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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
—— (8R,9R)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C25H26FN5O4
(8R,9R)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (8R,9S)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one —— C25H26FN5O4
(8R,9S)-4-tert-butyl-10-(4-fluorophenyl)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,4,5,10,12-pentazatricyclo[7.3.0.03,7]dodeca-1(12),2,6-trien-11-one
—— (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-13-(methoxymethyl)-11-methyl-8-thia-3,5,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),9,11-tetraen-6-one —— C19H18ClN3O4S
(4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-13-(methoxymethyl)-11-methyl-8-thia-3,5,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),9,11-tetraen-6-one
—— 2-methoxy-5-[(Z)-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazinylidene]methyl]phenol —— C16H15N3O2S
2-methoxy-5-[(Z)-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazinylidene]methyl]phenol
—— 5-[(Z)-[(3-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H13ClN2O2
5-[(Z)-[(3-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— ethyl N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]carbamate —— C11H13BrN2O4
ethyl N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]carbamate
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[(3R)-1-propan-2-ylpiperidin-3-yl]methyl]urea —— C21H33N3O3
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[(3R)-1-propan-2-ylpiperidin-3-yl]methyl]urea
—— 1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[(3S)-1-propan-2-ylpiperidin-3-yl]methyl]urea —— C21H33N3O3
1-cyclopropyl-1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[(3S)-1-propan-2-ylpiperidin-3-yl]methyl]urea
—— methyl N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]carbamate —— C10H11BrN2O4
methyl N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]carbamate
—— 5-[(Z)-[(3-chloro-4-methylphenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C15H15ClN2O2
5-[(Z)-[(3-chloro-4-methylphenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 1-[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]-3-(1,3,4-thiadiazol-2-yl)urea —— C12H14N4O3S
1-[(1R)-1-(2-hydroxy-5-methoxyphenyl)ethyl]-3-(1,3,4-thiadiazol-2-yl)urea
—— 1-[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]-3-(1,3,4-thiadiazol-2-yl)urea —— C12H14N4O3S
1-[(1S)-1-(2-hydroxy-5-methoxyphenyl)ethyl]-3-(1,3,4-thiadiazol-2-yl)urea
—— [(2S)-1-[[(3R)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C15H19NO6S
[(2S)-1-[[(3R)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— 3-(2-hydroxyphenyl)-N-[(1S)-1-phenylhexyl]propanamide —— C21H27NO2
3-(2-hydroxyphenyl)-N-[(1S)-1-phenylhexyl]propanamide
—— 3-(2-hydroxyphenyl)-N-[(1R)-1-phenylhexyl]propanamide —— C21H27NO2
3-(2-hydroxyphenyl)-N-[(1R)-1-phenylhexyl]propanamide
—— [(2R)-1-[[(3R)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C15H19NO6S
[(2R)-1-[[(3R)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2S)-1-(cycloheptylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C18H25NO4
[(2S)-1-(cycloheptylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— 2-methoxy-5-[(Z)-[(3-methylphenyl)hydrazinylidene]methyl]phenol —— C15H16N2O2
2-methoxy-5-[(Z)-[(3-methylphenyl)hydrazinylidene]methyl]phenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-chlorobenzamide —— C15H12BrClN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-chlorobenzamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-3-carboxamide —— C14H12BrN3O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-3-carboxamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C15H13BrN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 5-[(Z)-(diphenylhydrazinylidene)methyl]-2-methoxyphenol —— C20H18N2O2
5-[(Z)-(diphenylhydrazinylidene)methyl]-2-methoxyphenol
—— 4-bromo-2-methoxy-5-[(Z)-(4-methylpiperazin-1-yl)iminomethyl]phenol —— C13H18BrN3O2
4-bromo-2-methoxy-5-[(Z)-(4-methylpiperazin-1-yl)iminomethyl]phenol
—— 4-bromo-2-methoxy-5-[(Z)-[(2-nitrophenyl)hydrazinylidene]methyl]phenol —— C14H12BrN3O4
4-bromo-2-methoxy-5-[(Z)-[(2-nitrophenyl)hydrazinylidene]methyl]phenol
—— 4-bromo-5-[(Z)-[(2,4-difluorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H11BrF2N2O2
4-bromo-5-[(Z)-[(2,4-difluorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 4-[[[(2S)-1-methoxypropan-2-yl]amino]methyl]-2-nitrophenol —— C11H16N2O4
4-[[[(2S)-1-methoxypropan-2-yl]amino]methyl]-2-nitrophenol
—— 4-[[[(2R)-1-methoxypropan-2-yl]amino]methyl]-2-nitrophenol —— C11H16N2O4
4-[[[(2R)-1-methoxypropan-2-yl]amino]methyl]-2-nitrophenol
—— 2-[[[(1S)-1-(4,5-dimethoxy-2-methylphenyl)ethyl]amino]methyl]-6-methoxyphenol —— C19H25NO4
2-[[[(1S)-1-(4,5-dimethoxy-2-methylphenyl)ethyl]amino]methyl]-6-methoxyphenol
—— 2-[[[(1R)-1-(4,5-dimethoxy-2-methylphenyl)ethyl]amino]methyl]-6-methoxyphenol —— C19H25NO4
2-[[[(1R)-1-(4,5-dimethoxy-2-methylphenyl)ethyl]amino]methyl]-6-methoxyphenol
—— (2E,6S)-2-[(3-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C19H18O2
(2E,6S)-2-[(3-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— (2R)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]oxolane-2-carboxamide —— C17H19NO4
(2R)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]oxolane-2-carboxamide
—— (2E,6R)-2-[(3-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C19H18O2
(2E,6R)-2-[(3-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— 3-[(Z)-2-[5-(5-bromothiophen-2-yl)-1,3,4-oxadiazol-2-yl]-2-chloroethenyl]phenol —— C14H8BrClN2O2S
3-[(Z)-2-[5-(5-bromothiophen-2-yl)-1,3,4-oxadiazol-2-yl]-2-chloroethenyl]phenol
—— N-[(2-hydroxyphenyl)methyl]-N-[[(2R)-oxolan-2-yl]methyl]propanamide —— C15H21NO3
N-[(2-hydroxyphenyl)methyl]-N-[[(2R)-oxolan-2-yl]methyl]propanamide
—— (2E,6S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C20H19BrO3
(2E,6S)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]propanamide —— C15H21NO3
N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]propanamide
—— (2S)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]oxolane-2-carboxamide —— C17H19NO4
(2S)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]oxolane-2-carboxamide
—— (2E,6S)-2-[(4-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C19H18O2
(2E,6S)-2-[(4-hydroxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— (2E,6R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C20H19BrO3
(2E,6R)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— 5-[(2R)-2-[(1,3-benzoxazol-2-ylamino)methyl]-3-hydroxypropyl]-2-methoxyphenol —— C18H20N2O4
5-[(2R)-2-[(1,3-benzoxazol-2-ylamino)methyl]-3-hydroxypropyl]-2-methoxyphenol
—— 5-[(2S)-2-[(1,3-benzoxazol-2-ylamino)methyl]-3-hydroxypropyl]-2-methoxyphenol —— C18H20N2O4
5-[(2S)-2-[(1,3-benzoxazol-2-ylamino)methyl]-3-hydroxypropyl]-2-methoxyphenol
—— 2-fluoro-6-[[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]amino]benzonitrile —— C18H19FN2O3
2-fluoro-6-[[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]amino]benzonitrile
—— (2E,6R)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one —— C20H19ClO3
(2E,6R)-2-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-6-phenylcyclohexan-1-one
—— 2-fluoro-6-[[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]amino]benzonitrile —— C18H19FN2O3
2-fluoro-6-[[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]amino]benzonitrile
—— 3-[(Z)-2-chloro-2-[5-(5-methyl-3-phenyl-1,2-oxazol-4-yl)-1,3,4-oxadiazol-2-yl]ethenyl]phenol —— C20H14ClN3O3
3-[(Z)-2-chloro-2-[5-(5-methyl-3-phenyl-1,2-oxazol-4-yl)-1,3,4-oxadiazol-2-yl]ethenyl]phenol
—— 3-[(Z)-2-chloro-2-[5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazol-2-yl]ethenyl]phenol —— C16H13ClN2O3
3-[(Z)-2-chloro-2-[5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazol-2-yl]ethenyl]phenol
—— methyl 3-[4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]propanoate —— C15H19NO3
methyl 3-[4-(4-hydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]propanoate
—— 5-[(Z)-2-chloro-2-[5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol —— C17H15ClN2O4
5-[(Z)-2-chloro-2-[5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazol-2-yl]ethenyl]-2-methoxyphenol
—— 5-[(Z)-2-(1,3-benzoxazol-2-yl)-2-chloroethenyl]-2-methoxyphenol —— C16H12ClNO3
5-[(Z)-2-(1,3-benzoxazol-2-yl)-2-chloroethenyl]-2-methoxyphenol
—— 5-[(Z)-2-chloro-2-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)ethenyl]-2-methoxyphenol —— C15H11ClN2O3S
5-[(Z)-2-chloro-2-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)ethenyl]-2-methoxyphenol