N-(pyridin-3-ylmethyl)propanamide
—— 4-[2-(Methylamino)-1,3-thiazol-4-yl]benzene-1,3-diol —— C10H10N2O2S
4-[2-(Methylamino)-1,3-thiazol-4-yl]benzene-1,3-diol
—— (1S,6S)-6-[(3-hydroxy-4-methoxyphenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid —— C15H17NO5
(1S,6S)-6-[(3-hydroxy-4-methoxyphenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid
—— (1R,6S)-6-[(3-hydroxy-4-methoxyphenyl)carbamoyl]cyclohex-3-ene-1-carboxylate —— C15H16NO5-
(1R,6S)-6-[(3-hydroxy-4-methoxyphenyl)carbamoyl]cyclohex-3-ene-1-carboxylate
—— 2-(4-methoxyphenyl)ethyl 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate —— C17H18O3S
2-(4-methoxyphenyl)ethyl 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate
—— 2-[[4-[(5-Chlorothiophen-2-yl)methyl]piperazin-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C20H25ClN2O2S
2-[[4-[(5-Chlorothiophen-2-yl)methyl]piperazin-1-yl]methyl]-6-methoxy-4-prop-2-enylphenol