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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
—— (E)-3-(4-hydroxybenzylidene)dihydro-2(3H)-furanone 102271-69-2 C11H10O3
(E)-3-(4-hydroxybenzylidene)dihydro-2(3H)-furanone
—— (2S)-4-(3,4-dihydroxyphenyl)-2-butanol 259727-11-2 C10H14O3
(2S)-4-(3,4-dihydroxyphenyl)-2-butanol
—— 2,3,5-Trideuterio-4-ethyl-6-methoxyphenol 1416507-84-0 C9H12O2
2,3,5-Trideuterio-4-ethyl-6-methoxyphenol
—— N-Boc-N-[2-(2-bromo-5-hydroxy-phenyl)ethyl]amine 1273546-87-4 C13H18BrNO3
N-Boc-N-[2-(2-bromo-5-hydroxy-phenyl)ethyl]amine
—— (R)-6-[(S)-2-hydroxy-4-(2,5-dibromo-4-hydroxyphenyl)butyl]-5,6-dihydropyran-2-one 1443115-28-3 C15H16Br2O4
(R)-6-[(S)-2-hydroxy-4-(2,5-dibromo-4-hydroxyphenyl)butyl]-5,6-dihydropyran-2-one
—— (R)-6-[(S)-2-hydroxy-4-(3,4-dihydroxyphenyl)butyl]-5,6-dihydropyran-2-one 1443115-27-2 C15H18O5
(R)-6-[(S)-2-hydroxy-4-(3,4-dihydroxyphenyl)butyl]-5,6-dihydropyran-2-one
—— 2,4-dinitro-6-trifluoromethylphenol 54715-54-7 C7H3F3N2O5
2,4-dinitro-6-trifluoromethylphenol
—— N'-(2-hydroxybenzylidene)stearohydrazide 6343-99-3 C25H42N2O2
N'-(2-hydroxybenzylidene)stearohydrazide
—— 2-(1-methoxycarbonyloxy-2-propynyl)phenol 680220-89-7 C11H10O4
2-(1-methoxycarbonyloxy-2-propynyl)phenol
—— (2-Hydroxy-5-methyl-phenyl)-tetramethylene-sulphonium perchlorate 66669-64-5 C11H15OS*ClO4
(2-Hydroxy-5-methyl-phenyl)-tetramethylene-sulphonium perchlorate
—— 2-(2-Hydroxyphenyl)-3-aza-5-amino-5-methylhexane 158328-26-8 C12H20N2O
2-(2-Hydroxyphenyl)-3-aza-5-amino-5-methylhexane
—— 2-amino-2-(3-fluoro-4-hydroxyphenyl)acetonitrile 1208237-24-4 C8H7FN2O
2-amino-2-(3-fluoro-4-hydroxyphenyl)acetonitrile
—— 2-Hydroxy-5-methoxy-4-(2-(trimethylsilyl)ethoxy)benzaldehyde 828933-87-5 C13H20O4Si
2-Hydroxy-5-methoxy-4-(2-(trimethylsilyl)ethoxy)benzaldehyde
—— bis(4-hydroxyphenyl)ethylmethylsilane 906813-24-9 C15H18O2Si
bis(4-hydroxyphenyl)ethylmethylsilane
—— 2-Ethoxy-5-methoxy-phenol 90534-94-4 C9H12O3
2-Ethoxy-5-methoxy-phenol
—— [(E)-1-(4-hydroxyphenyl)butan-2-ylideneamino]thiourea 7145-44-0 C11H15N3OS
[(E)-1-(4-hydroxyphenyl)butan-2-ylideneamino]thiourea
—— 4-(1'-Cyclohexenyl)methyl-3-hydroxy-5-methoxybenzaldehyde 144328-54-1 C15H18O3
4-(1'-Cyclohexenyl)methyl-3-hydroxy-5-methoxybenzaldehyde
—— 2,4-dibromo-6-methyl-resorcinol 89794-19-4 C7H6Br2O2
2,4-dibromo-6-methyl-resorcinol
—— 6-bromo-2-fluoro-3-methylphenol 1310416-52-4 C7H6BrFO
6-bromo-2-fluoro-3-methylphenol
—— α-(2-Hydroxybenzyliden)-γ-butyrolacton 58165-18-7 C11H10O3
α-(2-Hydroxybenzyliden)-γ-butyrolacton
—— 2-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide 852951-43-0 C10H13NO3
2-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide
—— 2-bromo-3-methoxy-5-methylphenol 36661-64-0 C8H9BrO2
2-bromo-3-methoxy-5-methylphenol
—— 2,3,6-trichloro p-aminophenol 64981-10-8 C6H4Cl3NO
2,3,6-trichloro p-aminophenol
—— 3-bromo-2-<4-(ethoxycarbonyl)-3,5-hexadienyl>-4,6-dimethoxy-5-methylphenol 109035-18-9 C18H23BrO5
3-bromo-2-<4-(ethoxycarbonyl)-3,5-hexadienyl>-4,6-dimethoxy-5-methylphenol
—— 2-[(E)-(3-Methylbutylidene)amino]phenol 262846-55-9 C11H15NO
2-[(E)-(3-Methylbutylidene)amino]phenol
—— 2-hydroxy-4-methoxy-benzenesulfonic acid 120188-98-9 C7H8O5S
2-hydroxy-4-methoxy-benzenesulfonic acid
—— 6-ethyl-2,3-dimethoxy-phenol 39727-79-2 C10H14O3
6-ethyl-2,3-dimethoxy-phenol
—— 3,4-dichloro-6-methyl-pyrocatechol 374591-37-4 C7H6Cl2O2
3,4-dichloro-6-methyl-pyrocatechol
—— 3,5-dibromo-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid 204695-24-9 C12H12Br2O5
3,5-dibromo-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid
—— (Z)-4-(3,5-dimethoxy-4-hydroxybenzylidene)-2-methyl-1-propargyl-imidazoline-5-one 1396370-69-6 C16H16N2O4
(Z)-4-(3,5-dimethoxy-4-hydroxybenzylidene)-2-methyl-1-propargyl-imidazoline-5-one
—— 2-Hydroxy-4-methoxy-5,6-dimethylbenzaldehyd 34883-12-0 C10H12O3
2-Hydroxy-4-methoxy-5,6-dimethylbenzaldehyd
—— 4-Bromo-2-(cyclohexylmethyl)phenol 1243432-33-8 C13H17BrO
4-Bromo-2-(cyclohexylmethyl)phenol
—— 2-(cyclohexylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1542755-50-9 C19H29BO3
2-(cyclohexylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— rubrolide E 136762-97-5 C17H12O4
rubrolide E
—— 4-(pentafluoroethyl)-2-nitrophenol 1192021-18-3 C8H4F5NO3
4-(pentafluoroethyl)-2-nitrophenol
—— 7-(4-hydroxyphenyl)-1,3,5-cycloheptatriene 91902-42-0 C13H12O
7-(4-hydroxyphenyl)-1,3,5-cycloheptatriene
—— (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 946149-95-7 C18H15NO3
(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— 2,3,4,5,6-Pentallyl-phenol 41389-73-5 C21H26O
2,3,4,5,6-Pentallyl-phenol
—— 2,4-di-cyclopent-2-enyl-phenol 131887-43-9 C16H18O
2,4-di-cyclopent-2-enyl-phenol
—— N-2-butylnorepinephrine 18933-25-0 C12H19NO3
N-2-butylnorepinephrine
—— 2-(Chloromethyl)-6-methyl-4-nitrophenol 40638-53-7 C8H8ClNO3
2-(Chloromethyl)-6-methyl-4-nitrophenol
—— 5-Chlor-2-hydroxy-3-methylbenzylalkohol 37499-32-4 C8H9ClO2
5-Chlor-2-hydroxy-3-methylbenzylalkohol
—— 6-allyl-2,3-dimethylphenol 3796-87-0 C11H14O
6-allyl-2,3-dimethylphenol
—— 2-Bromo-6-(methoxymethyl)-4-nitrophenol 41464-11-3 C8H8BrNO4
2-Bromo-6-(methoxymethyl)-4-nitrophenol
—— 2-Brom-6-chlormethyl-4-nitrophenol 10491-25-5 C7H5BrClNO3
2-Brom-6-chlormethyl-4-nitrophenol
—— 3-Amino-2,4,5,6-tetrachlor-phenol 938-62-5 C6H3Cl4NO
3-Amino-2,4,5,6-tetrachlor-phenol
—— 2-hydroxy-N-(2-nitrobenzylidene)-aniline 3094-85-7 C13H12N2O
2-hydroxy-N-(2-nitrobenzylidene)-aniline
—— N-(4-tert-butyl-benzyl)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)acetamide 1258845-51-0 C20H24BrNO3
N-(4-tert-butyl-benzyl)-2-(3-bromo-4-hydroxy-5-methoxyphenyl)acetamide
—— 1-(4-fluorobenzyl)-3-(2-hydroxy-4-methoxybenzyl)-1-(1-methylpiperidin-4-yl)urea 1246458-18-3 C22H28FN3O3
1-(4-fluorobenzyl)-3-(2-hydroxy-4-methoxybenzyl)-1-(1-methylpiperidin-4-yl)urea
—— N-(4-tert-butyl-benzyl)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)acetamide 1258845-50-9 C20H24ClNO3
N-(4-tert-butyl-benzyl)-2-(3-chloro-4-hydroxy-5-methoxyphenyl)acetamide