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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
    —— (2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide 137963-56-5 C24H32O4Si
    (2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide
    —— (4S,5R)-6-(tert-butyldiphenylsilyl)oxy-4-methoxy-5-hexanolide 137963-58-7 C23H30O4Si
    (4S,5R)-6-(tert-butyldiphenylsilyl)oxy-4-methoxy-5-hexanolide
    —— 2-chloro-4-phenyl-4-pentanolide 89630-69-3 C11H11ClO2
    2-chloro-4-phenyl-4-pentanolide
    —— 2-Chloro-5-oxatricyclo[8.4.0.03,7]tetradeca-1(14),2,10,12-tetraen-4-one 1207289-20-0 C13H11ClO2
    2-Chloro-5-oxatricyclo[8.4.0.03,7]tetradeca-1(14),2,10,12-tetraen-4-one
    —— (±)-5-(iodomethyl)-3,3-dimethyldihydrofuran-2(3H)-one 90897-98-6 C7H11IO2
    (±)-5-(iodomethyl)-3,3-dimethyldihydrofuran-2(3H)-one
    —— α-Hydroxy-γ-phenyl-methylbutyrolacton 51502-86-4 C11H12O3
    α-Hydroxy-γ-phenyl-methylbutyrolacton
    —— 2,3,4,5-tetra-O-methyl-D-glucono-1,6-lactone 541550-97-4 C10H18O6
    2,3,4,5-tetra-O-methyl-D-glucono-1,6-lactone
    —— Hexahydro-3,6-methanocyclopenta[c]pyran-1(3H)-one 30244-07-6 C9H12O2
    Hexahydro-3,6-methanocyclopenta[c]pyran-1(3H)-one
    —— 3-Methyl-3-[1-(2-methyloxiran-2-yl)propoxy]oxetan-2-one 73220-29-8 C10H16O4
    3-Methyl-3-[1-(2-methyloxiran-2-yl)propoxy]oxetan-2-one
    —— 2H-Cyclohepta[b]furan-2-one, octahydro-3-methyl-, (3R,3aS,8aS)-rel- 33366-33-5 C10H16O2
    2H-Cyclohepta[b]furan-2-one, octahydro-3-methyl-, (3R,3aS,8aS)-rel-
    —— (3aα,8aα)-3-methyleneoctahydro-2H-cyclohepta[b]furan-2-one 3725-04-0 C10H14O2
    (3aα,8aα)-3-methyleneoctahydro-2H-cyclohepta[b]furan-2-one
    —— 10,21-Dimethyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione 71425-98-4 C22H26O4
    10,21-Dimethyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
    —— 3-ethyl-hexahydro-cyclopenta[<i>b</i>]furan-2-one 67138-21-0 C9H14O2
    3-ethyl-hexahydro-cyclopenta[<i>b</i>]furan-2-one
    —— 5-ethoxy-4,5-dihydro-3-phenylfuran-2(3H)-one 99558-18-6 C12H14O3
    5-ethoxy-4,5-dihydro-3-phenylfuran-2(3H)-one
    —— β-Ethyl-γ,γ-dimethyl-γ-butyrolacton 28525-70-4 C8H14O2
    β-Ethyl-γ,γ-dimethyl-γ-butyrolacton
    —— (1R-(1α,5α,6α))-6-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 132435-60-0 C11H10O2
    (1R-(1α,5α,6α))-6-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
    —— (3S,4S,6S)-6-heptyl-3,4-dihydroxyoxan-2-one 1251927-19-1 C12H22O4
    (3S,4S,6S)-6-heptyl-3,4-dihydroxyoxan-2-one
    —— 3-oxa-bicyclo(5.3.1)undec-7(8)-en-2-one 74785-43-6 C10H14O2
    3-oxa-bicyclo(5.3.1)undec-7(8)-en-2-one
    —— 3,3-Bis(methylsulfanyl)oxan-2-one 90982-17-5 C7H12O2S2
    3,3-Bis(methylsulfanyl)oxan-2-one
    —— 3-(2'-acetoxyethyl)-dihydro-2(3H)-furanone 113844-96-5 C8H12O4
    3-(2'-acetoxyethyl)-dihydro-2(3H)-furanone
    —— α-(Ethylthio)-γ-butyrolactone 35998-33-5 C6H10O2S
    α-(Ethylthio)-γ-butyrolactone
    —— 3,3'-dithiobisdihydro-2-furanone 14091-96-4 C8H10O4S2
    3,3'-dithiobisdihydro-2-furanone
    —— sodium salt of α-mercapto-γ-butyrolactone 365532-26-9 C4H5O2S*Na
    sodium salt of α-mercapto-γ-butyrolactone
    —— (E)-α-propylidene-γ-butyrolactone 52216-90-7 C7H10O2
    (E)-α-propylidene-γ-butyrolactone
    —— α-cyclohexylidene-γ-butyrolactone 21681-63-0 C10H14O2
    α-cyclohexylidene-γ-butyrolactone
    —— (E)-α-heptylidene-γ-butyrolactone 66909-44-2 C11H18O2
    (E)-α-heptylidene-γ-butyrolactone
    —— α-(cyclohexylmethylene)-γ-butyrolactone 98441-94-2 C11H16O2
    α-(cyclohexylmethylene)-γ-butyrolactone
    —— (Z)-α-hexylidene-γ-butyrolactone 67404-96-0 C10H16O2
    (Z)-α-hexylidene-γ-butyrolactone
    —— (Z)-α-propylidene-γ-butyrolactone 52216-89-4 C7H10O2
    (Z)-α-propylidene-γ-butyrolactone
    —— Tetracyclo<3.3.0.0<sup>2,8</sup>.0<sup>4,6</sup>>octan-2,8-dicarbonsaeureanhydrid 134055-12-2 C10H8O3
    Tetracyclo<3.3.0.0<sup>2,8</sup>.0<sup>4,6</sup>>octan-2,8-dicarbonsaeureanhydrid
    —— 1-O-(2,2,2-trichloroethoxycarbonyl)-3,4-O-isopropyliden-1,5-γ-quinide 485402-20-8 C13H15Cl3O7
    1-O-(2,2,2-trichloroethoxycarbonyl)-3,4-O-isopropyliden-1,5-γ-quinide
    —— bicyclo<2,2,2>octane-2,6:3,5-dicarbolactone 6537-85-5 C10H10O4
    bicyclo<2,2,2>octane-2,6:3,5-dicarbolactone
    —— (R)-5-((S)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one 1217890-96-4 C7H8O3
    (R)-5-((S)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one
    —— 3,3-dimethyl-4-(4-pentyn-1-yl)oxetan-2-one 1046161-48-1 C10H14O2
    3,3-dimethyl-4-(4-pentyn-1-yl)oxetan-2-one
    —— (3S,5R)-3-hexyl-dihydro-5-phenylfuran-2(3H)-one 1092798-48-5 C16H22O2
    (3S,5R)-3-hexyl-dihydro-5-phenylfuran-2(3H)-one
    —— (R)-5-((R)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one 1217890-93-1 C7H8O3
    (R)-5-((R)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one
    —— (S)-5-((R)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one 1217891-02-5 C7H8O3
    (S)-5-((R)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one
    —— (S)-5-((S)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one 1217891-01-4 C7H8O3
    (S)-5-((S)-1-hydroxyprop-2-yn-1-yl)dihydrofuran-2(3H)-one
    —— 3,3-dimethyl-4-heptyloxetan-2-one 131436-07-2 C12H22O2
    3,3-dimethyl-4-heptyloxetan-2-one
    —— 3-{1-[(Trimethylsilyl)oxy]ethyl}oxolan-2-one 89588-46-5 C9H18O3Si
    3-{1-[(Trimethylsilyl)oxy]ethyl}oxolan-2-one
    —— 3-Methylspiro[2,3,4a,5,6,7,8,8a-octahydronaphthalene-4,3'-oxolane]-1,2'-dione 1314552-12-9 C14H20O3
    3-Methylspiro[2,3,4a,5,6,7,8,8a-octahydronaphthalene-4,3'-oxolane]-1,2'-dione
    —— 5(S)-octyl-2(3H)-dihydrofuranone 69830-92-8 C12H22O2
    5(S)-octyl-2(3H)-dihydrofuranone
    —— 136176-67-5 C12H10O2
    —— 3-methylene-1-oxaspiro[3.5]nonan-2-one 135638-62-9 C9H12O2
    3-methylene-1-oxaspiro[3.5]nonan-2-one
    —— 6-[(Z)-hept-1-enyl]oxan-2-one 18679-17-9 C12H20O2
    6-[(Z)-hept-1-enyl]oxan-2-one
    —— (+)-prelactone C 147659-06-1 C9H14O3
    (+)-prelactone C
    —— 2,3,4,5-Tetrahydro-5-oxo-2-phenyl-3-furancarbonsaeure-methylester 13389-99-6 C12H12O4
    2,3,4,5-Tetrahydro-5-oxo-2-phenyl-3-furancarbonsaeure-methylester
    —— 2,3,4,5-Tetrahydro-5-oxo-2-propyl-3-furancarbonsaeure-methylester 21984-96-3 C9H14O4
    2,3,4,5-Tetrahydro-5-oxo-2-propyl-3-furancarbonsaeure-methylester
    —— 3-methyl-2-methylene-5-pentanolide 114199-64-3 C7H10O2
    3-methyl-2-methylene-5-pentanolide
    —— 2-cyano-4-hexyl-γ-butyrolactone 53826-29-2 C11H17NO2
    2-cyano-4-hexyl-γ-butyrolactone