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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-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole 1350923-22-6 C17H15FN2O4
3-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole
—— 4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide 386287-72-5 C15H13FN2O3
4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide
—— octahydro-4-(2-hydroxyphenyl)-3-methylcyclopent<e>-1,3-oxazin-2-one 75208-81-0 C14H17NO3
octahydro-4-(2-hydroxyphenyl)-3-methylcyclopent<e>-1,3-oxazin-2-one
—— 1,4-bis(2,3-dihydroxyphenyl)butane 175844-52-7 C16H18O4
1,4-bis(2,3-dihydroxyphenyl)butane
—— (S)-(+)-4-[1-(2-methyl)octyloxy]phenol 569353-66-8 C15H24O2
(S)-(+)-4-[1-(2-methyl)octyloxy]phenol
—— 4-(2-hydroxy-phenyl)-6-methyl-4,5-dihydro-2<i>H</i>-[1,2,4]triazin-3-one 62104-09-0 C10H11N3O2
4-(2-hydroxy-phenyl)-6-methyl-4,5-dihydro-2<i>H</i>-[1,2,4]triazin-3-one
—— 4-(3,5-difluoro-4-hydroxybenzyl)-1,2,4-triazole-3-thione 107186-80-1 C9H7F2N3OS
4-(3,5-difluoro-4-hydroxybenzyl)-1,2,4-triazole-3-thione
—— 4-(4-hydroxyphenyl)pentanoic acid 113194-60-8 C11H14O3
4-(4-hydroxyphenyl)pentanoic acid
—— 2-Hydroxy-5-methoxy-(2-cyclopentenyl)-benzol 61076-48-0 C12H14O2
2-Hydroxy-5-methoxy-(2-cyclopentenyl)-benzol
—— 2-cyclopropyl-3-methoxyphenol 499236-67-8 C10H12O2
2-cyclopropyl-3-methoxyphenol
—— N-<2-<<(4-methyl-5-imidazolyl)methyl>thio>ethyl>-4-hydroxybenzamidine 57785-50-9 C14H18N4OS
N-<2-<<(4-methyl-5-imidazolyl)methyl>thio>ethyl>-4-hydroxybenzamidine
—— Methyl 2-(2-hydroxy-5-nitrophenyl)-2-oxoacetate 82366-90-3 C9H7NO6
Methyl 2-(2-hydroxy-5-nitrophenyl)-2-oxoacetate
—— 3,5-dioctadecylpyrocatechol 74061-23-7 C42H78O2
3,5-dioctadecylpyrocatechol
—— 4-Chloro-2-cyclohex-2-en-1-ylphenol 151474-62-3 C12H13ClO
4-Chloro-2-cyclohex-2-en-1-ylphenol
—— 4-[3-(1-imidazolyl)-1-methylpropyl]-phenol 61292-85-1 C13H16N2O
4-[3-(1-imidazolyl)-1-methylpropyl]-phenol
—— 4-[5-(2-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzene-1,3-diol 1430092-66-2 C14H9FN2O2S
4-[5-(2-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzene-1,3-diol
—— Hydroxy-(2-hydroxy-3-methyl-phenyl)-acetic acid 73289-74-4 C9H10O4
Hydroxy-(2-hydroxy-3-methyl-phenyl)-acetic acid
—— N,N'-(1,1-dimethylethylene)bis(salicylaldimine) 30180-37-1 C18H20N2O2
N,N'-(1,1-dimethylethylene)bis(salicylaldimine)
—— 3,3'-((1E,1'E)-((2-methylpropane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(benzene-1,2-diol) 146559-05-9 C18H20N2O4
3,3'-((1E,1'E)-((2-methylpropane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(benzene-1,2-diol)
—— N,N’-bis(5-chlorosalicylidene)-2,2-dimethyl-1,3-diaminopropane 1268522-66-2 C18H18Cl2N2O2
N,N’-bis(5-chlorosalicylidene)-2,2-dimethyl-1,3-diaminopropane
—— methyl 2-hydroxy-5-methylbenzenecarbodithioate 116138-51-3 C9H10OS2
methyl 2-hydroxy-5-methylbenzenecarbodithioate
—— 4-(4-hydroxyphenoxy)-2-penten-1-ol 115778-33-1 C11H14O3
4-(4-hydroxyphenoxy)-2-penten-1-ol
—— 2(4-Hydroxyphenyl)imino-1,3-dithiolane 62850-53-7 C9H9NOS2
2(4-Hydroxyphenyl)imino-1,3-dithiolane
—— (E)-2-methoxy-4-(2-nitroprop-1-enyl)phenol 74273-16-8 C10H11NO4
(E)-2-methoxy-4-(2-nitroprop-1-enyl)phenol
—— (2-chloro-5-hydroxy-phenyl)acetic acid ethyl ester 928025-24-5 C10H11ClO3
(2-chloro-5-hydroxy-phenyl)acetic acid ethyl ester
—— N-<2-<<2-hydroxy-3-(3,4-dihydroxyphenoxy)propyl>amino>ethyl>-2-methylpropanamide 53672-71-2 C15H24N2O5
N-<2-<<2-hydroxy-3-(3,4-dihydroxyphenoxy)propyl>amino>ethyl>-2-methylpropanamide
—— 1-p-hydroxyphenyl-2-(β-isobutyramidoethyl)aminoethanol 56442-89-8 C14H22N2O3
1-p-hydroxyphenyl-2-(β-isobutyramidoethyl)aminoethanol
—— 4-[2-Hydroxy-3-(2-phenoxy-ethylamino)-propoxy]-phenol 64463-87-2 C17H21NO4
4-[2-Hydroxy-3-(2-phenoxy-ethylamino)-propoxy]-phenol
—— 2-[(Benzylsulfanyl)methyl]-4-methoxyphenol 60530-19-0 C15H16O2S
2-[(Benzylsulfanyl)methyl]-4-methoxyphenol
—— 3-[(1R,2R)-1-hydroxy-2-methylpent-4-enyl]-2-methoxyphenol 1265279-04-6 C13H18O3
3-[(1R,2R)-1-hydroxy-2-methylpent-4-enyl]-2-methoxyphenol
—— 5-Methoxy-2-[1-(propylamino)ethyl]phenol 1042523-97-6 C12H19NO2
5-Methoxy-2-[1-(propylamino)ethyl]phenol
—— 2-(2,2,2-Trichloro-1-hydroxyethyl)phenol 59648-33-8 C8H7Cl3O2
2-(2,2,2-Trichloro-1-hydroxyethyl)phenol
—— 3-(3-Hydroxyhex-5-enyl)-2-methoxyphenol 1265278-90-7 C13H18O3
3-(3-Hydroxyhex-5-enyl)-2-methoxyphenol
—— 2-[1-(Butylamino)ethyl]-5-methoxyphenol 1038259-02-7 C13H21NO2
2-[1-(Butylamino)ethyl]-5-methoxyphenol
—— 2-[1-(cyclohexylamino)ethyl]-5-methoxyphenol 1042613-83-1 C15H23NO2
2-[1-(cyclohexylamino)ethyl]-5-methoxyphenol
—— 5-Methoxy-2-[1-(propan-2-ylamino)ethyl]phenol 1038230-91-9 C12H19NO2
5-Methoxy-2-[1-(propan-2-ylamino)ethyl]phenol
—— 2-methoxy-3-[(1R)-1-phenylmethoxyhex-5-enyl]phenol 1265279-11-5 C20H24O3
2-methoxy-3-[(1R)-1-phenylmethoxyhex-5-enyl]phenol
—— 2-(2,2,2-trichloro-1-hydroxyethyl)-4-chlorophenol 72422-56-1 C8H6Cl4O2
2-(2,2,2-trichloro-1-hydroxyethyl)-4-chlorophenol
—— 4-chloro-2-methyl-5-nitro-phenol 19044-75-8 C7H6ClNO3
4-chloro-2-methyl-5-nitro-phenol
—— HOC6H4CHN(i-Pr) 13033-49-3 C10H13NO
HOC6H4CHN(i-Pr)
—— 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione 212755-08-3 C12H6ClF4N3O5
1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione
—— N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester 59834-03-6 C11H14N2O3
N'-[1-(4-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester
—— cylindrocyclophane B 141854-65-1 C38H58O7
cylindrocyclophane B
—— cyclindrocyclophane D 141854-67-3 C40H60O8
cyclindrocyclophane D
—— (-)-cylindrocyclophane A 126693-92-3 C36H56O6
(-)-cylindrocyclophane A
—— (2E,2'E)-N,N-[2,2'-disulfanediylbis(propane-3,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] 1071822-33-7 C24H28Br2N4O6S2
(2E,2'E)-N,N-[2,2'-disulfanediylbis(propane-3,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— 4-(2-hydroxy-4-methoxyphenyl)-1-phenylpentan-3-one 1607446-79-6 C18H20O3
4-(2-hydroxy-4-methoxyphenyl)-1-phenylpentan-3-one
—— 2-(3-hydroxyphenyl)thiazole 35582-13-9 C9H7NOS
2-(3-hydroxyphenyl)thiazole
—— 2-(2-Methylsulfonylethyl)phenol 56490-39-2 C9H12O3S
2-(2-Methylsulfonylethyl)phenol
—— (3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 172484-39-8 C26H26O8
(3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one