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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
—— (3S)-5-[(E,3R)-3-hydroxy-2-methylpent-1-enyl]-3-methyl-5-(trimethylsilylmethyl)oxolan-2-one 1026407-75-9 C15H28O3Si
(3S)-5-[(E,3R)-3-hydroxy-2-methylpent-1-enyl]-3-methyl-5-(trimethylsilylmethyl)oxolan-2-one
—— (+)-trans-cognac lactone —— C10H18O2
(+)-trans-cognac lactone
—— (4R,6S)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one 531559-40-7 C10H18O2
(4R,6S)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one
—— 6-[2-(tert-butyldimethylsilanyloxy)ethyl]-5-methyltetrahydropyran-2-one 187218-77-5 C14H28O3Si
6-[2-(tert-butyldimethylsilanyloxy)ethyl]-5-methyltetrahydropyran-2-one
—— 3,3-Dimethyl-1-oxaspiro<3.5>nonan-2-one 22741-15-7 C10H16O2
3,3-Dimethyl-1-oxaspiro<3.5>nonan-2-one
—— trans-(+/-)-4-heptyl-3-methyloxetan-2-one —— C11H20O2
trans-(+/-)-4-heptyl-3-methyloxetan-2-one
—— 2,3,5,6-tetra-O-tert-butyldimethylsilyl-D-galactono-1,4-lactone 221467-94-3 C30H66O6Si4
2,3,5,6-tetra-O-tert-butyldimethylsilyl-D-galactono-1,4-lactone
—— methyl 2-((2R,4aS,7S,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-oxooctahydropyrano[3,2-b]pyran-2-yl)acetate 1028777-20-9 C23H44O7Si2
methyl 2-((2R,4aS,7S,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-oxooctahydropyrano[3,2-b]pyran-2-yl)acetate
—— (3aS,5S,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-6a-methyl-3a,4,5,6-tetrahydro-3H-cyclopenta[b]furan-2-one 954145-06-3 C14H26O3Si
(3aS,5S,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-6a-methyl-3a,4,5,6-tetrahydro-3H-cyclopenta[b]furan-2-one
—— (3R,4R)-3-methyl-4-(prop-1-en-2-yl)oxetan-2-one 1227673-07-5 C7H10O2
(3R,4R)-3-methyl-4-(prop-1-en-2-yl)oxetan-2-one
—— 2-hydroxy-4-phenyl-4-butyrolactone 13983-60-3 C10H10O3
2-hydroxy-4-phenyl-4-butyrolactone
—— S-[(2S,4R)-2-(chloromethyl)-6-oxooxan-4-yl] ethanethioate 914800-58-1 C8H11ClO3S
S-[(2S,4R)-2-(chloromethyl)-6-oxooxan-4-yl] ethanethioate
—— (R)-4-propyloxetan-2-one 170501-87-8 C6H10O2
(R)-4-propyloxetan-2-one
—— 4-Ethyl-4-decanolide 52935-94-1 C12H22O2
4-Ethyl-4-decanolide
—— methylketene dimer 476365-41-0 C6H8O2
methylketene dimer
—— (S)-5-((E)-3-iodo-2-methylallyl)dihydrofuran-2-one 404356-75-8 C8H11IO2
(S)-5-((E)-3-iodo-2-methylallyl)dihydrofuran-2-one
—— 4-(2-methylpropyl)oxetan-2-one 15890-56-9 C7H12O2
4-(2-methylpropyl)oxetan-2-one
—— 3R-benzyl-4R-isopropyldihydrofuran-2-one 313653-66-6 C14H18O2
3R-benzyl-4R-isopropyldihydrofuran-2-one
—— 5-methyl-3-[(E)-hexylidene]dihydrofuran-2(5H)-one 111572-43-1 C11H18O2
5-methyl-3-[(E)-hexylidene]dihydrofuran-2(5H)-one
—— (Z)-3-hexylidene-5-methyl-dihydro-furan-2-one 111572-44-2 C11H18O2
(Z)-3-hexylidene-5-methyl-dihydro-furan-2-one
—— (3R,4S)-3-methoxycarbonyl-4-pentyl-γ-butyrolactone 142235-91-4 C11H18O4
(3R,4S)-3-methoxycarbonyl-4-pentyl-γ-butyrolactone
—— 3-spiro[2'-(1',3',3a',4',5',7a'-hexahydro-6',7'-dimethyl)indenyl]furan-(5H)-2,4-dione 1193305-06-4 C14H18O3
3-spiro[2'-(1',3',3a',4',5',7a'-hexahydro-6',7'-dimethyl)indenyl]furan-(5H)-2,4-dione
—— 3-benzyl-3-(difluoromethyl)dihydrofuran-2(3H)-one 1364569-29-8 C12H12F2O2
3-benzyl-3-(difluoromethyl)dihydrofuran-2(3H)-one
—— 3-benzyltetrahydrofuran-2-one 61129-28-0 C11H12O2
3-benzyltetrahydrofuran-2-one
—— 3-benzyltetrahydro-2H-pyran-2-one 32821-74-2 C12H14O2
3-benzyltetrahydro-2H-pyran-2-one
—— 6-Ethyl-6-methyl-dihydro-pyran-2,4-dione 119523-85-2 C8H12O3
6-Ethyl-6-methyl-dihydro-pyran-2,4-dione
—— hexafluoro-dihydro-furan-2-one 702-35-2 C4F6O2
hexafluoro-dihydro-furan-2-one
—— (4R,6R)-6-[(3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yloxy]-4-phenyl-1,3-oxazinan-2-one 828253-37-8 C16H19NO5
(4R,6R)-6-[(3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yloxy]-4-phenyl-1,3-oxazinan-2-one
—— dihydro-5-methyl-5-<(phenylseleno)methyl>-2(3H)-furanone 75826-35-6 C12H14O2Se
dihydro-5-methyl-5-<(phenylseleno)methyl>-2(3H)-furanone
—— 5-(bromomethyl)-5-(methyl)dihydrofuran-2(3H)-one 130505-95-2 C6H9BrO2
5-(bromomethyl)-5-(methyl)dihydrofuran-2(3H)-one
—— (2-methyl-5-oxo-tetrahydro-[2]furyl)-acetic acid 129250-82-4 C7H10O4
(2-methyl-5-oxo-tetrahydro-[2]furyl)-acetic acid
—— 6-(tert-butyldimethylsilyloxymethyl)-4-hydroxy-δ-lactone 149013-39-8 C12H24O4Si
6-(tert-butyldimethylsilyloxymethyl)-4-hydroxy-δ-lactone
—— α,β-dimethyl-β,γ-dihydroxy-γ-phenylbutyrolactone 104865-47-6 C12H14O4
α,β-dimethyl-β,γ-dihydroxy-γ-phenylbutyrolactone
—— 2-methyl-4-butylbutyrolactone 40556-69-2 C9H16O2
2-methyl-4-butylbutyrolactone
—— 3-octyl-γ-butyrolactone 73262-43-8 C13H24O2
3-octyl-γ-butyrolactone
—— 2-Bromo-propionic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 690271-97-7 C9H13BrO4
2-Bromo-propionic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
—— (S)-3-[(2 R,3 R)-3-(tert-butyldimethylsilyloxy)-4,4-dimethyl-5-oxotetrahydrofuran-2-yl]-3-methoxypropanal 1200115-43-0 C16H30O5Si
(S)-3-[(2 R,3 R)-3-(tert-butyldimethylsilyloxy)-4,4-dimethyl-5-oxotetrahydrofuran-2-yl]-3-methoxypropanal
—— 3,6-Dioxatricyclo[3.3.1.02,4]nonan-7-one 89639-84-9 C7H8O3
3,6-Dioxatricyclo[3.3.1.02,4]nonan-7-one
—— (4R,5R)-4-(tert-butyldimethylsilyloxy)-5-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methylhex-5-enyl)-3,3-dimethyl dihydrofuran-2(3H)-one 1253891-05-2 C20H38O5Si
(4R,5R)-4-(tert-butyldimethylsilyloxy)-5-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methylhex-5-enyl)-3,3-dimethyl dihydrofuran-2(3H)-one
—— 4-(2-methoxy-ethyl)-2-oxa-bicyclo[2.2.2]octan-3-one 1292278-46-6 C10H16O3
4-(2-methoxy-ethyl)-2-oxa-bicyclo[2.2.2]octan-3-one
—— (3R,5R,6S)-6-methyl-3-hydroxy-5-(hydroxyethyl)-3,4,5-trihydrofuran-2-one 73679-22-8 C6H10O4
(3R,5R,6S)-6-methyl-3-hydroxy-5-(hydroxyethyl)-3,4,5-trihydrofuran-2-one
—— γ-ethyl-α-vinyl-γ-butyrolactone 62668-21-7 C8H12O2
γ-ethyl-α-vinyl-γ-butyrolactone
—— 5,5-dimethyl-4-(3-semicarbazono-butyl)-dihydro-furan-2-one 105640-56-0 C11H19N3O3
5,5-dimethyl-4-(3-semicarbazono-butyl)-dihydro-furan-2-one
—— (5R)-5-(triphenylsilylmethyl)oxolan-2-one 936005-46-8 C23H22O2Si
(5R)-5-(triphenylsilylmethyl)oxolan-2-one
—— (5R)-3-[(E)-1-hydroxybut-2-enyl]-5-(triphenylsilylmethyl)oxolan-2-one 936005-47-9 C27H28O3Si
(5R)-3-[(E)-1-hydroxybut-2-enyl]-5-(triphenylsilylmethyl)oxolan-2-one
—— 4-methyl-2-oxobutyrolactone 1944-45-2 C5H6O3
4-methyl-2-oxobutyrolactone
—— 4-bromo-4-(2,2,2-trichloroethyl)oxetan-2-one 81189-94-8 C5H4BrCl3O2
4-bromo-4-(2,2,2-trichloroethyl)oxetan-2-one
—— 4-chloro-4-chloromethyloxetan-2-one 84200-22-6 C4H4Cl2O2
4-chloro-4-chloromethyloxetan-2-one
—— 2,3,4,5-Tetrahydro-3-methyl-2-oxo-4-vinylfuran 78657-18-8 C7H10O2
2,3,4,5-Tetrahydro-3-methyl-2-oxo-4-vinylfuran
—— 1,4-dimethyl-6,8-dioxa-bicyclo[3.2.1]octan-7-one 13434-06-5 C8H12O3
1,4-dimethyl-6,8-dioxa-bicyclo[3.2.1]octan-7-one