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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
—— (4S)-5-(4-cyclohexyl-1H-imidazol-2-yl)-6-ethyl-4-(3-fluoro-4-hydroxy-phenyl)-3,4-dihydro-1H-pyrimidin-2-one 1372148-90-7 C21H25FN4O2
(4S)-5-(4-cyclohexyl-1H-imidazol-2-yl)-6-ethyl-4-(3-fluoro-4-hydroxy-phenyl)-3,4-dihydro-1H-pyrimidin-2-one
—— 5-(2-chlorobenzyloxy)benzene-1,3-diol 1304772-15-3 C13H11ClO3
5-(2-chlorobenzyloxy)benzene-1,3-diol
—— 5-(3-chlorobenzyloxy)benzene-1,3-diol 1304772-17-5 C13H11ClO3
5-(3-chlorobenzyloxy)benzene-1,3-diol
—— 2,5-dibromo-4-nitro-phenol 76362-02-2 C6H3Br2NO3
2,5-dibromo-4-nitro-phenol
—— Methyl-(5-hydroxy-2.4-dimethyl-phenyl)-aether 81633-94-5 C9H12O2
Methyl-(5-hydroxy-2.4-dimethyl-phenyl)-aether
—— 5-tert-butyl-2-hydroxyl-3-nitro-benzonitrile 85943-76-6 C11H12N2O3
5-tert-butyl-2-hydroxyl-3-nitro-benzonitrile
—— (S)P[N(Me)N=CH-C6H4-o-OH]3 153687-84-4 C24H27N6O3PS
(S)P[N(Me)N=CH-C6H4-o-OH]3
—— 3-fluoro-2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one 1341125-91-4 C14H13FO3
3-fluoro-2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one
—— 3-chloro-2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one 1341125-92-5 C14H13ClO3
3-chloro-2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one
—— 2-(4-hydroxyphenyl)-4-oxo-1-oxaspiro[4.4]non-2-ene-3-carboxylic acid amide 1341125-96-9 C15H15NO4
2-(4-hydroxyphenyl)-4-oxo-1-oxaspiro[4.4]non-2-ene-3-carboxylic acid amide
—— 3-bromo-2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one 1341125-93-6 C14H13BrO3
3-bromo-2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one
—— 2-(4-hydroxyphenyl)-4-oxo-1-oxaspiro[4.4]non-2-ene-3-carbonitrile 1341125-95-8 C15H13NO3
2-(4-hydroxyphenyl)-4-oxo-1-oxaspiro[4.4]non-2-ene-3-carbonitrile
—— 2-(4-hydroxyphenyl)-3-iodo-1-oxaspiro[4.4]non-2-en-4-one 1341125-94-7 C14H13IO3
2-(4-hydroxyphenyl)-3-iodo-1-oxaspiro[4.4]non-2-en-4-one
—— 2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one 1341224-10-9 C14H14O3
2-(4-hydroxyphenyl)-1-oxaspiro[4.4]non-2-en-4-one
—— 1,4-bis-(4-hydroxy-trityl)-benzene 58462-03-6 C44H34O2
1,4-bis-(4-hydroxy-trityl)-benzene
—— 2-((E)-prop-1-enyl)-6-methylphenol 927822-08-0 C10H12O
2-((E)-prop-1-enyl)-6-methylphenol
—— 2-chloro-6-nitro-4-(trifluoromethyl)phenol 69741-64-6 C7H3ClF3NO3
2-chloro-6-nitro-4-(trifluoromethyl)phenol
—— 1-carbothioamide-4,5-dihydro-3-methyl-5-(4-hydroxyphenyl)-1H-pyrazole 1107065-12-2 C11H13N3OS
1-carbothioamide-4,5-dihydro-3-methyl-5-(4-hydroxyphenyl)-1H-pyrazole
—— N-benzyl-5-(4-hydroxyphenyl)-3-methyl-4,5-dihydropyrazole-1-carbothioamide 1107065-25-7 C18H19N3OS
N-benzyl-5-(4-hydroxyphenyl)-3-methyl-4,5-dihydropyrazole-1-carbothioamide
—— 2,5-Dibutyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1289448-16-3 C20H33BO3
2,5-Dibutyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— (1R,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate 1338384-86-3 C18H27NO8S
(1R,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate
—— (1R,2'R)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate 1338384-84-1 C18H27NO8S
(1R,2'R)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate
—— (1S,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate 1338384-87-4 C18H27NO8S
(1S,2'S)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate
—— (3E,5E)-3-(4-hydroxy-3-methoxybenzylidene)-5-[(1H-indol-3-yl)methylene]-1-methylpiperidin-4-one 1370032-21-5 C23H22N2O3
(3E,5E)-3-(4-hydroxy-3-methoxybenzylidene)-5-[(1H-indol-3-yl)methylene]-1-methylpiperidin-4-one
—— <i>N</i><sup>2</sup>,<i>N</i><sup>4</sup>-disalicyloyl-formohydrazidine 98307-51-8 C15H14N4O4
<i>N</i><sup>2</sup>,<i>N</i><sup>4</sup>-disalicyloyl-formohydrazidine
—— 4,5-Dihydroxybenzocyclobutene 4082-31-9 C8H8O2
4,5-Dihydroxybenzocyclobutene
—— 2-(3-isopropenyl-4,5-dimethoxyphenyl)ethanol 181016-79-5 C13H18O3
2-(3-isopropenyl-4,5-dimethoxyphenyl)ethanol
—— 2-(3-isopropyl-4,5-dimethoxyphenyl)ethanol 181016-80-8 C13H20O3
2-(3-isopropyl-4,5-dimethoxyphenyl)ethanol
—— 3-Anisyl-5-(2-hydroxy-5-methylphenyl)-Δ<sup>2</sup>-pyrazoline 107095-35-2 C17H18N2O2
3-Anisyl-5-(2-hydroxy-5-methylphenyl)-Δ<sup>2</sup>-pyrazoline
—— ardisiaquinone F 99621-86-0 C30H42O6
ardisiaquinone F
—— 5-isohexyl-resorcinol 860504-71-8 C12H18O2
5-isohexyl-resorcinol
—— (2,3-dihydroxybenzylidene)-2-hydroxybenzohydrazide —— C14H12N2O4
(2,3-dihydroxybenzylidene)-2-hydroxybenzohydrazide
—— 1,3-dihydroxy-2-methyl-5-(7-bromoheptyl)benzene 219630-94-1 C14H21BrO2
1,3-dihydroxy-2-methyl-5-(7-bromoheptyl)benzene
—— 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxyphenyl)-8-Z-hexadecene 219630-90-7 C30H42O6
1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxyphenyl)-8-Z-hexadecene
—— 1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene 219630-97-4 C31H44O6
1-(3,6-dimethoxy-1,4-benzoquinon-2-yl)-16-(3,5-dihydroxy-4-methylphenyl)-8-Z-hexadecene
—— ardisiaquinone E 99621-87-1 C29H40O6
ardisiaquinone E
—— 1-bromo-7-(3,5-dihydroxyphenyl)heptane 219630-86-1 C13H19BrO2
1-bromo-7-(3,5-dihydroxyphenyl)heptane
—— 6-[(furan-2-ylmethylamino)methylidene]cyclohexa-2,4-dien-1-one 76152-10-8 C12H11NO2
6-[(furan-2-ylmethylamino)methylidene]cyclohexa-2,4-dien-1-one
—— malon-di-<(p-hydroxy)benzylidene amino>amide 92514-61-9 C17H16N4O4
malon-di-<(p-hydroxy)benzylidene amino>amide
—— 4-(3-fluoro-4-hydroxy-phenyl)-butyric acid 588-25-0 C10H11FO3
4-(3-fluoro-4-hydroxy-phenyl)-butyric acid
—— 3,5-dimethyl-2,6-dinitrophenol 99584-19-7 C8H8N2O5
3,5-dimethyl-2,6-dinitrophenol
—— 4-[(2,4-Diamino-6-propylpyrimidin-5-yl)methyl]-2,6-dimethoxyphenol 73576-45-1 C16H22N4O3
4-[(2,4-Diamino-6-propylpyrimidin-5-yl)methyl]-2,6-dimethoxyphenol
—— 55380-55-7 C21H30O3
—— 3-[(2-hydroxy-3-methoxybenzylidene)hydrazo]-1,3-dihydroindol-2-one 326884-73-5 C16H13N3O3
3-[(2-hydroxy-3-methoxybenzylidene)hydrazo]-1,3-dihydroindol-2-one
—— ethyl(4,5-dimethoxy-2-hydroxyphenyl)acetate 76322-30-0 C12H16O5
ethyl(4,5-dimethoxy-2-hydroxyphenyl)acetate
—— 5-[4-(1,2-cis-hexen-1-yl)tetrahydro-2H-pyran-4-yl]resorcinol 1605281-06-8 C17H24O3
5-[4-(1,2-cis-hexen-1-yl)tetrahydro-2H-pyran-4-yl]resorcinol
—— 4-(3,5-dihydroxyphenyl)tetrahydro-2H-pyran-4-carbonitrile 1605281-02-4 C12H13NO3
4-(3,5-dihydroxyphenyl)tetrahydro-2H-pyran-4-carbonitrile
—— 3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 187877-87-8 C13H17NO4
3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
—— 3-(3-bromo-4-hydroxyphenyl)-2-oxo-N-(2-sulfanylethyl)propanamide 1356929-90-2 C11H12BrNO3S
3-(3-bromo-4-hydroxyphenyl)-2-oxo-N-(2-sulfanylethyl)propanamide
—— (2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydrazinylidenepropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydrazinylidenepropanamide 1356929-94-6 C22H26Br2N6O4S2
(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydrazinylidenepropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydrazinylidenepropanamide