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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
—— 2,2,2-trifluoro-N-[(2-hydroxyphenyl)methylideneamino]acetamide 66133-51-5 C9H7F3N2O2
2,2,2-trifluoro-N-[(2-hydroxyphenyl)methylideneamino]acetamide
—— N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)-3-(2,3,4-trihydroxyphenyl)propanamide 1228675-84-0 C15H23NO9
N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)-3-(2,3,4-trihydroxyphenyl)propanamide
—— 5-(2-Hydroxy-4-methoxy-phenyl)-2-methyl-2,4-dihydro-pyrazol-3-one 98411-92-8 C11H12N2O3
5-(2-Hydroxy-4-methoxy-phenyl)-2-methyl-2,4-dihydro-pyrazol-3-one
—— trans-3-<4-Chlor-2-hydroxy-5-methoxy-benzoyl>-2-methyl-acrylsaeure 14554-01-9 C12H11ClO5
trans-3-<4-Chlor-2-hydroxy-5-methoxy-benzoyl>-2-methyl-acrylsaeure
—— N,N'-bis[(Z)-(5-chloro-2-hydroxyphenyl)methylideneamino]hexanediamide 6342-31-0 C20H20Cl2N4O4
N,N'-bis[(Z)-(5-chloro-2-hydroxyphenyl)methylideneamino]hexanediamide
—— 1-{[1-(2,4-Dihydroxy-phenyl)-meth-(E)-ylidene]-amino}-pyridinium; iodide 19350-40-4 C12H11N2O2*I
1-{[1-(2,4-Dihydroxy-phenyl)-meth-(E)-ylidene]-amino}-pyridinium; iodide
—— 4-bromo-5-tert-butylguaiacol 21099-11-6 C11H15BrO2
4-bromo-5-tert-butylguaiacol
—— 5<i>t</i>-(2,5-dihydroxy-phenyl)-penta-2<i>t</i>,4-dienoic acid 99846-27-2 C11H10O4
5<i>t</i>-(2,5-dihydroxy-phenyl)-penta-2<i>t</i>,4-dienoic acid
—— 2-Hydroxy-benzylidenoxim-O-trimethylsilyl-ether 17876-75-4 C10H15NO2Si
2-Hydroxy-benzylidenoxim-O-trimethylsilyl-ether
—— 2-(4-bromo-2-hydroxybenzylidene)hydrazine-1-carbothioamide 7410-46-0 C8H8BrN3OS
2-(4-bromo-2-hydroxybenzylidene)hydrazine-1-carbothioamide
—— Acetyloxy-[4-[(4-hydroxy-3-methoxyphenyl)methylideneamino]phenyl]mercury 5439-21-4 C16H15HgNO4
Acetyloxy-[4-[(4-hydroxy-3-methoxyphenyl)methylideneamino]phenyl]mercury
—— α-<p-Hydroxy-phenylimino>-<1-methyl-pyrrolyl-(2)>-acetonitril 21553-27-5 C13H11N3O
α-<p-Hydroxy-phenylimino>-<1-methyl-pyrrolyl-(2)>-acetonitril
—— 4-Isopropyl-1-(5-chlor-2-hydroxy-benzyliden)-thiosemicarbazid 19152-26-2 C11H14ClN3OS
4-Isopropyl-1-(5-chlor-2-hydroxy-benzyliden)-thiosemicarbazid
—— 2-[(2,3-dimethoxy-phenethylimino)-methyl]-6-methoxy-phenol 110492-04-1 C18H21NO4
2-[(2,3-dimethoxy-phenethylimino)-methyl]-6-methoxy-phenol
—— 2-Hydroxy-3-methoxy-benzaldehyd-(4-benzoylamino-thiosemicarbazon) 13737-51-4 C16H16N4O3S
2-Hydroxy-3-methoxy-benzaldehyd-(4-benzoylamino-thiosemicarbazon)
—— 5-Aethyl-2,4-dihydroxy-benzaldehyd-4-allylthiosemicarbazon 19015-24-8 C13H17N3O2S
5-Aethyl-2,4-dihydroxy-benzaldehyd-4-allylthiosemicarbazon
—— 4,6-Dihydroxy-2-methyl-isophthaldialdehyd-dioxim 10209-60-6 C9H10N2O4
4,6-Dihydroxy-2-methyl-isophthaldialdehyd-dioxim
—— 17560-28-0 C23H16N6O6
—— 2-[(2-Hydroxy-5-methylphenyl)methylideneamino]-2-methylpropane-1,3-diol 180092-04-0 C12H17NO3
2-[(2-Hydroxy-5-methylphenyl)methylideneamino]-2-methylpropane-1,3-diol
—— 4-Nitro-3,5-bis-p-tosyloxy-phenol 20032-67-1 C20H17NO9S2
4-Nitro-3,5-bis-p-tosyloxy-phenol
—— hexanoylsalicylaldoxime 80277-94-7 C13H17NO3
hexanoylsalicylaldoxime
—— 13936-85-1 C22H24Cl2F2N2O2
—— 2-Aethoxycarbonyl-3-<2-hydroxyphenyl>-5-<3-brom-5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on 3967-77-9 C21H18BrFO5
2-Aethoxycarbonyl-3-<2-hydroxyphenyl>-5-<3-brom-5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on
—— 3-methoxybenzyl 3-hydroxybenzo[b]thiophene-2-carboxylate 1443209-16-2 C17H14O4S
3-methoxybenzyl 3-hydroxybenzo[b]thiophene-2-carboxylate
—— 1,4-Benzenediol, 2-(2-isocyanoethenyl)- 113590-11-7 C9H7NO2
1,4-Benzenediol, 2-(2-isocyanoethenyl)-
—— 4-[(E)-[5-[5-[[7-[5-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-1,3,4-thiadiazol-2-yl]-3-methyl-1-benzofuran-5-yl]methyl]-3-methyl-1-benzofuran-7-yl]-1,3,4-thiadiazol-2-yl]iminomethyl]-2-methoxyphenol 1252934-10-3 C39H30N6O6S2
4-[(E)-[5-[5-[[7-[5-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-1,3,4-thiadiazol-2-yl]-3-methyl-1-benzofuran-5-yl]methyl]-3-methyl-1-benzofuran-7-yl]-1,3,4-thiadiazol-2-yl]iminomethyl]-2-methoxyphenol
—— 4(e)-(2,5-Dihydroxyphenyl)cyclohexan-(a)-carbaldehyd 152427-68-4 C13H16O3
4(e)-(2,5-Dihydroxyphenyl)cyclohexan-(a)-carbaldehyd
—— 4-((piperidin-1-ylimino)methyl)benzene-1,3-diol 453551-17-2 C12H16N2O2
4-((piperidin-1-ylimino)methyl)benzene-1,3-diol
—— methyl-5-{4-hydroxy-3-[2-(methoxycarbonyl)ethyl]phenyl}pentanoate 197708-00-2 C16H22O5
methyl-5-{4-hydroxy-3-[2-(methoxycarbonyl)ethyl]phenyl}pentanoate
—— 2-amino-5-(5-chloro-2-hydroxy)phenyl-1,3,4-oxadiazole 18233-12-0 C8H6ClN3O2
2-amino-5-(5-chloro-2-hydroxy)phenyl-1,3,4-oxadiazole
—— 2,5-diiodo-3,6-dimethoxy-hydroquinone 98546-38-4 C8H8I2O4
2,5-diiodo-3,6-dimethoxy-hydroquinone
—— 7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-3-hydroxy-4-(4-hydroxy-3-methyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester 443147-42-0 C24H34O6
7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-3-hydroxy-4-(4-hydroxy-3-methyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
—— 213465-29-3 C38H30NiO8
—— N-Iodoacetyl-3,5-dimethoxy-4-hydroxyphenylpropylamin 54844-09-6 C13H18INO4
N-Iodoacetyl-3,5-dimethoxy-4-hydroxyphenylpropylamin
—— 2,5-dipropyl-4-[2-(dimethylphenylsilyl)ethyl]phenol 1230389-27-1 C22H32OSi
2,5-dipropyl-4-[2-(dimethylphenylsilyl)ethyl]phenol
—— Biphenyl-3,4,3',4'-tetraamine; compound with 2,4-dinitro-phenol 92415-63-9 C6H4N2O5*C12H14N4
Biphenyl-3,4,3',4'-tetraamine; compound with 2,4-dinitro-phenol
—— 2,4-Dinitro-phenol; compound with diisobutyl-amine 65264-12-2 C6H4N2O5*C8H19N
2,4-Dinitro-phenol; compound with diisobutyl-amine
—— 2-(2-Hydroxy-phenyl)-butane-1,4-diol 110451-73-5 C10H14O3
2-(2-Hydroxy-phenyl)-butane-1,4-diol
—— 2-[N-[(4,6-dimethylpyrimidin-2-yl)amino]-C-methylcarbonimidoyl]phenol 424800-31-7 C14H16N4O
2-[N-[(4,6-dimethylpyrimidin-2-yl)amino]-C-methylcarbonimidoyl]phenol
—— 2-methyl-3-ethyl-4-hydroxypyrylium cation 62968-77-8 C8H11O2
2-methyl-3-ethyl-4-hydroxypyrylium cation
—— 4-Cyclohexyl-1-(5-chlor-2-hydroxy-benzyliden)-thiosemicarbazid 19152-30-8 C14H18ClN3OS
4-Cyclohexyl-1-(5-chlor-2-hydroxy-benzyliden)-thiosemicarbazid
—— 4-Tert-butyl-2-(hydroxymethyl)-6-methoxyphenol 37987-08-9 C12H18O3
4-Tert-butyl-2-(hydroxymethyl)-6-methoxyphenol
—— 1417182-14-9 C16H17NO3
—— 5-methyl-4-(thiazol-2-yldiazenyl)benzene-1,3-diol 96627-61-1 C10H9N3O2S
5-methyl-4-(thiazol-2-yldiazenyl)benzene-1,3-diol
—— 3,3'-bis-(4-hydroxy-phenyl)-5,5'-diimino-4,4,4',4'-tetramethyl-1,1'-<i>m</i>-phenylene-bis-imidazolidin-2-one 29210-47-7 C28H28N6O4
3,3'-bis-(4-hydroxy-phenyl)-5,5'-diimino-4,4,4',4'-tetramethyl-1,1'-<i>m</i>-phenylene-bis-imidazolidin-2-one
—— N-<2-Hydroxy-5-methyl-benzyliden>-o-toluidin 22537-67-3 C15H15NO
N-<2-Hydroxy-5-methyl-benzyliden>-o-toluidin
—— 2,4-Dibromo-6-{[(E)-2-mercapto-ethylimino]-methyl}-phenol 20115-01-9 C9H9Br2NOS
2,4-Dibromo-6-{[(E)-2-mercapto-ethylimino]-methyl}-phenol
—— 2,4-Dihydroxy-5-isopentyl-benzaldehyd-4-(2-aethoxy-phenyl)-thiosemicarbazon 18965-19-0 C21H27N3O3S
2,4-Dihydroxy-5-isopentyl-benzaldehyd-4-(2-aethoxy-phenyl)-thiosemicarbazon
—— cis-b-2,4-Dihydroxybenzoylacrylsaeure 59631-84-4 C10H8O5
cis-b-2,4-Dihydroxybenzoylacrylsaeure
—— N-(5-amino-4-cyano-3-(4-hydroxyphenyl)-2,3-dihydrothiophene-2-carbonyl)piperidine-1-carboxamide 1146596-11-3 C18H20N4O3S
N-(5-amino-4-cyano-3-(4-hydroxyphenyl)-2,3-dihydrothiophene-2-carbonyl)piperidine-1-carboxamide