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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-(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
—— (3-chloro-4-hydroxy-5-methoxyphenyl)acetic acid 88516-93-2 C9H9ClO4
(3-chloro-4-hydroxy-5-methoxyphenyl)acetic acid
—— N-(4-tert-butyl-benzyl)-2-(3-iodo-4-hydroxy-5-methoxyphenyl)acetamide 1258845-52-1 C20H24INO3
N-(4-tert-butyl-benzyl)-2-(3-iodo-4-hydroxy-5-methoxyphenyl)acetamide
—— 2,6-Dimethoxy-4-<4-(indol-3-yl)butyl>phenol 158555-51-2 C20H23NO3
2,6-Dimethoxy-4-<4-(indol-3-yl)butyl>phenol
—— Methyl-bis<o-hydroxyphenyl>-phosphin 77013-86-6 C13H13O2P
Methyl-bis<o-hydroxyphenyl>-phosphin
—— methyl 3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propionate 1187947-20-1 C15H14FN3O5
methyl 3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propionate
—— Nifursol 16915-70-1 C12H7N5O9
Nifursol
—— 2-hydroxy-5-nitro-N-tert-butoxyphenylacetyl amide 155388-59-3 C12H16N2O5
2-hydroxy-5-nitro-N-tert-butoxyphenylacetyl amide
—— 3,4,5-trimethyl-2,6-dinitrophenol 125065-87-4 C9H10N2O5
3,4,5-trimethyl-2,6-dinitrophenol
—— ethyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxyphenyl)propanoate 1016638-48-4 C11H11F3O4
ethyl (2S)-3,3,3-trifluoro-2-hydroxy-2-(4-hydroxyphenyl)propanoate
—— 2,3-di-n-butylphenol 26967-68-0 C14H22O
2,3-di-n-butylphenol
—— (4S)-5-(3-hydroxyphenyl)-γ-valerolactone 1236063-80-1 C11H12O3
(4S)-5-(3-hydroxyphenyl)-γ-valerolactone
—— N-[(E)-but-2-enyl]-N-(2,2-diethoxyethyl)-3-hydroxy-2-nitrobenzamide 94295-89-3 C17H24N2O6
N-[(E)-but-2-enyl]-N-(2,2-diethoxyethyl)-3-hydroxy-2-nitrobenzamide
—— 5-[2-[2-(3,4,5-Trihydroxyphenyl)ethenylsulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol 862097-17-4 C17H16O10S2
5-[2-[2-(3,4,5-Trihydroxyphenyl)ethenylsulfonylmethylsulfonyl]ethenyl]benzene-1,2,3-triol
—— 2-hydroxyacetophenone (4)N-dimethylthiosemicarbazone 166036-45-9 C11H15N3OS
2-hydroxyacetophenone (4)N-dimethylthiosemicarbazone
—— 1-(4-fluorobenzyl)-3-(4-hydroxy-2-methoxybenzyl)-1(1-methylpiperidin-4-yl)urea 1246458-19-4 C22H28FN3O3
1-(4-fluorobenzyl)-3-(4-hydroxy-2-methoxybenzyl)-1(1-methylpiperidin-4-yl)urea
—— 1-N',2-N'-bis[[(E)-(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]ethanediimidamide 6343-38-0 C16H16N6O2
1-N',2-N'-bis[[(E)-(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]ethanediimidamide
—— oxalodiimidic acid bis-salicylidenehydrazide 6343-38-0 C16H16N6O2
oxalodiimidic acid bis-salicylidenehydrazide
—— 2-[[4-[[(2-Hydroxyphenyl)methylideneamino]methyl]cyclohexyl]methyliminomethyl]phenol 3353-15-9 C22H26N2O2
2-[[4-[[(2-Hydroxyphenyl)methylideneamino]methyl]cyclohexyl]methyliminomethyl]phenol
—— 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-ethoxy-4-pentafluoroethyl-6(1H)-pyrimidinone 115784-67-3 C14H9ClF6N2O3
1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-ethoxy-4-pentafluoroethyl-6(1H)-pyrimidinone
—— 2-(4-chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one 892871-50-0 C19H15ClN2O3S
2-(4-chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one