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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
—— 4-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone 923267-63-4 C11H10O4S
4-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone
—— 3-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone 923267-62-3 C11H10O4S
3-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone
—— 3,4-bis[(2-furylmethyl)sulfanyl]hydroxyhydroquinone 923267-64-5 C16H14O5S2
3,4-bis[(2-furylmethyl)sulfanyl]hydroxyhydroquinone
—— 4-(nonyloxy)benzene-1,2-diol 263159-84-8 C15H24O3
4-(nonyloxy)benzene-1,2-diol
—— 4-(octyloxy)benzene-1,2-diol 59263-61-5 C14H22O3
4-(octyloxy)benzene-1,2-diol
—— 2,4-dimethoxyethoxymethyloxyphenol 312608-04-1 C14H22O7
2,4-dimethoxyethoxymethyloxyphenol
—— 3-chloro-4-(4-methoxybenzyloxy)phenethyl methanesulfonate 1147391-92-1 C17H19ClO5S
3-chloro-4-(4-methoxybenzyloxy)phenethyl methanesulfonate
—— 2-methoxy-6-methyl-4-[2-(thien-2-yl)ethenyl]phenol 127035-66-9 C14H14O2S
2-methoxy-6-methyl-4-[2-(thien-2-yl)ethenyl]phenol
—— 2-Brom-4-nitroso-phenol 15516-58-2 C6H4BrNO2
2-Brom-4-nitroso-phenol
—— 2,6-dimethoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol 127035-72-7 C14H14O3S
2,6-dimethoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 2-Ethyl-6-methoxy-4-(2-thiophen-2-yl-vinyl)-phenol 127035-67-0 C15H16O2S
2-Ethyl-6-methoxy-4-(2-thiophen-2-yl-vinyl)-phenol
—— 2,6-dimethyl-4-[2-(2-thienyl)ethyl]phenol 127035-96-5 C14H16OS
2,6-dimethyl-4-[2-(2-thienyl)ethyl]phenol
—— 4-[(2S,3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-3,4-dihydro-2H-pyran-6-yl]-2-bromophenol 143144-64-3 C24H41BrO4Si2
4-[(2S,3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-3,4-dihydro-2H-pyran-6-yl]-2-bromophenol
—— 2-chloro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol 127063-62-1 C13H11ClOS
2-chloro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 2-fluoro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol 127035-69-2 C13H11FOS
2-fluoro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 2-fluoro-6-methoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol 127035-71-6 C13H11FO2S
2-fluoro-6-methoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 4-hydroxy-2-methoxyphenylacetic acid 883988-36-1 C9H10O4
4-hydroxy-2-methoxyphenylacetic acid
—— 2-bromo-4-(3,4-dihydro-2H-pyran-6-yl)phenol 143144-61-0 C11H11BrO2
2-bromo-4-(3,4-dihydro-2H-pyran-6-yl)phenol
—— 3-Ethyl-5-methoxy-4-hydroxybenzaldehyde 125722-35-2 C10H12O3
3-Ethyl-5-methoxy-4-hydroxybenzaldehyde
—— 2-Allyl-6-methyl-4-(2-thiophen-2-yl-vinyl)-phenol 127035-70-5 C16H16OS
2-Allyl-6-methyl-4-(2-thiophen-2-yl-vinyl)-phenol
—— 4-(2-(dimethylamino)ethoxy)phenol 100238-29-7 C10H15NO2
4-(2-(dimethylamino)ethoxy)phenol
—— 2-trimethylsilyl-1,4-hydroquinone 15288-57-0 C9H14O2Si
2-trimethylsilyl-1,4-hydroquinone
—— 2-[(4-methoxyphenyl)methylideneamino]-5-nitrophenol 29644-87-9 C14H12N2O4
2-[(4-methoxyphenyl)methylideneamino]-5-nitrophenol
—— 2-bromo-4-tetrahydropyranyloxyphenol 201004-82-2 C11H13BrO3
2-bromo-4-tetrahydropyranyloxyphenol
—— 7-Bromo-5-hydroxy-1,3-benzothioxol-2-one 126190-09-8 C7H3BrO3S
7-Bromo-5-hydroxy-1,3-benzothioxol-2-one
—— (-)-isozonarol 250146-75-9 C21H30O2
(-)-isozonarol
—— (-)-ent-zonarol 39707-54-5 C21H30O2
(-)-ent-zonarol
—— 6-Bromo-5-hydroxy-1,3-benzothioxol-2-one 17835-34-6 C7H3BrO3S
6-Bromo-5-hydroxy-1,3-benzothioxol-2-one
—— 4-Bromo-5-hydroxy-1,3-benzothioxol-2-one 126190-10-1 C7H3BrO3S
4-Bromo-5-hydroxy-1,3-benzothioxol-2-one
—— 2-(4-Hydroxyphenyl)-4-(propan-2-yl)-2H-1,4-thiazin-3(4H)-one 87904-90-3 C13H15NO2S
2-(4-Hydroxyphenyl)-4-(propan-2-yl)-2H-1,4-thiazin-3(4H)-one
—— t-butyl N-[2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate 478375-22-3 C18H28BNO5
t-butyl N-[2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate
—— 2,3,5,6-tetrakis-ethylsulfanyl-hydroquinone 100964-28-1 C14H22O2S4
2,3,5,6-tetrakis-ethylsulfanyl-hydroquinone
—— 4-(1-bromoethyl)phenol 59771-02-7 C8H9BrO
4-(1-bromoethyl)phenol
—— (rac)-4-(1-hydroxyethyl)-2-chlorophenol 154639-01-7 C8H9ClO2
(rac)-4-(1-hydroxyethyl)-2-chlorophenol
—— 4-Butoxy-2,5-dimethyl-phenol 147351-63-1 C12H18O2
4-Butoxy-2,5-dimethyl-phenol
—— 2-amino-5-chloro-4-methoxyphenol 98280-37-6 C7H8ClNO2
2-amino-5-chloro-4-methoxyphenol
—— [5-(3-Hydroxy-4-methoxyphenyl)-2-sulfanylidene-1,3,4-thiadiazol-3-yl]-(4-hydroxyphenyl)methanone 1279084-94-4 C16H12N2O4S2
[5-(3-Hydroxy-4-methoxyphenyl)-2-sulfanylidene-1,3,4-thiadiazol-3-yl]-(4-hydroxyphenyl)methanone
—— 3-hydroxy-4-methoxybenzaldehyde 4-hydroxybenzoyl hydrazone 386284-11-3 C15H14N2O4
3-hydroxy-4-methoxybenzaldehyde 4-hydroxybenzoyl hydrazone
—— n-butyl, 3,4-dihydroxy-5-nitrophenylglyoxylate 125629-05-2 C12H13NO7
n-butyl, 3,4-dihydroxy-5-nitrophenylglyoxylate
—— dimethyl 4-hydroxy-2-methoxyphenyl phosphate 94420-80-1 C9H13O6P
dimethyl 4-hydroxy-2-methoxyphenyl phosphate
—— (2S)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one 1360617-34-0 C16H22O4
(2S)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one
—— 2,3a,4,5-Tetrahydro-6-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-3H-indazol-3-one 111570-61-7 C22H22N2O5
2,3a,4,5-Tetrahydro-6-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-3H-indazol-3-one
—— (2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one 1360617-33-9 C16H22O4
(2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one
—— 2-allyl-6-methoxybenzene-1,4-diol 31788-39-3 C10H12O3
2-allyl-6-methoxybenzene-1,4-diol
—— 3-Methoxy-4-methoxymethoxyphenol 104202-49-5 C9H12O4
3-Methoxy-4-methoxymethoxyphenol
—— 4-(1-aminoethyl)-2-methoxyphenol —— C9H13NO2
4-(1-aminoethyl)-2-methoxyphenol
—— 4-[(Butylamino)methyl]-2-methoxyphenol 112520-76-0 C12H19NO2
4-[(Butylamino)methyl]-2-methoxyphenol
—— 2-(3-hydroxy-4,4-dimethyl-1-oxido-5-phenyl-2H-imidazol-1-ium-2-yl)phenol 122981-44-6 C17H18N2O3
2-(3-hydroxy-4,4-dimethyl-1-oxido-5-phenyl-2H-imidazol-1-ium-2-yl)phenol
—— 7-methylbenzo[c][1,2]oxaborole-1,5(3H)-diol 1319804-01-7 C8H9BO3
7-methylbenzo[c][1,2]oxaborole-1,5(3H)-diol
—— (-)-(S)-5-bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxy-2-methoxybenzamide 107188-79-4 C15H21BrN2O3
(-)-(S)-5-bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxy-2-methoxybenzamide