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内酯类

内酯类化合物是一类含有环状结构的化合物,通常通过一个碳氧双键将两个羟基连接在一个四元、五元或六元的内环中形成。这类化合物广泛存在于自然界中,并且在有机化学、化学化工以及生物医药领域有着重要的应用价值。

内酯的分类
  1. 按环大小划分:根据内酯环的大小,可以将其分为四元、五元和六元内酯。
  2. 按碳原子数划分:依据组成内酯的碳原子数量不同,可进一步划分为二、三、四等碳链长度不同的内酯。
结构特征
  • 内酯结构中通常包含一个或多个环状氧基团。其独特的环状结构使得它们在水溶液中能够以开环形式存在。
  • 在生物体内,某些内酯通过酶的催化作用可实现快速转化,在药物设计和研究领域具有重要应用价值。
应用
  1. 医药领域:许多抗生素、抗真菌药及抗癌药物都含有内酯结构。例如,四环素类抗生素就含有五元或六元内酯。
  2. 工业化学:内酯作为重要的化工原料,在合成树脂、塑料和涂料等领域有着广泛应用。
  3. 分析化学与生物传感器:利用内酯的可逆开环性质进行分析检测;通过构建特定识别分子对提高生物传感系统的特异性。
生物活性
  • 内酯化合物通常具有一定的药理活性,如抗炎、抗菌等作用。这与其独特的空间构象和极性有关。
  • 在细胞信号传导过程中,内酯的环开裂或闭合可以影响特定蛋白质之间的相互作用。

总之,内酯作为一种重要的化学结构单元,在多个领域发挥着不可替代的作用。

中文名称 英文名称 CAS号 化学式 结构式图片
—— (-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one 111138-02-4 C10H10O2
(-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one
—— 5-(hydroxymethyl)-5-methyldihydrofuran-2(3H)-one 74397-28-7 C6H10O3
5-(hydroxymethyl)-5-methyldihydrofuran-2(3H)-one
—— 4-(6-oxotetrahydro-2H-pyran-2-yl)butanoic acid 110719-99-8 C9H14O4
4-(6-oxotetrahydro-2H-pyran-2-yl)butanoic acid
—— (3S)-3-(hydroxymethyl)oxan-2-one 1374751-24-2 C6H10O3
(3S)-3-(hydroxymethyl)oxan-2-one
—— 4-bromomethyl-β-lactone 33282-42-7 C4H5BrO2
4-bromomethyl-β-lactone
—— olean-12α-hydroxy-3-ε-lacton-28-oic acid γ-lactone 1255647-22-3 C30H46O5
olean-12α-hydroxy-3-ε-lacton-28-oic acid γ-lactone
—— (2S,4R)-2-hydroxy-4-hydroxymethyl-4-butanolide 117141-71-6 C5H8O4
(2S,4R)-2-hydroxy-4-hydroxymethyl-4-butanolide
—— cis-3-chlorodihydro-5-phenyl-2(3H)-furanone —— C10H9ClO2
cis-3-chlorodihydro-5-phenyl-2(3H)-furanone
—— trans-3-chlorodihydro-5-phenyl-2(3H)-furanone 72406-99-6 C10H9ClO2
trans-3-chlorodihydro-5-phenyl-2(3H)-furanone
—— 3,4-dimethyl-3-phenyl-γ-valerolactone 90691-70-6 C13H16O2
3,4-dimethyl-3-phenyl-γ-valerolactone
—— 2-chloro-4-octylbutyrolactone 72925-00-9 C12H21ClO2
2-chloro-4-octylbutyrolactone
—— 3,3-dichloro-5,5-diethyldihydro-2(3H)-furanone 89344-97-8 C8H12Cl2O2
3,3-dichloro-5,5-diethyldihydro-2(3H)-furanone
—— 6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione 84465-82-7 C7H10O3
6,6-dimethyldihydro-2H-pyran-2,4(3H)-dione
—— (2S,3R)-5-Eth-(E)-ylidene-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid 10407-74-6 C10H14O4
(2S,3R)-5-Eth-(E)-ylidene-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid
—— (3aR,4S,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)hexahydro-2H-cyclopenta[b]furan-2-one 117624-93-8 C20H40O4Si2
(3aR,4S,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)hexahydro-2H-cyclopenta[b]furan-2-one
—— <i>D</i>-<i>glycero</i>-<i>D</i>-<i>talo</i>-heptonic acid 4-lactone 15397-09-8 C7H12O7
<i>D</i>-<i>glycero</i>-<i>D</i>-<i>talo</i>-heptonic acid 4-lactone
—— artabsinolide D 81907-04-2 C15H22O5
artabsinolide D
—— artabsinolide C 81907-05-3 C15H22O5
artabsinolide C
—— teugnaphalodin 101416-45-9 C20H26O7
teugnaphalodin
—— biocartol 350699-93-3 C7H10O3
biocartol
—— 1,8,8-trimethyl-2-oxabicyclo<3.2.1>octan-3-one 28973-92-4 C10H16O2
1,8,8-trimethyl-2-oxabicyclo<3.2.1>octan-3-one
—— 7-[(Ξ)-furfuryliden-oxepan-2-one 99865-42-6 C11H12O3
7-[(Ξ)-furfuryliden-oxepan-2-one
—— Cycloprop[6,7]indeno[4,5-b]furan-2(3H)-one, 6-(acetyloxy)decahydro-7a-hydroxy-4a,7-dimethyl-3-methylene- 13048-24-3 C17H22O5
Cycloprop[6,7]indeno[4,5-b]furan-2(3H)-one, 6-(acetyloxy)decahydro-7a-hydroxy-4a,7-dimethyl-3-methylene-
—— (+/-)-7-(2'-acetoxyethyl)-2-oxepanone 92016-30-3 C10H16O4
(+/-)-7-(2'-acetoxyethyl)-2-oxepanone
—— (S)-β-acetoxy-γ-butyrolactone 19405-98-2 C6H8O4
(S)-β-acetoxy-γ-butyrolactone
—— ω-acetoxyl-4-phenyl-γ-pentanolactone 1355616-68-0 C13H14O4
ω-acetoxyl-4-phenyl-γ-pentanolactone
—— 1,8,8-trimethyl-3-oxabicyclo(3.2.1)oct-2-one 507-96-0 C10H16O2
1,8,8-trimethyl-3-oxabicyclo(3.2.1)oct-2-one
—— 1,8,8-trimethyl-2-oxabicyclo<3.2.1>octan-3-one 111056-61-2 C10H16O2
1,8,8-trimethyl-2-oxabicyclo<3.2.1>octan-3-one
—— (4Z,4aS,7Z,9R,11aR)-9-hydroxy-4-((E)-4-hydroxy-4-methylpent-2-enylidene)-7-methyl-11-methylene-4,4a,5,6,9,10,11,11a-octahydrocyclonona[c]pyran-3(1H)-one 1120358-56-6 C20H28O4
(4Z,4aS,7Z,9R,11aR)-9-hydroxy-4-((E)-4-hydroxy-4-methylpent-2-enylidene)-7-methyl-11-methylene-4,4a,5,6,9,10,11,11a-octahydrocyclonona[c]pyran-3(1H)-one
—— L-threo-2,3-hexodiulosono-1,4-lactone 490-83-5 C6H6O6
L-threo-2,3-hexodiulosono-1,4-lactone
—— (4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-vinyl-dihydrofuran-2-one 160308-93-0 C23H28O3Si
(4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-vinyl-dihydrofuran-2-one
—— L-dehydroascorbic acid 490-83-5 C6H6O6
L-dehydroascorbic acid
—— 3-hydroxy-2-methyl-γ-butyrolacton —— C5H8O3
3-hydroxy-2-methyl-γ-butyrolacton
—— (1S,4S,5S)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one 123536-66-3 C7H9IO2
(1S,4S,5S)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one
—— (3S,4R,6R)-4-hydroxy-3-methyl-6-(2-phenylethyl)oxan-2-one 132895-34-2 C14H18O3
(3S,4R,6R)-4-hydroxy-3-methyl-6-(2-phenylethyl)oxan-2-one
—— 2,3-dideoxy-3-C-methyl-5-O-tert-butyldiphenylsilyl-D-threo-pentono-1,4-lactone 106820-50-2 C22H28O3Si
2,3-dideoxy-3-C-methyl-5-O-tert-butyldiphenylsilyl-D-threo-pentono-1,4-lactone
—— (4S,5S)-5-tert-butyldimethylsilyloxyheptadecan-4-olide 144763-47-3 C23H46O3Si
(4S,5S)-5-tert-butyldimethylsilyloxyheptadecan-4-olide
—— (2R,3R,4S)-5-[(tert-butyldiphenylsilyl)oxy]-2-hydroxy-3-methyl-4-pentanolide 106820-52-4 C22H28O4Si
(2R,3R,4S)-5-[(tert-butyldiphenylsilyl)oxy]-2-hydroxy-3-methyl-4-pentanolide
—— (5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one 190380-57-5 C25H48O4Si
(5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one
—— (5R)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one 190380-56-4 C25H48O4Si
(5R)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one
—— (4S,5S,8S,9S)-9-tert-butyldimethylsilyloxy-5,8-epoxyhenicosan-4-olide 287185-34-6 C27H52O4Si
(4S,5S,8S,9S)-9-tert-butyldimethylsilyloxy-5,8-epoxyhenicosan-4-olide
—— 6-oxabicyclo<3.2.1>-oct-3-en-7-one 4720-83-6 C7H8O2
6-oxabicyclo<3.2.1>-oct-3-en-7-one
—— 3-Cyclohexene-1-carboxylic acid (S)-pantolactone ester 127604-94-8 C13H18O4
3-Cyclohexene-1-carboxylic acid (S)-pantolactone ester
—— (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one 62396-80-9 C11H22O3Si
(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one
—— (2aS,3S,6aS,6bS)-3-[(1S)-1,2-dihydroxyethyl]hexahydro-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one 882032-61-3 C9H13NO5
(2aS,3S,6aS,6bS)-3-[(1S)-1,2-dihydroxyethyl]hexahydro-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one
—— α-mercaptomethyl-β-phenyl-γ-butyrolactone 98162-81-3 C11H12O2S
α-mercaptomethyl-β-phenyl-γ-butyrolactone
—— 4-ethyl-4-methyloxetan-2-one 4288-03-3 C6H10O2
4-ethyl-4-methyloxetan-2-one
—— (4R)-4-(1,1-dichloroheptyl)oxetan-2-one 101392-67-0 C10H16Cl2O2
(4R)-4-(1,1-dichloroheptyl)oxetan-2-one
—— 4-(1,1-Dichloropropyl)oxetan-2-one 105952-80-5 C6H8Cl2O2
4-(1,1-Dichloropropyl)oxetan-2-one
—— 4-(chloromethyl)-4-methyloxetan-2-one 10358-99-3 C5H7ClO2
4-(chloromethyl)-4-methyloxetan-2-one