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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,5R)-5-hexyl-3-methyloxolan-2-one —— C11H20O2
(3S,5R)-5-hexyl-3-methyloxolan-2-one
—— (3E)-3-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethylidene]oxolan-2-one —— C15H22O2
(3E)-3-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethylidene]oxolan-2-one
—— ethyl (2R,3S)-2-ethyl-3-methyl-4,5-dioxooxolane-3-carboxylate —— C10H14O5
ethyl (2R,3S)-2-ethyl-3-methyl-4,5-dioxooxolane-3-carboxylate
—— (3S,5S,6S)-3,6-dimethyl-1-oxaspiro[4.5]decan-2-one —— C11H18O2
(3S,5S,6S)-3,6-dimethyl-1-oxaspiro[4.5]decan-2-one
—— (3S,5R,6S)-3,6-dimethyl-1-oxaspiro[4.5]decan-2-one —— C11H18O2
(3S,5R,6S)-3,6-dimethyl-1-oxaspiro[4.5]decan-2-one
—— (3S,5R,6R)-3,6-dimethyl-1-oxaspiro[4.5]decan-2-one —— C11H18O2
(3S,5R,6R)-3,6-dimethyl-1-oxaspiro[4.5]decan-2-one
—— lactone of 1,1-dioxo-3-hydroxythiolan-4-ylacetic acid 17236-01-0 C6H8O4S
lactone of 1,1-dioxo-3-hydroxythiolan-4-ylacetic acid
—— (6R,9aR)-6-methyl-1,5,6,7,9,9a-hexahydrocycloocta[c]furan-3,8-dione —— C11H14O3
(6R,9aR)-6-methyl-1,5,6,7,9,9a-hexahydrocycloocta[c]furan-3,8-dione
—— (4R,5S)-4-bromo-5-ethoxyoxolan-2-one —— C6H9BrO3
(4R,5S)-4-bromo-5-ethoxyoxolan-2-one
—— (3S)-3-acetyl-3-prop-2-ynyloxolan-2-one —— C9H10O3
(3S)-3-acetyl-3-prop-2-ynyloxolan-2-one
—— Majorenolide —— C17H28O3
Majorenolide
—— (-)-(2Z,3R,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methylbutanolide 1196997-40-6 C17H26O3
(-)-(2Z,3R,4S)-2-(dodec-11-ynylidene)-3-hydroxy-4-methylbutanolide
—— (2S,3R)-4-Methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid benzylamide —— C21H29NO3
(2S,3R)-4-Methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid benzylamide
—— 2-[[(2S,3R)-4-methylene-2-octyl-5-oxo-tetrahydrofuran-3-carbonyl]amino]ethyl N-allylcarbamate —— C20H32N2O5
2-[[(2S,3R)-4-methylene-2-octyl-5-oxo-tetrahydrofuran-3-carbonyl]amino]ethyl N-allylcarbamate
—— (5Z,9Z)-5,9-dimethyl-1-oxacycloundeca-5,9-dien-2-one —— C12H18O2
(5Z,9Z)-5,9-dimethyl-1-oxacycloundeca-5,9-dien-2-one
—— 3-(2-tert-Butoxyethylidene)-5-((tert-butyl(dimethyl)silyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one —— C19H34O4Si
3-(2-tert-Butoxyethylidene)-5-((tert-butyl(dimethyl)silyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
—— 1a,5,9-Trimethyl-13-methylene-12-oxo-1a,2,3,6,7,8,9,10,10a,12,13,13a,14,14a-tetradecahydrooxireno[2',3':4,5]cyclotetradeca[1,2-b]furan-10-yl acetate —— C22H32O5
1a,5,9-Trimethyl-13-methylene-12-oxo-1a,2,3,6,7,8,9,10,10a,12,13,13a,14,14a-tetradecahydrooxireno[2',3':4,5]cyclotetradeca[1,2-b]furan-10-yl acetate
—— 4,6-Epoxy-6-epideacetyllaurenobiolide —— C14H18O4
4,6-Epoxy-6-epideacetyllaurenobiolide
—— [(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-(6-oxooxan-2-yl)trideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate —— C19H29O9P
[(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-(6-oxooxan-2-yl)trideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate
—— Cyclohexyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C16H24O4
Cyclohexyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (3R,5R)-5-butyl-5-ethyl-3-methyloxolan-2-one —— C11H20O2
(3R,5R)-5-butyl-5-ethyl-3-methyloxolan-2-one
—— ethyl (2R,4S)-4-acetyl-5-oxooxolane-2-carboxylate —— C9H12O5
ethyl (2R,4S)-4-acetyl-5-oxooxolane-2-carboxylate
—— (3S,5S)-3-acetyl-5-ethenyloxolan-2-one —— C8H10O3
(3S,5S)-3-acetyl-5-ethenyloxolan-2-one
—— ethyl (2S,4R)-4-acetyl-5-oxooxolane-2-carboxylate —— C9H12O5
ethyl (2S,4R)-4-acetyl-5-oxooxolane-2-carboxylate
—— N-cycloheptyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H27NO3
N-cycloheptyl-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— N-benzyl-4,7,7-trimethyl-3-oxo-N-(pyridin-2-yl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C22H24N2O3
N-benzyl-4,7,7-trimethyl-3-oxo-N-(pyridin-2-yl)-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,6R,8R)-2,2,6-trimethylspiro[3-oxabicyclo[4.2.0]octane-8,2'-oxirane]-4-one —— C11H16O3
(1R,6R,8R)-2,2,6-trimethylspiro[3-oxabicyclo[4.2.0]octane-8,2'-oxirane]-4-one
—— 2-Hydroxyethyl prop-2-enoate;5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane;oxepan-2-one —— C23H36N2O7
2-Hydroxyethyl prop-2-enoate;5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane;oxepan-2-one
—— Malonic dilactone, alpha-[2-(diethylamino)ethyl]-cis-1(me),3(h),4(h)-cis-3(h)-1,8-dihydroxy-3-p-menthyl —— C19H31NO4
Malonic dilactone, alpha-[2-(diethylamino)ethyl]-cis-1(me),3(h),4(h)-cis-3(h)-1,8-dihydroxy-3-p-menthyl
—— Malonic dilactone, alpha-[2-(morpholino)ethyl]-cis-1(me),3(h),4(h)-cis-3(h)-1,8-dihydroxy-3-p-menthyl —— C19H29NO5
Malonic dilactone, alpha-[2-(morpholino)ethyl]-cis-1(me),3(h),4(h)-cis-3(h)-1,8-dihydroxy-3-p-menthyl
—— Cyclohexanemalonic acid, 5-hydroxy-2-(1-hydroxyethyl)-4,4-dimethyl-alpha-[1-(dimethylamino)prop-2-yl]-gamma,delta-dilactone —— C18H29NO4
Cyclohexanemalonic acid, 5-hydroxy-2-(1-hydroxyethyl)-4,4-dimethyl-alpha-[1-(dimethylamino)prop-2-yl]-gamma,delta-dilactone
—— Cyclohexanemalonic acid, 4,4-dimethyl-alpha-hydroxy-2-(1-hydroxyethyl)-,gamma,delta-dilactone —— C13H18O4
Cyclohexanemalonic acid, 4,4-dimethyl-alpha-hydroxy-2-(1-hydroxyethyl)-,gamma,delta-dilactone
—— Mevalonolactone, diTMS —— C12H26O4Si2
Mevalonolactone, diTMS
—— ethyl (2R,3S)-2-oxo-5-phenyltetrahydrofuran-3-carboxylate —— C13H14O4
ethyl (2R,3S)-2-oxo-5-phenyltetrahydrofuran-3-carboxylate
—— (4S)-4-(3-oxobutyl)oxetan-2-one —— C7H10O3
(4S)-4-(3-oxobutyl)oxetan-2-one
—— ethyl (3S,5R)-2-oxo-5-phenyloxolane-3-carboxylate —— C13H14O4
ethyl (3S,5R)-2-oxo-5-phenyloxolane-3-carboxylate
—— 2-Deoxy-threo-pentonic acid, 1,4-lactone, TMS —— C11H24O4Si2
2-Deoxy-threo-pentonic acid, 1,4-lactone, TMS
—— 6-Deoxygalactonic acid, 1,4-lactone, TMS —— C15H34O5Si3
6-Deoxygalactonic acid, 1,4-lactone, TMS
—— Threonic acid, 1,4-lactone, TMS —— C10H22O4Si2
Threonic acid, 1,4-lactone, TMS
—— (3S,5R)-3-trimethylsilyloxy-3,5-bis(trimethylsilyloxymethyl)oxolan-2-one —— C15H34O5Si3
(3S,5R)-3-trimethylsilyloxy-3,5-bis(trimethylsilyloxymethyl)oxolan-2-one
—— 2-Deoxy-erythro-pentonic acid, 1,4-lactone, TMS —— C11H24O4Si2
2-Deoxy-erythro-pentonic acid, 1,4-lactone, TMS
—— (3R,4R)-3,4-Bis-trimethylsilanyloxy-dihydro-furan-2-one 32384-52-4 C10H22O4Si2
(3R,4R)-3,4-Bis-trimethylsilanyloxy-dihydro-furan-2-one
—— 2,6-Dideoxy-ribo-hexonic acid, 1,4-lactone, TMS —— C12H26O4Si2
2,6-Dideoxy-ribo-hexonic acid, 1,4-lactone, TMS
—— 3,5-Dideoxy-erythro-pentonic acid, 1,4-lactone, TMS —— C8H16O3Si
3,5-Dideoxy-erythro-pentonic acid, 1,4-lactone, TMS
—— 3-Deoxy-erythro-pentonic acid, 1,4-lactone, TMS —— C11H24O4Si2
3-Deoxy-erythro-pentonic acid, 1,4-lactone, TMS
—— (3S,5S)-3-Trimethylsilanyloxy-3,5-bis-trimethylsilanyloxymethyl-dihydro-furan-2-one 34641-57-1 C15H34O5Si3
(3S,5S)-3-Trimethylsilanyloxy-3,5-bis-trimethylsilanyloxymethyl-dihydro-furan-2-one
—— 3-Deoxy-xylo-hexonic acid, 1,4-lactone, TMS —— C15H34O5Si3
3-Deoxy-xylo-hexonic acid, 1,4-lactone, TMS
—— (3R,4R,5S)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-one —— C14H32O5Si3
(3R,4R,5S)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-one
—— 6-Deoxymannonic acid, 1,4-lactone, TMS —— C15H34O5Si3
6-Deoxymannonic acid, 1,4-lactone, TMS
—— 3-Deoxy-threo-pentonic acid, 1,4-lactone, TMS —— C11H24O4Si2
3-Deoxy-threo-pentonic acid, 1,4-lactone, TMS