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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
—— Benzenecarbothioamide, N-[3-(diethylamino)propyl]-4-hydroxy-3-methoxy- —— C15H24N2O2S
Benzenecarbothioamide, N-[3-(diethylamino)propyl]-4-hydroxy-3-methoxy-
—— Ethyl 6-(bromomethyl)-4-(4-hydroxy-3-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate —— C16H19BrN2O5
Ethyl 6-(bromomethyl)-4-(4-hydroxy-3-methoxyphenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 4-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-2-(1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile —— C23H22N2O4
4-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-5-oxo-2-(1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
—— 4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-2-(1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile —— C22H20N2O3
4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-2-(1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
—— methyl 5-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-6-(1H-pyrrol-1-yl)-4H-pyran-3-carboxylate —— C21H20N2O6
methyl 5-cyano-4-(4-hydroxy-3,5-dimethoxyphenyl)-2-methyl-6-(1H-pyrrol-1-yl)-4H-pyran-3-carboxylate
—— methyl 5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-(1H-pyrrol-1-yl)-4H-pyran-3-carboxylate —— C20H18N2O5
methyl 5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-(1H-pyrrol-1-yl)-4H-pyran-3-carboxylate
—— 2-methoxy-6-({[1-methyl-2-(piperidin-1-ylmethyl)-1H-benzimidazol-5-yl]amino}methyl)phenol —— C22H28N4O2
2-methoxy-6-({[1-methyl-2-(piperidin-1-ylmethyl)-1H-benzimidazol-5-yl]amino}methyl)phenol
—— 5-Amino-7-(3-chloro-4-hydroxy-5-methoxyphenyl)-4-(4-methoxyphenyl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile 1,1-dioxide —— C22H20ClN3O5S
5-Amino-7-(3-chloro-4-hydroxy-5-methoxyphenyl)-4-(4-methoxyphenyl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile 1,1-dioxide
—— 5-[(5-bromo-2-hydroxybenzyl)amino]-1H-pyrazole-4-carbonitrile —— C11H9BrN4O
5-[(5-bromo-2-hydroxybenzyl)amino]-1H-pyrazole-4-carbonitrile
—— 5-Amino-4-(4-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile 1,1-dioxide —— C21H18FN3O4S
5-Amino-4-(4-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile 1,1-dioxide
—— 4-[(E)-1-(4-Hydroxy-3-methoxyphenyl)methylidene]-5-methyl-2-(1H-1,2,3,4-tetraazol-5-YL)-2,4-dihydro-3H-pyrazol-3-one —— C13H12N6O3
4-[(E)-1-(4-Hydroxy-3-methoxyphenyl)methylidene]-5-methyl-2-(1H-1,2,3,4-tetraazol-5-YL)-2,4-dihydro-3H-pyrazol-3-one
—— Diethyl 5,5'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2-methylthiophene-3-carboxylate) —— C24H26O8S2
Diethyl 5,5'-[(4-hydroxy-3-methoxyphenyl)methanediyl]bis(4-hydroxy-2-methylthiophene-3-carboxylate)
—— 5-Amino-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-4-(4-fluorophenyl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile 1,1-dioxide —— C21H17BrFN3O4S
5-Amino-7-(3-bromo-4-hydroxy-5-methoxyphenyl)-4-(4-fluorophenyl)-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile 1,1-dioxide
—— 2-methoxy-4-[8-(methoxymethyl)-6-methyl-3-thia-5,11,13,20-tetrazapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1,4,6,8,10,14,16,18-octaen-12-yl]phenol —— C25H22N4O3S
2-methoxy-4-[8-(methoxymethyl)-6-methyl-3-thia-5,11,13,20-tetrazapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1,4,6,8,10,14,16,18-octaen-12-yl]phenol
—— 4-[2-(2-Chloro-4-hydroxy-5-methoxy-phenyl)-vinyl]-6-trifluoromethyl-1H-pyrimidin-2-one —— C14H10ClF3N2O3
4-[2-(2-Chloro-4-hydroxy-5-methoxy-phenyl)-vinyl]-6-trifluoromethyl-1H-pyrimidin-2-one
—— (2E)-2-(1,3-benzothiazol-2-yl)-3-(4-hydroxy-3-nitrophenyl)acrylonitrile —— C16H9N3O3S
(2E)-2-(1,3-benzothiazol-2-yl)-3-(4-hydroxy-3-nitrophenyl)acrylonitrile
—— (5E)-2-(2,6-dimethylmorpholin-4-yl)-5-(3-hydroxybenzylidene)-1,3-thiazol-4(5H)-one —— C16H18N2O3S
(5E)-2-(2,6-dimethylmorpholin-4-yl)-5-(3-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
—— 5-(4-hydroxy-3,5-dimethoxybenzylidene)-1-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione —— C19H16N2O6
5-(4-hydroxy-3,5-dimethoxybenzylidene)-1-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione
—— ethyl (2E)-2-(3-bromo-4-hydroxy-5-methoxybenzylidene)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O7S
ethyl (2E)-2-(3-bromo-4-hydroxy-5-methoxybenzylidene)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2Z)-2-(4-Hydroxy-3,5-dimethoxybenzylidene)-8-methyl[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one —— C19H16N2O4S
(2Z)-2-(4-Hydroxy-3,5-dimethoxybenzylidene)-8-methyl[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— 2-[(Z)-1-(3-Hydroxy-4-methoxyphenyl)methylidene]-8-methyl[1,3]thiazolo[3,2-A][1,3]benzimidazol-3-one —— C18H14N2O3S
2-[(Z)-1-(3-Hydroxy-4-methoxyphenyl)methylidene]-8-methyl[1,3]thiazolo[3,2-A][1,3]benzimidazol-3-one
—— Thiazol-4(5H)-one, 5-(4-hydroxybenzylidene)-2-(3-methyl-1-piperidyl)- —— C16H18N2O2S
Thiazol-4(5H)-one, 5-(4-hydroxybenzylidene)-2-(3-methyl-1-piperidyl)-
—— (5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-(3-methoxyphenyl)-1,3-diazinane-2,4,6-trione —— C20H18N2O7
(5E)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-(3-methoxyphenyl)-1,3-diazinane-2,4,6-trione
—— ethyl (2E)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2-(2,3,4-trimethoxybenzylidene)-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O8S
ethyl (2E)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2-(2,3,4-trimethoxybenzylidene)-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[4-(dimethylamino)benzylidene]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H27N3O5S
ethyl (2E)-2-[4-(dimethylamino)benzylidene]-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-(3-nitrobenzylidene)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2E)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-(3-nitrobenzylidene)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-5-(1,3-benzodioxol-5-yl)-2-(2-bromo-4-hydroxy-5-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H21BrN2O7S
ethyl (2E)-5-(1,3-benzodioxol-5-yl)-2-(2-bromo-4-hydroxy-5-methoxybenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-[5-(2-Hydroxy-5-nitro-phenyl)-furan-2-ylmethylene]-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one —— C22H17N3O5
4-[5-(2-Hydroxy-5-nitro-phenyl)-furan-2-ylmethylene]-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one
—— ethyl (2E)-2-(3-hydroxybenzylidene)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H22N2O6S
ethyl (2E)-2-(3-hydroxybenzylidene)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H23BrN2O6S
ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-(2-nitrobenzylidene)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2E)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-(2-nitrobenzylidene)-3-oxo-2,3-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-3-cyclopentyl-5-[(4-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C21H20N2O2S
(5E)-3-cyclopentyl-5-[(4-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E)-6-acetyl-2-(4-hydroxy-3-methoxybenzylidene)-5-(2-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one —— C24H22N2O5S
(2E)-6-acetyl-2-(4-hydroxy-3-methoxybenzylidene)-5-(2-methoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one
—— (2Z)-2-(4-hydroxy-3-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one —— C16H9N3O4S
(2Z)-2-(4-hydroxy-3-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— ethyl (2E)-2-(4-hydroxy-3-methoxybenzylidene)-5-(2-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O6S
ethyl (2E)-2-(4-hydroxy-3-methoxybenzylidene)-5-(2-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E,5E)-3-cyclohexyl-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C23H22Br2N2O3S
(2E,5E)-3-cyclohexyl-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (2E,5E)-3-cyclopentyl-5-(3,5-dibromo-4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C21H18Br2N2O2S
(2E,5E)-3-cyclopentyl-5-(3,5-dibromo-4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (2E,5E)-3-cyclopentyl-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C22H20Br2N2O3S
(2E,5E)-3-cyclopentyl-5-(2,3-dibromo-4-hydroxy-5-methoxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (2E,5E)-5-(3,5-dibromo-4-hydroxybenzylidene)-2-(phenylimino)-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one —— C19H14Br2N2O2S
(2E,5E)-5-(3,5-dibromo-4-hydroxybenzylidene)-2-(phenylimino)-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one
—— (2E,5E)-5-(4-hydroxybenzylidene)-2-(phenylimino)-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one —— C19H16N2O2S
(2E,5E)-5-(4-hydroxybenzylidene)-2-(phenylimino)-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one
—— ethyl (2E)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H17BrN2O4S2
ethyl (2E)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-Benzyl-5-(3-bromo-4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one —— C23H17BrN2O2S
3-Benzyl-5-(3-bromo-4-hydroxybenzylidene)-2-(phenylimino)-1,3-thiazolidin-4-one
—— ethyl (2E)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H19BrN2O5S2
ethyl (2E)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21BrN2O5S
ethyl (2E)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C23H17ClN2O3S
(5Z)-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
—— ethyl (2E)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2E)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (Z)-4-(3-hydroxy-4-methoxybenzylidene)-3-methylisoxazol-5(4H)-one —— C12H11NO4
(Z)-4-(3-hydroxy-4-methoxybenzylidene)-3-methylisoxazol-5(4H)-one
—— ethyl (2E)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H25BrN2O7S
ethyl (2E)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(2,5-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E)-2-[(2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H18N2O4S2
ethyl (2E)-2-[(2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate