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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-Methyl-4-pentylbenzene-1,3,5-triol;2,4,6-trimethylbenzene-1,3,5-triol —— C21H30O6
2-Methyl-4-pentylbenzene-1,3,5-triol;2,4,6-trimethylbenzene-1,3,5-triol
—— Amino 2-(4-hydroxyphenyl)propanoate —— C9H11NO3
Amino 2-(4-hydroxyphenyl)propanoate
—— 2,3,4,6-Tetrachlorophenol;sulfate —— C6H2Cl4O5S-2
2,3,4,6-Tetrachlorophenol;sulfate
—— 4-Methoxyphenol;phosphate —— C7H8O6P-3
4-Methoxyphenol;phosphate
—— methyl (2Z)-2-(hydroxyamino)-2-[3-[(2S,5R)-5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-4-(1H-imidazol-2-yl)-1,3-dithian-2-yl]indol-2-ylidene]acetate —— C25H24N4O6S2
methyl (2Z)-2-(hydroxyamino)-2-[3-[(2S,5R)-5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-4-(1H-imidazol-2-yl)-1,3-dithian-2-yl]indol-2-ylidene]acetate
—— (2-Methoxypyridin-4-yl)methyl 7-[(3,5-difluoro-4-hydroxyphenyl)methyl]-9-methyl-6,8-dioxo-1,4-dihydropyrazino[1,2-c]pyrimidine-3-carboxylate —— C23H20F2N4O6
(2-Methoxypyridin-4-yl)methyl 7-[(3,5-difluoro-4-hydroxyphenyl)methyl]-9-methyl-6,8-dioxo-1,4-dihydropyrazino[1,2-c]pyrimidine-3-carboxylate
—— [5-[2-[4-(1H-indol-3-ylmethyldiazenyl)-6-morpholin-4-ylpyrimidin-2-yl]oxyethyl]-2-methoxyphenyl]methanol —— C27H30N6O4
[5-[2-[4-(1H-indol-3-ylmethyldiazenyl)-6-morpholin-4-ylpyrimidin-2-yl]oxyethyl]-2-methoxyphenyl]methanol
—— 6-[4-hydroxy-3-(hydroxymethyl)-5-methoxyphenyl]-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid —— C14H16N2O6
6-[4-hydroxy-3-(hydroxymethyl)-5-methoxyphenyl]-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylic acid
—— 1H-indeno[1,2-b]pyridin-9-ol —— C12H9NO
1H-indeno[1,2-b]pyridin-9-ol
—— 3-Methoxy-2-pentadeca-1,3,5-trien-5-ylphenol —— C22H32O2
3-Methoxy-2-pentadeca-1,3,5-trien-5-ylphenol
—— tert-butyl 6-(4-hydroxy-3-methoxy-5-methylphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate —— C18H24N2O5
tert-butyl 6-(4-hydroxy-3-methoxy-5-methylphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate
—— Ethane;(2-methoxy-2-oxoethyl) propanoate;phenol —— C14H22O5
Ethane;(2-methoxy-2-oxoethyl) propanoate;phenol
—— 4-[2-[2-(4-Hydroxy-2,6-dimethoxyphenyl)ethynylsulfinylmethylsulfinyl]ethyl]-3,5-dimethoxyphenol —— C21H24O8S2
4-[2-[2-(4-Hydroxy-2,6-dimethoxyphenyl)ethynylsulfinylmethylsulfinyl]ethyl]-3,5-dimethoxyphenol
—— ethyl 7-amino-6-cyano-8-(4-hydroxy-3-methoxybenzylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-8H-pyrrolo[2,1-c][1,4]thiazine-1-carboxylate —— C26H23N3O7S
ethyl 7-amino-6-cyano-8-(4-hydroxy-3-methoxybenzylidene)-3-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-8H-pyrrolo[2,1-c][1,4]thiazine-1-carboxylate
—— 2-Anilino-5-chlorophenol —— C12H10ClNO
2-Anilino-5-chlorophenol
—— (2R,3R,4R)-3-[5-[5-chloro-3-(1,3-dioxan-2-yl)-2-hydroxy-6-methoxy-4-methylphenyl]-3-methylpenta-1,3-dienyl]-2,3,4-trimethylcyclohexan-1-one —— C27H37ClO5
(2R,3R,4R)-3-[5-[5-chloro-3-(1,3-dioxan-2-yl)-2-hydroxy-6-methoxy-4-methylphenyl]-3-methylpenta-1,3-dienyl]-2,3,4-trimethylcyclohexan-1-one
—— 5-[Hydroxy(propyl)amino]-2-methylphenol —— C10H15NO2
5-[Hydroxy(propyl)amino]-2-methylphenol
—— (E)-3-(2-hydroxy-5-methylanilino)-1-(5-methylfuran-2-yl)but-2-en-1-one —— C16H17NO3
(E)-3-(2-hydroxy-5-methylanilino)-1-(5-methylfuran-2-yl)but-2-en-1-one
—— 4-Amino-2-(4-hydroxy-3-methylanilino)phenol —— C13H14N2O2
4-Amino-2-(4-hydroxy-3-methylanilino)phenol
—— ethane;N-ethylprop-2-enamide;phenol;propane —— C45H79N3O6
ethane;N-ethylprop-2-enamide;phenol;propane
—— 6-[(1E)-2-(5-Bromo-2-hydroxy-3-methylphenyl)ethenyl]-5-nitropyrimidine-2,4-diol —— C13H10BrN3O5
6-[(1E)-2-(5-Bromo-2-hydroxy-3-methylphenyl)ethenyl]-5-nitropyrimidine-2,4-diol
—— (2Z)-1-(2,4-dihydroxyphenyl)-2-(4-phenyl-1H-1,2,4-triazol-5-ylidene)ethanone —— C16H13N3O3
(2Z)-1-(2,4-dihydroxyphenyl)-2-(4-phenyl-1H-1,2,4-triazol-5-ylidene)ethanone
—— propan-2-yl 6-(3-chloro-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate —— C16H19ClN2O5
propan-2-yl 6-(3-chloro-4-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate
—— (5Z)-5-(2-hydroxybenzylidene)-2-(3-methylpiperidin-1-yl)-1,3-thiazol-4(5H)-one —— C16H18N2O2S
(5Z)-5-(2-hydroxybenzylidene)-2-(3-methylpiperidin-1-yl)-1,3-thiazol-4(5H)-one
—— (5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(1,1-dioxothiolan-3-yl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H14BrNO5S3
(5E)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-(1,1-dioxothiolan-3-yl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-Cyclopentyl-2-(4-hydroxyphenyl)propanoic acid —— C14H18O3
2-Cyclopentyl-2-(4-hydroxyphenyl)propanoic acid
—— 6-Methylideneinden-5-ol —— C10H8O
6-Methylideneinden-5-ol
—— 5-Hydroxy-4-[hydroxy(methoxy)methyl]-2-(4-hydroxyphenoxy)hexan-3-one —— C14H20O6
5-Hydroxy-4-[hydroxy(methoxy)methyl]-2-(4-hydroxyphenoxy)hexan-3-one
—— 3,3-dimethylbutan-2-yl 6-[4-hydroxy-3-(hydroxymethyl)-5-methoxyphenyl]-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate —— C20H28N2O6
3,3-dimethylbutan-2-yl 6-[4-hydroxy-3-(hydroxymethyl)-5-methoxyphenyl]-4-methyl-2-oxo-5,6-dihydro-1H-pyrimidine-5-carboxylate
—— 4-[5-[(2-Hydroxy-6-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C15H15NO5S2
4-[5-[(2-Hydroxy-6-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
—— 3-[1-[1-[Bis(trihydroxymethyl)amino]-3-methylbutyl]cyclobutyl]-6-chlorobenzene-1,2,4,5-tetrol —— C17H26ClNO10
3-[1-[1-[Bis(trihydroxymethyl)amino]-3-methylbutyl]cyclobutyl]-6-chlorobenzene-1,2,4,5-tetrol
—— 4-[[Dihydroxy(trihydroxysilyloxy)silyl]oxy-[[[2-hydroperoxyperoxysulfanyl-3-hydroperoxysulfonyl-5-sulfooxy-6-(trioxidanylsulfanylmethyl)oxan-4-yl]oxysulfonyloxy-hydroxy-(hydroxy-methyl-trihydroxysilyloxysilyl)oxysilyl]peroxy-dihydroxysilyl]oxy-hydroxysilyl]oxysulfonyloxy-2-[5-(dimethylamino)-4-hydroxy-2-methylphenyl]-5-sulfooxy-6-(sulfooxymethyl)oxane-2,3-disulfonoperoxoic acid —— C22H49NO62S10Si7
4-[[Dihydroxy(trihydroxysilyloxy)silyl]oxy-[[[2-hydroperoxyperoxysulfanyl-3-hydroperoxysulfonyl-5-sulfooxy-6-(trioxidanylsulfanylmethyl)oxan-4-yl]oxysulfonyloxy-hydroxy-(hydroxy-methyl-trihydroxysilyloxysilyl)oxysilyl]peroxy-dihydroxysilyl]oxy-hydroxysilyl]oxysulfonyloxy-2-[5-(dimethylamino)-4-hydroxy-2-methylphenyl]-5-sulfooxy-6-(sulfooxymethyl)oxane-2,3-disulfonoperoxoic acid
—— benzene;ethane;phenol;propane —— C40H68O2
benzene;ethane;phenol;propane
—— 4-[[4,6-Bis(octylsulfanyl)-1,3,5-triazin-2-yl]amino]-2,6-dimethylphenol;2,4,6-trimethylphenol —— C36H56N4O2S2
4-[[4,6-Bis(octylsulfanyl)-1,3,5-triazin-2-yl]amino]-2,6-dimethylphenol;2,4,6-trimethylphenol
—— (1,2,2,6,6-Pentamethylpiperidin-4-yl)methyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate —— C44H70N2O6
(1,2,2,6,6-Pentamethylpiperidin-4-yl)methyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate
—— (4E)-4-[(5-bromo-2-hydroxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one —— C17H14BrN3O2
(4E)-4-[(5-bromo-2-hydroxyanilino)methylidene]-5-methyl-2-phenylpyrazol-3-one
—— (5E)-3-(butan-2-yl)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione —— C15H16ClNO4S
(5E)-3-(butan-2-yl)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
—— 4-[[[6-(4-Chloroanilino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]diazenyl]methyl]-2-methoxyphenol —— C18H14ClN7O3
4-[[[6-(4-Chloroanilino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]diazenyl]methyl]-2-methoxyphenol
—— ethyl (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-nitroanilino)-4-oxothiophene-3-carboxylate —— C21H18N2O7S
ethyl (5Z)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-nitroanilino)-4-oxothiophene-3-carboxylate
—— 2-Methoxy-5-[[(7-methylthieno[3,2-d]pyrimidin-2-yl)diazenyl]methyl]phenol —— C15H14N4O2S
2-Methoxy-5-[[(7-methylthieno[3,2-d]pyrimidin-2-yl)diazenyl]methyl]phenol
—— (5E)-3-(butan-2-yl)-5-(3-chloro-4-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione —— C14H14ClNO3S
(5E)-3-(butan-2-yl)-5-(3-chloro-4-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione
—— 5-Bromo-1-(4-hydroxyphenyl)-3,4-dihydropyridin-2-one —— C11H10BrNO2
5-Bromo-1-(4-hydroxyphenyl)-3,4-dihydropyridin-2-one
—— 2-Methoxy-5-[[[7-methyl-6-(2-phenylethenyl)thieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]phenol —— C23H20N4O2S
2-Methoxy-5-[[[7-methyl-6-(2-phenylethenyl)thieno[3,2-d]pyrimidin-4-yl]diazenyl]methyl]phenol
—— 4-Ethoxy-3-[1-(2-hydroxyphenoxy)ethyl]phenol —— C16H18O4
4-Ethoxy-3-[1-(2-hydroxyphenoxy)ethyl]phenol
—— 2-[4-[(3-fluorophenyl)methoxy]phenyl]ethyl N-methylcarbamate —— C17H18FNO3
2-[4-[(3-fluorophenyl)methoxy]phenyl]ethyl N-methylcarbamate
—— ethyl (2E)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H24N2O5S2
ethyl (2E)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-(1-Benzofuran-2-yl)-1-(2-hydroxy-5-methoxyphenyl)-2-propen-1-one —— C18H14O4
3-(1-Benzofuran-2-yl)-1-(2-hydroxy-5-methoxyphenyl)-2-propen-1-one
—— 3,5,13,15-Tetrahydroxytricyclo[8.3.1.12,6]pentadeca-1(13),2,4,6(15),8,10(14),11-heptaen-7-one —— C15H10O5
3,5,13,15-Tetrahydroxytricyclo[8.3.1.12,6]pentadeca-1(13),2,4,6(15),8,10(14),11-heptaen-7-one
—— 9-(5-Bromo-4-fluoro-2-hydroxyphenyl)-5,13-dioxa-2-azatricyclo[8.4.0.03,8]tetradeca-1,3(8)-diene-7,11-dione —— C17H13BrFNO5
9-(5-Bromo-4-fluoro-2-hydroxyphenyl)-5,13-dioxa-2-azatricyclo[8.4.0.03,8]tetradeca-1,3(8)-diene-7,11-dione
—— (5E)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H16N2O5S2
(5E)-5-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one