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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
—— 4,8-ditrityl-naphthalene-1,5-diol 117440-14-9 C48H36O2
4,8-ditrityl-naphthalene-1,5-diol
—— N-Benzoyl-N'-(3-chloro-2-hydroxy-5-nitro-phenyl)-guanidine 62314-76-5 C14H11ClN4O4
N-Benzoyl-N'-(3-chloro-2-hydroxy-5-nitro-phenyl)-guanidine
—— 4-(Cyclopropylamino)-2-nitrophenol;hydrochloride 897953-54-7 C9H10N2O3*ClH
4-(Cyclopropylamino)-2-nitrophenol;hydrochloride
—— 5,13,21,29-Tetraallyl-8,16,24,32-tetrahydroxy<2.2.2.2>metacyclophane 125666-12-8 C44H48O4
5,13,21,29-Tetraallyl-8,16,24,32-tetrahydroxy<2.2.2.2>metacyclophane
—— (2,4-Dihydroxyphenyl)acetaldehyd-dimethylhydrazon 74321-33-8 C10H14N2O2
(2,4-Dihydroxyphenyl)acetaldehyd-dimethylhydrazon
—— 2-[(2-hydroxy-5-chlorophenyl)amino]phenylacetic acid 320777-33-1 C14H12ClNO3
2-[(2-hydroxy-5-chlorophenyl)amino]phenylacetic acid
—— 3,4,5-trimethyl-2-nitrosophenol 69688-80-8 C9H11NO2
3,4,5-trimethyl-2-nitrosophenol
—— 2-[(3-chloro-4-hydroxyphenyl)amino]phenylacetic acid 320777-31-9 C14H12ClNO3
2-[(3-chloro-4-hydroxyphenyl)amino]phenylacetic acid
—— zinc(II) 5-(3,4-dihydroxyphenyl)-10,15,20-triphenyl-porphyrinate 171415-49-9 C44H28N4O2Zn
zinc(II) 5-(3,4-dihydroxyphenyl)-10,15,20-triphenyl-porphyrinate
—— (2s,4s,6s,8s)-2,4,6,8-tetrahexyl-15,35,55,75-tetramethyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphan-14,16,34,36,54,56,74,76-octaol 1005459-70-0 C56H80O8
(2s,4s,6s,8s)-2,4,6,8-tetrahexyl-15,35,55,75-tetramethyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphan-14,16,34,36,54,56,74,76-octaol
—— 2-hydroxy-4-nitro-benzoic acid diethylamide 647016-93-1 C11H14N2O4
2-hydroxy-4-nitro-benzoic acid diethylamide
—— 2,2'-Nonamethylenebis(1,4-dihydroxy-3,6-dimethoxybenzene) 99608-67-0 C25H36O8
2,2'-Nonamethylenebis(1,4-dihydroxy-3,6-dimethoxybenzene)
—— 2-<4-Hydroxy-3-methoxy-styryl>-3.4.5-trimethyl-thiazoliumiodid 97706-90-6 C15H18NO2S*I
2-<4-Hydroxy-3-methoxy-styryl>-3.4.5-trimethyl-thiazoliumiodid
—— N,N'-bis[2-(4-hydroxyphenyl)ethyl]hexanediamide 259527-75-8 C22H28N2O4
N,N'-bis[2-(4-hydroxyphenyl)ethyl]hexanediamide
—— neodymium(III) 3-((2-hydroxybenzylidene)amino)propanoate 3-((2-oxidobenzylidene)amino)propanoate 53041-90-0 C10H9NO3*C10H10NO3*Nd
neodymium(III) 3-((2-hydroxybenzylidene)amino)propanoate 3-((2-oxidobenzylidene)amino)propanoate
—— 6-(3-chloro-4-(3-{2-[4-((S)-1-oxiranylmethoxy)-phenyl]-ethoxy}-propoxy)-phenyl)-4,5-dihydro-2H-pyridazin-3-one 890042-66-7 C24H27ClN2O5
6-(3-chloro-4-(3-{2-[4-((S)-1-oxiranylmethoxy)-phenyl]-ethoxy}-propoxy)-phenyl)-4,5-dihydro-2H-pyridazin-3-one
—— trihydroxyphenylboronate 1447250-44-3 C6H7BO5
trihydroxyphenylboronate
—— diethyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-ethylphosphonate 407583-21-5 C18H26N3O6P
diethyl α-(3,5-dimethoxy-4-hydroxyphenyl)-β-[N-(pyrazinyl)-amino]-ethylphosphonate
—— 1-(4-Hydroxy-3,5-dimethoxyphenyl)-2,2-dimethyl-1-propanol 38775-76-7 C13H20O4
1-(4-Hydroxy-3,5-dimethoxyphenyl)-2,2-dimethyl-1-propanol
—— 6-[[4-(3,4-dihydroxy-5-nitrophenyl)-2-thiazolyl]amino]-4'-(trifluoromethyl)hexananilide 134610-78-9 C22H21F3N4O5S
6-[[4-(3,4-dihydroxy-5-nitrophenyl)-2-thiazolyl]amino]-4'-(trifluoromethyl)hexananilide
—— 3-methoxy-4-(1-methyl-2-butenyl)phenol 95414-64-5 C12H16O2
3-methoxy-4-(1-methyl-2-butenyl)phenol
—— 2-Hydroxy-3,6-dimethoxy-4,5-dimethyl-benzaldehyde 1027939-42-9 C11H14O4
2-Hydroxy-3,6-dimethoxy-4,5-dimethyl-benzaldehyde
—— hexamethylenetetramine; compound with phenol 59481-40-2 C6H6O*C6H12N4
hexamethylenetetramine; compound with phenol
—— 2-(((3-(Furan-2-yl)-5-mercapto-4H-1,2,4-triazol-4-yl)imino)methyl)-6-methoxyphenol 478253-69-9 C14H12N4O3S
2-(((3-(Furan-2-yl)-5-mercapto-4H-1,2,4-triazol-4-yl)imino)methyl)-6-methoxyphenol
—— 15-methyl-1-aza-[11]metacyclophan-2-one 108396-20-9 C17H25NO
15-methyl-1-aza-[11]metacyclophan-2-one
—— 3,5-Di-p-toluidino-phenol 855839-21-3 C20H20N2O
3,5-Di-p-toluidino-phenol
—— hexakis-salicylidenehydrazino-2λ<sup>5</sup>,4λ<sup>5</sup>,6λ<sup>5</sup>-cyclotriphosphazene 54475-40-0 C42H42N15O6P3
hexakis-salicylidenehydrazino-2λ<sup>5</sup>,4λ<sup>5</sup>,6λ<sup>5</sup>-cyclotriphosphazene
—— 4,4-diethylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate 1193987-98-2 C25H38N2O5
4,4-diethylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate
—— 2,8,14,20-tetrakis(9-decenyl)pentacyclo<19.3.1.13,7.19,13.115,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 161170-49-6 C68H96O8
2,8,14,20-tetrakis(9-decenyl)pentacyclo<19.3.1.13,7.19,13.115,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— ethyl [2-(5-chloro-2-hydroxyphenyl)-1,3-thiazol-4-yl]acetate 913650-41-6 C13H12ClNO3S
ethyl [2-(5-chloro-2-hydroxyphenyl)-1,3-thiazol-4-yl]acetate
—— 5-(4-hydroxy-3-methoxy-phenyl)-3-methyl-2-thioxo-[1,3,4]thiadiazinan-6-one oxime 50368-48-4 C11H13N3O3S2
5-(4-hydroxy-3-methoxy-phenyl)-3-methyl-2-thioxo-[1,3,4]thiadiazinan-6-one oxime
—— (R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide 691012-78-9 C22H25ClINO6
(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide
—— 2-(4-Hydroxy-3-methoxy-phenyl)-3-(2-mercapto-phenyl)-thiazolidin-4-one 128921-72-2 C16H15NO3S2
2-(4-Hydroxy-3-methoxy-phenyl)-3-(2-mercapto-phenyl)-thiazolidin-4-one
—— 1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide 94427-32-4 BrH*C12H15NO2
1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide
—— 2,6-bis(methylthiomethyl)-4-nitrophenol 4527-35-9 C10H13NO3S2
2,6-bis(methylthiomethyl)-4-nitrophenol
—— 4-[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-3-(5-methyl-1H-pyrazol-3-yl)-1H-1,2,4-triazole-5-thione 850241-83-7 C15H16N6O3S
4-[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-3-(5-methyl-1H-pyrazol-3-yl)-1H-1,2,4-triazole-5-thione
—— Tricyclo[9.3.1.1<sup>4,8</sup>]hexadeca-1(15),4,6,8(16),11,13-hexaene-6,13,15,16-tetraol 96481-04-8 C16H16O4
Tricyclo[9.3.1.1<sup>4,8</sup>]hexadeca-1(15),4,6,8(16),11,13-hexaene-6,13,15,16-tetraol
—— 904013-28-1 C19H20N4O6
—— tetracyclo[13.3.1.13,7.19,13]henicosa-1(19),3(21),4,6,9(20),10,12,15,17-nonaene-19,20,21-triol 83142-74-9 C21H18O3
tetracyclo[13.3.1.13,7.19,13]henicosa-1(19),3(21),4,6,9(20),10,12,15,17-nonaene-19,20,21-triol
—— [(E)-Hydroxyimino]-(4-hydroxy-3-methoxy-phenyl)-acetic acid 61561-11-3 C9H9NO5
[(E)-Hydroxyimino]-(4-hydroxy-3-methoxy-phenyl)-acetic acid
—— 4-[N-[3-[1-(2-hydroxyphenyl)ethylideneamino]propyl]-C-methylcarbonimidoyl]benzene-1,3-diol 433940-73-9 C19H22N2O3
4-[N-[3-[1-(2-hydroxyphenyl)ethylideneamino]propyl]-C-methylcarbonimidoyl]benzene-1,3-diol
—— 4-chloro-3,6-dimethyl-2-(2-nitro-benzenesulfonyl)-phenol 854663-12-0 C14H12ClNO5S
4-chloro-3,6-dimethyl-2-(2-nitro-benzenesulfonyl)-phenol
—— 3'-Chloro-5-nitro-2-hydroxyphenylmethansulfonat 66950-30-9 C13H10ClNO6S
3'-Chloro-5-nitro-2-hydroxyphenylmethansulfonat
—— N-[1-(2-hydroxy-5-methoxyphenyl)ethylideneamino]-2-methylbenzamide 1235837-38-3 C17H18N2O3
N-[1-(2-hydroxy-5-methoxyphenyl)ethylideneamino]-2-methylbenzamide
—— 7-ethyl-2-(4-hydroxy-3-methoxy-phenyl)-1,5,6,7-tetrahydro-2<i>H</i>-cyclopenta[<i>d</i>][1,3]thiazine-4-thione 42037-94-5 C16H19NO2S2
7-ethyl-2-(4-hydroxy-3-methoxy-phenyl)-1,5,6,7-tetrahydro-2<i>H</i>-cyclopenta[<i>d</i>][1,3]thiazine-4-thione
—— 6-Methylmercapto-methyl-vanillin 18738-40-4 C10H12O3S
6-Methylmercapto-methyl-vanillin
—— 4-(3-((tetrahydro-2H-pyran-2-yloxy)methyl)furazan-3-yl)phenol 862801-54-5 C14H16N2O4
4-(3-((tetrahydro-2H-pyran-2-yloxy)methyl)furazan-3-yl)phenol
—— 2-[<i>trans</i>-2-(9,9-dimethyl-2,3-dihydro-9<i>H</i>-oxazolo[3,2-<i>a</i>]indol-9a-yl)-vinyl]-6-nitro-phenol 51031-55-1 C20H20N2O4
2-[<i>trans</i>-2-(9,9-dimethyl-2,3-dihydro-9<i>H</i>-oxazolo[3,2-<i>a</i>]indol-9a-yl)-vinyl]-6-nitro-phenol
—— 1-methyl-2-(3,4-dihydroxybenzyl)imidazoline hydrochloride 85612-44-8 C11H14N2O2*ClH
1-methyl-2-(3,4-dihydroxybenzyl)imidazoline hydrochloride
—— methyl 4-hydroxy-3-iodobenzimidate hydrochloride 106050-87-7 C8H8INO2*ClH
methyl 4-hydroxy-3-iodobenzimidate hydrochloride