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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
—— 2-(2,3,5-trimethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one 180090-39-5 C15H21NO3S
2-(2,3,5-trimethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
—— 25,27-bis(dimethylcarbamoyloxy)-26,28-dihydroxycalix[4]arene 261639-37-6 C34H34N2O6
25,27-bis(dimethylcarbamoyloxy)-26,28-dihydroxycalix[4]arene
—— 2-Heptadecyl-3,5-dimethoxy-phenol 148665-85-4 C25H44O3
2-Heptadecyl-3,5-dimethoxy-phenol
—— 2-chloro-5-methoxy-3,4-dimethylphenol 182010-46-4 C9H11ClO2
2-chloro-5-methoxy-3,4-dimethylphenol
—— 2-(4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one 180090-37-3 C12H15NO3S
2-(4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
—— 2-fluoro-5-methoxy-3,4-dimethyl-6-(2-propenyl)phenol 182010-44-2 C12H15FO2
2-fluoro-5-methoxy-3,4-dimethyl-6-(2-propenyl)phenol
—— 2-(2,3,5-trimethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-55-5 C15H20ClNO2S
2-(2,3,5-trimethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— methyl (E)-6-(2-chloro-3-hydroxy-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate 182011-27-4 C17H23ClO4
methyl (E)-6-(2-chloro-3-hydroxy-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate
—— (3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-4-nitro-phenylamino)-hexa-3,5-dien-2-one 196078-61-2 C14H14F3N3O4
(3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-4-nitro-phenylamino)-hexa-3,5-dien-2-one
—— 5,11,17,23,29,35,41,47-Octatert-butyl-50,53-dioxadecacyclo[23.23.6.13,7.19,13.115,19.127,31.133,37.139,43.021,54.045,49]hexaconta-1(48),3,5,7(60),9,11,13(59),15(58),16,18,21,23,25(54),27,29,31(57),33(56),34,36,39(55),40,42,45(49),46-tetracosaene-55,56,57,58,59,60-hexol 287199-33-1 C90H114O8
5,11,17,23,29,35,41,47-Octatert-butyl-50,53-dioxadecacyclo[23.23.6.13,7.19,13.115,19.127,31.133,37.139,43.021,54.045,49]hexaconta-1(48),3,5,7(60),9,11,13(59),15(58),16,18,21,23,25(54),27,29,31(57),33(56),34,36,39(55),40,42,45(49),46-tetracosaene-55,56,57,58,59,60-hexol
—— 5,11,17,23-Tetrabromo-2,8,14,20-tetrakis(4-hydroxybutyl)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 174358-74-8 C44H52Br4O12
5,11,17,23-Tetrabromo-2,8,14,20-tetrakis(4-hydroxybutyl)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
—— (Z)-1,1,1-Trifluoro-4-(2-hydroxy-4-methyl-phenylamino)-pent-3-en-2-one 196078-52-1 C12H12F3NO2
(Z)-1,1,1-Trifluoro-4-(2-hydroxy-4-methyl-phenylamino)-pent-3-en-2-one
—— 4-chloro-2,3,5-trimethyl-6-(2-propenyl)phenol 182011-31-0 C12H15ClO
4-chloro-2,3,5-trimethyl-6-(2-propenyl)phenol
—— [1-Fluoro-2-(3-hydroxy-phenyl)-ethyl]-phosphonic acid diethyl ester 209120-15-0 C12H18FO4P
[1-Fluoro-2-(3-hydroxy-phenyl)-ethyl]-phosphonic acid diethyl ester
—— (3Z,5E)-4-(5-Chloro-2-hydroxy-phenylamino)-6-dimethylamino-1,1,1-trifluoro-hexa-3,5-dien-2-one 196078-59-8 C14H14ClF3N2O2
(3Z,5E)-4-(5-Chloro-2-hydroxy-phenylamino)-6-dimethylamino-1,1,1-trifluoro-hexa-3,5-dien-2-one
—— p-tert-butylcalix<4>crown 225507-06-2 C46H58O4
p-tert-butylcalix<4>crown
—— 5-fluoro-2,3-dimethylphenol 182011-08-1 C8H9FO
5-fluoro-2,3-dimethylphenol
—— 1-(2,4-Dihydroxyphenyl)-3-(pyridin-4-yl)propenone (6) 220430-84-2 C14H11NO3
1-(2,4-Dihydroxyphenyl)-3-(pyridin-4-yl)propenone (6)
—— 6-tert-Butyl-tricyclo[9.3.1.1<sup>4,8</sup>]hexadeca-1(14),4,6,8(16),11(15),12-hexaene-15,16-diol 201354-78-1 C20H24O2
6-tert-Butyl-tricyclo[9.3.1.1<sup>4,8</sup>]hexadeca-1(14),4,6,8(16),11(15),12-hexaene-15,16-diol
—— 2-(3,5-diethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-56-6 C16H22ClNO2S
2-(3,5-diethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— 4-chloro-5-fluoro-2,3-dimethylphenol 182011-15-0 C8H8ClFO
4-chloro-5-fluoro-2,3-dimethylphenol
—— (3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-4-methyl-phenylamino)-hexa-3,5-dien-2-one 196078-58-7 C15H17F3N2O2
(3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-4-methyl-phenylamino)-hexa-3,5-dien-2-one
—— 3-(3-hydroxy-4-methoxyphenyl)propionic acid benzyl ester 182249-52-1 C17H18O4
3-(3-hydroxy-4-methoxyphenyl)propionic acid benzyl ester
—— 5,11,17,23-Tetrabromo-2,8,14,20-tetrakis[4-(methoxymethoxy)butyl]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 174358-76-0 C52H68Br4O16
5,11,17,23-Tetrabromo-2,8,14,20-tetrakis[4-(methoxymethoxy)butyl]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
—— 3-hexadecyl-1,2-dihydroxybenzene 65216-88-8 C22H38O2
3-hexadecyl-1,2-dihydroxybenzene
—— 2-(3,5-diethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one 180090-40-8 C16H23NO3S
2-(3,5-diethyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
—— (R)-1,2,3,6-tetrahydro-4-(4-hydroxyphenyl)-1-{[3-(4-hydroxyphenyl)cyclohexen-1-yl]methyl}pyridine 216884-47-8 C24H27NO2
(R)-1,2,3,6-tetrahydro-4-(4-hydroxyphenyl)-1-{[3-(4-hydroxyphenyl)cyclohexen-1-yl]methyl}pyridine
—— 2-bromo-6-fluoro-3-methoxy-4,5-dimethylphenol 182010-41-9 C9H10BrFO2
2-bromo-6-fluoro-3-methoxy-4,5-dimethylphenol
—— 7,15-Ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-25,26,27-triol 206879-33-6 C32H40O6
7,15-Ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(25),5(27),6,8,13,15,17(26),21,23-nonaene-25,26,27-triol
—— 2-Heptadecyl-4-methoxy-phenol 148665-84-3 C24H42O2
2-Heptadecyl-4-methoxy-phenol
—— 7-Bromo-15,23-ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13,15,17(26),21(25),22-nonaene-25,26,27-triol 206879-53-0 C32H39BrO6
7-Bromo-15,23-ditert-butyl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13,15,17(26),21(25),22-nonaene-25,26,27-triol
—— 2-(4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-53-3 C12H14ClNO2S
2-(4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— 3,5-Dimethoxy-4-allylphenol 159427-01-7 C11H14O3
3,5-Dimethoxy-4-allylphenol
—— 5,11,17,23-tetrakis(1,1-dimethylundecyl)-25,26,27,28-tetrahydroxycalix[4]arene 189506-76-1 C80H128O4
5,11,17,23-tetrakis(1,1-dimethylundecyl)-25,26,27,28-tetrahydroxycalix[4]arene
—— 4-Chloro-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-benzonitrile 184766-73-2 C12H12ClNO3
4-Chloro-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-benzonitrile
—— 1-[(E)-2-(4-chlorophenyl)ethenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea 184003-09-6 C17H17ClN2O2S
1-[(E)-2-(4-chlorophenyl)ethenyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea
—— 5-bromo-13-tert-butyl-8,16-dihydroxy[2.2]metacyclophane 201354-80-5 C20H23BrO2
5-bromo-13-tert-butyl-8,16-dihydroxy[2.2]metacyclophane
—— 2-Heptadecyl-5-methoxy-phenol 148665-83-2 C24H42O2
2-Heptadecyl-5-methoxy-phenol
—— 2,3,5,6-Tetrachloro-4-[(4-methoxyphenyl)-trimethylsilylmethoxy]phenol 172796-88-2 C17H18Cl4O3Si
2,3,5,6-Tetrachloro-4-[(4-methoxyphenyl)-trimethylsilylmethoxy]phenol
—— 2-Allyl-6-chloro-3-methoxy-4,5-dimethyl-phenol 1027205-05-5 C12H15ClO2
2-Allyl-6-chloro-3-methoxy-4,5-dimethyl-phenol
—— 5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol 334708-29-1 C26H26O7S
5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol
—— N-(5-bromo-2-hydroxy-3-methoxyphenyl)formamide 198280-96-5 C8H8BrNO3
N-(5-bromo-2-hydroxy-3-methoxyphenyl)formamide
—— Ethyl 2-(5-bromo-2-hydroxyphenyl)acetate 220801-65-0 C10H11BrO3
Ethyl 2-(5-bromo-2-hydroxyphenyl)acetate
—— 4,5-Dimethoxy-2-propylsulfanylmethyl-phenol 179630-60-5 C12H18O3S
4,5-Dimethoxy-2-propylsulfanylmethyl-phenol
—— 2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-54-4 C14H18ClNO2S
2-(3,5-dimethyl-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— N-o-hydroxybenzyl-N-isopropylhydroxylamine 180265-67-2 C10H15NO2
N-o-hydroxybenzyl-N-isopropylhydroxylamine
—— 3-(1,4,5,6-Tetrahydropyrimidin-2-yl)phenol 848850-63-5 C10H12N2O
3-(1,4,5,6-Tetrahydropyrimidin-2-yl)phenol
—— (Z)-4-(5-Chloro-2-hydroxy-phenylamino)-1,1,1-trifluoro-pent-3-en-2-one 196078-53-2 C11H9ClF3NO2
(Z)-4-(5-Chloro-2-hydroxy-phenylamino)-1,1,1-trifluoro-pent-3-en-2-one
—— (3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-5-methyl-phenylamino)-hexa-3,5-dien-2-one 196078-57-6 C15H17F3N2O2
(3Z,5E)-6-Dimethylamino-1,1,1-trifluoro-4-(2-hydroxy-5-methyl-phenylamino)-hexa-3,5-dien-2-one
—— Phenol, 2-(1,2-dihydro-4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxy- 163392-76-5 C22H19N3O2
Phenol, 2-(1,2-dihydro-4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxy-