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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
—— (E)-ethyl 8-(3,5-dimethyl-4-hydroxyphenyl)-2-octenoate 144180-77-8 C18H26O3
(E)-ethyl 8-(3,5-dimethyl-4-hydroxyphenyl)-2-octenoate
—— N,N'-bis(3-Br-5-Cl-salicylidene)-1,2-diimino-2,2-dimethylethane 874274-53-0 C18H16Br2Cl2N2O2
N,N'-bis(3-Br-5-Cl-salicylidene)-1,2-diimino-2,2-dimethylethane
—— N,N'-dimethyl-N,N'-bis(2-hydroxy-5-nitrobenzyl)ethylenediamine 213775-51-0 C18H22N4O6
N,N'-dimethyl-N,N'-bis(2-hydroxy-5-nitrobenzyl)ethylenediamine
—— 2-(5-bromo-2-hydroxybenzilidene)-N-(prop-2-en-1-yl)hydrazinecarbothioamide 41377-20-2 C11H12BrN3OS
2-(5-bromo-2-hydroxybenzilidene)-N-(prop-2-en-1-yl)hydrazinecarbothioamide
—— (1E,3E)-1-(4-cyanophenyl)-4-(4-hydroxy-3-methoxyphenyl)-1,3-butadiene 1206103-22-1 C18H15NO2
(1E,3E)-1-(4-cyanophenyl)-4-(4-hydroxy-3-methoxyphenyl)-1,3-butadiene
—— 1-Benzyl-4-(3-chlor-4-hydroxy-benzyliden)-pyrrolidin-2,3-dion 21659-35-8 C18H14ClNO3
1-Benzyl-4-(3-chlor-4-hydroxy-benzyliden)-pyrrolidin-2,3-dion
—— N'-[(1E)-(m-hydroxy-p-methoxyphenyl)methylene]phosphorohydrazidic acid dipropyl ester 1237507-96-8 C14H23N2O5P
N'-[(1E)-(m-hydroxy-p-methoxyphenyl)methylene]phosphorohydrazidic acid dipropyl ester
—— 4-(5-heptyl-1,3,4-thiadiazol-2-yl)benzene-1,3-diol 1259435-11-4 C15H20N2O2S
4-(5-heptyl-1,3,4-thiadiazol-2-yl)benzene-1,3-diol
—— 2-(3,4-dihydroxyphenyl)-1,3,4-oxadiazole 1616086-43-1 C8H6N2O3
2-(3,4-dihydroxyphenyl)-1,3,4-oxadiazole
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-74-5 C15H15FN2O3S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— (4R,5S)-4-(5-fluoro-2-hydroxyphenyl)-3-(3-fluorophenyl)-5-[(1R)-1-hydroxy-3-phenylpropyl]-1,3-oxazolidin-2-one 1011265-25-0 C24H21F2NO4
(4R,5S)-4-(5-fluoro-2-hydroxyphenyl)-3-(3-fluorophenyl)-5-[(1R)-1-hydroxy-3-phenylpropyl]-1,3-oxazolidin-2-one
—— 7-(2,4-diethyl-5-hydroxyphenoxy)-2,2-dimethylheptanenitrile 1569982-36-0 C19H29NO2
7-(2,4-diethyl-5-hydroxyphenoxy)-2,2-dimethylheptanenitrile
—— 4-Bromo-5-chloro-2-pentyl-phenol 52016-75-8 C11H14BrClO
4-Bromo-5-chloro-2-pentyl-phenol
—— 2,4-bis-salicylidenamino-phenol 4588-99-2 C20H16N2O3
2,4-bis-salicylidenamino-phenol
—— 4-Methoxy-3-pyridin-4-ylmethyl-phenol 117896-17-0 C13H13NO2
4-Methoxy-3-pyridin-4-ylmethyl-phenol
—— N-{2-(3,4-dimethylbenzyloxy)ethyl}-4-hydroxy-3-methoxyphenylacetamide 192634-72-3 C20H25NO4
N-{2-(3,4-dimethylbenzyloxy)ethyl}-4-hydroxy-3-methoxyphenylacetamide
—— 2,4-Dihexanoylresorcin-bis-(phenylhydrazon) 5113-08-6 C30H38N4O2
2,4-Dihexanoylresorcin-bis-(phenylhydrazon)
—— 1022086-79-8 C16H17NO
—— [4-Hydroxy-3-(3-hydroxypropyl)-2,5,6-trimethylphenyl] thiocyanate 196944-53-3 C13H17NO2S
[4-Hydroxy-3-(3-hydroxypropyl)-2,5,6-trimethylphenyl] thiocyanate
—— 2-(trifluoromethyl)-1-(2-hydroxyphenyl)pyridin-4(1H)-one 1391764-05-8 C12H8F3NO2
2-(trifluoromethyl)-1-(2-hydroxyphenyl)pyridin-4(1H)-one
—— [(Z)-4-Hydroxy-phenylimino]-pyridin-2-yl-acetonitrile 477935-05-0 C13H9N3O
[(Z)-4-Hydroxy-phenylimino]-pyridin-2-yl-acetonitrile
—— 4-[2-(Cyclopentylmethoxy)ethyl]phenol 108007-99-4 C14H20O2
4-[2-(Cyclopentylmethoxy)ethyl]phenol
—— acetic acid-(4-hydroxy-2,5-dinitro-anilide) 871878-62-5 C8H7N3O6
acetic acid-(4-hydroxy-2,5-dinitro-anilide)
—— (2E)-2-((N'-(5,6-diphenyl-1,2,4-triazin-3-yl)carbamohydrazonoyl)imino)-3-(4-hydroxyphenyl)propanoic acid 113288-81-6 C25H21N7O3
(2E)-2-((N'-(5,6-diphenyl-1,2,4-triazin-3-yl)carbamohydrazonoyl)imino)-3-(4-hydroxyphenyl)propanoic acid
—— 4-[2-[bis(4-methylphenyl)methylidene]cyclobutyl]oxy-2,3,5,6-tetrachlorophenol 128742-49-4 C25H20Cl4O2
4-[2-[bis(4-methylphenyl)methylidene]cyclobutyl]oxy-2,3,5,6-tetrachlorophenol
—— 7-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dihydroxy-phenyl)-2-methoxy-bicyclo[3.3.1]non-2-ene-4,9-dione 945553-73-1 C22H30O6Si
7-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dihydroxy-phenyl)-2-methoxy-bicyclo[3.3.1]non-2-ene-4,9-dione
—— 2-Allyl-4-amino-3,5,6-trimethyl-phenol 859970-44-8 C12H17NO
2-Allyl-4-amino-3,5,6-trimethyl-phenol
—— 2-Hydroxy-5-methoxybenzaldehyde N-(3-chlorophenyl)thiosemicarbazone 769143-15-9 C15H14ClN3O2S
2-Hydroxy-5-methoxybenzaldehyde N-(3-chlorophenyl)thiosemicarbazone
—— 2-(difluoromethoxy)-4-fluorophenol 1261572-13-7 C7H5F3O2
2-(difluoromethoxy)-4-fluorophenol
—— tetraethyl 3,4-dihydroxyphenylbutylidenebisphosphonate 852449-55-9 C18H32O8P2
tetraethyl 3,4-dihydroxyphenylbutylidenebisphosphonate
—— 91815-30-4 C17H25NO3
—— bis-2,2'-(2-hydroxybenzylideneimino)diphenylditelluride 119307-23-2 C26H20N2O2Te2
bis-2,2'-(2-hydroxybenzylideneimino)diphenylditelluride
—— 5-(4-hydroxyphenyl)-1-azaspiro[5.5]undec-4-ene 158721-12-1 C16H21NO
5-(4-hydroxyphenyl)-1-azaspiro[5.5]undec-4-ene
—— 2-bromo-6-chloro-4-iodophenol 846040-36-6 C6H3BrClIO
2-bromo-6-chloro-4-iodophenol
—— 2-(1-ethyl-4,5-dihydro-1H-imidazol-2-yl)phenol 1239047-92-7 C11H14N2O
2-(1-ethyl-4,5-dihydro-1H-imidazol-2-yl)phenol
—— 1-(4-hydroxy-3-methoxy-phenyl)-2-oxo-propane-1-sulfonic acid , sodium-salt 33528-85-7 C10H11O6S*Na
1-(4-hydroxy-3-methoxy-phenyl)-2-oxo-propane-1-sulfonic acid , sodium-salt
—— 2-(4-tert-butyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)benzene-1,4-diol 123435-03-0 C15H20O5
2-(4-tert-butyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)benzene-1,4-diol
—— 4-(2,2-Dichloro-3,3,4,4-tetrafluoro-1-hydroxy-cyclobutyl)-phenol 2062-35-3 C10H6Cl2F4O2
4-(2,2-Dichloro-3,3,4,4-tetrafluoro-1-hydroxy-cyclobutyl)-phenol
—— 1,2-benzylidenedioxy-7-(2-hydroxybenzylideneamino)-4-azaheptane 503415-88-1 C20H24N2O3
1,2-benzylidenedioxy-7-(2-hydroxybenzylideneamino)-4-azaheptane
—— Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester 954370-67-3 C23H36O5
Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester
—— 3-(4-hydroxy-phenyl)-2-phenylimino-thiazolidin-4-one 51347-23-0 C15H12N2O2S
3-(4-hydroxy-phenyl)-2-phenylimino-thiazolidin-4-one
—— 2-{[(E)-2-Dimethylamino-ethylimino]-methyl}-4-methyl-6-{[(E)-2-pyridin-2-yl-ethylimino]-methyl}-phenol 135806-34-7 C20H26N4O
2-{[(E)-2-Dimethylamino-ethylimino]-methyl}-4-methyl-6-{[(E)-2-pyridin-2-yl-ethylimino]-methyl}-phenol
—— 1-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-acetone 815620-52-1 C12H16O4
1-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-acetone
—— 2-(3,4-diethyl-1-oxa-3-aza-spiro[4.5]dec-2-yl)-phenol 24135-33-9 C18H27NO2
2-(3,4-diethyl-1-oxa-3-aza-spiro[4.5]dec-2-yl)-phenol
—— (E)-4-phenyliminomethylbenzene-1,3-diol 15666-59-8 C13H11NO2
(E)-4-phenyliminomethylbenzene-1,3-diol
—— 4-[2-(3-cycloheptyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-62-0 C17H20N2O3
4-[2-(3-cycloheptyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 2-cyano-N-(3,4-dihydroxybenzyl)-3-[4-(2-pyridin-4-yl-trans-vinyl)-phenyl]-E-acrylamide 878795-76-7 C24H19N3O3
2-cyano-N-(3,4-dihydroxybenzyl)-3-[4-(2-pyridin-4-yl-trans-vinyl)-phenyl]-E-acrylamide
—— Methyl cis-[-4-cyano-4-(3-hydroxy-4-methoxyphenyl)cyclohexane-1-carboxylate] 153260-08-3 C16H19NO4
Methyl cis-[-4-cyano-4-(3-hydroxy-4-methoxyphenyl)cyclohexane-1-carboxylate]
—— N-(4-Chloro-2-methyl-phenyl)-2-hydroxy-3-nitro-thiobenzamide 23233-86-5 C14H11ClN2O3S
N-(4-Chloro-2-methyl-phenyl)-2-hydroxy-3-nitro-thiobenzamide
—— m-Triphenylsilyl-phenol 18737-99-0 C24H20OSi
m-Triphenylsilyl-phenol