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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-Nitrosalicylhydroxamsaeure 27286-97-1 C7H6N2O5
3-Nitrosalicylhydroxamsaeure
—— 2,5-Bis[(prop-2-enylamino)methyl]benzene-1,4-diol;hydrochloride 6342-06-9 C14H21ClN2O2
2,5-Bis[(prop-2-enylamino)methyl]benzene-1,4-diol;hydrochloride
—— 5-((S)-3-Methyl-pentyl)-benzene-1,3-diol 187084-16-8 C12H18O2
5-((S)-3-Methyl-pentyl)-benzene-1,3-diol
—— 2-hydroxy-1,3-xylyl-27-crown-8 116748-81-3 C22H36O9
2-hydroxy-1,3-xylyl-27-crown-8
—— trans-4-[N-(4'-hydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylic acid 81519-10-0 C15H19NO3
trans-4-[N-(4'-hydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylic acid
—— 1-(4-bromo-2-hydroxyphenyl)ethanone oxime 1095544-88-9 C8H8BrNO2
1-(4-bromo-2-hydroxyphenyl)ethanone oxime
—— 4-(3-hydroxy-4-nitro-phenyl)-5-(6-methylpyridin-2-yl)-1,3-thiazol-2-amine 813449-18-2 C15H12N4O3S
4-(3-hydroxy-4-nitro-phenyl)-5-(6-methylpyridin-2-yl)-1,3-thiazol-2-amine
—— 1-(4-(((2-hydroxyphenyl)imino)methyl)piperazin-1-yl)ethan-1-one 1423020-89-6 C13H17N3O2
1-(4-(((2-hydroxyphenyl)imino)methyl)piperazin-1-yl)ethan-1-one
—— 3-(2-hydroxy-5-nitro-benzyl)-histidine 66163-93-7 C13H14N4O5
3-(2-hydroxy-5-nitro-benzyl)-histidine
—— 5-Me-4-Ph-3-(2-OH-4-MeO-Phenyl)isoxazol 67526-79-8 C17H15NO3
5-Me-4-Ph-3-(2-OH-4-MeO-Phenyl)isoxazol
—— 2-methyl-benzo[<i>e</i>]pyrazolo[5,1-<i>c</i>][1,2,4]triazin-8-ol 73753-52-3 C10H8N4O
2-methyl-benzo[<i>e</i>]pyrazolo[5,1-<i>c</i>][1,2,4]triazin-8-ol
—— 4-(4-hydroxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-thione 68615-42-9 C17H14N2OS
4-(4-hydroxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-thione
—— 2-(2-Bromo-4-methoxy-phenyl)-N-[2-(3-hydroxy-4-methoxy-phenyl)-ethyl]-acetamide 66916-96-9 C18H20BrNO4
2-(2-Bromo-4-methoxy-phenyl)-N-[2-(3-hydroxy-4-methoxy-phenyl)-ethyl]-acetamide
—— salicylaldehyde S-ethylisothiosemicarbazone 7410-60-8 C10H13N3OS
salicylaldehyde S-ethylisothiosemicarbazone
—— N-(2-nitro-3-hydroxy-4-fluorobenzoyl)tris(hydroxymethyl)methylamine 81914-65-0 C11H13FN2O7
N-(2-nitro-3-hydroxy-4-fluorobenzoyl)tris(hydroxymethyl)methylamine
—— Acetic acid (E)-3-(4-hydroxy-phenyl)-2-methyl-allyl ester 124389-49-7 C12H14O3
Acetic acid (E)-3-(4-hydroxy-phenyl)-2-methyl-allyl ester
—— 3,5-dihydroxyanisole hydrate 957864-11-8 C7H8O3*H2O
3,5-dihydroxyanisole hydrate
—— 2,6-bis-ethylsulfanyl-4-nitro-phenol 99076-29-6 C10H13NO3S2
2,6-bis-ethylsulfanyl-4-nitro-phenol
—— 2-bromo-3-(3-fluoro-4-hydroxy-phenyl)-6a-methyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 1104634-36-7 C15H14BrFO2
2-bromo-3-(3-fluoro-4-hydroxy-phenyl)-6a-methyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one
—— (Z)-5-(2,4,5-trihydroxybenzylidene)-2-thioxothiazolidin-4-one 1208535-03-8 C10H7NO4S2
(Z)-5-(2,4,5-trihydroxybenzylidene)-2-thioxothiazolidin-4-one
—— 4-Nitro-2-{[(Z)-2,4,5-trichloro-phenylimino]-methyl}-phenol 15257-21-3 C13H7Cl3N2O3
4-Nitro-2-{[(Z)-2,4,5-trichloro-phenylimino]-methyl}-phenol
—— (4R,9R,19R,24R)-3,10,18,25-tetrazapentacyclo[25.3.1.112,16.04,9.019,24]dotriaconta-1(31),12(32),13,15,27,29-hexaene-31,32-diol 656811-78-8 C28H40N4O2
(4R,9R,19R,24R)-3,10,18,25-tetrazapentacyclo[25.3.1.112,16.04,9.019,24]dotriaconta-1(31),12(32),13,15,27,29-hexaene-31,32-diol
—— 4-(5-Cyclohexylamino-[1,3,4]thiadiazol-2-yl)-phenol 773057-01-5 C14H17N3OS
4-(5-Cyclohexylamino-[1,3,4]thiadiazol-2-yl)-phenol
—— 2-[2-[5-(hydroxymethyl)-7-methyl-4H-[1,3]dioxino[4,5-c]pyridin-7-ium-8-yl]ethyl]phenol;iodide 105551-24-4 C17H20NO4*I
2-[2-[5-(hydroxymethyl)-7-methyl-4H-[1,3]dioxino[4,5-c]pyridin-7-ium-8-yl]ethyl]phenol;iodide
—— 121131-41-7 C13H12Cl4N2OPt
—— Thiophosphoric acid O,O'-diethyl ester S-(2-hydroxy-5-nitro-phenyl) ester 3765-05-7 C10H14NO6PS
Thiophosphoric acid O,O'-diethyl ester S-(2-hydroxy-5-nitro-phenyl) ester
—— 2-[[[2-Phenyl-6-(trifluoromethyl)pyrimidin-4-yl]hydrazinylidene]methyl]phenol 481641-69-4 C18H13F3N4O
2-[[[2-Phenyl-6-(trifluoromethyl)pyrimidin-4-yl]hydrazinylidene]methyl]phenol
—— (2,4,6-trimethylbenzylidene)(2-hydroxyphenyl)amine 348152-11-4 C16H17NO
(2,4,6-trimethylbenzylidene)(2-hydroxyphenyl)amine
—— (2-hydroxy-3-methoxy-5-methyl-phenyl)-acetaldehyde 857543-04-5 C10H12O3
(2-hydroxy-3-methoxy-5-methyl-phenyl)-acetaldehyde
—— (Z)-1-<2,5-Dihydroxy-4-methyl-phenyl>-5-(N-methyl-amino)-4-hexen-3-on 156683-36-2 C14H19NO3
(Z)-1-<2,5-Dihydroxy-4-methyl-phenyl>-5-(N-methyl-amino)-4-hexen-3-on
—— 2-(2,3-Dihydroxyphenyl)ethyl hexadecanoate 1390634-27-1 C24H40O4
2-(2,3-Dihydroxyphenyl)ethyl hexadecanoate
—— 3-(2,3-Dihydroxyphenyl)propyl butanoate 1390634-32-8 C13H18O4
3-(2,3-Dihydroxyphenyl)propyl butanoate
—— N-cyclohexyl-4-hydroxy-2,3-dimethylbenzenecarbothioamide 120951-47-5 C15H21NOS
N-cyclohexyl-4-hydroxy-2,3-dimethylbenzenecarbothioamide
—— 2,4-dimethoxy-3-methyl-5-(2,4-pentadienyl)phenol 103993-05-1 C14H18O3
2,4-dimethoxy-3-methyl-5-(2,4-pentadienyl)phenol
—— 4-(4-Hydroxyphenyl)-3-methyl-1,2-oxazole-5-carboxylic acid 1781524-81-9 C11H9NO4
4-(4-Hydroxyphenyl)-3-methyl-1,2-oxazole-5-carboxylic acid
—— N-[(2-hydroxy-5-methylphenyl)methyl]-N-methylacetamide 75288-07-2 C11H15NO2
N-[(2-hydroxy-5-methylphenyl)methyl]-N-methylacetamide
—— E-4-benzyloxy-2-(4'-hydroxy-3'-methylbut-2'-enyl)phenol 154912-30-8 C18H20O3
E-4-benzyloxy-2-(4'-hydroxy-3'-methylbut-2'-enyl)phenol
—— N-[3-(Acetyl-{3-[3-(4-hydroxy-phenyl)-propionylamino]-propyl}-amino)-propyl]-3-(4-hydroxy-phenyl)-propionamide 50463-54-2 C26H35N3O5
N-[3-(Acetyl-{3-[3-(4-hydroxy-phenyl)-propionylamino]-propyl}-amino)-propyl]-3-(4-hydroxy-phenyl)-propionamide
—— N-(3-hydroxyphenyl)-N'-propan-2-ylethanimidamide 42717-35-1 C11H16N2O
N-(3-hydroxyphenyl)-N'-propan-2-ylethanimidamide
—— 590416-27-6 C26H25FN2O4
—— 5-[(4-hydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one 902799-72-8 C10H7NO2S2
5-[(4-hydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
—— 123431-70-9 C19H20Br2N2O2
—— 6-Chloro-3-fluoro-2-nitrophenol 872363-74-1 C6H3ClFNO3
6-Chloro-3-fluoro-2-nitrophenol
—— 4-(4-Bromotetrahydro-5-propyl-2H-pyran-2-yl)phenol 916155-03-8 C14H19BrO2
4-(4-Bromotetrahydro-5-propyl-2H-pyran-2-yl)phenol
—— 13-Hydroxy-bicyclo[8.3.1]tetradeca-1(13),10(14),11-triene-11,12-dicarboxylic acid dimethyl ester 67109-97-1 C18H24O5
13-Hydroxy-bicyclo[8.3.1]tetradeca-1(13),10(14),11-triene-11,12-dicarboxylic acid dimethyl ester
—— 2-[(isopropylimino)(pyridin-2-yl)methyl]phenol 1182372-37-7 C15H16N2O
2-[(isopropylimino)(pyridin-2-yl)methyl]phenol
—— 4-(2,5-dihydroxyphenyl)-2-(2-phenyl)ethyl-1,3-dioxolane 1104386-01-7 C17H18O4
4-(2,5-dihydroxyphenyl)-2-(2-phenyl)ethyl-1,3-dioxolane
—— (+)-3-[2-(tert-butyldimethylsilyloxy)but-3-ynyl]-5-methylphenol 745809-55-6 C17H26O2Si
(+)-3-[2-(tert-butyldimethylsilyloxy)but-3-ynyl]-5-methylphenol
—— 2.5-Dibrom-vanillin 854873-03-3 C8H6Br2O3
2.5-Dibrom-vanillin
—— 5-bromo-4-hydroxy-3-[5-(4-hydroxy-3-methoxy-phenyl)-1-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-6-methyl-pyran-2-one 73043-68-2 C22H18BrN3O7
5-bromo-4-hydroxy-3-[5-(4-hydroxy-3-methoxy-phenyl)-1-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-6-methyl-pyran-2-one