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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-Hydroxyphenyl)ethyl 2-cyanoacetate 132465-18-0 C11H11NO3
2-(4-Hydroxyphenyl)ethyl 2-cyanoacetate
—— 2,4-diiodo-5-methoxyresorcinol 134810-56-3 C7H6I2O3
2,4-diiodo-5-methoxyresorcinol
—— 2-(2-Tetrahydrofuryl-methyl)-phenol 32857-59-3 C11H14O2
2-(2-Tetrahydrofuryl-methyl)-phenol
—— 4-methyl-2-[1-(2-morpholin-4-yl-ethylamino)-ethyl]-phenol 46982-03-0 C15H24N2O2
4-methyl-2-[1-(2-morpholin-4-yl-ethylamino)-ethyl]-phenol
—— 2,3-dimethyl-3-(2-hydroxy-4-methylphenyl)cyclopent-1-ene 81603-53-4 C14H18O
2,3-dimethyl-3-(2-hydroxy-4-methylphenyl)cyclopent-1-ene
—— 2-(4-hydroxyphenyl)-5-(4-hydroxy-2-methylphenyl)-1,3,4-oxadiazole 1402231-36-0 C15H12N2O3
2-(4-hydroxyphenyl)-5-(4-hydroxy-2-methylphenyl)-1,3,4-oxadiazole
—— 2,4-Bis(2'-(3-methoxy-4-hydroxyphenyl)-5'-carboxymethyl-4'-thiazolidinon-3'-yl)-6-hydroxypyrimidine 138799-74-3 C28H26N4O11S2
2,4-Bis(2'-(3-methoxy-4-hydroxyphenyl)-5'-carboxymethyl-4'-thiazolidinon-3'-yl)-6-hydroxypyrimidine
—— 3-nitro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzene-1,2-diol hydrochloride 1222881-52-8 C13H8N4O5*ClH
3-nitro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzene-1,2-diol hydrochloride
—— 3H-(Methoxy-3-hydroxy-4-benzyl)-3-dimethyl-2,3-indole 28193-55-7 C18H19NO2
3H-(Methoxy-3-hydroxy-4-benzyl)-3-dimethyl-2,3-indole
—— 2,4-Bis-(2'-hydroxybenzalamino)-6-hydroxypyrimidine 137205-99-3 C18H14N4O3
2,4-Bis-(2'-hydroxybenzalamino)-6-hydroxypyrimidine
—— (2S,4R,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol 1292847-88-1 C18H24O5
(2S,4R,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol
—— 4-[(2,4-Diamino-6-methylsulfanylpyrimidin-5-yl)methyl]-2,6-dimethylphenol 73576-18-8 C14H18N4OS
4-[(2,4-Diamino-6-methylsulfanylpyrimidin-5-yl)methyl]-2,6-dimethylphenol
—— 4-(2-p-tolylhydrazono)-1-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one 1456804-31-1 C21H18N8O4S
4-(2-p-tolylhydrazono)-1-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one
—— 6-O-(2-hydroxy-3-methoxybenzylideneamino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 130639-83-7 C20H27NO8
6-O-(2-hydroxy-3-methoxybenzylideneamino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
—— 6-Chloro-2-(1-imidazol-1-yl-vinyl)-3-methyl-phenol 85456-98-0 C12H11ClN2O
6-Chloro-2-(1-imidazol-1-yl-vinyl)-3-methyl-phenol
—— [Zn(HO(C6H3)(NCH(C6H3)(O)(OCH3))2)(pyridine)] 1237438-51-5 C27H23N3O5Zn
[Zn(HO(C6H3)(NCH(C6H3)(O)(OCH3))2)(pyridine)]
—— 5-methoxy-1,4-dimethyl-1,2,3,4-tetrahydroquinoxaline-5,8-diol 1375149-00-0 C11H16N2O3
5-methoxy-1,4-dimethyl-1,2,3,4-tetrahydroquinoxaline-5,8-diol
—— N-(p-Methoxy-o-hydroxybenzylidene)-m-aminopyridine 188945-60-0 C13H12N2O2
N-(p-Methoxy-o-hydroxybenzylidene)-m-aminopyridine
—— 1-(3-Hydroxyphenyl)cyclopropanecarboxylic acid 1056933-73-3 C10H10O3
1-(3-Hydroxyphenyl)cyclopropanecarboxylic acid
—— trimethyltin 2-(((E)-1-(2-hydroxyphenyl)ethylidene)amino)acetate 466664-06-2 C13H19NO3Sn
trimethyltin 2-(((E)-1-(2-hydroxyphenyl)ethylidene)amino)acetate
—— 4-((S)-hydroxy((2S)-1-methylpiperidin-2-yl)methyl)phenol 1007109-91-2 C13H19NO2
4-((S)-hydroxy((2S)-1-methylpiperidin-2-yl)methyl)phenol
—— 4-methoxy-2-(4-methylphenyliminomethyl)phenol 20772-69-4 C15H15NO2
4-methoxy-2-(4-methylphenyliminomethyl)phenol
—— 2854-72-0 C21H17N3O4S
—— Phen-2,3,5,6-d4-ol 143134-41-2 C6H6O
Phen-2,3,5,6-d4-ol
—— 2,6-Heptamethyl-phenol 57787-29-8 C13H18O
2,6-Heptamethyl-phenol
—— 4-nitro-2-(4,5,6,7-tetrahydro-benzothiazol-2-ylsulfanylmethyl)-phenol 25222-53-1 C14H14N2O3S2
4-nitro-2-(4,5,6,7-tetrahydro-benzothiazol-2-ylsulfanylmethyl)-phenol
—— N<sup>1</sup>-Carbobenzoxyglycin-N<sup>2</sup>-<2,3,4-trihydroxy-benzyliden>-hydrazid 28342-55-4 C17H17N3O6
N<sup>1</sup>-Carbobenzoxyglycin-N<sup>2</sup>-<2,3,4-trihydroxy-benzyliden>-hydrazid
—— 4-(3,4-dihyro-2H-pyran-5-ylmethyl)-2,6-dimethylphenol 1335223-59-0 C14H18O2
4-(3,4-dihyro-2H-pyran-5-ylmethyl)-2,6-dimethylphenol
—— 2-(2-Hydroxy-4-nitro-phenyl-hydrazono)-3-oxo-buttersaeureaethylester 5352-24-9 C12H13N3O6
2-(2-Hydroxy-4-nitro-phenyl-hydrazono)-3-oxo-buttersaeureaethylester
—— C-(5-chloro-2-hydroxyphenyl)-N-(2-hydroxyphenylmethyl)nitrone 219655-05-7 C14H12ClNO3
C-(5-chloro-2-hydroxyphenyl)-N-(2-hydroxyphenylmethyl)nitrone
—— 3-(Benzooxazol-2-ylamino)-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one 136713-12-7 C24H18N4O4
3-(Benzooxazol-2-ylamino)-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one
—— 5-(dimethyl-tert-butylsilyl)oxy-2-methoxy-3,4-dimethylphenol 1352754-57-4 C15H26O3Si
5-(dimethyl-tert-butylsilyl)oxy-2-methoxy-3,4-dimethylphenol
—— 4-(11-Bromo-undecyl)-benzene-1,2-diol 34728-08-0 C17H27BrO2
4-(11-Bromo-undecyl)-benzene-1,2-diol
—— 2-(5-(4-fluorobenzyl)-4-methyl-4H-1,2,4-triazol-3-yl)-3-hydroxy-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one 1289649-11-1 C19H20FN5O3
2-(5-(4-fluorobenzyl)-4-methyl-4H-1,2,4-triazol-3-yl)-3-hydroxy-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one
—— 6,6'-(1E,1'E)-(propane-1,2-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2,4-diiodophenol) 1088976-76-4 C17H14I4N2O2
6,6'-(1E,1'E)-(propane-1,2-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2,4-diiodophenol)
—— 5-(4-hydroxy-phenyl)-3-trichloromethylsulfanyl-3<i>H</i>-[1,3,4]oxadiazol-2-one 1026-53-5 C9H5Cl3N2O3S
5-(4-hydroxy-phenyl)-3-trichloromethylsulfanyl-3<i>H</i>-[1,3,4]oxadiazol-2-one
—— 4-(1-hydrazineylidenedodecyl)phenol 1089701-01-8 C18H30N2O
4-(1-hydrazineylidenedodecyl)phenol
—— 4-iodo-3,6-dimethyl-1,2-benzenediol 110364-43-7 C8H9IO2
4-iodo-3,6-dimethyl-1,2-benzenediol
—— 3-Pentadecyl-6-<dimethylamino-methyl>-brenzcatechin 16273-29-3 C24H43NO2
3-Pentadecyl-6-<dimethylamino-methyl>-brenzcatechin
—— 2-Diethylamino-4.6-bis-(2.4-dihydroxyphenyl)-1.3.5-triazin 1853-74-3 C19H20N4O4
2-Diethylamino-4.6-bis-(2.4-dihydroxyphenyl)-1.3.5-triazin
—— 53055-34-8 C16H18O4S2
—— 1-(4-hydroxy-phenyl)-3,6-dimethyl-1<i>H</i>-pyridazin-4-one 72755-00-1 C12H12N2O2
1-(4-hydroxy-phenyl)-3,6-dimethyl-1<i>H</i>-pyridazin-4-one
—— [N,N'-bis-(2-hydroxy-5-nitrobenzyl)hydrazine] 1374227-18-5 C14H14N4O6
[N,N'-bis-(2-hydroxy-5-nitrobenzyl)hydrazine]
—— 2,6-Dibromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol 250284-80-1 C12H14Br2O3
2,6-Dibromo-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol
—— N'-(3-Hydroxy-benzyl)-hydrazinecarboxylic acid ethyl ester 91761-26-1 C10H14N2O3
N'-(3-Hydroxy-benzyl)-hydrazinecarboxylic acid ethyl ester
—— N(1)-cyano-N(2)-[2-(3,4-dihydroxyphenyl)ethyl]guanidine 1143565-59-6 C10H12N4O2
N(1)-cyano-N(2)-[2-(3,4-dihydroxyphenyl)ethyl]guanidine
—— N-(5-Chloro-2-hydroxy-3-methyl-benzyl)-acrylamide 13579-32-3 C11H12ClNO2
N-(5-Chloro-2-hydroxy-3-methyl-benzyl)-acrylamide
—— 3(4-Ethoxy-benzyl)-2-(2-hydroxy-6-methoxy-phenyl)-thiazolidin-4-one 1255933-39-1 C19H21NO4S
3(4-Ethoxy-benzyl)-2-(2-hydroxy-6-methoxy-phenyl)-thiazolidin-4-one
—— Methyl(2-hydroxy-α,3-dimethoxybenzyl)methyl-carbamat 23121-79-1 C12H17NO5
Methyl(2-hydroxy-α,3-dimethoxybenzyl)methyl-carbamat
—— tert-butyl N-[(1R,2S)-1-hydroxy-1-(2-hydroxy-5-methoxyphenyl)propan-2-yl]carbamate 123172-83-8 C15H23NO5
tert-butyl N-[(1R,2S)-1-hydroxy-1-(2-hydroxy-5-methoxyphenyl)propan-2-yl]carbamate