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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
—— 4-[2-(2,4-dihydroxy-phenyl)-6-hydroxy-4-methyl-3H-inden-1-yl]-thiophene-3-carbonitrile 1019985-37-5 C21H15NO3S
4-[2-(2,4-dihydroxy-phenyl)-6-hydroxy-4-methyl-3H-inden-1-yl]-thiophene-3-carbonitrile
—— 3-(2,5-dihydroxyphenyl)-3-hydroxy-4,7-dihydro-2-benzofuran-1-one 77425-78-6 C14H12O5
3-(2,5-dihydroxyphenyl)-3-hydroxy-4,7-dihydro-2-benzofuran-1-one
—— 3,5-Dinitro-benzoic acid [1-(4-hydroxy-3-methoxy-phenyl)-1-(4-nitro-phenylazo)-meth-(Z)-ylidene]-hydrazide 142274-54-2 C21H15N7O9
3,5-Dinitro-benzoic acid [1-(4-hydroxy-3-methoxy-phenyl)-1-(4-nitro-phenylazo)-meth-(Z)-ylidene]-hydrazide
—— thiomethylphenol 468055-59-6 C7H6OS
thiomethylphenol
—— hydroxymalonato-(2-dimethylaminomethyl-3-hydroxy-pyridine)platinum(II) 104380-70-3 C11H14N2O6Pt
hydroxymalonato-(2-dimethylaminomethyl-3-hydroxy-pyridine)platinum(II)
—— syn-11-((allyloxy)carbonyl)-3-(3-hydroxyphenyl)-1,6-methano<10>annulene 166804-08-6 C21H18O3
syn-11-((allyloxy)carbonyl)-3-(3-hydroxyphenyl)-1,6-methano<10>annulene
—— 1417183-03-9 C16H17NO3*ClH
—— 1-(2-(allyloxy)ethyl)-3-methoxybenzene 1616561-62-6 C12H16O2
1-(2-(allyloxy)ethyl)-3-methoxybenzene
—— Piperidine-1-carbothioic acid (2-hydroxy-5-nitro-phenyl)-amide 78720-34-0 C12H15N3O3S
Piperidine-1-carbothioic acid (2-hydroxy-5-nitro-phenyl)-amide
—— N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)thiophene-3-carboxamide 1334920-21-6 C15H12N2O3S2
N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)thiophene-3-carboxamide
—— (E)-ethyl 4-(6-bromo-3-hydroxy-2-methoxyphenyl)-2-methylbut-2-enoate 1443526-58-6 C14H17BrO4
(E)-ethyl 4-(6-bromo-3-hydroxy-2-methoxyphenyl)-2-methylbut-2-enoate
—— picric acid*3-cyanopyridine 126416-03-3 C6H3N3O7*C6H4N2
picric acid*3-cyanopyridine
—— 2,6-Dinitro-4-(1-methylnonyl)-phenol 17473-30-2 C16H24N2O5
2,6-Dinitro-4-(1-methylnonyl)-phenol
—— 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-benzene-1,2-diol 1199943-01-5 C12H8ClN3O2
4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-benzene-1,2-diol
—— 2,3,6-trimethyl-4-[(triisobutylsilyl)methylthio]phenol 1230389-03-3 C22H40OSSi
2,3,6-trimethyl-4-[(triisobutylsilyl)methylthio]phenol
—— 2,5-dipropyl-4-[2-(trimethylsilyl)ethyl]phenol 1230388-84-7 C17H30OSi
2,5-dipropyl-4-[2-(trimethylsilyl)ethyl]phenol
—— 410525-48-3 C27H21CeN3O12
—— 4-(4,6-bis-decyl-[1,3,5]triazin-2-yl)-benzene-1,3-diol 38358-58-6 C29H47N3O2
4-(4,6-bis-decyl-[1,3,5]triazin-2-yl)-benzene-1,3-diol
—— 1417158-16-7 C20H21N2O4*C28H20O16S4
—— Orcilaldehyd 4-propylthiosemicarbazon 21236-03-3 C12H17N3O2S
Orcilaldehyd 4-propylthiosemicarbazon
—— 4-[2-(2-Hydroxy-5-methyl-phenyl-ONN-azoxy)-phenylazo]-5-methyl-2-(4-nitro-phenyl)-2,4-dihydro-pyrazol-3-one 15175-32-3 C23H19N7O5
4-[2-(2-Hydroxy-5-methyl-phenyl-ONN-azoxy)-phenylazo]-5-methyl-2-(4-nitro-phenyl)-2,4-dihydro-pyrazol-3-one
—— 1-allyloxy-2-bromo-4-[2-(hexyloxy)ethyl]benzene 851438-28-3 C17H25BrO2
1-allyloxy-2-bromo-4-[2-(hexyloxy)ethyl]benzene
—— N-Butyryl-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin 17123-99-8 C11H13ClN2O2
N-Butyryl-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin
—— 2-chloro-6-iodo-4-methylphenol 1335094-09-1 C7H6ClIO
2-chloro-6-iodo-4-methylphenol
—— 4-(3-Bromo-4-hydroxy-phenyl)-butyramide 29112-52-5 C10H12BrNO2
4-(3-Bromo-4-hydroxy-phenyl)-butyramide
—— 2-(2,4-Dihydroxyphenyl)-2-hydroxyacetonitrile 909772-74-3 C8H7NO3
2-(2,4-Dihydroxyphenyl)-2-hydroxyacetonitrile
—— 4-hydroxyphenyl cation 37741-92-7 C6H5O
4-hydroxyphenyl cation
—— 6-Dimethylamino-2,4-bis-<2-hydroxy-4-methoxy-phenyl>-s-triazin 1248-65-3 C19H20N4O4
6-Dimethylamino-2,4-bis-<2-hydroxy-4-methoxy-phenyl>-s-triazin
—— N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]acetamide 59670-55-2 C10H12N2O3
N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]acetamide
—— dichloro-bis-(4-hydroxy-2-methyl-phenyl)-λ<sup>4</sup>-tellane 78083-61-1 C14H14Cl2O2Te
dichloro-bis-(4-hydroxy-2-methyl-phenyl)-λ<sup>4</sup>-tellane
—— 5,11,17-Trimethyl-23-[2-(25,26,27,28-tetrahydroxy-11,17,23-trimethyl-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)propan-2-yl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol 124028-40-6 C65H64O8
5,11,17-Trimethyl-23-[2-(25,26,27,28-tetrahydroxy-11,17,23-trimethyl-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)propan-2-yl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 2-(1H-Imidazol-4-YL)-ethanol, picrate 3945-02-6 C11H11N5O8
2-(1H-Imidazol-4-YL)-ethanol, picrate
—— 2,3-Dimethyl-4,6-dinitro-phenol; compound with morpholine 4192-53-4 C4H9NO*C8H8N2O5
2,3-Dimethyl-4,6-dinitro-phenol; compound with morpholine
—— piperazine; compound with resorcinol 706-57-0 C4H10N2*C6H6O2
piperazine; compound with resorcinol
—— N-(2-hydroxy-5-nitrobenzyl)-(S)-α-methylbenzylamine 857062-71-6 C15H16N2O3
N-(2-hydroxy-5-nitrobenzyl)-(S)-α-methylbenzylamine
—— 1370711-60-6 C19H23N3O2
—— 4-(2-amino-ethyl)-5-bromo-2-methoxy-phenol 112299-43-1 C9H12BrNO2
4-(2-amino-ethyl)-5-bromo-2-methoxy-phenol
—— 5-(2-Hydroxy-3-isopropylamino-propoxy)-benzene-1,3-diol 46834-27-9 C12H19NO4
5-(2-Hydroxy-3-isopropylamino-propoxy)-benzene-1,3-diol
—— 2-[2-[3-[2-[(2-Hydroxyphenyl)methylideneamino]ethylamino]propylamino]ethyliminomethyl]phenol 166891-80-1 C21H28N4O2
2-[2-[3-[2-[(2-Hydroxyphenyl)methylideneamino]ethylamino]propylamino]ethyliminomethyl]phenol
—— (+/-)-17-ethynyl-8,9:13,14-diseco-18-norestradiol 81423-35-0 C19H26O2
(+/-)-17-ethynyl-8,9:13,14-diseco-18-norestradiol
—— 5-Iodo-2-methoxy-3-methylphenol 351378-62-6 C8H9IO2
5-Iodo-2-methoxy-3-methylphenol
—— 5-fluoro-2,4-dimethyl-phenol 400-03-3 C8H9FO
5-fluoro-2,4-dimethyl-phenol
—— 1-<12-hydroxydodeca-5(Z),10(Z)-dienyl>-2,3,4,5-tetramethoxy-6-methylbenzene 80810-46-4 C23H36O5
1-<12-hydroxydodeca-5(Z),10(Z)-dienyl>-2,3,4,5-tetramethoxy-6-methylbenzene
—— 5-(2-cyclohexyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol 623559-99-9 C15H20O2S2
5-(2-cyclohexyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol
—— [2-(2-Acetyl-3,6-dihydroxy-5-methoxy-4-methyl-phenyl)-ethyl]-benzyl-carbamic acid benzyl ester 107302-01-2 C27H29NO6
[2-(2-Acetyl-3,6-dihydroxy-5-methoxy-4-methyl-phenyl)-ethyl]-benzyl-carbamic acid benzyl ester
—— (S)-4-hydroxyphenyllactoyl-N-acetylcysteamine 1443120-44-2 C13H17NO4S
(S)-4-hydroxyphenyllactoyl-N-acetylcysteamine
—— 2-benzo[1,3]dioxol-5-yl-N-(2-bromo-5-hydroxy-4-methoxy-phenethyl)-acetamide 34088-13-6 C18H18BrNO5
2-benzo[1,3]dioxol-5-yl-N-(2-bromo-5-hydroxy-4-methoxy-phenethyl)-acetamide
—— 1361118-00-4 C20H34O2Si2
—— 2-bromo-5-methyl-3,6-bis(prop-2-enylamino)benzene-1,4-diol 98217-15-3 C13H17BrN2O2
2-bromo-5-methyl-3,6-bis(prop-2-enylamino)benzene-1,4-diol
—— Acetic acid--2-ethynylphenol (1/1) 152753-82-7 C10H10O3
Acetic acid--2-ethynylphenol (1/1)