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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-(5-methyl-4,5-dihydro-oxazol-2-yl)-phenol 98034-08-3 C10H11NO2
4-(5-methyl-4,5-dihydro-oxazol-2-yl)-phenol
—— 2-(2-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-97-1 C15H21N3O2S
2-(2-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 3-methoxy-salicylidene-glycine 51094-54-3 C10H11NO4
3-methoxy-salicylidene-glycine
—— α-(2-Hydroxy-benzyl)-γ-butyrolacton 92016-97-2 C11H12O3
α-(2-Hydroxy-benzyl)-γ-butyrolacton
—— 3-[(2-Hydroxyphenyl)methylidene]-1-methylpyrrolidin-2-one 74255-06-4 C12H13NO2
3-[(2-Hydroxyphenyl)methylidene]-1-methylpyrrolidin-2-one
—— α-(2'-hydroxybenzylidene)-γ-butyrolactone 4736-29-2 C11H10O3
α-(2'-hydroxybenzylidene)-γ-butyrolactone
—— (S)-tert-butyl 4-(3,5-dihydroxy-4-methoxybenzyl)-2,2-dimethyloxazolidine-3-carboxylate 1423720-72-2 C18H27NO6
(S)-tert-butyl 4-(3,5-dihydroxy-4-methoxybenzyl)-2,2-dimethyloxazolidine-3-carboxylate
—— (+/-)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester 475481-86-8 C14H20O4
(+/-)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester
—— 4-nonadecylphenol 105281-81-0 C25H44O
4-nonadecylphenol
—— 1-(2-Hydroxy-3-methoxyphenyl)-12-phenyldodecane 106484-86-0 C25H36O2
1-(2-Hydroxy-3-methoxyphenyl)-12-phenyldodecane
—— anion of resorcinol 20217-24-7 C6H5O2
anion of resorcinol
—— 2-hydroxy-6-methylphenyl dimethylcarbamate 1631050-46-8 C10H13NO3
2-hydroxy-6-methylphenyl dimethylcarbamate
—— 4-[(4S)-4-methylhexoxy]phenol 95880-50-5 C13H20O2
4-[(4S)-4-methylhexoxy]phenol
—— 2-(4-chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one 892871-53-3 C19H13ClN2O3S
2-(4-chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one
—— (E)-2-hydroxy-3,5-dinitrostyryl 4-fluorobenzyl sulfone 334969-25-4 C15H11FN2O7S
(E)-2-hydroxy-3,5-dinitrostyryl 4-fluorobenzyl sulfone
—— Dimethyl 4-(4-hydroxy-3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 105572-51-8 C17H18N2O7
Dimethyl 4-(4-hydroxy-3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
—— 4-[2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-5,5-dimethyl-2-oxofuran-3-carbonitrile 125208-30-2 C16H15NO4
4-[2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-5,5-dimethyl-2-oxofuran-3-carbonitrile
—— methyl 4-hydroxyphenylphosphinate 146406-43-1 C7H9O3P
methyl 4-hydroxyphenylphosphinate
—— 3-hydroxy-6-(3,4-dihydroxybenzylidene)-4-(4-hydroxyphenyl)-pyran-2,5-dione 41744-33-6 C18H12O7
3-hydroxy-6-(3,4-dihydroxybenzylidene)-4-(4-hydroxyphenyl)-pyran-2,5-dione
—— 5-allyl-3-(benzyloxy)benzene-1,2-diol 1146966-11-1 C16H16O3
5-allyl-3-(benzyloxy)benzene-1,2-diol
—— tris(2-hydroxyphenyl)(methyl)silane 1010689-17-4 C19H18O3Si
tris(2-hydroxyphenyl)(methyl)silane
—— (2R,3R)-N-[2-(4-hydroxyphenyl)ethyl]-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanamide;hydrobromide 1307229-21-5 BrH*C17H26N2O3
(2R,3R)-N-[2-(4-hydroxyphenyl)ethyl]-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanamide;hydrobromide
—— 2,4-Dibromo-6-[(4-phenyl-1,3-thiazol-2-yl)iminomethyl]phenol 77203-56-6 C16H10Br2N2OS
2,4-Dibromo-6-[(4-phenyl-1,3-thiazol-2-yl)iminomethyl]phenol
—— 5,5-dimethyl-2-(3-hydroxy-4-methoxyphenyl)-1,3-dioxane 176659-11-3 C13H18O4
5,5-dimethyl-2-(3-hydroxy-4-methoxyphenyl)-1,3-dioxane
—— p-hydroxy-m-methoxybenzylidene-2-amino-4-phenylthiazole 13243-77-1 C17H14N2O2S
p-hydroxy-m-methoxybenzylidene-2-amino-4-phenylthiazole
—— 5-benzyloxy-2-hydroxyacetophenone ethoxycarbonylhydrazone 1384938-80-0 C18H20N2O4
5-benzyloxy-2-hydroxyacetophenone ethoxycarbonylhydrazone
—— 2-(3-hydroxy-2-nitrophenyl)-2,5,5-trimethyl-1,3-dioxane 199985-10-9 C13H17NO5
2-(3-hydroxy-2-nitrophenyl)-2,5,5-trimethyl-1,3-dioxane
—— 4-(5,5-dimethyl-1,3-dioxan-2-yl)phenol 61683-81-6 C12H16O3
4-(5,5-dimethyl-1,3-dioxan-2-yl)phenol
—— 2-methyl-2-<3-(3'-methoxy-2'-hydroxy)phenyl>-pentyloxirane 118090-87-2 C13H18O3
2-methyl-2-<3-(3'-methoxy-2'-hydroxy)phenyl>-pentyloxirane
—— 5-(2-hydroxy-3-methoxyphenyl)-2-pentanone 123973-93-3 C12H16O3
5-(2-hydroxy-3-methoxyphenyl)-2-pentanone
—— 3-methoxy-2-hydroxy-α-methylstyrene 87307-81-1 C10H12O2
3-methoxy-2-hydroxy-α-methylstyrene
—— 2-benzyloxy-3-methoxyphenol 122450-20-8 C14H14O3
2-benzyloxy-3-methoxyphenol
—— 4,4'-(isoxazol-3,5-diyl)diphenol 22439-73-2 C15H11NO3
4,4'-(isoxazol-3,5-diyl)diphenol
—— (E)-3,5-bis(4-hydroxyphenyl )-4-(non-1-en-1-yl)isoxazole  1400414-26-7 C24H27NO3
(E)-3,5-bis(4-hydroxyphenyl )-4-(non-1-en-1-yl)isoxazole 
—— (E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole 1400414-32-5 C21H21NO3
(E)-4-(3,3-dimethyl-but-1-E-en-1-yl)-3,5-bis(4-hydroxyphenyl )isoxazole
—— 2-Methoxy-6-methyl-4-propan-2-yl-phenol 1083004-16-3 C11H16O2
2-Methoxy-6-methyl-4-propan-2-yl-phenol
—— (E)-N-(4-hydroxy-3-methoxy-d3-benzyl)-8-methylnon-6-enamide 1217899-52-9 C18H27NO3
(E)-N-(4-hydroxy-3-methoxy-d3-benzyl)-8-methylnon-6-enamide
—— 4-methoxy-2-[6-hydroxy-E-1-hexenyl]phenol 252233-97-9 C13H18O3
4-methoxy-2-[6-hydroxy-E-1-hexenyl]phenol
—— 3-benzyloxy-2-methoxyphenol 1072844-44-0 C14H14O3
3-benzyloxy-2-methoxyphenol
—— 2-fluoro-6-((methylamino)methyl)-4-nitrophenol 1508296-29-4 C8H9FN2O3
2-fluoro-6-((methylamino)methyl)-4-nitrophenol
—— 2-hydroxy-5-nitrophenylacetic acid methyl ester 155388-58-2 C9H9NO5
2-hydroxy-5-nitrophenylacetic acid methyl ester
—— methyl 2-(3-bromo-2-hydroxyphenyl)acetate 628331-74-8 C9H9BrO3
methyl 2-(3-bromo-2-hydroxyphenyl)acetate
—— 4-methoxy-2-(methoxyethoxy)methoxyphenol 881027-28-7 C11H16O5
4-methoxy-2-(methoxyethoxy)methoxyphenol
—— 4-chloro-2-[(5-methyl-3-isoxazolyl)amino]methylphenol 1153622-49-1 C11H11ClN2O2
4-chloro-2-[(5-methyl-3-isoxazolyl)amino]methylphenol
—— (S)-4-(1-hydroxy-2-nitroethyl)phenol 1268725-97-8 C8H9NO4
(S)-4-(1-hydroxy-2-nitroethyl)phenol
—— tert-butyl 2-(2-hydroxy-3-methoxybenzoyl)acrylate 1351365-26-8 C15H18O5
tert-butyl 2-(2-hydroxy-3-methoxybenzoyl)acrylate
—— {(1-4-η)-5-(2-amino-6-hydroxy-5-methoxy-3,4-dimethylphenyl)cyclohexa-1,3-diene}tricarbonyliron 125937-42-0 C18H19FeNO5
{(1-4-η)-5-(2-amino-6-hydroxy-5-methoxy-3,4-dimethylphenyl)cyclohexa-1,3-diene}tricarbonyliron
—— 5,11,17,23-Tetrakis(3-hydroxypropoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 1274936-97-8 C60H88O16
5,11,17,23-Tetrakis(3-hydroxypropoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— 2-(3-hydroxyphenyl)cyclopropyl cyclopropyl ketone 219521-18-3 C13H14O2
2-(3-hydroxyphenyl)cyclopropyl cyclopropyl ketone
—— 3-(3,4-dihydroxyphenyl)propyl acetate 1390634-11-3 C11H14O4
3-(3,4-dihydroxyphenyl)propyl acetate