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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-[1-[2-[3-(4-(2-Isobutoxy-ethyl)-phenoxy)-2-hydroxypropylamino]-ethyl]benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone 133154-92-4 C28H37N5O4
6-[1-[2-[3-(4-(2-Isobutoxy-ethyl)-phenoxy)-2-hydroxypropylamino]-ethyl]benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone
—— caffeic acid 142039-77-8 C9H10O2
caffeic acid
—— 6-[4-[3-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]propoxy]-3-methyl-phenyl]-4,5-dihydro-3(2H)-pyridazinone 133154-50-4 C29H41N3O5
6-[4-[3-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]propoxy]-3-methyl-phenyl]-4,5-dihydro-3(2H)-pyridazinone
—— 4-Methoxy-3,6-di-t-butylpyrocatechol 62783-44-2 C15H24O3
4-Methoxy-3,6-di-t-butylpyrocatechol
—— 4-isohexyl-pyrocatechol 688334-58-9 C12H18O2
4-isohexyl-pyrocatechol
—— 4-chloro-3,6-di-tert-butylpyrocatechol 80284-11-3 C14H21ClO2
4-chloro-3,6-di-tert-butylpyrocatechol
—— 4-Perfluorobutyl-1,2-benzenediol 134285-02-2 C10H5F9O2
4-Perfluorobutyl-1,2-benzenediol
—— 3-[(4-Hydroxy-3-methoxyphenyl)methylidene]-5-(4-methylphenyl)furan-2-one 84023-81-4 C19H16O4
3-[(4-Hydroxy-3-methoxyphenyl)methylidene]-5-(4-methylphenyl)furan-2-one
—— 6-[4-[2-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]ethoxy]-3-chloro-phenyl]-4,5-dihydro-3(2H)-pyridazinone 133154-56-0 C27H36ClN3O5
6-[4-[2-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]ethoxy]-3-chloro-phenyl]-4,5-dihydro-3(2H)-pyridazinone
—— 6-[4-[3-[3-(4-(2-Isobutoxyethyl)phenoxy)-2-hydroxypropylamino]propylsulphonyl]phenyl]-4,5-dihydro-3(2H)-pyridazinone 133155-13-2 C28H39N3O6S
6-[4-[3-[3-(4-(2-Isobutoxyethyl)phenoxy)-2-hydroxypropylamino]propylsulphonyl]phenyl]-4,5-dihydro-3(2H)-pyridazinone
—— 2-dodecylbenzene-1,4-diol 4595-23-7 C18H30O2
2-dodecylbenzene-1,4-diol
—— 6-[3-[2-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]ethoxy]phenyl]-4,5-dihydro-3(2H)-pyridazinone 133154-72-0 C27H37N3O5
6-[3-[2-[3-(4-(2-Isobutoxy-ethyl)phenoxy)-2-hydroxypropylamino]ethoxy]phenyl]-4,5-dihydro-3(2H)-pyridazinone
—— (5R,7R)-5-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ol 132127-59-4 C18H18O6
(5R,7R)-5-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ol
—— 1,4-Dihydroxy-2-furfuryl-benzol 91344-69-3 C11H10O3
1,4-Dihydroxy-2-furfuryl-benzol
—— 4-[(5R,7R)-7-cyclohexyloxy-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenol 132127-66-3 C24H28O6
4-[(5R,7R)-7-cyclohexyloxy-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenol
—— (5R,7S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ol 132127-59-4 C18H18O6
(5R,7S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ol
—— 4-[(5R,7S)-7-cyclohexyloxy-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenol 132127-66-3 C24H28O6
4-[(5R,7S)-7-cyclohexyloxy-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenol
—— 2-chloro-4-<2-<(2-phenylethyl)oxy>ethoxy>phenol 81228-24-2 C16H17ClO3
2-chloro-4-<2-<(2-phenylethyl)oxy>ethoxy>phenol
—— 4-<2-<(2-phenylethyl)oxy>ethoxy>-2-cresol 81227-91-0 C17H20O3
4-<2-<(2-phenylethyl)oxy>ethoxy>-2-cresol
—— 2-chloro-3,5,6-trimethylphenol 90416-29-8 C9H11ClO
2-chloro-3,5,6-trimethylphenol
—— 2-chloro-3,4,5-trimethylphenol 38941-96-7 C9H11ClO
2-chloro-3,4,5-trimethylphenol
—— 4-[1-Hydroxy-2-(3-hydroxy-1-methyl-propylamino)-ethyl]-benzene-1,2-diol 785732-45-8 C12H19NO4
4-[1-Hydroxy-2-(3-hydroxy-1-methyl-propylamino)-ethyl]-benzene-1,2-diol
—— 4,5-Dichloro-3-[(4-fluorophenyl)methoxy]-6-hydroxybenzene-1,2-dicarbonitrile 1374789-50-0 C15H7Cl2FN2O2
4,5-Dichloro-3-[(4-fluorophenyl)methoxy]-6-hydroxybenzene-1,2-dicarbonitrile
—— 2,6-bis((1H-1,2,4-triazol-1-yl)methyl)-4-methylphenol 845255-47-2 C13H14N6O
2,6-bis((1H-1,2,4-triazol-1-yl)methyl)-4-methylphenol
—— 3-(o-Hydroxyphenyl)butyronitril 65050-49-9 C10H11NO
3-(o-Hydroxyphenyl)butyronitril
—— 3,4,5-trihydroxybenzylamine hydroiodide 79490-74-7 C7H9NO3*HI
3,4,5-trihydroxybenzylamine hydroiodide
—— 2,6-Dimethyl-4-<4-<(trimethylsilyl)methyl>-4-pentenyl>phenol 118630-76-5 C17H28OSi
2,6-Dimethyl-4-<4-<(trimethylsilyl)methyl>-4-pentenyl>phenol
—— (E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-[(3,4,5-trihydroxyphenyl)methyl]but-2-enethioamide 1198078-68-0 C17H16BrNO5S
(E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-[(3,4,5-trihydroxyphenyl)methyl]but-2-enethioamide
—— 28-Amino-5,11,17,23-tetratert-butyl-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-25,26,27-triol 947514-01-4 C40H49NO3S4
28-Amino-5,11,17,23-tetratert-butyl-2,8,14,20-tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-25,26,27-triol
—— 6,12,18,24-Tetratert-butyl-2-oxa-9,15,21,27-tetrathiahexacyclo[20.3.1.14,25.110,14.116,20.03,8]nonacosa-1(25),3(8),4,6,10,12,14(29),16(28),17,19,22(26),23-dodecaene-26,28,29-triol 1197928-81-6 C40H46O4S4
6,12,18,24-Tetratert-butyl-2-oxa-9,15,21,27-tetrathiahexacyclo[20.3.1.14,25.110,14.116,20.03,8]nonacosa-1(25),3(8),4,6,10,12,14(29),16(28),17,19,22(26),23-dodecaene-26,28,29-triol
—— rigidiusculamide B 1196976-94-9 C13H15NO4
rigidiusculamide B
—— (S)-4-(4-hydroxybenzyl)-3-propionyloxazolidin-2-one 191105-59-6 C13H15NO4
(S)-4-(4-hydroxybenzyl)-3-propionyloxazolidin-2-one
—— 2,6-Dimethyl-4-<4,4-bis(ethoxycarbonyl)-6-<(trimethylsilyl)methyl>-6-heptenyl>phenol 118630-79-8 C25H40O5Si
2,6-Dimethyl-4-<4,4-bis(ethoxycarbonyl)-6-<(trimethylsilyl)methyl>-6-heptenyl>phenol
—— 4,4’-(hexane-1,6-diyl)bis(benzene-1,2-diol) 94265-62-0 C18H22O4
4,4’-(hexane-1,6-diyl)bis(benzene-1,2-diol)
—— 2-amino-4,5-dimethoxyphenol 7107-04-2 C8H11NO3
2-amino-4,5-dimethoxyphenol
—— tert-butyl N-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-(4-hydroxyphenyl)ethyl]carbamate 250281-91-5 C19H33NO4Si
tert-butyl N-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-(4-hydroxyphenyl)ethyl]carbamate
—— tert-butyl N-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3,5-dibromo-4-hydroxyphenyl)ethyl]carbamate 250281-93-7 C19H31Br2NO4Si
tert-butyl N-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3,5-dibromo-4-hydroxyphenyl)ethyl]carbamate
—— 3,6-bis[(2-furylmethyl)sulfanyl]-4-methylcatechol 923267-57-6 C17H16O4S2
3,6-bis[(2-furylmethyl)sulfanyl]-4-methylcatechol
—— mono-pentadecylphenol 68593-72-6 C21H36O
mono-pentadecylphenol
—— 4-(cyclohex-1-en-3-yl)-5-methylbenzene-1,2-diol 1229193-38-7 C13H16O2
4-(cyclohex-1-en-3-yl)-5-methylbenzene-1,2-diol
—— 3,4-bis[(2-furylmethyl)sulfanyl]-5-methylcatechol 923267-56-5 C17H16O4S2
3,4-bis[(2-furylmethyl)sulfanyl]-5-methylcatechol
—— 3-[(2-furylmethyl)sulfanyl]-5-methylcatechol 923267-55-4 C12H12O3S
3-[(2-furylmethyl)sulfanyl]-5-methylcatechol
—— 3-(cyclohex-1-en-3-yl)-5-methylbenzene-1,2-diol 1229193-37-6 C13H16O2
3-(cyclohex-1-en-3-yl)-5-methylbenzene-1,2-diol
—— 2,6-Dimethyl-4-(3-methylidenecyclopentyl)phenol 118630-78-7 C14H18O
2,6-Dimethyl-4-(3-methylidenecyclopentyl)phenol
—— 2-hydroxy-4-methyl-6-(2,2,2-trifluoro-1-hydroxyethyl)phenol 1321914-90-2 C9H9F3O3
2-hydroxy-4-methyl-6-(2,2,2-trifluoro-1-hydroxyethyl)phenol
—— 2-n-pentadecylhydroquinone 53918-51-7 C21H36O2
2-n-pentadecylhydroquinone
—— 6-Methyl-3-pentadecyl-brenzcatechin 16273-18-0 C22H38O2
6-Methyl-3-pentadecyl-brenzcatechin
—— 4,5,6-Trimethyl-3-pentadecyl-brenzcatechin 16273-19-1 C24H42O2
4,5,6-Trimethyl-3-pentadecyl-brenzcatechin
—— 4,5-Dimethyl-3-pentadecyl-brenzcatechin 7771-22-4 C23H40O2
4,5-Dimethyl-3-pentadecyl-brenzcatechin
—— 5-[3-(4-hydroxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione 178610-54-3 C13H15NO5
5-[3-(4-hydroxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione