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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
—— (S)-2-(1-aminobutyl)phenol 1213572-94-1 C10H15NO
(S)-2-(1-aminobutyl)phenol
—— Calcium;2-hydroxy-2-(4-hydroxyphenyl)acetate —— C16H14CaO8
Calcium;2-hydroxy-2-(4-hydroxyphenyl)acetate
—— Sodium 4-(2-hydroxy-2-sulfopropyl)-2-methoxyphenolate 83682-27-3 C10H13NaO6S
Sodium 4-(2-hydroxy-2-sulfopropyl)-2-methoxyphenolate
—— Antibiotic FA 2097 81988-71-8 C21H22N2O8S2
Antibiotic FA 2097
—— 3-[3,5-Bis[2-[3,4-bis[2-(3,4-didodecoxyphenyl)ethoxy]phenyl]ethoxy]phenoxy]propan-1-amine 1352994-19-4 C153H253NO15
3-[3,5-Bis[2-[3,4-bis[2-(3,4-didodecoxyphenyl)ethoxy]phenyl]ethoxy]phenoxy]propan-1-amine
—— 2-(1-bromo-2-hydroxypent-4-en-2-yl)phenol 1450629-56-7 C11H13BrO2
2-(1-bromo-2-hydroxypent-4-en-2-yl)phenol
—— (2S,8R,14R,20S)-5-(2-hydroxyethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[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-4,6,10,12,16,18,22,24-octol 1469921-84-3 C47H62O10
(2S,8R,14R,20S)-5-(2-hydroxyethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[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-4,6,10,12,16,18,22,24-octol
—— 5,35-Dibromo-9,14,19,24,26,28,30,32-octamethoxyhexacyclo[21.2.2.23,6.28,11.213,16.218,21]pentatriaconta-1(26),3,5,8,10,13,15,18(29),19,21(28),23(27),24,30,32,34-pentadecaene-4,34-diol 1616090-12-0 C43H44Br2O10
5,35-Dibromo-9,14,19,24,26,28,30,32-octamethoxyhexacyclo[21.2.2.23,6.28,11.213,16.218,21]pentatriaconta-1(26),3,5,8,10,13,15,18(29),19,21(28),23(27),24,30,32,34-pentadecaene-4,34-diol
—— (2S,8R,14S,20R)-2,8,14,20-tetrakis(2-methylpropyl)-5,17-bis(propoxymethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 1469921-88-7 C52H72O10
(2S,8R,14S,20R)-2,8,14,20-tetrakis(2-methylpropyl)-5,17-bis(propoxymethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— (2S,8R,14R,20S)-5-(ethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[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-4,6,10,12,16,18,22,24-octol 1469921-78-5 C47H62O9
(2S,8R,14R,20S)-5-(ethoxymethyl)-2,8,14,20-tetrakis(2-methylpropyl)pentacyclo[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-4,6,10,12,16,18,22,24-octol
—— 2-(hydroxy(methyl)arsino)-4-methylphenol 1584642-20-5 C8H11AsO2
2-(hydroxy(methyl)arsino)-4-methylphenol
—— 2-[2-Hydroxyethylsulfanyl(methyl)arsanyl]-4-methylphenol 1584642-19-2 C10H15AsO2S
2-[2-Hydroxyethylsulfanyl(methyl)arsanyl]-4-methylphenol
—— 4-(2-Hydroxyphenyl)nonan-2-one 1421016-47-8 C15H22O2
4-(2-Hydroxyphenyl)nonan-2-one
—— 3,9,15,32-Tetratert-butyl-36,37-dihydroxy-19,27-dioxahexacyclo[15.11.7.17,11.130,34.05,28.013,18]heptatriaconta-1,3,5(28),7,9,11(37),13(18),14,16,30,32,34(36)-dodecaene-23,23-dicarbonitrile 1207339-18-1 C53H66N2O4
3,9,15,32-Tetratert-butyl-36,37-dihydroxy-19,27-dioxahexacyclo[15.11.7.17,11.130,34.05,28.013,18]heptatriaconta-1,3,5(28),7,9,11(37),13(18),14,16,30,32,34(36)-dodecaene-23,23-dicarbonitrile
—— 3,9,15,34-Tetratert-butyl-38,39-dihydroxy-19,29-dioxahexacyclo[15.13.7.17,11.132,36.05,30.013,18]nonatriaconta-1,3,5(30),7,9,11(39),13(18),14,16,32,34,36(38)-dodecaene-24,24-dicarbonitrile 1207339-19-2 C55H70N2O4
3,9,15,34-Tetratert-butyl-38,39-dihydroxy-19,29-dioxahexacyclo[15.13.7.17,11.132,36.05,30.013,18]nonatriaconta-1,3,5(30),7,9,11(39),13(18),14,16,32,34,36(38)-dodecaene-24,24-dicarbonitrile
—— (E,E)-[[fiethyl 2,2'-[4,5-dihydroxy-1,2-phenylenebis(iminomethylidyne)]bis(3-oxobutanoate)]] 1229042-11-8 C20H24N2O8
(E,E)-[[fiethyl 2,2'-[4,5-dihydroxy-1,2-phenylenebis(iminomethylidyne)]bis(3-oxobutanoate)]]
—— 2-(4-Phenylmethoxyphenyl)ethyl acetate 99624-71-2 C17H18O3
2-(4-Phenylmethoxyphenyl)ethyl acetate
—— 3-[5-[2-Hydroxy-2-(3-hydroxyphenyl)ethyl]-3-pent-4-enylfuran-2-yl]phenol 1204300-08-2 C23H24O4
3-[5-[2-Hydroxy-2-(3-hydroxyphenyl)ethyl]-3-pent-4-enylfuran-2-yl]phenol
—— 2-[[(2-Hydroxy-3-methoxy-5-methylphenyl)methyl-(2-morpholin-4-ylethyl)amino]methyl]-6-methoxy-4-methylphenol 1421471-12-6 C24H34N2O5
2-[[(2-Hydroxy-3-methoxy-5-methylphenyl)methyl-(2-morpholin-4-ylethyl)amino]methyl]-6-methoxy-4-methylphenol
—— (E)-4-(5-bromo-2-nitropent-1-enyl)phenol 1426535-49-0 C11H12BrNO3
(E)-4-(5-bromo-2-nitropent-1-enyl)phenol
—— 4-[4-[Bis(ethenyl)-methylsilyl]butoxy]phenol 1426827-50-0 C15H22O2Si
4-[4-[Bis(ethenyl)-methylsilyl]butoxy]phenol
—— 3-allyl-2-bromo-6-methoxyphenol 1448888-84-3 C10H11BrO2
3-allyl-2-bromo-6-methoxyphenol
—— 2-amino-5-(2-hydroxyphenyl)-1,3-thiazol-4(5H)-one 1628629-57-1 C9H8N2O2S
2-amino-5-(2-hydroxyphenyl)-1,3-thiazol-4(5H)-one
—— 5-(2-Hydroxyphenyl)-2-methylimino-1,3-thiazolidin-4-one 1628629-68-4 C10H10N2O2S
5-(2-Hydroxyphenyl)-2-methylimino-1,3-thiazolidin-4-one
—— 2-(2-hydroxyphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3(2H)-one 1644489-85-9 C11H10N2O2S
2-(2-hydroxyphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3(2H)-one
—— 4-Chloro-2-hydroxy-3,5-dinitrobenzoic acid 16308-97-7 C7H3ClN2O7
4-Chloro-2-hydroxy-3,5-dinitrobenzoic acid
—— 5,11,31,37-Tetratert-butyl-47-hydroxy-15,27,40-trioxa-18,21,24,43-tetrazaheptacyclo[19.17.7.13,7.113,29.09,14.028,33.035,39]heptatetraconta-1(39),3,5,7(47),9(14),10,12,28,30,32,35,37-dodecaene-17,25,42-trione 340155-44-4 C56H74N4O7
5,11,31,37-Tetratert-butyl-47-hydroxy-15,27,40-trioxa-18,21,24,43-tetrazaheptacyclo[19.17.7.13,7.113,29.09,14.028,33.035,39]heptatetraconta-1(39),3,5,7(47),9(14),10,12,28,30,32,35,37-dodecaene-17,25,42-trione
—— 1-[4-(2-Methoxyethyl)phenoxy]-3-phenylsulfanylpropan-2-ol 934538-08-6 C18H22O3S
1-[4-(2-Methoxyethyl)phenoxy]-3-phenylsulfanylpropan-2-ol
—— N-[3-(4-hydroxyphenyl)propyl]-1-methylsulfonylmethanesulfonamide 1261033-60-6 C11H17NO5S2
N-[3-(4-hydroxyphenyl)propyl]-1-methylsulfonylmethanesulfonamide
—— 1,1,1-trifluoro-N-[3-(4-hydroxyphenyl)propyl]methanesulfonamide 1261033-57-1 C10H12F3NO3S
1,1,1-trifluoro-N-[3-(4-hydroxyphenyl)propyl]methanesulfonamide
—— 6,12-Dioxido-6,12-diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol 1254578-48-7 C72H62O10P2
6,12-Dioxido-6,12-diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol
—— 6,12-Diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol 1254581-02-6 C72H62O8P2S2
6,12-Diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol
—— 22,28,34,39-Tetratert-butyl-43,44-dihydroxy-3,18-dioxa-6,9,12,15-tetrazahexacyclo[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 136158-04-8 C54H74N4O6
22,28,34,39-Tetratert-butyl-43,44-dihydroxy-3,18-dioxa-6,9,12,15-tetrazahexacyclo[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
—— (1R,12S,14R,17R,19R,20S)-5-hydroxy-17-phenyl-20-trimethylsilyloxy-2,13,16,18-tetraoxa-11-thiatetracyclo[10.8.0.04,9.014,19]icosa-4(9),5,7-trien-3-one 1119020-32-4 C24H28O7SSi
(1R,12S,14R,17R,19R,20S)-5-hydroxy-17-phenyl-20-trimethylsilyloxy-2,13,16,18-tetraoxa-11-thiatetracyclo[10.8.0.04,9.014,19]icosa-4(9),5,7-trien-3-one
—— (1R,12S,14R,17R,19S,20S)-5,20-dihydroxy-17-phenyl-2,13,16,18-tetraoxa-11-thiatetracyclo[10.8.0.04,9.014,19]icosa-4(9),5,7-trien-3-one 1119020-25-5 C21H20O7S
(1R,12S,14R,17R,19S,20S)-5,20-dihydroxy-17-phenyl-2,13,16,18-tetraoxa-11-thiatetracyclo[10.8.0.04,9.014,19]icosa-4(9),5,7-trien-3-one
—— 2-Bromo-4-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-6-trimethylsilylphenol 1127943-10-5 C27H35BrO2Si2
2-Bromo-4-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-6-trimethylsilylphenol
—— Tridecacyclo[35.23.5.57,31.516,52.522,46.12,6.117,21.132,36.147,51.161,65.167,71.173,77.179,83]octaoctaconta-2(85),3,5,17(84),18,20,32,34,36(78),47,49,51(72),61(66),62,64,67(88),68,70,73(87),74,76,79,81,83(86)-tetracosaene-3,5,18,20,33,35,48,50,62,64,68,70,74,76,80,82-hexadecol 1393888-65-7 C88H104O16
Tridecacyclo[35.23.5.57,31.516,52.522,46.12,6.117,21.132,36.147,51.161,65.167,71.173,77.179,83]octaoctaconta-2(85),3,5,17(84),18,20,32,34,36(78),47,49,51(72),61(66),62,64,67(88),68,70,73(87),74,76,79,81,83(86)-tetracosaene-3,5,18,20,33,35,48,50,62,64,68,70,74,76,80,82-hexadecol
—— 1,4-bis(3,5-dihydroxyphenyl)-2,3-diphenyl-9H-tribenzo[a,c,e]cycloheptene 1393486-83-3 C43H30O4
1,4-bis(3,5-dihydroxyphenyl)-2,3-diphenyl-9H-tribenzo[a,c,e]cycloheptene
—— (E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(furan-2-yl)prop-2-en-1-one 1394173-52-4 C15H13BrO5
(E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(furan-2-yl)prop-2-en-1-one
—— Tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol 1393888-62-4 C72H72O16
Tridecacyclo[27.17.5.56,24.412,41.418,35.17,11.113,17.119,23.130,34.136,40.142,46.147,51.164,68]doheptaconta-7(71),8,10,13(70),14,16,19,21,23(69),30(63),31,33,36,38,40(58),42,44,46(53),47(52),48,50,64,66,68(72)-tetracosaene-8,10,14,16,20,22,31,33,37,39,43,45,48,50,65,67-hexadecol
—— (5S,19S)-25-bromo-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-ol 946533-37-5 C32H39BrO8
(5S,19S)-25-bromo-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-trien-27-ol
—— (R)-10-hydroxy-5-phenyl-1H-oxazolo[4,3-a]isoquinolin-3(10bH)-one 1410748-22-9 C17H13NO3
(R)-10-hydroxy-5-phenyl-1H-oxazolo[4,3-a]isoquinolin-3(10bH)-one
—— 2-[[2-[[2-[(2-Hydroxyphenyl)iminomethyl]phenyl]diselanyl]phenyl]methylideneamino]phenol 1401244-81-2 C26H20N2O2Se2
2-[[2-[[2-[(2-Hydroxyphenyl)iminomethyl]phenyl]diselanyl]phenyl]methylideneamino]phenol
—— 2-[4-(2-Hydroxy-5-methylphenyl)-1,4-diazepan-1-yl]-4-methylphenol 1412448-77-1 C19H24N2O2
2-[4-(2-Hydroxy-5-methylphenyl)-1,4-diazepan-1-yl]-4-methylphenol
—— (R)-5-bromo-10-hydroxy-1H-oxazolo[4,3-a]isoquinolin-3(10bH)-one 1410748-32-1 C11H8BrNO3
(R)-5-bromo-10-hydroxy-1H-oxazolo[4,3-a]isoquinolin-3(10bH)-one
—— 2-(2,4-Dihydroxy-6-methylphenyl)cyclohexa-2,5-diene-1,4-dione 1522080-19-8 C13H10O4
2-(2,4-Dihydroxy-6-methylphenyl)cyclohexa-2,5-diene-1,4-dione
—— 5-(12-Nonadecenyl)resorcinol 189562-06-9 C25H42O2
5-(12-Nonadecenyl)resorcinol
—— 6-methoxy-1-{[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylenedecahydronaphthalen-1-yl]methyl}benzene-2,3-diol 1070795-50-4 C22H32O3
6-methoxy-1-{[(1R,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylenedecahydronaphthalen-1-yl]methyl}benzene-2,3-diol
—— (4-hydroxy-3-methoxyphenyl)-bis(2-benzofuranyl)methane 1079360-28-3 C24H18O4
(4-hydroxy-3-methoxyphenyl)-bis(2-benzofuranyl)methane
—— tris(3-hydroxyphenyl)bismuthane 214407-16-6 C18H15BiO3
tris(3-hydroxyphenyl)bismuthane