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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
—— 5-Methyl-2-(2-methylene-cyclohexylmethyl)-benzene-1,3-diol 39596-28-6 C15H20O2
5-Methyl-2-(2-methylene-cyclohexylmethyl)-benzene-1,3-diol
—— 1,2-phenylenebis(methylene) bis(2-(2-hydroxybenzylidene)-1-methylhydrazine-1-carbodithioate) 135446-68-3 C26H26N4O2S4
1,2-phenylenebis(methylene) bis(2-(2-hydroxybenzylidene)-1-methylhydrazine-1-carbodithioate)
—— 4-[(S)-5-(2-Chloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-6-[(R)-5-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-benzene-1,3-diol 134248-23-0 C24H20Cl2N4O2
4-[(S)-5-(2-Chloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-6-[(R)-5-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-benzene-1,3-diol
—— 1-<Bis-(2-methoxycarbonyl-aethylmercapto)-methyl>-4-hydroxy-3-methoxy-benzol 976-31-8 C16H22O6S2
1-<Bis-(2-methoxycarbonyl-aethylmercapto)-methyl>-4-hydroxy-3-methoxy-benzol
—— pentacyclo<19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>1519</sup>>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, 5,11,17,23-tetrabromo-2,8,14,20-tetrapentyl- 386213-66-7 C48H60Br4O8
pentacyclo<19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>1519</sup>>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol, 5,11,17,23-tetrabromo-2,8,14,20-tetrapentyl-
—— {Zn(II)-(gallacetophenone phenylhydrazone)2} 125920-93-6 C28H26N4O6Zn
{Zn(II)-(gallacetophenone phenylhydrazone)2}
—— 3-[4-(hydroxymethyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]phenol 1191258-99-7 C9H8N2O4
3-[4-(hydroxymethyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]phenol
—— 910639-81-5 C22H27ClO2S
—— 5,11-dibromo-17-fluorotetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3(21),4,6,9,11,13(20),15(19),16-nonaene-19,20,21-triol 83142-68-1 C21H15Br2FO3
5,11-dibromo-17-fluorotetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3(21),4,6,9,11,13(20),15(19),16-nonaene-19,20,21-triol
—— diethyl 2,4-dimethoxy-6-hydroxyphenylphosphonate 80615-42-5 C12H19O6P
diethyl 2,4-dimethoxy-6-hydroxyphenylphosphonate
—— 5-[1-(4-Bromo-phenyl)-meth-(Z)-ylidene]-2-(4-hydroxy-3-methoxy-phenyl)-3-(2-mercapto-phenyl)-thiazolidin-4-one oxime 128921-83-5 C23H19BrN2O3S2
5-[1-(4-Bromo-phenyl)-meth-(Z)-ylidene]-2-(4-hydroxy-3-methoxy-phenyl)-3-(2-mercapto-phenyl)-thiazolidin-4-one oxime
—— 5-(3-Hydroxy-propyl)-3-nitro-brenzcatechin 90610-79-0 C9H11NO5
5-(3-Hydroxy-propyl)-3-nitro-brenzcatechin
—— 5-{(4<i>S</i>)-5<i>c</i>-[(<i>R</i>)-acetoxy-((<i>R</i>)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4<i>r</i>-yl}-oxazole-4-carboxylic acid ethyl ester 66107-72-0 C19H27NO9
5-{(4<i>S</i>)-5<i>c</i>-[(<i>R</i>)-acetoxy-((<i>R</i>)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4<i>r</i>-yl}-oxazole-4-carboxylic acid ethyl ester
—— o-Vanillin-(2-hydroxyacetophenon)-azin 97740-16-4 C16H16N2O3
o-Vanillin-(2-hydroxyacetophenon)-azin
—— 6-Hydroxy-5-methoxy-3-propyl-1-allyl-benzol 854733-53-2 C13H18O2
6-Hydroxy-5-methoxy-3-propyl-1-allyl-benzol
—— 3-Chlor-2-hydroxy-4,6,2'-trimethoxy-4'-methoxycarbonyloxy-6'-methyl-benzophenon 95276-67-8 C19H19ClO8
3-Chlor-2-hydroxy-4,6,2'-trimethoxy-4'-methoxycarbonyloxy-6'-methyl-benzophenon
—— 4-[4-[4-Hydroxy-3-(1,2-oxazol-5-yl)phenoxy]butoxy]-2-(1,2-oxazol-5-yl)phenol 865352-33-6 C22H20N2O6
4-[4-[4-Hydroxy-3-(1,2-oxazol-5-yl)phenoxy]butoxy]-2-(1,2-oxazol-5-yl)phenol
—— 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole 88742-91-0 C10H11N3O3S
2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole
—— 2-Hydroxybenzimidoylacetamid-oxim 59899-09-1 C9H11N3O2
2-Hydroxybenzimidoylacetamid-oxim
—— 4-hydroxy-3-methoxy-benzaldehyde 4-benzothiazol-2-yl-thiosemicarbazone 70161-76-1 C16H14N4O2S2
4-hydroxy-3-methoxy-benzaldehyde 4-benzothiazol-2-yl-thiosemicarbazone
—— 1380518-39-7 C15H14N2O2
—— 4-cyclooctyl resorcinol 221617-34-1 C14H20O2
4-cyclooctyl resorcinol
—— (E)-3'-hydroxy-4'-methoxyacetophenone O-2,4-difluorobenzyl oxime 1072708-89-4 C16H15F2NO3
(E)-3'-hydroxy-4'-methoxyacetophenone O-2,4-difluorobenzyl oxime
—— (2,4-Dihydroxy-phenyl)-trimethylsilanyloxy-acetonitrile 83575-56-8 C11H15NO3Si
(2,4-Dihydroxy-phenyl)-trimethylsilanyloxy-acetonitrile
—— (5-Hydroxy-4-methoxy-2-methylphenyl)-essigsaeure 60699-61-8 C10H12O4
(5-Hydroxy-4-methoxy-2-methylphenyl)-essigsaeure
—— 2-((1R)-1-{[(1R)-1-(4-hydroxybutyl)-1-pentyl-3-butenyl]amino}ethyl)phenol 451503-75-6 C21H35NO2
2-((1R)-1-{[(1R)-1-(4-hydroxybutyl)-1-pentyl-3-butenyl]amino}ethyl)phenol
—— 2-(4-(methoxymethoxy)phenyl)ethanol 126716-61-8 C10H14O3
2-(4-(methoxymethoxy)phenyl)ethanol
—— 4-bromo-2-(5-butylamino-[1,3,4]thiadiazol-2-yl)-phenol 35314-04-6 C12H14BrN3OS
4-bromo-2-(5-butylamino-[1,3,4]thiadiazol-2-yl)-phenol
—— 4-(5-Brom-thiazol-2-yl-azo)brenzcatechin 57135-22-5 C9H6BrN3O2S
4-(5-Brom-thiazol-2-yl-azo)brenzcatechin
—— 2-(2,2-dichlorocyclopropyl)-6-methylphenol 499235-46-0 C10H10Cl2O
2-(2,2-dichlorocyclopropyl)-6-methylphenol
—— m-cresol-triethylamine 60264-86-0 C6H15N*C7H8O
m-cresol-triethylamine
—— 3-(2'-hydroxyphenyl)-6-methyl-5-phenyl-1,2,4-triazine 118207-09-3 C16H13N3O
3-(2'-hydroxyphenyl)-6-methyl-5-phenyl-1,2,4-triazine
—— 1-(3-Hydroxyphenyl)-3-methyl-2-pyrazolin-5-one 107430-40-0 C10H10N2O2
1-(3-Hydroxyphenyl)-3-methyl-2-pyrazolin-5-one
—— 4-Nitro-3,3,7-trimethyl-2-(2-hydroxy-3-nitro-5-methoxystyryl)indolenine 129431-64-7 C20H19N3O6
4-Nitro-3,3,7-trimethyl-2-(2-hydroxy-3-nitro-5-methoxystyryl)indolenine
—— 2-cyclopentyl-6,7-dichloroindan-1,5-diol 57509-33-8 C14H16Cl2O2
2-cyclopentyl-6,7-dichloroindan-1,5-diol
—— 1,4,7,10,13,16-hexaoxacyclooctadecane;2-nitrobenzene-1,3-diol 80027-31-2 C6H5NO4*C12H24O6
1,4,7,10,13,16-hexaoxacyclooctadecane;2-nitrobenzene-1,3-diol
—— 2-[2-(3-methyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenol 72398-84-6 C11H10N2O2
2-[2-(3-methyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenol
—— 2-Hydroxy-N-aethyl-benzimid-methylester 4611-39-6 C10H13NO2
2-Hydroxy-N-aethyl-benzimid-methylester
—— 2-(1-Methyl-cyclopentyl)-phenol 68522-51-0 C12H16O
2-(1-Methyl-cyclopentyl)-phenol
—— (R)-tert-butyl (4-(2-(4-aminophenyl)-1,3-dithiolan-2-yl)butyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)carbamate 1346655-31-9 C35H51N3O5S2Si
(R)-tert-butyl (4-(2-(4-aminophenyl)-1,3-dithiolan-2-yl)butyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)carbamate
—— 4-((2-hydroxybenzylidene)amino)-3-thioxo-1,2,4-triazinan-5-one 1254335-87-9 C10H10N4O2S
4-((2-hydroxybenzylidene)amino)-3-thioxo-1,2,4-triazinan-5-one
—— 2-(1-[1,2,4]triazol-4-ylimino-ethyl)-phenol 35554-85-9 C10H10N4O
2-(1-[1,2,4]triazol-4-ylimino-ethyl)-phenol
—— 2,3,5,6-tetrabromo-4-(2,3,4,6-tetrabromo-anilino)-phenol 861076-77-9 C12H3Br8NO
2,3,5,6-tetrabromo-4-(2,3,4,6-tetrabromo-anilino)-phenol
—— 2-(2-Aminoethyliminomethyl)-4-chlorophenol 1379429-43-2 C9H11ClN2O
2-(2-Aminoethyliminomethyl)-4-chlorophenol
—— 2,4-Dideutero-guajacol 7329-54-6 C7H8O2
2,4-Dideutero-guajacol
—— 4-(2,2-Difluoro-1-hydroxy-2-nitro-1-trifluoromethyl-ethyl)-6-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-benzene-1,3-diol 123716-16-5 C12H6F11NO6
4-(2,2-Difluoro-1-hydroxy-2-nitro-1-trifluoromethyl-ethyl)-6-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-benzene-1,3-diol
—— 4-bromo-2-{(E)-[(5-chloro-2-hydroxyphenyl)imino]methyl}-6-methoxyphenol 362620-58-4 C14H11BrClNO3
4-bromo-2-{(E)-[(5-chloro-2-hydroxyphenyl)imino]methyl}-6-methoxyphenol
—— N-benzyl-N-(2-benzyloxy-5-(R)-oxiranylphenyl)methanesulfonamide 960398-27-0 C16H17NO4S
N-benzyl-N-(2-benzyloxy-5-(R)-oxiranylphenyl)methanesulfonamide
—— 4-oxo-4-(4-hydroxy-3-methyl-phenyl)-<i>trans</i>-crotonic acid 103986-32-9 C11H10O4
4-oxo-4-(4-hydroxy-3-methyl-phenyl)-<i>trans</i>-crotonic acid
—— 1-<3-Hydroxy-4-iod-phenyl>-cyclopentan-carbonsaeure-(1) 88565-62-2 C12H13IO3
1-<3-Hydroxy-4-iod-phenyl>-cyclopentan-carbonsaeure-(1)