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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-(4,4-bishydroperoxy-pentyl)phenol —— C11H16O5
2-(4,4-bishydroperoxy-pentyl)phenol
—— 2-((4-hydroxy-3-methoxybenzyl)amino)-2-oxoethyl heptanoate —— C17H25NO5
2-((4-hydroxy-3-methoxybenzyl)amino)-2-oxoethyl heptanoate
—— 2-(2-n-octylethynyl)phenol —— C16H22O
2-(2-n-octylethynyl)phenol
—— 2-[(2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol —— C17H19NO2
2-[(2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol
—— 2-[(2S,4S,5S)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol —— C17H19NO2
2-[(2S,4S,5S)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol
—— 6-undecyl-1,2,4-trihydroxybenzene —— C17H28O3
6-undecyl-1,2,4-trihydroxybenzene
—— 1,2-calix[7]-crown-2 —— C79H100O7
1,2-calix[7]-crown-2
—— methyl 2-(3-(benzyloxy)-4,5-dihydroxyphenyl)acetate —— C16H16O5
methyl 2-(3-(benzyloxy)-4,5-dihydroxyphenyl)acetate
—— (R)-(-)-2-[(2-benzyloxyethyl)-4,5-dimethoxybenzylidine]-tert-butylsulfinamide —— C22H29NO4S
(R)-(-)-2-[(2-benzyloxyethyl)-4,5-dimethoxybenzylidine]-tert-butylsulfinamide
—— (S)-(+)-2-[(2-tert-butyldimethylsiloxyethyl)-4,5-dimethoxybenzylidine]-p-toluenesulfinamide —— C24H35NO4SSi
(S)-(+)-2-[(2-tert-butyldimethylsiloxyethyl)-4,5-dimethoxybenzylidine]-p-toluenesulfinamide
—— N-(3-hydroxy-4-methoxybenzyl)benzo[d]thiazole-2-carboxamide —— C16H14N2O3S
N-(3-hydroxy-4-methoxybenzyl)benzo[d]thiazole-2-carboxamide
—— N-(4-hydroxy-3-methoxybenzyl)-N'-hexylthiourea —— C15H24N2O2S
N-(4-hydroxy-3-methoxybenzyl)-N'-hexylthiourea
—— (R)-N-(2-hydroxy-3-methoxybenzyl)-1-phenylethylamine —— C16H19NO2
(R)-N-(2-hydroxy-3-methoxybenzyl)-1-phenylethylamine
—— 1-Allyl-3-[1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-4,5,5-trimethyl-pyrrolidin-2-one —— C17H21NO2
1-Allyl-3-[1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-4,5,5-trimethyl-pyrrolidin-2-one
—— 4-Benzyloxy-5-bromo-2-methoxyphenol —— C14H13BrO3
4-Benzyloxy-5-bromo-2-methoxyphenol
—— 4-hydroxybenzyl n-decyl thioether —— C17H28OS
4-hydroxybenzyl n-decyl thioether
—— hydroxytyrosyl palmitate —— C24H40O4
hydroxytyrosyl palmitate
—— 4-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-phenol —— C15H13NO2
4-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-phenol
—— α-(aminomethyl)-(3-chloro-4-hydroxyphenyl)methanol —— C8H10ClNO2
α-(aminomethyl)-(3-chloro-4-hydroxyphenyl)methanol
—— 2-[(3,5-dinitropyridin-2-yl)amino]-5-methoxyphenol —— C12H10N4O6
2-[(3,5-dinitropyridin-2-yl)amino]-5-methoxyphenol
—— acetophenonidene-2-hydroxyaniline —— C14H13NO
acetophenonidene-2-hydroxyaniline
—— (+/-)-3-((R*)-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)(6-chloro-3-pyridyl)methyl)phenol —— C21H26ClN3O
(+/-)-3-((R*)-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)(6-chloro-3-pyridyl)methyl)phenol
—— 4-hydroxy-4-(2-hydroxyphenyl)butan-2-one —— C10H12O3
4-hydroxy-4-(2-hydroxyphenyl)butan-2-one
—— 2-(4-hydroxy-3-methoxyphenyl)-N-{cis-4-[(E)-1-pentenyl]cyclohexyl}acetamide —— C20H29NO3
2-(4-hydroxy-3-methoxyphenyl)-N-{cis-4-[(E)-1-pentenyl]cyclohexyl}acetamide
—— 2-Methoxy-3,6-dimethyl-phenol —— C9H12O2
2-Methoxy-3,6-dimethyl-phenol
—— (4-hydroxy-2-nitrophenylamino)methyl-dimethylphosphonate —— C9H13N2O6P
(4-hydroxy-2-nitrophenylamino)methyl-dimethylphosphonate
—— 4-[2-[bis[(dimethoxyphosphinyl)methyl]amino]ethyl]phenol —— C14H25NO7P2
4-[2-[bis[(dimethoxyphosphinyl)methyl]amino]ethyl]phenol
—— 4-cyclopropylpropoxy-phenol —— C12H16O2
4-cyclopropylpropoxy-phenol
—— (4S,5R,6R)-5-Acetylamino-4-amino-6-{[2-(4-hydroxyphenyl)ethyl] propylcarbamoyl}-5,6-dihydro-4H-pyran-2-carboxylic acid trifluoroacetate salt —— C2HF3O2*C20H27N3O6
(4S,5R,6R)-5-Acetylamino-4-amino-6-{[2-(4-hydroxyphenyl)ethyl] propylcarbamoyl}-5,6-dihydro-4H-pyran-2-carboxylic acid trifluoroacetate salt
—— 1,5-bis(2,4-dihydroxyphenylmethylketone)carbohydrazone —— C17H18N4O5
1,5-bis(2,4-dihydroxyphenylmethylketone)carbohydrazone
—— 3-(2-methyl-1,3-dioxolan-2-yl)phenol —— C10H12O3
3-(2-methyl-1,3-dioxolan-2-yl)phenol
—— 2-bromo-4-amino-5-fluorophenol —— C6H5BrFNO
2-bromo-4-amino-5-fluorophenol
—— (2,3-dihydroxy-4-methoxy-phenyl)-(1,2,3-trimethoxy-8,9-dihydro-7H-benzocyclohepten-5-yl)-methanone —— C22H24O7
(2,3-dihydroxy-4-methoxy-phenyl)-(1,2,3-trimethoxy-8,9-dihydro-7H-benzocyclohepten-5-yl)-methanone
—— (2E,5E)-2-[(4-tert-butylphenyl)methylidene]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one —— C24H26O3
(2E,5E)-2-[(4-tert-butylphenyl)methylidene]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one
—— 5-tert-butyl-N'-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-(2-hydroxyphenyl)-N-(2-thien-2ylethyl)-1,3,4-thiadiazole-3(2H)-carboximidamide —— C25H32N6OS3
5-tert-butyl-N'-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-(2-hydroxyphenyl)-N-(2-thien-2ylethyl)-1,3,4-thiadiazole-3(2H)-carboximidamide
—— (E)-3-(3-hydroxy-4-methoxyphenyl)-2-((3,4,5-trimethoxyphenyl)sulfonyl)acrylonitrile —— C19H19NO7S
(E)-3-(3-hydroxy-4-methoxyphenyl)-2-((3,4,5-trimethoxyphenyl)sulfonyl)acrylonitrile
—— 10-(4-hydroxy-3-methoxy-phenyl)-decanoic acid —— C17H26O4
10-(4-hydroxy-3-methoxy-phenyl)-decanoic acid
—— 3-(4-hydroxyphenyl)oxetan-3-ol —— C9H10O3
3-(4-hydroxyphenyl)oxetan-3-ol
—— 1-oxyl-2-(4-hydroxy-3-methoxyphenyl)-4,4,5,5-tetramethyl-2-imidazoline —— C14H19N2O3
1-oxyl-2-(4-hydroxy-3-methoxyphenyl)-4,4,5,5-tetramethyl-2-imidazoline
—— 4,4'-(((bis(2-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-silanediyl)bis(oxy))bis(ethane-2,1-diyl))diphenol —— C38H44O8Si
4,4'-(((bis(2-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-silanediyl)bis(oxy))bis(ethane-2,1-diyl))diphenol
—— 4-hydroxy-α,2-dimethylbenzenemethanol —— C9H12O2
4-hydroxy-α,2-dimethylbenzenemethanol
—— diethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate —— C21H27NO7
diethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— 3,4,5-trihydroxy-N'-(3-((2-methoxybenzyl)oxy)benzylidene)benzohydrazide —— C22H20N2O6
3,4,5-trihydroxy-N'-(3-((2-methoxybenzyl)oxy)benzylidene)benzohydrazide
—— (E)-3,4,5-trihydroxy-N'-(3-(2-methoxybenzyloxy)phenylmethylidene)benzohydrazide —— C22H20N2O6
(E)-3,4,5-trihydroxy-N'-(3-(2-methoxybenzyloxy)phenylmethylidene)benzohydrazide
—— m-Chlorbenzaldehyd-O-(5-chlor-2-hydroxybenzyl)-oxim —— C14H11Cl2NO2
m-Chlorbenzaldehyd-O-(5-chlor-2-hydroxybenzyl)-oxim
—— methyl 2-(2-hydroxy-5-ethoxyphenyl)acetate —— C11H14O4
methyl 2-(2-hydroxy-5-ethoxyphenyl)acetate
—— 2-(((2-(pyridin-2-yl)ethyl)amino)methyl)-4-methoxyphenol —— C15H18N2O2
2-(((2-(pyridin-2-yl)ethyl)amino)methyl)-4-methoxyphenol
—— (4-hydroxy-phenyl)-thiocarbamic acid <i>O</i>-butyl ester —— C11H15NO2S
(4-hydroxy-phenyl)-thiocarbamic acid <i>O</i>-butyl ester
—— 3-chloro-4-hydroxy-benzaldehyde-semicarbazone —— C8H8ClN3O2
3-chloro-4-hydroxy-benzaldehyde-semicarbazone
—— thio-m-cresol —— C7H6OS
thio-m-cresol