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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
—— copper(II) 2,2'-((propane-1,3-diylbis(azaneylylidene))bis(ethan-1-yl-1-ylidene))diphenolate 21590-59-0 C19H20N2O2*Cu
copper(II) 2,2'-((propane-1,3-diylbis(azaneylylidene))bis(ethan-1-yl-1-ylidene))diphenolate
—— 2,6-bis(2,2-dimethylpropyl)phenol 81216-68-4 C16H26O
2,6-bis(2,2-dimethylpropyl)phenol
—— N-((1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)cyclopentyl)picolinamide 1427204-52-1 C27H28N4O5
N-((1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)cyclopentyl)picolinamide
—— 2-(2'-hydroxy-3'-bromo-5'-nitrophenyl)-5-tert-butyl-1,3-dithiane 152821-33-5 C14H18BrNO3S2
2-(2'-hydroxy-3'-bromo-5'-nitrophenyl)-5-tert-butyl-1,3-dithiane
—— 4-(3-isopropoxybutyl)phenol 1338831-52-9 C13H20O2
4-(3-isopropoxybutyl)phenol
—— 5,5'-bis-(4-hydroxy-phenyl)-3H,3'H-3,3'-piperazine-1,4-diyldimethyl-bis-[1,3,4]oxadiazol-2-one 81404-39-9 C22H22N6O6
5,5'-bis-(4-hydroxy-phenyl)-3H,3'H-3,3'-piperazine-1,4-diyldimethyl-bis-[1,3,4]oxadiazol-2-one
—— 4-{[1-(5-Chloro-2-hydroxy-3-nitro-phenyl)-meth-(E)-ylidene]-amino}-benzamide 41077-08-1 C14H10ClN3O4
4-{[1-(5-Chloro-2-hydroxy-3-nitro-phenyl)-meth-(E)-ylidene]-amino}-benzamide
—— 2-(1-Hydroxy-hex-5-enyl)-6-methoxy-phenol 371195-69-6 C13H18O3
2-(1-Hydroxy-hex-5-enyl)-6-methoxy-phenol
—— 2-bromo-4-fluoro-6-iodophenol 1335094-10-4 C6H3BrFIO
2-bromo-4-fluoro-6-iodophenol
—— (2-Hydroxy-phenyl)-phosphonic acid di-sec-butyl ester 129529-33-5 C14H23O4P
(2-Hydroxy-phenyl)-phosphonic acid di-sec-butyl ester
—— 1310496-21-9 Br*C27H39N2O4
—— (R)-2-(4-ethyl-4,5-dihydrooxazol-2-yl)phenol 850494-79-0 C11H13NO2
(R)-2-(4-ethyl-4,5-dihydrooxazol-2-yl)phenol
—— N,N'-bis-(3-Br-5Cl-salicylidene)-1,2-diimino-2-methylethane 518045-37-9 C17H14Br2Cl2N2O2
N,N'-bis-(3-Br-5Cl-salicylidene)-1,2-diimino-2-methylethane
—— 2-chloro-6-[(3-hydroxy-4-methoxybenzyl)amino]-9-isopropyl-8-azapurine 864269-43-2 C15H17ClN6O2
2-chloro-6-[(3-hydroxy-4-methoxybenzyl)amino]-9-isopropyl-8-azapurine
—— Tridodecylresorcin 52066-81-6 C42H78O2
Tridodecylresorcin
—— 2,5-bis[(4-hydroxyphenyl)(hydroxy)methyl]thiophene 867252-60-6 C18H16O4S
2,5-bis[(4-hydroxyphenyl)(hydroxy)methyl]thiophene
—— 4-chloro-N'-(2,6-dihydroxybenzylidene)-1H-pyrrole-2-carbohydrazide 1254110-99-0 C12H10ClN3O3
4-chloro-N'-(2,6-dihydroxybenzylidene)-1H-pyrrole-2-carbohydrazide
—— cis-2-methyl-6-phenyl-4-((triethylsilyl)oxy)-5,6-dihydro-2H-pyran 94110-22-2 C18H28O3Si
cis-2-methyl-6-phenyl-4-((triethylsilyl)oxy)-5,6-dihydro-2H-pyran
—— 2-chloro-1-(3-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 1082036-81-4 C18H17ClN2O3
2-chloro-1-(3-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
—— 82202-48-0 C12H10Cl2N2O
—— butyl 3-(3,5-dibromo-4-hydroxyphenyl)-1H-1,2,4-triazole-5-carboxylate 1191245-08-5 C13H13Br2N3O3
butyl 3-(3,5-dibromo-4-hydroxyphenyl)-1H-1,2,4-triazole-5-carboxylate
—— 5'-Methoxy-2'-hydroxy-4-stilbazoliummethoiodid 58729-46-7 C15H16NO2*I
5'-Methoxy-2'-hydroxy-4-stilbazoliummethoiodid
—— 4,4a,5,6,7,8-Hexahydro-4-(2-hydroxyphenyl)-1,8-dimethyl-2(3H)-naphthalinon 104022-75-5 C18H22O2
4,4a,5,6,7,8-Hexahydro-4-(2-hydroxyphenyl)-1,8-dimethyl-2(3H)-naphthalinon
—— 5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-[5-nitro-1,3-phenylenebis(methyleneoxy)]calix[6]arene 1052645-04-1 C74H89NO8
5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-[5-nitro-1,3-phenylenebis(methyleneoxy)]calix[6]arene
—— 1204604-00-1 C22H26N4O6
—— N-(2-hydroxy-5-nitrobenzyl)-aza-15-crown-5 79566-00-0 C17H26N2O7
N-(2-hydroxy-5-nitrobenzyl)-aza-15-crown-5
—— 3-(2-Hydroxy-5-nitro-phenyl)-5-phenyl-cyclohex-2-enone 40189-01-3 C18H15NO4
3-(2-Hydroxy-5-nitro-phenyl)-5-phenyl-cyclohex-2-enone
—— β-Orcilaldehyd 4-allylthiosemicarbazon 19861-13-3 C13H17N3O2S
β-Orcilaldehyd 4-allylthiosemicarbazon
—— (Z)-4-(4-Hydroxy-3,5-dimethyl-phenyl)-4-oxo-but-2-enoic acid butyl ester 52246-08-9 C16H20O4
(Z)-4-(4-Hydroxy-3,5-dimethyl-phenyl)-4-oxo-but-2-enoic acid butyl ester
—— 2,4,6-Trinitro-benzenesulfonic acid (E)-2-(3-benzenesulfonyl-phenylsulfanyl)-1,2-diphenyl-vinyl ester 35181-72-7 C32H21N3O11S3
2,4,6-Trinitro-benzenesulfonic acid (E)-2-(3-benzenesulfonyl-phenylsulfanyl)-1,2-diphenyl-vinyl ester
—— 2-Allyl-6-methyl-3-nitro-phenol 124317-02-8 C10H11NO3
2-Allyl-6-methyl-3-nitro-phenol
—— 3-hydroxy-<i>N</i>-methyl-mandelamidine 103501-64-0 C9H12N2O2
3-hydroxy-<i>N</i>-methyl-mandelamidine
—— ethyl 6-(2-hydroxy-3,4,6-trimethylphenyl)hexanoate 84978-25-6 C17H26O3
ethyl 6-(2-hydroxy-3,4,6-trimethylphenyl)hexanoate
—— Phenol, 2-(1-amino-2-cyclopropylethyl)-4-fluoro-3-methyl- 1270539-36-0 C12H16FNO
Phenol, 2-(1-amino-2-cyclopropylethyl)-4-fluoro-3-methyl-
—— 3-Methoxyphenyl-2-piperidylcarbinol*HCl 32511-71-0 C13H19NO3*ClH
3-Methoxyphenyl-2-piperidylcarbinol*HCl
—— 2,6-bis[[2-hydroxy-(1,1-dimethylethyl)imino]methyl]-4-methylphenol 1245798-02-0 C17H26N2O3
2,6-bis[[2-hydroxy-(1,1-dimethylethyl)imino]methyl]-4-methylphenol
—— 2-(3-hydroxy-benzylidene)-6H-imidazo[2,1-b]thiazole-3,5-dione 57518-51-1 C12H8N2O3S
2-(3-hydroxy-benzylidene)-6H-imidazo[2,1-b]thiazole-3,5-dione
—— 2-[(Z)-2-chloro-2-nitroethenyl]-5-methoxyphenol 117672-22-7 C9H8ClNO4
2-[(Z)-2-chloro-2-nitroethenyl]-5-methoxyphenol
—— 1-Acetoxy-2-<2-methoxy-phenoxy>-3-acetyl-mercapto-3-<3-methoxy-4-hydroxy-phenyl>-propan 5155-58-8 C21H24O7S
1-Acetoxy-2-<2-methoxy-phenoxy>-3-acetyl-mercapto-3-<3-methoxy-4-hydroxy-phenyl>-propan
—— 3-isopropylphenyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate 1193988-34-9 C24H30N2O5
3-isopropylphenyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate
—— 3-(3-fluoro-4-hydroxy-phenyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104633-67-1 C14H13FO2
3-(3-fluoro-4-hydroxy-phenyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— 11,23-Dimethyl-3,7,15,19-tetrazatricyclo[19.3.1.19,13]hexacosa-1(24),2,7,9,11,13(26),14,19,21(25),22-decaene-25,26-diol 750595-21-2 C24H28N4O2
11,23-Dimethyl-3,7,15,19-tetrazatricyclo[19.3.1.19,13]hexacosa-1(24),2,7,9,11,13(26),14,19,21(25),22-decaene-25,26-diol
—— 2-Cyclohexyl-5-methyl-4-nitroso-phenol 59334-10-0 C13H17NO2
2-Cyclohexyl-5-methyl-4-nitroso-phenol
—— 4-Chloro-2-nitro-6-{1-[(Z)-m-tolylimino]-ethyl}-phenol 112932-68-0 C15H13ClN2O3
4-Chloro-2-nitro-6-{1-[(Z)-m-tolylimino]-ethyl}-phenol
—— 5-(5-chloro-2,4-dihydroxyphenyl)-N-(7-(hydroxyl-amino)-7-oxoheptyl)-4-(4-methoxyphenyl)isoxazole-3-carboxamide 1012056-28-8 C24H26ClN3O7
5-(5-chloro-2,4-dihydroxyphenyl)-N-(7-(hydroxyl-amino)-7-oxoheptyl)-4-(4-methoxyphenyl)isoxazole-3-carboxamide
—— 2-Fluor-3-(3,4-dihydroxy-phenyl)-propionamid 22179-96-0 C9H10FNO3
2-Fluor-3-(3,4-dihydroxy-phenyl)-propionamid
—— 3-(4-hydroxybenzyl)-5-phenyl-4,5-dihydroisoxazole 1158558-27-0 C16H15NO2
3-(4-hydroxybenzyl)-5-phenyl-4,5-dihydroisoxazole
—— 4-(2-(dodecyloxy)ethyl)-phenol 1327337-47-2 C20H34O2
4-(2-(dodecyloxy)ethyl)-phenol
—— 51084-69-6 C11H12Br2N4O2S
—— 2-hydroxy-5-methylbenzaldehyde O-benzyl oxime 1068143-80-5 C15H15NO2
2-hydroxy-5-methylbenzaldehyde O-benzyl oxime