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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
—— 2,6-dibromo-3-fluoro-4-nitro-phenol 2369-46-2 C6H2Br2FNO3
2,6-dibromo-3-fluoro-4-nitro-phenol
—— 3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-5-(3-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one 62329-58-2 C18H10ClN3O3S2
3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-5-(3-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one
—— 54827-98-4 C10H13Cl2NO2
—— 4-hydroxy-α-propylphenylacetic acid 88255-30-5 C11H14O3
4-hydroxy-α-propylphenylacetic acid
—— methyl (Z)-2-(2-hydroxyphenyl)-2-methoxyimino-acetate 143135-66-4 C10H11NO4
methyl (Z)-2-(2-hydroxyphenyl)-2-methoxyimino-acetate
—— (E,E)-(1-cyano-4-(3,4-dihydroxyphenyl)-buta-1,3-dienyl)phosphonic acid diethyl ester 866030-99-1 C15H18NO5P
(E,E)-(1-cyano-4-(3,4-dihydroxyphenyl)-buta-1,3-dienyl)phosphonic acid diethyl ester
—— 2-(chloromethyl)-4,6-diiodo-phenol 959965-59-4 C7H5ClI2O
2-(chloromethyl)-4,6-diiodo-phenol
—— 5-Butyl-pyridine-2-carboxylic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide 31004-97-4 C18H21N3O3
5-Butyl-pyridine-2-carboxylic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide
—— 2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(3,5-dimethoxyphenyl)acetamide) 1333164-75-2 C36H39N3O12
2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(3,5-dimethoxyphenyl)acetamide)
—— 4-{2-[2-(2-Hydroxy-pentyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 91815-19-9 C17H26O5
4-{2-[2-(2-Hydroxy-pentyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol
—— 2-bromo-N-(2-hydroxy-3-hydroxymethyl-5-methoxyphenyl)-3-methylbutyramide 944357-03-3 C13H18BrNO4
2-bromo-N-(2-hydroxy-3-hydroxymethyl-5-methoxyphenyl)-3-methylbutyramide
—— 5-(2,4-dihydroxy-styryl)-furan-2-carboxylic acid methyl ester 20925-07-9 C14H12O5
5-(2,4-dihydroxy-styryl)-furan-2-carboxylic acid methyl ester
—— 1574514-58-1 C18H21I2N3O4
—— 3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-5-propyl-1,5-dihydro-pyrrol-2-one 1024608-00-1 C19H23N3O3
3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-5-propyl-1,5-dihydro-pyrrol-2-one
—— 2,4-diethoxy-3-methoxy-6-methylphenol 136165-90-7 C12H18O4
2,4-diethoxy-3-methoxy-6-methylphenol
—— 4-[(4-hydroxyphenyl)-(3-methyl-1-phenyl-5-sulfanylidene-4H-pyrazol-4-yl)methyl]-3-methyl-1,4-dihydropyrazol-5-one 96128-66-4 C21H20N4O2S
4-[(4-hydroxyphenyl)-(3-methyl-1-phenyl-5-sulfanylidene-4H-pyrazol-4-yl)methyl]-3-methyl-1,4-dihydropyrazol-5-one
—— 1-methoxy-2-hydroxy-3-isopropyl-5-allylbenzene 83569-74-8 C13H18O2
1-methoxy-2-hydroxy-3-isopropyl-5-allylbenzene
—— (C4H9)3SnONCHC6H4OH-2 20141-74-6 C19H33NO2Sn
(C4H9)3SnONCHC6H4OH-2
—— 3-chloro-6-hydroxy-2,4-dimethyl-benzaldehyde-oxime 81322-68-1 C9H10ClNO2
3-chloro-6-hydroxy-2,4-dimethyl-benzaldehyde-oxime
—— 3-[1-hydroxy-2-(propan-2-ylamino)ethyl]-6-methoxy-2-propylphenol 79822-75-6 C15H25NO3
3-[1-hydroxy-2-(propan-2-ylamino)ethyl]-6-methoxy-2-propylphenol
—— 2-[1-(2,2-Dimethyl-propylsulfanyl)-2,2-dimethyl-propyl]-4-methoxy-phenol 54624-39-4 C17H28O2S
2-[1-(2,2-Dimethyl-propylsulfanyl)-2,2-dimethyl-propyl]-4-methoxy-phenol
—— [VO(Hshed)(cat)] 145319-14-8 C17H19N2O5V
[VO(Hshed)(cat)]
—— 4-(Bis-phenylsulfanyl-methyl)-5-bromo-2-methoxy-phenol 108791-58-8 C20H17BrO2S2
4-(Bis-phenylsulfanyl-methyl)-5-bromo-2-methoxy-phenol
—— 4-<1-Acetylamino-ethyl>-2.6-dimethyl-phenol 14712-58-4 C12H17NO2
4-<1-Acetylamino-ethyl>-2.6-dimethyl-phenol
—— 2,4-Dibrom-5-hydroxy-3-methoxytoluol 34132-38-2 C8H8Br2O2
2,4-Dibrom-5-hydroxy-3-methoxytoluol
—— 3-acetyl-5-(4-hydroxy-benzyl)-pyrrolidine-2,4-dione 729-32-8 C13H13NO4
3-acetyl-5-(4-hydroxy-benzyl)-pyrrolidine-2,4-dione
—— 2-[(E)-3-(2-Methoxy-ethoxy)-1-methyl-allyl]-phenol 18061-84-2 C13H18O3
2-[(E)-3-(2-Methoxy-ethoxy)-1-methyl-allyl]-phenol
—— 3-(2-Bromo-4-hydroxy-3,5-dimethoxy-phenyl)-propionic acid methyl ester 35714-36-4 C12H15BrO5
3-(2-Bromo-4-hydroxy-3,5-dimethoxy-phenyl)-propionic acid methyl ester
—— 4-chloro-2-iodo-3,5-dimethyl-phenol 38730-45-9 C8H8ClIO
4-chloro-2-iodo-3,5-dimethyl-phenol
—— 2,5-dihydroxy-3-nitro-benzoic acid hydrazide 98279-93-7 C7H7N3O5
2,5-dihydroxy-3-nitro-benzoic acid hydrazide
—— [6-(2-Hydroxy-phenyl)-hexyl]-carbamic acid tert-butyl ester 141920-32-3 C17H27NO3
[6-(2-Hydroxy-phenyl)-hexyl]-carbamic acid tert-butyl ester
—— 4-Bromo-2-{[(Z)-3-ethylsulfanyl-propylimino]-methyl}-phenol 91802-06-1 C12H16BrNOS
4-Bromo-2-{[(Z)-3-ethylsulfanyl-propylimino]-methyl}-phenol
—— 4-(2,2-dibromovinyl)-2-methylphenol 1159343-18-6 C9H8Br2O
4-(2,2-dibromovinyl)-2-methylphenol
—— 2-Methoxy-4-[5-(2-methyl-[1,8]naphthyridin-3-yl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol 119496-56-9 C19H18N4O2
2-Methoxy-4-[5-(2-methyl-[1,8]naphthyridin-3-yl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol
—— 2-Tert-butyl-5-hydroxy-1,2-benzoxazol-3-one 697801-56-2 C11H13NO3
2-Tert-butyl-5-hydroxy-1,2-benzoxazol-3-one
—— 2,6-di(α-hydroxyhexafluoroisopropyl)phenol 122134-90-1 C12H6F12O3
2,6-di(α-hydroxyhexafluoroisopropyl)phenol
—— p-tert-butyl-calix[4]arene phosphite 135839-87-1 C44H53O4P
p-tert-butyl-calix[4]arene phosphite
—— N,N'-bis<1-(2-hydroxy-3-methylphenyl)ethylidene>ethylenediamine 82539-32-0 C20H24N2O2
N,N'-bis<1-(2-hydroxy-3-methylphenyl)ethylidene>ethylenediamine
—— 51084-49-2 C10H9Br2N3O3S
—— 90900-18-8 C22H28N2O4
—— 2-(2-bromo-1,1,2,2-tetrafluoroethyl)benzene-1,4-diol 1005776-37-3 C8H5BrF4O2
2-(2-bromo-1,1,2,2-tetrafluoroethyl)benzene-1,4-diol
—— tert-butyl N-[2-[3,5-dibromo-4-[3-[[3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]propoxy]phenyl]ethyl]carbamate 206991-15-3 C26H31Br4N3O7
tert-butyl N-[2-[3,5-dibromo-4-[3-[[3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]propoxy]phenyl]ethyl]carbamate
—— 3-Hydroxy-1,2-dimethoxy-4-ethoxalyl-benzol 91498-01-0 C12H14O6
3-Hydroxy-1,2-dimethoxy-4-ethoxalyl-benzol
—— 2'-hydroxy-4-nitroacetophenone thiosemicarbazone 882816-71-9 C9H10N4O3S
2'-hydroxy-4-nitroacetophenone thiosemicarbazone
—— 1-(3-Chlor-4-hydroxyphenyl)-3-cyclopropylpropan-3-on 66422-33-1 C12H13ClO2
1-(3-Chlor-4-hydroxyphenyl)-3-cyclopropylpropan-3-on
—— 1-[2,4-Dihydroxy-3-(hydroxy-pyridin-4-yl-methyl)-phenyl]-ethanone oxime 35590-33-1 C14H14N2O4
1-[2,4-Dihydroxy-3-(hydroxy-pyridin-4-yl-methyl)-phenyl]-ethanone oxime
—— 2-methoxy-5-(((2,4,6-trimethoxyphenethyl)sulfonyl)methyl)phenol 1584657-21-5 C19H24O7S
2-methoxy-5-(((2,4,6-trimethoxyphenethyl)sulfonyl)methyl)phenol
—— 4-bromo-2-(3,5-dimethyl-7,8-dihydro-6H-[1,2]oxazolo[4,5-b]azepin-7-yl)phenol 80630-23-5 C15H15BrN2O2
4-bromo-2-(3,5-dimethyl-7,8-dihydro-6H-[1,2]oxazolo[4,5-b]azepin-7-yl)phenol
—— 21503-63-9 C23H24NO2S*I
—— Acetic acid 3,6-diacetoxy-2-(2-hydroxy-ethyl)-4-methoxy-phenyl ester 154821-87-1 C15H18O8
Acetic acid 3,6-diacetoxy-2-(2-hydroxy-ethyl)-4-methoxy-phenyl ester