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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
—— N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide 391609-32-8 C17H19NO3
N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide
—— 2-chloro-3-methoxy-5-methylphenol 57074-22-3 C8H9ClO2
2-chloro-3-methoxy-5-methylphenol
—— tri(propan-2-yl)silyl N-[3-(4-hydroxy-3-methoxyphenyl)propyl]carbamate 391609-23-7 C20H35NO4Si
tri(propan-2-yl)silyl N-[3-(4-hydroxy-3-methoxyphenyl)propyl]carbamate
—— (1S,5S)-1-[2-(2-bromo-3-hydroxy-4-methoxyphenyl)ethyl]-2-[2-(4-methoxyphenoxy)ethyl]-6-oxabicyclo[3.2.1]oct-2-en-7-one 213390-20-6 C25H27BrO6
(1S,5S)-1-[2-(2-bromo-3-hydroxy-4-methoxyphenyl)ethyl]-2-[2-(4-methoxyphenoxy)ethyl]-6-oxabicyclo[3.2.1]oct-2-en-7-one
—— 2-Chloro-6-(2-hydroxyethyl)-4-methoxyphenol 359844-43-2 C9H11ClO3
2-Chloro-6-(2-hydroxyethyl)-4-methoxyphenol
—— [2-13C]-2-chloro-3-methoxy-5-methylphenol 426835-16-7 C8H9ClO2
[2-13C]-2-chloro-3-methoxy-5-methylphenol
—— isoplagiochin C 872607-47-1 C28H22O4
isoplagiochin C
—— 4,5-dimethoxy-2-[(E)-6-(4-nitrophenyl)hex-5-en-2-yl]phenol 143653-81-0 C20H23NO5
4,5-dimethoxy-2-[(E)-6-(4-nitrophenyl)hex-5-en-2-yl]phenol
—— 6-mercaptodopamine 72515-46-9 C8H11NO2S
6-mercaptodopamine
—— (R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one 135272-33-2 C19H30O4
(R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
—— 2'-hydroxy-4',6'-dimethoxy-ω-cinnamylidene acetophenone 223502-94-1 C19H18O4
2'-hydroxy-4',6'-dimethoxy-ω-cinnamylidene acetophenone
—— 4-hydroxybenzocyclobutene 145967-35-7 C8H6O
4-hydroxybenzocyclobutene
—— 6-(cyclohexylmethyl)-2-methoxyphenol 586963-56-6 C14H20O2
6-(cyclohexylmethyl)-2-methoxyphenol
—— Tert-butyl-[2-[4,5-dimethoxy-2-(3-methylbutoxy)-1,3-benzodithiol-7-yl]ethoxy]-diphenylsilane 149625-07-0 C32H42O4S2Si
Tert-butyl-[2-[4,5-dimethoxy-2-(3-methylbutoxy)-1,3-benzodithiol-7-yl]ethoxy]-diphenylsilane
—— N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine 149777-43-5 C23H29NO2
N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine
—— 2-tert-butyl-4-(2-methoxyethyl)phenol 206059-20-3 C13H20O2
2-tert-butyl-4-(2-methoxyethyl)phenol
—— 5-[(E)-4-(4-Dimethylamino-phenyl)-but-1-en-3-ynyl]-2-nitro-phenol 193957-49-2 C18H16N2O3
5-[(E)-4-(4-Dimethylamino-phenyl)-but-1-en-3-ynyl]-2-nitro-phenol
—— 15,35,55,75-Tetrakis(chloromethyl)-2,4,6,8-tetrathia-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,32,52,72-tetraol 244087-92-1 C28H20Cl4O4S4
15,35,55,75-Tetrakis(chloromethyl)-2,4,6,8-tetrathia-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,32,52,72-tetraol
—— 2-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-butane-1,4-diol 186411-99-4 C12H16O4
2-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-butane-1,4-diol
—— 2-[2,2-Difluoro-1-((E)-3-trimethylsilanyl-allyloxy)-vinyl]-phenol 1026388-95-3 C14H18F2O2Si
2-[2,2-Difluoro-1-((E)-3-trimethylsilanyl-allyloxy)-vinyl]-phenol
—— 1-bromo-4,5-dimethoxy-2-(2-tert-butyldimethylsiloxyethyl)benzene 406215-62-1 C16H27BrO3Si
1-bromo-4,5-dimethoxy-2-(2-tert-butyldimethylsiloxyethyl)benzene
—— 2-(2-Cyclohexen-1-yl)-3-hydroxy-4-methoxybenzaldehyde 176756-93-7 C14H16O3
2-(2-Cyclohexen-1-yl)-3-hydroxy-4-methoxybenzaldehyde
—— 3,4-dimethoxy-6-(2'-hydroxy)ethyl-2-methylphenol 359844-33-0 C11H16O4
3,4-dimethoxy-6-(2'-hydroxy)ethyl-2-methylphenol
—— Phenol, 3,5-bis[[bis(1,1-dimethylethyl)phosphino]methyl]-2,4,6-trimethyl- 194211-67-1 C27H50OP2
Phenol, 3,5-bis[[bis(1,1-dimethylethyl)phosphino]methyl]-2,4,6-trimethyl-
—— 4-Chloro-2-[1-hydroxy-2-(2-methyl-oxiranyl)-ethyl]-phenol 433955-11-4 C11H13ClO3
4-Chloro-2-[1-hydroxy-2-(2-methyl-oxiranyl)-ethyl]-phenol
—— 3-(3,4-dihydroxybenzyl)amino-1-propanesulfonic acid 720699-23-0 C10H15NO5S
3-(3,4-dihydroxybenzyl)amino-1-propanesulfonic acid
—— 1,1'-dichloro-5-(4-hydroxyphenyl)dipyrromethane 853073-92-4 C15H12Cl2N2O
1,1'-dichloro-5-(4-hydroxyphenyl)dipyrromethane
—— (2R,3R,4R)-3-[(1E,3E)-5-[3-chloro-5-(diethoxymethyl)-6-hydroxy-2-methoxy-4-methylphenyl]-3-methylpenta-1,3-dien-1-yl]-2,3,4-trimethylcyclohexan-1-one 748798-49-4 C28H41ClO5
(2R,3R,4R)-3-[(1E,3E)-5-[3-chloro-5-(diethoxymethyl)-6-hydroxy-2-methoxy-4-methylphenyl]-3-methylpenta-1,3-dien-1-yl]-2,3,4-trimethylcyclohexan-1-one
—— 1,2,4-Benzenetriol, chloro- 75562-91-3 C6H5ClO3
1,2,4-Benzenetriol, chloro-
—— Phenol, 4-[(acetyloxy)amino]-2-nitro- 374589-62-5 C8H8N2O5
Phenol, 4-[(acetyloxy)amino]-2-nitro-
—— Phenol, 4-[(acetyloxy)amino]-2,6-dinitro- 647021-95-2 C8H7N3O7
Phenol, 4-[(acetyloxy)amino]-2,6-dinitro-
—— 4-(Methoxymethoxy)-2,3-dimethyl-6-(trideuteriomethyl)phenol 816456-23-2 C11H16O3
4-(Methoxymethoxy)-2,3-dimethyl-6-(trideuteriomethyl)phenol
—— 2-tert-butyl-4-[(dimethyl-p-methoxylphenylsilyl)methyloxy]phenol 188579-03-5 C20H28O3Si
2-tert-butyl-4-[(dimethyl-p-methoxylphenylsilyl)methyloxy]phenol
—— ethyl (2E)-3-(3-bromo-5-hydroxy-4-methoxyphenyl)-2-phenylmethoxyiminopropanoate 511257-13-9 C19H20BrNO5
ethyl (2E)-3-(3-bromo-5-hydroxy-4-methoxyphenyl)-2-phenylmethoxyiminopropanoate
—— 3,4-dibenzyloxy-5-methylphenol 393803-50-4 C21H20O3
3,4-dibenzyloxy-5-methylphenol
—— 1-methoxy-6-(pent-2-enyl)phenol 483355-44-8 C12H16O2
1-methoxy-6-(pent-2-enyl)phenol
—— N-Chloracetyl-3,4-dihydroxy-phenaethylamin 17639-51-9 C10H12ClNO3
N-Chloracetyl-3,4-dihydroxy-phenaethylamin
—— 4-[(3-hydroxyphenyl)methyl]pyridine 782504-71-6 C12H11NO
4-[(3-hydroxyphenyl)methyl]pyridine
—— N-(2-hydroxy-6-nitro-phenyl)-N'-(3-trifluoromethyl-phenyl)urea 160383-87-9 C14H10F3N3O4
N-(2-hydroxy-6-nitro-phenyl)-N'-(3-trifluoromethyl-phenyl)urea
—— 3-(N,N-diethylaminomethyl)catechol 322648-98-6 C11H17NO2
3-(N,N-diethylaminomethyl)catechol
—— 3-Hydroxy-benzaldehyde O-benzyl-oxime 623914-45-4 C14H13NO2
3-Hydroxy-benzaldehyde O-benzyl-oxime
—— Phenol, 3-methoxy-5-[[5-(3-thienyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]- 858117-53-0 C19H16N2O2S
Phenol, 3-methoxy-5-[[5-(3-thienyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-
—— (1R,11S,13R)-7-Hydroxy-11-(3-hydroxy-propyl)-10,17-dioxa-tricyclo[11.3.1.0<sup>3,8</sup>]heptadeca-3(8),4,6-trien-9-one 857253-64-6 C18H24O5
(1R,11S,13R)-7-Hydroxy-11-(3-hydroxy-propyl)-10,17-dioxa-tricyclo[11.3.1.0<sup>3,8</sup>]heptadeca-3(8),4,6-trien-9-one
—— 4-(6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl)-phenol 835916-92-2 C17H13N5O
4-(6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl)-phenol
—— 2.6-Dihydroxy-3.5-dinitro-benzoesaeure 22604-82-6 C7H4N2O8
2.6-Dihydroxy-3.5-dinitro-benzoesaeure
—— 6-[(2S,3R,4S,5R,8S)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(1-ethoxyethoxy)-2,4,8-trimethylnonyl]-2,4-dimethoxy-3-methylphenol 717916-70-6 C37H72O7Si2
6-[(2S,3R,4S,5R,8S)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(1-ethoxyethoxy)-2,4,8-trimethylnonyl]-2,4-dimethoxy-3-methylphenol
—— 2-((3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxybutyl)-6-methoxyphenol 1027981-38-9 C17H30O4Si
2-((3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxybutyl)-6-methoxyphenol
—— 3-(1-Methylimidazolin-2-yl)phenol 194985-95-0 C10H12N2O
3-(1-Methylimidazolin-2-yl)phenol
—— (2S,3S,5S)-6-(6-benzyloxy-2-methoxymethoxy-3,5-dimethylhexyl)-3,4-dimethoxy-2-methylphenol 845536-37-0 C26H38O6
(2S,3S,5S)-6-(6-benzyloxy-2-methoxymethoxy-3,5-dimethylhexyl)-3,4-dimethoxy-2-methylphenol
—— tert-butyl N-[2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-[(4-bromo-3-hydroxy-5-methoxyphenyl)methyl]pyrimidin-4-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate 860771-62-6 C32H45BrN4O10
tert-butyl N-[2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-[(4-bromo-3-hydroxy-5-methoxyphenyl)methyl]pyrimidin-4-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate