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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
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-[(2S,3R)-2,3,4-trihydroxybutoxy]oxolane-2,3-dione —— C10H16O9
(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-[(2S,3R)-2,3,4-trihydroxybutoxy]oxolane-2,3-dione
—— 5-Methylbicyclo[2.2.1]hept-2-ene;(5-oxooxolan-3-yl) bicyclo[2.2.1]hept-5-ene-2-carboxylate —— C20H26O4
5-Methylbicyclo[2.2.1]hept-2-ene;(5-oxooxolan-3-yl) bicyclo[2.2.1]hept-5-ene-2-carboxylate
—— 6-Cyclopentyl-6-(3-phenylpropyl)oxane-2,4-dione —— C19H24O3
6-Cyclopentyl-6-(3-phenylpropyl)oxane-2,4-dione
—— (3S,4S)-3-((E)-Hex-2-enyl)-4-(2-oxo-tridecyl)-oxetan-2-one —— C22H38O3
(3S,4S)-3-((E)-Hex-2-enyl)-4-(2-oxo-tridecyl)-oxetan-2-one
—— 3-Ethyl-4,6-dimethyloxan-2-one —— C9H16O2
3-Ethyl-4,6-dimethyloxan-2-one
—— 3-[2-[1-Ethylsulfinyl-2-(2-hydroxyoxetan-3-yl)propyl]sulfinylethyl]oxetan-2-one —— C13H22O6S2
3-[2-[1-Ethylsulfinyl-2-(2-hydroxyoxetan-3-yl)propyl]sulfinylethyl]oxetan-2-one
—— (5R)-5-(hydroxymethyl)-3,4-dimethyloxolan-2-one —— C7H12O3
(5R)-5-(hydroxymethyl)-3,4-dimethyloxolan-2-one
—— Propan-2-yl 2-(5-oxooxolan-2-yl)acetate —— C9H14O4
Propan-2-yl 2-(5-oxooxolan-2-yl)acetate
—— (3aR,4R,5R,6aS)-5-benzylperoxy-4-[(3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C25H28O5
(3aR,4R,5R,6aS)-5-benzylperoxy-4-[(3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— 2-Methyl-2-propan-2-yl-5-oxatricyclo[5.2.1.04,8]decan-6-one —— C13H20O2
2-Methyl-2-propan-2-yl-5-oxatricyclo[5.2.1.04,8]decan-6-one
—— 5-(2,2-Dimethylpropyl)-6-ethylidene-3,5-dimethyloxan-2-one —— C14H24O2
5-(2,2-Dimethylpropyl)-6-ethylidene-3,5-dimethyloxan-2-one
—— (4-Oxo-5-oxatricyclo[4.4.0.03,9]decan-8-yl) 2-tert-butyl-2,4,4-trimethylpentanoate —— C21H34O4
(4-Oxo-5-oxatricyclo[4.4.0.03,9]decan-8-yl) 2-tert-butyl-2,4,4-trimethylpentanoate
—— Methyl 5-benzyl-2,4-dioxooxolane-3-carboxylate —— C13H12O5
Methyl 5-benzyl-2,4-dioxooxolane-3-carboxylate
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-3-pentoxyoxolane-2,4-dione —— C11H18O6
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3-pentoxyoxolane-2,4-dione
—— (14S,15S)-7-amino-14-ethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadeca-5(10),6-diene-15,5'-oxolane]-2'-one —— C24H31NO2
(14S,15S)-7-amino-14-ethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadeca-5(10),6-diene-15,5'-oxolane]-2'-one
—— 4-[3-(2,2-Dimethylpent-4-enoxy)-3-methylbutyl]-5-hydroxyoxolan-2-one —— C16H28O4
4-[3-(2,2-Dimethylpent-4-enoxy)-3-methylbutyl]-5-hydroxyoxolan-2-one
—— Ethane;oxolan-2-one —— C6H12O2
Ethane;oxolan-2-one
—— 6-[2-(4-Methyl-1,3-thiazol-5-yl)ethyl]-6-propan-2-yloxane-2,4-dione —— C14H19NO3S
6-[2-(4-Methyl-1,3-thiazol-5-yl)ethyl]-6-propan-2-yloxane-2,4-dione
—— (8-Methyl-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-1-yl) 1-(2,2-dimethylpropyl)-2,2-dimethylcyclopropane-1-carboxylate —— C22H34O4
(8-Methyl-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-1-yl) 1-(2,2-dimethylpropyl)-2,2-dimethylcyclopropane-1-carboxylate
—— 3-[4-[Tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]propanoic acid —— C14H26O5Si
3-[4-[Tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]propanoic acid
—— 6-Ethyl-3,4-dimethyloxan-2-one —— C9H16O2
6-Ethyl-3,4-dimethyloxan-2-one
—— 3-(4-Bromo-2-chlorophenyl)-6-methoxy-5,5-dimethyloxane-2,4-dione —— C14H14BrClO4
3-(4-Bromo-2-chlorophenyl)-6-methoxy-5,5-dimethyloxane-2,4-dione
—— Ethane;oxolan-2-one —— C10H24O2
Ethane;oxolan-2-one
—— 3-[(6R)-2,4-dioxo-6-(2-phenylethyl)-6-propyloxan-3-yl]propanoic acid —— C19H24O5
3-[(6R)-2,4-dioxo-6-(2-phenylethyl)-6-propyloxan-3-yl]propanoic acid
—— Trihydroxy-[4-(4-methyl-2-oxooxan-4-yl)oxy-2,4-dioxobutyl]phosphanium —— C10H16O8P+
Trihydroxy-[4-(4-methyl-2-oxooxan-4-yl)oxy-2,4-dioxobutyl]phosphanium
—— 5-Methyl-4-methylidene-5-(3-methyl-2-oxobut-3-enyl)-3-(2-methylprop-2-enylidene)oxolan-2-one —— C15H18O3
5-Methyl-4-methylidene-5-(3-methyl-2-oxobut-3-enyl)-3-(2-methylprop-2-enylidene)oxolan-2-one
—— 3-(5-Bromo-2-methylphenyl)-5,5,6,6-tetramethyloxane-2,4-dione —— C16H19BrO3
3-(5-Bromo-2-methylphenyl)-5,5,6,6-tetramethyloxane-2,4-dione
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-(1-hydroxypropan-2-ylperoxy)oxolane-2,3-dione —— C9H14O8
(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-(1-hydroxypropan-2-ylperoxy)oxolane-2,3-dione
—— Ethyl 3-(hydroxymethyl)-7,8-dioxo-2,3,5,8a-tetrahydro-[1,4]dithiepino[6,5-b]furan-5a-carboxylate —— C11H14O6S2
Ethyl 3-(hydroxymethyl)-7,8-dioxo-2,3,5,8a-tetrahydro-[1,4]dithiepino[6,5-b]furan-5a-carboxylate
—— 5-(1,2-Dihydroxyethyl)-4-methyloxolane-2,3-dione —— C7H10O5
5-(1,2-Dihydroxyethyl)-4-methyloxolane-2,3-dione
—— 10-(α-Hydroxy-α-methylbenzyl)-9-carboxy-Δ<sup>4a(4b)</sup>-dodecahydro-phenanthren-lacton 13823-78-4 C23H28O2
10-(α-Hydroxy-α-methylbenzyl)-9-carboxy-Δ<sup>4a(4b)</sup>-dodecahydro-phenanthren-lacton
—— 4-Methyl-4-(3,4,7-trimethyl-1-adamantyl)oxetan-2-one —— C17H26O2
4-Methyl-4-(3,4,7-trimethyl-1-adamantyl)oxetan-2-one
—— (5S)-3-prop-2-enyl-5-propyloxolane-2,4-dione —— C10H14O3
(5S)-3-prop-2-enyl-5-propyloxolane-2,4-dione
—— 2,3a-Dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one —— C7H10O4
2,3a-Dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-(2-hydroxy-3-methylpentoxy)oxolane-2,3-dione —— C12H20O7
(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-(2-hydroxy-3-methylpentoxy)oxolane-2,3-dione
—— (1R,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptan-4-one —— C8H12O2
(1R,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptan-4-one
—— 1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic Acid —— C6H5BrO4
1-bromo-4-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylic Acid
—— Ethane;6-oxabicyclo[3.2.1]octan-7-one —— C9H16O2
Ethane;6-oxabicyclo[3.2.1]octan-7-one
—— (5S)-3-hexylidene-5-methyloxolan-2-one —— C11H18O2
(5S)-3-hexylidene-5-methyloxolan-2-one
—— 2-Butoxyethyl 3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C16H26O5
2-Butoxyethyl 3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— 6-Methylheptan-2-yl 3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C18H30O4
6-Methylheptan-2-yl 3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— 6-Chlorohexyl 3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate —— C16H25ClO4
6-Chlorohexyl 3,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate
—— (3S,4R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one —— C6H10O6
(3S,4R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
—— 3-[C-methyl-N-(2-phenylethyl)carbonimidoyl]oxolan-2-one —— C14H17NO2
3-[C-methyl-N-(2-phenylethyl)carbonimidoyl]oxolan-2-one
—— (1S,5R,6R)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxamide —— C12H11NO3
(1S,5R,6R)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxamide
—— 1-Oxacycloundec-5-en-2-one —— C10H16O2
1-Oxacycloundec-5-en-2-one
—— alpha-Methyl-alpha-pentyl-beta-propiolactone —— C9H16O2
alpha-Methyl-alpha-pentyl-beta-propiolactone
—— (3S,4R,5S,6R)-4,6-dihydroxy-3,5,7-trimethyloxepan-2-one —— C9H16O4
(3S,4R,5S,6R)-4,6-dihydroxy-3,5,7-trimethyloxepan-2-one
—— 3-(Tert-butyl-hexa-2,4-dien-3-yl-phenylsilyl)oxyoxolan-2-one —— C20H28O3Si
3-(Tert-butyl-hexa-2,4-dien-3-yl-phenylsilyl)oxyoxolan-2-one
—— 5-(1,2-Dimethoxyethyl)-4-hydroxyoxolane-2,3-dione —— C8H12O6
5-(1,2-Dimethoxyethyl)-4-hydroxyoxolane-2,3-dione