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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
—— 2,3-bis(4-hydroxyphenyl)-2-cyclopropen-1-one 25361-95-9 C15H10O3
2,3-bis(4-hydroxyphenyl)-2-cyclopropen-1-one
—— 1414651-83-4 C28H38O8
—— 2-ethyl-4-tetradecoxyphenol 140466-78-0 C22H38O2
2-ethyl-4-tetradecoxyphenol
—— methyl 2-hydroxy-3,5-dinitro-α-toluenesulphonate 56276-23-4 C8H8N2O8S
methyl 2-hydroxy-3,5-dinitro-α-toluenesulphonate
—— 4-Hydroxy-3-iodo-5-methylbenzonitrile 1608148-61-3 C8H6INO
4-Hydroxy-3-iodo-5-methylbenzonitrile
—— N-cyclohexyl-5-hydroxy-2-methoxybenzamide 1052106-87-2 C14H19NO3
N-cyclohexyl-5-hydroxy-2-methoxybenzamide
—— [1R,3S] 3,4-dihydro-5-hydroxy-1-nitromethyl-3-phenyl-1H-2-benzopyran 138231-40-0 C16H15NO4
[1R,3S] 3,4-dihydro-5-hydroxy-1-nitromethyl-3-phenyl-1H-2-benzopyran
—— 4-(hydrazonomethyl)-1,2-benzenediol, trifluoroacetate salt 114875-19-3 C2HF3O2*C7H8N2O2
4-(hydrazonomethyl)-1,2-benzenediol, trifluoroacetate salt
—— N-[1-(2-hydroxy-4-methoxyphenyl)ethylideneamino]-2-methylbenzamide 1235837-43-0 C17H18N2O3
N-[1-(2-hydroxy-4-methoxyphenyl)ethylideneamino]-2-methylbenzamide
—— 3-(4-hydroxy-2-nitro-phenyl)-propionic acid-(4-bromo-anilide) 109365-47-1 C15H13BrN2O4
3-(4-hydroxy-2-nitro-phenyl)-propionic acid-(4-bromo-anilide)
—— (2R,2'R)-3,3'-dihydroxy-4,4'-bis(4-hydrophenyl)-2,2'-bifuran-5,5'(2H,2'H)-dione 1233689-99-0 C20H14O8
(2R,2'R)-3,3'-dihydroxy-4,4'-bis(4-hydrophenyl)-2,2'-bifuran-5,5'(2H,2'H)-dione
—— (E)-ethyl-2-((E)-(4-hydroxy-3,5-dimethoxy benzylidene)hydrazono)-3,4-dimethyl-2,3-dihydro-thiazole-5-carboxylate 1446892-01-8 C17H21N3O5S
(E)-ethyl-2-((E)-(4-hydroxy-3,5-dimethoxy benzylidene)hydrazono)-3,4-dimethyl-2,3-dihydro-thiazole-5-carboxylate
—— 4-[(4-Tert-butyl-2-cyclohexylimino-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,3-triol 1459803-37-2 C20H27N3O3S
4-[(4-Tert-butyl-2-cyclohexylimino-1,3-thiazol-3-yl)iminomethyl]benzene-1,2,3-triol
—— o-(3-Aethoxyheptyl)-phenyl 19346-79-3 C15H24O2
o-(3-Aethoxyheptyl)-phenyl
—— dodecyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide 29812-05-3 Br*C22H40NO2
dodecyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide
—— 4-(1-Hydroxy-2-isopropylamino-ethyl)-3-methoxy-benzene-1,2-diol 20261-73-8 C12H19NO4
4-(1-Hydroxy-2-isopropylamino-ethyl)-3-methoxy-benzene-1,2-diol
—— 2-[2]furyl-3-(2-hydroxy-phenyl)-thiazolidin-4-one 107625-03-6 C13H11NO3S
2-[2]furyl-3-(2-hydroxy-phenyl)-thiazolidin-4-one
—— 5-bromo-2-nitro-3-propylphenol 94102-95-1 C9H10BrNO3
5-bromo-2-nitro-3-propylphenol
—— 4-[1-(2-Hydroxy-phenyl)-eth-(E)-ylideneamino]-5-methyl-2,4-dihydro-[1,2,4]triazole-3-thione 119120-39-7 C11H12N4OS
4-[1-(2-Hydroxy-phenyl)-eth-(E)-ylideneamino]-5-methyl-2,4-dihydro-[1,2,4]triazole-3-thione
—— 2-hydroxy-4,6-diisopropoxybenzaldehyde 215163-07-8 C13H18O4
2-hydroxy-4,6-diisopropoxybenzaldehyde
—— 4-[2-(4,6-Dimethyl-pyrimidin-2-ylamino)-ethyl]-benzene-1,2-diol 107585-48-8 C14H17N3O2
4-[2-(4,6-Dimethyl-pyrimidin-2-ylamino)-ethyl]-benzene-1,2-diol
—— 1389250-16-1 C18H12BrN3O2S
—— (+/-)-benzoic acid-(<i>trans</i>-2-amino-cyclohexyl ester); picrate 102082-73-5 C6H3N3O7*C13H17NO2
(+/-)-benzoic acid-(<i>trans</i>-2-amino-cyclohexyl ester); picrate
—— r-1,c-2,t-3,t-4,5,7-hexachlorotetralin-6-ol 21406-13-3 C10H6Cl6O
r-1,c-2,t-3,t-4,5,7-hexachlorotetralin-6-ol
—— N'-(2-Hydroxy-3-methoxybenzylidene)dodecanohydrazide 303086-42-2 C20H32N2O3
N'-(2-Hydroxy-3-methoxybenzylidene)dodecanohydrazide
—— 3-(4-Hydroxy-3-methoxy-phenyl)-propyl-malonsaeure 100613-75-0 C13H16O6
3-(4-Hydroxy-3-methoxy-phenyl)-propyl-malonsaeure
—— sodium 3-methoxy-salicylaldehyde-5-sulfonate 118833-78-6 C8H7O6S*Na
sodium 3-methoxy-salicylaldehyde-5-sulfonate
—— 6-methylheptyl 3-(4-hydroxy-3-methoxyphenyl)propionate 951221-90-2 C18H28O4
6-methylheptyl 3-(4-hydroxy-3-methoxyphenyl)propionate
—— 4-((E)-3-Hydroxy-4-morpholin-4-yl-but-1-enyl)-2-methoxy-phenol 80304-68-3 C15H21NO4
4-((E)-3-Hydroxy-4-morpholin-4-yl-but-1-enyl)-2-methoxy-phenol
—— 4-(4-Cyclohexyl-butyl)-3-methyl-phenol 109251-90-3 C17H26O
4-(4-Cyclohexyl-butyl)-3-methyl-phenol
—— 4,4’-[5,5’-methylenedi-(1,3,4-thiadiazole-2-yl)]di(benzene-1,3-diol) 1447735-05-8 C17H12N4O4S2
4,4’-[5,5’-methylenedi-(1,3,4-thiadiazole-2-yl)]di(benzene-1,3-diol)
—— 5-hydroxy-2-methoxy-N-propan-2-ylbenzamide 1052106-86-1 C11H15NO3
5-hydroxy-2-methoxy-N-propan-2-ylbenzamide
—— (3-Phenyl-propyl)-(4-hydroxy-phenyl)-aether 99304-99-1 C15H16O2
(3-Phenyl-propyl)-(4-hydroxy-phenyl)-aether
—— 2-[1-(5-Chloro-2-hydroxyphenyl)ethylideneamino]acetic acid 286389-03-5 C10H10ClNO3
2-[1-(5-Chloro-2-hydroxyphenyl)ethylideneamino]acetic acid
—— (2-methylsulfanyl-4-phenyl-thiazol-5-yl)-vanillyliden-amine 114616-96-5 C18H16N2O2S2
(2-methylsulfanyl-4-phenyl-thiazol-5-yl)-vanillyliden-amine
—— 3.5-Diiod-synephrin 2208-33-5 C9H11I2NO2
3.5-Diiod-synephrin
—— 2-Methoxy-4-methyl-6-{[(E)-4-nitro-phenylimino]-methyl}-phenol 68040-34-6 C15H14N2O4
2-Methoxy-4-methyl-6-{[(E)-4-nitro-phenylimino]-methyl}-phenol
—— 5-fluorotetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9,11,13(20),15(19),16-nonaene-19,20,21-triol 83153-62-2 C21H17FO3
5-fluorotetracyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9,11,13(20),15(19),16-nonaene-19,20,21-triol
—— 1158814-53-9 C55H69O5*Cs
—— (3,4-dihydroxy-benzylidenedimercapto)-di-acetic acid 34914-23-3 C11H12O6S2
(3,4-dihydroxy-benzylidenedimercapto)-di-acetic acid
—— 4-<2-(2-Chloroethoxy)ethoxy>phenole 165274-92-0 C10H13ClO3
4-<2-(2-Chloroethoxy)ethoxy>phenole
—— diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-methyl-N-(2-pyridyl)-amino]-ethylphosphonate 407583-86-2 C20H29N2O5P
diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-methyl-N-(2-pyridyl)-amino]-ethylphosphonate
—— 1,21,23,25-tetrakis(2-phenylethyl)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis<1,3>dioxocino<5,4-i:5',4'-i'>benzo<1,2-d:5,4-d'>-bis<1,3>benzodioxocin-7,15-diol 136538-43-7 C64H56O10
1,21,23,25-tetrakis(2-phenylethyl)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis<1,3>dioxocino<5,4-i:5',4'-i'>benzo<1,2-d:5,4-d'>-bis<1,3>benzodioxocin-7,15-diol
—— 3-Cyclopropylmethyl-5-(1-hydroxyethyl)-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-9-ol 86110-90-9 C23H31NO3
3-Cyclopropylmethyl-5-(1-hydroxyethyl)-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-9-ol
—— 3-(2,4-dihydroxybenzyl)-4-hydroxy-N-octylbutanamide 1515405-99-8 C19H31NO4
3-(2,4-dihydroxybenzyl)-4-hydroxy-N-octylbutanamide
—— 4-Chloro-2-{[(E)-2-(3H-imidazol-4-ylmethylsulfanyl)-ethylimino]-methyl}-phenol 101221-11-8 C13H14ClN3OS
4-Chloro-2-{[(E)-2-(3H-imidazol-4-ylmethylsulfanyl)-ethylimino]-methyl}-phenol
—— di-t-butyl (2-hydroxy-4-methylphenyl) phosphate 124982-87-2 C15H25O4P
di-t-butyl (2-hydroxy-4-methylphenyl) phosphate
—— 1-(4-Hydroxy-phenyl)-ethanone O-(3-tert-butylamino-2-hydroxy-propyl)-oxime 64434-05-5 C15H24N2O3
1-(4-Hydroxy-phenyl)-ethanone O-(3-tert-butylamino-2-hydroxy-propyl)-oxime
—— 2-[5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-methyl-phenol 37689-59-1 C23H22N2O2
2-[5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-methyl-phenol
—— 3,5-diethyl-4-iodophenol 845622-61-9 C10H13IO
3,5-diethyl-4-iodophenol