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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
—— N-((2S)-tetrahydrofurfuryl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276703-28-7 C11H13ClN2O6S
N-((2S)-tetrahydrofurfuryl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— 3-fluoro-4-[6-(1-hydroxymethyl-propylamino)-pyrazin-2-yl]-phenol 1617545-64-8 C14H16FN3O2
3-fluoro-4-[6-(1-hydroxymethyl-propylamino)-pyrazin-2-yl]-phenol
—— rac-1-(2-Hydroxy-5-methoxy-3,4,6-trimethylphenethyl)-1-methylallyl acetate 133185-69-0 C18H26O4
rac-1-(2-Hydroxy-5-methoxy-3,4,6-trimethylphenethyl)-1-methylallyl acetate
—— 2,5-dibromo-3,4-dimethyl-phenol 63113-35-9 C8H8Br2O
2,5-dibromo-3,4-dimethyl-phenol
—— (+)-2-(((2R,4R)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)methyl)phenol 1177258-95-5 C39H56O4Si2
(+)-2-(((2R,4R)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)methyl)phenol
—— 2-Amino-5-fluoro-4-iodophenol 1037298-25-1 C6H5FINO
2-Amino-5-fluoro-4-iodophenol
—— 2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-hydroxybenzylidene)cyclopentanone 1393829-66-7 C19H14Br2O3
2-(3,5-dibromo-4-hydroxybenzylidene)-5-(4-hydroxybenzylidene)cyclopentanone
—— 5-(1-hydroxypentyl)benzene-1,3-diol 71186-12-4 C11H16O3
5-(1-hydroxypentyl)benzene-1,3-diol
—— phenolsuccinein 4374-58-7 C16H14O4
phenolsuccinein
—— 3-(1-Phenylguanidino)-propionsaeurebutylester-pikrat 100185-49-7 C6H3N3O7*C14H21N3O2
3-(1-Phenylguanidino)-propionsaeurebutylester-pikrat
—— 2-<5-Methyl-4-imidazolylazo>-4-methoxy-phenol 13182-98-4 C11H12N4O2
2-<5-Methyl-4-imidazolylazo>-4-methoxy-phenol
—— 4-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-4,5,7,8-tetrahydrofuro[3',4':5,6]pyrido[3,2-d]isoxazol-5-one 1380423-09-5 C22H18N2O6
4-(3-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-4,5,7,8-tetrahydrofuro[3',4':5,6]pyrido[3,2-d]isoxazol-5-one
—— 4-hydroxy-3-methyl-benzaldehyde-oxime 203711-10-8 C8H9NO2
4-hydroxy-3-methyl-benzaldehyde-oxime
—— 3-[2'-hydroxy-5'-nitrophenyl]-1,2-benzisoxazole 1316277-26-5 C13H8N2O4
3-[2'-hydroxy-5'-nitrophenyl]-1,2-benzisoxazole
—— N-(3-Chloro-4-hydroxy-benzyl)-propionamide 34190-49-3 C10H12ClNO2
N-(3-Chloro-4-hydroxy-benzyl)-propionamide
—— 3,5-Bis-dodecylsulfanylmethyl-2,4,6-trimethyl-phenol 23500-83-6 C35H64OS2
3,5-Bis-dodecylsulfanylmethyl-2,4,6-trimethyl-phenol
—— 2,3,6-trimethyl-4-[(dibutylphenylsilyl)methylthio]phenol 1230389-93-1 C24H36OSSi
2,3,6-trimethyl-4-[(dibutylphenylsilyl)methylthio]phenol
—— 5-(3-Iodopropyl)-2-methoxyphenol 197382-88-0 C10H13IO2
5-(3-Iodopropyl)-2-methoxyphenol
—— 2-chloro-4-[6-((R)-2-hydroxy-1-phenyl-ethylamino)-pyrazin-2-yl]-phenol 1617545-80-8 C18H16ClN3O2
2-chloro-4-[6-((R)-2-hydroxy-1-phenyl-ethylamino)-pyrazin-2-yl]-phenol
—— 2-chloro-6-trifluoromethane-(34S)-sulfonylphenol 1043912-35-1 C7H4ClF3O3S
2-chloro-6-trifluoromethane-(34S)-sulfonylphenol
—— 5-(4,5-dihydroxy-2-methoxyphenyl)-2,2-dimethyl[1,3]dioxane-4,6-dione 1448465-03-9 C13H14O7
5-(4,5-dihydroxy-2-methoxyphenyl)-2,2-dimethyl[1,3]dioxane-4,6-dione
—— 6-(5-chloro-2-hydroxy-4-methyl-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one 62902-46-9 C11H11ClN2O2
6-(5-chloro-2-hydroxy-4-methyl-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— <i>N</i>,<i>N</i>'''-(4-hydroxy-<i>m</i>-phenylene)-di-guanidine 4405-09-8 C8H12N6O
<i>N</i>,<i>N</i>'''-(4-hydroxy-<i>m</i>-phenylene)-di-guanidine
—— 2-(3,4-dihydroxyphenyl)-1-(3,4-dimethoxyphenethyl)-1,5-dihydro-6H-imidazo[4,5-g]quinoxalin-6-one 1170675-59-8 C25H22N4O5
2-(3,4-dihydroxyphenyl)-1-(3,4-dimethoxyphenethyl)-1,5-dihydro-6H-imidazo[4,5-g]quinoxalin-6-one
—— Acetic acid 4-[(E)-benzyloxyimino]-5-hydroxy-1,3,4,8b-tetrahydro-2H-biphenylen-4a-yl ester 126538-67-8 C21H21NO4
Acetic acid 4-[(E)-benzyloxyimino]-5-hydroxy-1,3,4,8b-tetrahydro-2H-biphenylen-4a-yl ester
—— <i>N</i>,<i>N</i>-bis-(2-hydroxy-ethyl)-<i>N</i>-(4-hydroxy-phenyl)-hydrazinium; chloride 118923-75-4 C10H17N2O3*Cl
<i>N</i>,<i>N</i>-bis-(2-hydroxy-ethyl)-<i>N</i>-(4-hydroxy-phenyl)-hydrazinium; chloride
—— 3-[Cyclohexyl-(3-hydroxyphenyl)phosphoryl]phenol 72835-32-6 C18H21O3P
3-[Cyclohexyl-(3-hydroxyphenyl)phosphoryl]phenol
—— Laurenisol 23526-39-8 C15H19BrO
Laurenisol
—— H2tbhsOMe 1097884-24-6 C15H14N2O2S
H2tbhsOMe
—— 3-Methoxy-4-hydroxy-benzaldehyd-(4-o-tolyl-thiosemicarbazon) 740-82-9 C16H17N3O2S
3-Methoxy-4-hydroxy-benzaldehyd-(4-o-tolyl-thiosemicarbazon)
—— tert-butyl N-[2-(2-hydroxy-5-methoxyphenyl)ethyl]-carbamate 939985-83-8 C14H21NO4
tert-butyl N-[2-(2-hydroxy-5-methoxyphenyl)ethyl]-carbamate
—— 4-[2-(3-ethyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-18-6 C12H12N2O3
4-[2-(3-ethyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 2,5'-dihydroxy-3,4'-dimethoxy-2',5-bis-(1-methylethyl)biphenyl 1309765-10-3 C20H26O4
2,5'-dihydroxy-3,4'-dimethoxy-2',5-bis-(1-methylethyl)biphenyl
—— (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol 783332-55-8 C14H20O3
(Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol
—— Phenol, 2,3-difluoro-6-iodo- 186590-28-3 C6H3F2IO
Phenol, 2,3-difluoro-6-iodo-
—— N,N′-bis(salicyliden)-2,3-diaminopyridine 189822-35-3 C19H15N3O2
N,N′-bis(salicyliden)-2,3-diaminopyridine
—— 16-Methyl-heptadecanoic acid 4-hydroxy-benzylamide 25566-75-0 C25H43NO2
16-Methyl-heptadecanoic acid 4-hydroxy-benzylamide
—— (R)-tert-butyl 5-(4-hydroxyphenyl)pentane-1,2-diyl dicarbamate 1160754-97-1 C21H34N2O5
(R)-tert-butyl 5-(4-hydroxyphenyl)pentane-1,2-diyl dicarbamate
—— N-[2-(2-Bromo-5-hydroxy-4-methoxy-phenyl)-ethyl]-2-(4-methoxy-phenyl)-acetamide 32549-66-9 C18H20BrNO4
N-[2-(2-Bromo-5-hydroxy-4-methoxy-phenyl)-ethyl]-2-(4-methoxy-phenyl)-acetamide
—— picric acid*2-bromopyridine 78947-67-8 C5H4BrN*C6H3N3O7
picric acid*2-bromopyridine
—— (E)-2-(3-methyloct-2-en-6-yn-1-yl)phenol 1120349-74-7 C15H18O
(E)-2-(3-methyloct-2-en-6-yn-1-yl)phenol
—— 1-(3-Hydroxy-benzyl)-2-isopropyliden-hydrazin 40051-72-7 C10H14N2O
1-(3-Hydroxy-benzyl)-2-isopropyliden-hydrazin
—— (3,5-dimethyl-isoxazol-4-yl)-(2-hydroxy-5-methyl-phenyl)-methanone oxime 27129-36-8 C13H14N2O3
(3,5-dimethyl-isoxazol-4-yl)-(2-hydroxy-5-methyl-phenyl)-methanone oxime
—— (3S)-1-amino-3-(3-(dec-1-ynyl)-4-methoxyphenyl)cyclopentanecarboxylic acid 1036391-47-5 C23H33NO3
(3S)-1-amino-3-(3-(dec-1-ynyl)-4-methoxyphenyl)cyclopentanecarboxylic acid
—— N-γ-(2',5'-Dihydroxyphenyl)propylpyridiniumbromid 32782-91-5 Br*C14H16NO2
N-γ-(2',5'-Dihydroxyphenyl)propylpyridiniumbromid
—— 2,3-dihydroxybenzaldehyde-4-ethyl-3-thiosemicarbazone 500888-73-3 C10H13N3O2S
2,3-dihydroxybenzaldehyde-4-ethyl-3-thiosemicarbazone
—— 3-(2,4-dihydroxybenzyl)-N-heptyl-4-hydroxybutanamide 1515406-24-2 C18H29NO4
3-(2,4-dihydroxybenzyl)-N-heptyl-4-hydroxybutanamide
—— 5-(2-hydroxy-5-methylphenyl)-2,3-dihydro-1,4-diazepine 90380-32-8 C12H14N2O
5-(2-hydroxy-5-methylphenyl)-2,3-dihydro-1,4-diazepine
—— 2-hydroxy-N-(m-tolylmethyl)benzenecarbothioamide 1132646-11-7 C15H15NOS
2-hydroxy-N-(m-tolylmethyl)benzenecarbothioamide
—— (E)-2-(((4,6-dimethylpyridin-2-yl)imino)methyl)phenol 90440-99-6 C14H14N2O
(E)-2-(((4,6-dimethylpyridin-2-yl)imino)methyl)phenol