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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
—— N-(3,4-dihydroxybenzyl)-N'-hexylthiourea 383423-36-7 C14H22N2O2S
N-(3,4-dihydroxybenzyl)-N'-hexylthiourea
—— 5-methoxy-2-sorbylphenol 57309-79-2 C13H14O3
5-methoxy-2-sorbylphenol
—— 5,17-di-tert-butyl-11,23-diformylcalix[4]arene-25,26,27,28-tetrol 266340-39-0 C38H40O6
5,17-di-tert-butyl-11,23-diformylcalix[4]arene-25,26,27,28-tetrol
—— bis(3,4-dihydroxybenzyl)amine 633700-32-0 C14H15NO4
bis(3,4-dihydroxybenzyl)amine
—— 4,6-diallyl-benzene-1,3-diol 71449-74-6 C12H14O2
4,6-diallyl-benzene-1,3-diol
—— 2,5-Dibromtrifluorphenol 5510-39-4 C6HBr2F3O
2,5-Dibromtrifluorphenol
—— 2-(nitromethyl)-4-nitrophenol 36363-18-5 C7H6N2O5
2-(nitromethyl)-4-nitrophenol
—— 2-Nitro-2-(2-hydroxy-5-nitrophenyl)-propane-1,3-diol 36363-19-6 C9H10N2O7
2-Nitro-2-(2-hydroxy-5-nitrophenyl)-propane-1,3-diol
—— 4-(3,4-dicyano-2',5'-dihydroxyphenyl)butanoic acid 83575-15-9 C12H10N2O4
4-(3,4-dicyano-2',5'-dihydroxyphenyl)butanoic acid
—— 2,3-Dibromo-6-methoxyphenol 35488-16-5 C7H6Br2O2
2,3-Dibromo-6-methoxyphenol
—— 3,5-Diallyl-brenzcatechin 91496-10-5 C12H14O2
3,5-Diallyl-brenzcatechin
—— 2-(1,3-benzothiazol-2-ylsulfanyl)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide 128991-13-9 C17H15N3O3S2
2-(1,3-benzothiazol-2-ylsulfanyl)-N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-methyl-N-(3-picolyl)-amino]-ethylphosphonate 407583-85-1 C21H31N2O5P
diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-[N-methyl-N-(3-picolyl)-amino]-ethylphosphonate
—— Methyl-4-(2,5-dihydroxyphenyl)-butanoat 42604-30-8 C11H14O4
Methyl-4-(2,5-dihydroxyphenyl)-butanoat
—— N<sup>1</sup>-(4-oxo-2,5-cyclohexadien-1-ylidene)-N<sup>2</sup>-(4-hydroxyphenyl)-2,2,2-trifluoroethanimidamide 155447-65-7 C14H9F3N2O2
N<sup>1</sup>-(4-oxo-2,5-cyclohexadien-1-ylidene)-N<sup>2</sup>-(4-hydroxyphenyl)-2,2,2-trifluoroethanimidamide
—— 2-(5-(4,5-dibromo-1H-pyrrol-2-yl)isoxazol-3-yl)phenol 1443231-51-3 C13H8Br2N2O2
2-(5-(4,5-dibromo-1H-pyrrol-2-yl)isoxazol-3-yl)phenol
—— [(2-hydroxyphenyl)-ureidomethyl]-urea 6345-57-9 C9H12N4O3
[(2-hydroxyphenyl)-ureidomethyl]-urea
—— 1-(3-Hydroxyphenyl)-2-(3-pyridinyl)ethane 85666-11-1 C13H13NO
1-(3-Hydroxyphenyl)-2-(3-pyridinyl)ethane
—— 4-(1-hydroxy-2-(2-methoxyphenoxy)ethyl)-2,6-dimethoxyphenol 18167-89-0 C17H20O6
4-(1-hydroxy-2-(2-methoxyphenoxy)ethyl)-2,6-dimethoxyphenol
—— 2,6-Dibromo-4-(1,2,3-thiadiazol-4-yl)phenol 253586-54-8 C8H4Br2N2OS
2,6-Dibromo-4-(1,2,3-thiadiazol-4-yl)phenol
—— 2,5-Bis-<(benzyl-methyl-amino)-methyl>-hydrochinon 96668-33-6 C24H28N2O2
2,5-Bis-<(benzyl-methyl-amino)-methyl>-hydrochinon
—— 1-(3-hydroxyphenyl)-2,6-dimethyl-1H-pyridin-4-one hydrochloride 821789-67-7 C13H13NO2*ClH
1-(3-hydroxyphenyl)-2,6-dimethyl-1H-pyridin-4-one hydrochloride
—— 2-bromo-4-(3-hydroxy-3-methylbutyl)phenol 360578-04-7 C11H15BrO2
2-bromo-4-(3-hydroxy-3-methylbutyl)phenol
—— 1-Methylidene-6-(2'-hydroxyphenyl)methyl-5,5-dimethylcyclohex-2-ene 166523-58-6 C16H20O
1-Methylidene-6-(2'-hydroxyphenyl)methyl-5,5-dimethylcyclohex-2-ene
—— methyl 3-(3-bromo-5-chloro-4-hydroxyphenyl)Propionate 590417-22-4 C10H10BrClO3
methyl 3-(3-bromo-5-chloro-4-hydroxyphenyl)Propionate
—— 3-(3-bromo-4-hydroxyphenyl)-N-(2-sulfanylethyl)propanamide 1356929-98-0 C11H14BrNO2S
3-(3-bromo-4-hydroxyphenyl)-N-(2-sulfanylethyl)propanamide
—— 2,4,6-tris-morpholinomethyl-phloroglucinol 112689-24-4 C21H33N3O6
2,4,6-tris-morpholinomethyl-phloroglucinol
—— 3-(3-Pyridylmethyl)phenol 85633-33-6 C12H11NO
3-(3-Pyridylmethyl)phenol
—— 2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenol 859221-50-4 C16H22O
2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenol
—— (5-Chloro-2-hydroxy-benzyl)-phosphonamidic Acid Monoethyl Ester 713115-36-7 C9H13ClNO3P
(5-Chloro-2-hydroxy-benzyl)-phosphonamidic Acid Monoethyl Ester
—— Bicyclo[9.3.1]pentadeca-1(15),11,13-trien-15-ol 38660-82-1 C15H22O
Bicyclo[9.3.1]pentadeca-1(15),11,13-trien-15-ol
—— 6-allyl-2-iodophenol 54826-57-2 C9H9IO
6-allyl-2-iodophenol
—— 3-pentadeca-8,11-dienylphenol 31910-56-2 C21H32O
3-pentadeca-8,11-dienylphenol
—— 13-(2-hydroxyphenyl)-4-carboxy[2.2]paracyclophane 588717-77-5 C23H20O3
13-(2-hydroxyphenyl)-4-carboxy[2.2]paracyclophane
—— 4-hydroxymethyl-13-(2-hydroxyphenyl)-[2.2]paracyclopane 588717-78-6 C23H22O2
4-hydroxymethyl-13-(2-hydroxyphenyl)-[2.2]paracyclopane
—— 15-hydroxymethyl[2.2]paracyclophan-4-ol 600143-72-4 C17H18O2
15-hydroxymethyl[2.2]paracyclophan-4-ol
—— N-[2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide 1374640-38-6 C14H21NO3
N-[2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide
—— 2-dodecyl-4-chlorophenol 1115234-54-2 C18H29FO
2-dodecyl-4-chlorophenol
—— 1-[4-(2-Hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethan-1-one 5118-42-3 C13H13N3O4S
1-[4-(2-Hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethan-1-one
—— 4-[(2-hydroxy-5-nitrobenzylidene)amino]benzoic acid 184715-33-1 C14H10N2O5
4-[(2-hydroxy-5-nitrobenzylidene)amino]benzoic acid
—— 2-methoxy-5-<<(4-nitrophenyl)imino>methyl>phenol 115095-32-4 C14H12N2O4
2-methoxy-5-<<(4-nitrophenyl)imino>methyl>phenol
—— 4-Methyl-2-octyl-phenol 886-00-0 C15H24O
4-Methyl-2-octyl-phenol
—— 5-acetyl-4-(4-hydroxyphenyl)-2-carbamoyl-ethylsulfanyl-1,4-dihydropyridine-3-carbonitrile 5314-25-0 C17H17N3O3S
5-acetyl-4-(4-hydroxyphenyl)-2-carbamoyl-ethylsulfanyl-1,4-dihydropyridine-3-carbonitrile
—— Prop-2-en-1-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 5477-51-0 C16H18N2O5
Prop-2-en-1-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— N-<β-(4-Hydroxyphenylethyl>-1-adamantancarboxamid 42600-86-2 C19H25NO2
N-<β-(4-Hydroxyphenylethyl>-1-adamantancarboxamid
—— (5Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one 331711-38-7 C11H8BrNO3S2
(5Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 2-methyl-6-octylphenol 17901-33-6 C15H24O
2-methyl-6-octylphenol
—— 4-bromo-3-trimethylsilylphenol 17878-46-5 C9H13BrOSi
4-bromo-3-trimethylsilylphenol
—— methyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 5466-83-1 C14H15ClN2O5
methyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-Methyl-4-octyl-phenol 5075-81-0 C15H24O
2-Methyl-4-octyl-phenol