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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
—— (3Z)-3-(2-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-dihydro-2H-indol-2-one —— C16H12BrNO3
(3Z)-3-(2-bromo-4-hydroxy-5-methoxybenzylidene)-1,3-dihydro-2H-indol-2-one
—— (5Z)-5-[(3-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C22H16N2O2S
(5Z)-5-[(3-hydroxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— (4E)-4-(3,5-dibromo-2-hydroxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione —— C17H12Br2N2O3
(4E)-4-(3,5-dibromo-2-hydroxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione
—— (3Z)-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one —— C16H13NO3
(3Z)-3-[(2-hydroxy-3-methoxyphenyl)methylidene]-1H-indol-2-one
—— (4E)-4-(5-bromo-2-hydroxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione —— C17H13BrN2O3
(4E)-4-(5-bromo-2-hydroxybenzylidene)-1-(4-methylphenyl)pyrazolidine-3,5-dione
—— (5Z)-3-[(Z)-benzylideneamino]-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H11N3O4S2
(5Z)-3-[(Z)-benzylideneamino]-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one —— C10H7N3O4S
(5Z)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— (6E)-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H10N2O4
(6E)-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— (6E)-6-[(2-hydroxy-5-methylanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one —— C14H12N2O4
(6E)-6-[(2-hydroxy-5-methylanilino)methylidene]-2-nitrocyclohexa-2,4-dien-1-one
—— 2-hydroxy-3-nitro-N-[(Z)-[2-[(4-nitrophenyl)methoxy]phenyl]methylideneamino]benzamide —— C21H16N4O7
2-hydroxy-3-nitro-N-[(Z)-[2-[(4-nitrophenyl)methoxy]phenyl]methylideneamino]benzamide
—— 5-ethyl-2-methoxy-4-[(2S)-pentan-2-yl]phenol —— C14H22O2
5-ethyl-2-methoxy-4-[(2S)-pentan-2-yl]phenol
—— 5-ethyl-2-methoxy-4-[(2R)-pentan-2-yl]phenol —— C14H22O2
5-ethyl-2-methoxy-4-[(2R)-pentan-2-yl]phenol
—— 2-[(1S)-2,2-difluoro-1-hydroxyethyl]phenol —— C8H8F2O2
2-[(1S)-2,2-difluoro-1-hydroxyethyl]phenol
—— 2-[(Z)-(4-hydroxy-3-methoxyphenyl)methylidene]-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one —— C14H14N2O3S
2-[(Z)-(4-hydroxy-3-methoxyphenyl)methylidene]-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3-one
—— (3Z,6Z)-3,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]piperazine-2,5-dione —— C20H18N2O6
(3Z,6Z)-3,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]piperazine-2,5-dione
—— N'-[(E)-(3-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-4-hydroxy-3-methoxybenzohydrazide —— C17H18N2O5
N'-[(E)-(3-ethoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-4-hydroxy-3-methoxybenzohydrazide
—— ethyl (2Z)-2-[(1-ethyl-3-methylpyrazol-4-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H24N4O4S
ethyl (2Z)-2-[(1-ethyl-3-methylpyrazol-4-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[(4-Hydroxy-3-methoxy-phenyl)methylidene]-2-methyl-1,3-oxazol-5-one —— C12H11NO4
4-[(4-Hydroxy-3-methoxy-phenyl)methylidene]-2-methyl-1,3-oxazol-5-one
—— (4E)-4-(3,4-dihydroxybenzylidene)-1-(3,4-dimethylphenyl)pyrazolidine-3,5-dione —— C18H16N2O4
(4E)-4-(3,4-dihydroxybenzylidene)-1-(3,4-dimethylphenyl)pyrazolidine-3,5-dione
—— 4-[(1S)-1-hydroxy-2-piperidin-1-ylethyl]phenol —— C13H19NO2
4-[(1S)-1-hydroxy-2-piperidin-1-ylethyl]phenol
—— (4E)-4-[(4-hydroxy-3-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one —— C16H10N2O5
(4E)-4-[(4-hydroxy-3-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
—— 2-amino-6-[(2R)-butan-2-yl]-4-nitrophenol —— C10H14N2O3
2-amino-6-[(2R)-butan-2-yl]-4-nitrophenol
—— (2S)-2-(N-[2-(benzotriazol-1-yl)acetyl]-3,4-dimethoxyanilino)-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C30H33N5O7
(2S)-2-(N-[2-(benzotriazol-1-yl)acetyl]-3,4-dimethoxyanilino)-2-(4-hydroxy-3-methoxyphenyl)-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— (5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-1,3-thiazolidine-2,4-dione —— C12H11NO4S
(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-methyl-1,3-thiazolidine-2,4-dione
—— 3,4,5-trihydroxy-N'-[(1E)-1-(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide —— C15H14N2O6
3,4,5-trihydroxy-N'-[(1E)-1-(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)ethyl]benzohydrazide
—— 3-[(2R)-1-hydroxy-2-(methylamino)propan-2-yl]phenol —— C10H15NO2
3-[(2R)-1-hydroxy-2-(methylamino)propan-2-yl]phenol
—— 4-[(1S)-1-(cyclopentylamino)-2-hydroxyethyl]phenol —— C13H19NO2
4-[(1S)-1-(cyclopentylamino)-2-hydroxyethyl]phenol
—— 3-[(1S)-2-hydroxy-1-(propan-2-ylamino)ethyl]phenol —— C11H17NO2
3-[(1S)-2-hydroxy-1-(propan-2-ylamino)ethyl]phenol
—— (5Z)-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C11H7N3O6S2
(5Z)-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-[(2S)-1-hydroxy-2-(methylamino)propan-2-yl]phenol —— C10H15NO2
3-[(2S)-1-hydroxy-2-(methylamino)propan-2-yl]phenol
—— 4-[(1S)-1-(ethylamino)-2-hydroxyethyl]-2,6-dimethylphenol —— C12H19NO2
4-[(1S)-1-(ethylamino)-2-hydroxyethyl]-2,6-dimethylphenol
—— 4-[(1S)-1-(cyclopropylamino)-2-hydroxyethyl]phenol —— C11H15NO2
4-[(1S)-1-(cyclopropylamino)-2-hydroxyethyl]phenol
—— (5Z)-5-(3,4-dihydroxybenzylidene)-3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one —— C13H11NO3S2
(5Z)-5-(3,4-dihydroxybenzylidene)-3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one
—— 3-[(1R)-1-(ethylamino)-2-hydroxyethyl]phenol —— C10H15NO2
3-[(1R)-1-(ethylamino)-2-hydroxyethyl]phenol
—— N-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]octanamide —— C19H24N2O4S2
N-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]octanamide
—— 3-[(2S)-1-hydroxy-2-(propan-2-ylamino)propan-2-yl]phenol —— C12H19NO2
3-[(2S)-1-hydroxy-2-(propan-2-ylamino)propan-2-yl]phenol
—— 3-[(2S)-2-(ethylamino)-1-hydroxypropan-2-yl]phenol —— C11H17NO2
3-[(2S)-2-(ethylamino)-1-hydroxypropan-2-yl]phenol
—— (5Z)-3-benzyl-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H13NO2S2
(5Z)-3-benzyl-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E,8E,11E,14E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide —— C28H41NO3
(5E,8E,11E,14E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide
—— 3-[(1R)-2-hydroxy-1-piperazin-1-ylethyl]phenol —— C12H18N2O2
3-[(1R)-2-hydroxy-1-piperazin-1-ylethyl]phenol
—— 3-[(1S)-1-(ethylamino)-2-hydroxyethyl]phenol —— C10H15NO2
3-[(1S)-1-(ethylamino)-2-hydroxyethyl]phenol
—— (4E)-4-[[3,4-dihydroxy-5-(phenylsulfanylmethyl)phenyl]methylidene]-1-phenylpyrazolidine-3,5-dione —— C23H18N2O4S
(4E)-4-[[3,4-dihydroxy-5-(phenylsulfanylmethyl)phenyl]methylidene]-1-phenylpyrazolidine-3,5-dione
—— 4-[(1S)-2-hydroxy-1-piperazin-1-ylethyl]phenol —— C12H18N2O2
4-[(1S)-2-hydroxy-1-piperazin-1-ylethyl]phenol
—— 5-chloro-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N,1-dimethylimidazole-4-sulfonamide —— C13H16ClN3O3S
5-chloro-N-[(1R)-1-(2-hydroxyphenyl)ethyl]-N,1-dimethylimidazole-4-sulfonamide
—— (4E)-4-[[4-hydroxy-3-methoxy-5-(phenylsulfanylmethyl)phenyl]methylidene]-1-phenylpyrazolidine-3,5-dione —— C24H20N2O4S
(4E)-4-[[4-hydroxy-3-methoxy-5-(phenylsulfanylmethyl)phenyl]methylidene]-1-phenylpyrazolidine-3,5-dione
—— 2-[(1S)-1-[(1-ethylpiperidin-4-yl)amino]ethyl]-4-methylphenol —— C16H26N2O
2-[(1S)-1-[(1-ethylpiperidin-4-yl)amino]ethyl]-4-methylphenol
—— 2-[(1R)-1-[2-[(2R)-oxolan-2-yl]ethylamino]ethyl]benzene-1,4-diol —— C14H21NO3
2-[(1R)-1-[2-[(2R)-oxolan-2-yl]ethylamino]ethyl]benzene-1,4-diol
—— 4-methyl-2-[(1S)-1-[2-[(2S)-oxolan-2-yl]ethylamino]ethyl]phenol —— C15H23NO2
4-methyl-2-[(1S)-1-[2-[(2S)-oxolan-2-yl]ethylamino]ethyl]phenol
—— 5-methoxy-2-[(1R)-1-[2-[(2R)-oxolan-2-yl]ethylamino]ethyl]phenol —— C15H23NO3
5-methoxy-2-[(1R)-1-[2-[(2R)-oxolan-2-yl]ethylamino]ethyl]phenol
—— 2-methoxy-4-[(1R)-1-[2-[(2R)-oxolan-2-yl]ethylamino]ethyl]phenol —— C15H23NO3
2-methoxy-4-[(1R)-1-[2-[(2R)-oxolan-2-yl]ethylamino]ethyl]phenol