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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
—— 3-Dimethoxyphosphinothioyloxolan-2-one —— C6H11O4PS
3-Dimethoxyphosphinothioyloxolan-2-one
—— (4S)-4-amino-1,2,6-trioxaspiro[2.4]heptan-7-one —— C4H5NO4
(4S)-4-amino-1,2,6-trioxaspiro[2.4]heptan-7-one
—— 1-(4,4-Dimethylpentan-2-yl)-3-oxabicyclo[3.1.0]hexan-2-one —— C12H20O2
1-(4,4-Dimethylpentan-2-yl)-3-oxabicyclo[3.1.0]hexan-2-one
—— (2R)-2-[(2S,3S,4S)-5-oxo-3,4-bis(trimethylsilyloxy)oxolan-2-yl]-2-trimethylsilyloxyacetaldehyde —— C15H32O6Si3
(2R)-2-[(2S,3S,4S)-5-oxo-3,4-bis(trimethylsilyloxy)oxolan-2-yl]-2-trimethylsilyloxyacetaldehyde
—— (3S,4R,5S)-5-[(1S)-1,2-bis(trimethylsilyloxy)ethyl]-3,4-bis(trimethylsilyloxy)oxolan-2-one —— C18H42O6Si4
(3S,4R,5S)-5-[(1S)-1,2-bis(trimethylsilyloxy)ethyl]-3,4-bis(trimethylsilyloxy)oxolan-2-one
—— Filifolide A 50585-61-0 C10H14O2
Filifolide A
—— (3E)-3-(hydroxymethylidene)-6-methyloxan-2-one —— C7H10O3
(3E)-3-(hydroxymethylidene)-6-methyloxan-2-one
—— Methyl 1,3-dimethyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-ene-10-carboxylate —— C13H16O4
Methyl 1,3-dimethyl-5-oxo-4-oxatricyclo[4.3.1.03,7]dec-8-ene-10-carboxylate
—— (1R,2R,6E)-7-methyl-3-methylidene-5,13-dioxatricyclo[9.2.1.02,6]tetradec-6-ene-4,12-dione —— C14H16O4
(1R,2R,6E)-7-methyl-3-methylidene-5,13-dioxatricyclo[9.2.1.02,6]tetradec-6-ene-4,12-dione
—— 3-(1-Ethenyl-2-oxopyrrolidin-1-ium-1-yl)-2-methylprop-2-enoic acid;3-methylideneoxolan-2-one —— C15H20NO5+
3-(1-Ethenyl-2-oxopyrrolidin-1-ium-1-yl)-2-methylprop-2-enoic acid;3-methylideneoxolan-2-one
—— 3-(1-Ethenyl-2-oxopyrrolidin-1-ium-1-yl)-2-methylprop-2-enoic acid;5-methyl-3-methylideneoxolan-2-one —— C16H22NO5+
3-(1-Ethenyl-2-oxopyrrolidin-1-ium-1-yl)-2-methylprop-2-enoic acid;5-methyl-3-methylideneoxolan-2-one
—— 4-Buta-1,3-dienyl-3-methylideneoxolan-2-one —— C9H10O2
4-Buta-1,3-dienyl-3-methylideneoxolan-2-one
—— (4S,6R)-6-Ethyl-4-methyl-tetrahydro-pyran-2-one —— C8H14O2
(4S,6R)-6-Ethyl-4-methyl-tetrahydro-pyran-2-one
—— (3S,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one —— C6H9ClO4
(3S,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
—— (3S,4R,5R)-3-chloro-5-ethyl-3,4-dimethyloxolan-2-one —— C8H13ClO2
(3S,4R,5R)-3-chloro-5-ethyl-3,4-dimethyloxolan-2-one
—— (5R)-5-amino-5-[(1S)-1-aminooxy-2-nitrosoethyl]oxolane-2,3,4-trione —— C6H7N3O6
(5R)-5-amino-5-[(1S)-1-aminooxy-2-nitrosoethyl]oxolane-2,3,4-trione
—— (4S,5S)-4-phenyl-5-thiophen-2-yl-5-(trifluoromethyl)oxolan-2-one —— C15H11F3O2S
(4S,5S)-4-phenyl-5-thiophen-2-yl-5-(trifluoromethyl)oxolan-2-one
—— 3-(Aminomethyl)-3-methyloxolan-2-one —— C6H11NO2
3-(Aminomethyl)-3-methyloxolan-2-one
—— 1,1-Difluoro-2-[[4-(2-hydroxyethyl)-3-oxo-2-oxabicyclo[3.1.0]hexan-6-yl]oxy]-2-oxoethanesulfonic acid —— C9H10F2O8S
1,1-Difluoro-2-[[4-(2-hydroxyethyl)-3-oxo-2-oxabicyclo[3.1.0]hexan-6-yl]oxy]-2-oxoethanesulfonic acid
—— 6-Hexyl-3-pentyloxepan-2-one —— C17H32O2
6-Hexyl-3-pentyloxepan-2-one
—— 3-Nonyloxepan-2-one —— C15H28O2
3-Nonyloxepan-2-one
—— 6-Decyl-3-nonyloxepan-2-one —— C25H48O2
6-Decyl-3-nonyloxepan-2-one
—— 3-Methyloxolan-2-one;4-methyloxolan-2-one —— C10H16O4
3-Methyloxolan-2-one;4-methyloxolan-2-one
—— But-3-enoic acid;oxepan-2-one —— C10H16O4
But-3-enoic acid;oxepan-2-one
—— (3S,4S,6S)-3,4-dibutoxy-6-(butoxymethyl)oxan-2-one —— C18H34O5
(3S,4S,6S)-3,4-dibutoxy-6-(butoxymethyl)oxan-2-one
—— (3R,4S)-3,4-dibutoxy-6-(butoxymethyl)oxan-2-one —— C18H34O5
(3R,4S)-3,4-dibutoxy-6-(butoxymethyl)oxan-2-one
—— (3R,4S,6S)-3,4-dibutoxy-6-(butoxymethyl)oxan-2-one —— C18H34O5
(3R,4S,6S)-3,4-dibutoxy-6-(butoxymethyl)oxan-2-one
—— (3R,4S,6R)-6-ethyl-3,4-dimethyloxan-2-one —— C9H16O2
(3R,4S,6R)-6-ethyl-3,4-dimethyloxan-2-one
—— 5-hydroxy-5-pentanedihydrofuran-2(3H)-one —— C9H16O3
5-hydroxy-5-pentanedihydrofuran-2(3H)-one
—— (3-Oxo-2-oxatricyclo[3.3.1.11,4]decan-6-yl) prop-2-enoate —— C12H14O4
(3-Oxo-2-oxatricyclo[3.3.1.11,4]decan-6-yl) prop-2-enoate
—— 3,4-Bis(prop-2-enyl)oxane-2,6-dione —— C11H14O3
3,4-Bis(prop-2-enyl)oxane-2,6-dione
—— 3,5-Bis(prop-2-enyl)oxane-2,6-dione —— C11H14O3
3,5-Bis(prop-2-enyl)oxane-2,6-dione
—— 4-(2-Methylbutyl)oxane-2,6-dione —— C10H16O3
4-(2-Methylbutyl)oxane-2,6-dione
—— 3,3-Dimethyloxolan-2-one;prop-2-enoic acid —— C9H14O4
3,3-Dimethyloxolan-2-one;prop-2-enoic acid
—— 3,4,6-Trimethyloxepane-2,7-dione —— C9H14O3
3,4,6-Trimethyloxepane-2,7-dione
—— (1R,5S,9R,13R)-13-(methoxymethyl)-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-8-one —— C21H32O3
(1R,5S,9R,13R)-13-(methoxymethyl)-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-8-one
—— (1S,5S,9R,11S,13S)-11-methoxy-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-8-one —— C21H32O3
(1S,5S,9R,11S,13S)-11-methoxy-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-8-one
—— (3α,5α,17β)-17-hydroxymethyl-19-methoxy-3-(methoxymethoxy)-androstan-18-oic acid γ-lactone —— C23H36O5
(3α,5α,17β)-17-hydroxymethyl-19-methoxy-3-(methoxymethoxy)-androstan-18-oic acid γ-lactone
—— (1R,2S,5S,9R,12S,13S,18R)-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-8-one —— C20H30O2
(1R,2S,5S,9R,12S,13S,18R)-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosan-8-one
—— (4-Cyano-3-oxo-4-propyl-2-oxabicyclo[3.2.0]heptan-7-yl) 2,2-dimethylpropanoate —— C15H21NO4
(4-Cyano-3-oxo-4-propyl-2-oxabicyclo[3.2.0]heptan-7-yl) 2,2-dimethylpropanoate
—— [(1R)-5-oxo-4-oxatricyclo[4.3.1.03,10]decan-2-yl] 2,2-dimethylbutanoate —— C15H22O4
[(1R)-5-oxo-4-oxatricyclo[4.3.1.03,10]decan-2-yl] 2,2-dimethylbutanoate
—— (1S,3S,5S)-3-amino-1-ethoxy-6-oxabicyclo[3.2.1]octan-7-one —— C9H15NO3
(1S,3S,5S)-3-amino-1-ethoxy-6-oxabicyclo[3.2.1]octan-7-one
—— (5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-6-[2-[hydroxy(dimethyl)silyl]-2-methylpropyl]-2-oxabicyclo[2.2.1]heptan-3-one —— C18H36O4Si2
(5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-6-[2-[hydroxy(dimethyl)silyl]-2-methylpropyl]-2-oxabicyclo[2.2.1]heptan-3-one
—— (3R,4S,6R)-5-methyl-6-trimethylsilyl-3,4-bis(trimethylsilyloxy)oxan-2-one —— C15H34O4Si3
(3R,4S,6R)-5-methyl-6-trimethylsilyl-3,4-bis(trimethylsilyloxy)oxan-2-one
—— methyl 2,2-dimethyl-3-[(Z)-(2-oxooxolan-3-ylidene)methyl]cyclopropane-1-carboxylate —— C12H16O4
methyl 2,2-dimethyl-3-[(Z)-(2-oxooxolan-3-ylidene)methyl]cyclopropane-1-carboxylate
—— propan-2-yl 2,2-dimethyl-3-[(Z)-(2-oxooxolan-3-ylidene)methyl]cyclopropane-1-carboxylate —— C14H20O4
propan-2-yl 2,2-dimethyl-3-[(Z)-(2-oxooxolan-3-ylidene)methyl]cyclopropane-1-carboxylate
—— 1-(2-Oxooxan-3-yl)butan-2-yl acetate —— C11H18O4
1-(2-Oxooxan-3-yl)butan-2-yl acetate
—— (5R)-5-hydroxy-3-propyloxolan-2-one —— C7H12O3
(5R)-5-hydroxy-3-propyloxolan-2-one
—— 5,9-Dioxatricyclo[5.2.1.03,8]decan-4-one —— C8H10O3
5,9-Dioxatricyclo[5.2.1.03,8]decan-4-one
—— (4R)-4-methyl-5-[(3S)-2-oxopentan-3-yl]oxolan-2-one —— C10H16O3
(4R)-4-methyl-5-[(3S)-2-oxopentan-3-yl]oxolan-2-one