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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
—— 1,2,3,4,5,6-hexahydro-6-(2',3',4'-trihydroxyphenyl)-1,3,5-triazine-2,4-dione —— C9H9N3O5
1,2,3,4,5,6-hexahydro-6-(2',3',4'-trihydroxyphenyl)-1,3,5-triazine-2,4-dione
—— C-bromooctylpyrogallol[4]arene —— C60H84Br4O12
C-bromooctylpyrogallol[4]arene
—— C-chlorobutylpyrogallol[4]arene —— C44H52Cl4O12
C-chlorobutylpyrogallol[4]arene
—— 4,6,16,18-tetraaza-26,28-dihydroxy-5,17-diphenyl-2,8,14,20-tetraoxacalix[4]arene —— C32H20N4O6
4,6,16,18-tetraaza-26,28-dihydroxy-5,17-diphenyl-2,8,14,20-tetraoxacalix[4]arene
—— 5,5',5"-(1,3,5-triazine-2,4,6-triyl)tris(azanediyl)tribenzene-1,3-diol —— C21H18N6O6
5,5',5"-(1,3,5-triazine-2,4,6-triyl)tris(azanediyl)tribenzene-1,3-diol
—— 4-(1-hexyn-1-yl)phenol —— C12H14O
4-(1-hexyn-1-yl)phenol
—— 1,4-bis(4-hydroxyphenylethynyl)benzene —— C22H14O2
1,4-bis(4-hydroxyphenylethynyl)benzene
—— 2-bromo-4-n-butoxyphenol —— C10H13BrO2
2-bromo-4-n-butoxyphenol
—— 3-[3-(3-hydroxyphenyl)furan-2-yl]quinuclidin-2-ene —— C17H17NO2
3-[3-(3-hydroxyphenyl)furan-2-yl]quinuclidin-2-ene
—— 3-(decan-2-yl)-phenol —— C16H26O
3-(decan-2-yl)-phenol
—— hexadecyl(2-hydroxybenzyl)diphenylphosphonium chloride —— C35H50OP*Cl
hexadecyl(2-hydroxybenzyl)diphenylphosphonium chloride
—— 3-(1,4-cyclohexadien-3-yl)phenol —— C12H12O
3-(1,4-cyclohexadien-3-yl)phenol
—— 1,2-bis[3-hydroxyphenyl]ethyne —— C14H10O2
1,2-bis[3-hydroxyphenyl]ethyne
—— 3-(3-((tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-yl)phenol —— C14H16O3
3-(3-((tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-yl)phenol
—— (E)-2-(3-hydroxyphenyl)ethene-1-sulfonyl fluoride —— C8H7FO3S
(E)-2-(3-hydroxyphenyl)ethene-1-sulfonyl fluoride
—— 3-[(4hydroxyphenyl)ethynyl]phenol —— C14H10O2
3-[(4hydroxyphenyl)ethynyl]phenol
—— tert-butyl 3-(2-(2-(2-(3-(3-hydroxyphenyl)prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)propanoate —— C22H32O7
tert-butyl 3-(2-(2-(2-(3-(3-hydroxyphenyl)prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)propanoate
—— 4,5,6-trimethyl-1-nitrophenol —— C9H11NO3
4,5,6-trimethyl-1-nitrophenol
—— 4-(methyldisulfanyl)phenol —— C7H8OS2
4-(methyldisulfanyl)phenol
—— S-4-hydroxyphenyl methanesulfonothioate —— C7H8O3S2
S-4-hydroxyphenyl methanesulfonothioate
—— 4'-hydroxyphenyldisulfide —— C6H6OS2
4'-hydroxyphenyldisulfide
—— dodecyl-4-hydroxyphenyl disulfide —— C18H30OS2
dodecyl-4-hydroxyphenyl disulfide
—— 3,3'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(2-(4-hydroxyphenyl)thiazolidin-4-one) —— C32H28N2O4S2
3,3'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(2-(4-hydroxyphenyl)thiazolidin-4-one)
—— 3,3'-(biphenyl-4,4'-diyl)bis(2-(4-hydroxy-3-methoxyphenyl)thiazolidin-4-one) —— C32H28N2O6S2
3,3'-(biphenyl-4,4'-diyl)bis(2-(4-hydroxy-3-methoxyphenyl)thiazolidin-4-one)
—— 5-hydroxy-1,2,3-ninhydrine —— C9H4O4
5-hydroxy-1,2,3-ninhydrine
—— 3-(3-hydroxyphenyl)-propane-1,2-diol —— C9H12O3
3-(3-hydroxyphenyl)-propane-1,2-diol
—— 2-((allyloxy)methyl)-4-nitrophenol —— C10H11NO4
2-((allyloxy)methyl)-4-nitrophenol
—— (S)-4-(2-chloro-1-hydroxyethyl)phenol —— C8H9ClO2
(S)-4-(2-chloro-1-hydroxyethyl)phenol
—— 3-pentadec-10-ynylbenzene-1,2-diol —— C21H32O2
3-pentadec-10-ynylbenzene-1,2-diol
—— 4-(4'-hydroxyphenyl)-2-butyl acetate —— C12H16O3
4-(4'-hydroxyphenyl)-2-butyl acetate
—— rhododendrol monoacetate —— C12H16O3
rhododendrol monoacetate
—— cis-N-{3-[5-(4-hydroxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide —— C15H21NO5
cis-N-{3-[5-(4-hydroxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide
—— (E)-3-(dimethylamino)-1-(2-hydroxy-4-methylphenyl)prop-2-en-1-one —— C12H15NO2
(E)-3-(dimethylamino)-1-(2-hydroxy-4-methylphenyl)prop-2-en-1-one
—— N,N'-bis(4'-hydroxy-3',5'-dimethoxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane —— C30H46N2O10
N,N'-bis(4'-hydroxy-3',5'-dimethoxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
—— N-(4-hydroxy-3,5-dimethoxybenzyl)-1,4,7-trioxa-10-azacyclododecane —— C17H27NO6
N-(4-hydroxy-3,5-dimethoxybenzyl)-1,4,7-trioxa-10-azacyclododecane
—— N-(4'-hydroxy-3',5'-dimethoxybenzyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane —— C19H31NO7
N-(4'-hydroxy-3',5'-dimethoxybenzyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane
—— 4-(benzo[d][1,3]dioxol-5-yl)-2,6-dimethoxyphenol —— C15H14O5
4-(benzo[d][1,3]dioxol-5-yl)-2,6-dimethoxyphenol
—— 4-(3-hexylthiophen-2-yl)-2,6-dimethoxyphenol —— C18H24O3S
4-(3-hexylthiophen-2-yl)-2,6-dimethoxyphenol
—— 3-isobutoxy-5-methoxyphenol —— C11H16O3
3-isobutoxy-5-methoxyphenol
—— 3-(3,5-dimethoxy-4-hydroxybenzyl)-benzothiazole-2-thione —— C16H15NO3S2
3-(3,5-dimethoxy-4-hydroxybenzyl)-benzothiazole-2-thione
—— 2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol hydrochloride —— C11H17NO3*ClH
2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol hydrochloride
—— diethyl (4-hydroxy-3,5-dimethoxybenzyl)phosphonate —— C13H21O6P
diethyl (4-hydroxy-3,5-dimethoxybenzyl)phosphonate
—— 2,6-dimethoxy-4-(2-methylbenzo[b]thiophen-3-yl)phenol —— C17H16O3S
2,6-dimethoxy-4-(2-methylbenzo[b]thiophen-3-yl)phenol
—— 2,6-dimethoxy-3-(2,3-dihydro-1H-inden-1-yl)phenol —— C17H18O3
2,6-dimethoxy-3-(2,3-dihydro-1H-inden-1-yl)phenol
—— tert-butyl (R)-(1-(4-fluoro-3-hydroxyphenyl)ethyl)carbamate —— C13H18FNO3
tert-butyl (R)-(1-(4-fluoro-3-hydroxyphenyl)ethyl)carbamate
—— 2-(1-Hydroxy-2-nonynyl)-4-methoxyphenol —— C16H22O3
2-(1-Hydroxy-2-nonynyl)-4-methoxyphenol
—— 4-bromo-N’-(2-hydroxy-5-methoxybenzylidene)benzohydrazide —— C15H13BrN2O3
4-bromo-N’-(2-hydroxy-5-methoxybenzylidene)benzohydrazide
—— (S)-(-)-α-(3-hydroxy-2-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol —— C21H26FNO3
(S)-(-)-α-(3-hydroxy-2-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
—— N'-(2-hydroxy-5-methoxybenzylidene)-4-methoxybenzohydrazide —— C16H16N2O4
N'-(2-hydroxy-5-methoxybenzylidene)-4-methoxybenzohydrazide
—— (Z)-2-(5-(2-hydroxy-5-methoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid —— C13H11NO5S2
(Z)-2-(5-(2-hydroxy-5-methoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid