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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)-3-(3-hydroxy-4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C14H12N2O2S
(E)-3-(3-hydroxy-4-methoxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]thiophene-2-carboxamide —— C13H11BrN2O3S
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]thiophene-2-carboxamide
—— 2-methoxy-5-[[[(2S,3R)-2-phenyloxolan-3-yl]amino]methyl]phenol —— C18H21NO3
2-methoxy-5-[[[(2S,3R)-2-phenyloxolan-3-yl]amino]methyl]phenol
—— 2-methoxy-5-[[[(2R,3R)-2-phenyloxolan-3-yl]amino]methyl]phenol —— C18H21NO3
2-methoxy-5-[[[(2R,3R)-2-phenyloxolan-3-yl]amino]methyl]phenol
—— (2E,5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one —— C19H14ClNO5S
(2E,5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-1,3-thiazolidin-4-one
—— (E)-3-[2,5-dimethyl-1-(5-methyl-1,2-oxazol-3-yl)pyrrol-3-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C20H20N2O4
(E)-3-[2,5-dimethyl-1-(5-methyl-1,2-oxazol-3-yl)pyrrol-3-yl]-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (2E,5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one —— C16H16ClNO4S
(2E,5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one
—— (5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(2,4-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H15ClN2O3S
(5E)-5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-(2,4-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— 2-methoxy-5-[[[(2R,3S)-2-phenyloxolan-3-yl]amino]methyl]phenol —— C18H21NO3
2-methoxy-5-[[[(2R,3S)-2-phenyloxolan-3-yl]amino]methyl]phenol
—— 2-methoxy-5-[[[(2S,3S)-2-phenyloxolan-3-yl]amino]methyl]phenol —— C18H21NO3
2-methoxy-5-[[[(2S,3S)-2-phenyloxolan-3-yl]amino]methyl]phenol
—— (E)-3-(3-chloro-4,5-dihydroxyphenyl)-2-(2,5-dichlorophenyl)sulfonylprop-2-enenitrile —— C15H8Cl3NO4S
(E)-3-(3-chloro-4,5-dihydroxyphenyl)-2-(2,5-dichlorophenyl)sulfonylprop-2-enenitrile
—— (2S,6S)-N-[2-(3-hydroxyphenyl)ethyl]-2,6-dimethylthiomorpholine-4-carboxamide —— C15H22N2O2S
(2S,6S)-N-[2-(3-hydroxyphenyl)ethyl]-2,6-dimethylthiomorpholine-4-carboxamide
—— 1-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[2-(3-hydroxyphenyl)ethyl]urea —— C16H19N3O2S
1-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[2-(3-hydroxyphenyl)ethyl]urea
—— 1-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[2-(3-hydroxyphenyl)ethyl]urea —— C16H19N3O2S
1-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[2-(3-hydroxyphenyl)ethyl]urea
—— (2R,6R)-N-[2-(3-hydroxyphenyl)ethyl]-2,6-dimethylthiomorpholine-4-carboxamide —— C15H22N2O2S
(2R,6R)-N-[2-(3-hydroxyphenyl)ethyl]-2,6-dimethylthiomorpholine-4-carboxamide
—— (2R,6S)-N-[2-(3-hydroxyphenyl)ethyl]-2,6-dimethylthiomorpholine-4-carboxamide —— C15H22N2O2S
(2R,6S)-N-[2-(3-hydroxyphenyl)ethyl]-2,6-dimethylthiomorpholine-4-carboxamide
—— ethyl 2-[2-[[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]carbamoylamino]-1,3-thiazol-4-yl]acetate —— C19H25N3O6S
ethyl 2-[2-[[(2R)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]carbamoylamino]-1,3-thiazol-4-yl]acetate
—— ethyl 2-[2-[[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]carbamoylamino]-1,3-thiazol-4-yl]acetate —— C19H25N3O6S
ethyl 2-[2-[[(2S)-3-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]propyl]carbamoylamino]-1,3-thiazol-4-yl]acetate
—— (3S)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]-3-methylhexanamide —— C19H25NO3
(3S)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]-3-methylhexanamide
—— (3R)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]-3-methylhexanamide —— C19H25NO3
(3R)-N-(furan-2-ylmethyl)-N-[(2-hydroxyphenyl)methyl]-3-methylhexanamide
—— 2-[[4-(1,3-Benzodioxol-5-ylmethyl)piperazin-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol —— C23H28N2O4
2-[[4-(1,3-Benzodioxol-5-ylmethyl)piperazin-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol
—— 2-[[4-(1,3-Benzodioxol-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol —— C23H30N2O4+2
2-[[4-(1,3-Benzodioxol-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-4-methoxy-6-prop-2-enylphenol
—— 2-[[4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-(2-methylfuran-3-yl)-1,2,4-triazol-3-yl]sulfanyl]acetate —— C17H15N4O5S-
2-[[4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-(2-methylfuran-3-yl)-1,2,4-triazol-3-yl]sulfanyl]acetate
—— 2-[[4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-(2-methylfuran-3-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid —— C17H16N4O5S
2-[[4-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-(2-methylfuran-3-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid
—— (2S)-2-(3-hydroxyphenyl)-2-piperidin-1-ylacetonitrile —— C13H16N2O
(2S)-2-(3-hydroxyphenyl)-2-piperidin-1-ylacetonitrile
—— (2R)-2-(3-hydroxyphenyl)-2-morpholin-4-ylacetonitrile —— C12H14N2O2
(2R)-2-(3-hydroxyphenyl)-2-morpholin-4-ylacetonitrile
—— (2S)-2-[4-[(S)-cyano-(3-hydroxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(3-hydroxyphenyl)acetonitrile —— C20H22N4O2+2
(2S)-2-[4-[(S)-cyano-(3-hydroxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(3-hydroxyphenyl)acetonitrile
—— (2R)-2-(3-hydroxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile —— C13H17N2O+
(2R)-2-(3-hydroxyphenyl)-2-piperidin-1-ium-1-ylacetonitrile
—— 2-(5,6-dimethyl-4-oxo-3H-thieno[2,3-d]pyrimidin-2-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C18H18N4O4S
2-(5,6-dimethyl-4-oxo-3H-thieno[2,3-d]pyrimidin-2-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— 3-[(2Z)-2-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-6-methyl-4H-1,2,4-triazin-5-one —— C12H12BrN5O3
3-[(2Z)-2-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-6-methyl-4H-1,2,4-triazin-5-one
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(2R)-1-methoxypropan-2-yl]thiourea —— C13H19N3O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(2R)-1-methoxypropan-2-yl]thiourea
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4-methoxyphenyl)methyl]thiourea —— C17H19N3O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(4-methoxyphenyl)methyl]thiourea
—— 1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(2S)-1-methoxypropan-2-yl]thiourea —— C13H19N3O3S
1-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-[(2S)-1-methoxypropan-2-yl]thiourea
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-chlorobenzamide —— C15H12BrClN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-chlorobenzamide
—— 2-Methoxy-6-[[4-[(2-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-prop-2-enylphenol —— C23H32N2O2+2
2-Methoxy-6-[[4-[(2-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-prop-2-enylphenol
—— 2-Methoxy-6-[[4-[(2-methylphenyl)methyl]piperazin-1-yl]methyl]-4-prop-2-enylphenol —— C23H30N2O2
2-Methoxy-6-[[4-[(2-methylphenyl)methyl]piperazin-1-yl]methyl]-4-prop-2-enylphenol
—— 5-bromo-4-[[[(2R)-3-(5,6-dimethylbenzimidazol-1-yl)-2-hydroxypropyl]amino]methyl]-2-methoxyphenol —— C20H24BrN3O3
5-bromo-4-[[[(2R)-3-(5,6-dimethylbenzimidazol-1-yl)-2-hydroxypropyl]amino]methyl]-2-methoxyphenol
—— 5-bromo-4-[[[(2S)-3-(5,6-dimethylbenzimidazol-1-yl)-2-hydroxypropyl]amino]methyl]-2-methoxyphenol —— C20H24BrN3O3
5-bromo-4-[[[(2S)-3-(5,6-dimethylbenzimidazol-1-yl)-2-hydroxypropyl]amino]methyl]-2-methoxyphenol
—— N-[(1R)-1-(3,4-dichlorophenyl)ethyl]-2-(4-hydroxyphenoxy)acetamide —— C16H15Cl2NO3
N-[(1R)-1-(3,4-dichlorophenyl)ethyl]-2-(4-hydroxyphenoxy)acetamide
—— N-[(1R)-1-(4-ethylphenyl)ethyl]-3-(2-hydroxyphenyl)propanamide —— C19H23NO2
N-[(1R)-1-(4-ethylphenyl)ethyl]-3-(2-hydroxyphenyl)propanamide
—— N-[(1S)-1-(4-ethylphenyl)ethyl]-3-(2-hydroxyphenyl)propanamide —— C19H23NO2
N-[(1S)-1-(4-ethylphenyl)ethyl]-3-(2-hydroxyphenyl)propanamide
—— N-[(1S)-1-(3,4-dichlorophenyl)ethyl]-2-(4-hydroxyphenoxy)acetamide —— C16H15Cl2NO3
N-[(1S)-1-(3,4-dichlorophenyl)ethyl]-2-(4-hydroxyphenoxy)acetamide
—— 1-cyclohexyl-1-[(2-hydroxyphenyl)methyl]-3-[[(2R)-oxolan-2-yl]methyl]urea —— C19H28N2O3
1-cyclohexyl-1-[(2-hydroxyphenyl)methyl]-3-[[(2R)-oxolan-2-yl]methyl]urea
—— 1-cyclohexyl-1-[(2-hydroxyphenyl)methyl]-3-[[(2S)-oxolan-2-yl]methyl]urea —— C19H28N2O3
1-cyclohexyl-1-[(2-hydroxyphenyl)methyl]-3-[[(2S)-oxolan-2-yl]methyl]urea
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-3,5-dimethyl-1-[(4-methylphenyl)methyl]pyrazole-4-carboxamide —— C21H22N4O4
N-[(2-hydroxy-5-nitrophenyl)methyl]-3,5-dimethyl-1-[(4-methylphenyl)methyl]pyrazole-4-carboxamide
—— 2-(3-fluoro-4-methoxyphenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C16H15FN2O5
2-(3-fluoro-4-methoxyphenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— (5S)-N-[(2-hydroxy-5-nitrophenyl)methyl]-5-methyl-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide —— C17H18N2O4S
(5S)-N-[(2-hydroxy-5-nitrophenyl)methyl]-5-methyl-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide
—— (2S)-2-(4-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methylbutanamide —— C18H19ClN2O4
(2S)-2-(4-chlorophenyl)-N-[(2-hydroxy-5-nitrophenyl)methyl]-3-methylbutanamide
—— 5-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzofuran-2-carboxamide —— C16H11ClN2O5
5-chloro-N-[(2-hydroxy-5-nitrophenyl)methyl]-1-benzofuran-2-carboxamide
—— 4-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylamino]-4-oxobutanoic acid —— C12H14BrNO5
4-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylamino]-4-oxobutanoic acid