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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
—— N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[3-(trifluoromethyl)phenoxy]acetamide —— C16H13F3N2O5
N-[(2-hydroxy-5-nitrophenyl)methyl]-2-[3-(trifluoromethyl)phenoxy]acetamide
—— 2-(6,7-dimethyl-1-benzofuran-3-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C19H18N2O5
2-(6,7-dimethyl-1-benzofuran-3-yl)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 3-(4-fluorophenyl)sulfanyl-N-[(2-hydroxy-5-nitrophenyl)methyl]propanamide —— C16H15FN2O4S
3-(4-fluorophenyl)sulfanyl-N-[(2-hydroxy-5-nitrophenyl)methyl]propanamide
—— 2-(2-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H13FN2O5
2-(2-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 2-(2-bromo-4-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide —— C15H12BrFN2O5
2-(2-bromo-4-fluorophenoxy)-N-[(2-hydroxy-5-nitrophenyl)methyl]acetamide
—— 4-[3-(piperazin-1-ylmethyl)furan-2-yl]phenol —— C15H18N2O2
4-[3-(piperazin-1-ylmethyl)furan-2-yl]phenol
—— (Z)-3-(3-hydroxy-4-methoxyphenyl)-2-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]prop-2-enenitrile —— C18H11F3N2O2S
(Z)-3-(3-hydroxy-4-methoxyphenyl)-2-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]prop-2-enenitrile
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-hydroxybenzamide —— C15H13BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-3-hydroxybenzamide
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-ethylbenzamide —— C17H17BrN2O3
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-4-ethylbenzamide
—— 4-ethyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide —— C17H18N2O3
4-ethyl-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— 2-methoxy-5-[(Z)-[(2,3,5,6-tetrafluoropyridin-4-yl)hydrazinylidene]methyl]phenol —— C13H9F4N3O2
2-methoxy-5-[(Z)-[(2,3,5,6-tetrafluoropyridin-4-yl)hydrazinylidene]methyl]phenol
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-cyanophenoxy)acetamide —— C17H14BrN3O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2-(2-cyanophenoxy)acetamide
—— methyl (2S)-2-(3-chloro-4-methylanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate —— C19H19ClF3NO5
methyl (2S)-2-(3-chloro-4-methylanilino)-3,3,3-trifluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)propanoate
—— ethyl (2Z,5R)-2-[[2-[2-(benzylamino)-2-oxoethoxy]phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H31N3O7S
ethyl (2Z,5R)-2-[[2-[2-(benzylamino)-2-oxoethoxy]phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-[(2R)-1-methoxypropan-2-yl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H16BrNO4S2
(5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-[(2R)-1-methoxypropan-2-yl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(3-methoxypropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H17NO4S2
(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(3-methoxypropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-morpholin-4-ylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O4S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-morpholin-4-ylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(2-morpholin-4-ylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O4S2
(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-3-(2-morpholin-4-ylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H19ClN2O3S2
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-[(2S)-1-methoxypropan-2-yl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H16BrNO4S2
(5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-[(2S)-1-methoxypropan-2-yl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-3-cyclopropyl-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H13NO3S2
(5E)-3-cyclopropyl-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (4S)-5-cyano-6-[2-(4-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4S)-5-cyano-6-[2-(4-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(4-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4R)-5-cyano-6-[2-(4-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one —— C17H16N2O3S
(Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
—— (3E)-6-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one —— C17H13ClO3S
(3E)-6-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one
—— (3E)-6-chloro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]thiochromen-4-one —— C18H15ClO4S
(3E)-6-chloro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]thiochromen-4-one
—— (Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-N-(3-hydroxy-4-methoxyphenyl)prop-2-enamide —— C17H17N3O3S
(Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-N-(3-hydroxy-4-methoxyphenyl)prop-2-enamide
—— (5E)-2-[2-(5-bromo-2-oxoindol-3-yl)hydrazinyl]-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-1,3-thiazol-4-one —— C18H9BrN6O7S
(5E)-2-[2-(5-bromo-2-oxoindol-3-yl)hydrazinyl]-5-[(2-hydroxy-3,5-dinitrophenyl)methylidene]-1,3-thiazol-4-one
—— [(4S,5S,6S)-4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinan-5-yl]-thiophen-2-ylmethanone —— C18H17F3N2O5S2
[(4S,5S,6S)-4-hydroxy-6-(4-hydroxy-3,5-dimethoxyphenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinan-5-yl]-thiophen-2-ylmethanone
—— (3E)-8-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,1-dioxothiochromen-4-one —— C18H15FO6S
(3E)-8-fluoro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,1-dioxothiochromen-4-one
—— (3E)-8-fluoro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one —— C17H13FO3S
(3E)-8-fluoro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one
—— (5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-(2-ethoxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H16BrNO4S2
(5Z)-5-[(2-bromo-5-hydroxy-4-methoxyphenyl)methylidene]-3-(2-ethoxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (5E)-2-anilino-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxofuran-3-carboxylate —— C21H18ClNO6
ethyl (5E)-2-anilino-5-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxofuran-3-carboxylate
—— 3-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile —— C15H13N3O3
3-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile
—— (5E)-3-ethyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C21H22N2O2S
(5E)-3-ethyl-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-ethyl-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C19H17ClN2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-3-ethyl-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-2-(4-chlorophenyl)imino-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H17ClN2O3S
(5E)-2-(4-chlorophenyl)imino-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-3-ethyl-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C23H24N2O3S
(5E)-3-ethyl-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C22H23ClN2O2S
(5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— prop-2-enyl (4R)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate —— C26H24ClN3O5S
prop-2-enyl (4R)-6-[2-(3-chloroanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
—— (5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-3-methyl-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H15BrN2O2S
(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-3-methyl-2-(2-methylphenyl)imino-1,3-thiazolidin-4-one
—— (5E)-2-(3-chlorophenyl)imino-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H17ClN2O3S
(5E)-2-(3-chlorophenyl)imino-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-2-(3-chlorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H15ClN2O3S
(5E)-2-(3-chlorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(2,4-difluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C21H20F2N2O3S
(5E)-2-(2,4-difluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— (5E)-2-(2,4-difluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one —— C22H22F2N2O2S
(5E)-2-(2,4-difluorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-(2-methylpropyl)-1,3-thiazolidin-4-one
—— (5E)-2-(2-chlorophenyl)imino-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H17ClN2O3S
(5E)-2-(2-chlorophenyl)imino-3-ethyl-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C19H17ClN2O2S
(5E)-2-(2-chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(2,4-difluorophenyl)imino-3-ethyl-1,3-thiazolidin-4-one —— C18H13ClF2N2O2S
(5E)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(2,4-difluorophenyl)imino-3-ethyl-1,3-thiazolidin-4-one
—— (5E)-2-(2,4-difluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one —— C18H14F2N2O3S
(5E)-2-(2,4-difluorophenyl)imino-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-3-methyl-1,3-thiazolidin-4-one
—— (5E)-2-(2,4-difluorophenyl)imino-3-ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H16F2N2O3S
(5E)-2-(2,4-difluorophenyl)imino-3-ethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one