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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
—— methyl [3-hydroxy-4-(4-hydroxyphenyl)-5-oxofuran-2(5H)-ylidene](4-hydroxyphenyl)acetate 54805-70-8 C19H14O7
methyl [3-hydroxy-4-(4-hydroxyphenyl)-5-oxofuran-2(5H)-ylidene](4-hydroxyphenyl)acetate
—— Bis(4-hydroxyphenyl)arsinous iodide 6309-82-6 C12H10AsIO2
Bis(4-hydroxyphenyl)arsinous iodide
—— 1-[2-(4-Hydroxy-phenyl)-ethyl]-pyrrolidin-2-one 85231-14-7 C12H15NO2
1-[2-(4-Hydroxy-phenyl)-ethyl]-pyrrolidin-2-one
—— N-ethyl-N-methylethanamine;2,4,6-trinitrophenol 6635-09-2 C11H16N4O7
N-ethyl-N-methylethanamine;2,4,6-trinitrophenol
—— Dimethylaminohydrochinon 50564-14-2 C8H11NO2
Dimethylaminohydrochinon
—— Dipyridin-3-yldiazene; 2,4,6-trinitrophenol 7249-69-6 C16H11N7O7
Dipyridin-3-yldiazene; 2,4,6-trinitrophenol
—— 2-{[bis-(2-chloro-ethyl)-amino]-methyl}-hydroquinone 91245-27-1 C11H15Cl2NO2
2-{[bis-(2-chloro-ethyl)-amino]-methyl}-hydroquinone
—— 4-(((2S,3S)-2-methyl-2-(prop-1-en-2-yl)tetrahydrofuran-3-yl)-methyl)phenol 1258500-57-0 C15H20O2
4-(((2S,3S)-2-methyl-2-(prop-1-en-2-yl)tetrahydrofuran-3-yl)-methyl)phenol
—— 4-(3-hydroxy-benzylidene)-3-phenyl-4<i>H</i>-isoxazol-5-one 54754-44-8 C16H11NO3
4-(3-hydroxy-benzylidene)-3-phenyl-4<i>H</i>-isoxazol-5-one
—— {4-[(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester 1247874-41-4 C50H73N5O13
{4-[(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
—— 4-Chloro-2-(hexadecyliminomethyl)phenol 6311-18-8 C23H38ClNO
4-Chloro-2-(hexadecyliminomethyl)phenol
—— normetanephrine hydrochloride 13062-62-9 C9H13NO3*ClH
normetanephrine hydrochloride
—— normetanephrine hydrochloride 29101-68-6 C9H13NO3*ClH
normetanephrine hydrochloride
—— 2,4,6-Trinitrophenol--decahydroisoquinoline (1/1) 6350-14-7 C15H20N4O7
2,4,6-Trinitrophenol--decahydroisoquinoline (1/1)
—— 4-(4-[1,2,3]-triazol-1-yl-but-1-ynyl)-phenol 864157-06-2 C12H11N3O
4-(4-[1,2,3]-triazol-1-yl-but-1-ynyl)-phenol
—— 4-(2-[1,2,3]Triazol-1-yl-ethanesulfonylmethyl)-phenol 864156-99-0 C11H13N3O3S
4-(2-[1,2,3]Triazol-1-yl-ethanesulfonylmethyl)-phenol
—— 2-Hydroxy-N-ethyl-thiobenzamid 4611-38-5 C9H11NOS
2-Hydroxy-N-ethyl-thiobenzamid
—— 4-(3-(1H-1,2,3-triazol-1-yl)propoxy)phenol 864157-10-8 C11H13N3O2
4-(3-(1H-1,2,3-triazol-1-yl)propoxy)phenol
—— 6-Bromo-4-(1,3-dioxolan-2-yl)-3-nitrobenzene-1,2-diol 1001433-48-2 C9H8BrNO6
6-Bromo-4-(1,3-dioxolan-2-yl)-3-nitrobenzene-1,2-diol
—— 4-(triisopropylsilyloxy)phenethyl 2-(3-ethylidene-2-oxotetrahydro-2H-pyran-4-yl)acetate 1160497-82-4 C26H40O5Si
4-(triisopropylsilyloxy)phenethyl 2-(3-ethylidene-2-oxotetrahydro-2H-pyran-4-yl)acetate
—— N(benzylamino)salicylphosphonic acid 61146-25-6 C14H16NO4P
N(benzylamino)salicylphosphonic acid
—— 4-(4-Methyl-1,3-dioxan-2-yl)phenol 902262-79-7 C11H14O3
4-(4-Methyl-1,3-dioxan-2-yl)phenol
—— Antineoplastic-44835 91461-36-8 C13H12AsNO4
Antineoplastic-44835
—— 1-[3-(4-hydroxy-3-methoxyphenyl)propyl]imidazole 202595-42-4 C13H16N2O2
1-[3-(4-hydroxy-3-methoxyphenyl)propyl]imidazole
—— 1-[3-(3-chloro-4-hydroxyphenyl)propyl]imidazole 202595-46-8 C12H13ClN2O
1-[3-(3-chloro-4-hydroxyphenyl)propyl]imidazole
—— 4-(4-(1H-1,2,3-triazol-1-yl)propyl)phenol 366016-83-3 C11H13N3O
4-(4-(1H-1,2,3-triazol-1-yl)propyl)phenol
—— 3-{1-[3-(3-hydroxyphenyl)propyl]-1H-imidazol-2-yl}-1,2-propanediol 366016-98-0 C15H20N2O3
3-{1-[3-(3-hydroxyphenyl)propyl]-1H-imidazol-2-yl}-1,2-propanediol
—— 3-[3-(1H-1,2,3-triazole-1-yl)propyl]phenol 366016-85-5 C11H13N3O
3-[3-(1H-1,2,3-triazole-1-yl)propyl]phenol
—— 4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenol Hydrochloride 854935-04-9 C13H17NO2*ClH
4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenol Hydrochloride
—— 3-(4-chloro-2-hydroxyphenyl)propanenitrile 942268-23-7 C9H8ClNO
3-(4-chloro-2-hydroxyphenyl)propanenitrile
—— 4-hydroxyphenyl boronic acid pinacol ester 1106870-09-0 C12H19BO4
4-hydroxyphenyl boronic acid pinacol ester
—— 4'-hydroxy[1,2-13C2]phenylacetic acid 680182-22-3 C8H8O3
4'-hydroxy[1,2-13C2]phenylacetic acid
—— methyl 2-(4-fluoro-3-hydroxyphenyl)acetate 628333-62-0 C9H9FO3
methyl 2-(4-fluoro-3-hydroxyphenyl)acetate
—— ethyl 3-(3'-hydroxy-4'-methoxyphenyl)propanoate 84428-16-0 C12H16O4
ethyl 3-(3'-hydroxy-4'-methoxyphenyl)propanoate
—— (4S)-4-benzyl-3-[(2S)-3-(3-hydroxyphenyl)-2-isopropoxypropionyl]-1,3-oxazolidin-2-one 478929-76-9 C22H25NO5
(4S)-4-benzyl-3-[(2S)-3-(3-hydroxyphenyl)-2-isopropoxypropionyl]-1,3-oxazolidin-2-one
—— 4-[(Cyclohexylimino)methyl]phenol 58336-73-5 C13H17NO
4-[(Cyclohexylimino)methyl]phenol
—— 4-[1,3,5-Tricyclohexyl-4,6-bis(4-hydroxyphenyl)-1,3,5-triazinan-2-yl]phenol 6640-88-6 C39H51N3O3
4-[1,3,5-Tricyclohexyl-4,6-bis(4-hydroxyphenyl)-1,3,5-triazinan-2-yl]phenol
—— 2,4,6-Tris[(benzylamino)methyl]benzene-1,3,5-triol 7248-55-7 C30H33N3O3
2,4,6-Tris[(benzylamino)methyl]benzene-1,3,5-triol
—— 6-(2-hydroxy-5-methylphenyl)-1-methyl-1,4,5,6-tetrahydropyridine-3-carbonitrile 94008-34-1 C14H16N2O
6-(2-hydroxy-5-methylphenyl)-1-methyl-1,4,5,6-tetrahydropyridine-3-carbonitrile
—— 2,5-bis(benzylaminomethyl)hydroquinone 6342-13-8 C22H24N2O2
2,5-bis(benzylaminomethyl)hydroquinone
—— 2-[[Cyclohexyl-[(2-hydroxy-3-nitrophenyl)methyl]amino]methyl]-6-nitrophenol 6342-11-6 C20H23N3O6
2-[[Cyclohexyl-[(2-hydroxy-3-nitrophenyl)methyl]amino]methyl]-6-nitrophenol
—— 2-(4,5-dihydroxy-3-methoxyphenyl)ethylamine hydrochloride 5090-25-5 C9H13NO3*ClH
2-(4,5-dihydroxy-3-methoxyphenyl)ethylamine hydrochloride
—— 2,4,6-Tris[(benzylamino)methyl]benzene-1,3-diol 6638-80-8 C30H33N3O2
2,4,6-Tris[(benzylamino)methyl]benzene-1,3-diol
—— 4-bromo-2-(t-butyldimethylsilyloxymethyl)phenol 475275-93-5 C13H21BrO2Si
4-bromo-2-(t-butyldimethylsilyloxymethyl)phenol
—— 2-(4-tert-butylbenzyl)-3-[2-(4-hydroxy-3-iodo-5-methoxyphenyl)acetamido]propyl pivalate 1258845-64-5 C28H38INO5
2-(4-tert-butylbenzyl)-3-[2-(4-hydroxy-3-iodo-5-methoxyphenyl)acetamido]propyl pivalate
—— N-[3-(cyclohexen-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide 478400-46-3 C21H23NO3
N-[3-(cyclohexen-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide
—— N-heptyl-N-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide 1400943-50-1 C16H25NO4
N-heptyl-N-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— 2-(3-benzyloxy-4-methoxyphenyl)ethyl methanesulfonate 68360-40-7 C17H20O5S
2-(3-benzyloxy-4-methoxyphenyl)ethyl methanesulfonate
—— 2-(3-hydroxy-4-methoxyphenyl)ethyl acetate 945530-95-0 C11H14O4
2-(3-hydroxy-4-methoxyphenyl)ethyl acetate
—— 2-(2-Hydroxyphenyl)-4,5,5-trimethyl-3-oxazolin-N-oxid 28741-09-5 C12H15NO3
2-(2-Hydroxyphenyl)-4,5,5-trimethyl-3-oxazolin-N-oxid