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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-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
—— 2-(2-hydroxyphenyl)ethyl pivalate 138488-63-8 C13H18O3
2-(2-hydroxyphenyl)ethyl pivalate
—— 4-(1,7-Dichloro-4-methylheptan-4-yl)-2-methylphenol 1191377-83-9 C15H22Cl2O
4-(1,7-Dichloro-4-methylheptan-4-yl)-2-methylphenol
—— 2,3-dimethyl-6-(hydroxymethyl)-4-methoxyphenol 141989-00-6 C10H14O3
2,3-dimethyl-6-(hydroxymethyl)-4-methoxyphenol
—— 6-(t-butyldimethylsilyloxy)methyl-2,3-dimethyl-4-methoxyphenol 141989-01-7 C16H28O3Si
6-(t-butyldimethylsilyloxy)methyl-2,3-dimethyl-4-methoxyphenol
—— (rac)-4-bromo-5-hydroxy[2.2]paracyclophane 958990-63-1 C16H15BrO
(rac)-4-bromo-5-hydroxy[2.2]paracyclophane
—— 5-Bromo-2-(oxan-2-yloxymethyl)phenol 1172626-68-4 C12H15BrO3
5-Bromo-2-(oxan-2-yloxymethyl)phenol
—— 5-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole 872726-48-2 C15H12FNO3S
5-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole
—— 5-fluoro-2-(4-hydroxy-3-methoxyphenyl)-benzothiazole 872726-43-7 C14H10FNO2S
5-fluoro-2-(4-hydroxy-3-methoxyphenyl)-benzothiazole
—— 4-(Pent-3-yn-1-yl)phenol 1449770-06-2 C11H12O
4-(Pent-3-yn-1-yl)phenol
—— 4-[4-(5-Tridecyl-4,5-dihydro-1,2-oxazol-3-yl)but-3-ynyl]phenol 1535990-61-4 C26H39NO2
4-[4-(5-Tridecyl-4,5-dihydro-1,2-oxazol-3-yl)but-3-ynyl]phenol
—— 3-(5'-methoxycarbonyl-2'-methyl-pent-2'-yl)-4-methoxyphenol 89644-72-4 C15H22O4
3-(5'-methoxycarbonyl-2'-methyl-pent-2'-yl)-4-methoxyphenol
—— Methyl 4-[(4,6-dimethoxy-2-hydroxy)benzyl]-1-piperazinecarbodithioate 125156-04-9 C15H22N2O3S2
Methyl 4-[(4,6-dimethoxy-2-hydroxy)benzyl]-1-piperazinecarbodithioate
—— 1-(3-Bromo-2-hydroxy-5-methylphenyl)-3-pyridin-4-ylprop-2-en-1-one 663620-30-2 C15H12BrNO2
1-(3-Bromo-2-hydroxy-5-methylphenyl)-3-pyridin-4-ylprop-2-en-1-one
—— (1R,2S)-2-(4-hydroxyphenyl)cyclopropanecarboxylic acid 1356600-36-6 C10H10O3
(1R,2S)-2-(4-hydroxyphenyl)cyclopropanecarboxylic acid
—— 3-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde 899822-71-0 C9H9BrO3
3-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde
—— 2-(hydroxymethyl)-3-nitrophenol 57356-31-7 C7H7NO4
2-(hydroxymethyl)-3-nitrophenol
—— 2-Tert-butylimino-5-(2-hydroxyphenyl)-1,3-thiazolidin-4-one 1628629-58-2 C13H16N2O2S
2-Tert-butylimino-5-(2-hydroxyphenyl)-1,3-thiazolidin-4-one
—— 15,31-dimethyl-3,11,19,27,33,35-hexaazapentacyclo[27.3.1.1.<sup>5,9</sup>1.<sup>21,25</sup>]-hexatriaconta-5,7,9(33),13,15,17(34),21,23,25(35),29,31,1(36)-dodecaene-34,36-diol 185675-92-7 C32H38N6O2
15,31-dimethyl-3,11,19,27,33,35-hexaazapentacyclo[27.3.1.1.<sup>5,9</sup>1.<sup>21,25</sup>]-hexatriaconta-5,7,9(33),13,15,17(34),21,23,25(35),29,31,1(36)-dodecaene-34,36-diol
—— (R)-2-(4'-carboxylphenyl)-3-(2'-hydroxy-5-methoxyphenyl)-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2-c]pyrimidin-4-ol 1620567-28-3 C24H21N3O5
(R)-2-(4'-carboxylphenyl)-3-(2'-hydroxy-5-methoxyphenyl)-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2-c]pyrimidin-4-ol
—— (1S,2'R)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate 1338384-85-2 C18H27NO8S
(1S,2'R)-1-(1'-Boc-2'-pyrrolidinyl)-2-(o,p-dihydroxyphenoxy)ethyl mesylate
—— (3-chloro-4-hydroxy-5-methylphenyl)acetic acid 920509-13-3 C9H9ClO3
(3-chloro-4-hydroxy-5-methylphenyl)acetic acid
—— [1-(3-hydroxy-5-methoxy-phenyl)-cyclohexa-2,5-dienyl]acetonitrile 868666-22-2 C15H15NO2
[1-(3-hydroxy-5-methoxy-phenyl)-cyclohexa-2,5-dienyl]acetonitrile
—— 4-propyloxypropylphenol 130601-72-8 C12H18O2
4-propyloxypropylphenol
—— 2-Hydroxy-3-methylbenzylphosphonsaeure 52741-95-4 C8H11O4P
2-Hydroxy-3-methylbenzylphosphonsaeure
—— 1-ketopyrrolizidine picrate 17390-07-7 C6H3N3O7*C7H11NO
1-ketopyrrolizidine picrate
—— p-(2,2-dichlorocyclopropylmethyl)phenol 52178-89-9 C10H10Cl2O
p-(2,2-dichlorocyclopropylmethyl)phenol
—— 4-Hydroxy-5-methoxy-2-n-propylbenzaldehyd 42044-79-1 C11H14O3
4-Hydroxy-5-methoxy-2-n-propylbenzaldehyd
—— 2-hydroxy-3-methoxy-5-propylbenzaldehyde 7452-11-1 C11H14O3
2-hydroxy-3-methoxy-5-propylbenzaldehyde
—— 3-Methoxy-5-methyl-2-phenylmethoxyphenol 852810-83-4 C15H16O3
3-Methoxy-5-methyl-2-phenylmethoxyphenol
—— 5-[[Tert-butyl(dimethyl)silyl]oxymethyl]-3-methoxy-2-phenylmethoxyphenol 852810-67-4 C21H30O4Si
5-[[Tert-butyl(dimethyl)silyl]oxymethyl]-3-methoxy-2-phenylmethoxyphenol