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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-[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
—— tris(4-hydroxyphenyl)bismuth dichloride 214407-14-4 C18H15BiCl2O3
tris(4-hydroxyphenyl)bismuth dichloride
—— tris(3-hydroxyphenyl)bismuth dichloride 214407-13-3 C18H15BiCl2O3
tris(3-hydroxyphenyl)bismuth dichloride
—— tris(2-hydroxyphenyl)bismuth dichloride 214407-11-1 C18H15BiCl2O3
tris(2-hydroxyphenyl)bismuth dichloride
—— 2-(2-benzofuranyl)-2-(4-hydroxy-3-methoxyphenyl)-1-nitroethane 1079360-68-1 C17H15NO5
2-(2-benzofuranyl)-2-(4-hydroxy-3-methoxyphenyl)-1-nitroethane
—— Potassium guaiacolsulfonate 7134-11-4 C7H9KO6S
Potassium guaiacolsulfonate
—— Benzamide, 2-hydroxy-N-(1-methyl-1H-1,2,4-triazol-5-yl)-3-nitro- 1913000-00-6 C10H9N5O4
Benzamide, 2-hydroxy-N-(1-methyl-1H-1,2,4-triazol-5-yl)-3-nitro-
—— 5-(Aminomethyl)-2-fluorophenol hydrochloride 2044704-82-5 C7H9ClFNO
5-(Aminomethyl)-2-fluorophenol hydrochloride
—— 2-[4-(2-Hydroxyethyl)phenoxy]acetamide 173436-10-7 C10H13NO3
2-[4-(2-Hydroxyethyl)phenoxy]acetamide
—— I+/-,4-Dihydroxybenzenemethanesulfonic acid 732937-24-5 C7H8O5S
I+/-,4-Dihydroxybenzenemethanesulfonic acid
—— Ethyl 78-hydroxy-17,56-dioxaoctacyclo[61.2.2.27,10.213,16.231,34.239,42.257,60.12,6]octaheptaconta-1(65),2(78),3,5,7(77),8,10(76),13(75),14,16(74),31(73),32,34(72),39,41,57,59,63,66,68,70-henicosaen-11,29,35,37,43,61-hexayne-4-carboxylate 499138-73-7 C79H76O5
Ethyl 78-hydroxy-17,56-dioxaoctacyclo[61.2.2.27,10.213,16.231,34.239,42.257,60.12,6]octaheptaconta-1(65),2(78),3,5,7(77),8,10(76),13(75),14,16(74),31(73),32,34(72),39,41,57,59,63,66,68,70-henicosaen-11,29,35,37,43,61-hexayne-4-carboxylate
—— Azanium;2-methyl-3,5-dinitrophenol —— C7H10N3O5+
Azanium;2-methyl-3,5-dinitrophenol
—— 3-Bromo-4-(3,5-dibromo-2-hydroxyphenyl)pyrrole-2,5-dione 1364322-53-1 C10H4Br3NO3
3-Bromo-4-(3,5-dibromo-2-hydroxyphenyl)pyrrole-2,5-dione
—— 2-[(Z)-hex-2-enyl]phenol 1272609-91-2 C12H16O
2-[(Z)-hex-2-enyl]phenol
—— methyl 11-(4-hydroxy-3,5-dimethylphenyl)undecanoate 1015699-45-2 C20H32O3
methyl 11-(4-hydroxy-3,5-dimethylphenyl)undecanoate
—— 3-(2-chloro-4-hydroxyphenylethynyl)-2-methylcyclohex-2-enone 1037717-32-0 C15H13ClO2
3-(2-chloro-4-hydroxyphenylethynyl)-2-methylcyclohex-2-enone
—— N-[[4-hydroxy-3,5-bis[[8-(3-octyloxiran-2-yl)octanoylamino]methyl]phenyl]methyl]-8-(3-octyloxiran-2-yl)octanamide 1335416-41-5 C63H111N3O7
N-[[4-hydroxy-3,5-bis[[8-(3-octyloxiran-2-yl)octanoylamino]methyl]phenyl]methyl]-8-(3-octyloxiran-2-yl)octanamide
—— 1323355-85-6 C15H16NO2
—— 4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde 55525-45-6 C16H16O5
4-((4-hydroxy-3-methoxybenzyl)oxy)-3-methoxybenzaldehyde
—— 4-Hydroxy-3-methoxy-2-methylsulfanylbenzonitrile 1245744-69-7 C9H9NO2S
4-Hydroxy-3-methoxy-2-methylsulfanylbenzonitrile
—— 24,30,36,41-Tetratert-butyl-45,46-dihydroxy-6,17-bis(2-hydroxyethyl)-3,20-dioxa-6,8,15,17-tetrazahexacyclo[20.15.7.128,32.139,43.02,34.021,26]hexatetraconta-1,21,23,25,28(46),29,31,34,36,39,41,43(45)-dodecaene-7,16-dione 1251829-60-3 C60H86N4O8
24,30,36,41-Tetratert-butyl-45,46-dihydroxy-6,17-bis(2-hydroxyethyl)-3,20-dioxa-6,8,15,17-tetrazahexacyclo[20.15.7.128,32.139,43.02,34.021,26]hexatetraconta-1,21,23,25,28(46),29,31,34,36,39,41,43(45)-dodecaene-7,16-dione