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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
—— 3,4-bis(4-hydroxy-3-methylphenyl)thiophene 1361305-91-0 C18H16O2S
3,4-bis(4-hydroxy-3-methylphenyl)thiophene
—— 3,4-bis(4-hydroxyphenyl)thiophene 97595-22-7 C16H12O2S
3,4-bis(4-hydroxyphenyl)thiophene
—— 2-methoxy-6-methylthiomethylphenol 18738-36-8 C9H12O2S
2-methoxy-6-methylthiomethylphenol
—— 2-methyl-6-methylthiomethylphenol 4526-40-3 C9H12OS
2-methyl-6-methylthiomethylphenol
—— tert-butyl 2-hydroxybenzyl(propyl)carbamate 1268163-66-1 C15H23NO3
tert-butyl 2-hydroxybenzyl(propyl)carbamate
—— 5-({[tert-Butyl(diphenyl)silyl]oxy}methyl)benzene-1,3-diol 192313-73-8 C23H26O3Si
5-({[tert-Butyl(diphenyl)silyl]oxy}methyl)benzene-1,3-diol
—— (Z)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pent-1-en-1-yl)benzene-1,2-diol 1612146-69-6 C21H29N3O2S
(Z)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pent-1-en-1-yl)benzene-1,2-diol
—— 5-(azidomethyl)benzene-1,3-diol 908118-10-5 C7H7N3O2
5-(azidomethyl)benzene-1,3-diol
—— 1-(4'-hydroxy-3'-methoxyphenyl)-1,3-dihydroisobenzofuran-5,7-diol 1035080-17-1 C15H14O5
1-(4'-hydroxy-3'-methoxyphenyl)-1,3-dihydroisobenzofuran-5,7-diol
—— 4,4'-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,2-diol 1443299-30-6 C18H16O4
4,4'-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,2-diol
—— 1,2-bis(3,5-dihydroxyphenyl)acetylene 400608-33-5 C14H10O4
1,2-bis(3,5-dihydroxyphenyl)acetylene
—— 2-Methoxy-5-[[[3-(4-methyl-1-piperazinyl)propyl]amino]methyl]phenol 1042528-00-6 C16H27N3O2
2-Methoxy-5-[[[3-(4-methyl-1-piperazinyl)propyl]amino]methyl]phenol
—— 5-[[3,5-Bis(phenylmethoxy)phenyl]methoxy]-3-tert-butyl-2-hydroxybenzaldehyde 360784-97-0 C32H32O5
5-[[3,5-Bis(phenylmethoxy)phenyl]methoxy]-3-tert-butyl-2-hydroxybenzaldehyde
—— 2-methoxy-6-(1-nitrohexan-2-yl)phenol 1393820-51-3 C13H19NO4
2-methoxy-6-(1-nitrohexan-2-yl)phenol
—— tert-Butyl (3R)-3-[(3-hydroxy-4-methoxybenzoyl)(isopropyl)amino]piperidine-1-carboxylate 1044562-04-0 C21H32N2O5
tert-Butyl (3R)-3-[(3-hydroxy-4-methoxybenzoyl)(isopropyl)amino]piperidine-1-carboxylate
—— 2-(1-cyclohexyl-2-nitroethyl)-6-methoxyphenol 1393820-55-7 C15H21NO4
2-(1-cyclohexyl-2-nitroethyl)-6-methoxyphenol
—— 2-methoxy-6-(3-methyl-1-nitrobutan-2-yl)phenol 1393820-54-6 C12H17NO4
2-methoxy-6-(3-methyl-1-nitrobutan-2-yl)phenol
—— (S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 790703-59-2 C12H13FN2O4
(S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
—— 2,8,14,20-Tetramethyl-2,8,14,20,25,26,27-heptazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaen-28-ol 1169706-64-2 C25H25N7O
2,8,14,20-Tetramethyl-2,8,14,20,25,26,27-heptazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaen-28-ol
—— 2,7-dimethyl-1,8-biphenylenediol 98991-01-6 C14H12O2
2,7-dimethyl-1,8-biphenylenediol
—— 2-bromo-5-hydroxy-3-methylbenzyl alcohol 173381-65-2 C8H9BrO2
2-bromo-5-hydroxy-3-methylbenzyl alcohol
—— 4-Acetyl-4-(3-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran 179420-72-5 C13H15FO3
4-Acetyl-4-(3-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran
—— 4-bromo-5-((2-ethylhexyl)oxy)-2-hydroxybenzaldehyde 1618092-95-7 C15H21BrO3
4-bromo-5-((2-ethylhexyl)oxy)-2-hydroxybenzaldehyde
—— 5-bromo-2-(5,5-dimethyl-1,3-dioxan-2-yl)-4-((2-ethylhexyl)oxy)phenol 1618092-96-8 C20H31BrO4
5-bromo-2-(5,5-dimethyl-1,3-dioxan-2-yl)-4-((2-ethylhexyl)oxy)phenol
—— 4-(1-hydroxyethyl)-4-(3-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran 179420-71-4 C13H17FO3
4-(1-hydroxyethyl)-4-(3-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran
—— 4-hydroxy-2-(1-methylheptyl)phenol 155758-80-8 C14H22O2
4-hydroxy-2-(1-methylheptyl)phenol
—— 4-(1-ethoxyethoxy)-(4-hydroxyphenyl)-2-butyn-1-ol 118741-59-6 C14H18O4
4-(1-ethoxyethoxy)-(4-hydroxyphenyl)-2-butyn-1-ol
—— 4-Hydroxy-2-methyl-3-nitrobenzene-1-sulfonic acid 62351-46-6 C7H7NO6S
4-Hydroxy-2-methyl-3-nitrobenzene-1-sulfonic acid
—— 4-(3-fluoro-5-hydroxyphenyl)-4-methylsulfinyl-3,4,5,6-tetrahydro-2H-pyran 167758-68-1 C12H15FO3S
4-(3-fluoro-5-hydroxyphenyl)-4-methylsulfinyl-3,4,5,6-tetrahydro-2H-pyran
—— 4-(3-hydroxyphenyl)-4-ethyl-3,4,5,6-tetrahydro-2H-pyran 139368-26-6 C13H18O2
4-(3-hydroxyphenyl)-4-ethyl-3,4,5,6-tetrahydro-2H-pyran
—— 4-(3-hydroxyphenyl)-4-(ethoxycarbonyl)-3,4,5,6-tetrahydro-2H-pyran 139368-06-2 C14H18O4
4-(3-hydroxyphenyl)-4-(ethoxycarbonyl)-3,4,5,6-tetrahydro-2H-pyran
—— 4-(3-hydroxyphenyl)-4-(carboxymethyl)-3,4,5,6-tetrahydro-2H-pyran 139368-20-0 C13H16O3
4-(3-hydroxyphenyl)-4-(carboxymethyl)-3,4,5,6-tetrahydro-2H-pyran
—— 4-(3-hydroxy-5-fluorophenyl)-4-methylthio-3,4,5,6-tetrahydro-2H-pyran 139368-13-1 C12H15FO2S
4-(3-hydroxy-5-fluorophenyl)-4-methylthio-3,4,5,6-tetrahydro-2H-pyran
—— 4-(3-hydroxyphenyl)-4-(1-hydroxyethyl)-3,4,5,6-tetrahydro-2H-pyran 139368-16-4 C13H18O3
4-(3-hydroxyphenyl)-4-(1-hydroxyethyl)-3,4,5,6-tetrahydro-2H-pyran
—— 4-(3-fluoro-5-hydroxyphenyl)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran 130723-23-8 C11H13FO3
4-(3-fluoro-5-hydroxyphenyl)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran
—— N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine 77795-17-6 C17H23NO3
N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine
—— 2-(6-m-hydroxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione 4126-28-7 C18H22O4
2-(6-m-hydroxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione
—— 5-(2-hydroxy-phenyl)-hexan-2-one 105401-58-9 C12H16O2
5-(2-hydroxy-phenyl)-hexan-2-one
—— 1-diethylamino-6-m-hydroxyphenylhexan-3-one 1444-60-6 C16H25NO2
1-diethylamino-6-m-hydroxyphenylhexan-3-one
—— 4-(2-hydroxypent-4-enyl)phenol 1190957-99-3 C11H14O2
4-(2-hydroxypent-4-enyl)phenol
—— (2-Hydroxy-5-nitrophenyl)-N,N,N-trimethylmethanaminium 62384-40-1 C10H15N2O3+
(2-Hydroxy-5-nitrophenyl)-N,N,N-trimethylmethanaminium
—— 2,3-dihydroxybenzaldehyde oxime 110827-84-4 C7H7NO3
2,3-dihydroxybenzaldehyde oxime
—— N-(3,6-dimethoxy-5-hydroxyphenyl)acetamide 75884-24-1 C10H13NO4
N-(3,6-dimethoxy-5-hydroxyphenyl)acetamide
—— 4-(5-fluoro-3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran 139368-21-1 C11H13FO2
4-(5-fluoro-3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran
—— 1-(2-hydroxy-phenyl)-pentan-3-one 61844-33-5 C11H14O2
1-(2-hydroxy-phenyl)-pentan-3-one
—— (+/-)-2-(3,4<i>t</i>-dimethyl-5<i>t</i>-phenyl-oxazolidin-2<i>r</i>-yl)-phenol —— C17H19NO2
(+/-)-2-(3,4<i>t</i>-dimethyl-5<i>t</i>-phenyl-oxazolidin-2<i>r</i>-yl)-phenol
—— (4S,5R)-(-)-5-ethyl-1-(4-hydroxy-3-methoxyphenethyl)-2-oxo-4-piperidineacetic acid 82260-59-1 C18H25NO5
(4S,5R)-(-)-5-ethyl-1-(4-hydroxy-3-methoxyphenethyl)-2-oxo-4-piperidineacetic acid
—— 2-allyl-3-bromo-4-fluorophenol 286836-28-0 C9H8BrFO
2-allyl-3-bromo-4-fluorophenol
—— 2-allyl-4-fluoro-5-bromophenol 1472652-17-7 C9H8BrFO
2-allyl-4-fluoro-5-bromophenol
—— (2E,5E)-2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone 247051-31-6 C21H20O5
(2E,5E)-2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone