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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
—— (7R,7'R)-8(8')-ene-4,4'-dihydroxy-7,7'-epoxylignan 128450-69-1 C18H18O3
(7R,7'R)-8(8')-ene-4,4'-dihydroxy-7,7'-epoxylignan
—— (+/-)-KWD 2110 127560-11-6 C11H15NO3
(+/-)-KWD 2110
—— 2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-(propylamino)- 95503-98-3 C15H25NO3
2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-(propylamino)-
—— 5-(3-Hydroxyphenyl)isothiazol-3(2H)-one 1,1-dioxide 850314-30-6 C9H7NO4S
5-(3-Hydroxyphenyl)isothiazol-3(2H)-one 1,1-dioxide
—— isolaurenisol 93236-38-5 C15H19BrO
isolaurenisol
—— anti-<3.2>metacyclophanequinhydrone 143309-53-9 C17H16O4
anti-<3.2>metacyclophanequinhydrone
—— (1S,3R)-3-(2-Hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol 154699-13-5 C15H20O2
(1S,3R)-3-(2-Hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol
—— 2,9,9-Trimethyl-6,7,8,9-tetrahydro-5H-dibenzo[a,d]cycloheptene-3,11-diol 155679-44-0 C18H22O2
2,9,9-Trimethyl-6,7,8,9-tetrahydro-5H-dibenzo[a,d]cycloheptene-3,11-diol
—— diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(2-pyrimidinyl)-amino]-ethylphosphonate 407583-28-2 C20H30N3O6P
diisopropyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(2-pyrimidinyl)-amino]-ethylphosphonate
—— 2-(4-Hydroxy-3-methylphenyl)ethanol 307311-40-6 C9H12O2
2-(4-Hydroxy-3-methylphenyl)ethanol
—— 2-(4-Hydroxy-3-methoxy-phenyl)pentan 27060-47-5 C12H18O2
2-(4-Hydroxy-3-methoxy-phenyl)pentan
—— 5-(5-bromo-2-hydroxyphenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione 265320-63-6 C17H14BrNO5
5-(5-bromo-2-hydroxyphenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione
—— Ethyl I+/-,2,3-trihydroxybenzeneacetate 152354-67-1 C10H12O5
Ethyl I+/-,2,3-trihydroxybenzeneacetate
—— 3-Ethyl-4-(4-hydroxy-phenyl)-2-methyl-cyclohex-3-enecarboxylic acid 22921-17-1 C16H20O3
3-Ethyl-4-(4-hydroxy-phenyl)-2-methyl-cyclohex-3-enecarboxylic acid
—— 3-Methoxy-5-(1,1,5-trimethylhexyl)phenol 296242-08-5 C16H26O2
3-Methoxy-5-(1,1,5-trimethylhexyl)phenol
—— 4-Cycloheptyl-resorcin 15817-68-2 C13H18O2
4-Cycloheptyl-resorcin
—— 6-[1-(2,2-Diethoxyethylamino)-2-hydroxyethyl]-2-methoxy-3-methylphenol 147807-86-1 C16H27NO5
6-[1-(2,2-Diethoxyethylamino)-2-hydroxyethyl]-2-methoxy-3-methylphenol
—— Ethyl 2-hydroxy-5-nitrobenzeneacetate 116435-83-7 C10H11NO5
Ethyl 2-hydroxy-5-nitrobenzeneacetate
—— anti-6,9,14,17-tetrahydroxy<3.2>metacyclophane 143309-54-0 C17H18O4
anti-6,9,14,17-tetrahydroxy<3.2>metacyclophane
—— Ethyl 3-[3-tert-butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate 343870-38-2 C26H36O7S
Ethyl 3-[3-tert-butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate
—— ethyl 2-chloro-6-hydroxyphenyl(diethoxymethyl)phosphinate 164532-03-0 C13H20ClO5P
ethyl 2-chloro-6-hydroxyphenyl(diethoxymethyl)phosphinate
—— 3,4-diamino-5-methyl-2-nitrophenol 147285-82-3 C7H9N3O3
3,4-diamino-5-methyl-2-nitrophenol
—— 3-(3-chloro-4-hydroxyphenyl)-5-(3-fluoro-4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 617688-86-5 C18H12ClFO3S
3-(3-chloro-4-hydroxyphenyl)-5-(3-fluoro-4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde
—— 1-[4-(2-Methoxyethyl)phenoxy]-3-(methylamino)propan-2-ol 80448-17-5 C13H21NO3
1-[4-(2-Methoxyethyl)phenoxy]-3-(methylamino)propan-2-ol
—— Nakitriol 161407-86-9 C11H12O3
Nakitriol
—— 1-tert-Butylamino-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol 109632-10-2 C16H27NO3
1-tert-Butylamino-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol
—— 6,19-Ditert-butyltricyclo[15.3.1.14,8]docosa-1(20),4,6,8(22),17(21),18-hexaene-21,22-diol 142838-73-1 C30H44O2
6,19-Ditert-butyltricyclo[15.3.1.14,8]docosa-1(20),4,6,8(22),17(21),18-hexaene-21,22-diol
—— 5-((R)-1-Amino-2-hydroxy-ethyl)-2-methoxy-benzene-1,3-diol 219911-58-7 C9H13NO4
5-((R)-1-Amino-2-hydroxy-ethyl)-2-methoxy-benzene-1,3-diol
—— 2-Hydroxy-3,6-dimethoxy-5-methyl-benzaldehyde 1027942-34-2 C10H12O4
2-Hydroxy-3,6-dimethoxy-5-methyl-benzaldehyde
—— 3-(3,4-Dihydroxyphenyl)propyl tetradecanoate 196883-87-1 C23H38O4
3-(3,4-Dihydroxyphenyl)propyl tetradecanoate
—— 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