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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
—— 2-Methyl-6-nitroso-phenol 59973-84-1 C7H7NO2
2-Methyl-6-nitroso-phenol
—— 2-(tert-butyldiphenylsilyl)phenol 82772-30-3 C22H24OSi
2-(tert-butyldiphenylsilyl)phenol
—— 5-Butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilylphenol 1289448-26-5 C19H33BO3Si
5-Butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilylphenol
—— 5-methyl-2-phenyl-4-vanillylidene-2,4-dihydro-pyrazol-3-one 81836-90-0 C18H16N2O3
5-methyl-2-phenyl-4-vanillylidene-2,4-dihydro-pyrazol-3-one
—— rubrolide R 1608121-21-6 C22H20O4
rubrolide R
—— Propan-2-yl 6-hydroxy-2-[(3-hydroxy-4-methoxy-5-methylphenyl)methyl]-4-methyl-3-oxopiperazine-1-carboxylate 310903-99-2 C18H26N2O6
Propan-2-yl 6-hydroxy-2-[(3-hydroxy-4-methoxy-5-methylphenyl)methyl]-4-methyl-3-oxopiperazine-1-carboxylate
—— 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione 221146-80-1 C18H24N2O6
3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione
—— (RS)-10-<2'-hydroxy-5'-methyl-3'-(methylthio)phenyl>-2-decanol 113017-37-1 C18H30O2S
(RS)-10-<2'-hydroxy-5'-methyl-3'-(methylthio)phenyl>-2-decanol
—— (+/-)-saccardianine C 3767-85-9 C13H13NO
(+/-)-saccardianine C
—— 2-bromo-6-[5-(4-methoxy-phenyl)-isoxazol-3-yl]-4-methyl-phenol 29976-92-9 C17H14BrNO3
2-bromo-6-[5-(4-methoxy-phenyl)-isoxazol-3-yl]-4-methyl-phenol
—— 4-amino-2,6-dibromo-phenol; hydrochloride 56967-16-9 C6H5Br2NO*ClH
4-amino-2,6-dibromo-phenol; hydrochloride
—— N-(3-(4-hydroxyphenyl)propyl)acetamide 58187-52-3 C11H15NO2
N-(3-(4-hydroxyphenyl)propyl)acetamide
—— [2,3,4,5,6-3H<sub>5</sub>]phenol 1026281-32-2 C6H6O
[2,3,4,5,6-3H<sub>5</sub>]phenol
—— [3,5-3H2]-phenol 860624-00-6 C6H6O
[3,5-3H2]-phenol
—— 5-dimetylaminomethyl-2-hydroxy-3-methoxybenzaldehyde 87743-12-2 C11H15NO3
5-dimetylaminomethyl-2-hydroxy-3-methoxybenzaldehyde
—— Resorcin[4]arene 125748-07-4 C28H24O8
Resorcin[4]arene
—— 5,17-Di-tert-butyl-11,23-bis<(dimethylamino)methyl>calix<4>arene-25,26,27,28-tetrol 170940-13-3 C42H54N2O4
5,17-Di-tert-butyl-11,23-bis<(dimethylamino)methyl>calix<4>arene-25,26,27,28-tetrol
—— 1-(4-hydroxyphenyl)-2-(4-pyridyl)ethane 263872-14-6 C13H13NO
1-(4-hydroxyphenyl)-2-(4-pyridyl)ethane
—— 5,17-bis(cyanomethyl)calix<4>25,26,27,28-tetrol 170940-16-6 C32H26N2O4
5,17-bis(cyanomethyl)calix<4>25,26,27,28-tetrol
—— 5,17-Di-tert-butyl-11,23-bis(cyanomethyl)calix[4]arene-25,26,27,28-tetrol 170940-14-4 C40H42N2O4
5,17-Di-tert-butyl-11,23-bis(cyanomethyl)calix[4]arene-25,26,27,28-tetrol
—— 4-bromo-6-[[2-(2-pyridin-2-ylethylsulfanyl)ethylamino]methylidene]cyclohexa-2,4-dien-1-one 615257-09-5 C16H17BrN2OS
4-bromo-6-[[2-(2-pyridin-2-ylethylsulfanyl)ethylamino]methylidene]cyclohexa-2,4-dien-1-one
—— 7-(2-hydroxy-5-nitrobenzyl)-5,6,7,8,9,10-hexahydro-2H-1,13,4,7,10-benzodioxatriazacyclopentadecine-3,11(4H,12H)-dione 947609-64-5 C21H24N4O7
7-(2-hydroxy-5-nitrobenzyl)-5,6,7,8,9,10-hexahydro-2H-1,13,4,7,10-benzodioxatriazacyclopentadecine-3,11(4H,12H)-dione
—— 2,3,4,5-tetrachloro-6-methylphenol 19303-88-9 C7H4Cl4O
2,3,4,5-tetrachloro-6-methylphenol
—— 1,8-bis-(p-hydroxyphenyl)octane 3682-96-0 C20H26O2
1,8-bis-(p-hydroxyphenyl)octane
—— (E)-1-[2,4-dihydroxy-3-(morpholin-4-ylmethyl)phenyl]-3-pyridin-2-ylprop-2-en-1-one 1064287-97-3 C19H20N2O4
(E)-1-[2,4-dihydroxy-3-(morpholin-4-ylmethyl)phenyl]-3-pyridin-2-ylprop-2-en-1-one
—— 4-[12-(4-Hydroxyphenyl)dodecyl]phenol 107259-35-8 C24H34O2
4-[12-(4-Hydroxyphenyl)dodecyl]phenol
—— 2,6-bis(di-t-butylphosphinomethylene)-4-methoxyphenol 647861-84-5 C25H46O2P2
2,6-bis(di-t-butylphosphinomethylene)-4-methoxyphenol
—— 2,6-bis(bromomethylene)-4-methoxyphenol 129316-20-7 C9H10Br2O2
2,6-bis(bromomethylene)-4-methoxyphenol
—— propylamine; picrate 16639-72-8 C3H9N*C6H3N3O7
propylamine; picrate
—— p-benzylcalix[5]arene 158778-92-8 C70H60O5
p-benzylcalix[5]arene
—— 2-Hydroxy-5-(dec-9enyloxy)benzaldehyde 201672-98-2 C17H24O3
2-Hydroxy-5-(dec-9enyloxy)benzaldehyde
—— 4-(dec-9-enyloxy)phenol 117560-77-7 C16H24O2
4-(dec-9-enyloxy)phenol
—— 2,4,6-trimorpholinylmethyl-1,3-dihydroxybenzene 23409-80-5 C21H33N3O5
2,4,6-trimorpholinylmethyl-1,3-dihydroxybenzene
—— 3-hydroxy-5-methoxybenzylamine 149555-67-9 C8H11NO2
3-hydroxy-5-methoxybenzylamine
—— 4,12,16,24-tetrahydroxycalix<4>arene 140396-87-8 C28H24O4
4,12,16,24-tetrahydroxycalix<4>arene
—— 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)pent-4-enyl>phenol 223268-47-1 C19H23NO
2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)pent-4-enyl>phenol
—— 5-{[(2-cyclohex-1-enyl-ethyl)methylamino]methyl}-2-methoxyphenol 363132-75-6 C17H25NO2
5-{[(2-cyclohex-1-enyl-ethyl)methylamino]methyl}-2-methoxyphenol
—— 5-({[2-(1-hydroxycyclohexyl)ethyl]methylamino}methyl)-2-methoxyphenol 363132-93-8 C17H27NO3
5-({[2-(1-hydroxycyclohexyl)ethyl]methylamino}methyl)-2-methoxyphenol
—— 4-nitro-3,5-bis(trifluoromethyl)phenol 168123-63-5 C8H3F6NO3
4-nitro-3,5-bis(trifluoromethyl)phenol
—— 3-(4-hydroxy-3-nitro)phenyl-3-(trifluoromethyl)-3H-diazirine 125680-82-2 C8H4F3N3O3
3-(4-hydroxy-3-nitro)phenyl-3-(trifluoromethyl)-3H-diazirine
—— (E)-methyl (3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-(hydroxyimino)propanoate 343256-47-3 C11H11Br2NO5
(E)-methyl (3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-(hydroxyimino)propanoate
—— [(E)-4-[3-hydroxy-2-(hydroxymethyl)-4,6-dimethoxy-5-methylphenyl]but-2-enyl] 2,2-dimethylpropanoate 271578-67-7 C19H28O6
[(E)-4-[3-hydroxy-2-(hydroxymethyl)-4,6-dimethoxy-5-methylphenyl]but-2-enyl] 2,2-dimethylpropanoate
—— 4-[(E)-4-[tert-butyl(dimethyl)silyl]oxybut-2-enyl]-3-methoxy-6-(methoxymethoxy)-2-methylphenol 351379-95-8 C20H34O5Si
4-[(E)-4-[tert-butyl(dimethyl)silyl]oxybut-2-enyl]-3-methoxy-6-(methoxymethoxy)-2-methylphenol
—— N-benzyl-3-(3-hydroxy-4-methoxyphenyl)propylamine 253135-13-6 C17H21NO2
N-benzyl-3-(3-hydroxy-4-methoxyphenyl)propylamine
—— N-benzyl-3-(3-hydroxy-4-methoxyphenyl)propanamide 253135-11-4 C17H19NO3
N-benzyl-3-(3-hydroxy-4-methoxyphenyl)propanamide
—— 2,6-bis(butyltelluro)phenol 1442114-98-8 C14H22OTe2
2,6-bis(butyltelluro)phenol
—— 2-(butyltelluro)phenol 1442114-84-2 C10H14OTe
2-(butyltelluro)phenol
—— 4,12,16,24-tetrahydroxy-5,23-dimethylcalix<4>arene 173974-39-5 C30H28O4
4,12,16,24-tetrahydroxy-5,23-dimethylcalix<4>arene
—— 5,23-di-tert-butyl-4,12,16,24-tetrahydroxy-11,17-dimethylcalix<4>arene 173974-38-4 C38H44O4
5,23-di-tert-butyl-4,12,16,24-tetrahydroxy-11,17-dimethylcalix<4>arene
—— 5-(1-methyl-pentyl)-resorcinol 59656-56-3 C12H18O2
5-(1-methyl-pentyl)-resorcinol