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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-(3-hydroxy-4-methylphenyl)-4-dimethylaminocyclohexanone ethylene ketal 65620-24-8 C17H25NO3
4-(3-hydroxy-4-methylphenyl)-4-dimethylaminocyclohexanone ethylene ketal
—— N,N-dimethyl-N'-(1-methylimidazole-2-ylmethyl)-N'-(2-hydroxy-4-nitrobenzyl)ethylenediamine 779332-64-8 C16H23N5O3
N,N-dimethyl-N'-(1-methylimidazole-2-ylmethyl)-N'-(2-hydroxy-4-nitrobenzyl)ethylenediamine
—— 5-Hydroxy-phosphinine-2-carboxylic acid 109541-67-5 C6H5O3P
5-Hydroxy-phosphinine-2-carboxylic acid
—— 3-pentyl-3,4-dihydro-quinazolin-8-ol 131762-59-9 C13H18N2O
3-pentyl-3,4-dihydro-quinazolin-8-ol
—— 4-methyl-2-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-phenol 22812-25-5 C16H15NO2
4-methyl-2-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-phenol
—— 11,17,23-tri-tert-butyl-26,27,28-trihydroxy-5-methylcalix<4>arene 175349-02-7 C41H50O3
11,17,23-tri-tert-butyl-26,27,28-trihydroxy-5-methylcalix<4>arene
—— 3-[(E)-piperidin-1-yliminomethyl]benzene-1,2-diol 473421-25-9 C12H16N2O2
3-[(E)-piperidin-1-yliminomethyl]benzene-1,2-diol
—— 3-<(2-Hydroxy-phenyl)methylenamino>pyrazolin 91633-96-4 C10H11N3O
3-<(2-Hydroxy-phenyl)methylenamino>pyrazolin
—— 3,5-dimethoxy-6-(phenylethynyl)-2-(1-(trimethylsilyl)-1(E)-butenyl)-1,4-benzenediol 173913-05-8 C23H28O4Si
3,5-dimethoxy-6-(phenylethynyl)-2-(1-(trimethylsilyl)-1(E)-butenyl)-1,4-benzenediol
—— 2,4,6-Tris-(trimethylsilyl)-phenol 15013-29-3 C15H30OSi3
2,4,6-Tris-(trimethylsilyl)-phenol
—— 5-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-isoxazol-3-yl-phenol 502423-51-0 C19H23NO3
5-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-isoxazol-3-yl-phenol
—— cobalt(II) 2-((2-(3-(2-(2-hydroxybenzylidene)hydrazineyl)-3-oxopropanoyl)hydrazineylidene)methyl)phenolate chloride 81421-28-5 C17H15N4O4*Cl*Co
cobalt(II) 2-((2-(3-(2-(2-hydroxybenzylidene)hydrazineyl)-3-oxopropanoyl)hydrazineylidene)methyl)phenolate chloride
—— 3-(2'-hydroxyphenyl)-5-phenyl-1,2,4-triazine 118207-07-1 C15H11N3O
3-(2'-hydroxyphenyl)-5-phenyl-1,2,4-triazine
—— 2,6-Di-n-octyl-4-methoxy-phenol 114002-63-0 C23H40O2
2,6-Di-n-octyl-4-methoxy-phenol
—— 3-hydroxy-2,4,6-trinitro-benzoic acid methyl ester 57731-64-3 C8H5N3O9
3-hydroxy-2,4,6-trinitro-benzoic acid methyl ester
—— lanthanum(III) 3-((2-hydroxybenzylidene)amino)propanoate 3-((2-oxidobenzylidene)amino)propanoate 53058-95-0 C10H9NO3*C10H10NO3*La
lanthanum(III) 3-((2-hydroxybenzylidene)amino)propanoate 3-((2-oxidobenzylidene)amino)propanoate
—— N=C(Me)O-N(Me)-C(H)(o-C6H4OH) 267238-23-3 C10H12N2O2
N=C(Me)O-N(Me)-C(H)(o-C6H4OH)
—— 1,2-Bis-(5-jod-2-hydroxy-3-methoxy-benzylidenamino)-ethan 7396-76-1 C18H18I2N2O4
1,2-Bis-(5-jod-2-hydroxy-3-methoxy-benzylidenamino)-ethan
—— 2,6-Dinitro-4-(1-methyl-cyclohexyl)-phenol 100616-69-1 C13H16N2O5
2,6-Dinitro-4-(1-methyl-cyclohexyl)-phenol
—— 4-(4-chloro-3,5-dinitro-phenyl-<i>ONN</i>-azoxy)-2,6-dinitro-phenol 117100-33-1 C12H5ClN6O10
4-(4-chloro-3,5-dinitro-phenyl-<i>ONN</i>-azoxy)-2,6-dinitro-phenol
—— tetra-t-butyl (2-hydroxy-5-methyl-1,3-phenylene)bis(phosphonate) 124982-92-9 C23H42O7P2
tetra-t-butyl (2-hydroxy-5-methyl-1,3-phenylene)bis(phosphonate)
—— 2-hydroxy-3-methoxy-5-pyrrolidinomethyl-benzaldehyde semicarbazone 109443-57-4 C14H20N4O3
2-hydroxy-3-methoxy-5-pyrrolidinomethyl-benzaldehyde semicarbazone
—— 2,2'-di-<i>tert</i>-butyl-6,6'-dimethyl-4,4'-(6-chloro-[1,3,5]triazine-2,4-diyldiamino)-bis-phenol 66009-81-2 C25H32ClN5O2
2,2'-di-<i>tert</i>-butyl-6,6'-dimethyl-4,4'-(6-chloro-[1,3,5]triazine-2,4-diyldiamino)-bis-phenol
—— 2-hydroxy-5-chloro-1-(α-p-chlorophenylimino)ethyl benzene 105533-46-8 C14H11Cl2NO
2-hydroxy-5-chloro-1-(α-p-chlorophenylimino)ethyl benzene
—— 2,4-Diamino-m-cresol 123739-79-7 C7H10N2O
2,4-Diamino-m-cresol
—— 4-Bromo-2-[3-(trifluoromethyl)-1,2-oxazol-5-yl]phenol 929960-93-0 C10H5BrF3NO2
4-Bromo-2-[3-(trifluoromethyl)-1,2-oxazol-5-yl]phenol
—— 4-Methoxy-4.4-bis-<2-hydroxy-4-methoxy-phenyl>-crotonsaeuremethylester 94757-86-5 C20H22O7
4-Methoxy-4.4-bis-<2-hydroxy-4-methoxy-phenyl>-crotonsaeuremethylester
—— 3-(2-hydroxy-5-methylphenyl)-5-(p-chlorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 1267528-41-5 C17H16ClN3OS
3-(2-hydroxy-5-methylphenyl)-5-(p-chlorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
—— 132352-01-3 C48H60Br4O8
—— 4-Thiazolidinone, 5-((4-hydroxy-3-methoxyphenyl)methylene)-3-(((2-methoxyphenyl)amino)methyl)-2-thioxo- 89752-51-2 C19H18N2O4S2
4-Thiazolidinone, 5-((4-hydroxy-3-methoxyphenyl)methylene)-3-(((2-methoxyphenyl)amino)methyl)-2-thioxo-
—— N'-(2-hydroxy-5-methylbenzylidene)-1H-pyrrole-2-carbohydrazide 929684-64-0 C13H13N3O2
N'-(2-hydroxy-5-methylbenzylidene)-1H-pyrrole-2-carbohydrazide
—— 3-Hydroxy-2-methoxybenzenesulfonic acid 111617-97-1 C7H8O5S
3-Hydroxy-2-methoxybenzenesulfonic acid
—— 2-(neopentylphenylphosphanyl)phenol 1233669-58-3 C17H21OP
2-(neopentylphenylphosphanyl)phenol
—— 1447448-27-2 C17H16O
—— 2-Methoxy-4-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol; hydrobromide 94427-28-8 BrH*C13H17NO2
2-Methoxy-4-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol; hydrobromide
—— 2-(6-Methyl-3,7-dioxa-bicyclo[4.1.0]hept-4-yl)-phenol 95081-78-0 C12H14O3
2-(6-Methyl-3,7-dioxa-bicyclo[4.1.0]hept-4-yl)-phenol
—— 2,6-bis(N-methylenemorpholino)-4-nitrophenol 153954-02-0 C16H23N3O5
2,6-bis(N-methylenemorpholino)-4-nitrophenol
—— Carboxyl-salicylsaeure-<sup>14</sup>C 1882-49-1 C7H6O3
Carboxyl-salicylsaeure-<sup>14</sup>C
—— 3,4-Diphenyl-2-(p-hydroxyphenyl)-5-methylfuran 54756-58-0 C23H18O2
3,4-Diphenyl-2-(p-hydroxyphenyl)-5-methylfuran
—— diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-ethylphosphonate 407583-22-6 C20H30N3O6P
diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-ethylphosphonate
—— 2-[(4-tert-butylphenylimino)methyl]-4-methoxyphenol 388096-15-9 C18H21NO2
2-[(4-tert-butylphenylimino)methyl]-4-methoxyphenol
—— N-2-Octyl-2-(4-hydroxy-3-methoxyphenyl)-propionamide 107512-57-2 C18H29NO3
N-2-Octyl-2-(4-hydroxy-3-methoxyphenyl)-propionamide
—— 3-Propyl-1-phenyl-5-(4'-hydroxyphenyl)-Δ<sup>2</sup>-pyrazolin 94067-34-2 C18H20N2O
3-Propyl-1-phenyl-5-(4'-hydroxyphenyl)-Δ<sup>2</sup>-pyrazolin
—— 2-(3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxy-phenyl)propylthio)ethyl methacrylate 1260141-19-2 C22H24ClN3O4S
2-(3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxy-phenyl)propylthio)ethyl methacrylate
—— N-((3s,5s,7s)-adamantan-1-yl)-5-hydroxy-2-methoxybenzamide 1052106-89-4 C18H23NO3
N-((3s,5s,7s)-adamantan-1-yl)-5-hydroxy-2-methoxybenzamide
—— 5-Bromo-2-{[(E)-3-mercapto-[1,2,4]triazol-4-ylimino]-methyl}-phenol 144459-39-2 C9H7BrN4OS
5-Bromo-2-{[(E)-3-mercapto-[1,2,4]triazol-4-ylimino]-methyl}-phenol
—— {2-[4-(1(3)<i>H</i>-imidazol-4-yl)-butyryloxy]-ethyl}-trimethyl-ammonium; dipicrate 121812-50-8 C6H2N3O7*C6H3N3O7*C12H22N3O2
{2-[4-(1(3)<i>H</i>-imidazol-4-yl)-butyryloxy]-ethyl}-trimethyl-ammonium; dipicrate
—— <6-Brom-3-hydroxy-2.4-dimethyl-phenyl>-phosphonsaeure-diaethylester 105911-02-2 C12H18BrO4P
<6-Brom-3-hydroxy-2.4-dimethyl-phenyl>-phosphonsaeure-diaethylester
—— 6-carboethoxy-3-(2-hydroxy-4-methoxyphenyl)-5-phenylcyclohex-2-en-1-one 89059-57-4 C22H22O5
6-carboethoxy-3-(2-hydroxy-4-methoxyphenyl)-5-phenylcyclohex-2-en-1-one
—— 1289641-99-1 C15H26NO4P