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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
—— (E)-2-cyano-3-(2,5-dimethyl-1-propylpyrrol-3-yl)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]prop-2-enamide —— C24H31N3O4
(E)-2-cyano-3-(2,5-dimethyl-1-propylpyrrol-3-yl)-N-[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]prop-2-enamide
—— (E)-2-cyano-3-(2,5-dimethyl-1-propylpyrrol-3-yl)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]prop-2-enamide —— C24H31N3O4
(E)-2-cyano-3-(2,5-dimethyl-1-propylpyrrol-3-yl)-N-[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]prop-2-enamide
—— (3Z,5E)-3,5-bis[(3-chloro-4-hydroxyphenyl)methylidene]-1-(2,2-difluoroethyl)piperidin-4-one —— C21H17Cl2F2NO3
(3Z,5E)-3,5-bis[(3-chloro-4-hydroxyphenyl)methylidene]-1-(2,2-difluoroethyl)piperidin-4-one
—— (3Z,5E)-1-(2,2-difluoroethyl)-3,5-bis[(4-hydroxy-3-nitrophenyl)methylidene]piperidin-4-one —— C21H17F2N3O7
(3Z,5E)-1-(2,2-difluoroethyl)-3,5-bis[(4-hydroxy-3-nitrophenyl)methylidene]piperidin-4-one
—— (3E,5E)-1-(2,2-difluoroethyl)-3,5-bis[(4-hydroxy-3-nitrophenyl)methylidene]piperidin-4-one —— C21H17F2N3O7
(3E,5E)-1-(2,2-difluoroethyl)-3,5-bis[(4-hydroxy-3-nitrophenyl)methylidene]piperidin-4-one
—— (3E,5E)-3,5-bis[(3-chloro-4-hydroxyphenyl)methylidene]-1-(2,2-difluoroethyl)piperidin-4-one —— C21H17Cl2F2NO3
(3E,5E)-3,5-bis[(3-chloro-4-hydroxyphenyl)methylidene]-1-(2,2-difluoroethyl)piperidin-4-one
—— 3,4,5-trihydroxy-N-[(5-nitrofuran-2-yl)methylideneamino]benzamide —— C12H9N3O7
3,4,5-trihydroxy-N-[(5-nitrofuran-2-yl)methylideneamino]benzamide
—— 7-ethenyl-8-(4-hydroxy-2,6-dimethoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O5
7-ethenyl-8-(4-hydroxy-2,6-dimethoxyphenyl)-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 4-Chloro-2-[3-(2-methylphenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]-6-nitrophenol —— C15H12ClN3O4
4-Chloro-2-[3-(2-methylphenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]-6-nitrophenol
—— N-[2-Hydroxy-5-nitrophenyl]-N'-[2,3-dichlorophenyl] urea —— C13H9Cl2N3O4
N-[2-Hydroxy-5-nitrophenyl]-N'-[2,3-dichlorophenyl] urea
—— 6-Ethenyl-5-(3-fluoro-2-hydroxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C22H23FO3
6-Ethenyl-5-(3-fluoro-2-hydroxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]thiophene-2-carbohydrazide —— C14H14N2O3S
N'-[1-(4-hydroxy-3-methoxyphenyl)ethenyl]thiophene-2-carbohydrazide
—— 3-[(Z)-2-(5-chloro-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C16H12ClNO2S
3-[(Z)-2-(5-chloro-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— 2-[(Z)-2-(5-hydroxy-2-nitrophenyl)ethenyl]-1H-pyrimidin-6-one —— C12H9N3O4
2-[(Z)-2-(5-hydroxy-2-nitrophenyl)ethenyl]-1H-pyrimidin-6-one
—— N-[(E)-[(1R)-cyclohex-3-en-1-yl]methylideneamino]-3,4,5-trihydroxybenzamide —— C14H16N2O4
N-[(E)-[(1R)-cyclohex-3-en-1-yl]methylideneamino]-3,4,5-trihydroxybenzamide
—— 2-[(Z)-2-(5-hydroxy-2-nitrophenyl)ethenyl]-N-methyl-1,3-thiazole-5-carboxamide —— C13H11N3O4S
2-[(Z)-2-(5-hydroxy-2-nitrophenyl)ethenyl]-N-methyl-1,3-thiazole-5-carboxamide
—— heptyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H28N2O5
heptyl (4R)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— heptyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C20H28N2O5
heptyl (4S)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 4-[(3R)-3-hydroxy-1-piperidin-1-yldecan-3-yl]phenol —— C21H35NO2
4-[(3R)-3-hydroxy-1-piperidin-1-yldecan-3-yl]phenol
—— (4S)-5-cyano-6-[2-(2,5-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4S)-5-cyano-6-[2-(2,5-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(2,3-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H24Cl2N4O4S
(4R)-5-cyano-6-[2-(2,3-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(3,4-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4R)-5-cyano-6-[2-(3,4-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-(N-phenylanilino)ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C35H30N4O4S
(4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-(N-phenylanilino)ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O5S
(4S)-5-cyano-6-[2-(2-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-6-[2-(3-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H27ClN4O4S
(4R)-6-[2-(3-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(3-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25FN4O4S
(4S)-5-cyano-6-[2-(3-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2,3-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H24Cl2N4O4S
(4S)-5-cyano-6-[2-(2,3-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— 5-(3-Fluoro-4-hydroxyphenyl)-3-(4-hydroxy-2-methylphenyl)-4-methylthiophene-2-carbaldehyde —— C19H15FO3S
5-(3-Fluoro-4-hydroxyphenyl)-3-(4-hydroxy-2-methylphenyl)-4-methylthiophene-2-carbaldehyde
—— (4R)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25ClN4O4S
(4R)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2-ethyl-6-methylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C32H32N4O4S
(4S)-5-cyano-6-[2-(2-ethyl-6-methylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(2,5-dimethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O6S
(4R)-5-cyano-6-[2-(2,5-dimethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— 4-[(3S)-3-hydroxy-1-piperidin-1-yldecan-3-yl]phenol —— C21H35NO2
4-[(3S)-3-hydroxy-1-piperidin-1-yldecan-3-yl]phenol
—— (4R)-5-cyano-6-[2-(2-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O5S
(4R)-5-cyano-6-[2-(2-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-(N-phenylanilino)ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C35H30N4O4S
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-(N-phenylanilino)ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2,4-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H24Cl2N4O4S
(4S)-5-cyano-6-[2-(2,4-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-(2-methyl-4-nitroanilino)-2-oxoethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H27N5O6S
(4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-(2-methyl-4-nitroanilino)-2-oxoethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(4-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25FN4O4S
(4R)-5-cyano-6-[2-(4-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25ClN4O4S
(4S)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(2-ethyl-6-methylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C32H32N4O4S
(4R)-5-cyano-6-[2-(2-ethyl-6-methylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(2,4-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H24Cl2N4O4S
(4R)-5-cyano-6-[2-(2,4-dichloroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-6-(2-anilino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H26N4O4S
(4R)-6-(2-anilino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(3-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H28N4O5S
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(3-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(3-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25FN4O4S
(4R)-5-cyano-6-[2-(3-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-6-[2-(2-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25ClN4O4S
(4R)-6-[2-(2-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(4-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H28N4O5S
(4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(4-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-[3-(trifluoromethyl)anilino]ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H25F3N4O4S
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-[3-(trifluoromethyl)anilino]ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(3-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H28N4O5S
(4R)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(3-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-6-[2-(2-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25ClN4O4S
(4S)-6-[2-(2-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-(2-methylanilino)-2-oxoethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H28N4O4S
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-(2-methylanilino)-2-oxoethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2,5-dimethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O6S
(4S)-5-cyano-6-[2-(2,5-dimethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide