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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 内酯类

    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
    —— (3R,3aS,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tertbutyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one 420846-38-4 C27H35NO6Si
    (3R,3aS,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tertbutyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one
    —— teucvidin 51918-98-0 C19H20O5
    teucvidin
    —— isoteuflin 54168-74-0 C19H20O5
    isoteuflin
    —— 12-epi-Teucvin 89617-43-6 C19H20O5
    12-epi-Teucvin
    —— teuflin 72541-00-5 C19H20O5
    teuflin
    —— (4S,4aS)-4,7-dimethyl-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyran-1-one 114298-64-5 C10H14O2
    (4S,4aS)-4,7-dimethyl-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyran-1-one
    —— 5-<1-(phenylseleno)ethyl>tetrahydrofuran-2-one 112238-65-0 C12H14O2Se
    5-<1-(phenylseleno)ethyl>tetrahydrofuran-2-one
    —— 1-(Methoxymethyl)-5-(trimethylsilyl)tetracyclo<3.3.0.0<sup>2,8</sup>.0<sup>4,6</sup>>octan-2,8-dicarbonsaeureanhydrid 134055-21-3 C15H20O4Si
    1-(Methoxymethyl)-5-(trimethylsilyl)tetracyclo<3.3.0.0<sup>2,8</sup>.0<sup>4,6</sup>>octan-2,8-dicarbonsaeureanhydrid
    —— chaetomugilin E 1098081-40-3 C24H29ClO6
    chaetomugilin E
    —— 1,7-dioxaspiro<2,4>heptan-6-on 126091-78-9 C5H6O3
    1,7-dioxaspiro<2,4>heptan-6-on
    —— 6-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-2-one 163252-42-4 C7H12O3
    6-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-2-one
    —— 9-Methyl-6-oxaspiro<4.5>decan-7-one 77520-32-2 C10H16O2
    9-Methyl-6-oxaspiro<4.5>decan-7-one
    —— (1S,5R)-1-(3-bromophenyl)-3-oxabicyclo[3.1.0]hexan-2-one 1402883-78-6 C11H9BrO2
    (1S,5R)-1-(3-bromophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
    —— 1-(3-Bromophenyl)-3-oxabicyclo[3.1.0]hexan-2-one 1346146-39-1 C11H9BrO2
    1-(3-Bromophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
    —— (1R,4S,5R,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-6-methyl-2-oxabicyclo[2.2.1]heptan-3-one 594853-86-8 C19H38O4Si2
    (1R,4S,5R,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-6-methyl-2-oxabicyclo[2.2.1]heptan-3-one
    —— 2-[(3aR,4S,6aS)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]acetaldehyde 662112-07-4 C9H12O3
    2-[(3aR,4S,6aS)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]acetaldehyde
    —— (3aS,4S,6aS)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one 143572-26-3 C24H28O4Si
    (3aS,4S,6aS)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one
    —— (1S,5R)-6-carbomethoxymethyl-2-oxabicyclo[3.3.0]-oct-3-one 128820-26-8 C10H14O4
    (1S,5R)-6-carbomethoxymethyl-2-oxabicyclo[3.3.0]-oct-3-one
    —— (1S,5R)-6-(2'-iodoethyl)-2-oxabicyclo[3.3.0]-oct-3-one 194141-90-7 C9H13IO2
    (1S,5R)-6-(2'-iodoethyl)-2-oxabicyclo[3.3.0]-oct-3-one
    —— 3-[(3aR,4S,6aS)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]propanoic acid 10458-28-3 C10H14O4
    3-[(3aR,4S,6aS)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]propanoic acid
    —— (5S)-5-[(1R,2R)-1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxypropyl]oxolan-2-one 384341-88-2 C13H26O5Si
    (5S)-5-[(1R,2R)-1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxypropyl]oxolan-2-one
    —— (1S,4R,5S,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 384341-72-4 C18H36O4Si2
    (1S,4R,5S,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one
    —— (1′R,5R)-5-{1′-[(tert-butyldimethylsilyl)oxy]-2′-[(tert-butyldimethylsilyl)oxy]ethyl}-3H,5H-furan-2-one 266345-29-3 C18H38O4Si2
    (1′R,5R)-5-{1′-[(tert-butyldimethylsilyl)oxy]-2′-[(tert-butyldimethylsilyl)oxy]ethyl}-3H,5H-furan-2-one
    —— (-)-(3R,5S)-3-hydroxy-5-decanolide 135415-55-3 C10H18O3
    (-)-(3R,5S)-3-hydroxy-5-decanolide
    —— (-)-(3R,5S,8E)-3-hydroxy-5-dec-8-enolide 135352-04-4 C10H16O3
    (-)-(3R,5S,8E)-3-hydroxy-5-dec-8-enolide
    —— (2S,2'R,3S)-2,3-bis-(tert-butyldimethylsilanyloxy)-3-(5-oxo-tetrahydrofuran-2-yl)propionaldehyde 305384-16-1 C19H38O5Si2
    (2S,2'R,3S)-2,3-bis-(tert-butyldimethylsilanyloxy)-3-(5-oxo-tetrahydrofuran-2-yl)propionaldehyde
    —— (1R,4S,5S,6S)-6-(tert-butyldimethylsilanyloxy)-5-(triethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 305384-22-9 C18H36O4Si2
    (1R,4S,5S,6S)-6-(tert-butyldimethylsilanyloxy)-5-(triethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one
    —— (+)-(3R,5R,8E)-3-hydroxy-5-dec-8-enolide 135352-03-3 C10H16O3
    (+)-(3R,5R,8E)-3-hydroxy-5-dec-8-enolide
    —— (+)-(3S,5R,8E)-3-hydroxy-5-dec-8-enolide 135352-06-6 C10H16O3
    (+)-(3S,5R,8E)-3-hydroxy-5-dec-8-enolide
    —— (1S,2S,3R,4S,5R)-3,4-bis-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)-6-oxabicyclo[3.2.1]octan-7-one 305384-18-3 C25H52O5Si3
    (1S,2S,3R,4S,5R)-3,4-bis-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)-6-oxabicyclo[3.2.1]octan-7-one
    —— (1'S,2'R,5R)-5-[1,2,3-tris-(tert-butyldimethylsilanyloxy)propyl]dihydrofuran-2-one 305384-14-9 C25H54O5Si3
    (1'S,2'R,5R)-5-[1,2,3-tris-(tert-butyldimethylsilanyloxy)propyl]dihydrofuran-2-one
    —— (-)-(3S,5S)-3-hydroxy-5-decanolide 135415-56-4 C10H18O3
    (-)-(3S,5S)-3-hydroxy-5-decanolide
    —— (5S)-5-[(2R,5R)-5-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]oxolan-2-yl]oxolan-2-one 266345-34-0 C22H44O5Si2
    (5S)-5-[(2R,5R)-5-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]oxolan-2-yl]oxolan-2-one
    —— (1'S,2'R,5R)-5-[1,2-bis-(tert-butyldimethylsilanyloxy)-3-hydroxypropyl]dihydrofuran-2-one 305384-15-0 C19H40O5Si2
    (1'S,2'R,5R)-5-[1,2-bis-(tert-butyldimethylsilanyloxy)-3-hydroxypropyl]dihydrofuran-2-one
    —— (1R,4S,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 384341-66-6 C18H36O4Si2
    (1R,4S,5S,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one
    —— (1R,4S,5R,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 384341-68-8 C18H36O4Si2
    (1R,4S,5R,6S)-5,6-bis(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one
    —— (2R,2'R)-2-(tert-butyldimethylsilanyloxy)-2-(5-oxotetrahydrofuran-2-yl)propionaldehyde 594853-84-6 C13H24O4Si
    (2R,2'R)-2-(tert-butyldimethylsilanyloxy)-2-(5-oxotetrahydrofuran-2-yl)propionaldehyde
    —— (2S,2'S)-2-(tert-butyldimethylsilanyloxy)-(5-oxo-tetrahydrofuran-2-yl)acetaldehyde 384341-71-3 C12H22O4Si
    (2S,2'S)-2-(tert-butyldimethylsilanyloxy)-(5-oxo-tetrahydrofuran-2-yl)acetaldehyde
    —— (1'S,2'R,5R)-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]dihydrofuran-2-one 266345-89-5 C13H26O5Si
    (1'S,2'R,5R)-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]dihydrofuran-2-one
    —— (1S,4R,5R,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 384341-73-5 C18H36O4Si2
    (1S,4R,5R,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one
    —— (5R)-5-[(2R,5R)-5-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]oxolan-2-yl]oxolan-2-one 266345-33-9 C22H44O5Si2
    (5R)-5-[(2R,5R)-5-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]oxolan-2-yl]oxolan-2-one
    —— D-Gluco-D-gulo-heptonsaeure-γ-lacton 89-67-8 C7H12O7
    D-Gluco-D-gulo-heptonsaeure-γ-lacton
    —— (4R,5R)-4-benzyl-5-(hydroxymethyl)dihydrofuran-2(3H)-one 1423026-31-6 C12H14O3
    (4R,5R)-4-benzyl-5-(hydroxymethyl)dihydrofuran-2(3H)-one
    —— 3,4-dihydro-2H-[2,2]-bifuranyl-5-one 887402-55-3 C8H8O3
    3,4-dihydro-2H-[2,2]-bifuranyl-5-one
    —— 2,3,3-trimethyl-4-(2',2'-dichlorovinyl)-4-butanolide 64501-95-7 C9H12Cl2O2
    2,3,3-trimethyl-4-(2',2'-dichlorovinyl)-4-butanolide
    —— (1S,4R,6S,7R)-8,10-dimethoxy-3,9-dioxo-2-oxatricyclo<4.4.0.1<sup>4.7</sup>>undecane 134923-74-3 C11H16O5
    (1S,4R,6S,7R)-8,10-dimethoxy-3,9-dioxo-2-oxatricyclo<4.4.0.1<sup>4.7</sup>>undecane
    —— (5S)-3-methylidene-5-(2-methylprop-1-enyl)oxolan-2-one 1449005-73-5 C9H12O2
    (5S)-3-methylidene-5-(2-methylprop-1-enyl)oxolan-2-one
    —— α-carboxy-α-methyl-γ-valerolactone 74002-73-6 C7H10O4
    α-carboxy-α-methyl-γ-valerolactone
    —— (5R,6R)-3-methylene-6-phenyl-5-vinyltetrahydro-2H-pyran-2-one 1346159-06-5 C14H14O2
    (5R,6R)-3-methylene-6-phenyl-5-vinyltetrahydro-2H-pyran-2-one
    —— (R)-6-phenyl-5-hexyn-4-olide 140844-84-4 C12H10O2
    (R)-6-phenyl-5-hexyn-4-olide