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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
—— 23,29,35,40-Tetratert-butyl-3,11,19-trioxa-6,7,8,14,15,16-hexazaoctacyclo[19.15.7.15,8.114,17.127,31.138,42.02,33.020,25]heptatetraconta-1,5(47),6,15,17(46),20,22,24,27(45),28,30,33,35,38,40,42(44)-hexadecaene-44,45-diol 1159490-21-7 C54H68N6O5
23,29,35,40-Tetratert-butyl-3,11,19-trioxa-6,7,8,14,15,16-hexazaoctacyclo[19.15.7.15,8.114,17.127,31.138,42.02,33.020,25]heptatetraconta-1,5(47),6,15,17(46),20,22,24,27(45),28,30,33,35,38,40,42(44)-hexadecaene-44,45-diol
—— 26,32,38,43-Tetratert-butyl-3,11,14,22-tetraoxa-6,7,8,17,18,19-hexazaoctacyclo[22.15.7.15,8.117,20.130,34.141,45.02,36.023,28]pentaconta-1,5(50),6,18,20(49),23,25,27,30(48),31,33,36,38,41,43,45(47)-hexadecaene-47,48-diol 1159490-22-8 C56H72N6O6
26,32,38,43-Tetratert-butyl-3,11,14,22-tetraoxa-6,7,8,17,18,19-hexazaoctacyclo[22.15.7.15,8.117,20.130,34.141,45.02,36.023,28]pentaconta-1,5(50),6,18,20(49),23,25,27,30(48),31,33,36,38,41,43,45(47)-hexadecaene-47,48-diol
—— 30,36,42,47-Tetratert-butyl-3,11,18,26-tetraoxa-6,7,8,21,22,23-hexazanonacyclo[26.15.7.15,8.121,24.134,38.145,49.02,40.012,17.027,32]tetrapentaconta-1,5(54),6,12,14,16,22,24(53),27,29,31,34(52),35,37,40,42,45,47,49(51)-nonadecaene-51,52-diol 1159490-26-2 C60H72N6O6
30,36,42,47-Tetratert-butyl-3,11,18,26-tetraoxa-6,7,8,21,22,23-hexazanonacyclo[26.15.7.15,8.121,24.134,38.145,49.02,40.012,17.027,32]tetrapentaconta-1,5(54),6,12,14,16,22,24(53),27,29,31,34(52),35,37,40,42,45,47,49(51)-nonadecaene-51,52-diol
—— 2,7,13,18-tetramethyl-3,6,14,17-tetraazatricyclo-[17.3.1.1]-tetracosa-1(23),8(24),9,11,19,21-hexane-9,11,20,22-tetraol 1178976-24-3 C24H36N4O4
2,7,13,18-tetramethyl-3,6,14,17-tetraazatricyclo-[17.3.1.1]-tetracosa-1(23),8(24),9,11,19,21-hexane-9,11,20,22-tetraol
—— 3,11-dihydroxy-6,7,8,9-tetrahydro-5H-dibenzo[a,c]cyclononene 1214891-29-8 C17H18O2
3,11-dihydroxy-6,7,8,9-tetrahydro-5H-dibenzo[a,c]cyclononene
—— o-HO-C6H4NHC(S)NHP(S)(OiPr)2 1217089-27-4 C13H21N2O3PS2
o-HO-C6H4NHC(S)NHP(S)(OiPr)2
—— 5,11,17,23-Tetratert-butyl-2,8,14,20-tetraoxa-4,6,16,18,26,28-hexazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-25,27-diol 1254977-01-9 C34H42N6O6
5,11,17,23-Tetratert-butyl-2,8,14,20-tetraoxa-4,6,16,18,26,28-hexazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-25,27-diol
—— (5-(4-hydroxyphenethyl)furan-2,4-diyl)dimethanol 1240715-26-7 C14H16O4
(5-(4-hydroxyphenethyl)furan-2,4-diyl)dimethanol
—— 5-(16-Heneicosenyl)-1,3-benzenediol 189562-08-1 C27H46O2
5-(16-Heneicosenyl)-1,3-benzenediol
—— 5-(14-Nonadecenyl)-1,3-benzenediol 187523-39-3 C25H42O2
5-(14-Nonadecenyl)-1,3-benzenediol
—— 33,39,45,50-Tetratert-butyl-54,55-dihydroxy-3,29-dioxa-6,7,8,12,20,24,25,26-octazanonacyclo[29.15.7.15,8.114,18.124,27.137,41.148,52.02,43.030,35]octapentaconta-1,5(58),6,14,16,18(57),25,27(56),30,32,34,37(55),38,40,43,45,48,50,52(54)-nonadecaene-13,19-dione 1388681-37-5 C64H78N8O6
33,39,45,50-Tetratert-butyl-54,55-dihydroxy-3,29-dioxa-6,7,8,12,20,24,25,26-octazanonacyclo[29.15.7.15,8.114,18.124,27.137,41.148,52.02,43.030,35]octapentaconta-1,5(58),6,14,16,18(57),25,27(56),30,32,34,37(55),38,40,43,45,48,50,52(54)-nonadecaene-13,19-dione
—— 4-Nitro-2-(2-nitro-benzenesulfonyl)-phenol 133826-86-5 C12H8N2O7S
4-Nitro-2-(2-nitro-benzenesulfonyl)-phenol
—— 11,23-Di-tert-butyl-5,17-diethoxycarbonyl-25,26,27,28-tetrahydroxycalix<4>arene 133908-49-3 C42H48O8
11,23-Di-tert-butyl-5,17-diethoxycarbonyl-25,26,27,28-tetrahydroxycalix<4>arene
—— 2-(1,2-Diamino-1-propenyl)phenol 173559-57-4 C9H12N2O
2-(1,2-Diamino-1-propenyl)phenol
—— 21,27,33,38-Tetratert-butyl-42,43-dihydroxy-3,17-dioxa-6,10,14-triazahexacyclo[17.15.7.125,29.136,40.02,31.018,23]tritetraconta-1,18,20,22,25(43),26,28,31,33,36,38,40(42)-dodecaene-5,15-dione 136158-05-9 C54H73N3O6
21,27,33,38-Tetratert-butyl-42,43-dihydroxy-3,17-dioxa-6,10,14-triazahexacyclo[17.15.7.125,29.136,40.02,31.018,23]tritetraconta-1,18,20,22,25(43),26,28,31,33,36,38,40(42)-dodecaene-5,15-dione
—— 5-(1-Butyl-pentyl)-benzene-1,3-diol 50833-16-4 C15H24O2
5-(1-Butyl-pentyl)-benzene-1,3-diol
—— N-((1S,2S)-1-Diethoxymethyl-2-methyl-butyl)-3-hydroxy-2-methoxy-N-methyl-benzamide 866528-85-0 C19H31NO5
N-((1S,2S)-1-Diethoxymethyl-2-methyl-butyl)-3-hydroxy-2-methoxy-N-methyl-benzamide
—— 1,3-Alternate-thiacalix[4]-m-benzocrown-4 1264481-66-4 C50H58O6S4
1,3-Alternate-thiacalix[4]-m-benzocrown-4
—— 3-bromo-4-(phenylselenyl)phenol 1350814-90-2 C12H9BrOSe
3-bromo-4-(phenylselenyl)phenol
—— 2-[(Z)-hex-2-enyl]-6-methylphenol 1272609-92-3 C13H18O
2-[(Z)-hex-2-enyl]-6-methylphenol
—— 4-bromo-2-[(Z)-hex-2-enyl]phenol 1272609-93-4 C12H15BrO
4-bromo-2-[(Z)-hex-2-enyl]phenol
—— 2-[(E)-hex-2-enyl]-6-methylphenol 1272609-97-8 C13H18O
2-[(E)-hex-2-enyl]-6-methylphenol
—— [4-(2-Hydroxyethyl)phenyl] 2,2,2-trichloroethyl sulfate 1313434-31-9 C10H11Cl3O5S
[4-(2-Hydroxyethyl)phenyl] 2,2,2-trichloroethyl sulfate
—— 4-dimethylaminomethyl-resorcinol 86198-30-3 C9H13NO2
4-dimethylaminomethyl-resorcinol
—— 4-(2-chloroethyl)-3,5-dimethylphenol 1020666-84-5 C10H13ClO
4-(2-chloroethyl)-3,5-dimethylphenol
—— 4-(3-hydroxy-2-methoxy-6-methylphenyl)butanal 1029654-60-1 C12H16O3
4-(3-hydroxy-2-methoxy-6-methylphenyl)butanal
—— 3-(4-hydroxyphenylethynyl)-2-methylcyclopent-2-enol 1037717-33-1 C14H14O2
3-(4-hydroxyphenylethynyl)-2-methylcyclopent-2-enol
—— 3-(4-hydroxyphenylethynyl)-2-methylcyclopent-2-enone 1037717-41-1 C14H12O2
3-(4-hydroxyphenylethynyl)-2-methylcyclopent-2-enone
—— 3-(2-chloro-4-hydroxyphenylethynyl)-2-ethylcyclopent-2-enone 1037717-39-7 C15H13ClO2
3-(2-chloro-4-hydroxyphenylethynyl)-2-ethylcyclopent-2-enone
—— (S)-3-propanoyl-4-(4'-hydroxybenzyl)-5,5-dimethyloxazolidin-2-one 1033132-64-7 C15H19NO4
(S)-3-propanoyl-4-(4'-hydroxybenzyl)-5,5-dimethyloxazolidin-2-one
—— β-(2-methoxyphenoxy)coniferyl alcohol 146252-23-5 C17H18O5
β-(2-methoxyphenoxy)coniferyl alcohol
—— Potassium 3-acetylaminophenolate 76506-19-9 C8H8NO2*K
Potassium 3-acetylaminophenolate
—— 4-[2-[2-[2-(4-Hydroxy-3-prop-2-enylphenoxy)ethoxy]ethoxy]ethoxy]-2-prop-2-enylphenol 1619989-78-4 C24H30O6
4-[2-[2-[2-(4-Hydroxy-3-prop-2-enylphenoxy)ethoxy]ethoxy]ethoxy]-2-prop-2-enylphenol
—— 5-(3-Amino-4-methylanilino)-2,4-dinitrophenol 1314491-05-8 C13H12N4O5
5-(3-Amino-4-methylanilino)-2,4-dinitrophenol
—— 5-(2-Hydroxyethyl)-2-phenylmethoxyphenol 1333081-72-3 C15H16O3
5-(2-Hydroxyethyl)-2-phenylmethoxyphenol
—— 5-[(3R)-3-aminobutyl]-2-methoxyphenol 1335234-94-0 C11H17NO2
5-[(3R)-3-aminobutyl]-2-methoxyphenol
—— tert-butyl (1R,2R)-2-hydroxy-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate 1334227-86-9 C16H23NO6
tert-butyl (1R,2R)-2-hydroxy-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate
—— 4-O-Benzyl-3-hydroxy Tyrosol a-Acetate 1333081-71-2 C17H18O4
4-O-Benzyl-3-hydroxy Tyrosol a-Acetate
—— (Z)-N-[[4-hydroxy-3,5-bis[[[(Z)-octadec-9-enoyl]amino]methyl]phenyl]methyl]octadec-9-enamide 1335416-32-4 C63H111N3O4
(Z)-N-[[4-hydroxy-3,5-bis[[[(Z)-octadec-9-enoyl]amino]methyl]phenyl]methyl]octadec-9-enamide
—— N-(4-hydroxybenzyl)oleamide 1335416-46-0 C25H41NO2
N-(4-hydroxybenzyl)oleamide
—— Heptacyclo[21.9.4.47,17.13,31.15,9.115,19.121,25]tetratetraconta-1,3(37),5(44),6,8,15,17,19(39),21(38),22,24,31-dodecaene-2,6,18,22-tetrol 152266-16-5 C44H52O4
Heptacyclo[21.9.4.47,17.13,31.15,9.115,19.121,25]tetratetraconta-1,3(37),5(44),6,8,15,17,19(39),21(38),22,24,31-dodecaene-2,6,18,22-tetrol
—— 2-chloro-N-[[3-[[(2-chloroacetyl)amino]methyl]-4-hydroxyphenyl]methyl]acetamide 1335416-28-8 C12H14Cl2N2O3
2-chloro-N-[[3-[[(2-chloroacetyl)amino]methyl]-4-hydroxyphenyl]methyl]acetamide
—— 3-ethyl-6,7,8,9,10,11-hexahydro-5H-benzo[9]annulen-4-ol 1100054-91-8 C15H22O
3-ethyl-6,7,8,9,10,11-hexahydro-5H-benzo[9]annulen-4-ol
—— 7-Methyl-8,9-dihydrobenzo[7]annulene-3,7-diol 1138003-70-9 C12H14O2
7-Methyl-8,9-dihydrobenzo[7]annulene-3,7-diol
—— 7-Methyl-5,6,8,9-tetrahydrobenzo[7]annulene-3,7-diol 1138003-72-1 C12H16O2
7-Methyl-5,6,8,9-tetrahydrobenzo[7]annulene-3,7-diol
—— 23,29,35,40-Tetratert-butyl-44,45-dihydroxy-3,19-dioxa-6,9,13,16-tetrazahexacyclo[19.15.7.127,31.138,42.02,33.020,25]pentatetraconta-1,20,22,24,27(45),28,30,33,35,38,40,42(44)-dodecaene-5,17-dione 1118429-93-8 C55H76N4O6
23,29,35,40-Tetratert-butyl-44,45-dihydroxy-3,19-dioxa-6,9,13,16-tetrazahexacyclo[19.15.7.127,31.138,42.02,33.020,25]pentatetraconta-1,20,22,24,27(45),28,30,33,35,38,40,42(44)-dodecaene-5,17-dione
—— 115780-42-2 C9H12NO3
—— 2,6-diethynyl-4-methylphenol 1245255-95-1 C11H8O
2,6-diethynyl-4-methylphenol
—— 2-(4-Hydroxy-3-methoxyphenyl)-1,3-oxathiolan-5-one 1258876-46-8 C10H10O4S
2-(4-Hydroxy-3-methoxyphenyl)-1,3-oxathiolan-5-one
—— (S)-2-(1-aminoheptyl)phenol 1247949-52-5 C13H21NO
(S)-2-(1-aminoheptyl)phenol