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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
—— 5-(8'Z,11'Z-heptadecadienyl)-1,3-benzenediol 138168-58-8 C23H36O2
5-(8'Z,11'Z-heptadecadienyl)-1,3-benzenediol
—— 1-(2-hydroxy-5-nitro-benzyl)-indoline 1262391-74-1 C15H14N2O3
1-(2-hydroxy-5-nitro-benzyl)-indoline
—— 4-hydroxybenzocyclobutene-1,2-dione 75833-48-6 C8H4O3
4-hydroxybenzocyclobutene-1,2-dione
—— 3-hydroxy-5-methylbenzocyclobutenedione 82431-23-0 C9H6O3
3-hydroxy-5-methylbenzocyclobutenedione
—— (E)-1-(4-fluorobenzyl)-5-((4-fluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-88-7 C27H22F2N2O3
(E)-1-(4-fluorobenzyl)-5-((4-fluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-1-benzyl-5-((benzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-84-3 C27H24N2O3
(E)-1-benzyl-5-((benzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-5-((2-hydroxy-4-methoxyphenyl)(pentylimino)methyl)-1-pentylpyridin-2(1H)-one 1201816-97-8 C23H32N2O3
(E)-5-((2-hydroxy-4-methoxyphenyl)(pentylimino)methyl)-1-pentylpyridin-2(1H)-one
—— (E)-5-((2-hydroxy-4-methoxyphenyl)(4-methoxybenzylimino)methyl)-1-(4-methoxybenzyl)pyridin-2(1H)-one 1201816-91-2 C29H28N2O5
(E)-5-((2-hydroxy-4-methoxyphenyl)(4-methoxybenzylimino)methyl)-1-(4-methoxybenzyl)pyridin-2(1H)-one
—— (E)-1-(3,4-difluorobenzyl)-5-((3,4-difluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-90-1 C27H20F4N2O3
(E)-1-(3,4-difluorobenzyl)-5-((3,4-difluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-5-((2-hydroxy-4-methoxyphenyl)(propylimino)methyl)-1-propylpyridin-2(1H)-one 1201816-95-6 C19H24N2O3
(E)-5-((2-hydroxy-4-methoxyphenyl)(propylimino)methyl)-1-propylpyridin-2(1H)-one
—— (E)-1-(2-fluorobenzyl)-5-((2-fluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-85-4 C27H22F2N2O3
(E)-1-(2-fluorobenzyl)-5-((2-fluorobenzylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-5-((2-hydroxy-4-methoxyphenyl)(isopropylimino)methyl)-1-isopropylpyridin-2(1H)-one 1201816-98-9 C19H24N2O3
(E)-5-((2-hydroxy-4-methoxyphenyl)(isopropylimino)methyl)-1-isopropylpyridin-2(1H)-one
—— (E)-1-butyl-5-((butylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-96-7 C21H28N2O3
(E)-1-butyl-5-((butylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-5-((2-hydroxy-4-methoxyphenyl)(4-methylbenzylimino)methyl)-1-(4-methylbenzyl)pyridin-2(1H)-one 1201816-92-3 C29H28N2O3
(E)-5-((2-hydroxy-4-methoxyphenyl)(4-methylbenzylimino)methyl)-1-(4-methylbenzyl)pyridin-2(1H)-one
—— (E)-1-allyl-5-((allylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-99-0 C19H20N2O3
(E)-1-allyl-5-((allylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-1-cyclopropyl-5-((cyclopropylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-94-5 C19H20N2O3
(E)-1-cyclopropyl-5-((cyclopropylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— (E)-1-cyclohexyl-5-((cyclohexylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one 1201816-93-4 C25H32N2O3
(E)-1-cyclohexyl-5-((cyclohexylimino)(2-hydroxy-4-methoxyphenyl)methyl)pyridin-2(1H)-one
—— 1-(4-fluoro-3-hydroxybenzyl)-3-(4-hydroxybenzyl)-1-(1-methylpiperidin-4-yl)urea 1246458-20-7 C21H26FN3O3
1-(4-fluoro-3-hydroxybenzyl)-3-(4-hydroxybenzyl)-1-(1-methylpiperidin-4-yl)urea
—— 1-(4-fluoro-2-hydroxybenzyl)-3-(4-hydroxybenzyl)-1-(1-methylpiperidin-4-yl)urea 1246458-21-8 C21H26FN3O3
1-(4-fluoro-2-hydroxybenzyl)-3-(4-hydroxybenzyl)-1-(1-methylpiperidin-4-yl)urea
—— 4‐(N‐adamantan‐1‐yl)‐1‐[1‐(2‐hydroxybenzylidene)]thiosemicarbazone 32403-31-9 C18H23N3OS
4‐(N‐adamantan‐1‐yl)‐1‐[1‐(2‐hydroxybenzylidene)]thiosemicarbazone
—— 5-(4-hydroxy-3-methoxybenzylidene)-1,3-diphenylpyrimidine-2,4,6(1H,3H,5H)-trione 300830-25-5 C24H18N2O5
5-(4-hydroxy-3-methoxybenzylidene)-1,3-diphenylpyrimidine-2,4,6(1H,3H,5H)-trione
—— α-methyl-2-hydroxy-5-nitrocinnamaldehyde 82380-83-4 C10H9NO4
α-methyl-2-hydroxy-5-nitrocinnamaldehyde
—— 1,4-dihydroxy-2-[(2H3)methyl]-3-methylbenzene 927833-50-9 C8H10O2
1,4-dihydroxy-2-[(2H3)methyl]-3-methylbenzene
—— 2-[(2H3)methyl]-3-methylphenol 927833-45-2 C8H10O
2-[(2H3)methyl]-3-methylphenol
—— bis(2-hydroxyphenyl)-tert-butylphosphine 77013-87-7 C16H19O2P
bis(2-hydroxyphenyl)-tert-butylphosphine
—— 2,4-difluoro-6-methoxyphenol 1193392-90-3 C7H6F2O2
2,4-difluoro-6-methoxyphenol
—— 2-[3-hydroxy-4-nitrophenyl]-1-[6-methylpyridin-2-yl]-ethanone 813449-09-1 C14H12N2O4
2-[3-hydroxy-4-nitrophenyl]-1-[6-methylpyridin-2-yl]-ethanone
—— [(3S)-3-(N-benzyloxycarbonyl)amino-3-methoxycarbonylpropyl][(2-hydroxy-3,5-dinitrophenyl)hydroxymethyl]phosphinic acid 936234-67-2 C20H22N3O12P
[(3S)-3-(N-benzyloxycarbonyl)amino-3-methoxycarbonylpropyl][(2-hydroxy-3,5-dinitrophenyl)hydroxymethyl]phosphinic acid
—— 2S-3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 640293-43-2 C10H14O4
2S-3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol
—— 1,4-dihydroxy-2-methoxy-6-<(Z)-10'-pentadecenyl>benzene 148808-21-3 C22H36O3
1,4-dihydroxy-2-methoxy-6-<(Z)-10'-pentadecenyl>benzene
—— belamcandol A 137786-93-7 C23H38O3
belamcandol A
—— N,N'-(1,4-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide) 1146684-91-4 C46H40N6O10S2
N,N'-(1,4-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide)
—— (3Z)-5-Ethyl-3-[(2-hydroxyphenyl)methylidene]thiophen-2(3H)-one 60466-76-4 C13H12O2S
(3Z)-5-Ethyl-3-[(2-hydroxyphenyl)methylidene]thiophen-2(3H)-one
—— rubrolide N 287965-29-1 C17H9Br2ClO4
rubrolide N
—— 5-Ethyl-3-[1-(2-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-3H-thiophen-2-one 60466-78-6 C14H14O3S
5-Ethyl-3-[1-(2-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-3H-thiophen-2-one
—— (3Z)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-ethylthiophen-2-one 60466-77-5 C13H11ClO2S
(3Z)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-ethylthiophen-2-one
—— 5-fluoro-2-methoxy-4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenol 918524-34-2 C24H33FN2O2Si
5-fluoro-2-methoxy-4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenol
—— (S,S,S)-2-[(3,5-bis{[4-(3-hydroxyphenyl)-4,5-dihydrooxazol-2-yl]methyl}-2,4,6-triethyl)phenyl]methyl-4-(3-hydroxyphenyl)-4,5-dihydrooxazole 873783-15-4 C42H45N3O6
(S,S,S)-2-[(3,5-bis{[4-(3-hydroxyphenyl)-4,5-dihydrooxazol-2-yl]methyl}-2,4,6-triethyl)phenyl]methyl-4-(3-hydroxyphenyl)-4,5-dihydrooxazole
—— 3-(8-Pentadecenyl)-1,2-benzenediol 2764-91-2 C21H34O2
3-(8-Pentadecenyl)-1,2-benzenediol
—— 5-bromo-4-(1,3-dioxolan-2-yl)-2-methoxyphenol 472955-00-3 C10H11BrO4
5-bromo-4-(1,3-dioxolan-2-yl)-2-methoxyphenol
—— 4-fluoro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide 329053-69-2 C15H13FN2O3
4-fluoro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(5-methyl-3-oxopyrazolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181082-16-5 C14H12FN3O3S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(5-methyl-3-oxopyrazolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 2-(2-ethynyl-4,5-dimethoxyphenyl)ethanol 1239085-76-7 C12H14O3
2-(2-ethynyl-4,5-dimethoxyphenyl)ethanol
—— 4-(4-hydroxyphenyl)-2-methyl-2-trimethylsiloxybutane 958640-41-0 C14H24O2Si
4-(4-hydroxyphenyl)-2-methyl-2-trimethylsiloxybutane
—— 3-allyl-6-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde 479633-80-2 C12H13BrO3
3-allyl-6-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde
—— methyl 2-hydroxy-3,4-dimethoxyphenylacetate 369386-09-4 C11H14O5
methyl 2-hydroxy-3,4-dimethoxyphenylacetate
—— 4-(4-hydroxyphenyl)butan-2-aminium chloride 74432-61-4 C10H15NO*ClH
4-(4-hydroxyphenyl)butan-2-aminium chloride
—— 4-(3-amino-3-methylbutyl)phenol 83987-81-9 C11H17NO
4-(3-amino-3-methylbutyl)phenol
—— 1-({1-[3-(4-hydroxyphenyl)-1-methylpropyl]piperidin-4-yl}methyl)piperidin-4-ol 627052-30-6 C21H34N2O2
1-({1-[3-(4-hydroxyphenyl)-1-methylpropyl]piperidin-4-yl}methyl)piperidin-4-ol
—— 1,3-Benzenediol, 4-nitro-, sodium salt 63512-41-4 C6H4NNaO4
1,3-Benzenediol, 4-nitro-, sodium salt