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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-(4-phenylbutyl)phenyl 124211-67-2 C17H20O
2-(4-phenylbutyl)phenyl
—— 4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol 1237512-73-0 C11H17NO3
4-(2-aminopropoxy)-3-(hydroxymethyl)-5-methylphenol
—— (S)-2-(2-hydroxy-4-methoxyphenylamino)-thiazoline-5,5-dimethyl-4-carboxylic acid 1334386-02-5 C13H16N2O4S
(S)-2-(2-hydroxy-4-methoxyphenylamino)-thiazoline-5,5-dimethyl-4-carboxylic acid
—— 4-[[6-[2-[2-[6-[(3,4-Dihydroxyphenyl)methylamino]hexylamino]ethyldisulfanyl]ethylamino]hexylamino]methyl]benzene-1,2-diol 75575-17-6 C30H50N4O4S2
4-[[6-[2-[2-[6-[(3,4-Dihydroxyphenyl)methylamino]hexylamino]ethyldisulfanyl]ethylamino]hexylamino]methyl]benzene-1,2-diol
—— 2-(thiophen-3-ylmethyl)phenol 109106-67-4 C11H10OS
2-(thiophen-3-ylmethyl)phenol
—— 2-Cyclopent-3-enylmethyl-3,4-difluoro-phenol 248275-64-1 C12H12F2O
2-Cyclopent-3-enylmethyl-3,4-difluoro-phenol
—— 4-hydroxy-3-methoxy-α-nitro-<i>cis</i>-cinnamonitrile 58046-27-8 C10H8N2O4
4-hydroxy-3-methoxy-α-nitro-<i>cis</i>-cinnamonitrile
—— methyl 3-cyano-3-(4-hydroxy-2-methoxyphenyl)propanoate 1356600-84-4 C12H13NO4
methyl 3-cyano-3-(4-hydroxy-2-methoxyphenyl)propanoate
—— (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 1216936-80-9 C19H17NO4
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— Diethyl 2-[(4-hydroxy-3-methoxyanilino)methylidene]propanedioate 104007-05-8 C15H19NO6
Diethyl 2-[(4-hydroxy-3-methoxyanilino)methylidene]propanedioate
—— (E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 1216936-78-5 C19H17NO4
(E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— 2,5-di(1-propynyl)-1,4-benzenediol 1331730-62-1 C12H10O2
2,5-di(1-propynyl)-1,4-benzenediol
—— (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 1216936-79-6 C20H19NO5
(E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
—— 1-(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)-1-(4-hydroxyphenyl)methanol 143258-65-5 C17H19N3O2
1-(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)-1-(4-hydroxyphenyl)methanol
—— N,N′,N′′-tris(3,4-dihydroxybenzylidene)adamantane-1,3,5-tripropaneamine 1448150-60-4 C40H49N3O6
N,N′,N′′-tris(3,4-dihydroxybenzylidene)adamantane-1,3,5-tripropaneamine
—— 4-(6-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)benzene-1,2-diol 1616377-38-8 C15H14O4S
4-(6-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)benzene-1,2-diol
—— 3,7-diaza-5,5-dimethyl-2,8-bis(2'-hydroxyphenyl)nonane 187960-80-1 C21H30N2O2
3,7-diaza-5,5-dimethyl-2,8-bis(2'-hydroxyphenyl)nonane
—— 2-(2-hydroxyphenyl)-2-methylcyclobutanone 121004-50-0 C11H12O2
2-(2-hydroxyphenyl)-2-methylcyclobutanone
—— acetamino-5-methoxyresorcinol 460048-04-8 C9H11NO4
acetamino-5-methoxyresorcinol
—— (3Z)-6-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one 135521-95-8 C17H13ClO3S
(3Z)-6-chloro-3-[(3-hydroxy-4-methoxyphenyl)methylidene]thiochromen-4-one
—— 2-chloro-5-iodo-3-methoxyphenol 1272528-73-0 C7H6ClIO2
2-chloro-5-iodo-3-methoxyphenol
—— 3-(2,3-dihydroxyphenyl)propylphosphonic acid 1410218-39-1 C9H13O5P
3-(2,3-dihydroxyphenyl)propylphosphonic acid
—— 5-chloro-2-methoxy-4-methyl-phenol 33963-23-4 C8H9ClO2
5-chloro-2-methoxy-4-methyl-phenol
—— 2-hydroxy-5-iodo-4-methoxybenzaldehyde 237056-75-6 C8H7IO3
2-hydroxy-5-iodo-4-methoxybenzaldehyde
—— 2-bromo-4-n-hexyl-3-hydroxy-N-pivaloylaniline 168335-64-6 C17H26BrNO2
2-bromo-4-n-hexyl-3-hydroxy-N-pivaloylaniline
—— 2-Hydroxy-4-methoxy-5-(3-methylbut-2-enyl)benzaldehyde 37761-55-0 C13H16O3
2-Hydroxy-4-methoxy-5-(3-methylbut-2-enyl)benzaldehyde
—— 2-[(1<i>H</i>-[1,2,4]triazol-3-ylimino)-methyl]-phenol 24829-12-7 C9H8N4O
2-[(1<i>H</i>-[1,2,4]triazol-3-ylimino)-methyl]-phenol
—— (9Z,12Z)-1-(2-(4-hydroxyphenyl)ethoxy)-octadeca-9,12-diene 1118587-28-2 C26H42O2
(9Z,12Z)-1-(2-(4-hydroxyphenyl)ethoxy)-octadeca-9,12-diene
—— 2-Hexadecylmercapto-hydrochinon 6485-18-3 C22H38O2S
2-Hexadecylmercapto-hydrochinon
—— 3,5-diethyl-4-[6-(4-hydroxyphenoxy)hexyl]isoxazole 98263-51-5 C19H27NO3
3,5-diethyl-4-[6-(4-hydroxyphenoxy)hexyl]isoxazole
—— 4-dimethylaminoguaiacol 4956-55-2 C9H13NO2
4-dimethylaminoguaiacol
—— 1-(3,4-dihydroxybenzyl)imidazoline hydrochloride 96826-02-7 C10H12N2O2*ClH
1-(3,4-dihydroxybenzyl)imidazoline hydrochloride
—— 2-(tert-butyl)-5-nitrophenol 442847-11-2 C10H13NO3
2-(tert-butyl)-5-nitrophenol
—— 6-(2-bromoallyl)-2,3-dimethoxy-5-hydroxy-4-methyl-benzonitrile 114252-20-9 C13H14BrNO3
6-(2-bromoallyl)-2,3-dimethoxy-5-hydroxy-4-methyl-benzonitrile
—— 6-(2-chloroallyl)-2,3-dimethoxy-5-hydroxy-4-methylbenzonitrile 114252-21-0 C13H14ClNO3
6-(2-chloroallyl)-2,3-dimethoxy-5-hydroxy-4-methylbenzonitrile
—— 6-allyl-2,3-dimethoxy-5-hydroxy-4-methylbenzonitrile 114252-22-1 C13H15NO3
6-allyl-2,3-dimethoxy-5-hydroxy-4-methylbenzonitrile
—— 2,2,2-trifluoro-N-(2-hydroxyphenethyl)acetamide 108773-31-5 C10H10F3NO2
2,2,2-trifluoro-N-(2-hydroxyphenethyl)acetamide
—— 2,4,6-Trichlor-3-aminophenol 35869-49-9 C6H4Cl3NO
2,4,6-Trichlor-3-aminophenol
—— 4-bromo-2-[(3 diethylaminopropylimino)methyl]phenol 1261599-02-3 C14H21BrN2O
4-bromo-2-[(3 diethylaminopropylimino)methyl]phenol
—— 2-hydroxy-3-methylbenzaldehyde oxime 51673-93-9 C8H9NO2
2-hydroxy-3-methylbenzaldehyde oxime
—— Riccardiphenol B 179749-28-1 C21H28O2
Riccardiphenol B
—— 2-bromo-3-hydroxy-4-methoxy-benzonitrile 850856-57-4 C8H6BrNO2
2-bromo-3-hydroxy-4-methoxy-benzonitrile
—— 1-(3',4'-dihydroxyphenyl)-5-phenylpent-4-en-1-yne 131271-51-7 C17H14O2
1-(3',4'-dihydroxyphenyl)-5-phenylpent-4-en-1-yne
—— N,N,N'-trimethyl-N'-(2,4-dihydroxyphenylmethyl)ethanediamine 934218-90-3 C12H20N2O2
N,N,N'-trimethyl-N'-(2,4-dihydroxyphenylmethyl)ethanediamine
—— 2-amino-4,6-dibromo-3,5-dimethyl-phenol 854672-42-7 C8H9Br2NO
2-amino-4,6-dibromo-3,5-dimethyl-phenol
—— 2-chloro-3-fluoro-4-nitrophenol 1632444-57-5 C6H3ClFNO3
2-chloro-3-fluoro-4-nitrophenol
—— 3-(5-chloro-2-hydroxyphenyl)cyclobutanone 294669-31-1 C10H9ClO2
3-(5-chloro-2-hydroxyphenyl)cyclobutanone
—— 4,6-bis[5-(4-methylphenyl)-1,2-oxazol-3-yl]benzene-1,3-diol 137369-36-9 C26H20N2O4
4,6-bis[5-(4-methylphenyl)-1,2-oxazol-3-yl]benzene-1,3-diol
—— 4-Brom-2-methoxy-5-(2-nitro-vinyl)-phenol 7396-73-8 C9H8BrNO4
4-Brom-2-methoxy-5-(2-nitro-vinyl)-phenol
—— tert-butyl 2-(4-hydroxy-2-methoxyphenyl)acetate 948571-52-6 C13H18O4
tert-butyl 2-(4-hydroxy-2-methoxyphenyl)acetate