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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
—— [(3-hydroxy-4-chlorophenyl)(2-methoxy(D3))methylene]-adamantane 552848-01-8 C18H21ClO2
[(3-hydroxy-4-chlorophenyl)(2-methoxy(D3))methylene]-adamantane
—— 2,4-dibromo-6-{{(2-(2-pyridyl)ethyl)imino}methyl}phenol 112359-99-6 C14H12Br2N2O
2,4-dibromo-6-{{(2-(2-pyridyl)ethyl)imino}methyl}phenol
—— 2,3-Dichloro-5-methylbenzene-1,4-diol 157824-94-7 C7H6Cl2O2
2,3-Dichloro-5-methylbenzene-1,4-diol
—— 2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenol hydrochloride 107355-48-6 C9H7Cl2NO2*ClH
2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenol hydrochloride
—— 100308-39-2 C30H28Cl2N8O6Sb*Cl
—— 1-(1-ethyl-1<i>H</i>-benzoimidazol-2-yl)-5-(2-hydroxy-4,6-dinitro-phenyl)-3-methyl-formazan 34689-64-0 C17H16N8O5
1-(1-ethyl-1<i>H</i>-benzoimidazol-2-yl)-5-(2-hydroxy-4,6-dinitro-phenyl)-3-methyl-formazan
—— (E)-2-(2-hydroxy-4-(thiophen-2-yl)but-3-en-2-yl)phenol 1273578-94-1 C14H14O2S
(E)-2-(2-hydroxy-4-(thiophen-2-yl)but-3-en-2-yl)phenol
—— [2-(2-Hydroxy-phenyl)-4-oxo-thiazolidin-3-yl]-thiourea 137609-06-4 C10H11N3O2S2
[2-(2-Hydroxy-phenyl)-4-oxo-thiazolidin-3-yl]-thiourea
—— 2-benzylsulfanyl-4-methyl-phenol 861315-17-5 C14H14OS
2-benzylsulfanyl-4-methyl-phenol
—— N'-(2-hydroxybenzylidene)-P,P-diphenylphosphinic hydrazide 49789-47-1 C19H17N2O2P
N'-(2-hydroxybenzylidene)-P,P-diphenylphosphinic hydrazide
—— 4-bromo-2-((((2-pyridyl)ethyl)imino)methyl)phenol 112359-98-5 C14H13BrN2O
4-bromo-2-((((2-pyridyl)ethyl)imino)methyl)phenol
—— 2-(3,4-Dimethoxyphenyl)ethyl cyclopentanecarboxylate 1607820-42-7 C16H22O4
2-(3,4-Dimethoxyphenyl)ethyl cyclopentanecarboxylate
—— 1,1'-((2-hydroxy-3-methoxy-5-methylbenzyl)azanediyl)bis(propan-2-ol) 1198601-76-1 C15H25NO4
1,1'-((2-hydroxy-3-methoxy-5-methylbenzyl)azanediyl)bis(propan-2-ol)
—— 1050601-03-0 C18H21ClN4O
—— (E)-3-((1-adamantylimino)methyl)benzene-1,2-diol 1339943-34-8 C17H21NO2
(E)-3-((1-adamantylimino)methyl)benzene-1,2-diol
—— 5,11,17,23-tetrakis(1,1-dimethylethyl)-27,28-bis[N-(methanesulfonyl)carbamoylmethoxy]calix[4]arene-25,26-monothiacrown-3 1075184-73-4 C54H72N2O10S3
5,11,17,23-tetrakis(1,1-dimethylethyl)-27,28-bis[N-(methanesulfonyl)carbamoylmethoxy]calix[4]arene-25,26-monothiacrown-3
—— 2-(4-hydroxy-3,5-dimethoxy-benzoyl)-isoxazolidine 30076-10-9 C12H15NO5
2-(4-hydroxy-3,5-dimethoxy-benzoyl)-isoxazolidine
—— 2-iodo-6-methoxy-4-methoxymethyl-phenol 109961-94-6 C9H11IO3
2-iodo-6-methoxy-4-methoxymethyl-phenol
—— 4-Methoxy-2-tert.-pentyl-phenol 26106-41-2 C12H18O2
4-Methoxy-2-tert.-pentyl-phenol
—— 4-methoxy-2-(thiomorpholinomethyl)phenol 1005455-58-2 C12H17NO2S
4-methoxy-2-(thiomorpholinomethyl)phenol
—— (R)-(-)-2-(2-hydroxy-3,3-dimethylbutoxy)-4-iodophenol 1240795-70-3 C12H17IO3
(R)-(-)-2-(2-hydroxy-3,3-dimethylbutoxy)-4-iodophenol
—— (E)-6-Methoxy-2-((2-(dimethylamino)ethylimino)methyl)phenol 1231182-35-6 C12H18N2O2
(E)-6-Methoxy-2-((2-(dimethylamino)ethylimino)methyl)phenol
—— 1-(4-hydroxy-3-methoxy-phenyl)-2-oxo-propane-1-sulfonic acid 99187-17-4 C10H12O6S
1-(4-hydroxy-3-methoxy-phenyl)-2-oxo-propane-1-sulfonic acid
—— 3.4.5.6-Tetramethoxy-salicylaldehyd 65206-43-1 C11H14O6
3.4.5.6-Tetramethoxy-salicylaldehyd
—— 6-(buta-1,3-dienyl)-3-methyl-2-phenylaminophenol 1072098-44-2 C17H17NO
6-(buta-1,3-dienyl)-3-methyl-2-phenylaminophenol
—— 4-(2-phenylhydrazono)-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 1456804-30-0 C20H16N8O4S
4-(2-phenylhydrazono)-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
—— 2,5-Di(cyclohexen-1-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1289448-47-0 C24H33BO3
2,5-Di(cyclohexen-1-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— N,N'-bis(3-hydroxysalicylidene)-1,3-diamino-2-propanol 266689-62-7 C17H18N2O5
N,N'-bis(3-hydroxysalicylidene)-1,3-diamino-2-propanol
—— α-(2-hydroxy-5-methoxyphenyl)-N-tert-butylnitrone 255052-02-9 C12H17NO3
α-(2-hydroxy-5-methoxyphenyl)-N-tert-butylnitrone
—— (E)-1-(5-Bromo-2-hydroxy-3-methyl-phenyl)-3-thiophen-2-yl-propenone 78095-41-7 C14H11BrO2S
(E)-1-(5-Bromo-2-hydroxy-3-methyl-phenyl)-3-thiophen-2-yl-propenone
—— oleacein 1246025-96-6 C17H20O6
oleacein
—— 2-(Chloromethyl)-6-hydroxy-4-methoxybenzaldehyde 2227104-35-8 C9H9ClO3
2-(Chloromethyl)-6-hydroxy-4-methoxybenzaldehyde
—— (3S,3aS,7R,7aS)-7-[2-(5-Hydroxy-2-methyl-phenyl)-ethyl]-3a-methyl-3-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-5-one 89101-40-6 C23H32O4
(3S,3aS,7R,7aS)-7-[2-(5-Hydroxy-2-methyl-phenyl)-ethyl]-3a-methyl-3-(2-methyl-[1,3]dioxolan-2-yl)-octahydro-inden-5-one
—— 3-(3-hydroxy-4-methoxyphenyl)-6-(4-methoxyphenylamino)thieno[2,3-b]pyrrolizin-8-one 1200639-54-8 C23H18N2O4S
3-(3-hydroxy-4-methoxyphenyl)-6-(4-methoxyphenylamino)thieno[2,3-b]pyrrolizin-8-one
—— 5-benzyl-10-ethyl-5-phenyl-5,10-dihydro-dibenzo[<i>b</i>,<i>e</i>][1,4]phospharsininium; picrate 105729-91-7 C6H2N3O7*C27H25AsP
5-benzyl-10-ethyl-5-phenyl-5,10-dihydro-dibenzo[<i>b</i>,<i>e</i>][1,4]phospharsininium; picrate
—— 2-amino-5-(3-iodo-4,5-dimethoxybenzyl)-6-propylpyrimidin-4-ol 1429785-98-7 C16H20IN3O3
2-amino-5-(3-iodo-4,5-dimethoxybenzyl)-6-propylpyrimidin-4-ol
—— 1574408-02-8 C18H14O2
—— 2,2'-[6-(2-octyloxy-ethyl)-[1,3,5]triazine-2,4-diyl]-bis-phenol 38358-79-1 C25H31N3O3
2,2'-[6-(2-octyloxy-ethyl)-[1,3,5]triazine-2,4-diyl]-bis-phenol
—— 5-Hydroxy-N-(3-hydroxy-4-methoxyphenethyl)-6-methoxy-indolin 27240-69-3 C18H21NO4
5-Hydroxy-N-(3-hydroxy-4-methoxyphenethyl)-6-methoxy-indolin
—— disalicylaldehyde phtaloyldihydrazone 119462-95-2 C22H18N4O4
disalicylaldehyde phtaloyldihydrazone
—— N-Hexanoyl-4-hydroxy-3.5-dimethoxy-benzylamin 4973-53-9 C15H23NO4
N-Hexanoyl-4-hydroxy-3.5-dimethoxy-benzylamin
—— 2-bromo-4-(2-bromo-1-methoxy-propyl)-6-methoxy-phenol 91130-85-7 C11H14Br2O3
2-bromo-4-(2-bromo-1-methoxy-propyl)-6-methoxy-phenol
—— 2-(5-hydroxy-5-methylhex-1-en-1-yl)-4-methoxyphenol 1229291-34-2 C14H20O3
2-(5-hydroxy-5-methylhex-1-en-1-yl)-4-methoxyphenol
—— α-(2,4,6-trihydroxyphenyl)-N-tert-butylnitrone 198695-59-9 C11H15NO4
α-(2,4,6-trihydroxyphenyl)-N-tert-butylnitrone
—— 2-Hydroxy-N-(2-hydroxy-ethyl)-benzamidine 79576-69-5 C9H12N2O2
2-Hydroxy-N-(2-hydroxy-ethyl)-benzamidine
—— [(3-hydroxyphenyl)(2-methoxy(D3))methylene]-5-methoxyadamantane 552848-11-0 C19H23ClO3
[(3-hydroxyphenyl)(2-methoxy(D3))methylene]-5-methoxyadamantane
—— 2-(5-amino-[1,3,4]oxadiazol-2-yl)-4,6-dibromo-phenol 75821-13-5 C8H5Br2N3O2
2-(5-amino-[1,3,4]oxadiazol-2-yl)-4,6-dibromo-phenol
—— S-pentafluorophenyl 3-(4-hydroxy-3-methoxyphenyl)propanethioate 1179525-28-0 C16H11F5O3S
S-pentafluorophenyl 3-(4-hydroxy-3-methoxyphenyl)propanethioate
—— 2-(2-methoxy-2-propenyl)-N1,N4-di[(E)-phenylmethylidene]-benzene-1,4-diamine 438187-37-2 C24H22N2O
2-(2-methoxy-2-propenyl)-N1,N4-di[(E)-phenylmethylidene]-benzene-1,4-diamine
—— bis(4-hydroxyphenyl)tellurium(IV) dichloride 78823-98-0 C12H10Cl2O2Te
bis(4-hydroxyphenyl)tellurium(IV) dichloride