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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
—— 4-[7-(4-Hydroxyphenoxy)heptyl]-3,5-heptanedione 56219-68-2 C20H30O4
4-[7-(4-Hydroxyphenoxy)heptyl]-3,5-heptanedione
—— (5E)-bicyclo[8.2.2]tetradeca-1(12),5,10,13-tetraene-11,13-diol 78740-00-8 C14H18O2
(5E)-bicyclo[8.2.2]tetradeca-1(12),5,10,13-tetraene-11,13-diol
—— β-Pyridyl-carbinol-picrat 6164-82-5 C6H3N3O7*C6H7NO
β-Pyridyl-carbinol-picrat
—— Guaiacol picrate 60261-30-5 C13H11N3O9
Guaiacol picrate
—— <i>A</i><i>s</i>,<i>A</i><i>s</i>'-bis-(3-hydroxy-phenyl)-<i>A</i><i>s</i>,<i>A</i><i>s</i>'-diphenyl-diarsane 855266-61-4 C24H20As2O2
<i>A</i><i>s</i>,<i>A</i><i>s</i>'-bis-(3-hydroxy-phenyl)-<i>A</i><i>s</i>,<i>A</i><i>s</i>'-diphenyl-diarsane
—— 2-[(2,2-diethoxy-ethylimino)-methyl]-phenol 116632-97-4 C13H19NO3
2-[(2,2-diethoxy-ethylimino)-methyl]-phenol
—— 4-Chloro-2-[(2-propenoxyimino)methyl]phenol 103742-89-8 C10H10ClNO2
4-Chloro-2-[(2-propenoxyimino)methyl]phenol
—— 4-methoxy-3-(6-oxo-3(1H)-pyridazinylmethyl)-phenol hydrochloride 105170-21-6 C12H12N2O3*ClH
4-methoxy-3-(6-oxo-3(1H)-pyridazinylmethyl)-phenol hydrochloride
—— Bis-(3,5-dimethyl-4-hydroxyphenyl)-cyclopropenon 25361-96-0 C19H18O3
Bis-(3,5-dimethyl-4-hydroxyphenyl)-cyclopropenon
—— (R)-4-(2-((3-chlorophenyl)amino)-1-hydroxyethyl)benzene-1,2-diol 1544695-65-9 C14H14ClNO3
(R)-4-(2-((3-chlorophenyl)amino)-1-hydroxyethyl)benzene-1,2-diol
—— (S)-2-(2-hydroxybenzylideneamino)-1,5-pentanediol 129049-06-5 C12H17NO3
(S)-2-(2-hydroxybenzylideneamino)-1,5-pentanediol
—— 3,6-didodecylcatechol 343808-59-3 C30H54O2
3,6-didodecylcatechol
—— (2R,4S,6R)-2-[2-(benzyloxy)ethyl]-6-(4-hydroxy-3-methoxyphenyl)tetrahydro-2H-pyran-4-ol 1609536-86-8 C21H26O5
(2R,4S,6R)-2-[2-(benzyloxy)ethyl]-6-(4-hydroxy-3-methoxyphenyl)tetrahydro-2H-pyran-4-ol
—— (2-hydroxyphenyl)diisopropylphosphine 288099-29-6 C12H19OP
(2-hydroxyphenyl)diisopropylphosphine
—— 5-Hydrazinyl-2-methoxyphenol 1314959-35-7 C7H10N2O2
5-Hydrazinyl-2-methoxyphenol
—— 2-{[(E)-(3aS,5R,6S,6aS)-2,2,5-Trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ylimino]-methyl}-phenol 39798-37-3 C15H19NO4
2-{[(E)-(3aS,5R,6S,6aS)-2,2,5-Trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ylimino]-methyl}-phenol
—— 4-hydroxy-2-methyl-thiobenzoic acid anilide 120951-43-1 C14H13NOS
4-hydroxy-2-methyl-thiobenzoic acid anilide
—— 4-<2-Hydroxy-5-methyl-phenyl>-buttersaeure-methylester 105401-47-6 C12H16O3
4-<2-Hydroxy-5-methyl-phenyl>-buttersaeure-methylester
—— 4-(3,4-Dihydroxyphenyl)-2-(2,4-dichlorophenylamino)thiazole hydrochloride 79571-68-9 C15H10Cl2N2O2S*ClH
4-(3,4-Dihydroxyphenyl)-2-(2,4-dichlorophenylamino)thiazole hydrochloride
—— 4-dodecoxy-2,5-diiodophenol 206433-38-7 C18H28I2O2
4-dodecoxy-2,5-diiodophenol
—— 3,5-dibenzyloxybenzoylvanillinhydrazone 768368-77-0 C29H26N2O5
3,5-dibenzyloxybenzoylvanillinhydrazone
—— 4-(α-(m-Hydroxy-phenylimino)-α-methylmercapto-methyl)-1,2-diphenyl-3,5-dioxo-pyrazolidin 19744-30-0 C23H19N3O3S
4-(α-(m-Hydroxy-phenylimino)-α-methylmercapto-methyl)-1,2-diphenyl-3,5-dioxo-pyrazolidin
—— 1427163-03-8 C17H26N2O2
—— (4-hydroxyphenyl)-5-(3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenyl)-1,3,4-oxadiazole 139521-50-9 C22H14N4O4
(4-hydroxyphenyl)-5-(3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenyl)-1,3,4-oxadiazole
—— 1-(4,5-Dimethyl-2-hydroxyphenyl)-3-(2-methyl-4-thiazolyl)propenone 80378-04-7 C15H15NO2S
1-(4,5-Dimethyl-2-hydroxyphenyl)-3-(2-methyl-4-thiazolyl)propenone
—— 2,3-dihydroxy-4,5-dimethoxybenzaldehyde 82835-23-2 C9H10O5
2,3-dihydroxy-4,5-dimethoxybenzaldehyde
—— 2-Hydroxy-3,5-dinitro-4-trifluoromethyl-benzoic acid 50343-75-4 C8H3F3N2O7
2-Hydroxy-3,5-dinitro-4-trifluoromethyl-benzoic acid
—— 2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenol 831223-27-9 C27H33FO2SeSi
2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenol
—— 4-[3-(2-bromoethoxy)propyloxy]-2,3,6-trimethylphenol 264925-26-0 C14H21BrO3
4-[3-(2-bromoethoxy)propyloxy]-2,3,6-trimethylphenol
—— 4-(1-methyl-1-propyl-pent-4-en-2-ynyl)-phenol 861010-23-3 C15H18O
4-(1-methyl-1-propyl-pent-4-en-2-ynyl)-phenol
—— 6,6-bis-(4-hydroxy-3-methyl-5-nitro-phenyl)-heptanoic acid 111161-97-8 C21H24N2O8
6,6-bis-(4-hydroxy-3-methyl-5-nitro-phenyl)-heptanoic acid
—— N'-(4-Hydroxy-3-methoxybenzylidene)-2-(4-methylphenoxy)acetohydrazide 93649-72-0 C17H18N2O4
N'-(4-Hydroxy-3-methoxybenzylidene)-2-(4-methylphenoxy)acetohydrazide
—— N,N-dimethyl-2-(4-(heptylthio)-2-hydroxy-5-methoxyphenyl)-3-methylbutylamine 129658-36-2 C21H37NO2S
N,N-dimethyl-2-(4-(heptylthio)-2-hydroxy-5-methoxyphenyl)-3-methylbutylamine
—— 2,4,6-tris(1-(2-salicylaldimino-2-methylpropylimino)-ethyl)-1,3,5-trihydroxybenzene 618382-31-3 C45H54N6O6
2,4,6-tris(1-(2-salicylaldimino-2-methylpropylimino)-ethyl)-1,3,5-trihydroxybenzene
—— 2,6-Dibromo-4-pent-4-ynylphenol 1245947-59-4 C11H10Br2O
2,6-Dibromo-4-pent-4-ynylphenol
—— 2-(4-chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one 960400-83-3 C20H16ClNO3S
2-(4-chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one
—— 2-[[[6-(4-Iodoanilino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]hydrazinylidene]methyl]-4,6-dinitrophenol 312285-06-6 C17H10IN9O6
2-[[[6-(4-Iodoanilino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]hydrazinylidene]methyl]-4,6-dinitrophenol
—— 4-tert-butyl-2-hydroxy-5-methoxybenzaldehyde 1055987-77-3 C12H16O3
4-tert-butyl-2-hydroxy-5-methoxybenzaldehyde
—— 1384118-64-2 C24H38LaN10O3
—— 4-hydroxy-5-[(4-hydroxy-2-oxo-3H-1,3-thiazol-5-yl)-(3-hydroxyphenyl)methyl]-3H-1,3-thiazol-2-one 1009814-43-0 C13H10N2O5S2
4-hydroxy-5-[(4-hydroxy-2-oxo-3H-1,3-thiazol-5-yl)-(3-hydroxyphenyl)methyl]-3H-1,3-thiazol-2-one
—— Dihexadecyl-(2-hydroxy-5-nitro-benzyl)-methyl-ammonium; bromide 104407-35-4 Br*C40H75N2O3
Dihexadecyl-(2-hydroxy-5-nitro-benzyl)-methyl-ammonium; bromide
—— 2-Hydroxy-benzaldehyd-ethoxy-thiocarbonylhydrazon 87962-86-5 C10H12N2O2S
2-Hydroxy-benzaldehyd-ethoxy-thiocarbonylhydrazon
—— 32340-88-8 C16H18O4S
—— 1445780-93-7 C20H33O8P
—— 2-Oxo-3,4-dimethyl-6-<4-hydroxy-3,5-dimethyl-phenyl>-hexahydropyrimidin 108238-81-9 C14H20N2O2
2-Oxo-3,4-dimethyl-6-<4-hydroxy-3,5-dimethyl-phenyl>-hexahydropyrimidin
—— salicylaldehydedithioglycerol 104166-27-0 C13H20O5S2
salicylaldehydedithioglycerol
—— 1-(2-Hydroxyphenyl)-1,2-dihydroxypentan 1481-87-4 C11H16O3
1-(2-Hydroxyphenyl)-1,2-dihydroxypentan
—— 4-vanilideneamino-3-methyl-5-mercapto-1,2,4-triazole 315689-15-7 C11H12N4O2S
4-vanilideneamino-3-methyl-5-mercapto-1,2,4-triazole
—— potassium vanillidensulfamate 22102-25-6 C8H8NO5S*K
potassium vanillidensulfamate
—— 2-[2-amino-6-(4-methoxyphenyl)-6H-1,3-thiazin-4-yl]-6-bromo-4-methylphenol 75793-96-3 C18H17BrN2O2S
2-[2-amino-6-(4-methoxyphenyl)-6H-1,3-thiazin-4-yl]-6-bromo-4-methylphenol