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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
—— 5-Methoxy-2-[1-(propylamino)ethyl]phenol 1042523-97-6 C12H19NO2
5-Methoxy-2-[1-(propylamino)ethyl]phenol
—— 2-(2,2,2-Trichloro-1-hydroxyethyl)phenol 59648-33-8 C8H7Cl3O2
2-(2,2,2-Trichloro-1-hydroxyethyl)phenol
—— 3-(3-Hydroxyhex-5-enyl)-2-methoxyphenol 1265278-90-7 C13H18O3
3-(3-Hydroxyhex-5-enyl)-2-methoxyphenol
—— 2-[1-(Butylamino)ethyl]-5-methoxyphenol 1038259-02-7 C13H21NO2
2-[1-(Butylamino)ethyl]-5-methoxyphenol
—— 2-[1-(cyclohexylamino)ethyl]-5-methoxyphenol 1042613-83-1 C15H23NO2
2-[1-(cyclohexylamino)ethyl]-5-methoxyphenol
—— 5-Methoxy-2-[1-(propan-2-ylamino)ethyl]phenol 1038230-91-9 C12H19NO2
5-Methoxy-2-[1-(propan-2-ylamino)ethyl]phenol
—— 2-methoxy-3-[(1R)-1-phenylmethoxyhex-5-enyl]phenol 1265279-11-5 C20H24O3
2-methoxy-3-[(1R)-1-phenylmethoxyhex-5-enyl]phenol
—— 2-(2,2,2-trichloro-1-hydroxyethyl)-4-chlorophenol 72422-56-1 C8H6Cl4O2
2-(2,2,2-trichloro-1-hydroxyethyl)-4-chlorophenol
—— 4-chloro-2-methyl-5-nitro-phenol 19044-75-8 C7H6ClNO3
4-chloro-2-methyl-5-nitro-phenol
—— HOC6H4CHN(i-Pr) 13033-49-3 C10H13NO
HOC6H4CHN(i-Pr)
—— 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione 212755-08-3 C12H6ClF4N3O5
1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione
—— N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester 59834-03-6 C11H14N2O3
N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester
—— cylindrocyclophane B 141854-65-1 C38H58O7
cylindrocyclophane B
—— cyclindrocyclophane D 141854-67-3 C40H60O8
cyclindrocyclophane D
—— (-)-cylindrocyclophane A 126693-92-3 C36H56O6
(-)-cylindrocyclophane A
—— (2E,2'E)-N,N-[2,2'-disulfanediylbis(propane-3,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] 1071822-33-7 C24H28Br2N4O6S2
(2E,2'E)-N,N-[2,2'-disulfanediylbis(propane-3,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— 4-(2-hydroxy-4-methoxyphenyl)-1-phenylpentan-3-one 1607446-79-6 C18H20O3
4-(2-hydroxy-4-methoxyphenyl)-1-phenylpentan-3-one
—— 2-(3-hydroxyphenyl)thiazole 35582-13-9 C9H7NOS
2-(3-hydroxyphenyl)thiazole
—— 2-(2-Methylsulfonylethyl)phenol 56490-39-2 C9H12O3S
2-(2-Methylsulfonylethyl)phenol
—— (3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 172484-39-8 C26H26O8
(3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
—— (-)-phyllodulcin 172588-04-4 C16H14O5
(-)-phyllodulcin
—— 1-Methyl-2-o-hydroxyphenylcyclopropan 29026-04-8 C10H12O
1-Methyl-2-o-hydroxyphenylcyclopropan
—— diethyl 4-hydroxy-3-methoxybenzylmalonate 86726-49-0 C15H20O6
diethyl 4-hydroxy-3-methoxybenzylmalonate
—— 4,5-dimethoxy-2-(2-benzyloxyethyl)benzaldehyde 406215-49-4 C18H20O4
4,5-dimethoxy-2-(2-benzyloxyethyl)benzaldehyde
—— N-(4,5-dimethylisoxazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide 948573-58-8 C14H16N2O4
N-(4,5-dimethylisoxazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide
—— 2-[(diphenylphosphanyl)methyl]phenol 75637-59-1 C19H17OP
2-[(diphenylphosphanyl)methyl]phenol
—— N-(3,4-dihydroxybenzyl)-4,5-dimethylfuran-2-carboxamide 1186647-17-5 C14H15NO4
N-(3,4-dihydroxybenzyl)-4,5-dimethylfuran-2-carboxamide
—— 3,4-dihydroxybenzylamine hydrochloride 1124-40-9 C7H9NO2*ClH
3,4-dihydroxybenzylamine hydrochloride
—— 2-[(Dimethylamino)methyl]-4-methyl-6-nitrophenol 731843-23-5 C10H14N2O3
2-[(Dimethylamino)methyl]-4-methyl-6-nitrophenol
—— 2-bromo-3-methylbenzene-1,4-diol 40492-40-8 C7H7BrO2
2-bromo-3-methylbenzene-1,4-diol
—— 3-(2,3-Dihydroxy-phenyl)-propionsaeureamid 91004-66-9 C9H11NO3
3-(2,3-Dihydroxy-phenyl)-propionsaeureamid
—— [9]-demethoxyshogaol 1057075-33-8 C18H26O2
[9]-demethoxyshogaol
—— 2-(4-hydroxyphenyl)-3-(2-(piperidin-1-yl)ethyl)thiazolidin-4-one 1443534-62-0 C16H22N2O2S
2-(4-hydroxyphenyl)-3-(2-(piperidin-1-yl)ethyl)thiazolidin-4-one
—— tetrahydro-5-(1-hydroxyethyl)-4-(2-hydroxyphenyl)-3,6-dimethyl-2H-1,3-oxazin-2-one 75208-76-3 C14H19NO4
tetrahydro-5-(1-hydroxyethyl)-4-(2-hydroxyphenyl)-3,6-dimethyl-2H-1,3-oxazin-2-one
—— 2-Aminomethyl-4-chloro-3,6-dimethoxy-phenol 343773-24-0 C9H12ClNO3
2-Aminomethyl-4-chloro-3,6-dimethoxy-phenol
—— 4-methyl-2-(p-tolylethynyl)phenol 1338699-35-6 C16H14O
4-methyl-2-(p-tolylethynyl)phenol
—— (2E,4E)-5-(3,4-di-hydroxyphenyl)penta-2,4-dienoic acid 1073666-65-5 C11H10O4
(2E,4E)-5-(3,4-di-hydroxyphenyl)penta-2,4-dienoic acid
—— (2E,4E)-N-benzyl-5-(4-hydroxy-3-methoxyphenyl)penta-2,4-dienamide 878800-18-1 C19H19NO3
(2E,4E)-N-benzyl-5-(4-hydroxy-3-methoxyphenyl)penta-2,4-dienamide
—— ethyl (2E,4E)-5-[4-hydroxy-3-methoxyphenyl]penta-2,4-dienoate 1093121-07-3 C14H16O4
ethyl (2E,4E)-5-[4-hydroxy-3-methoxyphenyl]penta-2,4-dienoate
—— 5-[(indol-2-ylmethyl-amino)-methyl]-2-methoxy-phenol 109731-02-4 C17H18N2O2
5-[(indol-2-ylmethyl-amino)-methyl]-2-methoxy-phenol
—— ethyl 2-(2-hydroxy-5-methoxyphenyl)acetate 76196-45-7 C11H14O4
ethyl 2-(2-hydroxy-5-methoxyphenyl)acetate
—— Grevillin D 54707-49-2 C18H12O8
Grevillin D
—— 2-(3,4-dihydroxybenzene)thiophene, 1067911-36-7 C10H8O2S
2-(3,4-dihydroxybenzene)thiophene,
—— 3,4,5-trimethoxy-2,6-bis(3-methylbut-2-enyl)phenol 1316850-61-9 C19H28O4
3,4,5-trimethoxy-2,6-bis(3-methylbut-2-enyl)phenol
—— 4-(Dibutyl-ethyl-silanyloxymethyl)-2-methoxy-phenol 79523-71-0 C18H32O3Si
4-(Dibutyl-ethyl-silanyloxymethyl)-2-methoxy-phenol
—— <tetrahydropyrannyloxy-2'>-2 trimethoxy-3,4,5 phenol 118971-72-5 C14H20O5
<tetrahydropyrannyloxy-2'>-2 trimethoxy-3,4,5 phenol
—— 2-chloro-3,4,5-trimethoxyphenol 201288-71-3 C9H11ClO4
2-chloro-3,4,5-trimethoxyphenol
—— 2-bromo-3,4,5-trimethoxyphenol 99180-09-3 C9H11BrO4
2-bromo-3,4,5-trimethoxyphenol
—— (Z)-3-((E)-1-(propoxyimino)ethyl)-4-hydroxy-5-(4-hydroxybenzylidene)-1,5-dihydro-2H-pyrrole-2-one 1262232-51-8 C16H18N2O4
(Z)-3-((E)-1-(propoxyimino)ethyl)-4-hydroxy-5-(4-hydroxybenzylidene)-1,5-dihydro-2H-pyrrole-2-one
—— N,N'-bis(2,3-dihydroxybenzylidene)-1,3-diamino-2,2-dimethylpropane 141233-05-8 C19H22N2O4
N,N'-bis(2,3-dihydroxybenzylidene)-1,3-diamino-2,2-dimethylpropane