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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
—— tris(4-hydroxyphenyl)bismuth dichloride 214407-14-4 C18H15BiCl2O3
tris(4-hydroxyphenyl)bismuth dichloride
—— tris(3-hydroxyphenyl)bismuth dichloride 214407-13-3 C18H15BiCl2O3
tris(3-hydroxyphenyl)bismuth dichloride
—— tris(2-hydroxyphenyl)bismuth dichloride 214407-11-1 C18H15BiCl2O3
tris(2-hydroxyphenyl)bismuth dichloride
—— 2-(2-benzofuranyl)-2-(4-hydroxy-3-methoxyphenyl)-1-nitroethane 1079360-68-1 C17H15NO5
2-(2-benzofuranyl)-2-(4-hydroxy-3-methoxyphenyl)-1-nitroethane
—— Potassium guaiacolsulfonate 7134-11-4 C7H9KO6S
Potassium guaiacolsulfonate
—— Benzamide, 2-hydroxy-N-(1-methyl-1H-1,2,4-triazol-5-yl)-3-nitro- 1913000-00-6 C10H9N5O4
Benzamide, 2-hydroxy-N-(1-methyl-1H-1,2,4-triazol-5-yl)-3-nitro-
—— 5-(Aminomethyl)-2-fluorophenol hydrochloride 2044704-82-5 C7H9ClFNO
5-(Aminomethyl)-2-fluorophenol hydrochloride
—— 2-[4-(2-Hydroxyethyl)phenoxy]acetamide 173436-10-7 C10H13NO3
2-[4-(2-Hydroxyethyl)phenoxy]acetamide
—— I+/-,4-Dihydroxybenzenemethanesulfonic acid 732937-24-5 C7H8O5S
I+/-,4-Dihydroxybenzenemethanesulfonic acid
—— Ethyl 78-hydroxy-17,56-dioxaoctacyclo[61.2.2.27,10.213,16.231,34.239,42.257,60.12,6]octaheptaconta-1(65),2(78),3,5,7(77),8,10(76),13(75),14,16(74),31(73),32,34(72),39,41,57,59,63,66,68,70-henicosaen-11,29,35,37,43,61-hexayne-4-carboxylate 499138-73-7 C79H76O5
Ethyl 78-hydroxy-17,56-dioxaoctacyclo[61.2.2.27,10.213,16.231,34.239,42.257,60.12,6]octaheptaconta-1(65),2(78),3,5,7(77),8,10(76),13(75),14,16(74),31(73),32,34(72),39,41,57,59,63,66,68,70-henicosaen-11,29,35,37,43,61-hexayne-4-carboxylate
—— Azanium;2-methyl-3,5-dinitrophenol —— C7H10N3O5+
Azanium;2-methyl-3,5-dinitrophenol
—— 3-Bromo-4-(3,5-dibromo-2-hydroxyphenyl)pyrrole-2,5-dione 1364322-53-1 C10H4Br3NO3
3-Bromo-4-(3,5-dibromo-2-hydroxyphenyl)pyrrole-2,5-dione
—— 2-[(Z)-hex-2-enyl]phenol 1272609-91-2 C12H16O
2-[(Z)-hex-2-enyl]phenol
—— methyl 11-(4-hydroxy-3,5-dimethylphenyl)undecanoate 1015699-45-2 C20H32O3
methyl 11-(4-hydroxy-3,5-dimethylphenyl)undecanoate
—— 3-(2-chloro-4-hydroxyphenylethynyl)-2-methylcyclohex-2-enone 1037717-32-0 C15H13ClO2
3-(2-chloro-4-hydroxyphenylethynyl)-2-methylcyclohex-2-enone
—— N-[[4-hydroxy-3,5-bis[[8-(3-octyloxiran-2-yl)octanoylamino]methyl]phenyl]methyl]-8-(3-octyloxiran-2-yl)octanamide 1335416-41-5 C63H111N3O7
N-[[4-hydroxy-3,5-bis[[8-(3-octyloxiran-2-yl)octanoylamino]methyl]phenyl]methyl]-8-(3-octyloxiran-2-yl)octanamide
—— 1323355-85-6 C15H16NO2
—— 4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde 55525-45-6 C16H16O5
4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde
—— 4-Hydroxy-3-methoxy-2-methylsulfanylbenzonitrile 1245744-69-7 C9H9NO2S
4-Hydroxy-3-methoxy-2-methylsulfanylbenzonitrile
—— 24,30,36,41-Tetratert-butyl-45,46-dihydroxy-6,17-bis(2-hydroxyethyl)-3,20-dioxa-6,8,15,17-tetrazahexacyclo[20.15.7.128,32.139,43.02,34.021,26]hexatetraconta-1,21,23,25,28(46),29,31,34,36,39,41,43(45)-dodecaene-7,16-dione 1251829-60-3 C60H86N4O8
24,30,36,41-Tetratert-butyl-45,46-dihydroxy-6,17-bis(2-hydroxyethyl)-3,20-dioxa-6,8,15,17-tetrazahexacyclo[20.15.7.128,32.139,43.02,34.021,26]hexatetraconta-1,21,23,25,28(46),29,31,34,36,39,41,43(45)-dodecaene-7,16-dione
—— 2-[(2R)-2-hydroxypent-4-en-2-yl]phenol 904906-09-8 C11H14O2
2-[(2R)-2-hydroxypent-4-en-2-yl]phenol
—— prelunularic acid 85926-21-2 C15H16O5
prelunularic acid
—— 4,4'-decanediyl-di-pyrocatechol 102957-92-6 C22H30O4
4,4'-decanediyl-di-pyrocatechol
—— picric acid ; hydrazinium picrate 92694-76-3 C6H3N3O7*H4N2
picric acid ; hydrazinium picrate
—— N-[1-(4-hydroxy-2,3-dimethoxybenzyl)cyclohexyl]benzamide 1341190-87-1 C22H27NO4
N-[1-(4-hydroxy-2,3-dimethoxybenzyl)cyclohexyl]benzamide
—— Heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol 152266-41-6 C48H24O6
Heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol
—— 4-Methyl-2-(1,3-oxazolidin-3-ylmethyl)phenol 1206549-87-2 C11H15NO2
4-Methyl-2-(1,3-oxazolidin-3-ylmethyl)phenol
—— N<sup>8</sup>-(4-hydroxy-3,5-dimethoxycinnamoyl)spermidine 95686-91-2 C18H29N3O4
N<sup>8</sup>-(4-hydroxy-3,5-dimethoxycinnamoyl)spermidine
—— 2-chloro-4-methoxy-5-methylphenol 1600530-27-5 C8H9ClO2
2-chloro-4-methoxy-5-methylphenol
—— (Z)-5-(heptadec-2-en-1-yl)resorcinol 94751-34-5 C23H38O2
(Z)-5-(heptadec-2-en-1-yl)resorcinol
—— Imidazolium picrate 6011-29-6 C9H7N5O7
Imidazolium picrate
—— 1-(3-hydroxy-4-methoxyphenyl)-2-methylpropanol 1198054-48-6 C11H16O3
1-(3-hydroxy-4-methoxyphenyl)-2-methylpropanol
—— 2-[4-(4-tert-butylbenzyloxy)-phenyl]-ethanol 1228930-64-0 C19H24O2
2-[4-(4-tert-butylbenzyloxy)-phenyl]-ethanol
—— (1S,5S)-1-tert-butoxycarbonyl-7-(4-hydroxy-3-methoxyphenyl)-8-oxabicyclo[3.2.1]oct-6-en-2-one 1260495-45-1 C19H22O6
(1S,5S)-1-tert-butoxycarbonyl-7-(4-hydroxy-3-methoxyphenyl)-8-oxabicyclo[3.2.1]oct-6-en-2-one
—— 4-chloro-2-(phenylamino)phenol 1262620-83-6 C12H10ClNO
4-chloro-2-(phenylamino)phenol
—— (1S,5S,7S)-1-tert-butoxycarbonyl-7-(4-hydroxy-3-methoxyphenyl)-8-oxabicyclo[3.2.1]octan-2-one 1260495-48-4 C19H24O6
(1S,5S,7S)-1-tert-butoxycarbonyl-7-(4-hydroxy-3-methoxyphenyl)-8-oxabicyclo[3.2.1]octan-2-one
—— 3-(2-bromoethoxy)-4-methoxyphenol 1262778-72-2 C9H11BrO3
3-(2-bromoethoxy)-4-methoxyphenol
—— 4-[1-(Cyclopropylamino)ethyl]phenol hydrochloride 1258641-43-8 C11H16ClNO
4-[1-(Cyclopropylamino)ethyl]phenol hydrochloride
—— 2-Methoxy-5-{[(2-methylpropyl)amino]methyl}phenol hydrochloride 1240568-44-8 C12H20ClNO2
2-Methoxy-5-{[(2-methylpropyl)amino]methyl}phenol hydrochloride
—— plakortolide S 1267675-58-0 C24H36O5
plakortolide S
—— 10-chloro-2,8-dihydroxyphenothiabismine-5,5-dioxide 1273386-57-4 C12H8BiClO4S
10-chloro-2,8-dihydroxyphenothiabismine-5,5-dioxide
—— plakortolide N 1267674-78-1 C26H40O5
plakortolide N
—— plakortolide M 1267674-60-1 C26H40O5
plakortolide M
—— 1-[(2-hydroxyphenyl)methyl]-1-(oxolan-2-ylmethyl)-3-(1H-pyrazol-5-ylmethyl)urea 1223741-21-6 C17H22N4O3
1-[(2-hydroxyphenyl)methyl]-1-(oxolan-2-ylmethyl)-3-(1H-pyrazol-5-ylmethyl)urea
—— (4S)-2-(4-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid 1265908-22-2 C11H13NO4S
(4S)-2-(4-hydroxy-3-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
—— [3]-paradol 53172-01-3 C14H20O3
[3]-paradol
—— 3-Bromo-6-fluoro-2-methoxyphenol 1026796-50-8 C7H6BrFO2
3-Bromo-6-fluoro-2-methoxyphenol
—— 3-Bromo-5-fluoro-2-methoxyphenol 1026796-60-0 C7H6BrFO2
3-Bromo-5-fluoro-2-methoxyphenol
—— N-[2-(3-hydroxyphenyl)ethyl]-2-methoxyacetamide 1292285-61-0 C11H15NO3
N-[2-(3-hydroxyphenyl)ethyl]-2-methoxyacetamide
—— N-[2-(3-hydroxyphenyl)ethyl]methanesulfonamide 1292285-65-4 C9H13NO3S
N-[2-(3-hydroxyphenyl)ethyl]methanesulfonamide