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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-[5-[(3-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O4S2
2-[5-[(3-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— [(Benzylamino)-(4-hydroxy-3-methoxyphenyl)methyl]-(2-phenylethyl)phosphinic acid —— C23H26NO4P
[(Benzylamino)-(4-hydroxy-3-methoxyphenyl)methyl]-(2-phenylethyl)phosphinic acid
—— 2-Methoxy-5-[[(5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C19H17N5O2
2-Methoxy-5-[[(5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C20H20N2O5S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(2-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C20H17FN2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(2-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(4-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H17FN2O5S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(4-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 4-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-[2-(3,4-dihydroxyphenyl)ethyl]butanamide —— C22H22N2O4S2
4-(5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-N-[2-(3,4-dihydroxyphenyl)ethyl]butanamide
—— 2-Methoxy-5-[[(7-methoxy-5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C20H19N5O3
2-Methoxy-5-[[(7-methoxy-5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[2,4-dioxo-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]propanamide —— C19H18N2O5S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[2,4-dioxo-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(2-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide —— C21H19FN2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(2-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(4-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C20H17FN2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(4-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— 4-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide —— C21H22N2O5S2
4-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(2-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H17FN2O5S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(2-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 2-(5-cinnamylidene-2,4-dioxo-1,3-thiazolidin-3-yl)-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C22H20N2O5S
2-(5-cinnamylidene-2,4-dioxo-1,3-thiazolidin-3-yl)-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(2-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C22H22N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(2-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(4-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C21H19FN2O5S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(4-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— 2-[5-[(3-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O5S
2-[5-[(3-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(2-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O5S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(2-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[3-(furan-2-yl)prop-2-enylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C21H20N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[3-(furan-2-yl)prop-2-enylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide —— C19H18N2O5S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O4S2
5-[(3,4-Dihydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— [(Benzylamino)-(2-hydroxyphenyl)methyl]-(2-phenylethyl)phosphinic acid —— C22H24NO3P
[(Benzylamino)-(2-hydroxyphenyl)methyl]-(2-phenylethyl)phosphinic acid
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-(furan-2-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C18H16N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-(furan-2-ylmethylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[5-[(1-methylpyrrol-2-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C21H23N3O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[5-[(1-methylpyrrol-2-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— 3-[5-[(2-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide —— C21H19ClN2O5S
3-[5-[(2-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[(3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C22H22N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[5-[(3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— 2-(1-Adamantyl)-4-chloro-5-(5-chloro-2-hydroxyanilino)pyridazin-3-one —— C20H21Cl2N3O2
2-(1-Adamantyl)-4-chloro-5-(5-chloro-2-hydroxyanilino)pyridazin-3-one
—— 8-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C22H21N3O3S
8-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— 2-methoxy-5-[[(9-methoxy-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C19H17N5O3
2-methoxy-5-[[(9-methoxy-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— 2-methoxy-5-[[(7-methoxy-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C19H17N5O3
2-methoxy-5-[[(7-methoxy-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— 2-methoxy-5-[[(8-methoxy-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C19H17N5O3
2-methoxy-5-[[(8-methoxy-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— 3-(4-fluorophenyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C21H18FN3O3S
3-(4-fluorophenyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— 2-Methoxy-5-[[(9-methoxy-5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C20H19N5O3
2-Methoxy-5-[[(9-methoxy-5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— 2-Methoxy-5-[[(8-methoxy-5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol —— C20H19N5O3
2-Methoxy-5-[[(8-methoxy-5-methylpyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]phenol
—— 5-[[(8-fluoro-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C18H14FN5O2
5-[[(8-fluoro-5H-pyrimido[5,4-b]indol-4-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— 3-benzyl-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C22H20BrN3O3S
3-benzyl-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— 2-[[(5-Amino-6-chloropyrimidin-4-yl)hydrazinylidene]methyl]-6-methoxyphenol —— C12H12ClN5O2
2-[[(5-Amino-6-chloropyrimidin-4-yl)hydrazinylidene]methyl]-6-methoxyphenol
—— 2-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-phenyl-3H-thieno[2,3-d]pyrimidin-4-one —— C21H16N2O3S
2-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-phenyl-3H-thieno[2,3-d]pyrimidin-4-one
—— 4-Bromo-2-[3-(2-chlorophenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]phenol —— C14H10BrClN2O2
4-Bromo-2-[3-(2-chlorophenyl)-2,5-dihydro-1,2,4-oxadiazol-5-yl]phenol
—— 4-(1,3-Benzothiazol-2-yl)-5-(2-bromo-5-hydroxy-4-methoxyphenyl)pent-4-enoic acid —— C19H16BrNO4S
4-(1,3-Benzothiazol-2-yl)-5-(2-bromo-5-hydroxy-4-methoxyphenyl)pent-4-enoic acid
—— 2-Methoxy-5-[2-(5-phenyl-1,3-benzoxazol-2-yl)ethenyl]phenol —— C22H17NO3
2-Methoxy-5-[2-(5-phenyl-1,3-benzoxazol-2-yl)ethenyl]phenol
—— 5-Bromo-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-methylindol-2-one —— C17H14BrNO3
5-Bromo-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-1-methylindol-2-one
—— 4-[2-(5,6-Dimethyl-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C18H17NO2S
4-[2-(5,6-Dimethyl-1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— 2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C20H20N2O4S
2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— 2-[1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one —— C22H17ClN2O3S
2-[1-chloro-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-6-methyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one
—— 2-methoxy-4-[5-(4-methylphenyl)-1,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl]phenol —— C18H17N5O2
2-methoxy-4-[5-(4-methylphenyl)-1,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl]phenol
—— 10-[(3-Hydroxy-4-methoxyphenyl)methylidene]-4-phenyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one —— C23H18N2O3S
10-[(3-Hydroxy-4-methoxyphenyl)methylidene]-4-phenyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one
—— 2-methoxy-4-(2-phenyl-3H-[1,2,4]triazolo[1,5-d][1,2,4]triazin-7-yl)phenol —— C17H15N5O2
2-methoxy-4-(2-phenyl-3H-[1,2,4]triazolo[1,5-d][1,2,4]triazin-7-yl)phenol
—— 2-[[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-[(4-methylphenyl)sulfanylmethyl]triazole-4-carbonyl]hydrazinylidene]methyl]-5-hydroxyphenolate —— C20H18N8O4S
2-[[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-[(4-methylphenyl)sulfanylmethyl]triazole-4-carbonyl]hydrazinylidene]methyl]-5-hydroxyphenolate