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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
—— (1S,2S,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid —— C10H14O4
(1S,2S,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
—— (1S,2S,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid —— C10H14O4
(1S,2S,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
—— (1S,4S)-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one —— C12H12O2
(1S,4S)-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one
—— [(2S)-pent-4-yn-2-yl] (1S,2R,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C15H20O4
[(2S)-pent-4-yn-2-yl] (1S,2R,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— [(2S)-pent-4-yn-2-yl] (1S,2S,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C15H20O4
[(2S)-pent-4-yn-2-yl] (1S,2S,3R,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— [(2S)-pent-4-yn-2-yl] (1S,2R,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C15H20O4
[(2S)-pent-4-yn-2-yl] (1S,2R,3S,5R)-3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— [(3S,3aS,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate —— C17H20O5
[(3S,3aS,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate
—— (1S,4S,7S)-7-methyl-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one —— C13H14O2
(1S,4S,7S)-7-methyl-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one
—— (1S,4S,7R)-7-methyl-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one —— C13H14O2
(1S,4S,7R)-7-methyl-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one
—— (3R,5S)-3,5-diacetyloxane-2,4,6-trione —— C9H8O6
(3R,5S)-3,5-diacetyloxane-2,4,6-trione
—— (3E)-3-[2-[(1R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one —— C20H30O5
(3E)-3-[2-[(1R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
—— (3R,5R)-3,5-diacetyloxane-2,4,6-trione —— C9H8O6
(3R,5R)-3,5-diacetyloxane-2,4,6-trione
—— (3S,5S)-3,5-diacetyloxane-2,4,6-trione —— C9H8O6
(3S,5S)-3,5-diacetyloxane-2,4,6-trione
—— 4,6-Ethano-1h,8h-pyrano[3,4-c]pyran-1,8-dione, hexahydro-3,3,6-trimethyl-8a-[2-(dimethylamino)ethyl]- —— C17H27NO4
4,6-Ethano-1h,8h-pyrano[3,4-c]pyran-1,8-dione, hexahydro-3,3,6-trimethyl-8a-[2-(dimethylamino)ethyl]-
—— Mevalonolactone TBDMS —— C18H38O4Si2
Mevalonolactone TBDMS
—— (3R,4S,5R)-3-methyl-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-one —— C15H34O5Si3
(3R,4S,5R)-3-methyl-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-one
—— (1S,4S)-4,7,7-trimethyl-3-oxo-N-prop-2-enyl-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C13H19NO3
(1S,4S)-4,7,7-trimethyl-3-oxo-N-prop-2-enyl-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (3R,5R)-3,5-diphenyloxane-2,6-dione —— C17H14O3
(3R,5R)-3,5-diphenyloxane-2,6-dione
—— (3S,5S)-3,5-diphenyloxane-2,6-dione —— C17H14O3
(3S,5S)-3,5-diphenyloxane-2,6-dione
—— (3Z)-3-[1-(methylamino)ethylidene]-5-phenyloxolane-2,4-dione —— C13H13NO3
(3Z)-3-[1-(methylamino)ethylidene]-5-phenyloxolane-2,4-dione
—— (1R,4R,8S,9S)-1,7,7-trimethyl-2,6-dioxatricyclo[6.2.2.04,9]dodecane-3,5-dione —— C13H18O4
(1R,4R,8S,9S)-1,7,7-trimethyl-2,6-dioxatricyclo[6.2.2.04,9]dodecane-3,5-dione
—— (1S,5S,6S)-6-(2-hydroxypropan-2-yl)-1-methyl-2-oxabicyclo[3.3.1]nonan-3-one —— C12H20O3
(1S,5S,6S)-6-(2-hydroxypropan-2-yl)-1-methyl-2-oxabicyclo[3.3.1]nonan-3-one
—— (1R,4R,8R,9S)-1,7,7-trimethyl-2,6-dioxatricyclo[6.2.2.04,9]dodecane-3,5-dione —— C13H18O4
(1R,4R,8R,9S)-1,7,7-trimethyl-2,6-dioxatricyclo[6.2.2.04,9]dodecane-3,5-dione
—— (1S,5S,6R)-6-(2-hydroxypropan-2-yl)-1-methyl-2-oxabicyclo[3.3.1]nonan-3-one —— C12H20O3
(1S,5S,6R)-6-(2-hydroxypropan-2-yl)-1-methyl-2-oxabicyclo[3.3.1]nonan-3-one
—— (1S,4S)-4,7,7-trimethyl-1-(morpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one —— C14H21NO4
(1S,4S)-4,7,7-trimethyl-1-(morpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one
—— 3-(2-(6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl)ethylidene)dihydro-2(3H)-furanone —— C20H30O4
3-(2-(6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl)ethylidene)dihydro-2(3H)-furanone
—— Hydroxy-oxo-(5-oxooxolan-3-yl)phosphanium —— C4H6O4P+
Hydroxy-oxo-(5-oxooxolan-3-yl)phosphanium
—— (2R,4S,5S,7R,9S,13S,14S)-7-methyl-12-methylidene-3,6,10,15-tetraoxapentacyclo[12.2.1.02,4.05,7.09,13]heptadec-1(17)-ene-11,16-dione —— C15H14O6
(2R,4S,5S,7R,9S,13S,14S)-7-methyl-12-methylidene-3,6,10,15-tetraoxapentacyclo[12.2.1.02,4.05,7.09,13]heptadec-1(17)-ene-11,16-dione
—— (2R,4S,5S,7R,9R,13S,14S)-7-methyl-12-methylidene-3,6,10,15-tetraoxapentacyclo[12.2.1.02,4.05,7.09,13]heptadec-1(17)-ene-11,16-dione —— C15H14O6
(2R,4S,5S,7R,9R,13S,14S)-7-methyl-12-methylidene-3,6,10,15-tetraoxapentacyclo[12.2.1.02,4.05,7.09,13]heptadec-1(17)-ene-11,16-dione
—— [amino-[[(2R,4R)-5-oxo-4-propyloxolan-2-yl]methylsulfanyl]methylidene]azanium —— C9H17N2O2S+
[amino-[[(2R,4R)-5-oxo-4-propyloxolan-2-yl]methylsulfanyl]methylidene]azanium
—— (1S,5S)-3,8-dioxabicyclo[3.2.1]octane-2,4-dione —— C6H6O4
(1S,5S)-3,8-dioxabicyclo[3.2.1]octane-2,4-dione
—— (1R,5R)-3,8-dioxabicyclo[3.2.1]octane-2,4-dione —— C6H6O4
(1R,5R)-3,8-dioxabicyclo[3.2.1]octane-2,4-dione
—— (3S)-2,4-dioxooxolane-3-carbaldehyde —— C5H4O4
(3S)-2,4-dioxooxolane-3-carbaldehyde
—— (1R,5R)-6-oxabicyclo[3.2.2]nonan-7-one —— C8H12O2
(1R,5R)-6-oxabicyclo[3.2.2]nonan-7-one
—— (3R)-3-tert-butyloxolane-2,4-dione —— C8H12O3
(3R)-3-tert-butyloxolane-2,4-dione
—— (1R,6R,9S)-5,5,9-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-10-one —— C14H22O2
(1R,6R,9S)-5,5,9-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-10-one
—— (1S,4S)-2-oxabicyclo[2.2.1]heptan-3-one —— C6H8O2
(1S,4S)-2-oxabicyclo[2.2.1]heptan-3-one
—— (1S,5S)-6-oxabicyclo[3.2.2]nonan-7-one —— C8H12O2
(1S,5S)-6-oxabicyclo[3.2.2]nonan-7-one
—— (1R,6R)-7-oxabicyclo[4.2.2]decan-8-one —— C9H14O2
(1R,6R)-7-oxabicyclo[4.2.2]decan-8-one
—— (1R,4R)-2-oxabicyclo[2.2.1]heptan-3-one —— C6H8O2
(1R,4R)-2-oxabicyclo[2.2.1]heptan-3-one
—— (1R,6S,9S)-5,5,9-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-10-one —— C14H22O2
(1R,6S,9S)-5,5,9-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-10-one
—— (1R,2R,6R,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one —— C10H14O2
(1R,2R,6R,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one
—— (1R,2R,6S,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one —— C10H14O2
(1R,2R,6S,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one
—— (1R,2S,6R,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one —— C10H14O2
(1R,2S,6R,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one
—— (1R,2S,6S,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one —— C10H14O2
(1R,2S,6S,7S)-8-oxatricyclo[5.3.1.02,6]undecan-9-one
—— (3Z)-3-[1-(propylamino)ethylidene]oxolane-2,4-dione —— C9H13NO3
(3Z)-3-[1-(propylamino)ethylidene]oxolane-2,4-dione
—— (4Z,5S)-4-[hydroxy(phenyl)methylidene]-5-phenyloxolane-2,3-dione —— C17H12O4
(4Z,5S)-4-[hydroxy(phenyl)methylidene]-5-phenyloxolane-2,3-dione
—— (1R,5R)-3-oxabicyclo[3.3.1]nonane-2,4-dione —— C8H10O3
(1R,5R)-3-oxabicyclo[3.3.1]nonane-2,4-dione
—— (4Z,5R)-4-[hydroxy(phenyl)methylidene]-5-phenyloxolane-2,3-dione —— C17H12O4
(4Z,5R)-4-[hydroxy(phenyl)methylidene]-5-phenyloxolane-2,3-dione
—— methyl (1S,6S,9S)-8-oxo-7-oxabicyclo[4.2.1]nonane-9-carboxylate —— C10H14O4
methyl (1S,6S,9S)-8-oxo-7-oxabicyclo[4.2.1]nonane-9-carboxylate