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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
—— 1-[(1S)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea —— C19H22N2O5
1-[(1S)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea
—— 4-[(1S,2R)-2-amino-1-hydroxybutyl]-2-chlorophenol —— C10H14ClNO2
4-[(1S,2R)-2-amino-1-hydroxybutyl]-2-chlorophenol
—— 4-[(1S,2S)-2-amino-1-hydroxybutyl]-2-chlorophenol —— C10H14ClNO2
4-[(1S,2S)-2-amino-1-hydroxybutyl]-2-chlorophenol
—— 4-[(1R,2R)-2-amino-1-hydroxybutyl]-2-chlorophenol —— C10H14ClNO2
4-[(1R,2R)-2-amino-1-hydroxybutyl]-2-chlorophenol
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-3-(3-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H11NO4S2
5-[(3,4-Dihydroxyphenyl)methylidene]-3-(3-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 1-(2,5-dimethylpyrazol-3-yl)-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C16H22N4O2
1-(2,5-dimethylpyrazol-3-yl)-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 1-(2,5-dimethylpyrazol-3-yl)-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C16H22N4O2
1-(2,5-dimethylpyrazol-3-yl)-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 3-[(1R)-2,2,2-trifluoro-1-hydroxyethyl]phenol —— C8H7F3O2
3-[(1R)-2,2,2-trifluoro-1-hydroxyethyl]phenol
—— 4-[(2R)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenol —— C9H9F3O2
4-[(2R)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenol
—— 4-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenol —— C9H9F3O2
4-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenol
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-(3-methylbutoxy)benzamide —— C20H24N2O4
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-(3-methylbutoxy)benzamide
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-prop-2-enoxybenzamide —— C18H18N2O4
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-prop-2-enoxybenzamide
—— 2,6-dimethyl-3-[[(3R)-piperidin-3-yl]amino]phenol —— C13H20N2O
2,6-dimethyl-3-[[(3R)-piperidin-3-yl]amino]phenol
—— 3-[(1S)-1-[[(3S)-piperidin-3-yl]amino]ethyl]phenol —— C13H20N2O
3-[(1S)-1-[[(3S)-piperidin-3-yl]amino]ethyl]phenol
—— 3-[(1S)-1-[[(3R)-piperidin-3-yl]amino]ethyl]phenol —— C13H20N2O
3-[(1S)-1-[[(3R)-piperidin-3-yl]amino]ethyl]phenol
—— 2-methoxy-5-[[(3S)-piperidin-3-yl]amino]phenol —— C12H18N2O2
2-methoxy-5-[[(3S)-piperidin-3-yl]amino]phenol
—— 2-methoxy-5-[[(3R)-piperidin-3-yl]amino]phenol —— C12H18N2O2
2-methoxy-5-[[(3R)-piperidin-3-yl]amino]phenol
—— 3-[(1R)-1-[[(3R)-piperidin-3-yl]amino]ethyl]phenol —— C13H20N2O
3-[(1R)-1-[[(3R)-piperidin-3-yl]amino]ethyl]phenol
—— 3-[(1R)-1-[[(3S)-piperidin-3-yl]amino]ethyl]phenol —— C13H20N2O
3-[(1R)-1-[[(3S)-piperidin-3-yl]amino]ethyl]phenol
—— 1-[(2-hydroxyphenyl)methyl]-3-(2-imidazol-1-ylethyl)-1-[[(2S)-oxolan-2-yl]methyl]urea —— C18H24N4O3
1-[(2-hydroxyphenyl)methyl]-3-(2-imidazol-1-ylethyl)-1-[[(2S)-oxolan-2-yl]methyl]urea
—— 1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-[(R)-phenyl(pyridin-2-yl)methyl]urea —— C23H25N3O2
1-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]-3-[(R)-phenyl(pyridin-2-yl)methyl]urea
—— 2-methoxy-5-[(5H-pyrimido[5,4-b]indol-4-ylhydrazinylidene)methyl]phenol —— C18H15N5O2
2-methoxy-5-[(5H-pyrimido[5,4-b]indol-4-ylhydrazinylidene)methyl]phenol
—— 2,6-Dimethoxy-4-[[4-[(3-methylphenyl)methyl]piperazin-1-ium-1-yl]methyl]phenol —— C21H29N2O3+
2,6-Dimethoxy-4-[[4-[(3-methylphenyl)methyl]piperazin-1-ium-1-yl]methyl]phenol
—— 1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2R)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea —— C19H25N3O3S
1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2R)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea
—— 1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2S)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea —— C19H25N3O3S
1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2S)-2-pyrrolidin-1-yl-2-thiophen-2-ylethyl]urea
—— 1-[(2S)-2-(furan-2-yl)-2-pyrrolidin-1-ylethyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C21H29N3O3
1-[(2S)-2-(furan-2-yl)-2-pyrrolidin-1-ylethyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 1-[(2S)-2-(furan-2-yl)-2-pyrrolidin-1-ylethyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C21H29N3O3
1-[(2S)-2-(furan-2-yl)-2-pyrrolidin-1-ylethyl]-3-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 1-[(2R)-2-(furan-2-yl)-2-pyrrolidin-1-ylethyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea —— C21H29N3O3
1-[(2R)-2-(furan-2-yl)-2-pyrrolidin-1-ylethyl]-3-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]urea
—— 4-bromo-2-(3-pyridin-3-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol —— C14H12BrN3O
4-bromo-2-(3-pyridin-3-yl-2,3-dihydro-1H-pyrazol-5-yl)phenol
—— 1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[(1-morpholin-4-ylcyclohexyl)methyl]urea —— C22H35N3O3
1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[(1-morpholin-4-ylcyclohexyl)methyl]urea
—— 1-cyclopropyl-3-[(2S)-2-(furan-2-yl)-2-piperidin-1-ylethyl]-1-[(3-hydroxyphenyl)methyl]urea —— C22H29N3O3
1-cyclopropyl-3-[(2S)-2-(furan-2-yl)-2-piperidin-1-ylethyl]-1-[(3-hydroxyphenyl)methyl]urea
—— 4-[[5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-ethyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid —— C20H17ClN2O5S
4-[[5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-ethyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
—— 2-[4-(Diethylamino)phenyl]imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C20H21N3O3S
2-[4-(Diethylamino)phenyl]imino-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N-[2-[[(2-hydroxyphenyl)methyl-[[(2S)-oxolan-2-yl]methyl]carbamoyl]amino]ethyl]acetamide —— C17H25N3O4
N-[2-[[(2-hydroxyphenyl)methyl-[[(2S)-oxolan-2-yl]methyl]carbamoyl]amino]ethyl]acetamide
—— 1-[(2R)-2-(dimethylamino)-2-thiophen-2-ylethyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea —— C17H23N3O3S
1-[(2R)-2-(dimethylamino)-2-thiophen-2-ylethyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]urea
—— 3-[(2R)-2-(furan-2-yl)-2-piperidin-1-ylethyl]-1-[(2-hydroxyphenyl)methyl]-1-methylurea —— C20H27N3O3
3-[(2R)-2-(furan-2-yl)-2-piperidin-1-ylethyl]-1-[(2-hydroxyphenyl)methyl]-1-methylurea
—— 1-[4-(2-Hydroxyethyl)piperazin-1-yl]-2-(4-hydroxyphenoxy)ethanone —— C14H20N2O4
1-[4-(2-Hydroxyethyl)piperazin-1-yl]-2-(4-hydroxyphenoxy)ethanone
—— (2R)-2-[4-(2-methoxyethyl)phenoxy]-2-thiophen-2-ylethanamine —— C15H19NO2S
(2R)-2-[4-(2-methoxyethyl)phenoxy]-2-thiophen-2-ylethanamine
—— 2-Bromo-6-methoxy-4-{[(tetrahydrofuran-2-ylmethyl)amino]methyl}phenol —— C13H18BrNO3
2-Bromo-6-methoxy-4-{[(tetrahydrofuran-2-ylmethyl)amino]methyl}phenol
—— 3-[(3-Chloroanilino)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H15ClN2O4S
3-[(3-Chloroanilino)methyl]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 3-[4-Hydroxy-3-[(2-hydroxy-5-nitrophenyl)methylideneamino]-2-sulfanylidene-1,3-thiazol-5-yl]indol-2-one —— C18H10N4O5S2
3-[4-Hydroxy-3-[(2-hydroxy-5-nitrophenyl)methylideneamino]-2-sulfanylidene-1,3-thiazol-5-yl]indol-2-one
—— 3-Hexyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H21NO3S2
3-Hexyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[2-(5-Bromo-2-fluorophenyl)-6-(4-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-chlorophenol —— C24H22BrClFN2O+
2-[2-(5-Bromo-2-fluorophenyl)-6-(4-ethylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-chlorophenol
—— 5-[[(2,4-Difluorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H12F2N2O2
5-[[(2,4-Difluorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-propan-2-yloxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-5-(3-methoxy-4-propan-2-yloxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-pentoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C30H34N2O7S
2-methoxyethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-pentoxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— [4-Hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-thioxo-4-(trifluoromethyl)hexahydro-5-pyrimidinyl](2-thienyl)methanone —— C18H17F3N2O5S2
[4-Hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-thioxo-4-(trifluoromethyl)hexahydro-5-pyrimidinyl](2-thienyl)methanone
—— 4-Pyridin-1-ium-1-ylbenzene-1,2-diol —— C11H10NO2+
4-Pyridin-1-ium-1-ylbenzene-1,2-diol
—— 2-[5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,4-dimethylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]propanedinitrile —— C22H16BrN3O3S
2-[5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(2,4-dimethylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]propanedinitrile
—— N-(1,3-benzodioxol-5-yl)-2-[5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H18N2O8S
N-(1,3-benzodioxol-5-yl)-2-[5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide