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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-(2-Methyl-2-hydroxy-propyl)-5-methyl-phenol 19956-96-8 C11H16O2
2-(2-Methyl-2-hydroxy-propyl)-5-methyl-phenol
—— 5-(2-hydroxyphenyl)-3-methylisoxazole-4-carboxylic acid 92397-25-6 C11H9NO4
5-(2-hydroxyphenyl)-3-methylisoxazole-4-carboxylic acid
—— Sulfuric acid mono-[2-(3-amino-4-hydroxy-5-nitro-benzenesulfonyl)-ethyl] ester 4726-21-0 C8H10N2O9S2
Sulfuric acid mono-[2-(3-amino-4-hydroxy-5-nitro-benzenesulfonyl)-ethyl] ester
—— 2-Hydroxy-O-methylthiobenzhydroximsaeuremethylester 57598-93-3 C9H11NO2S
2-Hydroxy-O-methylthiobenzhydroximsaeuremethylester
—— 134951-58-9 C12H12N4O2S2
—— (5Z)-2-[(8aR)-octahydropyrrolo[1,2-a]piperazin-2-yl]-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one 1181082-63-2 C17H18FN3O2S
(5Z)-2-[(8aR)-octahydropyrrolo[1,2-a]piperazin-2-yl]-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one
—— N,N-dimethyl-2,5-difluoro-4-hydroxy-3-methoxybenzylamine 138491-16-4 C10H13F2NO2
N,N-dimethyl-2,5-difluoro-4-hydroxy-3-methoxybenzylamine
—— 2,4-Bis-(3'-methoxy-4'-hydroxybenzalamino)-6-hydroxypyrimidine 137206-11-2 C20H18N4O5
2,4-Bis-(3'-methoxy-4'-hydroxybenzalamino)-6-hydroxypyrimidine
—— 2,5-dihydroxy-3-(4-hydroxybenzyl)-6-methylpyrazine 1,4-dioxide 82202-60-6 C12H12N2O5
2,5-dihydroxy-3-(4-hydroxybenzyl)-6-methylpyrazine 1,4-dioxide
—— 4-(2,5-dichlorothiophen-3-yl)benzene-1,2-diol 1067911-57-2 C10H6Cl2O2S
4-(2,5-dichlorothiophen-3-yl)benzene-1,2-diol
—— 2-[3-(4-hydroxy-phenyl)-1-oxo-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-thiophene-3-carbonitrile 1104633-76-2 C19H15NO2S
2-[3-(4-hydroxy-phenyl)-1-oxo-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-thiophene-3-carbonitrile
—— 1-Benzyloxy-4-(2-cyclopentylmethoxy-ethyl)-benzene 108007-98-3 C21H26O2
1-Benzyloxy-4-(2-cyclopentylmethoxy-ethyl)-benzene
—— 36213-17-9 C23H18HgN2O3S
—— N-(3-formylphenyl)-2-(4-hydroxy-2-methoxyphenyl)acetamide 883985-72-6 C16H15NO4
N-(3-formylphenyl)-2-(4-hydroxy-2-methoxyphenyl)acetamide
—— N-Isopropyl-4-O-methyl-noradrenalin 3413-49-8 C12H19NO3
N-Isopropyl-4-O-methyl-noradrenalin
—— 3-((Ξ)-4-hydroxy-benzylidene)-5-methyl-3<i>H</i>-furan-2-one 3269-96-3 C12H10O3
3-((Ξ)-4-hydroxy-benzylidene)-5-methyl-3<i>H</i>-furan-2-one
—— 2-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-5-methoxy-phenol 851661-42-2 C18H13ClFN7O3
2-{[6-(3-chloro-4-fluoro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-5-methoxy-phenol
—— 5-({2-[4-(4-bromophenyl)-1,3-thiazol-2-yl]hydrazinylidene}-methyl)-2-methoxyphenol 464211-21-0 C17H14BrN3O2S
5-({2-[4-(4-bromophenyl)-1,3-thiazol-2-yl]hydrazinylidene}-methyl)-2-methoxyphenol
—— 5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime 173305-02-7 C11H10ClN3O3
5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime
—— 2,6-dibromo-4-(3-(2-bromobenzyloxy)-1,2,4-triazin-6-yl)phenol 1191246-32-8 C16H10Br3N3O2
2,6-dibromo-4-(3-(2-bromobenzyloxy)-1,2,4-triazin-6-yl)phenol
—— N',3,4,5-tetrahydroxybenzene-1-carboximidamide hydrochloride 95933-75-8 C7H9ClN2O4
N',3,4,5-tetrahydroxybenzene-1-carboximidamide hydrochloride
—— 2-(Benzo[1,3,2]dioxarsol-2-ylsulfanyl)-phenol 66073-84-5 C12H9AsO3S
2-(Benzo[1,3,2]dioxarsol-2-ylsulfanyl)-phenol
—— 4-tert-Butyl-2-nitro-6-hydroxy-anilin 70637-66-0 C10H14N2O3
4-tert-Butyl-2-nitro-6-hydroxy-anilin
—— Diethyl-dithiocarbamic acid 3,5-dibromo-4-hydroxy-benzyl ester 30742-33-7 C12H15Br2NOS2
Diethyl-dithiocarbamic acid 3,5-dibromo-4-hydroxy-benzyl ester
—— N-cyclopentyl-3-(2,4-dihydroxybenzyl)-4-hydroxybutanamide 1515405-84-1 C16H23NO4
N-cyclopentyl-3-(2,4-dihydroxybenzyl)-4-hydroxybutanamide
—— 2-[1-(tert-Butyl-dimethyl-silanyloxy)-hex-5-enyl]-6-methoxy-phenol 371195-75-4 C19H32O3Si
2-[1-(tert-Butyl-dimethyl-silanyloxy)-hex-5-enyl]-6-methoxy-phenol
—— 4-(4-methyl-6-phenyl-3,3a-dihydropyrazolo[3,4-c][1,2]oxazol-3-yl)phenol 76794-86-0 C17H15N3O2
4-(4-methyl-6-phenyl-3,3a-dihydropyrazolo[3,4-c][1,2]oxazol-3-yl)phenol
—— 937276-04-5 C21H21N2OP
—— 5-(4-Hydroxy-3-methoxybenzyl)2,4-dimethylpyrazin 73570-34-0 C14H16N2O2
5-(4-Hydroxy-3-methoxybenzyl)2,4-dimethylpyrazin
—— 1082287-33-9 C16H11N5O5
—— 2-hydroxy-3-((hydroxyimino)methyl)-5-methoxybenzaldehyde 1440207-67-9 C9H9NO4
2-hydroxy-3-((hydroxyimino)methyl)-5-methoxybenzaldehyde
—— 1-(2-chloro-4,5-dihydroxybenzyl)-1,2,3,4,4a,5-hexahydroisoquinolin-6(8aH)-one 886836-14-2 C16H18ClNO3
1-(2-chloro-4,5-dihydroxybenzyl)-1,2,3,4,4a,5-hexahydroisoquinolin-6(8aH)-one
—— 4,6-diiodo-2,3,5-trimethyl-phenol 7282-06-6 C9H10I2O
4,6-diiodo-2,3,5-trimethyl-phenol
—— 153245-61-5 C13H18N4O5Zn*H2O
—— N-(4-Chloro-phenyl)-4-hydroxy-3,5-dimethyl-thiobenzamide 120951-52-2 C15H14ClNOS
N-(4-Chloro-phenyl)-4-hydroxy-3,5-dimethyl-thiobenzamide
—— o-Hydroxyphenylglyoxalsaeure syn thiosemicarbazon 34659-67-1 C9H9N3O3S
o-Hydroxyphenylglyoxalsaeure syn thiosemicarbazon
—— 4-Chloro-6-nitro-3-pentadecylphenol 32749-44-3 C21H34ClNO3
4-Chloro-6-nitro-3-pentadecylphenol
—— 2,6-bis(125I)(iodanyl)-4-nitrophenol 74067-35-9 C6H3I2NO3
2,6-bis(125I)(iodanyl)-4-nitrophenol
—— 1299470-13-5 C22H32OS
—— 2,4-Dinitro-phenol; compound with trimethyl-phosphane 28051-18-5 C3H9P*C6H4N2O5
2,4-Dinitro-phenol; compound with trimethyl-phosphane
—— 2-Methoxy-6-octyl-phenol 148173-51-7 C15H24O2
2-Methoxy-6-octyl-phenol
—— N-[2-(4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethyl]-6-[2-(4-phenylmethoxy)-phenylethoxy]hexanamide 143440-88-4 C30H34N2O5S
N-[2-(4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethyl]-6-[2-(4-phenylmethoxy)-phenylethoxy]hexanamide
—— 2-chloro-1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 1082036-80-3 C17H15ClN2O2
2-chloro-1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
—— 2854-73-1 C19H13N3O4S
—— Tert-butyl [5-hydroxy-2-iodo-4-(3-methylbut-2-enyl)phenyl] carbonate 1155310-10-3 C16H21IO4
Tert-butyl [5-hydroxy-2-iodo-4-(3-methylbut-2-enyl)phenyl] carbonate
—— 4-methyl-2-(pyrimidin-2-yl)phenol 1246562-31-1 C11H10N2O
4-methyl-2-(pyrimidin-2-yl)phenol
—— 6-<2,6,6-trimethylcyclohex-1-enyl)methyl>-2-methylbenzene-1,4-diol 131265-53-7 C17H24O2
6-<2,6,6-trimethylcyclohex-1-enyl)methyl>-2-methylbenzene-1,4-diol
—— 887111-83-3 C11H18O2Sn
—— 4-Sulfonamido-benzoesaeure-5-nitrosalicyliden-hydrazon 41377-71-3 C14H12N4O6S
4-Sulfonamido-benzoesaeure-5-nitrosalicyliden-hydrazon
—— 4,4'-Dihydroxy-α,β-bis-(trimethylsilyl)-stilben 40426-11-7 C20H28O2Si2
4,4'-Dihydroxy-α,β-bis-(trimethylsilyl)-stilben