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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
—— 2,3,5,6-tetrabromo-4-nitrophenol 6161-55-3 C6HBr4NO3
2,3,5,6-tetrabromo-4-nitrophenol
—— methyl (3S)-3-(4-hydroxyphenyl)butanoate 128677-78-1 C11H14O3
methyl (3S)-3-(4-hydroxyphenyl)butanoate
—— methyl ester of 3-(4'-hydroxyphenyl)-n-butyric acid 6555-07-3 C11H14O3
methyl ester of 3-(4'-hydroxyphenyl)-n-butyric acid
—— methyl 1-(2-hydroxyphenyl)cyclopropanecarboxylate 936328-78-8 C11H12O3
methyl 1-(2-hydroxyphenyl)cyclopropanecarboxylate
—— biphenylene-1,4-diol 406707-40-2 C12H8O2
biphenylene-1,4-diol
—— NCI 369077 126935-00-0 C36H38N2O12
NCI 369077
—— N-<(3,5,6-trichloro-2-hydroxyphenyl)methyl>formamide 81440-71-3 C8H6Cl3NO2
N-<(3,5,6-trichloro-2-hydroxyphenyl)methyl>formamide
—— (E)-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile 71750-09-9 C10H9NO2
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile
—— 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol 223268-30-2 C16H19NO
2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol
—— 2-<(1S)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol 223269-01-0 C16H19NO
2-<(1S)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol
—— ethyl bis(2-hydroxy-5-methoxyphenyl)phosphinate 99725-84-5 C16H19O6P
ethyl bis(2-hydroxy-5-methoxyphenyl)phosphinate
—— 5,11,17,23-tetramethyl-31,32,33,34,35-pentahydroxycalix[5]arene 224621-12-9 C39H38O5
5,11,17,23-tetramethyl-31,32,33,34,35-pentahydroxycalix[5]arene
—— 5-(3,4,5-trihydroxyphenyl)valeric acid 1204316-11-9 C11H14O5
5-(3,4,5-trihydroxyphenyl)valeric acid
—— 8-(3-hydroxyphenyl)octanal 157888-43-2 C14H20O2
8-(3-hydroxyphenyl)octanal
—— Propan-2-yl 2-[(2-bromo-5-hydroxy-4-methoxy-3-methylphenyl)methyl]-6-hydroxy-4-methyl-3-oxopiperazine-1-carboxylate 310904-06-4 C18H25BrN2O6
Propan-2-yl 2-[(2-bromo-5-hydroxy-4-methoxy-3-methylphenyl)methyl]-6-hydroxy-4-methyl-3-oxopiperazine-1-carboxylate
—— (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione 310903-96-9 C14H15BrN2O4
(Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione
—— 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione 221146-79-8 C14H18N2O4
3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione
—— 3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione 221146-83-4 C14H17BrN2O4
3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione
—— 3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione 221146-87-8 C18H23BrN2O6
3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione
—— N'-[(2,4-dihydroxyphenyl)methylene]-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazone 331234-59-4 C15H16N4O3
N'-[(2,4-dihydroxyphenyl)methylene]-4,5,6,7-tetrahydro-1H-indazole-3-carbohydrazone
—— 3-(2-hydrohy-4-methoxyphenyl)propynoic acid 84993-56-6 C10H8O4
3-(2-hydrohy-4-methoxyphenyl)propynoic acid
—— cardanol 501-26-8 C21H34O
cardanol
—— 2,6-dibromo-4-(3-hydroxypropyl)phenol 38972-02-0 C9H10Br2O2
2,6-dibromo-4-(3-hydroxypropyl)phenol
—— calix[4]hydroquinone 125583-08-6 C28H24O8
calix[4]hydroquinone
—— 4-fluoro-2-(furan-3-yl)-6-methylphenol 1572185-31-9 C11H9FO2
4-fluoro-2-(furan-3-yl)-6-methylphenol
—— 2-bromo-4-fluoro-6-methylphenol 1572185-50-2 C7H6BrFO
2-bromo-4-fluoro-6-methylphenol
—— 2.3.4-Trihydroxy-1-butyl-benzol 14503-28-7 C10H14O3
2.3.4-Trihydroxy-1-butyl-benzol
—— 2-[2'-(O-hydroxyphenyl)ethyl]-3-BOC-thiazolidine 103182-43-0 C16H23NO3S
2-[2'-(O-hydroxyphenyl)ethyl]-3-BOC-thiazolidine
—— 2-Allyl-4-methoxy-6-isopropylphenol 150267-58-6 C13H18O2
2-Allyl-4-methoxy-6-isopropylphenol
—— <i>N</i>-(4-hydroxy-phenyl)-<i>S</i>-methyl-isothiourea 96157-10-7 C8H10N2OS
<i>N</i>-(4-hydroxy-phenyl)-<i>S</i>-methyl-isothiourea
—— 2-bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1431330-24-3 C12H16BBrO3
2-bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— p-(2,2-dichloro-1,3-dimethylcyclopropyl)phenol 52178-82-2 C11H12Cl2O
p-(2,2-dichloro-1,3-dimethylcyclopropyl)phenol
—— 3-(5-Phenyl-[1,3,4]thiadiazol-2-yl)phenol 163298-94-0 C14H10N2OS
3-(5-Phenyl-[1,3,4]thiadiazol-2-yl)phenol
—— 2,6-bis((4-(pyridin-2-yl)pyrimidin-2-ylthio)methyl)-4-methylphenol 944956-83-6 C27H22N6OS2
2,6-bis((4-(pyridin-2-yl)pyrimidin-2-ylthio)methyl)-4-methylphenol
—— 3-n-Pentyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion 93959-15-0 C15H17NO2S2
3-n-Pentyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion
—— 3-n-Hexyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion 93959-16-1 C16H19NO2S2
3-n-Hexyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion
—— 3.4.5-Trihydroxy-1-pentyl-benzol 858447-76-4 C11H16O3
3.4.5-Trihydroxy-1-pentyl-benzol
—— 4,12,16,24-tetrahydroxy-5,11,17,23-tetra-tert-butylcalix<4>arene 166986-54-5 C44H56O4
4,12,16,24-tetrahydroxy-5,11,17,23-tetra-tert-butylcalix<4>arene
—— 3-(3-hydroxyphenyl) butanal 81104-40-7 C10H12O2
3-(3-hydroxyphenyl) butanal
—— 5,12,20,27-Tetra-tert-butyl-8,15,23,30-tetrahydroxy<2.1.2.1>metacyclophane 125685-43-0 C46H60O4
5,12,20,27-Tetra-tert-butyl-8,15,23,30-tetrahydroxy<2.1.2.1>metacyclophane
—— N-[[3,5-bis[[(2-chloroacetyl)amino]methyl]-4-hydroxyphenyl]methyl]-2-chloroacetamide 1335416-29-9 C15H18Cl3N3O4
N-[[3,5-bis[[(2-chloroacetyl)amino]methyl]-4-hydroxyphenyl]methyl]-2-chloroacetamide
—— acetic acid 2-(3-hydroxyphenyl)ethyl ester 151287-95-5 C10H12O3
acetic acid 2-(3-hydroxyphenyl)ethyl ester
—— 5-methoxy-2-(morpholin-4-yl)methylphenol 340986-55-2 C12H17NO3
5-methoxy-2-(morpholin-4-yl)methylphenol
—— (4S)-2-isopropyl-4-(4-hydroxyphenylmethyl)-1,3-oxazolidine 1407180-48-6 C13H19NO2
(4S)-2-isopropyl-4-(4-hydroxyphenylmethyl)-1,3-oxazolidine
—— (S,E)-1-deuterio-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate 1360054-27-8 C13H14Cl3NO2
(S,E)-1-deuterio-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate
—— 2,2,2-trichloro-N-[5-(2-hydroxyphenyl)pent-1-en-3-yl]acetamide 1360054-14-3 C13H14Cl3NO2
2,2,2-trichloro-N-[5-(2-hydroxyphenyl)pent-1-en-3-yl]acetamide
—— (Z)-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate 1360054-13-2 C13H14Cl3NO2
(Z)-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate
—— (E)-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate 1360054-10-9 C13H14Cl3NO2
(E)-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate
—— 10-(2-hydroxyphenyl)-7-mesityl-10b-phenyl-10bH-11-oxa-4b1,10a-diaza-10bl4-boracyclopenta[e]aceanthrylen-10a-ium 1171817-76-7 C36H29BN2O2
10-(2-hydroxyphenyl)-7-mesityl-10b-phenyl-10bH-11-oxa-4b1,10a-diaza-10bl4-boracyclopenta[e]aceanthrylen-10a-ium
—— diethyl 11,17,23,35,41,47-hexa(tert-butyl)-49,50,51,52,53,54,55,56-octahydroxycalix[8]arene-5,29-dicarboxylate 211247-64-2 C86H104O12
diethyl 11,17,23,35,41,47-hexa(tert-butyl)-49,50,51,52,53,54,55,56-octahydroxycalix[8]arene-5,29-dicarboxylate