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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-hydroxy-3-isopropenyl-5-nitrobenzonitrile 942216-08-2 C10H8N2O3
4-hydroxy-3-isopropenyl-5-nitrobenzonitrile
—— 4-methyl-3-(methylamino)phenol 6265-13-0 C8H11NO
4-methyl-3-(methylamino)phenol
—— seco-plakortolide N 1266187-49-8 C26H42O5
seco-plakortolide N
—— 3-methyl-2-(2,2,4,4-tetramethyl-1-oxo-1λ<sup>5</sup>-phosphetan-1-yloxy)-phenol 62451-26-7 C14H21O3P
3-methyl-2-(2,2,4,4-tetramethyl-1-oxo-1λ<sup>5</sup>-phosphetan-1-yloxy)-phenol
—— 3-(2,2,2-trifluoroacetylamino)methylphenol 226070-65-1 C9H8F3NO2
3-(2,2,2-trifluoroacetylamino)methylphenol
—— 4-(4'-Hydroxyphenoxy)-methyl-benzoesaeure 254116-46-6 C14H12O4
4-(4'-Hydroxyphenoxy)-methyl-benzoesaeure
—— 4-hydroxy-3-methoxybenzeneacetic acid 8-methylnonyl ester 240110-07-0 C19H30O4
4-hydroxy-3-methoxybenzeneacetic acid 8-methylnonyl ester
—— 2-(cyclohexylmethyl)-hydroquinone 94854-08-7 C13H18O2
2-(cyclohexylmethyl)-hydroquinone
—— (E)-3-(2-bromo-3-hydroxy-4-methoxyphenyl)prop-2-enenitrile 157330-37-5 C10H8BrNO2
(E)-3-(2-bromo-3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— AG 974 148741-31-5 C10H5IN2O2
AG 974
—— (E,E)-6-(4-Hydroxyphenyl)-N-(2-methylpropyl)-2,4-hexadienamide 120231-90-5 C16H21NO2
(E,E)-6-(4-Hydroxyphenyl)-N-(2-methylpropyl)-2,4-hexadienamide
—— 4-[(4E)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-methyl-5-oxoimidazol-1-yl]butanoic acid;piperazine 73043-53-5 C36H46N6O10
4-[(4E)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-2-methyl-5-oxoimidazol-1-yl]butanoic acid;piperazine
—— 1-(4-(2-(Cyclopentylmethoxy)ethyl)phenoxy)-3-isopropylaminopropan-2-ol fumarate 63686-85-1 C44H70N2O10
1-(4-(2-(Cyclopentylmethoxy)ethyl)phenoxy)-3-isopropylaminopropan-2-ol fumarate
—— Phenol diisobutene 84848-74-8 C14H22O
Phenol diisobutene
—— 2-allyl-4-methoxy-3-(methoxymethoxy)phenol 1247734-20-8 C12H16O4
2-allyl-4-methoxy-3-(methoxymethoxy)phenol
—— 3-(Pentadec-7-en-1-yl)phenol 17793-52-1 C21H34O
3-(Pentadec-7-en-1-yl)phenol
—— 4-(tetrahydro-2H-pyran-2-yl)phenol 66123-79-3 C11H14O2
4-(tetrahydro-2H-pyran-2-yl)phenol
—— Phenol, 3-[2-amino-1-[(1-methylethyl)amino]ethyl]- 1780716-28-0 C11H18N2O
Phenol, 3-[2-amino-1-[(1-methylethyl)amino]ethyl]-
—— 2-Pyrrolidinone, 4-[[1-(2-hydroxyphenyl)ethyl]amino]- 1700175-49-0 C12H16N2O2
2-Pyrrolidinone, 4-[[1-(2-hydroxyphenyl)ethyl]amino]-
—— Bis(2,4,6-trichlorophenolato)diimidazolecopper(II) monohydrate 58748-61-1 C18H16Cl6CuN4O3
Bis(2,4,6-trichlorophenolato)diimidazolecopper(II) monohydrate
—— 5-[(7Z)-Pentadec-7-en-1-yl]benzene-1,3-diol 1640287-40-6 C21H34O2
5-[(7Z)-Pentadec-7-en-1-yl]benzene-1,3-diol
—— 3-[(7Z)-Pentadec-7-en-1-yl]phenol 936109-15-8 C21H34O
3-[(7Z)-Pentadec-7-en-1-yl]phenol
—— 3-Bromo-4-methoxy-2-methylphenol 1332271-55-2 C8H9BrO2
3-Bromo-4-methoxy-2-methylphenol
—— 2,3-Diamino-6-bromophenol 1803592-72-4 C6H7BrN2O
2,3-Diamino-6-bromophenol
—— 3,5-dimethoxy-2-methyl-hydroquinone 226998-69-2 C9H12O4
3,5-dimethoxy-2-methyl-hydroquinone
—— 2-[(E)-2-(2-Hydroxy-5-nitro-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium 90281-24-6 C19H19N2O3
2-[(E)-2-(2-Hydroxy-5-nitro-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium
—— 254444-53-6 C18H32OSn
—— 2-(7-Chloro-4,4,5,5,6,6,7,7-octafluoro-heptyl)-benzene-1,4-diol 223139-89-7 C13H11ClF8O2
2-(7-Chloro-4,4,5,5,6,6,7,7-octafluoro-heptyl)-benzene-1,4-diol
—— 2-(4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluoro-nonyl)-benzene-1,4-diol 256342-49-1 C15H11F13O2
2-(4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluoro-nonyl)-benzene-1,4-diol
—— tri(propan-2-yl)silyl N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]carbamate 391609-22-6 C19H33NO4Si
tri(propan-2-yl)silyl N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]carbamate
—— (1R,11R,13R,15S)-11-allyl-7,15-dihydroxy-10,17-dioxatricyclo[11.3.1.0<sup>3,8</sup>]heptadeca-3,5,7-trien-9-one 365218-59-3 C18H22O5
(1R,11R,13R,15S)-11-allyl-7,15-dihydroxy-10,17-dioxatricyclo[11.3.1.0<sup>3,8</sup>]heptadeca-3,5,7-trien-9-one
—— 11β,13-dihydrolactuprin-15-al 374536-44-4 C23H22O7
11β,13-dihydrolactuprin-15-al
—— 2,6-Dichloro-4-hydroxy-3,5-dimethoxybenzeneethanol 108544-91-8 C10H12Cl2O4
2,6-Dichloro-4-hydroxy-3,5-dimethoxybenzeneethanol
—— Ethyl 2a-hydroxy-17,80-dioxaoctacyclo[85.2.2.27,10.213,16.243,46.251,54.281,84.12,6]dohecta-a(10),1(89),1a(7),2(2a),3,5,8,13(99),14,16(98),43(97),44,46(96),51,53,81,83,87,90,92,94-henicosaen-11,41,47,49,55,85-hexayne-4-carboxylate 235433-87-1 C103H124O5
Ethyl 2a-hydroxy-17,80-dioxaoctacyclo[85.2.2.27,10.213,16.243,46.251,54.281,84.12,6]dohecta-a(10),1(89),1a(7),2(2a),3,5,8,13(99),14,16(98),43(97),44,46(96),51,53,81,83,87,90,92,94-henicosaen-11,41,47,49,55,85-hexayne-4-carboxylate
—— Benzeneethanol, 2,6-dichloro-4-hydroxy-3,5-dimethoxy-alpha-methyl- 108545-03-5 C11H14Cl2O4
Benzeneethanol, 2,6-dichloro-4-hydroxy-3,5-dimethoxy-alpha-methyl-
—— 5,17-Diamino-11,23,29-trimethylhexacyclo[25.3.1.13,7.19,13.115,19.121,25]pentatriaconta-1(30),3(35),4,6,9,11,13(34),15,17,19(33),21,23,25(32),27(31),28-pentadecaene-31,32,33,34,35-pentol 489426-56-4 C38H38N2O5
5,17-Diamino-11,23,29-trimethylhexacyclo[25.3.1.13,7.19,13.115,19.121,25]pentatriaconta-1(30),3(35),4,6,9,11,13(34),15,17,19(33),21,23,25(32),27(31),28-pentadecaene-31,32,33,34,35-pentol
—— 4-[(3,3-dimethyloxiran-2-yl)methyl]-N,N-diethyl-3-hydroxy-5-methoxybenzamide 908609-70-1 C17H25NO4
4-[(3,3-dimethyloxiran-2-yl)methyl]-N,N-diethyl-3-hydroxy-5-methoxybenzamide
—— 2,3,4-(CH3O)3C6H2C(H)=N[2-(OH)-4-CH3C6H3] 449207-03-8 C17H19NO4
2,3,4-(CH3O)3C6H2C(H)=N[2-(OH)-4-CH3C6H3]
—— tert-butyl N-[[2-hydroxy-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]methyl]carbamate 481633-15-2 C18H28N2O5
tert-butyl N-[[2-hydroxy-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]methyl]carbamate
—— 22,28,34,39-Tetratert-butyl-43,44-dihydroxy-3,9,12,18-tetraoxa-6,15-diazahexacyclo[18.15.7.126,30.137,41.02,32.019,24]tetratetraconta-1,19,21,23,26(44),27,29,32,34,37,39,41(43)-dodecaene-5,16-dione 136158-06-0 C54H72N2O8
22,28,34,39-Tetratert-butyl-43,44-dihydroxy-3,9,12,18-tetraoxa-6,15-diazahexacyclo[18.15.7.126,30.137,41.02,32.019,24]tetratetraconta-1,19,21,23,26(44),27,29,32,34,37,39,41(43)-dodecaene-5,16-dione
—— 13,19,25,39,45,51,56,65-Octatert-butyl-3,6,9,29,32,35-hexaoxa-16,22,42,48,53,59,62,68-octathiaundecacyclo[35.15.7.711,27.117,21.143,47.154,58.02,49.010,15.023,28.036,41.163,67]heptaconta-1,10,12,14,17,19,21(69),23,25,27,36,38,40,43(61),44,46,49,51,54,56,58(60),63(70),64,66-tetracosaene-60,61,69,70-tetrol 581094-74-8 C88H108O10S8
13,19,25,39,45,51,56,65-Octatert-butyl-3,6,9,29,32,35-hexaoxa-16,22,42,48,53,59,62,68-octathiaundecacyclo[35.15.7.711,27.117,21.143,47.154,58.02,49.010,15.023,28.036,41.163,67]heptaconta-1,10,12,14,17,19,21(69),23,25,27,36,38,40,43(61),44,46,49,51,54,56,58(60),63(70),64,66-tetracosaene-60,61,69,70-tetrol
—— Acetic acid (R)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester 603095-24-5 C17H25BrO5
Acetic acid (R)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester
—— o-Nitrotyramine 3998-61-6 C8H10N2O3
o-Nitrotyramine
—— 4-(6-hydroxy-7,8-dimethyl-2,3-dihydrobenzo[b][1,4]oxathiin-2-yl)benzene-1,2-diol 958463-27-9 C16H16O4S
4-(6-hydroxy-7,8-dimethyl-2,3-dihydrobenzo[b][1,4]oxathiin-2-yl)benzene-1,2-diol
—— 2-(1-Hydroxybut-3-enyl)-6-methylphenol 1000781-20-3 C11H14O2
2-(1-Hydroxybut-3-enyl)-6-methylphenol
—— 4-(6-hydroxy-5,7,8-trimethyl-2,3-dihydrobenzo[b][1,4]-oxathiin-2-yl)benzene-1,2-diol 958463-30-4 C17H18O4S
4-(6-hydroxy-5,7,8-trimethyl-2,3-dihydrobenzo[b][1,4]-oxathiin-2-yl)benzene-1,2-diol
—— aleurodisconitrile 1000180-33-5 C13H16N2O6
aleurodisconitrile
—— 3-Methoxy-2-methyl-6-(3-methylbut-2-enyl)phenol 1006054-43-8 C13H18O2
3-Methoxy-2-methyl-6-(3-methylbut-2-enyl)phenol
—— 3-Methoxy-2-methyl-4,6-bis(3-methylbut-2-enyl)phenol 1006054-48-3 C18H26O2
3-Methoxy-2-methyl-4,6-bis(3-methylbut-2-enyl)phenol
—— 29,35,41,46-Tetratert-butyl-3,11,14,17,25-pentaoxa-6,7,8,20,21,22-hexazaoctacyclo[25.15.7.15,8.120,23.133,37.144,48.02,39.026,31]tripentaconta-1,5(53),6,21,23(52),26,28,30,33(51),34,36,39,41,44,46,48(50)-hexadecaene-50,51-diol 1159490-23-9 C58H76N6O7
29,35,41,46-Tetratert-butyl-3,11,14,17,25-pentaoxa-6,7,8,20,21,22-hexazaoctacyclo[25.15.7.15,8.120,23.133,37.144,48.02,39.026,31]tripentaconta-1,5(53),6,21,23(52),26,28,30,33(51),34,36,39,41,44,46,48(50)-hexadecaene-50,51-diol