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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-(3',4',5'-Trimethoxyphenyl)-4-hydroxy-6-aminopyrimidin 4234-83-7 C13H15N3O4
2-(3',4',5'-Trimethoxyphenyl)-4-hydroxy-6-aminopyrimidin
—— 5-(3-fluoro-4-hydroxyphenyl)-3-(2-fluorobenzyl)pyrimidin-4(3H)-one 960298-19-5 C17H12F2N2O2
5-(3-fluoro-4-hydroxyphenyl)-3-(2-fluorobenzyl)pyrimidin-4(3H)-one
—— 6-(4-hydroxy-phenyl)-3,4,5,6,7,8-hexahydro-2<i>H</i>-naphthalen-1-one 107059-13-2 C16H18O2
6-(4-hydroxy-phenyl)-3,4,5,6,7,8-hexahydro-2<i>H</i>-naphthalen-1-one
—— 4-{[(2-piperazin-1-ylethyl)imino]methyl}phenol 213688-62-1 C13H19N3O
4-{[(2-piperazin-1-ylethyl)imino]methyl}phenol
—— 4-[4-(5-morpholin-4-yl-penta-1,3-diynyl)-phenylazo]-phenol 36622-18-1 C21H19N3O2
4-[4-(5-morpholin-4-yl-penta-1,3-diynyl)-phenylazo]-phenol
—— (2-nitro-4-bromo-5-hydroxybenzoyl)cyclohexylamine 83102-94-7 C13H15BrN2O4
(2-nitro-4-bromo-5-hydroxybenzoyl)cyclohexylamine
—— 2-[(Z)-2-(4-Chloro-phenylamino)-1-nitro-vinyl]-benzene-1,4-diol 134387-67-0 C14H11ClN2O4
2-[(Z)-2-(4-Chloro-phenylamino)-1-nitro-vinyl]-benzene-1,4-diol
—— 4-(2-hydroxy-phenyl)-6-phenyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one 39594-82-6 C16H14N2O2
4-(2-hydroxy-phenyl)-6-phenyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— 4-Hydroxy-3-methoxyphenyl-(2-pyridyl)carbinol 31754-92-4 C13H13NO3
4-Hydroxy-3-methoxyphenyl-(2-pyridyl)carbinol
—— Salicylaldehyd-(carbonyl-<sup>14</sup>C) 22116-84-3 C7H6O2
Salicylaldehyd-(carbonyl-<sup>14</sup>C)
—— methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate 143135-65-3 C10H11NO4
methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate
—— (1R,2S,3R,4S)-3-((E)-(2-hydroxy-3-methylbenzylidene)amino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 1360459-99-9 C18H25NO2
(1R,2S,3R,4S)-3-((E)-(2-hydroxy-3-methylbenzylidene)amino)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
—— 2-(2-(diethylamino)ethyliminomethyl)-6-methoxyphenol 1012369-02-6 C14H22N2O2
2-(2-(diethylamino)ethyliminomethyl)-6-methoxyphenol
—— (-)-thioepicatechin 1239335-31-9 C15H14O5S
(-)-thioepicatechin
—— 3-(2-(2-hydroxybenzyl)-2-methylhydrazineyl)-N,N,N-trimethyl-3-oxopropan-1-aminium chloride 1017319-40-2 C14H24N3O2*Cl
3-(2-(2-hydroxybenzyl)-2-methylhydrazineyl)-N,N,N-trimethyl-3-oxopropan-1-aminium chloride
—— N,N'-bis[(2-hydroxy-5-nitrophenyl)methylideneamino]oxamide 7155-09-1 C16H12N6O8
N,N'-bis[(2-hydroxy-5-nitrophenyl)methylideneamino]oxamide
—— 6-Trimethylsilanyl-phosphinin-3-ol 108803-47-0 C8H13OPSi
6-Trimethylsilanyl-phosphinin-3-ol
—— 4-(((4-chlorophenyl)thio)methyl)-2-methylphenol 54373-42-1 C14H13ClOS
4-(((4-chlorophenyl)thio)methyl)-2-methylphenol
—— 2-Phenyl-3-(2'-hydroxybenzyl)-Δ1-pyrrolin 78744-86-2 C17H17NO
2-Phenyl-3-(2'-hydroxybenzyl)-Δ1-pyrrolin
—— 6-chloro-<i>N</i>'-(4-hydroxy-3-methoxy-benzylidene)-pyrazine-2-carbohydrazonic acid amide 31683-72-4 C13H12ClN5O2
6-chloro-<i>N</i>'-(4-hydroxy-3-methoxy-benzylidene)-pyrazine-2-carbohydrazonic acid amide
—— Salicylaldehyde monobutyl hydrazone 84646-19-5 C11H16N2O
Salicylaldehyde monobutyl hydrazone
—— 2-(2-Hydroxy-5-nitro-phenyl-hydrazono)-3-methyliminobuttersaeureethylester 5294-31-5 C13H16N4O5
2-(2-Hydroxy-5-nitro-phenyl-hydrazono)-3-methyliminobuttersaeureethylester
—— 1-(1-benzyl-1<i>H</i>-benzoimidazol-2-yl)-5-(2-hydroxy-4,6-dinitro-phenyl)-formazan 37562-19-9 C21H16N8O5
1-(1-benzyl-1<i>H</i>-benzoimidazol-2-yl)-5-(2-hydroxy-4,6-dinitro-phenyl)-formazan
—— Isovanillin-(carbonyl-<sup>14</sup>C) 22116-51-4 C8H8O3
Isovanillin-(carbonyl-<sup>14</sup>C)
—— 2-(1-cyclopentan-1-ylmethyl)-6-methoxyphenol 148173-60-8 C13H18O2
2-(1-cyclopentan-1-ylmethyl)-6-methoxyphenol
—— 71594-51-9 C10H12O4S
—— methoxy(4-hydroxyphenylseleno)methane 126714-66-7 C8H10O2Se
methoxy(4-hydroxyphenylseleno)methane
—— 11,23-di-tert-butyl-5,17-octano-25,26,27,28-tetrahydroxycalix<4>arene 115914-56-2 C44H54O4
11,23-di-tert-butyl-5,17-octano-25,26,27,28-tetrahydroxycalix<4>arene
—— 2-[(1R,6S)-6-[tert-butyl(dimethyl)silyl]oxycyclohex-2-en-1-yl]-5-methylphenol 214629-61-5 C19H30O2Si
2-[(1R,6S)-6-[tert-butyl(dimethyl)silyl]oxycyclohex-2-en-1-yl]-5-methylphenol
—— <i>N</i>,<i>N</i>'-diphenyl-formamidine; picrate 105014-61-7 C6H3N3O7*C13H12N2
<i>N</i>,<i>N</i>'-diphenyl-formamidine; picrate
—— dibutyl [(2-hydroxy-5-nitrophenyl)(6-methoxybenzo[d]thiazol-2-ylamino)methyl]phosphonate 1333496-62-0 C23H30N3O7PS
dibutyl [(2-hydroxy-5-nitrophenyl)(6-methoxybenzo[d]thiazol-2-ylamino)methyl]phosphonate
—— 2-(2-hydroxy-benzylidene)-3,5-dioxo-4-phenyl-isoxazolidinium betaine 38896-44-5 C16H11NO4
2-(2-hydroxy-benzylidene)-3,5-dioxo-4-phenyl-isoxazolidinium betaine
—— 4-(2-(2-hydroxybenzyl)-2-methylhydrazineyl)-N,N,N-trimethyl-4-oxobutan-1-aminium chloride 1017319-41-3 C15H26N3O2*Cl
4-(2-(2-hydroxybenzyl)-2-methylhydrazineyl)-N,N,N-trimethyl-4-oxobutan-1-aminium chloride
—— 4-[(1S)-1-Aminoethyl]-2-nitrophenol 1241682-06-3 C8H10N2O3
4-[(1S)-1-Aminoethyl]-2-nitrophenol
—— (3-Chloro-4-hydroxy-phenyl)-dimethyl-sulfonium 107146-98-5 C8H10ClOS
(3-Chloro-4-hydroxy-phenyl)-dimethyl-sulfonium
—— 4-chloro-2-(diethoxymethylideneamino)phenol 87054-09-9 C11H14ClNO3
4-chloro-2-(diethoxymethylideneamino)phenol
—— 5-allyl-2-hydroxy-3-methoxybenzyl chloride 210229-45-1 C11H13ClO2
5-allyl-2-hydroxy-3-methoxybenzyl chloride
—— 4-(2-amino-1-hydroxyethyl)-2,6-dibromophenol 80573-77-9 C8H9Br2NO2
4-(2-amino-1-hydroxyethyl)-2,6-dibromophenol
—— 2-(3-methoxy-4-hydroxybenzylidine)hydrazinyl-4-phenylthiazole 21938-34-1 C17H15N3O2S
2-(3-methoxy-4-hydroxybenzylidine)hydrazinyl-4-phenylthiazole
—— 2,6-bis(N-(2-amino-1,2-dicyanoetheneimino))-4-methylphenol 1356342-89-6 C17H12N8O
2,6-bis(N-(2-amino-1,2-dicyanoetheneimino))-4-methylphenol
—— (S,E)-4-bromo-2-((1-phenylethylimino)methyl)phenol 1314501-12-6 C15H14BrNO
(S,E)-4-bromo-2-((1-phenylethylimino)methyl)phenol
—— [3-butyl-5-[1-(4-hydroxy-3,5-dimethyl-phenylamino)-meth-(E,Z)-ylidene]-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester 851646-70-3 C21H25N3O4S
[3-butyl-5-[1-(4-hydroxy-3,5-dimethyl-phenylamino)-meth-(E,Z)-ylidene]-4-oxo-thiazolidin-2(E,Z)-ylidene]-cyanoacetic acid ethyl ester
—— 1-Tert-butyl-3-[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]thiourea 218457-53-5 C12H15Br2N3OS
1-Tert-butyl-3-[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]thiourea
—— 104676-56-4 C13H18O5S2Zn
—— 5-bromo-2-(5-methylfuran-2-ylmethyl)phenol 1224199-11-4 C12H11BrO2
5-bromo-2-(5-methylfuran-2-ylmethyl)phenol
—— benzene-1,3-diol;1,1,3,3-tetramethylurea 87448-51-9 C5H12N2O*C6H6O2
benzene-1,3-diol;1,1,3,3-tetramethylurea
—— 4,5-Dichloro-2-hexyl-phenol 52016-74-7 C12H16Cl2O
4,5-Dichloro-2-hexyl-phenol
—— N,N-Bis-(4-chloro-7-methylsalicyliden)-ethylendiamin 28448-93-3 C18H18Cl2N2O2
N,N-Bis-(4-chloro-7-methylsalicyliden)-ethylendiamin
—— 1-Ethyl-2-[(Z)-2-(2-hydroxy-phenyl)-vinyl]-5,6-dihydro-4H-3-thia-1-azonia-benzo[e]azulene; iodide 21503-61-7 C22H22NOS*I
1-Ethyl-2-[(Z)-2-(2-hydroxy-phenyl)-vinyl]-5,6-dihydro-4H-3-thia-1-azonia-benzo[e]azulene; iodide
—— 3-hydroxy-2-(2,4,6-trimethoxybenzylthio)benzaldehyde 901126-79-2 C17H18O5S
3-hydroxy-2-(2,4,6-trimethoxybenzylthio)benzaldehyde