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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-(4-hydroxyphenyl)-1,2,3-selenadiazole 52376-65-5 C8H6N2OSe
4-(4-hydroxyphenyl)-1,2,3-selenadiazole
—— 4-bromo-2-(phenylselanyl)phenol 1350814-86-6 C12H9BrOSe
4-bromo-2-(phenylselanyl)phenol
—— 2-(phenylselanyl)phenol 57483-19-9 C12H10OSe
2-(phenylselanyl)phenol
—— 3-[(diphenylphosphinoyl)methyl]benzene-1,2-diol 922721-33-3 C19H17O3P
3-[(diphenylphosphinoyl)methyl]benzene-1,2-diol
—— (S)-2-(1-aminoethyl)-5-methylphenol 1213532-58-1 C9H13NO
(S)-2-(1-aminoethyl)-5-methylphenol
—— 3-[(diphenylphosphorothioyl)-methyl]-benzene-1,2-diol 1318239-75-6 C19H17O2PS
3-[(diphenylphosphorothioyl)-methyl]-benzene-1,2-diol
—— 4-[[(3-Ethoxypropyl)amino]methyl]-2,6-dimethoxyphenol 1038225-24-9 C14H23NO4
4-[[(3-Ethoxypropyl)amino]methyl]-2,6-dimethoxyphenol
—— (-)-3-((R)-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol 155836-68-3 C20H25BrN2OS
(-)-3-((R)-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol
—— 6-nitroso-5-fluororesorcinol 851128-79-5 C6H4FNO3
6-nitroso-5-fluororesorcinol
—— (+/-)-3-((R*)-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol —— C20H25BrN2OS
(+/-)-3-((R*)-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol
—— 2-methyl-5-(8Z,11Z)-8,11,14-pentadecatrienyl-1,3-benzenediol 50423-15-9 C22H32O2
2-methyl-5-(8Z,11Z)-8,11,14-pentadecatrienyl-1,3-benzenediol
—— 5-(2,4-Dihydroxy-phenyl)-valeriansaeure 4654-14-2 C11H14O4
5-(2,4-Dihydroxy-phenyl)-valeriansaeure
—— 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine 114207-82-8 C32H38N2O9
2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine
—— 5-[2-hexyl-1,3-dithian-2-yl]resorcinol 579444-48-7 C16H24O2S2
5-[2-hexyl-1,3-dithian-2-yl]resorcinol
—— 5-(1-hexylcyclopentyl)resorcinol 487578-68-7 C17H26O2
5-(1-hexylcyclopentyl)resorcinol
—— 5-[1,3]dithiolan-2-ylbenzene-1,3-diol 60081-20-1 C9H10O2S2
5-[1,3]dithiolan-2-ylbenzene-1,3-diol
—— 5-(1-adamantyl)methylresorcinol 861892-39-9 C17H22O2
5-(1-adamantyl)methylresorcinol
—— 3-Methoxy-2-(9-methyldecyl)-5-pentylphenol 69505-76-6 C23H40O2
3-Methoxy-2-(9-methyldecyl)-5-pentylphenol
—— 2-Decyl-5-pentylresorcin-monomethylether 69505-80-2 C22H38O2
2-Decyl-5-pentylresorcin-monomethylether
—— methyl 3-(4-hydroxy-3-methylphenyl)propanoate 22516-91-2 C11H14O3
methyl 3-(4-hydroxy-3-methylphenyl)propanoate
—— 5-(4-hydroxy-3-methylphenyl)-2-furanecarboxaldehyde 627906-59-6 C12H10O3
5-(4-hydroxy-3-methylphenyl)-2-furanecarboxaldehyde
—— 4-(2-amino-4-thiazolyl)-2-methylphenol 199602-16-9 C10H10N2OS
4-(2-amino-4-thiazolyl)-2-methylphenol
—— 2-(4-Hydroxy-phenyl)-pentan-3-one 111873-61-1 C11H14O2
2-(4-Hydroxy-phenyl)-pentan-3-one
—— US8877795, Diclofenac 2143472-42-6 C14H12ClNO3
US8877795, Diclofenac
—— 5-(6-chlorohexyl)benzene-1,3-diol 870789-85-8 C12H17ClO2
5-(6-chlorohexyl)benzene-1,3-diol
—— 5-octylbenzene-1,3-diol 46733-28-2 C14H22O2
5-octylbenzene-1,3-diol
—— 5-(2,2-Dibromo-1-hexyl-cyclopropyl)-benzene-1,3-diol 499237-41-1 C15H20Br2O2
5-(2,2-Dibromo-1-hexyl-cyclopropyl)-benzene-1,3-diol
—— 5-(1-hexyl-cyclopropyl)resorcinol 499237-34-2 C15H22O2
5-(1-hexyl-cyclopropyl)resorcinol
—— 5-(2,2-Dichloro-1-hexyl-cyclopropyl)-benzene-1,3-diol 499237-40-0 C15H20Cl2O2
5-(2,2-Dichloro-1-hexyl-cyclopropyl)-benzene-1,3-diol
—— 3-hydroxy-4-cyclohexylethynylbenzene 1174270-86-0 C14H16O
3-hydroxy-4-cyclohexylethynylbenzene
—— 2-(cyclohex-1-en-1-ylethynyl)phenol 1286764-01-9 C14H14O
2-(cyclohex-1-en-1-ylethynyl)phenol
—— p-methoxyphenol-d3 54536-24-2 C7H8O2
p-methoxyphenol-d3
—— 1-[1-(2-Hydroxyphenyl)ethylideneamino]-3-phenylthiourea —— C15H15N3OS
1-[1-(2-Hydroxyphenyl)ethylideneamino]-3-phenylthiourea
—— 4-(4-hydroxyphenyl)-nonane 6465-78-7 C15H24O
4-(4-hydroxyphenyl)-nonane
—— 4-(3,5-dihydroxyphenyl)-1-bromobutane 1260669-57-5 C10H13BrO2
4-(3,5-dihydroxyphenyl)-1-bromobutane
—— 4-n-hexyl-catechol 2524-98-3 C12H18O2
4-n-hexyl-catechol
—— 2,6-Dinitro-4-(1-aethylhexyl)-phenol 4137-13-7 C14H20N2O5
2,6-Dinitro-4-(1-aethylhexyl)-phenol
—— methylhexylphenol 17404-42-1 C13H20O
methylhexylphenol
—— 2-(1-methylhexyl)-4,6-dinitrophenol 4097-38-5 C13H18N2O5
2-(1-methylhexyl)-4,6-dinitrophenol
—— 2-(1-Pentylhexyl)-phenol 17404-54-5 C17H28O
2-(1-Pentylhexyl)-phenol
—— 4,6-Dinitro-2-(1-aethyl-hexyl)-phenol 4275-64-3 C14H20N2O5
4,6-Dinitro-2-(1-aethyl-hexyl)-phenol
—— 4-(1-Butylhexyl)-phenol 6465-79-8 C16H26O
4-(1-Butylhexyl)-phenol
—— 4-(1-Pentylhexyl)-phenol 6465-72-1 C17H28O
4-(1-Pentylhexyl)-phenol
—— 1-(2-hydroxy-4,6-dimethoxyphenyl)but-2-en-1-one 119228-01-2 C12H14O4
1-(2-hydroxy-4,6-dimethoxyphenyl)but-2-en-1-one
—— 4,5-dinitro-2-(β-hydroxyethoxy)phenol 105780-31-2 C8H8N2O7
4,5-dinitro-2-(β-hydroxyethoxy)phenol
—— (3S,4R,5S,6S,7R,11E,18S,19R,20S,21S,22R,26E)-4,5,6,15,19,20,21,30-octahydroxy-2,9,17,24,33,36-hexaoxapentacyclo[26.2.2.213,16.13,7.118,22]hexatriaconta-1(30),11,13,15,26,28,31,34-octaene-10,25-dione 1306739-93-4 C30H32O16
(3S,4R,5S,6S,7R,11E,18S,19R,20S,21S,22R,26E)-4,5,6,15,19,20,21,30-octahydroxy-2,9,17,24,33,36-hexaoxapentacyclo[26.2.2.213,16.13,7.118,22]hexatriaconta-1(30),11,13,15,26,28,31,34-octaene-10,25-dione
—— 3-methoxy-4-hydroxy mandelic acid 41093-71-4 C9H10O5
3-methoxy-4-hydroxy mandelic acid
—— (2E,4E)-methyl 5-(3,5-dihydroxyphenyl)penta-2,4-dienoate 120467-32-5 C12H12O4
(2E,4E)-methyl 5-(3,5-dihydroxyphenyl)penta-2,4-dienoate
—— 1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene 504396-87-6 C11H16O2
1,3-dihydroxy-5-[4'-(2H2)-5'-(2H3)-pentyl]benzene
—— 1,3-dihydroxy-5-[5'-(2H3)-pentyl]benzene 58545-61-2 C11H16O2
1,3-dihydroxy-5-[5'-(2H3)-pentyl]benzene