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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
—— 6-methoxycarbonylmethyl-6-hexanolide —— C9H14O4
6-methoxycarbonylmethyl-6-hexanolide
—— (R,S)-4,5-dihydro-3,3-dipropyl-4-(2-thiophenesulfonamido)-2(3H)-furanone —— C14H21NO4S2
(R,S)-4,5-dihydro-3,3-dipropyl-4-(2-thiophenesulfonamido)-2(3H)-furanone
—— (E)-5-[(2,2-dimethyl-1-thioxopropoxy)methyl]-5-(hydroxymethyl)-3-[5-methyl-3-(2-methylpropyl)hexylidene]-4,5-dihydrofuran-2-one —— C22H38O4S
(E)-5-[(2,2-dimethyl-1-thioxopropoxy)methyl]-5-(hydroxymethyl)-3-[5-methyl-3-(2-methylpropyl)hexylidene]-4,5-dihydrofuran-2-one
—— (3R,4S,5R,1'S,2'S)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one —— C11H20O4
(3R,4S,5R,1'S,2'S)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one
—— (3R,4S,5S,1'R,2'S)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one —— C11H20O4
(3R,4S,5S,1'R,2'S)-4-hydroxy-5-(1-hydroxy-2-methylbutyl)-3,5-dimethyl-4,5-dihydrofuran-2(3H)-one
—— (3S,6S)-6-tert-butyldimethylsilyloxy-7,7-dimethyl-3-[(1S,2R)-2-methyl-3-oxocyclopentyl]oxepan-2-one —— C20H36O4Si
(3S,6S)-6-tert-butyldimethylsilyloxy-7,7-dimethyl-3-[(1S,2R)-2-methyl-3-oxocyclopentyl]oxepan-2-one
—— 4-Methyl-4-(1-methylethenyl)-2H-pyran-2-one —— C9H14O2
4-Methyl-4-(1-methylethenyl)-2H-pyran-2-one
—— (1S,5R,6R)-6-(4-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one —— C11H9ClO2
(1S,5R,6R)-6-(4-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
—— 3-methyl-4-methylene-3-propionyl-dihydrofuran-2-one —— C9H12O3
3-methyl-4-methylene-3-propionyl-dihydrofuran-2-one
—— (3S,4S,5S)-4-[(tert-butyldimethylsilyl)oxy]-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one —— C12H24O4Si
(3S,4S,5S)-4-[(tert-butyldimethylsilyl)oxy]-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
—— (+/-)-cis-6-[4-(4-(aminoiminomethyl)phenyl)butyl]-4-ethenyl-tetrahydro-2H-pyran-2-one —— C18H24N2O2
(+/-)-cis-6-[4-(4-(aminoiminomethyl)phenyl)butyl]-4-ethenyl-tetrahydro-2H-pyran-2-one
—— 2(S)-methyl-3(R)-carboxy-4(S)-hydroxy-18-oxononadecan-1-4-olide —— C21H36O5
2(S)-methyl-3(R)-carboxy-4(S)-hydroxy-18-oxononadecan-1-4-olide
—— (4S*,5S*,Z)-3-ethylidene-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone —— C7H10O3
(4S*,5S*,Z)-3-ethylidene-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
—— (3aS,5aR,8aR,8bR)-5a-methyl-3a,4,5,5a-tetrahydro-1H-indeno[5,4-b]furan-2,8(8aH,8bH)-dione —— C12H14O3
(3aS,5aR,8aR,8bR)-5a-methyl-3a,4,5,5a-tetrahydro-1H-indeno[5,4-b]furan-2,8(8aH,8bH)-dione
—— (4S,6R)-4-hydroxy-6-pentafluorophenyltetrahydropyran-2-one —— C11H7F5O3
(4S,6R)-4-hydroxy-6-pentafluorophenyltetrahydropyran-2-one
—— (4R,5S,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one —— C12H9F5O3
(4R,5S,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one
—— (4R,5R,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one —— C12H9F5O3
(4R,5R,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one
—— 3-methylene-5-(2-phenylethyl)-2-tetrahydrofuranone —— C13H14O2
3-methylene-5-(2-phenylethyl)-2-tetrahydrofuranone
—— (3R,5R)-3-methyl-5-((1R,2R)-1,2,3-trihydroxypropyl)dihydrofuran-2(3H)-one —— C8H14O5
(3R,5R)-3-methyl-5-((1R,2R)-1,2,3-trihydroxypropyl)dihydrofuran-2(3H)-one
—— (+)-trans-aerangis lactone —— C11H20O2
(+)-trans-aerangis lactone
—— 2-(5-methyl-2-oxooxolan-3-yl)acetaldehyde —— C7H10O3
2-(5-methyl-2-oxooxolan-3-yl)acetaldehyde
—— 5-hydroxycaprolactone —— C6H10O3
5-hydroxycaprolactone
—— δ-methyl-δ-ethoxycarbonyl-δ-valerolactone —— C9H14O4
δ-methyl-δ-ethoxycarbonyl-δ-valerolactone
—— (1S,1'S,4R,4'R,5R,5'R)-4,4'-[(1R,2R)-1,2-di-O-isopropylidenedioxyethane-1,2-diyl]bis(3-oxabicyclo[3.2.0]heptan-2-one) —— C17H22O6
(1S,1'S,4R,4'R,5R,5'R)-4,4'-[(1R,2R)-1,2-di-O-isopropylidenedioxyethane-1,2-diyl]bis(3-oxabicyclo[3.2.0]heptan-2-one)
—— dihydro-3,4-dihydroxy-4-methylfuran-2-one —— C5H8O4
dihydro-3,4-dihydroxy-4-methylfuran-2-one
—— (S)-6-ethenyltetrahydro-2H-pyran-2-one —— C7H10O2
(S)-6-ethenyltetrahydro-2H-pyran-2-one
—— trans-3-butyl-4-methyldihydrofuran-2(3H)-one —— C9H16O2
trans-3-butyl-4-methyldihydrofuran-2(3H)-one
—— (3aRS,4SR,7RS,7aSR)-7a-butyl-3a-methyl-3a,4,7,7a-tetra-hydro-4,7-methanoisobenzofuran-1(3H)-one —— C14H20O2
(3aRS,4SR,7RS,7aSR)-7a-butyl-3a-methyl-3a,4,7,7a-tetra-hydro-4,7-methanoisobenzofuran-1(3H)-one
—— cis-3-butyl-4-methyldihydrofuran-2(3H)-one —— C9H16O2
cis-3-butyl-4-methyldihydrofuran-2(3H)-one
—— statin II —— C24H36O6
statin II
—— statin IV —— C24H36O6
statin IV
—— 4,7-hemiketal of pseudoanisatin —— C15H22O6
4,7-hemiketal of pseudoanisatin
—— (+/-)-9-hex-5-enyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-one —— C13H20O2S2
(+/-)-9-hex-5-enyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-one
—— gluconolactone —— C6H10O6
gluconolactone
—— 6-(p-tolyl)tetrahydro-2H-pyran-2-one —— C12H14O2
6-(p-tolyl)tetrahydro-2H-pyran-2-one
—— (E)-5-t-butyl-3-ethylidenedihydrofuran-2(3H)-one —— C10H16O2
(E)-5-t-butyl-3-ethylidenedihydrofuran-2(3H)-one
—— trans-5-tert-butyl-3-methyldihydrofuran-2(3H)-one —— C9H16O2
trans-5-tert-butyl-3-methyldihydrofuran-2(3H)-one
—— cis-5-(3-hexyl-4-oxo-oxetan-2-yl)pentyl-isopropyl carbamate —— C18H33NO4
cis-5-(3-hexyl-4-oxo-oxetan-2-yl)pentyl-isopropyl carbamate
—— (±)-vibralactone —— C12H16O3
(±)-vibralactone
—— 2-Deoxy-~-glucono-l,5-lactone —— C6H10O5
2-Deoxy-~-glucono-l,5-lactone
—— 3-(2-ethylbutyl)-4-hydroxy-5-methyldihydrofuran-2(3H)-one —— C11H20O3
3-(2-ethylbutyl)-4-hydroxy-5-methyldihydrofuran-2(3H)-one
—— 4-(1-chloroethyl)oxetan-2-one —— C5H7ClO2
4-(1-chloroethyl)oxetan-2-one
—— 4-(tert-butyldimethylsilyloxy)-dihydrofuran-2(3H)-one —— C10H20O3Si
4-(tert-butyldimethylsilyloxy)-dihydrofuran-2(3H)-one
—— 5-methyl-4-({2-[(1S)-1-(methylthio)ethyl]phenyl}seleno)dihydrofuran-2(3H)-one —— C14H18O2SSe
5-methyl-4-({2-[(1S)-1-(methylthio)ethyl]phenyl}seleno)dihydrofuran-2(3H)-one
—— (2R,3S)-tetrahydro-4-methylene-5-oxo-2-n-pentyl-3-furancarboxylic acid —— C11H16O4
(2R,3S)-tetrahydro-4-methylene-5-oxo-2-n-pentyl-3-furancarboxylic acid
—— 3-(Z)-chloroethylidene-4R-chloromethyl-5R-pentyl-γ-butyrolactone —— C12H18Cl2O2
3-(Z)-chloroethylidene-4R-chloromethyl-5R-pentyl-γ-butyrolactone
—— 3-methylene-5-(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one —— C9H12O2
3-methylene-5-(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one
—— (3aR,6aS)-5-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one —— C15H24O3Si
(3aR,6aS)-5-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one
—— 1-bromo-4-pentyl-3-oxabicyclo[3.1.0]hexane-2-one —— C10H15BrO2
1-bromo-4-pentyl-3-oxabicyclo[3.1.0]hexane-2-one
—— 4-(hydroxymethyl)-3-methylene-5-pentyltetrahydrofuran-2-one —— C11H18O3
4-(hydroxymethyl)-3-methylene-5-pentyltetrahydrofuran-2-one