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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
—— 6-hydroxy-5-nitro-toluene-3-sulfonyl fluoride 348-98-1 C7H6FNO5S
6-hydroxy-5-nitro-toluene-3-sulfonyl fluoride
—— 4,6-diiodo-2-[[(2,6-dimethylphenyl)imino]methyl]phenol 597564-08-4 C15H13I2NO
4,6-diiodo-2-[[(2,6-dimethylphenyl)imino]methyl]phenol
—— 129352-37-0 C14H19N3OS2*H3N
—— 1410797-34-0 C47H56N2O7
—— 4-hydroxyphenethyl sulfamate 1375959-13-9 C8H11NO4S
4-hydroxyphenethyl sulfamate
—— 2,4-Dibromo-6-[2-(4-hydroxyphenyl)ethyliminomethyl]phenol 1369431-99-1 C15H13Br2NO2
2,4-Dibromo-6-[2-(4-hydroxyphenyl)ethyliminomethyl]phenol
—— 5-benzylidene-2-[{5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one 1248828-33-2 C18H12N4O2S2
5-benzylidene-2-[{5-(2-hydroxyphenyl)-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one
—— Methyl-2-(3',4'-dihydroxyphenyl)-propionat 29207-03-2 C10H12O4
Methyl-2-(3',4'-dihydroxyphenyl)-propionat
—— dopaminophenylglyoxime 1055339-33-7 C16H17N3O4
dopaminophenylglyoxime
—— benzaldehyde-(2-hydroxy-4-methoxy-phenylimine) 339221-81-7 C14H13NO2
benzaldehyde-(2-hydroxy-4-methoxy-phenylimine)
—— N-[1-(2-hydroxy-3-nitrophenyl)ethylideneamino]-3-methylbenzamide 1235578-07-0 C16H15N3O4
N-[1-(2-hydroxy-3-nitrophenyl)ethylideneamino]-3-methylbenzamide
—— 2,4-Dibrom-6-trimethylsilyl-phenol 55454-56-3 C9H12Br2OSi
2,4-Dibrom-6-trimethylsilyl-phenol
—— 6-(3,4-dihydroxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one 39499-67-7 C10H10N2O3
6-(3,4-dihydroxy-phenyl)-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— 2-Brom-4-<6-hydroxy-4-methyl-phenyl>-thiazol 101862-31-1 C10H8BrNOS
2-Brom-4-<6-hydroxy-4-methyl-phenyl>-thiazol
—— 1611470-80-4 C21H24N2O3
—— [1,4]benzoquinone monooxime; protonated form 25426-72-6 C6H5NO2*H
[1,4]benzoquinone monooxime; protonated form
—— 2-(5-(tert-butyldimethylsilyloxy)-1-hydroxypent-2-ynyl)-4-nitrophenol 1599371-42-2 C17H25NO5Si
2-(5-(tert-butyldimethylsilyloxy)-1-hydroxypent-2-ynyl)-4-nitrophenol
—— N-methyl-bis(2-hydroxyethyl)ammonium 2-nitrophenolate 1585976-72-2 C5H13NO2*C6H5NO3
N-methyl-bis(2-hydroxyethyl)ammonium 2-nitrophenolate
—— 2-(4-chloro-phenyl)-4,5-dihydro-oxazole; picrate 39147-13-2 C6H3N3O7*C9H8ClNO
2-(4-chloro-phenyl)-4,5-dihydro-oxazole; picrate
—— N,N-di-(2-methoxyethyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276702-75-1 C12H17ClN2O7S
N,N-di-(2-methoxyethyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— 1-(2-hydroxy-5-methyl)benzylimidazole 75340-97-5 C11H12N2O
1-(2-hydroxy-5-methyl)benzylimidazole
—— 5'-Brom-salicyliden-5-chlor-2-amino-pyridin 73447-03-7 C12H8BrClN2O
5'-Brom-salicyliden-5-chlor-2-amino-pyridin
—— vanillin-(4-chloro-2,6-dinitro-phenylhydrazone) 106271-57-2 C14H11ClN4O6
vanillin-(4-chloro-2,6-dinitro-phenylhydrazone)
—— 4-Nitro-2-hydroxy-ω-furfuryliden-acetophenon 99847-51-5 C13H9NO5
4-Nitro-2-hydroxy-ω-furfuryliden-acetophenon
—— 4-Benzyloxy-2-hydroxymethyl-5-methoxy-phenaethylalkohol 67645-17-4 C17H20O4
4-Benzyloxy-2-hydroxymethyl-5-methoxy-phenaethylalkohol
—— 4-(3-bromopropyl)-2-cyclohexylphenol 1005515-85-4 C15H21BrO
4-(3-bromopropyl)-2-cyclohexylphenol
—— N-(4,5-dimethyl-1H-pyrazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide 952059-65-3 C14H17N3O3
N-(4,5-dimethyl-1H-pyrazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide
—— (+/-)-2-phenyl-(3a<i>r</i>,13<i>at</i>)-3a,4,5,6,7,8,9,10,11,12,13,13a-dodecahydro-cyclododecoxazole; picrate 121812-76-8 C6H3N3O7*C19H27NO
(+/-)-2-phenyl-(3a<i>r</i>,13<i>at</i>)-3a,4,5,6,7,8,9,10,11,12,13,13a-dodecahydro-cyclododecoxazole; picrate
—— 4-chloro-<i>N</i>,<i>N</i>'-bis-(2-hydroxy-5-nitro-benzylidene)-<i>o</i>-phenylenediamine 111241-25-9 C20H13ClN4O6
4-chloro-<i>N</i>,<i>N</i>'-bis-(2-hydroxy-5-nitro-benzylidene)-<i>o</i>-phenylenediamine
—— 2-methoxy-4-methyl-8-(3-nitropropyl)-5,8-dihydronaphthalene-1-ol 252233-77-5 C15H19NO4
2-methoxy-4-methyl-8-(3-nitropropyl)-5,8-dihydronaphthalene-1-ol
—— Hypholomine B 62350-94-1 C26H18O10
Hypholomine B
—— 4,4-bis(3,4-dihydroxy-5-methoxyphenyl)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one 1263203-42-4 C25H24N2O7
4,4-bis(3,4-dihydroxy-5-methoxyphenyl)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one
—— 3-[4]piperidyl-propionic acid vanillylidenehydrazide 101437-32-5 C16H23N3O3
3-[4]piperidyl-propionic acid vanillylidenehydrazide
—— 3-(2,4-dihydroxybenzyl)-4-hydroxy-1-(morpholin-4-yl)butan-1-one 1515406-31-1 C15H21NO5
3-(2,4-dihydroxybenzyl)-4-hydroxy-1-(morpholin-4-yl)butan-1-one
—— 2-Methoxy-6-{[(E)-4-methoxy-phenylimino]-methyl}-4-methyl-phenol 68040-33-5 C16H17NO3
2-Methoxy-6-{[(E)-4-methoxy-phenylimino]-methyl}-4-methyl-phenol
—— 5,6-Dihydro-2-o-hydroxyphenyl-4-methyl-4H-1,3,4-oxadiazin-5-on 28669-25-2 C10H10N2O3
5,6-Dihydro-2-o-hydroxyphenyl-4-methyl-4H-1,3,4-oxadiazin-5-on
—— N-{1-[3-(4-hydroxyphenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}acetamide 625122-05-6 C14H16N4O3
N-{1-[3-(4-hydroxyphenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}acetamide
—— N-(2-hydroxy-3-methoxy-5-methylbenzyl)-t-butylamine 73822-24-9 C13H21NO2
N-(2-hydroxy-3-methoxy-5-methylbenzyl)-t-butylamine
—— 2,5-Bis-(2-hydroxy-3,5-dimethyl-benzyl)-benzochinon-(1,4) 2246-38-0 C24H24O4
2,5-Bis-(2-hydroxy-3,5-dimethyl-benzyl)-benzochinon-(1,4)
—— 4-[2-(3-octyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-57-3 C18H24N2O3
4-[2-(3-octyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— o-Arsinophenol 66089-13-2 C6H7AsO
o-Arsinophenol
—— vanillin-(2-bromo-5-nitro-phenylhydrazone) 100542-42-5 C14H12BrN3O4
vanillin-(2-bromo-5-nitro-phenylhydrazone)
—— thiazolidine-2,4-dione-2-[1-(2-hydroxy-5-methoxy-phenyl)-ethylLiDenehydrazone] 108899-77-0 C12H13N3O3S
thiazolidine-2,4-dione-2-[1-(2-hydroxy-5-methoxy-phenyl)-ethylLiDenehydrazone]
—— 6,6'-((isopropylthio)methylene)bis(4-chloro-2-nitrophenol) 71319-60-3 C16H14Cl2N2O6S
6,6'-((isopropylthio)methylene)bis(4-chloro-2-nitrophenol)
—— 142274-58-6 C22H19N5O6
—— 4-amino-2-fluoro-3-methylphenol 1379301-63-9 C7H7ClFNO
4-amino-2-fluoro-3-methylphenol
—— 6,15,24-tri-tert-butyl-9,18,27-trihydroxy<3.3.3>metacyclophane 170159-37-2 C39H54O3
6,15,24-tri-tert-butyl-9,18,27-trihydroxy<3.3.3>metacyclophane
—— 4-[2-(3-pentyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-51-7 C15H18N2O3
4-[2-(3-pentyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 2-hydroxy-3,5-dibromobenzaldehyde-O-(2-(aminooxy)ethyl)oxime 1370040-70-2 C9H10Br2N2O3
2-hydroxy-3,5-dibromobenzaldehyde-O-(2-(aminooxy)ethyl)oxime
—— 5,5'-bis-(4-hydroxy-3-methoxy-benzylidene)-2,2'-m-phenylenediamino-bis-thiazol-4-one 24234-14-8 C28H22N4O6S2
5,5'-bis-(4-hydroxy-3-methoxy-benzylidene)-2,2'-m-phenylenediamino-bis-thiazol-4-one