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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-diethylphosphoryl-6-methylphenol 129529-18-6 C11H17O2P
2-diethylphosphoryl-6-methylphenol
—— 5-Hydroxy-2-oxo-4,7-dimethyl-1,3-benzoxathiol 7735-66-2 C9H8O3S
5-Hydroxy-2-oxo-4,7-dimethyl-1,3-benzoxathiol
—— [(E)-4-[benzyl-[(3-hydroxy-4-methoxyphenyl)methyl]amino]but-2-enyl] methyl carbonate 1374156-32-7 C21H25NO5
[(E)-4-[benzyl-[(3-hydroxy-4-methoxyphenyl)methyl]amino]but-2-enyl] methyl carbonate
—— 4-bromo-2-{[6-(3-chloro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-6-methoxy-phenol 851661-28-4 C18H13BrClN7O3
4-bromo-2-{[6-(3-chloro-phenylamino)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-6-methoxy-phenol
—— 2,6-dimethyl-4-(1-hydroxycyclobutyl)phenol 1234665-28-1 C12H16O2
2,6-dimethyl-4-(1-hydroxycyclobutyl)phenol
—— N-Hydroxy-2-(4-hydroxy-phenoxy)-acetamide 22446-16-8 C8H9NO4
N-Hydroxy-2-(4-hydroxy-phenoxy)-acetamide
—— 3-[(4-Hydroxy-2,6-dimethyl-phenyl)-methyl-amino]-propionitrile 30198-70-0 C12H16N2O
3-[(4-Hydroxy-2,6-dimethyl-phenyl)-methyl-amino]-propionitrile
—— Acetic acid N'-(2-hydroxy-3-methoxy-benzyl)-hydrazide 25996-40-1 C10H14N2O3
Acetic acid N'-(2-hydroxy-3-methoxy-benzyl)-hydrazide
—— Ethyl 2-(8-fluoro-4-hydroxy-5-methoxynaphthalen-2-yl)-4-methyl-1,3-thiazole-5-carboxylate 1221565-37-2 C18H16FNO4S
Ethyl 2-(8-fluoro-4-hydroxy-5-methoxynaphthalen-2-yl)-4-methyl-1,3-thiazole-5-carboxylate
—— 2-(2-morpholin-4-yl-cyclohexyl)-benzene-1,4-diol 97811-12-6 C16H23NO3
2-(2-morpholin-4-yl-cyclohexyl)-benzene-1,4-diol
—— 2-Methoxy-5-[[4-(3,4,5-trimethoxyanilino)-1,3,5-triazin-2-yl]amino]phenol 333734-77-3 C19H21N5O5
2-Methoxy-5-[[4-(3,4,5-trimethoxyanilino)-1,3,5-triazin-2-yl]amino]phenol
—— 6-Benzo[1,3]dioxol-5-yl-4-(2-hydroxy-4-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 101986-18-9 C23H22O7
6-Benzo[1,3]dioxol-5-yl-4-(2-hydroxy-4-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
—— 890-76-6 C14H15NO3
—— 4-(methylaminomethyl)-3,5-dimethoxyphenol 879896-37-4 C10H15NO3
4-(methylaminomethyl)-3,5-dimethoxyphenol
—— 2-((E)-3-Ethoxy-1-methyl-allyl)-phenol 18062-12-9 C12H16O2
2-((E)-3-Ethoxy-1-methyl-allyl)-phenol
—— 2-{[(Z)-2-Dodecylsulfanyl-ethylimino]-methyl}-phenol 94969-78-5 C21H35NOS
2-{[(Z)-2-Dodecylsulfanyl-ethylimino]-methyl}-phenol
—— 104676-58-6 C13H18HgO5S2
—— 3,4-anhydro-3''-hydroxy-α-ericadione 1425335-10-9 C21H22O5
3,4-anhydro-3''-hydroxy-α-ericadione
—— decanoic acid [5-(4-hydroxy-3,5-dimethoxy-benzylidene)-2-(3-nitrophenyl)- 4-oxo-thiazolidin-3-yl]amide 1290139-29-5 C28H35N3O7S
decanoic acid [5-(4-hydroxy-3,5-dimethoxy-benzylidene)-2-(3-nitrophenyl)- 4-oxo-thiazolidin-3-yl]amide
—— 4-(5-chloro-2-hydroxy-phenyl)-thiosemicarbazide 73305-15-4 C7H8ClN3OS
4-(5-chloro-2-hydroxy-phenyl)-thiosemicarbazide
—— 5-bromo-3-fluoro-2-methoxyphenol 1409956-13-3 C7H6BrFO2
5-bromo-3-fluoro-2-methoxyphenol
—— 5-(5-bromo-2-hydroxybenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione 1372864-85-1 C16H18BrNO3S
5-(5-bromo-2-hydroxybenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione
—— 6-[(5-Bromo-2-hydroxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione 188925-62-4 C17H25BrN4O3
6-[(5-Bromo-2-hydroxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione
—— 2-(((6-bromopyridin-3-yl)methylene)amino)-5-methoxyphenol 960591-48-4 C13H11BrN2O2
2-(((6-bromopyridin-3-yl)methylene)amino)-5-methoxyphenol
—— 2,4,4'-Trihydroxytetraphenylmethan 34916-22-8 C25H20O3
2,4,4'-Trihydroxytetraphenylmethan
—— 4-(3,4-dihydroxyphenethyl)-5-prophyl-2H-1,2,4-triazol-3(4H)-one 1313389-88-6 C13H17N3O3
4-(3,4-dihydroxyphenethyl)-5-prophyl-2H-1,2,4-triazol-3(4H)-one
—— (CH3)2Sn(C6H4-p-OH)2 35937-04-3 C14H16O2Sn
(CH3)2Sn(C6H4-p-OH)2
—— 1,1,3,3-tetrakis(salicylidene-3-iminopropyl)butylenediamine 1028904-08-6 C44H56N6O4
1,1,3,3-tetrakis(salicylidene-3-iminopropyl)butylenediamine
—— 2-[5-(2-hydroxy-phenyl)-1<i>H</i>-[1,2,4]triazol-3-yl]-5-(2-octadecyl-phenyl)-1,2-dihydro-pyrazol-3-one 23585-68-4 C35H49N5O2
2-[5-(2-hydroxy-phenyl)-1<i>H</i>-[1,2,4]triazol-3-yl]-5-(2-octadecyl-phenyl)-1,2-dihydro-pyrazol-3-one
—— 4-(1-Aminomethyl-1-butyl-pentyl)-phenol 16254-64-1 C16H27NO
4-(1-Aminomethyl-1-butyl-pentyl)-phenol
—— 3,4-Bis-(2-hydroxy-phenyl)-furan-2,5-dione 13225-82-6 C16H10O5
3,4-Bis-(2-hydroxy-phenyl)-furan-2,5-dione
—— 2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)-4-nitrophenol 1374575-84-4 C12H15NO4Si
2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)-4-nitrophenol
—— 2-(4-methoxyphenyl)ethyl 2-mercaptoisobutyrate 1117818-55-9 C13H18O3S
2-(4-methoxyphenyl)ethyl 2-mercaptoisobutyrate
—— 2,5-divanillyl-cyclopentanone 51728-79-1 C21H24O5
2,5-divanillyl-cyclopentanone
—— (E)-1-(3,5-Dihydroxy-4-methyl-phenyl)-pent-3-en-2-one 34695-87-9 C12H14O3
(E)-1-(3,5-Dihydroxy-4-methyl-phenyl)-pent-3-en-2-one
—— (5Z)-1-tert-butyl-5-(tert-butylimino)-3-(3-hydroxyphenyl)-1H-pyrrol-2(5H)-one 1370031-63-2 C18H24N2O2
(5Z)-1-tert-butyl-5-(tert-butylimino)-3-(3-hydroxyphenyl)-1H-pyrrol-2(5H)-one
—— 4-(4,5,6,7-Tetrahydro-1H-[1,2]diazepin-3-yl)-phenol 119837-35-3 C11H14N2O
4-(4,5,6,7-Tetrahydro-1H-[1,2]diazepin-3-yl)-phenol
—— 2,2'-(((1E,1'E)-((((E)-but-2-ene-1,4-diyl)bis(oxy))bis(3-methoxy-4,1-phenylene))bis(methaneylylidene))bis(azaneylylidene))bis(4-methylphenol) 1310801-03-6 C34H34N2O6
2,2'-(((1E,1'E)-((((E)-but-2-ene-1,4-diyl)bis(oxy))bis(3-methoxy-4,1-phenylene))bis(methaneylylidene))bis(azaneylylidene))bis(4-methylphenol)
—— 6-Brom-2-deutero-isovanillin 4816-01-7 C8H7BrO3
6-Brom-2-deutero-isovanillin
—— 2-<5-Brom-2-hydroxy-phenyl>-1,3,4-oxdiazol 89892-29-5 C8H5BrN2O2
2-<5-Brom-2-hydroxy-phenyl>-1,3,4-oxdiazol
—— 3-Methoxy-2-{[(E)-3-nitro-phenylimino]-methyl}-phenol 127142-97-6 C14H12N2O4
3-Methoxy-2-{[(E)-3-nitro-phenylimino]-methyl}-phenol
—— 4-(α-Methylallyl)-2-aethyl-phenol 41389-52-0 C12H16O
4-(α-Methylallyl)-2-aethyl-phenol
—— Cu(4-hydroxyacetophenone isonicotinoylhydrazone)SO4(H2O)2 497882-46-9 C14H17CuN3O8S
Cu(4-hydroxyacetophenone isonicotinoylhydrazone)SO4(H2O)2
—— ethyl 4-hydroxyphenethyl sulfonate 146465-88-5 C10H14O4S
ethyl 4-hydroxyphenethyl sulfonate
—— 2-Methyl-5-pentadecyl-phenol 95221-75-3 C22H38O
2-Methyl-5-pentadecyl-phenol
—— 2-{[6-(3,4-dichloro-phenylamino)-[1,2,5]ozadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-6-methoxy-phenol 851661-66-0 C18H13Cl2N7O3
2-{[6-(3,4-dichloro-phenylamino)-[1,2,5]ozadiazolo[3,4-b]pyrazin-5-yl]-hydrazonomethyl}-6-methoxy-phenol
—— 3-(2-Hydroxy-ethylamino)-4-methoxy-phenol 29644-14-2 C9H13NO3
3-(2-Hydroxy-ethylamino)-4-methoxy-phenol
—— 2-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-4-nitrophenol 205313-75-3 C20H19N3O4
2-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-4-nitrophenol
—— O-<2,3-Distearoyloxy-propyl-(1)>-O'-(β-phthalimido-ethyl)-O'-<3-carbobenzoxyglycyloxy-2-hydroxy-propyl(1)>-phosphorsaeure 15150-62-6 C62H99N2O15P
O-<2,3-Distearoyloxy-propyl-(1)>-O'-(β-phthalimido-ethyl)-O'-<3-carbobenzoxyglycyloxy-2-hydroxy-propyl(1)>-phosphorsaeure
—— (4-Hydroxy-phenyl)-methylamino-methanesulfonic acid 64576-87-0 C8H11NO4S
(4-Hydroxy-phenyl)-methylamino-methanesulfonic acid