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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
—— 6-[2-[bis(dimethylamino)phosphoryl]-1-hydroxypropyl]-3-chlorobenzene-1,2,4-triol 113524-11-1 C13H22ClN2O5P
6-[2-[bis(dimethylamino)phosphoryl]-1-hydroxypropyl]-3-chlorobenzene-1,2,4-triol
—— 6-Brom-5-hydroxy-2-oxo-4,7-dimethyl-1,3-benzoxathiol 92707-28-3 C9H7BrO3S
6-Brom-5-hydroxy-2-oxo-4,7-dimethyl-1,3-benzoxathiol
—— (1R,2S)-2-methylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate 1193988-28-1 C22H32N2O5
(1R,2S)-2-methylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate
—— 2,5-Di-<4-hydroxy-3-methoxy-phenyl>-1,4-dioxan 98437-98-0 C18H20O6
2,5-Di-<4-hydroxy-3-methoxy-phenyl>-1,4-dioxan
—— 183267-31-4 C14H17ClN2O2
—— 3-hydroxy-4-(3-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-5-propyl-1,5-dihydro-pyrrol-2-one 1024606-57-2 C19H23N3O3
3-hydroxy-4-(3-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-5-propyl-1,5-dihydro-pyrrol-2-one
—— vanillidene-p-dimethylaminoaniline dihydrochloride 10545-77-4 C16H18N2O2*2ClH
vanillidene-p-dimethylaminoaniline dihydrochloride
—— 1357481-55-0 C23H26O4
—— 3-Bromo-4-(1,3-dioxolan-2-yl)-2-methoxyphenol 404356-74-7 C10H11BrO4
3-Bromo-4-(1,3-dioxolan-2-yl)-2-methoxyphenol
—— 10,11-dihydroxy-dibenzo[<i>a,d</i>]cyclohepten-5-one 100954-06-1 C15H10O3
10,11-dihydroxy-dibenzo[<i>a,d</i>]cyclohepten-5-one
—— 1537890-29-1 C21H30NO4P
—— isopropyl (S)-2-(2,5-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylate 945635-16-5 C14H17NO4S
isopropyl (S)-2-(2,5-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylate
—— 4-((3-Bromo-4-hydroxy-5-methoxybenzylidene)amino)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione 478253-74-6 C14H11BrN4O3S
4-((3-Bromo-4-hydroxy-5-methoxybenzylidene)amino)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione
—— 5<i>t</i>-(2,5-dihydroxy-4-methoxy-phenyl)-penta-2<i>t</i>,4-dienoic acid methyl ester 106381-27-5 C13H14O5
5<i>t</i>-(2,5-dihydroxy-4-methoxy-phenyl)-penta-2<i>t</i>,4-dienoic acid methyl ester
—— 4-Hydroxy-dithiobenzoesaeure-(carboxy-methylester) 17144-00-2 C9H8O3S2
4-Hydroxy-dithiobenzoesaeure-(carboxy-methylester)
—— 4-Methyl-6-(o-hydroxy-phenyl)-Δ<sup>3</sup>-tetrahydro-benzoesaeure 107619-58-9 C14H16O3
4-Methyl-6-(o-hydroxy-phenyl)-Δ<sup>3</sup>-tetrahydro-benzoesaeure
—— Thiophene-2-sulfonic acid (2-hydroxy-3,5-dinitro-phenyl)-amide 13335-65-4 C10H7N3O7S2
Thiophene-2-sulfonic acid (2-hydroxy-3,5-dinitro-phenyl)-amide
—— 1-Salicylidenaminooxy-decan 101745-41-9 C17H27NO2
1-Salicylidenaminooxy-decan
—— 3-[(dimethylamino)methyl]-2,4,5-trihydroxybenzaldehyde 1033038-00-4 C10H13NO4
3-[(dimethylamino)methyl]-2,4,5-trihydroxybenzaldehyde
—— 2-((R)-((R)-5,5-dimethyltetrahydrofuran-2-yl)(hydroxy)methyl)phenol 1197983-30-4 C13H18O3
2-((R)-((R)-5,5-dimethyltetrahydrofuran-2-yl)(hydroxy)methyl)phenol
—— 4-(3-acetoxypropyl)-2-methoxy-6-bromophenol 201361-84-4 C12H15BrO4
4-(3-acetoxypropyl)-2-methoxy-6-bromophenol
—— bis(isonicotinamidosalicylaldimine)dinitratodioxouranium(VI) 155642-14-1 C26H22N8O12U
bis(isonicotinamidosalicylaldimine)dinitratodioxouranium(VI)
—— 5,11,17-Tribromotetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9,11,13(20),15(19),16-nonaene-19,20,21-triol 83153-61-1 C21H15Br3O3
5,11,17-Tribromotetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9,11,13(20),15(19),16-nonaene-19,20,21-triol
—— Deterenol acetate 1644449-83-1 C13H21NO4
Deterenol acetate
—— (4-Chloro-phenylamino)-acetic acid N'-(4-hydroxy-3-methoxy-benzyl)-hydrazide 93548-72-2 C16H18ClN3O3
(4-Chloro-phenylamino)-acetic acid N'-(4-hydroxy-3-methoxy-benzyl)-hydrazide
—— salophen 1026018-63-2 C20H16N2O2
salophen
—— N-cyclohexyl-N-ethyl-4-hydroxy-3-nitro-benzamide 1235991-34-0 C15H20N2O4
N-cyclohexyl-N-ethyl-4-hydroxy-3-nitro-benzamide
—— 3-methyl-2-((pyridin-2-ylmethylene)amino)phenol 1257094-57-7 C13H12N2O
3-methyl-2-((pyridin-2-ylmethylene)amino)phenol
—— [(3-hydroxy-phenyl)-(5-oxo-3-phenyl-2,5-dihydro-isoxazol-4-yl)-methyl]-malononitrile 54754-32-4 C19H13N3O3
[(3-hydroxy-phenyl)-(5-oxo-3-phenyl-2,5-dihydro-isoxazol-4-yl)-methyl]-malononitrile
—— (Z)-methyl N-2-bromo-4,6-dimethylphenylbenzimidate 1402939-09-6 C16H16BrNO
(Z)-methyl N-2-bromo-4,6-dimethylphenylbenzimidate
—— 2-[5-(4-Chloro-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-methyl-phenol 86691-09-0 C22H19ClN2O
2-[5-(4-Chloro-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-methyl-phenol
—— 4-(4,5-dihydro-1<i>H</i>-imidazol-2-ylmethyl)-2-methoxy-phenol 111665-72-6 C11H14N2O2
4-(4,5-dihydro-1<i>H</i>-imidazol-2-ylmethyl)-2-methoxy-phenol
—— 3-methoxy-2,6-di(1-methyl-2-butenyl)phenol 95414-67-8 C17H24O2
3-methoxy-2,6-di(1-methyl-2-butenyl)phenol
—— p-(β-Cyclopentylidenethyl)phenol 60513-99-7 C13H16O
p-(β-Cyclopentylidenethyl)phenol
—— 2-methyl-3,6-dinitrophenol 132228-35-4 C7H6N2O5
2-methyl-3,6-dinitrophenol
—— 3-(2-hydroxy-5-methylphenyl)-5-methyl-4,5-dihydro-1H-pyrazole-1-carbothioamide 1267528-43-7 C12H15N3OS
3-(2-hydroxy-5-methylphenyl)-5-methyl-4,5-dihydro-1H-pyrazole-1-carbothioamide
—— 5-methoxy-2-((2-(3-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol 1421930-28-0 C15H13F3N2O2
5-methoxy-2-((2-(3-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol
—— 2-Aminomethyl-6-chloro-3,5-dimethoxy-4-methyl-phenol 38946-47-3 C10H14ClNO3
2-Aminomethyl-6-chloro-3,5-dimethoxy-4-methyl-phenol
—— 2-[(3-Butynoxyimino)methyl]-4,5-dichlorophenol 103743-28-8 C11H9Cl2NO2
2-[(3-Butynoxyimino)methyl]-4,5-dichlorophenol
—— 4-[dibromo-(4-hydroxy-3-methylphenyl)-λ4-tellanyl]-2-methylphenol 78106-50-0 C14H14Br2O2Te
4-[dibromo-(4-hydroxy-3-methylphenyl)-λ4-tellanyl]-2-methylphenol
—— (Z)-diisopropyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-(3-pyridyl)-amino]-vinylphosphonate 407582-95-0 C21H29N2O5P
(Z)-diisopropyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-(3-pyridyl)-amino]-vinylphosphonate
—— 2-chloro-N-[1-(2-hydroxy-3-methoxyphenyl)ethylideneamino]benzamide 1235578-22-9 C16H15ClN2O3
2-chloro-N-[1-(2-hydroxy-3-methoxyphenyl)ethylideneamino]benzamide
—— 2,6-di-tert-butyl-4-((2-hydroxy-3-nitrobenzylidene)amino)phenol 80039-14-1 C21H26N2O4
2,6-di-tert-butyl-4-((2-hydroxy-3-nitrobenzylidene)amino)phenol
—— 4-Fluoro-2-[(1-methyl-2-propynoxyimino)methyl]phenol 103743-20-0 C11H10FNO2
4-Fluoro-2-[(1-methyl-2-propynoxyimino)methyl]phenol
—— 6-(2-hydroxy-5-methoxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one 39499-69-9 C11H12N2O3
6-(2-hydroxy-5-methoxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— [4]pyridyl-acetic acid vanillylidenehydrazide 101091-70-7 C15H15N3O3
[4]pyridyl-acetic acid vanillylidenehydrazide
—— bis(5-methylsalicylaldehyde)semicarbazone 1214247-36-5 C17H17N3O3
bis(5-methylsalicylaldehyde)semicarbazone
—— 4-hydroxy-5-methoxy-isophthalaldehyde-bis-(2-methyl-isonicotinoylhydrazone) 122472-76-8 C23H22N6O4
4-hydroxy-5-methoxy-isophthalaldehyde-bis-(2-methyl-isonicotinoylhydrazone)
—— (4-Hydroxy-benzyl)-cyclobutan 104175-14-6 C11H14O
(4-Hydroxy-benzyl)-cyclobutan
—— (E)-2-(2-chloro-4-hydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide 1206228-04-7 C14H12ClN3OS
(E)-2-(2-chloro-4-hydroxybenzylidene)-N-phenylhydrazine-1-carbothioamide