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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
—— 2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate 953422-35-0 C11H14O5
2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate
—— 2-benzyloxy-6-methoxy-hydroquinone 858218-65-2 C14H14O4
2-benzyloxy-6-methoxy-hydroquinone
—— 3,4-bis[(2-furylmethyl)sulfanyl]-6-methylcatechol 923267-52-1 C17H16O4S2
3,4-bis[(2-furylmethyl)sulfanyl]-6-methylcatechol
—— 3,5-bis[(2-furylmethyl)sulfanyl]-6-methylcatechol 923267-53-2 C17H16O4S2
3,5-bis[(2-furylmethyl)sulfanyl]-6-methylcatechol
—— calopin 475503-78-7 C13H16O5
calopin
—— 3-(cyclohex-1-en-3-yl)-6-methylbenzene-1,2-diol 1229193-36-5 C13H16O2
3-(cyclohex-1-en-3-yl)-6-methylbenzene-1,2-diol
—— (E)-3-acetyl-6-(4-hydroxy-3-methoxyphenyl)-5-hexen-2-one 94956-21-5 C16H20O5
(E)-3-acetyl-6-(4-hydroxy-3-methoxyphenyl)-5-hexen-2-one
—— 3-[(2-furylmethyl)sulfanyl]-6-methylcatechol 923267-51-0 C12H12O3S
3-[(2-furylmethyl)sulfanyl]-6-methylcatechol
—— Methyl 7-(3,5-dimethoxy-4-hydroxyphenyl)-3-oxoheptanoate 118630-92-5 C16H22O6
Methyl 7-(3,5-dimethoxy-4-hydroxyphenyl)-3-oxoheptanoate
—— 2,6-Dimethoxy-4-[1-((Z)-3-phenyl-allyloxy)-allyl]-phenol 84700-96-9 C20H22O4
2,6-Dimethoxy-4-[1-((Z)-3-phenyl-allyloxy)-allyl]-phenol
—— 4-(1-Ethoxy-allyl)-2,6-dimethoxy-phenol 84700-94-7 C13H18O4
4-(1-Ethoxy-allyl)-2,6-dimethoxy-phenol
—— 4-(1-Benzyloxy-allyl)-2,6-dimethoxy-phenol 84700-95-8 C18H20O4
4-(1-Benzyloxy-allyl)-2,6-dimethoxy-phenol
—— 3-(4-hydroxy-3,5-dimethoxyphenyl)-2-methylpropanal 1352129-31-7 C12H16O4
3-(4-hydroxy-3,5-dimethoxyphenyl)-2-methylpropanal
—— N,N'-bis(3-hydroxysalicylidene)ethane-1,2-diamine 146559-04-8 C16H16N2O4
N,N'-bis(3-hydroxysalicylidene)ethane-1,2-diamine
—— 2,2',3,3'-tetrahydroxybenzaldazine 203194-56-3 C14H12N2O4
2,2',3,3'-tetrahydroxybenzaldazine
—— 6-chloro-N-1-(4-methylphenyl)butyllpyrazin-2-amine 708253-68-3 C22H25N3O2
6-chloro-N-1-(4-methylphenyl)butyllpyrazin-2-amine
—— 6-bromo-2-fluoro-3-pentyl-phenol 743466-97-9 C11H14BrFO
6-bromo-2-fluoro-3-pentyl-phenol
—— 4-[2-Methyl-3-(4-methylphenyl)-3,4-dihydropyrazol-5-yl]benzene-1,3-diol 1453488-26-0 C17H18N2O2
4-[2-Methyl-3-(4-methylphenyl)-3,4-dihydropyrazol-5-yl]benzene-1,3-diol
—— 2-(2-hydroxy-5-methyl-phenyl)-2-methyl-3-<i>o</i>-tolyl-thiazolidin-4-one 60161-11-7 C18H19NO2S
2-(2-hydroxy-5-methyl-phenyl)-2-methyl-3-<i>o</i>-tolyl-thiazolidin-4-one
—— 2-(5-Thiophen-2-yl-3,4-dihydro-2H-pyrazol-3-yl)-phenol 131557-35-2 C13H12N2OS
2-(5-Thiophen-2-yl-3,4-dihydro-2H-pyrazol-3-yl)-phenol
—— 2,4-Diphenyl-3-(p-hydroxyphenyl)-furan 54756-50-2 C22H16O2
2,4-Diphenyl-3-(p-hydroxyphenyl)-furan
—— 3-benzyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one 60121-33-7 C18H19NO2S
3-benzyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one
—— 3,4-Diphenyl-2-(p-hydroxyphenyl)-furan 54756-49-9 C22H16O2
3,4-Diphenyl-2-(p-hydroxyphenyl)-furan
—— Pyrrolidine, 1-(2,6-dimethoxybenzyl)-, picrate 58395-75-8 C19H22N4O9
Pyrrolidine, 1-(2,6-dimethoxybenzyl)-, picrate
—— 2-Chloro-4-(2-cyclopropylamino-1-hydroxy-ethyl)-phenol 58498-04-7 C11H14ClNO2
2-Chloro-4-(2-cyclopropylamino-1-hydroxy-ethyl)-phenol
—— 4-(4-methyl-4-n-propyl-4-silacyclohexyl)phenol 177787-20-1 C15H24OSi
4-(4-methyl-4-n-propyl-4-silacyclohexyl)phenol
—— N-dimethylaminomethylene-2-hydroxy-4-nitro-benzenesulfonamide 936920-31-9 C9H11N3O5S
N-dimethylaminomethylene-2-hydroxy-4-nitro-benzenesulfonamide
—— 3-butyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one 60121-34-8 C15H21NO2S
3-butyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one
—— (+/-)-1-(4-hydroxyphenoxy)-4-(3-pyridyl)-2-butanol 192376-95-7 C15H17NO3
(+/-)-1-(4-hydroxyphenoxy)-4-(3-pyridyl)-2-butanol
—— 3-cyclohexyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one 60161-10-6 C17H23NO2S
3-cyclohexyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one
—— 5-(3-bromo-4-hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-oxazolidin-4-one 1275574-84-9 C16H10BrNO3S
5-(3-bromo-4-hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-oxazolidin-4-one
—— 2-(2-hydroxy-5-methyl-phenyl)-2-methyl-3-<i>m</i>-tolyl-thiazolidin-4-one 60121-32-6 C18H19NO2S
2-(2-hydroxy-5-methyl-phenyl)-2-methyl-3-<i>m</i>-tolyl-thiazolidin-4-one
—— 3-(2-chloro-phenyl)-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one 60158-82-9 C17H16ClNO2S
3-(2-chloro-phenyl)-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one
—— 4-Hydroxy-5-methoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde 499217-06-0 C14H19BO5
4-Hydroxy-5-methoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde
—— 2-methyl-4-{[4-(4-pyridinyl)-1,3-thiazol-2-yl]amino}phenol 1187668-77-4 C15H13N3OS
2-methyl-4-{[4-(4-pyridinyl)-1,3-thiazol-2-yl]amino}phenol
—— 4-chloro-2-fluoro-6-iodophenol 1192815-08-9 C6H3ClFIO
4-chloro-2-fluoro-6-iodophenol
—— 4-allyl-5-bromo-2-methoxyphenol 5746-38-3 C10H11BrO2
4-allyl-5-bromo-2-methoxyphenol
—— 5-[2-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethoxy-6-methyl-phenylethynyl]-2-methoxy-phenol 192809-53-3 C24H32O5Si
5-[2-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethoxy-6-methyl-phenylethynyl]-2-methoxy-phenol
—— 3-bromo-6-methoxy-2-(2-methylallyl)phenol 185406-75-1 C11H13BrO2
3-bromo-6-methoxy-2-(2-methylallyl)phenol
—— Phenol, 5-butyl-2-methoxy- 134319-00-9 C11H16O2
Phenol, 5-butyl-2-methoxy-
—— 3-bromo-2-cyclopent-1-enylmethyl-6-methoxyphenol 185244-56-8 C13H15BrO2
3-bromo-2-cyclopent-1-enylmethyl-6-methoxyphenol
—— Sylvopinolmonoacetat 30891-30-6 C10H12O4
Sylvopinolmonoacetat
—— 2,4-dibromo-5-chloro-6-methoxyphenol 602326-16-9 C7H5Br2ClO2
2,4-dibromo-5-chloro-6-methoxyphenol
—— 4,4'-(thiene-2,3-diyl)diphenol 1078733-93-3 C16H12O2S
4,4'-(thiene-2,3-diyl)diphenol
—— 4-(1-hydroxycyclobutyl)phenol 1234665-22-5 C10H12O2
4-(1-hydroxycyclobutyl)phenol
—— methyl (E)-2-(4-hydroxybenzylidene)hydrazine-1-carboxylate 89005-64-1 C9H10N2O3
methyl (E)-2-(4-hydroxybenzylidene)hydrazine-1-carboxylate
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-oxazolidin-4-one 1181081-66-2 C10H7NO3S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-oxazolidin-4-one
—— 1,11-bis(5-cyano-2,4-dihydroxyphenyl)-4,8-dioxaundecane 491610-81-2 C23H26N2O6
1,11-bis(5-cyano-2,4-dihydroxyphenyl)-4,8-dioxaundecane
—— 2-tert.-Butyl-6-methyl-4-methoxy-phenol 26307-56-2 C12H18O2
2-tert.-Butyl-6-methyl-4-methoxy-phenol
—— 2-methoxy-5-hydroxyphenylacetic acid 81720-88-9 C9H10O4
2-methoxy-5-hydroxyphenylacetic acid