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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
—— 2-(2-Hydroxy-5-methyl-phenyl)-thiazolidin 78760-56-2 C10H13NOS
2-(2-Hydroxy-5-methyl-phenyl)-thiazolidin
—— 5-(2-Hydroxyphenyl)-2-propan-2-ylimino-1,3-thiazolidin-4-one 1628629-69-5 C12H14N2O2S
5-(2-Hydroxyphenyl)-2-propan-2-ylimino-1,3-thiazolidin-4-one
—— 3'-methoxy-4'-hydroxy-N-methylacetanilide 102683-60-3 C10H13NO3
3'-methoxy-4'-hydroxy-N-methylacetanilide
—— 2-(3-hydroxyphenyl)-3-ethoxycarbonyl-2,5-dihydrofuran 1041333-74-7 C13H14O4
2-(3-hydroxyphenyl)-3-ethoxycarbonyl-2,5-dihydrofuran
—— (Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-3-hexyl-2-isopropylimino-thiazolidin-4-one 1228116-87-7 C19H25ClN2O2S
(Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-3-hexyl-2-isopropylimino-thiazolidin-4-one
—— 1146684-92-5 C46H40N6O10S2
—— N,N'-(1,2-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide) 1146684-93-6 C46H40N6O10S2
N,N'-(1,2-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide)
—— 2,5-dibromo-3,6-dimethylbenzene-1,4-diol 848320-35-4 C8H8Br2O2
2,5-dibromo-3,6-dimethylbenzene-1,4-diol
—— 1-(4-hydroxyphenyl)-2-(3-pyridyl)ethane 85666-07-5 C13H13NO
1-(4-hydroxyphenyl)-2-(3-pyridyl)ethane
—— 4-(2-hydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 1269025-34-4 C16H21NO3
4-(2-hydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
—— (Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-isopropylimino-3-phenethyl-thiazolidin-4-one 1228117-07-4 C21H21ClN2O2S
(Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-isopropylimino-3-phenethyl-thiazolidin-4-one
—— 4-ethylthio-3-hydroxynitrobenzene 146310-47-6 C8H9NO3S
4-ethylthio-3-hydroxynitrobenzene
—— 5-formyl-4-hydroxy-3-methoxy-2-(methylthio)benzonitrile 1245744-75-5 C10H9NO3S
5-formyl-4-hydroxy-3-methoxy-2-(methylthio)benzonitrile
—— 2-hydroxy-1-methoxy-3-<2-((methoxycarbonyl)amino)ethyl>benzene 141849-19-6 C11H15NO4
2-hydroxy-1-methoxy-3-<2-((methoxycarbonyl)amino)ethyl>benzene
—— 5-acetyl-1-(3,4-dimethoxy-2-hydroxyphenethyl)-2-piperidinone 89680-95-5 C17H23NO5
5-acetyl-1-(3,4-dimethoxy-2-hydroxyphenethyl)-2-piperidinone
—— 5,5-dimethyl-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene 116911-86-5 C16H24O3
5,5-dimethyl-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene
—— 4-(3,5-dimethoxy-4-hydroxyphenyl)-1-butene 112468-44-7 C12H16O3
4-(3,5-dimethoxy-4-hydroxyphenyl)-1-butene
—— 2,6-dimethoxy-4-((tetrahydro-2H-pyran-2-yloxy)methyl)phenol 1443015-26-6 C14H20O5
2,6-dimethoxy-4-((tetrahydro-2H-pyran-2-yloxy)methyl)phenol
—— (E)-4-methyl-2-(prop-1-enyl)phenol 65001-69-6 C10H12O
(E)-4-methyl-2-(prop-1-enyl)phenol
—— 3-(2-(4-Hydroxyphenyl)ethyl)sydnone imine monohydrochloride 37744-03-9 C10H12ClN3O2
3-(2-(4-Hydroxyphenyl)ethyl)sydnone imine monohydrochloride
—— 3-nitro-4-{[(2-(pyridin-4-yl)(1,3-thiazol-4-yl))amino]methyl}phenol 630411-31-3 C15H12N4O3S
3-nitro-4-{[(2-(pyridin-4-yl)(1,3-thiazol-4-yl))amino]methyl}phenol
—— Phenethyl propionate plus eugenol (7:3) 37262-61-6 C21H26O4
Phenethyl propionate plus eugenol (7:3)
—— 2-Chloro-5-methoxy-3,6-dimethyl-phenol 89711-29-5 C9H11ClO2
2-Chloro-5-methoxy-3,6-dimethyl-phenol
—— 2-allyl-1,4-dihydroxy-5-methylbenzene 79950-53-1 C10H12O2
2-allyl-1,4-dihydroxy-5-methylbenzene
—— O,O,O',O'-tetraethyl [(2,6-dihydroxyphenyl)methylene]bis(phosphonothioate) 1262020-43-8 C15H26O6P2S2
O,O,O',O'-tetraethyl [(2,6-dihydroxyphenyl)methylene]bis(phosphonothioate)
—— 3-Hydroxy-benzoldiazonium 30984-22-6 C6H5N2O
3-Hydroxy-benzoldiazonium
—— (+/-)-4-(2-acetylamino-1-methylethyl)phenol 114963-24-5 C11H15NO2
(+/-)-4-(2-acetylamino-1-methylethyl)phenol
—— 1,2-Dimethyl-4-n-propyl-4-(m-hydroxyphenyl)-piperidazin 39126-77-7 C15H24N2O
1,2-Dimethyl-4-n-propyl-4-(m-hydroxyphenyl)-piperidazin
—— (3-ethyl-2,4-dihydroxy-5-methyl-phenyl)-glyoxylic acid 412018-98-5 C11H12O5
(3-ethyl-2,4-dihydroxy-5-methyl-phenyl)-glyoxylic acid
—— 3-hydroxybenzocyclobutenedione 62416-21-1 C8H4O3
3-hydroxybenzocyclobutenedione
—— 5-amino-25,26,27,28-tetrahydroxycalix[4]arene 836608-54-9 C28H25NO4
5-amino-25,26,27,28-tetrahydroxycalix[4]arene
—— (2E,5E)-2,5-bis(3-allyl-4-hydroxybenzylidene)cyclopentanone 1548331-45-8 C25H24O3
(2E,5E)-2,5-bis(3-allyl-4-hydroxybenzylidene)cyclopentanone
—— 4-bromo-2-fluoro-3,5-dimethylphenol 1000413-90-0 C8H8BrFO
4-bromo-2-fluoro-3,5-dimethylphenol
—— 2-Nitro-4-chlor-6-cyan-phenol 88310-62-7 C7H3ClN2O3
2-Nitro-4-chlor-6-cyan-phenol
—— 2-amino-4-chloro-5-methoxyphenol 87701-48-2 C7H8ClNO2
2-amino-4-chloro-5-methoxyphenol
—— (4-fluoro-m-hydroxyphenethyl)guanidine 889882-04-6 C9H12FN3O
(4-fluoro-m-hydroxyphenethyl)guanidine
—— 6-bromo-2-hydroxy-3-methoxybenzyl alcohol 35090-65-4 C8H9BrO3
6-bromo-2-hydroxy-3-methoxybenzyl alcohol
—— 6-bromo-3-chloro-2,4-bis(methoxymethoxy)phenol 1449247-12-4 C10H12BrClO5
6-bromo-3-chloro-2,4-bis(methoxymethoxy)phenol
—— 3-chloro-2,4-bis(methoxymethoxy)phenol 1449247-11-3 C10H13ClO5
3-chloro-2,4-bis(methoxymethoxy)phenol
—— 5-bromo-2-methylbenzene-1,3-diol 253604-37-4 C7H7BrO2
5-bromo-2-methylbenzene-1,3-diol
—— 5-bromo-4-iodo-2-methylphenol 849726-21-2 C7H6BrIO
5-bromo-4-iodo-2-methylphenol
—— 2,3-difluoro-4-heptyl-6-methylphenol 1026225-18-2 C14H20F2O
2,3-difluoro-4-heptyl-6-methylphenol
—— 5-hydroxy-1-[3-(furan-3-yl)-3-oxo-prop-1-yl]-benzocyclobutene-1-carbonitrile ethylene ketal 1174640-90-4 C18H17NO4
5-hydroxy-1-[3-(furan-3-yl)-3-oxo-prop-1-yl]-benzocyclobutene-1-carbonitrile ethylene ketal
—— 2-[3-[(2-Hydroxyphenyl)methylideneamino]butyliminomethyl]phenol 5337-12-2 C18H20N2O2
2-[3-[(2-Hydroxyphenyl)methylideneamino]butyliminomethyl]phenol
—— 2-Hydroxy-n-{2-[(2-hydroxyethyl)amino]ethyl}-3,5-dinitrobenzamide 5336-40-3 C11H14N4O7
2-Hydroxy-n-{2-[(2-hydroxyethyl)amino]ethyl}-3,5-dinitrobenzamide
—— dibutyl 4-hydroxybenzylphosphonate 146465-93-2 C15H25O4P
dibutyl 4-hydroxybenzylphosphonate
—— β-nitroisoeugenol 5395-47-1 C10H11NO4
β-nitroisoeugenol
—— ethyl 2-(3-methyl-4-hydroxy)-phenylthio-acetate 949018-92-2 C11H14O3S
ethyl 2-(3-methyl-4-hydroxy)-phenylthio-acetate
—— 4-ethylsulfanyl-2-methylphenol 18979-85-6 C9H12OS
4-ethylsulfanyl-2-methylphenol
—— 2-methyl-4-(prop-2-ynylthio)phenol 772-57-6 C10H10OS
2-methyl-4-(prop-2-ynylthio)phenol