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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-(1-adamantyl)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]acetamide —— C19H24N2O2
2-(1-adamantyl)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]acetamide
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1R,2S)-2-methylcyclohexyl]thiourea —— C15H21N3OS
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1R,2S)-2-methylcyclohexyl]thiourea
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1S,2S)-2-methylcyclohexyl]thiourea —— C15H21N3OS
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1S,2S)-2-methylcyclohexyl]thiourea
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1S,2R)-2-methylcyclohexyl]thiourea —— C15H21N3OS
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1S,2R)-2-methylcyclohexyl]thiourea
—— 1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1R,2R)-2-methylcyclohexyl]thiourea —— C15H21N3OS
1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(1R,2R)-2-methylcyclohexyl]thiourea
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-(4-methylpiperidin-1-ium-1-yl)ethanone —— C22H28N3O3S+
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-(4-methylpiperidin-1-ium-1-yl)ethanone
—— 1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ium-4-ylethanone —— C20H24N3O4S+
1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ium-4-ylethanone
—— 1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-(4-methylpiperidin-1-ium-1-yl)ethanone —— C22H28N3O3S+
1-[(3R)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-(4-methylpiperidin-1-ium-1-yl)ethanone
—— (2-hydroxy-5-methoxyphenyl)-[5-[6-(trifluoromethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-ylidene]pyrrol-3-yl]methanone —— C19H13F3N4O3
(2-hydroxy-5-methoxyphenyl)-[5-[6-(trifluoromethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-ylidene]pyrrol-3-yl]methanone
—— 1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ium-4-ylethanone —— C20H24N3O4S+
1-[(3S)-3-(2-hydroxy-3-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-2-morpholin-4-ium-4-ylethanone
—— 2-Methoxy-5-(thieno[2,3-d]pyrimidin-4-ylamino)phenol —— C13H11N3O2S
2-Methoxy-5-(thieno[2,3-d]pyrimidin-4-ylamino)phenol
—— 2-Methoxy-5-(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylamino)phenol —— C17H17N3O2S
2-Methoxy-5-(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylamino)phenol
—— 2-Methoxy-5-[[10-(morpholin-4-ylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraen-12-yl]amino]phenol —— C21H24N4O3S
2-Methoxy-5-[[10-(morpholin-4-ylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraen-12-yl]amino]phenol
—— 2-methoxy-5-[[(7S)-7-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-yl]amino]phenol —— C18H19N3O2S
2-methoxy-5-[[(7S)-7-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-yl]amino]phenol
—— 5-[(5,6-Dimethylthieno[2,3-d]pyrimidin-4-yl)amino]-2-methoxyphenol —— C15H15N3O2S
5-[(5,6-Dimethylthieno[2,3-d]pyrimidin-4-yl)amino]-2-methoxyphenol
—— 2-Methoxy-5-[[10-(morpholin-4-ium-4-ylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraen-12-yl]amino]phenol —— C21H25N4O3S+
2-Methoxy-5-[[10-(morpholin-4-ium-4-ylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraen-12-yl]amino]phenol
—— 3-hydroxy-N-[(1S)-2-methyl-1-pyridin-2-ylpropyl]-4-nitrobenzamide —— C16H17N3O4
3-hydroxy-N-[(1S)-2-methyl-1-pyridin-2-ylpropyl]-4-nitrobenzamide
—— 3-hydroxy-N-[(1R)-2-methyl-1-pyridin-2-ylpropyl]-4-nitrobenzamide —— C16H17N3O4
3-hydroxy-N-[(1R)-2-methyl-1-pyridin-2-ylpropyl]-4-nitrobenzamide
—— (2R)-2-(4-hydroxyphenyl)-2-(4-methylpiperazin-1-yl)acetonitrile —— C13H17N3O
(2R)-2-(4-hydroxyphenyl)-2-(4-methylpiperazin-1-yl)acetonitrile
—— (1S,2R)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide —— C18H17F2NO3
(1S,2R)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide
—— (1R,2R)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide —— C18H17F2NO3
(1R,2R)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide
—— (1R,2S)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide —— C18H17F2NO3
(1R,2S)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide
—— (1S,2S)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide —— C18H17F2NO3
(1S,2S)-2-(2,5-difluorophenyl)-N-[(3-hydroxy-4-methoxyphenyl)methyl]cyclopropane-1-carboxamide
—— 4-[2-[(1R)-1-ethoxyethyl]-1,3-thiazol-4-yl]benzene-1,2-diol —— C13H15NO3S
4-[2-[(1R)-1-ethoxyethyl]-1,3-thiazol-4-yl]benzene-1,2-diol
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propanamide —— C19H18N4O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propanamide
—— (3S)-6-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-3,4-dihydro-2H-chromene-3-carboxamide —— C17H15ClN2O5
(3S)-6-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-3,4-dihydro-2H-chromene-3-carboxamide
—— 7-fluoro-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methyl-1-benzofuran-2-carboxamide —— C17H13FN2O5
7-fluoro-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methyl-1-benzofuran-2-carboxamide
—— 3-(ethoxymethyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzofuran-2-carboxamide —— C19H18N2O6
3-(ethoxymethyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzofuran-2-carboxamide
—— 5-ethoxy-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methyl-1-benzofuran-2-carboxamide —— C19H18N2O6
5-ethoxy-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methyl-1-benzofuran-2-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-oxo-1,3-thiazolidin-3-yl)acetamide —— C12H13N3O5S
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-(2-oxo-1,3-thiazolidin-3-yl)acetamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-thiophen-3-yl-1,3-thiazole-4-carboxamide —— C15H11N3O4S2
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-thiophen-3-yl-1,3-thiazole-4-carboxamide
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-4-methyl-2-thiophen-3-yl-1,3-thiazole-5-carboxamide —— C16H13N3O4S2
N-[(2-hydroxy-5-nitrophenyl)methyl]-4-methyl-2-thiophen-3-yl-1,3-thiazole-5-carboxamide
—— (E)-3-(1-benzylpyrazol-4-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]prop-2-enamide —— C20H18N4O4
(E)-3-(1-benzylpyrazol-4-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]prop-2-enamide
—— 4-bromo-5-[(Z)-[(2-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol —— C14H12BrClN2O2
4-bromo-5-[(Z)-[(2-chlorophenyl)hydrazinylidene]methyl]-2-methoxyphenol
—— 3-hydroxy-N-[(1R)-1-(5-methyl-1,3-thiazol-2-yl)propyl]-4-nitrobenzamide —— C14H15N3O4S
3-hydroxy-N-[(1R)-1-(5-methyl-1,3-thiazol-2-yl)propyl]-4-nitrobenzamide
—— 3-hydroxy-N-[(1S)-1-(5-methyl-1,3-thiazol-2-yl)propyl]-4-nitrobenzamide —— C14H15N3O4S
3-hydroxy-N-[(1S)-1-(5-methyl-1,3-thiazol-2-yl)propyl]-4-nitrobenzamide
—— [(2R)-1-oxo-1-(prop-2-enylamino)propan-2-yl] 2-(4-hydroxyphenyl)acetate —— C14H17NO4
[(2R)-1-oxo-1-(prop-2-enylamino)propan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2S)-1-(methoxycarbonylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C13H15NO6
[(2S)-1-(methoxycarbonylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2R)-1-(cycloheptylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C18H25NO4
[(2R)-1-(cycloheptylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2S)-1-[[(3S)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C15H19NO6S
[(2S)-1-[[(3S)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2R)-1-(methoxycarbonylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C13H15NO6
[(2R)-1-(methoxycarbonylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2R)-1-[[(3S)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C15H19NO6S
[(2R)-1-[[(3S)-1,1-dioxothiolan-3-yl]amino]-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [(2S)-1-(2-methoxyethylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C14H19NO5
[(2S)-1-(2-methoxyethylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— 4-bromo-2-methoxy-5-[(Z)-(4-methylpiperazin-4-ium-1-yl)iminomethyl]phenol —— C13H19BrN3O2+
4-bromo-2-methoxy-5-[(Z)-(4-methylpiperazin-4-ium-1-yl)iminomethyl]phenol
—— N-[(2-hydroxyphenyl)methyl]-N-[[(2R)-oxolan-2-yl]methyl]-3-pyridin-4-ylpropanamide —— C20H24N2O3
N-[(2-hydroxyphenyl)methyl]-N-[[(2R)-oxolan-2-yl]methyl]-3-pyridin-4-ylpropanamide
—— 2-(3,5-dimethylpyrazol-1-yl)-N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C19H25N3O3
2-(3,5-dimethylpyrazol-1-yl)-N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]acetamide
—— 2-(3,5-dimethylpyrazol-1-yl)-N-[(2-hydroxyphenyl)methyl]-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C19H25N3O3
2-(3,5-dimethylpyrazol-1-yl)-N-[(2-hydroxyphenyl)methyl]-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— N-[(2-hydroxyphenyl)methyl]-2-(1-methylpyrazol-4-yl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide —— C18H23N3O3
N-[(2-hydroxyphenyl)methyl]-2-(1-methylpyrazol-4-yl)-N-[[(2R)-oxolan-2-yl]methyl]acetamide
—— N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]-3-pyridin-4-ylpropanamide —— C20H24N2O3
N-[(2-hydroxyphenyl)methyl]-N-[[(2S)-oxolan-2-yl]methyl]-3-pyridin-4-ylpropanamide
—— N-[(2-hydroxyphenyl)methyl]-3-(1-methylpyrazol-4-yl)-N-[[(2R)-oxolan-2-yl]methyl]propanamide —— C19H25N3O3
N-[(2-hydroxyphenyl)methyl]-3-(1-methylpyrazol-4-yl)-N-[[(2R)-oxolan-2-yl]methyl]propanamide