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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-tert-butyl-4-methoxy-5-methyl-phenol 107058-18-4 C12H18O2
2-tert-butyl-4-methoxy-5-methyl-phenol
—— 2-(4-benzyloxy-3,5-dimethoxyphenyl)ethanol 868732-20-1 C17H20O4
2-(4-benzyloxy-3,5-dimethoxyphenyl)ethanol
—— 7-(3-Chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-ol 499236-19-0 C11H13ClO
7-(3-Chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-ol
—— 5-Amino-4-fluoro-2-(1-methylcyclooctyl)phenol 873055-51-7 C15H22FNO
5-Amino-4-fluoro-2-(1-methylcyclooctyl)phenol
—— trans-4-Crotyl-2.6-dimethyl-phenol 41389-75-7 C12H16O
trans-4-Crotyl-2.6-dimethyl-phenol
—— Phenol, 4-(3,6-dihydro-4-methyl-2H-pyran-2-yl)-2-methoxy- 128489-02-1 C13H16O3
Phenol, 4-(3,6-dihydro-4-methyl-2H-pyran-2-yl)-2-methoxy-
—— (6-fluoro-2-hydroxy-3-methylphenyl)boronic acid 2121513-74-2 C7H8BFO3
(6-fluoro-2-hydroxy-3-methylphenyl)boronic acid
—— 4-[3-[2-[2-[3-(4-Hydroxy-3-methoxyphenyl)propylsulfanyl]ethyldisulfanyl]ethylsulfanyl]propyl]-2-methoxyphenol 623947-87-5 C24H34O4S4
4-[3-[2-[2-[3-(4-Hydroxy-3-methoxyphenyl)propylsulfanyl]ethyldisulfanyl]ethylsulfanyl]propyl]-2-methoxyphenol
—— N-cyclohexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide 58418-75-0 C15H21NO3
N-cyclohexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— 4-Chlor-2-brom-6-aethylphenol 53347-02-7 C8H8BrClO
4-Chlor-2-brom-6-aethylphenol
—— (S)-methyl 3-(4-hydroxyphenyl)heptanoate 1073546-39-0 C14H20O3
(S)-methyl 3-(4-hydroxyphenyl)heptanoate
—— methyl (3R)-3-(4-hydroxy-3-methylphenyl)hexanoate 1073546-19-6 C14H20O3
methyl (3R)-3-(4-hydroxy-3-methylphenyl)hexanoate
—— 5-Bromo-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2-methylphenol 905450-27-3 C14H23BrO3Si
5-Bromo-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2-methylphenol
—— (S)-methyl 3-(4-hydroxyphenyl)hept-4-ynoate 1073547-36-0 C14H16O3
(S)-methyl 3-(4-hydroxyphenyl)hept-4-ynoate
—— methyl (3R)-3-(3-bromo-4-hydroxyphenyl)hexanoate 1073546-13-0 C13H17BrO3
methyl (3R)-3-(3-bromo-4-hydroxyphenyl)hexanoate
—— methyl (3R)-3-(4-hydroxyphenyl)hexanoate 1073545-35-3 C13H18O3
methyl (3R)-3-(4-hydroxyphenyl)hexanoate
—— (R)-methyl 3-(4-hydroxyphenyl)hept-4-ynoate 1073547-38-2 C14H16O3
(R)-methyl 3-(4-hydroxyphenyl)hept-4-ynoate
—— (R)-methyl 3-(4-hydroxyphenyl)heptanoate 1073546-62-9 C14H20O3
(R)-methyl 3-(4-hydroxyphenyl)heptanoate
—— (S,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate 1073546-54-9 C14H18O3
(S,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate
—— (R,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate 1073546-50-5 C14H18O3
(R,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate
—— 2-[2-[4-[2-(2-Hydroxy-3,6-dimethoxyphenyl)ethynyl]phenyl]ethynyl]-3,6-dimethoxyphenol 864670-92-8 C26H22O6
2-[2-[4-[2-(2-Hydroxy-3,6-dimethoxyphenyl)ethynyl]phenyl]ethynyl]-3,6-dimethoxyphenol
—— 3-hydroxy-6-nitro-4-(2-propenyl)benzylalcohol 869562-12-9 C10H11NO4
3-hydroxy-6-nitro-4-(2-propenyl)benzylalcohol
—— 5-bromo-2-(2-fluoro-3-hydroxyphenyl)-6-methyl-3-(2-phenylethyl)-4(3H)-pyrimidinone 938180-95-1 C19H16BrFN2O2
5-bromo-2-(2-fluoro-3-hydroxyphenyl)-6-methyl-3-(2-phenylethyl)-4(3H)-pyrimidinone
—— N-cyclopropyl-2,2,2-trifluoro-N-(4-hydroxy-3-nitrophenyl)acetamide 897953-52-5 C11H9F3N2O4
N-cyclopropyl-2,2,2-trifluoro-N-(4-hydroxy-3-nitrophenyl)acetamide
—— methyl (3R)-4,4,4-trifluoro-3-(3-hydroxyphenyl)butanoate 1142222-99-8 C11H11F3O3
methyl (3R)-4,4,4-trifluoro-3-(3-hydroxyphenyl)butanoate
—— methyl (3S)-4,4,4-trifluoro-3-(3-hydroxyphenyl)butanoate 1142223-00-4 C11H11F3O3
methyl (3S)-4,4,4-trifluoro-3-(3-hydroxyphenyl)butanoate
—— ethyl 2-[(3-hydroxybenzyl)thio]-2-methylpropionate 672931-10-1 C13H18O3S
ethyl 2-[(3-hydroxybenzyl)thio]-2-methylpropionate
—— 2,4-Dibromo-6-(1-methylcyclopropyl)phenol 1124145-87-4 C10H10Br2O
2,4-Dibromo-6-(1-methylcyclopropyl)phenol
—— ethyl (2-fluoro-5-hydroxyphenyl)acetate 672931-29-2 C10H11FO3
ethyl (2-fluoro-5-hydroxyphenyl)acetate
—— [(3S)-3-amino-3-carboxypropyl][(2-hydroxy-3,5-dinitrophenyl)hydroxymethyl]phosphinic acid 936234-68-3 C11H14N3O10P
[(3S)-3-amino-3-carboxypropyl][(2-hydroxy-3,5-dinitrophenyl)hydroxymethyl]phosphinic acid
—— [(3S)-3-amino-3-carboxypropyl][(6-hydroxy-3-nitrophenyl)hydroxymethyl]phosphinic acid 936234-74-1 C11H15N2O8P
[(3S)-3-amino-3-carboxypropyl][(6-hydroxy-3-nitrophenyl)hydroxymethyl]phosphinic acid
—— [(3S)-3-amino-3-carboxypropyl][(2-hydroxy-3-nitrophenyl)hydroxymethyl]phosphinic acid 936234-70-7 C11H15N2O8P
[(3S)-3-amino-3-carboxypropyl][(2-hydroxy-3-nitrophenyl)hydroxymethyl]phosphinic acid
—— 3-chloro-4-ethoxy-2-fluorophenol 909122-52-7 C8H8ClFO2
3-chloro-4-ethoxy-2-fluorophenol
—— methyl (3R)-3-(4-hydroxyphenyl)-5-methyl-4-hexenoate 1012070-83-5 C14H18O3
methyl (3R)-3-(4-hydroxyphenyl)-5-methyl-4-hexenoate
—— methyl (3S)-3-(4-hydroxyphenyl)-5-methyl-4-hexenoate 1012070-85-7 C14H18O3
methyl (3S)-3-(4-hydroxyphenyl)-5-methyl-4-hexenoate
—— 2-ethyl-5-fluorophenol 1147351-77-6 C8H9FO
2-ethyl-5-fluorophenol
—— 5-(4-{[(2-Ethylhexyl)oxy]methyl}-1,3-dioxolan-2-YL)-2-methoxyphenol 918789-84-1 C19H30O5
5-(4-{[(2-Ethylhexyl)oxy]methyl}-1,3-dioxolan-2-YL)-2-methoxyphenol
—— 2-Methoxy-5-(4-methyl-1,3-dioxan-2-yl)phenol 918789-81-8 C12H16O4
2-Methoxy-5-(4-methyl-1,3-dioxan-2-yl)phenol
—— 2-(6-amino-1-hydroxyhexyl)-4-(2-chloroethyl)-phenol 910212-67-8 C14H22ClNO2
2-(6-amino-1-hydroxyhexyl)-4-(2-chloroethyl)-phenol
—— ((R)-1-{[5-Fluoro-2-(5-hydroxy-2-methoxy-phenyl)-pyrimidin-4-ylamino]-methyl}-propyl)-carbamic acid tert-butyl ester 956125-25-0 C20H27FN4O4
((R)-1-{[5-Fluoro-2-(5-hydroxy-2-methoxy-phenyl)-pyrimidin-4-ylamino]-methyl}-propyl)-carbamic acid tert-butyl ester
—— d10-3,5-dimethylphenol 1192812-51-3 C8H10O
d10-3,5-dimethylphenol
—— (5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-67-6 C17H20FN3O3S
(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-2-[(2R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— 3-Phosphanylphenol 63578-56-3 C6H7OP
3-Phosphanylphenol
—— tert-butyl 2-[(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]pyrazolidine-1-carboxylate 1181083-16-8 C18H20FN3O4S
tert-butyl 2-[(5Z)-5-[(5-fluoro-2-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]pyrazolidine-1-carboxylate
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(pyrazolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181082-81-4 C13H12FN3O2S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(pyrazolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— (5Z)-2-(azetidin-1-yl)-5-[(2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one 1181081-65-1 C13H12N2O2S
(5Z)-2-(azetidin-1-yl)-5-[(2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one
—— (Z)-5-(4-Fluoro-2-hydroxybenzylidene)-2-thioxothiazolidin-4-one 1181082-93-8 C10H6FNO2S2
(Z)-5-(4-Fluoro-2-hydroxybenzylidene)-2-thioxothiazolidin-4-one
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(methylsulfanyl)-4,5-dihydro-1,3-oxazol-4-one 1181081-67-3 C11H9NO3S
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(methylsulfanyl)-4,5-dihydro-1,3-oxazol-4-one
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(2S)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one 1181082-78-9 C17H20FN3O3S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-[(2S)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl]-4,5-dihydro-1,3-thiazol-4-one
—— 2,2,2-trifluoro-N-[(1R)-1-(3-hydroxyphenyl)ethyl]acetamide 1056614-99-3 C10H10F3NO2
2,2,2-trifluoro-N-[(1R)-1-(3-hydroxyphenyl)ethyl]acetamide