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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-bromo-3-(3-bromo-4-hydroxy-phenyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104633-57-9 C14H12Br2O2
2-bromo-3-(3-bromo-4-hydroxy-phenyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— 94919-32-1 C10H7N3O2S*H3N*Ni
—— 1-hydroxypiperazine dipicrate 69395-50-2 C4H10N2O*2C6H3N3O7
1-hydroxypiperazine dipicrate
—— 5,5,10-triethyl-5,10-dihydro-phosphanthrenium; dipicrate 103937-05-9 C6H2N3O7*C6H3N3O7*C18H23P2
5,5,10-triethyl-5,10-dihydro-phosphanthrenium; dipicrate
—— 3-[(2-hydroxy-3-methoxybenzylidene)amino]propane-1,2-diol 1423139-75-6 C11H15NO4
3-[(2-hydroxy-3-methoxybenzylidene)amino]propane-1,2-diol
—— 36213-18-0 C25H22HgN2O3S
—— 3-hydroxymethyl-5-methyl-salicylaldoxime 1447502-32-0 C9H11NO3
3-hydroxymethyl-5-methyl-salicylaldoxime
—— 1-(2,5-Dihydroxy-phenyl)-3-methyl-tetrahydro-thiopyranium; chloride 92278-04-1 C12H17O2S*Cl
1-(2,5-Dihydroxy-phenyl)-3-methyl-tetrahydro-thiopyranium; chloride
—— 2-(2,2-dichlorovinyl)-6-methylphenol 1159343-11-9 C9H8Cl2O
2-(2,2-dichlorovinyl)-6-methylphenol
—— 2,5-bis{[(2-hydroxyethyl)(methyl)amino]methyl}benzene-1,4-diol 109066-57-1 C14H24N2O4
2,5-bis{[(2-hydroxyethyl)(methyl)amino]methyl}benzene-1,4-diol
—— N'-(4-hydroxybenzylidene)piperidine-1-carbothiohydrazide 1198400-25-7 C13H17N3OS
N'-(4-hydroxybenzylidene)piperidine-1-carbothiohydrazide
—— (5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-54-8 C15H16ClN3O2S
(5Z)-5-[(5-chloro-2-hydroxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— N-2-pyridylmethylidene-2-hydroxy-5-chlorophenylamine 20211-18-1 C12H9ClN2O
N-2-pyridylmethylidene-2-hydroxy-5-chlorophenylamine
—— (E)-N'-(3-bromo-4-hydroxy-5-nitrobenzylidene)-2-(4-chlorophenylamino)acetohydrazide 1068708-45-1 C15H12BrClN4O4
(E)-N'-(3-bromo-4-hydroxy-5-nitrobenzylidene)-2-(4-chlorophenylamino)acetohydrazide
—— 4-bromo-2-(but-3-enyl)phenol 1186642-17-0 C10H11BrO
4-bromo-2-(but-3-enyl)phenol
—— Methyl-bis-<2-hydroxy-5-methoxy-benzyl>-amin 98107-09-6 C17H21NO4
Methyl-bis-<2-hydroxy-5-methoxy-benzyl>-amin
—— 6-<i>tert</i>-butyl-2-chloro-3-methyl-4-nitro-phenol 72373-76-3 C11H14ClNO3
6-<i>tert</i>-butyl-2-chloro-3-methyl-4-nitro-phenol
—— 1,2-Benzenediol, 4-[2-[(5-amino-1-methylpentyl)amino]-1-hydroxyethyl]-,dihydrochloride 88719-37-3 C14H24N2O3*2ClH
1,2-Benzenediol, 4-[2-[(5-amino-1-methylpentyl)amino]-1-hydroxyethyl]-,dihydrochloride
—— Salicylaldehyde monopropyl hydrazone 82046-36-4 C10H14N2O
Salicylaldehyde monopropyl hydrazone
—— 2-[(Z)-2',3'-bis(methoxycarbonyl)allyl]-6-methylphenol 1160556-03-5 C14H16O5
2-[(Z)-2',3'-bis(methoxycarbonyl)allyl]-6-methylphenol
—— 51084-55-0 C12H15N3O4S
—— o-(6-Bromhexyl)-phenol 51795-90-5 C12H17BrO
o-(6-Bromhexyl)-phenol
—— 6-(3-hydroxy-4-methoxyanilino)-1H-pyrimidine-2,4-dione 1448808-15-8 C11H11N3O4
6-(3-hydroxy-4-methoxyanilino)-1H-pyrimidine-2,4-dione
—— 10,25-di-tert-butyl-14,21-dimethyl-3,6,14,21-tetraazatricyclo[21.3.1.18,12]octacosa-1(27),2,6,8,10,12(28),23,25-octaene-27,28-diol 676226-17-8 C34H52N4O2
10,25-di-tert-butyl-14,21-dimethyl-3,6,14,21-tetraazatricyclo[21.3.1.18,12]octacosa-1(27),2,6,8,10,12(28),23,25-octaene-27,28-diol
—— 4-hydroxy-5-[N-(2-hydroxyphenyl)ethanimidoyl]-2H-1,3-thiazine-2,6(3H)-dione 869584-57-6 C12H10N2O4S
4-hydroxy-5-[N-(2-hydroxyphenyl)ethanimidoyl]-2H-1,3-thiazine-2,6(3H)-dione
—— 1-(5-Nitrosalicyliden)-4-(4-chlorphenyl)-thiosemicarbazon 41377-34-8 C14H11ClN4O3S
1-(5-Nitrosalicyliden)-4-(4-chlorphenyl)-thiosemicarbazon
—— 2-(2-Iodo-5-methoxy-phenyl)-ethanol 72594-56-0 C9H11IO2
2-(2-Iodo-5-methoxy-phenyl)-ethanol
—— 2-(1-Isopropylsulfanyl-1-methyl-ethyl)-4-methoxy-phenol 54624-49-6 C13H20O2S
2-(1-Isopropylsulfanyl-1-methyl-ethyl)-4-methoxy-phenol
—— 2-[[[4-(Azepan-1-yl)-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-4-methoxyphenol 6415-24-3 C23H26N8O4
2-[[[4-(Azepan-1-yl)-6-(4-nitroanilino)-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-4-methoxyphenol
—— 3-amino-4-[(3,5-dimethoxy,4-hydroxyphenyl)methylene]-1H-pyrazol-5(4H)-one 1267391-82-1 C12H13N3O4
3-amino-4-[(3,5-dimethoxy,4-hydroxyphenyl)methylene]-1H-pyrazol-5(4H)-one
—— (1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethyl-α-(2,3,5,6-tetramethoxyphenyl)naphthalene-1-methanol acetate 619300-86-6 C27H42O6
(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethyl-α-(2,3,5,6-tetramethoxyphenyl)naphthalene-1-methanol acetate
—— 2,2-Dimethyl-propionic acid 5-[(E)-hydroxyimino]-5,6,7,8,9,9a-hexahydro-benzo[3,4]cyclobuta[1,2]cyclohepten-4b-yl ester 126475-48-7 C18H23NO3
2,2-Dimethyl-propionic acid 5-[(E)-hydroxyimino]-5,6,7,8,9,9a-hexahydro-benzo[3,4]cyclobuta[1,2]cyclohepten-4b-yl ester
—— 4-chloro-2-(1-imidazol-1-ylprop-1-enyl)phenol 112361-30-5 C12H11ClN2O
4-chloro-2-(1-imidazol-1-ylprop-1-enyl)phenol
—— 4-(2-(3-methoxyphenylhydrazono))-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 1456804-37-7 C21H18N8O5S
4-(2-(3-methoxyphenylhydrazono))-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
—— diethyl (propane-1,3-diylbis(azanediyl))bis((2-hydroxyphenyl)methylene)bis(hydrogen phosphonate) 101920-08-5 C25H40N2O8P2
diethyl (propane-1,3-diylbis(azanediyl))bis((2-hydroxyphenyl)methylene)bis(hydrogen phosphonate)
—— Cu(vanillinate)2(ethanolamine)2 1146616-60-5 C20H28CuN2O10
Cu(vanillinate)2(ethanolamine)2
—— 2-[2,2-Dichloro-1-(2-hydroxy-5-methylphenyl)ethenyl]-4-methylphenol 70605-54-8 C16H14Cl2O2
2-[2,2-Dichloro-1-(2-hydroxy-5-methylphenyl)ethenyl]-4-methylphenol
—— 1-(3',4',5'-trihydroxyphenyl)-2-isopropylaminoethanol, hydrochloride 54790-04-4 C11H17NO4*ClH
1-(3',4',5'-trihydroxyphenyl)-2-isopropylaminoethanol, hydrochloride
—— N<sup>1</sup>-4-methylbenzylidene-N<sup>2</sup>-[3-(4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 1380074-92-9 C24H21N3O3S
N<sup>1</sup>-4-methylbenzylidene-N<sup>2</sup>-[3-(4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine
—— (E)-4-(3-((2-amino-4,5,6,7-tetrahydrobenzo[d] thiazol-6-yl)(propyl)amino)prop-1-en-1-yl)-2-methoxyphenol 1612146-72-1 C20H27N3O2S
(E)-4-(3-((2-amino-4,5,6,7-tetrahydrobenzo[d] thiazol-6-yl)(propyl)amino)prop-1-en-1-yl)-2-methoxyphenol
—— 2-[1-(3-fluoro-4-hydroxy-5-methoxy-phenyl)-meth-(Z)-ylidene]-6-(pyridin-4-yl)-imidazo[2,1-b]thiazol-3-one 1567849-19-7 C18H12FN3O3S
2-[1-(3-fluoro-4-hydroxy-5-methoxy-phenyl)-meth-(Z)-ylidene]-6-(pyridin-4-yl)-imidazo[2,1-b]thiazol-3-one
—— 4-Methoxy-2-tricosyl-phenol 144464-95-9 C30H54O2
4-Methoxy-2-tricosyl-phenol
—— 2-[4-[2-(3-bromobenzyloxy)ethyl]phenyl]ethanol 851437-10-0 C17H19BrO2
2-[4-[2-(3-bromobenzyloxy)ethyl]phenyl]ethanol
—— 1,5-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-pentanol-(3) 94962-57-9 C21H28O3
1,5-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-pentanol-(3)
—— N,N,N',N'-tetrakis(3-salicylideneaminopropyl)ethylenediamine 101205-67-8 C42H52N6O4
N,N,N',N'-tetrakis(3-salicylideneaminopropyl)ethylenediamine
—— 4-[(4-hydroxybenzylidene)amino]benzene-1,3-diol 1449522-04-6 C13H11NO3
4-[(4-hydroxybenzylidene)amino]benzene-1,3-diol
—— 1322575-04-1 C15H13BrN2O
—— 4-methyl-2,6-dipentylphenol 116375-00-9 C17H28O
4-methyl-2,6-dipentylphenol
—— (5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-[(2S)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-68-7 C17H20FN3O3S
(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-[(2S)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— 2,6-bis(salicylidenaminomethyl)-4-methylphenol 96689-02-0 C23H22N2O3
2,6-bis(salicylidenaminomethyl)-4-methylphenol