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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
—— 4-(2-iodoethyl)-3,5-dimethylphenol 1020666-88-9 C10H13IO
4-(2-iodoethyl)-3,5-dimethylphenol
—— 3-(tert-butyl)-2-hydroxy-5-(2-methoxyethyl)benzaldehyde 1254176-17-4 C14H20O3
3-(tert-butyl)-2-hydroxy-5-(2-methoxyethyl)benzaldehyde
—— 4-(2-amino-ethyl)-3-methyl-pyrocatechol; hydrobromide 98959-87-6 BrH*C9H13NO2
4-(2-amino-ethyl)-3-methyl-pyrocatechol; hydrobromide
—— 4-Bromo-5-(2-hydroxy-ethyl)-2-methoxy-phenol 55323-57-4 C9H11BrO3
4-Bromo-5-(2-hydroxy-ethyl)-2-methoxy-phenol
—— S-<2-<(2-methylpropylthio)methyl>phenyl>methylthiuronium picrate 95676-02-1 C6H3N3O7*C13H20N2S2
S-<2-<(2-methylpropylthio)methyl>phenyl>methylthiuronium picrate
—— (E)-2-(3,4-Dichloro-2,5-dihydroxy-phenyl)-3-propylamino-but-2-enoic acid ethyl ester 34601-72-4 C15H19Cl2NO4
(E)-2-(3,4-Dichloro-2,5-dihydroxy-phenyl)-3-propylamino-but-2-enoic acid ethyl ester
—— 2-Hydroxy-N-phenethyl-benzamidine 854132-93-7 C15H16N2O
2-Hydroxy-N-phenethyl-benzamidine
—— 1356121-00-0 C15H17NO5
—— 1-(3-Hydroxy-benzyl)-cyclopropanecarboxylic acid ethyl ester 1804-27-9 C13H16O3
1-(3-Hydroxy-benzyl)-cyclopropanecarboxylic acid ethyl ester
—— N-(3-methoxy-4-hydroxybenzyl)-1H-pyrrole 1333534-07-8 C12H13NO2
N-(3-methoxy-4-hydroxybenzyl)-1H-pyrrole
—— 2-[N-(2-(pyridyl-2-yl)ethyl)(1-methylimidazol-2-yl)aminomethyl]-4-methyl-6-[N-(2-(imidazol-4-yl)ethyl)aminomethyl]phenol 1006033-46-0 C26H33N7O
2-[N-(2-(pyridyl-2-yl)ethyl)(1-methylimidazol-2-yl)aminomethyl]-4-methyl-6-[N-(2-(imidazol-4-yl)ethyl)aminomethyl]phenol
—— 5-(4-hydroxy-benz-(Z)-ylidene)-2-[(Z)-propylimino]-3-phenyl-thiazolidin-4-one 1029435-59-3 C19H18N2O2S
5-(4-hydroxy-benz-(Z)-ylidene)-2-[(Z)-propylimino]-3-phenyl-thiazolidin-4-one
—— (E)-5-(4-Hydroxy-3-methoxy-phenyl)-2-oxo-pent-3-enoic acid 76969-04-5 C12H12O5
(E)-5-(4-Hydroxy-3-methoxy-phenyl)-2-oxo-pent-3-enoic acid
—— 4-chloro-2-[(2-piperazin-1-ylethylimino)methyl]phenol 1174589-90-2 C14H19ClN2O
4-chloro-2-[(2-piperazin-1-ylethylimino)methyl]phenol
—— tris(hydrogen 4-hydroxy-3-nitrophenylarsonato)chromium(III) 83981-84-4 C18H15As3CrN3O18
tris(hydrogen 4-hydroxy-3-nitrophenylarsonato)chromium(III)
—— 4-methoxy-2,6-bis(thiomorpholinomethyl)phenol 1041661-67-9 C17H26N2O2S2
4-methoxy-2,6-bis(thiomorpholinomethyl)phenol
—— 9-(4-hydroxy-3-nitrophenylcarbamoyl)nonanoic acid 292607-66-0 C16H22N2O6
9-(4-hydroxy-3-nitrophenylcarbamoyl)nonanoic acid
—— Fluconazolium picrate 1257509-25-3 C6H3N3O7*C13H12F2N6O
Fluconazolium picrate
—— 3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid [6-(4-methoxy-phenoxy)-hexyl]-amide; compound with picric acid 117835-40-2 C6H3N3O7*C19H28N4O3
3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid [6-(4-methoxy-phenoxy)-hexyl]-amide; compound with picric acid
—— 2-(4-hydroxy-3-methoxybenzylideneamino)phenol 51821-39-7 C14H13NO3
2-(4-hydroxy-3-methoxybenzylideneamino)phenol
—— 3β,6,6-trimethyl-3α-hydroxy-2β-(2-hydroxy-4-methyl)phenyl-2α,2aβ,3,4,5,5aα,6,7,8,9,9a,10-dodecahydronaphthol<1,8a-c>furan 78310-36-8 C23H34O4
3β,6,6-trimethyl-3α-hydroxy-2β-(2-hydroxy-4-methyl)phenyl-2α,2aβ,3,4,5,5aα,6,7,8,9,9a,10-dodecahydronaphthol<1,8a-c>furan
—— 80027-29-8 3C6H6O2*2C12H24O6
—— 4-(5-chloro-2-hydroxy benzylidene amino)-pyridine 15877-15-3 C12H9ClN2O
4-(5-chloro-2-hydroxy benzylidene amino)-pyridine
—— dibutyl 2-hydroxyphenylphosphonate 129529-24-4 C14H23O4P
dibutyl 2-hydroxyphenylphosphonate
—— N,N'-dibutyl-t-3,c-4-bis(2-hydroxyphenyl)-r-1,t-2-cyclobutanedicarboxamide 84319-80-2 C26H34N2O4
N,N'-dibutyl-t-3,c-4-bis(2-hydroxyphenyl)-r-1,t-2-cyclobutanedicarboxamide
—— 2-(2-fluoro-4-hydroxyphenyl)ethylamine tert-butyl carbamate 1448545-44-5 C13H18FNO3
2-(2-fluoro-4-hydroxyphenyl)ethylamine tert-butyl carbamate
—— 1375479-16-5 C22H34OSi2
—— 5-methyl-3-(2-hydroxy-4-methoxyphenyl)-4-(4-thiazolyl)isoxazole 82587-52-8 C14H12N2O3S
5-methyl-3-(2-hydroxy-4-methoxyphenyl)-4-(4-thiazolyl)isoxazole
—— 4-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-benzene-1,3-diol 851661-41-1 C17H11ClFN7O3
4-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-benzene-1,3-diol
—— N-(β-Hydroxyphenethyl)-5-nitro-salicylamid 41081-52-1 C15H14N2O5
N-(β-Hydroxyphenethyl)-5-nitro-salicylamid
—— 2-(2-Hydroxy-3-chlor-5-nitro-phenyl-hydrazono)-3-methyl-imino-buttersaeureaethylester 5294-33-7 C13H15ClN4O5
2-(2-Hydroxy-3-chlor-5-nitro-phenyl-hydrazono)-3-methyl-imino-buttersaeureaethylester
—— 1-acetyl-1,2,3,6-tetrahydro-4-(4-hydroxy-3,5-dimethylphenyl)pyridine 180891-97-8 C15H19NO2
1-acetyl-1,2,3,6-tetrahydro-4-(4-hydroxy-3,5-dimethylphenyl)pyridine
—— 5,11,17,23,29,35,41,47-octa(diethoxyphosphoryl)-49,50,51,52,53,54,55,56-octahydroxycalix[8]arene 1078121-74-0 C88H120O32P8
5,11,17,23,29,35,41,47-octa(diethoxyphosphoryl)-49,50,51,52,53,54,55,56-octahydroxycalix[8]arene
—— (R)-2-Amino-3-chloro-N-[(R)-(4-hydroxy-phenyl)-(1H-tetrazol-5-yl)-methyl]-propionamide 129867-20-5 C11H13ClN6O2
(R)-2-Amino-3-chloro-N-[(R)-(4-hydroxy-phenyl)-(1H-tetrazol-5-yl)-methyl]-propionamide
—— 4-(1-allyl-3,4-dimethyl-1,2,5,6-tetrahydro-pyridin-2-ylmethyl)-phenol 41338-50-5 C17H23NO
4-(1-allyl-3,4-dimethyl-1,2,5,6-tetrahydro-pyridin-2-ylmethyl)-phenol
—— 6-(4-{N'-[1-(2,4-Dihydroxy-phenyl)-ethylidene]-hydrazino}-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one 360795-16-0 C19H20N4O3
6-(4-{N'-[1-(2,4-Dihydroxy-phenyl)-ethylidene]-hydrazino}-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one
—— 4-[(E)-(3,5-dimethyl-4-nitrophenyl)vinyl]-2,6-diisopropylphenol 1313376-47-4 C22H27NO3
4-[(E)-(3,5-dimethyl-4-nitrophenyl)vinyl]-2,6-diisopropylphenol
—— 5-methylsalicylaldehydepropanesulfonylhydrazone 1043885-75-1 C11H16N2O3S
5-methylsalicylaldehydepropanesulfonylhydrazone
—— 4-(1-cyclohexenyl)-5-methyl-1,3-benzenediol 37802-37-2 C13H16O2
4-(1-cyclohexenyl)-5-methyl-1,3-benzenediol
—— 4-[(hexahydro-2,5-methano-pentalen-3a-ylamino)methyl]benzene-1,3-diol 1443121-74-1 C16H21NO2
4-[(hexahydro-2,5-methano-pentalen-3a-ylamino)methyl]benzene-1,3-diol
—— 356551-65-0 C17H16N2NiO4
—— 4-(hydrazonomethyl)benzene-1,2-diol 114875-18-2 C7H8N2O2
4-(hydrazonomethyl)benzene-1,2-diol
—— 1-(β-piperidinoethyl)-5-benzotriazole picrate 94120-35-1 C6H3N3O7*C15H22N4O
1-(β-piperidinoethyl)-5-benzotriazole picrate
—— 2-amino-4-(3-hydroxyphenyl)-7,8-dihydro-4H,5H-thiopyrano[4,3-b]pyran-3-carbonitrile 1448024-77-8 C15H14N2O2S
2-amino-4-(3-hydroxyphenyl)-7,8-dihydro-4H,5H-thiopyrano[4,3-b]pyran-3-carbonitrile
—— N-(3-chloro-propionyloxy)-2-hydroxy-benzamidine 93335-42-3 C10H11ClN2O3
N-(3-chloro-propionyloxy)-2-hydroxy-benzamidine
—— 2,2'-[(E)-diazene-1,2-diyldicarbonothioyl]diphenol 1255958-18-9 C14H10N2O2S2
2,2'-[(E)-diazene-1,2-diyldicarbonothioyl]diphenol
—— 1-(4-Hydroxy-3-methoxy-phenyl)-1-(1H-indol-3-yl)-propan-2-one 40446-92-2 C18H17NO3
1-(4-Hydroxy-3-methoxy-phenyl)-1-(1H-indol-3-yl)-propan-2-one
—— 3-{[(2-piperazin-1-ylethyl)imino]methyl}phenol 1375058-94-8 C13H19N3O
3-{[(2-piperazin-1-ylethyl)imino]methyl}phenol
—— 3-Methoxy-2-methoxymethoxy-phenol 122450-19-5 C9H12O4
3-Methoxy-2-methoxymethoxy-phenol
—— 10-(2,4-dihydroxy-phenyl)-decanoic acid methyl ester 855213-70-6 C17H26O4
10-(2,4-dihydroxy-phenyl)-decanoic acid methyl ester