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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
—— trans-3-<2-Hydroxy-4-methyl-5-methoxy-benzoyl>-2-methyl-acrylsaeure 15596-39-1 C13H14O5
trans-3-<2-Hydroxy-4-methyl-5-methoxy-benzoyl>-2-methyl-acrylsaeure
—— 1,5-Bis-(4-hydroxy-3-methyl-phenyl)-pentan-1,5-dion-dioxim 4642-26-6 C19H22N2O4
1,5-Bis-(4-hydroxy-3-methyl-phenyl)-pentan-1,5-dion-dioxim
—— 5-(2-Hydroxy-3.5-dimethyl-benzyl)-uracil 17187-53-0 C13H14N2O3
5-(2-Hydroxy-3.5-dimethyl-benzyl)-uracil
—— 5-Chloro-2-fluoro-4-methylphenol 1401798-67-1 C7H6ClFO
5-Chloro-2-fluoro-4-methylphenol
—— 2-(3,5-Dibrom-2-hydroxybenzyliden)-5-methyl-3H-furan-2-on; α-(2-Hydroxy-3,5-dibrombenzyliden)-Δ<sup>β,γ</sup>-angelicalacton 14065-77-1 C12H8Br2O3
2-(3,5-Dibrom-2-hydroxybenzyliden)-5-methyl-3H-furan-2-on; α-(2-Hydroxy-3,5-dibrombenzyliden)-Δ<sup>β,γ</sup>-angelicalacton
—— (4-glycoloylamino-3-hydroxy-2-nitro-phenyl)-arsonic acid 860728-44-5 C8H9AsN2O8
(4-glycoloylamino-3-hydroxy-2-nitro-phenyl)-arsonic acid
—— 1600520-99-7 C19H24N4O2
—— 1252801-69-6 C17H23NO5
—— 2-((2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-5-methylphenol 1613145-60-0 C15H27NO2Si
2-((2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-5-methylphenol
—— 4-[3-[Tert-butyl(dimethyl)silyl]oxy-3-methylpent-4-enyl]phenol 1258500-46-7 C18H30O2Si
4-[3-[Tert-butyl(dimethyl)silyl]oxy-3-methylpent-4-enyl]phenol
—— N-(3,4-dimethoxyphenethyl)-N-(3-hydroxy-4-methoxyphenethyl)trifluoacetamide 75608-47-8 C21H24F3NO5
N-(3,4-dimethoxyphenethyl)-N-(3-hydroxy-4-methoxyphenethyl)trifluoacetamide
—— 4-((2-((2-hydroxy-3,6-dimethylbenzylidene)amino)ethyl)amino)pent-3-en-2-one 137029-40-4 C16H22N2O2
4-((2-((2-hydroxy-3,6-dimethylbenzylidene)amino)ethyl)amino)pent-3-en-2-one
—— 4-(3,5-Difluoro-2-hydroxyphenyl)butan-2-one 1019769-65-3 C10H10F2O2
4-(3,5-Difluoro-2-hydroxyphenyl)butan-2-one
—— 5-(4-Hydroxy-3-methoxy-phenyl)-3-<4,7-dimethoxy-6-hydroxy-benzofuryl-(2)>-2-pyrazolin 6430-95-1 C20H20N2O6
5-(4-Hydroxy-3-methoxy-phenyl)-3-<4,7-dimethoxy-6-hydroxy-benzofuryl-(2)>-2-pyrazolin
—— (+/-)-3-(1-methylamino-ethyl)-phenol; hydrochloride 1269152-23-9 C9H13NO*ClH
(+/-)-3-(1-methylamino-ethyl)-phenol; hydrochloride
—— decanoic acid [2-(4-hydroxy-3,5-dimethoxy-phenyl)-5-(3-nitro-benzylidene)-4-oxo-thiazolidin-3-yl]amide 1290139-36-4 C28H35N3O7S
decanoic acid [2-(4-hydroxy-3,5-dimethoxy-phenyl)-5-(3-nitro-benzylidene)-4-oxo-thiazolidin-3-yl]amide
—— 3-Hydroxy-selenoanisol 1657-74-5 C7H8OSe
3-Hydroxy-selenoanisol
—— 2-(2-hydroxy-5-chloro)benzaldehyde-[4-(3-methyl-3-mesitylcyclobutyl)-1,3-thiazol-2-yl]hydrazone 676519-49-6 C24H26ClN3OS
2-(2-hydroxy-5-chloro)benzaldehyde-[4-(3-methyl-3-mesitylcyclobutyl)-1,3-thiazol-2-yl]hydrazone
—— 3,4-bis(hexyloxy)phenol 1253527-23-9 C18H30O3
3,4-bis(hexyloxy)phenol
—— 5-[(benzylamino)methyl]-2-nitrophenol 1374156-41-8 C14H14N2O3
5-[(benzylamino)methyl]-2-nitrophenol
—— 5-Butyl-2-phenethyl-3-triisopropylsilanyloxy-phenol 122760-71-8 C27H42O2Si
5-Butyl-2-phenethyl-3-triisopropylsilanyloxy-phenol
—— 2-[2-hydroxy-2-(2-propynyl)-4-pentynyl]phenol 953780-75-1 C14H14O2
2-[2-hydroxy-2-(2-propynyl)-4-pentynyl]phenol
—— 3,5-bis-morpholin-4-ylmethyl-benzene-1,2,4-triol 41273-87-4 C16H24N2O5
3,5-bis-morpholin-4-ylmethyl-benzene-1,2,4-triol
—— methyl (4S,4aR,7aS)-4-(2-(3,4-dihydroxyphenethoxy)-2-oxoethyl)-5-hydroxy-4a,5,7,7a-tetrahydro-4H-furo[3,4-b]pyran-3-carboxylate 125339-16-4 C19H22O9
methyl (4S,4aR,7aS)-4-(2-(3,4-dihydroxyphenethoxy)-2-oxoethyl)-5-hydroxy-4a,5,7,7a-tetrahydro-4H-furo[3,4-b]pyran-3-carboxylate
—— 6-[(Cyclohexylamino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one 106220-79-5 C14H19NO2
6-[(Cyclohexylamino)methylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— 5-(1-heptylcyclohexyl)resorcinol 951039-80-8 C19H30O2
5-(1-heptylcyclohexyl)resorcinol
—— 2-Hydroxy-4-methoxy-sorbophenon 106381-22-0 C13H14O3
2-Hydroxy-4-methoxy-sorbophenon
—— 2,7-bis(2-hydroxy-3,5-diiodophenyl)-3,6-diazaocta-2,6-diene 876344-88-6 C18H16I4N2O2
2,7-bis(2-hydroxy-3,5-diiodophenyl)-3,6-diazaocta-2,6-diene
—— N-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylideneamino]-2-(2-methylphenoxy)acetamide 5469-14-7 C17H16Br2N2O4
N-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylideneamino]-2-(2-methylphenoxy)acetamide
—— 3,4-Dimethoxy-(3-methoxy-4-hydroxy-benzal)-anilin 57322-41-5 C16H17NO4
3,4-Dimethoxy-(3-methoxy-4-hydroxy-benzal)-anilin
—— 1-(4-hydroxy-phenyl)-2-piperidin-1-yl-ethanol 53516-00-0 C13H19NO2
1-(4-hydroxy-phenyl)-2-piperidin-1-yl-ethanol
—— 3,3-diethyl-1-(2-hydroxy-benzylideneamino)-5-methyl-piperidine-2,4-dione 39844-58-1 C17H22N2O3
3,3-diethyl-1-(2-hydroxy-benzylideneamino)-5-methyl-piperidine-2,4-dione
—— 4-(2-Chlor-benzolazo)-5-hydroxy-benzotriazol 17857-96-4 C12H8ClN5O
4-(2-Chlor-benzolazo)-5-hydroxy-benzotriazol
—— 4-Methoxy-2-(methoxymethyl)oxymethylphenol 123035-05-2 C10H14O4
4-Methoxy-2-(methoxymethyl)oxymethylphenol
—— 2,3,5-tribromo-4,6-dichloro-phenol 143106-22-3 C6HBr3Cl2O
2,3,5-tribromo-4,6-dichloro-phenol
—— 2-{[4,5-diamino-1-(2-hydroxy-ethyl)-1H-pyrazole-3-ylmethyl]-amino}-4-nitro-phenol 459839-61-3 C12H16N6O4
2-{[4,5-diamino-1-(2-hydroxy-ethyl)-1H-pyrazole-3-ylmethyl]-amino}-4-nitro-phenol
—— 6-sec-Pentyl-2-chlor-p-cresol 2502-80-9 C12H17ClO
6-sec-Pentyl-2-chlor-p-cresol
—— 2-[[2-[[(2-Hydroxy-5-nitrophenyl)methylideneamino]methyl]-3-pyridin-2-ylpropyl]iminomethyl]-4-nitrophenol 219510-18-6 C23H21N5O6
2-[[2-[[(2-Hydroxy-5-nitrophenyl)methylideneamino]methyl]-3-pyridin-2-ylpropyl]iminomethyl]-4-nitrophenol
—— 4-Chloro-3,5-dimethyl-2,6-dinitro-phenol; compound with morpholine 4102-82-3 C4H9NO*C8H7ClN2O5
4-Chloro-3,5-dimethyl-2,6-dinitro-phenol; compound with morpholine
—— 1-ethyl-2-[2-(2-hydroxy-5-nitrophenyl)ethyl]-3,3-dimethyl-3H-indolium chloride 1458033-57-2 C20H23N2O3*Cl
1-ethyl-2-[2-(2-hydroxy-5-nitrophenyl)ethyl]-3,3-dimethyl-3H-indolium chloride
—— N(2-hydroxybenzylidene)-N'(2-hydroxyacetophenone)-1,3-propanediamine 71381-80-1 C17H18N2O2
N(2-hydroxybenzylidene)-N'(2-hydroxyacetophenone)-1,3-propanediamine
—— 1-(2-Hydroxy-6-methoxy-phenyl)-ethanone oxime 4003-26-3 C9H11NO3
1-(2-Hydroxy-6-methoxy-phenyl)-ethanone oxime
—— 3,4-Dihydroxy-<5-2H>-toluol 4840-40-8 C7H8O2
3,4-Dihydroxy-<5-2H>-toluol
—— 1-(2'-(((2-(trimethylsilyl)ethoxy)carbonyl)amino)-4'-hydroxy-5'-methoxybenzoyl)-2-pyrrolidinecarboxaldehyde dimethyl acetal 123267-59-4 C21H34N2O7Si
1-(2'-(((2-(trimethylsilyl)ethoxy)carbonyl)amino)-4'-hydroxy-5'-methoxybenzoyl)-2-pyrrolidinecarboxaldehyde dimethyl acetal
—— 2,5-Dihydroxy-4-methoxy-4'-<2-brom-aethyl>-diphenylsulfon 92551-10-5 C15H15BrO5S
2,5-Dihydroxy-4-methoxy-4'-<2-brom-aethyl>-diphenylsulfon
—— 4-fluoro-8-(4-fluorophenyl)-9-[6-(methyl{3-[(3,3,4,4,4-pentafluorobutyl)sulphonyl]propyl}amino)hexyl]-6,7-dihydro-5H-benzo[7]annulen-3-ol 1353006-86-6 C31H38F7NO3S
4-fluoro-8-(4-fluorophenyl)-9-[6-(methyl{3-[(3,3,4,4,4-pentafluorobutyl)sulphonyl]propyl}amino)hexyl]-6,7-dihydro-5H-benzo[7]annulen-3-ol
—— 2,4-dinitro-6-(norbonylen-1-yl)phenol 103068-32-2 C13H12N2O5
2,4-dinitro-6-(norbonylen-1-yl)phenol
—— 3-Ethyl-5-methyl-4-[2-methyl-pent-(E)-ylideneamino]-phenol 2830-66-2 C15H23NO
3-Ethyl-5-methyl-4-[2-methyl-pent-(E)-ylideneamino]-phenol
—— [9-3H]coniferyl alcohol 140215-89-0 C10H12O3
[9-3H]coniferyl alcohol
—— 6-Methoxy-2-(5-chlor-salicylidenhydrazino)-pyrimidin 91398-47-9 C12H11ClN4O2
6-Methoxy-2-(5-chlor-salicylidenhydrazino)-pyrimidin