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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
—— 904237-22-5 C14H12N2O4
—— benzyl 2-(2-hydroxy-3-methoxyphenyl)acetate 628331-49-7 C16H16O4
benzyl 2-(2-hydroxy-3-methoxyphenyl)acetate
—— vanillidene-p-dimethylaminoaniline 118307-31-6 C16H18N2O2
vanillidene-p-dimethylaminoaniline
—— 4-(4-Hydroxy-3,5-dimethoxy-benzylidene)-2,6-dimethoxy-cyclohexa-2,5-dienone 15395-48-9 C17H18O6
4-(4-Hydroxy-3,5-dimethoxy-benzylidene)-2,6-dimethoxy-cyclohexa-2,5-dienone
—— 4-Hydroxy-2-thio-pyrimidin-5-carboxaldehyd-<(2,4-dinitro-phenyl)-semicarbazon> 91394-50-2 C12H9N7O6S
4-Hydroxy-2-thio-pyrimidin-5-carboxaldehyd-<(2,4-dinitro-phenyl)-semicarbazon>
—— 5-(4-hydroxy-phenoxy)-valeric acid methyl ester 100257-95-2 C12H16O4
5-(4-hydroxy-phenoxy)-valeric acid methyl ester
—— 1201683-02-4 C17H25NO2S2
—— 17179-09-8 C9H10N4O2
—— 6-(Diaminomethylidene)-5-fluorocyclohexa-2,4-dien-1-one 868271-19-6 C7H7FN2O
6-(Diaminomethylidene)-5-fluorocyclohexa-2,4-dien-1-one
—— 3-Hydroxy-2-methyl-4-[2-(1,3-thiazol-2-yl)hydrazinylidene]cyclohexa-2,5-dien-1-one 59652-72-1 C10H9N3O2S
3-Hydroxy-2-methyl-4-[2-(1,3-thiazol-2-yl)hydrazinylidene]cyclohexa-2,5-dien-1-one
—— 4-[2-(4-Hydroxy-phenyl)-ethyl]-3-oxo-heptanoic acid methyl ester 203117-18-4 C16H22O4
4-[2-(4-Hydroxy-phenyl)-ethyl]-3-oxo-heptanoic acid methyl ester
—— 6,6'-dibromo-4,4'-diiodo-2,2'-azo-di-phenol 858013-71-5 C12H6Br2I2N2O2
6,6'-dibromo-4,4'-diiodo-2,2'-azo-di-phenol
—— 3-((4,5-difluoro-2-hydroxyphenyl)amino)-4-(methylamino)cyclobut-3-ene-1,2-dione 945027-50-9 C11H8F2N2O3
3-((4,5-difluoro-2-hydroxyphenyl)amino)-4-(methylamino)cyclobut-3-ene-1,2-dione
—— Sawaranin 117480-09-8 C14H16O7
Sawaranin
—— 3-methyl-2-nitro-4,6-bis(pyrrolidin-1'-ylmethyl)phenol 127396-65-0 C17H25N3O3
3-methyl-2-nitro-4,6-bis(pyrrolidin-1'-ylmethyl)phenol
—— 3-(2-Hydroxy-phenyl)-1-phenyl-Δ<sup>2</sup>-pyrazolin 2535-86-6 C15H14N2O
3-(2-Hydroxy-phenyl)-1-phenyl-Δ<sup>2</sup>-pyrazolin
—— 2-hydroxy-5-nitrobenzyl iodide 116432-32-7 C7H6INO3
2-hydroxy-5-nitrobenzyl iodide
—— [(3-hydroxy-4-nitro-phenyl)-(phenylamino)-methyl]-phosphonic acid diphenyl ester 813449-08-0 C25H21N2O6P
[(3-hydroxy-4-nitro-phenyl)-(phenylamino)-methyl]-phosphonic acid diphenyl ester
—— [S4Calix(Bu-t)(OH)2O2]Mo(PMe3)3H2 1039625-72-3 C49H75MoO4P3S4
[S4Calix(Bu-t)(OH)2O2]Mo(PMe3)3H2
—— 3-(3-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one 1320275-66-8 C16H19NO5
3-(3-hydroxyphenyl)-4-(2-morpholinoethoxy)furan-2(5H)-one
—— 2-(dimorpholinomethyl)-4-(trifluoromethoxy)phenol 1611470-73-5 C16H21F3N2O4
2-(dimorpholinomethyl)-4-(trifluoromethoxy)phenol
—— 2,2',2''-(((nitrilotris(propane-3,1-diyl))tris(azaneylylidene))tris(methaneylylidene))tris(4-bromophenol) 1256270-95-7 C30H33Br3N4O3
2,2',2''-(((nitrilotris(propane-3,1-diyl))tris(azaneylylidene))tris(methaneylylidene))tris(4-bromophenol)
—— 6-{4-[3-(4-{(2S)-2-hydroxy-3-[(methylethyl)amino]propoxy}-3-bromophenoxy)propoxy]-3-chlorophenyl}-2,4,5-trihydropyridazin-3-one 705290-54-6 C19H18BrClN2O4
6-{4-[3-(4-{(2S)-2-hydroxy-3-[(methylethyl)amino]propoxy}-3-bromophenoxy)propoxy]-3-chlorophenyl}-2,4,5-trihydropyridazin-3-one
—— 2-chloro-4-(2-chloroethyl)-5-fluorophenol 698983-78-7 C8H7Cl2FO
2-chloro-4-(2-chloroethyl)-5-fluorophenol
—— 84651-72-9 C4H8O*C6HCl4O2*C10H8N2*Cl*Ni
—— 4-[(3-fluorobenzyl)oxy]-3-methoxyphenol 758706-55-7 C14H13FO3
4-[(3-fluorobenzyl)oxy]-3-methoxyphenol
—— N-[N-(3-(trimethoxysilyl)propyl)ethylenediamine]-5-methylsalicylaldimine 1293408-56-6 C16H28N2O4Si
N-[N-(3-(trimethoxysilyl)propyl)ethylenediamine]-5-methylsalicylaldimine
—— 1,7-Bis(2-hydroxy-4-methylphenyl)heptan 10400-47-2 C21H28O2
1,7-Bis(2-hydroxy-4-methylphenyl)heptan
—— α-(2-hydroxy-5-nitrophenyl)-N-tert-butylnitrone 255052-03-0 C11H14N2O4
α-(2-hydroxy-5-nitrophenyl)-N-tert-butylnitrone
—— {[(1-hydroxy-2-methylpropane-2-yl)imino]methyl}-4-methoxyphenol 1394039-45-2 C12H17NO3
{[(1-hydroxy-2-methylpropane-2-yl)imino]methyl}-4-methoxyphenol
—— 2-(2'-bromo-3'-iodopropyl)phenol 119729-79-2 C9H10BrIO
2-(2'-bromo-3'-iodopropyl)phenol
—— 2-(2-bromo-5-hydroxyphenyl)-2-isopropyl-3-methylbutanenitrile 1380541-15-0 C14H18BrNO
2-(2-bromo-5-hydroxyphenyl)-2-isopropyl-3-methylbutanenitrile
—— tert-butyl (2-((5S,6S)-5-((tert-butyldimethylsilyl)oxy)-6-(2-hydroxy-5-vinylphenoxy)cyclohex-1-en-1-yl)ethyl)(methyl)carbamate 1622096-25-6 C28H45NO5Si
tert-butyl (2-((5S,6S)-5-((tert-butyldimethylsilyl)oxy)-6-(2-hydroxy-5-vinylphenoxy)cyclohex-1-en-1-yl)ethyl)(methyl)carbamate
—— Salicylaldehyd-caprylhydrazon 101354-21-6 C15H22N2O2
Salicylaldehyd-caprylhydrazon
—— N-{4-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-thiazol-2-yl}-acetamide 92494-85-4 C14H14N4O4S
N-{4-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-thiazol-2-yl}-acetamide
—— 2-Hydroxybenzaldehyd-4-(mesitylthiosemicarbazon) 20129-96-8 C17H19N3OS
2-Hydroxybenzaldehyd-4-(mesitylthiosemicarbazon)
—— 4-hexadecyl-2-methoxyphenol 1083004-18-5 C23H40O2
4-hexadecyl-2-methoxyphenol
—— ammonium salicylidensulfamate 22102-27-8 C7H7NO4S*H3N
ammonium salicylidensulfamate
—— 2-[[(5,6-Diphenyl-1,2,4-triazin-3-yl)hydrazinylidene]methyl]-4-nitrophenol 5477-58-7 C22H16N6O3
2-[[(5,6-Diphenyl-1,2,4-triazin-3-yl)hydrazinylidene]methyl]-4-nitrophenol
—— 3,4-bis(pentadecyloxy)phenol 1277180-69-4 C36H66O3
3,4-bis(pentadecyloxy)phenol
—— 2-(3-bromo-4-(triisopropylsilyloxy)phenyl)ethanol 1331740-66-9 C17H29BrO2Si
2-(3-bromo-4-(triisopropylsilyloxy)phenyl)ethanol
—— [OC-6-1',2'-(R*,S*)]-dichlorobis[2-(2-(benzylthio-1-methylamino)ethyl)phenol-N,S]nickel(II) 193075-88-6 C32H38Cl2N2NiO2S2
[OC-6-1',2'-(R*,S*)]-dichlorobis[2-(2-(benzylthio-1-methylamino)ethyl)phenol-N,S]nickel(II)
—— 1-isopropoxy-7-methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-6-ol 942933-33-7 C17H20N4O3
1-isopropoxy-7-methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-6-ol
—— 1-[(3-hydroxy-4-methoxyphenylcarbamoyl)methyl]-3-methyl-3H-imidazol-1-ium chloride 245041-59-2 C13H16N3O3*Cl
1-[(3-hydroxy-4-methoxyphenylcarbamoyl)methyl]-3-methyl-3H-imidazol-1-ium chloride
—— 5-methyl-2-(2-pyridylaldimine)phenol 105516-36-7 C13H12N2O
5-methyl-2-(2-pyridylaldimine)phenol
—— (5-furan-2-yl-[1,3,4]oxadiazol-2-ylsulfanyl)-acetic acid (4-hydroxy-3-methoxy-benzylidene)-hydrazide 33621-33-9 C16H14N4O5S
(5-furan-2-yl-[1,3,4]oxadiazol-2-ylsulfanyl)-acetic acid (4-hydroxy-3-methoxy-benzylidene)-hydrazide
—— 2-Methyl-4-(2-methylthiophen-3-yl)phenol 1262002-69-6 C12H12OS
2-Methyl-4-(2-methylthiophen-3-yl)phenol
—— {(S)-4-Hydroxy-1-hydroxymethyl-1-[2-(4-hydroxy-phenyl)-ethyl]-butyl}-carbamic acid tert-butyl ester 692754-99-7 C18H29NO5
{(S)-4-Hydroxy-1-hydroxymethyl-1-[2-(4-hydroxy-phenyl)-ethyl]-butyl}-carbamic acid tert-butyl ester
—— (E)-(1'-(2)H)-coniferyl alcohol 902515-74-6 C10H12O3
(E)-(1'-(2)H)-coniferyl alcohol
—— (S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenol 1104058-34-5 C13H17NO2
(S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenol