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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
—— 3-(3,4-Dihydroxyphenyl)propyl 2-cyanoacetate 132465-19-1 C12H13NO4
3-(3,4-Dihydroxyphenyl)propyl 2-cyanoacetate
—— 5-(3,4-dihydroxy-5-trifluoromethylbenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione 1372864-88-4 C17H18F3NO4S
5-(3,4-dihydroxy-5-trifluoromethylbenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione
—— 2,6-Dinitro-4-(1-methyloctyl)-phenol 4097-46-5 C15H22N2O5
2,6-Dinitro-4-(1-methyloctyl)-phenol
—— 2-(4-(4-(2-hydroxyphenyl)-5,6-dihydropyridin-1(2H)-yl)butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione 1351409-74-9 C19H24N4O3
2-(4-(4-(2-hydroxyphenyl)-5,6-dihydropyridin-1(2H)-yl)butyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione
—— N-[(4-Hydroxyphenyl)methyl]methoxy-N-(2-methyl-2-sulfanylpropyl)carboxamide 364056-24-6 C13H19NO3S
N-[(4-Hydroxyphenyl)methyl]methoxy-N-(2-methyl-2-sulfanylpropyl)carboxamide
—— 4-(4-formyl-3-hydroxyphenoxy)-N,N,N,-trimethylethan-1-ammonium bromide 898803-84-4 Br*C12H18NO3
4-(4-formyl-3-hydroxyphenoxy)-N,N,N,-trimethylethan-1-ammonium bromide
—— N-[2-(dimethylamino)ethyl]-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276702-78-4 C10H14ClN3O5S
N-[2-(dimethylamino)ethyl]-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— (R)-4-(2-(4-(cycloheptylmethyl)piperazin-1-yl)-3-(methylamino)propyl)phenol 1186220-07-4 C22H37N3O
(R)-4-(2-(4-(cycloheptylmethyl)piperazin-1-yl)-3-(methylamino)propyl)phenol
—— 4,6-diiodo-2-[[(2,6-diethylphenyl)imino]methyl]phenol 597564-05-1 C17H17I2NO
4,6-diiodo-2-[[(2,6-diethylphenyl)imino]methyl]phenol
—— 2,4-dihydroxythiobenzanilide 181875-13-8 C13H11NO2S
2,4-dihydroxythiobenzanilide
—— 1-(2-hydroxy-3-methylphenyl)-3-thiophen-2-ylprop-2-en-1-one 600151-64-2 C14H12O2S
1-(2-hydroxy-3-methylphenyl)-3-thiophen-2-ylprop-2-en-1-one
—— 2-[2-(diphenylphosphino)ethyliminomethyl]phenol 23721-98-4 C21H20NOP
2-[2-(diphenylphosphino)ethyliminomethyl]phenol
—— β-(2-Hydroxy-4-nitro-phenyl)-propionsaeure-ethylester 20921-16-8 C11H13NO5
β-(2-Hydroxy-4-nitro-phenyl)-propionsaeure-ethylester
—— Methyl 2-(3-bromo-5-hydroxyphenyl)acetate 1105589-32-9 C9H9BrO3
Methyl 2-(3-bromo-5-hydroxyphenyl)acetate
—— 3-(2,4-Dihydroxy-phenyl)-5-(3,5-dibrom-2-hydroxy-phenyl)-isooxazol 19743-19-2 C15H9Br2NO4
3-(2,4-Dihydroxy-phenyl)-5-(3,5-dibrom-2-hydroxy-phenyl)-isooxazol
—— 5-(4-hydroxy-3-methoxyphenyl)-penta-2E,4E-dienoic acid 3.4-dihydroxybenzylamide 878800-21-6 C19H19NO5
5-(4-hydroxy-3-methoxyphenyl)-penta-2E,4E-dienoic acid 3.4-dihydroxybenzylamide
—— 41350-41-8 C20H16N2O2S2
—— 41350-43-0 C20H16N2O2S2
—— 22923-29-1 C13H6Cl6O3
—— 5-Formyl-6-hydroxy-2-oxo-1,3-benzoxathiol 92222-89-4 C8H4O4S
5-Formyl-6-hydroxy-2-oxo-1,3-benzoxathiol
—— 41571-15-7 C19H20N4O6S
—— N,N'-bis(3,5-Br2-salicylidene)-1,2-diimino-2,2-dimethylethane 874274-50-7 C18H16Br4N2O2
N,N'-bis(3,5-Br2-salicylidene)-1,2-diimino-2,2-dimethylethane
—— N-(2-benzyloxyethyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276703-06-1 C15H15ClN2O6S
N-(2-benzyloxyethyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— 51084-56-1 C11H12N4O5S
—— 1416952-19-6 C11H12O4
—— 5-(2-Aminoethoxy)-2-chlorophenol 26378-47-2 C8H10ClNO2
5-(2-Aminoethoxy)-2-chlorophenol
—— 104676-54-2 C13H18NiO5S2
—— 9-Oxo-9,10-seco-oestron 26509-78-4 C18H22O3
9-Oxo-9,10-seco-oestron
—— N,N'-bis(3-methoxysalicylidene)-2,3-diaminopyridine 376355-02-1 C21H19N3O4
N,N'-bis(3-methoxysalicylidene)-2,3-diaminopyridine
—— 3.5-Dibrom-2'.4'-dichlorthionosalicylsaeureanilid 19112-10-8 C13H7Br2Cl2NOS
3.5-Dibrom-2'.4'-dichlorthionosalicylsaeureanilid
—— 4-Hydroxy-1-(thiophen-2-sulfonylhydrazonomethyl)-benzol 79280-04-9 C11H10N2O3S2
4-Hydroxy-1-(thiophen-2-sulfonylhydrazonomethyl)-benzol
—— 10-Amino-6,7,8,9,10,11-hexahydro-5H-benzocyclononene-1,11-diol 126538-61-2 C13H19NO2
10-Amino-6,7,8,9,10,11-hexahydro-5H-benzocyclononene-1,11-diol
—— 3-bromo-5-methyl-4-hydroxyphenylacetic acid methyl ester 219692-33-8 C10H11BrO3
3-bromo-5-methyl-4-hydroxyphenylacetic acid methyl ester
—— 2-[2-[(2-Hydroxy-5-methoxy-3-methylphenyl)methylideneamino]ethyliminomethyl]-4-methoxy-6-methylphenol 1449252-28-1 C20H24N2O4
2-[2-[(2-Hydroxy-5-methoxy-3-methylphenyl)methylideneamino]ethyliminomethyl]-4-methoxy-6-methylphenol
—— 2-benzothiazol-4-ylazo-4-methoxy-phenol 41228-97-1 C14H11N3O2S
2-benzothiazol-4-ylazo-4-methoxy-phenol
—— tris-(3,5-dibutyl-4-hydroxy-phenyl)-sulfonium ; chloride 122492-72-2 C42H63O3S*Cl
tris-(3,5-dibutyl-4-hydroxy-phenyl)-sulfonium ; chloride
—— 3,4-bis(nonyloxy)phenol 1277180-65-0 C24H42O3
3,4-bis(nonyloxy)phenol
—— 5-(2-hydroxy-4-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 886126-21-2 C12H10N2O4S
5-(2-hydroxy-4-methoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— 4-(1-Propyloctyl)-phenol 17508-61-1 C17H28O
4-(1-Propyloctyl)-phenol
—— 4-[4-(5-Chlorothiophen-2-yl)-2-ethylphenyl]-5-hydroxy-2,2,6,6-tetramethylpyran-3-one 1160559-60-3 C21H23ClO3S
4-[4-(5-Chlorothiophen-2-yl)-2-ethylphenyl]-5-hydroxy-2,2,6,6-tetramethylpyran-3-one
—— 5-(4-fluoro-2-hydroxy-benzylidene)-4-thioxo-thiazolidin-2-one 1181083-31-7 C10H6FNO2S2
5-(4-fluoro-2-hydroxy-benzylidene)-4-thioxo-thiazolidin-2-one
—— [manganes(III)(3-(2-hydroxyphenyl)-5-methyl-pyrazole(-H))2(3-(2-hydroxyphenyl)-5-methyl-pyrazole)(formate)] 1394369-69-7 C31H29MnN6O5
[manganes(III)(3-(2-hydroxyphenyl)-5-methyl-pyrazole(-H))2(3-(2-hydroxyphenyl)-5-methyl-pyrazole)(formate)]
—— 1-(5-Nitrosalicyliden)-4-isopropyl-thiosemicarbazon 41377-27-9 C11H14N4O3S
1-(5-Nitrosalicyliden)-4-isopropyl-thiosemicarbazon
—— 2,2'-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide) 75646-30-9 C22H22N6O6S3
2,2'-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide)
—— (E)-2-(((3,5-bis(trifluoromethyl)phenyl)imino)methyl)-4-nitrophenol 1431151-46-0 C15H8F6N2O3
(E)-2-(((3,5-bis(trifluoromethyl)phenyl)imino)methyl)-4-nitrophenol
—— Azepane-1-carbothioic acid S-(2-methoxy-5-methyl-benzyl) ester 36952-21-3 C16H23NO2S
Azepane-1-carbothioic acid S-(2-methoxy-5-methyl-benzyl) ester
—— 5-{[(E)-5-(2,4-Dichloro-5-fluoro-phenyl)-6H-[1,3,4]thiadiazin-2-ylimino]-methyl}-2-methoxy-phenol 905599-43-1 C17H12Cl2FN3O2S
5-{[(E)-5-(2,4-Dichloro-5-fluoro-phenyl)-6H-[1,3,4]thiadiazin-2-ylimino]-methyl}-2-methoxy-phenol
—— 4-[(6-amino-hexylamino)-methyl]-2-methoxy-phenol 1130609-12-9 C14H24N2O2
4-[(6-amino-hexylamino)-methyl]-2-methoxy-phenol
—— 1-(p-Hydroxyphenyl)-2-nitro-penten 1208-84-0 C11H13NO3
1-(p-Hydroxyphenyl)-2-nitro-penten
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[(3R)-3-hydroxypyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-50-7 C14H14N2O3S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[(3R)-3-hydroxypyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one