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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
—— (S)-3-(3-bromo-4-hydroxy-phenyl)-2-ethoxy-propionic acid isopropyl ester 719293-76-2 C14H19BrO4
(S)-3-(3-bromo-4-hydroxy-phenyl)-2-ethoxy-propionic acid isopropyl ester
—— 4-(4-Cyclohexyl-butyl)-phenol 1760-64-1 C16H24O
4-(4-Cyclohexyl-butyl)-phenol
—— 6-[[1-(2-hydroxyphenyl)ethylamino]methylidene]cyclohexa-2,4-dien-1-one 89985-54-6 C15H15NO2
6-[[1-(2-hydroxyphenyl)ethylamino]methylidene]cyclohexa-2,4-dien-1-one
—— 1228930-91-3 C16H17ClO4S
—— 4-methyl-2-(triisopropylsilyl)phenol 241490-82-4 C16H28OSi
4-methyl-2-(triisopropylsilyl)phenol
—— 5-[4-(2-hydroxy-5-methylphenyl)-1,3-oxazol-2-yl]pentanoic acid 847266-88-0 C15H17NO4
5-[4-(2-hydroxy-5-methylphenyl)-1,3-oxazol-2-yl]pentanoic acid
—— cis-1.2-Bis-salicylidenamino-cyclobutan 3187-80-2 C18H18N2O2
cis-1.2-Bis-salicylidenamino-cyclobutan
—— diethyl 3,5-diiodo-4-hydroxybenzylphosphonate 852947-34-3 C11H15I2O4P
diethyl 3,5-diiodo-4-hydroxybenzylphosphonate
—— 2-hydroxy-acetophenone-(2-hydroxy-benzylamine) 4226-32-8 C15H15NO2
2-hydroxy-acetophenone-(2-hydroxy-benzylamine)
—— N-sek.Butyl-3-O-methyl-noradrenalin 6924-33-0 C13H21NO3
N-sek.Butyl-3-O-methyl-noradrenalin
—— 15480-60-1 C17H16N4O2S2
—— 5-[2-(benzyloxy)-4,6-dihydroxyphenyl]-N-(1-methylpiperidin-4-yl)isoxazole-3-carboxamide 1253585-46-4 C23H25N3O5
5-[2-(benzyloxy)-4,6-dihydroxyphenyl]-N-(1-methylpiperidin-4-yl)isoxazole-3-carboxamide
—— 4-Chloro-2-[(3-methyl-2-butenoxyimino)methyl]phenol 103743-08-4 C12H14ClNO2
4-Chloro-2-[(3-methyl-2-butenoxyimino)methyl]phenol
—— 3-(2-amino-ethylsulfanyl)-5-methyl-benzene-1,2-diol; hydrochloride 27320-86-1 C9H13NO2S*ClH
3-(2-amino-ethylsulfanyl)-5-methyl-benzene-1,2-diol; hydrochloride
—— 2-amino-3,6-difluoro-4-methylphenol 1784521-29-4 C7H7F2NO
2-amino-3,6-difluoro-4-methylphenol
—— N-(3-Hydroxy-4-methoxyphenethyl)-2-(2-brom-4,5-methylendioxyphenyl)-acetamid 17889-68-8 C18H18BrNO5
N-(3-Hydroxy-4-methoxyphenethyl)-2-(2-brom-4,5-methylendioxyphenyl)-acetamid
—— 5-(1-hexylcyclobutyl)resorcinol 941583-84-2 C16H24O2
5-(1-hexylcyclobutyl)resorcinol
—— 2-Aethoxycarbonyl-3-<2-hydroxyphenyl>-5-<5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on 3967-79-1 C21H19FO5
2-Aethoxycarbonyl-3-<2-hydroxyphenyl>-5-<5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on
—— 2-Aethoxycarbonyl-3-phenyl-5-<3-chlor-5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on 3979-19-9 C21H18ClFO4
2-Aethoxycarbonyl-3-phenyl-5-<3-chlor-5-fluor-2-hydroxyphenyl>-cyclohex-5-en-1-on
—— 11-(2,5-dihydroxyphenyl)-1-(thioacetyl)undecane 401846-18-2 C19H30O3S
11-(2,5-dihydroxyphenyl)-1-(thioacetyl)undecane
—— (2,5-dihydroxy-4-methoxy-phenyl)-malonic acid dimethyl ester 100118-66-9 C12H14O7
(2,5-dihydroxy-4-methoxy-phenyl)-malonic acid dimethyl ester
—— 2,4-Dinitro-phenol; compound with 4-dimethylamino-benzaldehyde 39194-31-5 C6H4N2O5*C9H11NO
2,4-Dinitro-phenol; compound with 4-dimethylamino-benzaldehyde
—— N,N'-Di-[5-(2-dimethylaminoethoxy)salicylidene]ethylenediamine 147539-16-0 C24H34N4O4
N,N'-Di-[5-(2-dimethylaminoethoxy)salicylidene]ethylenediamine
—— 2-(2,6-Dibromo-4-hydroxy-phenoxy)-N,N-diethyl-acetamide 23899-10-7 C12H15Br2NO3
2-(2,6-Dibromo-4-hydroxy-phenoxy)-N,N-diethyl-acetamide
—— 4-Hydroxy-2,6-dimethylbenzenediazonium;chloride 74808-88-1 C8H9N2O*Cl
4-Hydroxy-2,6-dimethylbenzenediazonium;chloride
—— 2-(salicylideneamino)-1-hydroxyethane 16327-96-1 C9H11NO2
2-(salicylideneamino)-1-hydroxyethane
—— Hydroquinone mono(2-octyloxypropyl) ether 109233-59-2 C17H28O3
Hydroquinone mono(2-octyloxypropyl) ether
—— p-(Methylthiomethylthio)-o-kresol 37708-58-0 C9H12OS2
p-(Methylthiomethylthio)-o-kresol
—— 1-(2,4-dihydroxyphenyl)-4,5-dihydro-1H-pyrazole 1202819-49-5 C9H10N2O2
1-(2,4-dihydroxyphenyl)-4,5-dihydro-1H-pyrazole
—— decanoic acid [5-(4-hydroxy-3,5-dimethoxy-benzylidene)-2-(4-hydroxy-3,5-dimethoxy-phenyl)-4-oxo-thiazolidin-3-yl]amide 1290139-37-5 C30H40N2O8S
decanoic acid [5-(4-hydroxy-3,5-dimethoxy-benzylidene)-2-(4-hydroxy-3,5-dimethoxy-phenyl)-4-oxo-thiazolidin-3-yl]amide
—— N,N'-bis(salicylidene)-4,5-methoxy-1,2-phenylenediamine 219318-73-7 C22H20N2O4
N,N'-bis(salicylidene)-4,5-methoxy-1,2-phenylenediamine
—— 2-(4-Hydroxy-phenyl)-5,5-dimethyl-4-phenyl-2,5-dihydro-imidazol-1-ol 122981-58-2 C17H18N2O2
2-(4-Hydroxy-phenyl)-5,5-dimethyl-4-phenyl-2,5-dihydro-imidazol-1-ol
—— 5-(4-hydroxy-3-methoxyphenyl)-3H-1,3,4-oxadiazole-2-thione 1391739-44-8 C9H8N2O3S
5-(4-hydroxy-3-methoxyphenyl)-3H-1,3,4-oxadiazole-2-thione
—— 2-(4-hydroxyphenyl)-4,4-dimethyl-2-oxazoline 124438-10-4 C11H13NO2
2-(4-hydroxyphenyl)-4,4-dimethyl-2-oxazoline
—— 1237740-82-7 C14H18O
—— diethyl (4-hydroxy-3-methoxyphenyl)(benzo[d]thiazol-2-ylamino)methylphosphonate 1202183-86-5 C19H23N2O5PS
diethyl (4-hydroxy-3-methoxyphenyl)(benzo[d]thiazol-2-ylamino)methylphosphonate
—— 3-[2'-hydroxy-5'-nitrophenyl]-1,2-benzisoxazole 2-oxide 1316277-38-9 C13H8N2O5
3-[2'-hydroxy-5'-nitrophenyl]-1,2-benzisoxazole 2-oxide
—— 4-(2-phenylfuran-3-yl)phenol 132590-04-6 C16H12O2
4-(2-phenylfuran-3-yl)phenol
—— 2-(Bis-propylsulfanyl-methyl)-phenol 24396-31-4 C13H20OS2
2-(Bis-propylsulfanyl-methyl)-phenol
—— 3,4-dihydro-8-hydroxy-4-methyl-1H-2-benzopyran-1-one 135217-45-7 C10H10O3
3,4-dihydro-8-hydroxy-4-methyl-1H-2-benzopyran-1-one
—— (O,O-Dimethyl-phosphono)-carbamidsaeure-(4,6-dihydroxy-phenylester) 13664-44-3 C9H12NO7P
(O,O-Dimethyl-phosphono)-carbamidsaeure-(4,6-dihydroxy-phenylester)
—— 2,5-Bis-<(2-hydroxy-aethylamino)-methyl>-hydrochinon 128885-69-8 C12H20N2O4
2,5-Bis-<(2-hydroxy-aethylamino)-methyl>-hydrochinon
—— N-(3-hydroxypyridine-2-yl)-5-methylsalicylideneimine 1151855-01-4 C13H12N2O2
N-(3-hydroxypyridine-2-yl)-5-methylsalicylideneimine
—— 4-[(E)-1,2,4-triazol-1-yliminomethyl]benzene-1,2-diol 324033-15-0 C9H8N4O2
4-[(E)-1,2,4-triazol-1-yliminomethyl]benzene-1,2-diol
—— 2-Chlor-4-<4-hydroxy-3-methoxy-phenyl>-thiazol 90799-67-0 C10H8ClNO2S
2-Chlor-4-<4-hydroxy-3-methoxy-phenyl>-thiazol
—— m-2-selenienylphenol 75073-55-1 C10H8OSe
m-2-selenienylphenol
—— 2,4-dibromo-6-[(2-isopropylaminoethylimino)methyl]phenol 1174288-06-2 C12H16Br2N2O
2,4-dibromo-6-[(2-isopropylaminoethylimino)methyl]phenol
—— Acetyl-(3,5,6-trichlor-2-hydroxy-phenylhydrazono)-essigsaeure-aethylester 21103-92-4 C12H11Cl3N2O4
Acetyl-(3,5,6-trichlor-2-hydroxy-phenylhydrazono)-essigsaeure-aethylester
—— 4-(4-Hydroxy-3,5-dimethyl-phenyl)-1-oxo-1,2-dihydro-5H-2,3-benzodiazepin 20435-67-0 C17H16N2O2
4-(4-Hydroxy-3,5-dimethyl-phenyl)-1-oxo-1,2-dihydro-5H-2,3-benzodiazepin
—— 2-[1,2-Bis-(phenyl-hydrazono)-ethyl]-5-methoxy-phenol 7397-18-4 C21H20N4O2
2-[1,2-Bis-(phenyl-hydrazono)-ethyl]-5-methoxy-phenol