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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
—— (4S)-{[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]hept-1-yl]carbonylthio}-4,5-dihydro-2(3H)-furanone —— C14H18O5S
(4S)-{[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]hept-1-yl]carbonylthio}-4,5-dihydro-2(3H)-furanone
—— 4-ethyl(thiocarbonyl)thio-4,5-dihydro-2(3H)-furanone —— C7H10O2S2
4-ethyl(thiocarbonyl)thio-4,5-dihydro-2(3H)-furanone
—— rac-3-[2-(2-dimethylamino)-propyl]-butyrolactone —— C9H17NO2
rac-3-[2-(2-dimethylamino)-propyl]-butyrolactone
—— rac-3-(R/S)-[(isopropylmethylamino)-methylenyl]-butyrolactone —— C9H17NO2
rac-3-(R/S)-[(isopropylmethylamino)-methylenyl]-butyrolactone
—— (+/-)-(3R,4R)-3-ethyl-4-hydroxy-4-phenyltetrahydrofuran-2-one —— C12H14O3
(+/-)-(3R,4R)-3-ethyl-4-hydroxy-4-phenyltetrahydrofuran-2-one
—— (4R*,1'R*'2'R*)-4-(1,2-Dioxy-1-methyl-4-phenylbutyl)tetrahydro-2-furanone —— C15H20O4
(4R*,1'R*'2'R*)-4-(1,2-Dioxy-1-methyl-4-phenylbutyl)tetrahydro-2-furanone
—— (4R)-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-2-furanone —— C11H18N2O3
(4R)-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-2-furanone
—— (4RS)-4-{[(R)-N-α-methylbenzylamino](thiocarbonyl)thio}-4,5-dihydro-2(3H)-furanone —— C13H15NO2S2
(4RS)-4-{[(R)-N-α-methylbenzylamino](thiocarbonyl)thio}-4,5-dihydro-2(3H)-furanone
—— 3-<3'-(N-t-butyldiphenylsilyl-S-phenylsulfonimidoyl)-2'-propenyl>-5-oxacyclopentan-2-one —— C29H33NO3SSi
3-<3'-(N-t-butyldiphenylsilyl-S-phenylsulfonimidoyl)-2'-propenyl>-5-oxacyclopentan-2-one
—— 4-ethoxy(thiocarbonyl)thio-4,5-dihydro-2(3H)-furanone —— C7H10O3S2
4-ethoxy(thiocarbonyl)thio-4,5-dihydro-2(3H)-furanone
—— rac-3-[1-diethylaminoethyl]-butyrolactone —— C10H19NO2
rac-3-[1-diethylaminoethyl]-butyrolactone
—— 4-methyl(thiocarbonyl)thio-4,5-dihydro-2(3H)-furanone —— C6H8O2S2
4-methyl(thiocarbonyl)thio-4,5-dihydro-2(3H)-furanone
—— 4-[(2-amino-1-cyclopenten-1-yl)(thiocarbonyl)thio]-4,5-dihydro-2(3H)-furanone —— C10H13NO2S2
4-[(2-amino-1-cyclopenten-1-yl)(thiocarbonyl)thio]-4,5-dihydro-2(3H)-furanone
—— 4-{[2-(N-methylamino)-1-cyclopenten-1-yl](thiocarbonyl)thio}-4,5-dihydro-2(3H)-furanone —— C11H15NO2S2
4-{[2-(N-methylamino)-1-cyclopenten-1-yl](thiocarbonyl)thio}-4,5-dihydro-2(3H)-furanone
—— 4-acetylthio-4,5-dihydro-2(3H)-furanone —— C6H8O3S
4-acetylthio-4,5-dihydro-2(3H)-furanone
—— γ-butyrolactone-3-yl methacrylate —— C8H10O4
γ-butyrolactone-3-yl methacrylate
—— 6-butyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-one —— C13H22O2
6-butyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-one
—— (E)-5-butyl-2'-oxotetrahydro-[2,3']-bifuranylidene —— C12H18O3
(E)-5-butyl-2'-oxotetrahydro-[2,3']-bifuranylidene
—— 5-bromo-3,4,5,6-tetrahydro-4,4-dimethyl-6-trichloromethyl-2H-pyran-2-one —— C8H10BrCl3O2
5-bromo-3,4,5,6-tetrahydro-4,4-dimethyl-6-trichloromethyl-2H-pyran-2-one
—— 4-hydroxy-4-phenyldihydrofuran-2(3H)-one —— C10H10O3
4-hydroxy-4-phenyldihydrofuran-2(3H)-one
—— (1S,4S,5R)-5-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one —— C13H18O4
(1S,4S,5R)-5-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— (1S,4S,5R)-4-hydroxymethyl-3-oxabicyclo[3.2.0]heptan-2-one —— C7H10O3
(1S,4S,5R)-4-hydroxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
—— (1R*,2S*,3R*,4R*)-3,4-dichlorocyclobutane-1,2-dicarboxylic anhydride —— C6H4Cl2O3
(1R*,2S*,3R*,4R*)-3,4-dichlorocyclobutane-1,2-dicarboxylic anhydride
—— 3,4-dichlorocyclobutane-1,2-dicarboxylic anhydride —— C6H4Cl2O3
3,4-dichlorocyclobutane-1,2-dicarboxylic anhydride
—— α-methyl-β-ethyl-γ-methyl-γ-phenylvalerolactone —— C15H20O2
α-methyl-β-ethyl-γ-methyl-γ-phenylvalerolactone
—— (3aS,9R,9aS,9bS)-6,9-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-9-yl 2,2-dichloroacetate —— C17H20Cl2O4
(3aS,9R,9aS,9bS)-6,9-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-9-yl 2,2-dichloroacetate
—— 4-ethyl-3,5,5-trimethyl-tetrahydro-pyran-2-one —— C10H18O2
4-ethyl-3,5,5-trimethyl-tetrahydro-pyran-2-one
—— (R)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]oxetan-2-one —— C11H22O3Si
(R)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]oxetan-2-one
—— (+/-)-4-(2-tert-butyldimethylsiloxyethyl)oxetan-2-one —— C11H22O3Si
(+/-)-4-(2-tert-butyldimethylsiloxyethyl)oxetan-2-one
—— rac-(3R,4R)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-3-methyloxetan-2-one —— C12H24O3Si
rac-(3R,4R)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-3-methyloxetan-2-one
—— (3R,4R)-trans-3-Methyl-4-propyloxetan-2-one —— C7H12O2
(3R,4R)-trans-3-Methyl-4-propyloxetan-2-one
—— α-(1'-chloroethylidene)-β-(chloromethyl)-γ-butyrolactone —— C7H8Cl2O2
α-(1'-chloroethylidene)-β-(chloromethyl)-γ-butyrolactone
—— 6(R)-[2-[8(S)-(2,2-Dimethylbutyryloxy)-6(S)-propylaminocarbonyl-2(S)-methyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one —— C28H43NO6
6(R)-[2-[8(S)-(2,2-Dimethylbutyryloxy)-6(S)-propylaminocarbonyl-2(S)-methyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
—— (4R*,5R*)-3-methylidene-2-oxo-4-methyl-4,5-dibutyltetrahydrofuran —— C14H24O2
(4R*,5R*)-3-methylidene-2-oxo-4-methyl-4,5-dibutyltetrahydrofuran
—— (4R*,5R*)-3-methylidene-2-oxo-4-methyl-4-butyl-5-(2-methylpropyl)tetrahydrofuran —— C14H24O2
(4R*,5R*)-3-methylidene-2-oxo-4-methyl-4-butyl-5-(2-methylpropyl)tetrahydrofuran
—— (3R,4S)-4-isobutyl-3-methyloxetan-2-one —— C8H14O2
(3R,4S)-4-isobutyl-3-methyloxetan-2-one
—— (1S, 4S, 5R)-1,4-di(tert-butyldimethylsilyloxy)-3-oxocyclohexan-1,5-carbolactone —— C19H36O5Si2
(1S, 4S, 5R)-1,4-di(tert-butyldimethylsilyloxy)-3-oxocyclohexan-1,5-carbolactone
—— trans-4-methyl-5-pentyldihydrofuran-2(3H)-one —— C10H18O2
trans-4-methyl-5-pentyldihydrofuran-2(3H)-one
—— cis-4-methyl-5-pentyldihydrofuran-2(3H)-one —— C10H18O2
cis-4-methyl-5-pentyldihydrofuran-2(3H)-one
—— (2S,3S)-2-benzyl-3-hydroxy-γ-butyrolactone —— C11H12O3
(2S,3S)-2-benzyl-3-hydroxy-γ-butyrolactone
—— 2,2-difluoroglutaric anhydride 79361-03-8 C5H4F2O3
2,2-difluoroglutaric anhydride
—— (R)-pantolactone 2-O-diazoacetate —— C8H10N2O4
(R)-pantolactone 2-O-diazoacetate
—— 4-trifluoromethyl-2-methylene-γ-butyrolactone —— C6H5F3O2
4-trifluoromethyl-2-methylene-γ-butyrolactone
—— 5-(bromomethyl)-5-(methyl)dihydrofuran-2(3H)-one —— C6H9BrO2
5-(bromomethyl)-5-(methyl)dihydrofuran-2(3H)-one
—— (3SR,4RS,5RS)-3,4-dimethyl-5-[(1RS)-1-methylprop-2-enyl]-4,5-dihydrofuran-2(3H)-one —— C10H16O2
(3SR,4RS,5RS)-3,4-dimethyl-5-[(1RS)-1-methylprop-2-enyl]-4,5-dihydrofuran-2(3H)-one
—— (E)-5-bromomethyl-2'-oxotetrahydro-[2,3']-bifuranylidene —— C9H11BrO3
(E)-5-bromomethyl-2'-oxotetrahydro-[2,3']-bifuranylidene
—— (E)-5-bromomethyl-5'-ethyl-2'-oxotetrahydro-[2,3']-bifuranylidene —— C11H15BrO3
(E)-5-bromomethyl-5'-ethyl-2'-oxotetrahydro-[2,3']-bifuranylidene
—— 3-methyl-4-vinyldihydrofuran-2(3H)-one —— C7H10O2
3-methyl-4-vinyldihydrofuran-2(3H)-one
—— maleic anhydride-gamma butyrolactone —— C4H2O3*C4H6O2
maleic anhydride-gamma butyrolactone
—— 3,3-dibenzyldihydrofuran-2(3H)-one —— C18H18O2
3,3-dibenzyldihydrofuran-2(3H)-one