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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-(5-(4-hydroxy-3-methoxyphenyl)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol 1259435-13-6 C15H12N2O4S
4-(5-(4-hydroxy-3-methoxyphenyl)-1,3,4-thiadiazol-2-yl)benzene-1,3-diol
—— (R)-4-(2-amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol 1313485-89-0 C15H27NO3Si
(R)-4-(2-amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol
—— 4-sec-Heptyl-o-kresol 42433-61-4 C14H22O
4-sec-Heptyl-o-kresol
—— 2,6-bis-(butylsulfanyl-methyl)-4-methyl-phenol 61150-78-5 C17H28OS2
2,6-bis-(butylsulfanyl-methyl)-4-methyl-phenol
—— 3,5-dinitro-2,6-dimethylol-p-cresol 156424-34-9 C9H10N2O7
3,5-dinitro-2,6-dimethylol-p-cresol
—— 3-hydroxy-2-isopropoxy-4-methoxybenzaldehyde 1242062-15-2 C11H14O4
3-hydroxy-2-isopropoxy-4-methoxybenzaldehyde
—— 2-Hydroxy-5-methoxy-4-prenyloxybenzaldehyde 141590-39-8 C13H16O4
2-Hydroxy-5-methoxy-4-prenyloxybenzaldehyde
—— 2,3,6-trimethyl-4-nitrophenol 92892-06-3 C9H11NO3
2,3,6-trimethyl-4-nitrophenol
—— 2-<2-hydroxy-3-(phenylthio)propyl>-4-nitrophenol 126708-08-5 C15H15NO4S
2-<2-hydroxy-3-(phenylthio)propyl>-4-nitrophenol
—— 4-bromo-6-methoxybenzene-1,3-diol 1402158-29-5 C7H7BrO3
4-bromo-6-methoxybenzene-1,3-diol
—— 2-<3-hydroxy-2-(phenylthio)propyl>-4-nitrophenol 126708-18-7 C15H15NO4S
2-<3-hydroxy-2-(phenylthio)propyl>-4-nitrophenol
—— 2-bromo-4-chloro-5-methoxy-3-methylphenol 1233953-53-1 C8H8BrClO2
2-bromo-4-chloro-5-methoxy-3-methylphenol
—— (S)-5-(hydroxymethyl)-3-(4-hydroxyphenyl)-2-oxazolidinone 89201-80-9 C10H11NO4
(S)-5-(hydroxymethyl)-3-(4-hydroxyphenyl)-2-oxazolidinone
—— p-Toluamide, N-(2-(1-benzimidazolyl)ethyl)-, monopicrate 22261-49-0 C23H20N6O8
p-Toluamide, N-(2-(1-benzimidazolyl)ethyl)-, monopicrate
—— 3,4-bis(benzyloxy)-2-bromo-5-methoxyphenol 1170034-65-7 C21H19BrO4
3,4-bis(benzyloxy)-2-bromo-5-methoxyphenol
—— N-[3-(4-Hydroxy-phenyl)-propyl]-methanesulfonamide 477289-47-7 C10H15NO3S
N-[3-(4-Hydroxy-phenyl)-propyl]-methanesulfonamide
—— 5-(3'-hydroxy-3'-methylbutenyl)-2-methoxy-4-<(dimethylamino)methyl>phenol 127757-17-9 C15H23NO3
5-(3'-hydroxy-3'-methylbutenyl)-2-methoxy-4-<(dimethylamino)methyl>phenol
—— 2-methoxy-5-(3'-methyl-2'-butenyl)-4-<(dimethylamino)methyl>phenol 127757-24-8 C15H23NO2
2-methoxy-5-(3'-methyl-2'-butenyl)-4-<(dimethylamino)methyl>phenol
—— threo-1-C-syringylglycerol 951627-70-6 C11H16O6
threo-1-C-syringylglycerol
—— 5-Ethyl-4-(4-hydroxy-phenyl)-6-methyl-cyclohex-3-enecarboxylic acid 22921-20-6 C16H20O3
5-Ethyl-4-(4-hydroxy-phenyl)-6-methyl-cyclohex-3-enecarboxylic acid
—— 1,2-bis[2,4-dimethyl-5-(o-hydroxyphenyl)-3-thienyl]hexafluorocyclopentene 440671-11-4 C29H22F6O2S2
1,2-bis[2,4-dimethyl-5-(o-hydroxyphenyl)-3-thienyl]hexafluorocyclopentene
—— 2-(2,4-dihydroxybenzylidene)malononitrile 92279-39-5 C10H6N2O2
2-(2,4-dihydroxybenzylidene)malononitrile
—— 4-(2-Hydroxy-3,4,6-trimethyl-phenyl)-butyric acid 84978-26-7 C13H18O3
4-(2-Hydroxy-3,4,6-trimethyl-phenyl)-butyric acid
—— 2-(pent-4-en-2-yl)phenol 1186642-13-6 C11H14O
2-(pent-4-en-2-yl)phenol
—— 14167-20-5 C16H16N2NiO2
—— 3-amino-2-fluoro-4-methylphenol 1427406-97-0 C7H8FNO
3-amino-2-fluoro-4-methylphenol
—— 1,4-bis-(2-hydroxy-thiobenzoyl)-piperazine 101793-38-8 C18H18N2O2S2
1,4-bis-(2-hydroxy-thiobenzoyl)-piperazine
—— 2,4,5-Trichlor-3,6-difluor-phenol 2375-66-8 C6HCl3F2O
2,4,5-Trichlor-3,6-difluor-phenol
—— 2-Chlor-acetamido-4-methoxyphenol 6238-93-3 C9H10ClNO3
2-Chlor-acetamido-4-methoxyphenol
—— cyclopropanecarboxylic acid (2-hydroxy-5-methoxyphenyl)amide 883244-97-1 C11H13NO3
cyclopropanecarboxylic acid (2-hydroxy-5-methoxyphenyl)amide
—— m-Hydroxy-acetophenon-hydrazon 5757-78-8 C8H10N2O
m-Hydroxy-acetophenon-hydrazon
—— 2,3,9,10-Tetrahydroxy-6,7-dihydro-5H-dibenzo<a,c>cyclohepten 17425-65-9 C15H14O4
2,3,9,10-Tetrahydroxy-6,7-dihydro-5H-dibenzo<a,c>cyclohepten
—— 4-[(3-hydroxy-phenyl)-thioacetyl]-morpholine 500284-27-5 C12H15NO2S
4-[(3-hydroxy-phenyl)-thioacetyl]-morpholine
—— 25,26,27-trihydroxy-28-calix[4]monoquinone-17-ethylene ketal 386223-92-3 C30H26O6
25,26,27-trihydroxy-28-calix[4]monoquinone-17-ethylene ketal
—— 4,5-dihydroxy-2-methoxy-benzaldehyde 5689-99-6 C8H8O4
4,5-dihydroxy-2-methoxy-benzaldehyde
—— 4.5-Dihydroxy-2-methoxy-1-aminoaethyl-benzol 14901-09-8 C9H13NO3
4.5-Dihydroxy-2-methoxy-1-aminoaethyl-benzol
—— 2-fluoro-4-[5-(3-fluoro-5-hydroxyphenyl)thien-2-yl]phenol 1193524-97-8 C16H10F2O2S
2-fluoro-4-[5-(3-fluoro-5-hydroxyphenyl)thien-2-yl]phenol
—— 5-Methoxy-2-(tetrahydro-pyran-2-yl)-phenol 120649-45-8 C12H16O3
5-Methoxy-2-(tetrahydro-pyran-2-yl)-phenol
—— 3-(5-Dodecyloxy-2-hydroxy-benzyl)-1-methyl-1H-pyridin-2-one 672939-87-6 C25H37NO3
3-(5-Dodecyloxy-2-hydroxy-benzyl)-1-methyl-1H-pyridin-2-one
—— 3-Methoxy-2,4,5-trimethylphenol 34883-04-0 C10H14O2
3-Methoxy-2,4,5-trimethylphenol
—— 2-4-(diethylamino-2-hydroxybenzylideneamino)-5-nitrophenol 415687-15-9 C17H19N3O4
2-4-(diethylamino-2-hydroxybenzylideneamino)-5-nitrophenol
—— 3-(2-hydroxy-4,6-dimethoxyphenyl)-6-phenylcyclohex-2-en-1-one 89059-56-3 C20H20O4
3-(2-hydroxy-4,6-dimethoxyphenyl)-6-phenylcyclohex-2-en-1-one
—— 6-acetyl-3-(2-hydroxy-4-methoxyphenyl)-5-phenyl-cyclohex-2-en-1one 89059-51-8 C21H20O4
6-acetyl-3-(2-hydroxy-4-methoxyphenyl)-5-phenyl-cyclohex-2-en-1one
—— 6-(2-Hydroxy-4-methoxy-phenyl)-4-phenyl-2,3a,4,5-tetrahydro-indazol-3-one 101986-20-3 C20H18N2O3
6-(2-Hydroxy-4-methoxy-phenyl)-4-phenyl-2,3a,4,5-tetrahydro-indazol-3-one
—— 3-(2-hydroxy-4-methoxyphenyl)-5-phenylcyclohex-2-en-1-one 89059-49-4 C19H18O3
3-(2-hydroxy-4-methoxyphenyl)-5-phenylcyclohex-2-en-1-one
—— 2,6-di-<i>tert</i>-butyl-4-oxiranylmethoxy-phenol 7020-08-8 C17H26O3
2,6-di-<i>tert</i>-butyl-4-oxiranylmethoxy-phenol
—— 3,5-dimethoxy-4-(((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)phenol 1415456-03-9 C18H26O4
3,5-dimethoxy-4-(((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)phenol
—— 2-methyl-4-hydroxy-anilino-2-imidazoline hydrochloride 95668-59-0 C10H13N3O*ClH
2-methyl-4-hydroxy-anilino-2-imidazoline hydrochloride
—— 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfone 40654-56-6 C12H6Cl2N2O8S
5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfone
—— (RS)-N-(4-cyano-benzyl)-2-(3-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide 1055905-12-8 C18H18N2O4
(RS)-N-(4-cyano-benzyl)-2-(3-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide