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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
—— 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
—— 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