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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-(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
—— mono ether of 5-n-butylresorcinol 88640-67-9 C11H16O2
mono ether of 5-n-butylresorcinol
—— 3-{[(1S,2S,4aS,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-decahydronaphthalen-1-yl]methyl}-5-methylphenol 1619982-91-0 C22H34O2
3-{[(1S,2S,4aS,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-decahydronaphthalen-1-yl]methyl}-5-methylphenol
—— (1S,2S,4aS,8aR)-1-[(3-hydroxy-5-methylphenyl)methyl]-5,5,8a-trimethyldecahydronaphthalene-2-carboxylic acid 1619982-93-2 C22H32O3
(1S,2S,4aS,8aR)-1-[(3-hydroxy-5-methylphenyl)methyl]-5,5,8a-trimethyldecahydronaphthalene-2-carboxylic acid
—— 2-hydroxy-benzaldehyde (4-oxo-5-phenyl-thiazolidin-2-ylidene)-hydrazone 97723-06-3 C16H13N3O2S
2-hydroxy-benzaldehyde (4-oxo-5-phenyl-thiazolidin-2-ylidene)-hydrazone
—— methyl 4-(3,4-dimethoxy-2-hydroxybenzyl)-1-piperazinecarbodithioate 125155-75-1 C15H22N2O3S2
methyl 4-(3,4-dimethoxy-2-hydroxybenzyl)-1-piperazinecarbodithioate
—— 3,5-Dihydroxyphenylphosphonic Acid 1307282-67-2 C6H7O5P
3,5-Dihydroxyphenylphosphonic Acid
—— β-resorcylaldazine 23452-50-8 C14H12N2O4
β-resorcylaldazine
—— 3-(2,5-dimethyl-3-thienyl)-4,4,5,5-tetrafluoro-2-(4-hydroxy-2,6-dimethylphenyl)cyclopent-2-enone 1607796-31-5 C19H16F4O2S
3-(2,5-dimethyl-3-thienyl)-4,4,5,5-tetrafluoro-2-(4-hydroxy-2,6-dimethylphenyl)cyclopent-2-enone
—— ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-(3'-hydroxy-5'-methoxyphenyl)-4H-chromene-3-carboxylate 1063714-33-9 C23H25NO7
ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-(3'-hydroxy-5'-methoxyphenyl)-4H-chromene-3-carboxylate
—— (S)-(+)-4-(1-Methylheptyl)phenol 103481-63-6 C14H22O
(S)-(+)-4-(1-Methylheptyl)phenol
—— (S)-(+)-2-(1-Methylheptyl)phenol 135628-86-3 C14H22O
(S)-(+)-2-(1-Methylheptyl)phenol
—— 3-{[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-5-methoxyphenol 1619984-00-7 C22H32O3
3-{[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-5-methoxyphenol
—— 2-(2-fluoro-5-hydroxyphenyl)acetic acid 149029-89-0 C8H7FO3
2-(2-fluoro-5-hydroxyphenyl)acetic acid
—— (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxy-4-methoxyphenyl)acetic acid 174146-47-5 C14H19NO7
(R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxy-4-methoxyphenyl)acetic acid
—— 2-(2-fluoro-3-hydroxyphenyl)acetic acid 1213229-25-4 C8H7FO3
2-(2-fluoro-3-hydroxyphenyl)acetic acid
—— 2-(3-hydroxy-2-methylphenyl)acetic acid 1261616-79-8 C9H10O3
2-(3-hydroxy-2-methylphenyl)acetic acid
—— 5-methoxy-3-<(8'Z,11'Z)-pentadeca-8',11',14'-trienyl>benzene-1,2,4-triol 105018-77-7 C22H32O4
5-methoxy-3-<(8'Z,11'Z)-pentadeca-8',11',14'-trienyl>benzene-1,2,4-triol
—— N,N'-Bis(t-butoxycarbonyl)-N"-3-(4-hydroxy-phenyl)propylguanidine 193282-98-3 C20H31N3O5
N,N'-Bis(t-butoxycarbonyl)-N"-3-(4-hydroxy-phenyl)propylguanidine
—— methyl 2-(3-nitro-4-hydroxyphenyl)propionate 65784-34-1 C10H11NO5
methyl 2-(3-nitro-4-hydroxyphenyl)propionate
—— 2,5-dichloro-3,6-dimethoxy-phenol 860442-08-6 C8H8Cl2O3
2,5-dichloro-3,6-dimethoxy-phenol