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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
—— 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol 1134914-88-7 C15H12Cl2F3NO2
3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol
—— 5-(2-Heptadecenyl)-1,3-benzenediol 94751-34-5 C23H38O2
5-(2-Heptadecenyl)-1,3-benzenediol
—— 5-(12,15-Heneicosadienyl)-1,3-benzenediol 189562-03-6 C27H44O2
5-(12,15-Heneicosadienyl)-1,3-benzenediol
—— 5-hydroxy-2-methoxybenzamide 180526-91-4 C8H9NO3
5-hydroxy-2-methoxybenzamide
—— 5-(10,13-Nonadecadienyl)-1,3-benzenediol 189562-02-5 C25H40O2
5-(10,13-Nonadecadienyl)-1,3-benzenediol
—— (E)-4-methyl-2-(2-nitrovinyl)phenol 264224-82-0 C9H9NO3
(E)-4-methyl-2-(2-nitrovinyl)phenol
—— (E)-2-methoxy-6-(2-nitrovinyl)phenol 1986-06-7 C9H9NO4
(E)-2-methoxy-6-(2-nitrovinyl)phenol
—— (E)-5-methyl-2-(2-nitrovinyl)phenol 1221276-72-7 C9H9NO3
(E)-5-methyl-2-(2-nitrovinyl)phenol
—— Diisopropyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-N-methyl-N-(3-picolyl)-aminomethylphosphonate 187338-65-4 C22H33N2O5P
Diisopropyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-N-methyl-N-(3-picolyl)-aminomethylphosphonate
—— 2-methyl-5-(4-methylthiazol-2-ylamino)phenol 933045-63-7 C11H12N2OS
2-methyl-5-(4-methylthiazol-2-ylamino)phenol
—— diisopropyl 2-hydroxyphenylphosphonate 129529-31-3 C12H19O4P
diisopropyl 2-hydroxyphenylphosphonate
—— (S)-(+)-2-(4-hydroxyphenyl)propionic acid methylcarbonylmethyl ester 164210-45-1 C12H14O4
(S)-(+)-2-(4-hydroxyphenyl)propionic acid methylcarbonylmethyl ester
—— Feruperine 77795-15-4 C17H21NO3
Feruperine
—— 2-methoxy-5-(4-methylthiazol-2-ylamino)phenol 933045-64-8 C11H12N2O2S
2-methoxy-5-(4-methylthiazol-2-ylamino)phenol
—— (E)-4-[5-(4-Hydroxyphenoxy)-3-penten-1-ynyl]phenol 166762-98-7 C17H14O3
(E)-4-[5-(4-Hydroxyphenoxy)-3-penten-1-ynyl]phenol
—— Hispolone 173933-40-9 C12H12O4
Hispolone
—— tetraisopropyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxy-5-methoxyphenyl)-methylphosphonate] 1537890-13-3 C34H56N2O10P2
tetraisopropyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxy-5-methoxyphenyl)-methylphosphonate]
—— diisopropyl (R)-α-methylbenzylamino-(S)-(2-hydroxyphenyl)methylphosphonate 1537890-15-5 C21H30NO4P
diisopropyl (R)-α-methylbenzylamino-(S)-(2-hydroxyphenyl)methylphosphonate
—— tetraisopropyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxyphenyl)methylphosphonate] 1537890-09-7 C32H52N2O8P2
tetraisopropyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxyphenyl)methylphosphonate]
—— 6-hydroxy-2,3-dimethoxybenzaldehyde 65162-28-9 C9H10O4
6-hydroxy-2,3-dimethoxybenzaldehyde
—— 2,4-diamino-5-(2-methoxy-5-hydroxybenzyl)pyrimidine 397245-73-7 C12H14N4O2
2,4-diamino-5-(2-methoxy-5-hydroxybenzyl)pyrimidine
—— Demethoxyshogaol 153311-54-7 C16H22O2
Demethoxyshogaol
—— tert-butyl 4-fluoro-2-hydroxybenzylcarbamate 1292211-10-9 C12H16FNO3
tert-butyl 4-fluoro-2-hydroxybenzylcarbamate
—— (E)-2-(4-hydroxybenzylidene)hydrazine-1-carbothioamide 947527-72-2 C8H9N3OS
(E)-2-(4-hydroxybenzylidene)hydrazine-1-carbothioamide
—— 3-bromo-2-ethylphenol 1260022-84-1 C8H9BrO
3-bromo-2-ethylphenol
—— 4,6-dimethoxy-3-amino-1-hydroxybenzene 114109-54-5 C8H11NO3
4,6-dimethoxy-3-amino-1-hydroxybenzene
—— ethyl 2-[(E)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate 1489265-08-8 C15H17N3O4S
ethyl 2-[(E)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— (R)-2'-(cyclohept-2-enyl)-4'-methoxyphenol 200552-24-5 C14H18O2
(R)-2'-(cyclohept-2-enyl)-4'-methoxyphenol
—— ethyl 2-[(E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate 1489265-06-6 C15H17N3O4S
ethyl 2-[(E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— 1-(2-Hydroxy-4,6-dimethoxyphenyl)-2-propanone 205826-80-8 C11H14O4
1-(2-Hydroxy-4,6-dimethoxyphenyl)-2-propanone
—— 5-formyl-25,26,27,28-tetrahydroxycalix[4]arene 331985-38-7 C29H24O5
5-formyl-25,26,27,28-tetrahydroxycalix[4]arene
—— tetraformylcalixarene 266354-15-8 C32H24O8
tetraformylcalixarene
—— 2-(4-hydroxyphenyl)-2-trimethylsilyl-ethanol 418766-36-6 C11H18O2Si
2-(4-hydroxyphenyl)-2-trimethylsilyl-ethanol
—— 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,26-dihydroxycalix[4]arene-1,2-crown-4 189182-98-7 C50H66O6
5,11,17,23-tetrakis(1,1-dimethylethyl)-25,26-dihydroxycalix[4]arene-1,2-crown-4
—— Phenol, 2-(1,1,2,2-tetrafluoroethyl)- 1784324-57-7 C8H6F4O
Phenol, 2-(1,1,2,2-tetrafluoroethyl)-
—— 2,6-dimethyl-4-[(trimethylsilyl)methyloxy]phenol 139645-80-0 C12H20O2Si
2,6-dimethyl-4-[(trimethylsilyl)methyloxy]phenol
—— (+/-)-3-(2-chloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one 955407-19-9 C18H20ClN3O2
(+/-)-3-(2-chloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one
—— 2,3,5-trimethyl-4-nitrosophenol 83498-59-3 C9H11NO2
2,3,5-trimethyl-4-nitrosophenol
—— 3-Hydroxy-3-(2-hydroxy-5-methoxy-phenyl)-1,3-dihydro-indol-2-one 209847-88-1 C15H13NO4
3-Hydroxy-3-(2-hydroxy-5-methoxy-phenyl)-1,3-dihydro-indol-2-one
—— 3-octylbenzene-1,2-diol 21704-30-3 C14H22O2
3-octylbenzene-1,2-diol
—— 3-pentylcatechol 21704-29-0 C11H16O2
3-pentylcatechol
—— 3-Cyclohexylmethyl-brenzkatechin 16825-48-2 C13H18O2
3-Cyclohexylmethyl-brenzkatechin
—— 3-(2,3-dihydroxyphenyl)-1-(2-pyridyl)propan-1-ol 311804-78-1 C14H15NO3
3-(2,3-dihydroxyphenyl)-1-(2-pyridyl)propan-1-ol
—— 2-bromo-6-hydroxy-3-methoxybenzaldehyde 327163-78-0 C8H7BrO3
2-bromo-6-hydroxy-3-methoxybenzaldehyde
—— 4-methoxy-3,5-di-tert-butylphenol 24289-65-4 C15H24O2
4-methoxy-3,5-di-tert-butylphenol
—— (2-hydroxy-4-methoxy-phenyl)-glyoxylic acid 120240-70-2 C9H8O5
(2-hydroxy-4-methoxy-phenyl)-glyoxylic acid
—— 3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one 405313-50-0 C19H17NO5
3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
—— trans-4-chloro-3-hydroxy-5a,6,7,8,9,9a-hexahydrophenoxathiin 88062-59-3 C12H13ClO2S
trans-4-chloro-3-hydroxy-5a,6,7,8,9,9a-hexahydrophenoxathiin
—— 5-Ethyl-2-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenol 320589-76-2 C13H17NO
5-Ethyl-2-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenol
—— 4-(2-bromoethyl)-3,5-dimethylphenol 1020666-86-7 C10H13BrO
4-(2-bromoethyl)-3,5-dimethylphenol