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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
    —— (3S,4S,5S)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone 110612-43-6 C9H16O3
    (3S,4S,5S)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
    —— (3R,4R,5R)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone 56297-90-6 C9H16O3
    (3R,4R,5R)-3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
    —— 2,3-dimethyl-glutaric acid-anhydride 138500-84-2 C7H10O3
    2,3-dimethyl-glutaric acid-anhydride
    —— 3',3',9,9-Tetrachlorospiro(bicylo[5.2.0]nona-2,4-diene-8,2'-oxetan)-4'-one 393091-06-0 C11H8Cl4O2
    3',3',9,9-Tetrachlorospiro(bicylo[5.2.0]nona-2,4-diene-8,2'-oxetan)-4'-one
    —— dihydro-3-<<(trimethylsilyl)oxy>methylene>-2(3H)-furanone 76881-13-5 C8H14O3Si
    dihydro-3-<<(trimethylsilyl)oxy>methylene>-2(3H)-furanone
    —— 5-[4-(3-carboxyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone 1082071-03-1 C12H17NO5
    5-[4-(3-carboxyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone
    —— 5-[4-(3-hexyloxycarbonyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone 1082071-07-5 C18H29NO5
    5-[4-(3-hexyloxycarbonyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone
    —— O,O-diethyl S-(5-methyl-2-oxotetrahydrofuran-3-yl) thiophosphate 3659-07-2 C9H17O5PS
    O,O-diethyl S-(5-methyl-2-oxotetrahydrofuran-3-yl) thiophosphate
    —— O,O-diethyl S-(2-oxotetrahydropyran-3-yl) thiophosphate 885118-54-7 C9H17O5PS
    O,O-diethyl S-(2-oxotetrahydropyran-3-yl) thiophosphate
    —— (2R,5S,6S)-5-hydroxymethyl-4-oxa-exo-tricyclo<5.2.1.0<sup>2.6</sup>>dec-8-en-3-one 123750-61-8 C10H12O3
    (2R,5S,6S)-5-hydroxymethyl-4-oxa-exo-tricyclo<5.2.1.0<sup>2.6</sup>>dec-8-en-3-one
    —— (1S,4S,5R)-4-hydroxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one 1311267-44-3 C7H8O3
    (1S,4S,5R)-4-hydroxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one
    —— (1R,4S,5S)-4-hydroxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one 1311267-43-2 C7H8O3
    (1R,4S,5S)-4-hydroxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one
    —— (1R,4S,5S)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one 169871-03-8 C12H18O4
    (1R,4S,5S)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (1S,4S,5R)-4-trifluoroacetyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one 173829-68-0 C13H17F3O4
    (1S,4S,5R)-4-trifluoroacetyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (1R,2R,5R,6S,11S)-5-(hydroxymethyl)-11-[(2-methylpropan-2-yl)oxy]-4,7-dioxa-8-azatricyclo[6.3.0.02,6]undecan-3-one 879559-11-2 C13H21NO5
    (1R,2R,5R,6S,11S)-5-(hydroxymethyl)-11-[(2-methylpropan-2-yl)oxy]-4,7-dioxa-8-azatricyclo[6.3.0.02,6]undecan-3-one
    —— (1R,4S,5S)-4-trifluoroacetyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one 173829-69-1 C13H17F3O4
    (1R,4S,5S)-4-trifluoroacetyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (1R,4S,5S)-4-tert-butyldimethylsilyloxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one 1311267-86-3 C13H22O3Si
    (1R,4S,5S)-4-tert-butyldimethylsilyloxymethyl-3-oxabicyclo[3.2.0]hept-6-en-2-one
    —— (S)-(+)-γ-iodometil-γ-butirrolattone 58879-36-0 C5H7IO2
    (S)-(+)-γ-iodometil-γ-butirrolattone
    —— (1S,4S,5R)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one 169871-04-9 C12H18O4
    (1S,4S,5R)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (-)-(1S,4S,5R)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one 169870-98-8 C16H26O4
    (-)-(1S,4S,5R)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (1R,4S,5S)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one 169870-99-9 C16H26O4
    (1R,4S,5S)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (1R,4S,5S)-4-(iodomethyl)-3-oxabicyclo[3.1.0]hexan-2-one 159950-60-4 C6H7IO2
    (1R,4S,5S)-4-(iodomethyl)-3-oxabicyclo[3.1.0]hexan-2-one
    —— (1R,4S,5S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-oxabicyclo[3.1.0]hexan-2-one 159950-58-0 C22H26O3Si
    (1R,4S,5S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-oxabicyclo[3.1.0]hexan-2-one
    —— (1S,2R,5R,6S,10S,11S)-5-(hydroxymethyl)-10,11-bis[(2-methylpropan-2-yl)oxy]-4,7-dioxa-8-azatricyclo[6.3.0.02,6]undecan-3-one 879559-13-4 C17H29NO6
    (1S,2R,5R,6S,10S,11S)-5-(hydroxymethyl)-10,11-bis[(2-methylpropan-2-yl)oxy]-4,7-dioxa-8-azatricyclo[6.3.0.02,6]undecan-3-one
    —— (2R,5S,6S)-5-hydroxymethyl-4-oxa-endo-tricyclo<5.2.1.0<sup>2.6</sup>>dec-8-en-3-one 117063-99-7 C10H12O3
    (2R,5S,6S)-5-hydroxymethyl-4-oxa-endo-tricyclo<5.2.1.0<sup>2.6</sup>>dec-8-en-3-one
    —— (Z)-5-(oct-2-en-1-yl)dihydrofuran-2(3H)-one. 63357-98-2 C12H20O2
    (Z)-5-(oct-2-en-1-yl)dihydrofuran-2(3H)-one.
    —— (1R,4S,5S)-4-(tert-butyldimethylsilyloxymethyl)-3-oxabicyclo[3.2.0]heptan-2-one 877382-20-2 C13H24O3Si
    (1R,4S,5S)-4-(tert-butyldimethylsilyloxymethyl)-3-oxabicyclo[3.2.0]heptan-2-one
    —— (4R,5S)-4,5-bis(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-one 140156-23-6 C18H38O4Si2
    (4R,5S)-4,5-bis(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-one
    —— (4S,5S)-5-(tert-butyldimethylsiloxymethyl)-4-(fluoromethyl)tetrahydrofuran-2-one 164848-23-1 C12H23FO3Si
    (4S,5S)-5-(tert-butyldimethylsiloxymethyl)-4-(fluoromethyl)tetrahydrofuran-2-one
    —— (1R,4S,5S)-(-)-4-tert-butyldimethylsilylmethyl-5-methyl-3-oxabicyclo<3.2.0>heptan-2-one 151982-24-0 C14H26O3Si
    (1R,4S,5S)-(-)-4-tert-butyldimethylsilylmethyl-5-methyl-3-oxabicyclo<3.2.0>heptan-2-one
    —— (5R)-4-hydroxymethyltetrahydrofuran-2-one 34371-14-7 C5H8O4
    (5R)-4-hydroxymethyltetrahydrofuran-2-one
    —— (1S,4S,5R)-4-tert-butyldimethysilyloxymethyl-5-methyl-3-oxabicyclo[3.2.0]heptan-2-one 1374337-49-1 C14H26O3Si
    (1S,4S,5R)-4-tert-butyldimethysilyloxymethyl-5-methyl-3-oxabicyclo[3.2.0]heptan-2-one
    —— 4(R)-azido-5(S)-<(tert-butyldiphenylsilyl)oxymethyl>-3,4-dihydro-5H-furan-2-one 128461-35-8 C21H25N3O3Si
    4(R)-azido-5(S)-<(tert-butyldiphenylsilyl)oxymethyl>-3,4-dihydro-5H-furan-2-one
    —— (4R,5S)-4-benzyl-5-(hydroxymethyl)oxolan-2-one 189758-63-2 C12H14O3
    (4R,5S)-4-benzyl-5-(hydroxymethyl)oxolan-2-one
    —— 6-propylthiomethyl-3,4,5,6-tetrahydro-2-pyrone 108078-69-9 C9H16O2S
    6-propylthiomethyl-3,4,5,6-tetrahydro-2-pyrone
    —— 5-propylthiomethyl-4,5-dihydrofuran-2(3H)-one 108078-66-6 C8H14O2S
    5-propylthiomethyl-4,5-dihydrofuran-2(3H)-one
    —— 4-hydroxy-2,4-diphenyl-acetoacetic acid-lactone 22884-83-9 C16H12O3
    4-hydroxy-2,4-diphenyl-acetoacetic acid-lactone
    —— 4-Tert-butyl-4-methyloxolan-2-one 1312756-45-8 C9H16O2
    4-Tert-butyl-4-methyloxolan-2-one
    —— (4S)-methyl-2-(methylthio)-γ-butyrolactone 165880-30-8 C6H10O2S
    (4S)-methyl-2-(methylthio)-γ-butyrolactone
    —— 4α-hydroxy-5α,6β,7α,11β-H-guaian-1(10)-en-6,12-olide 35008-26-5 C15H22O3
    4α-hydroxy-5α,6β,7α,11β-H-guaian-1(10)-en-6,12-olide
    —— (3R,4R,5S,6S)-3,4,5,6-tetrahydro-4-hydroxy-3,5,6-trimethyl-2H-pyran-2-one 342901-02-4 C8H14O3
    (3R,4R,5S,6S)-3,4,5,6-tetrahydro-4-hydroxy-3,5,6-trimethyl-2H-pyran-2-one
    —— (4R,5R,6R)-6-[(2S)-butan-2-yl]-4-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-5-methyloxan-2-one 175695-19-9 C20H37NO3
    (4R,5R,6R)-6-[(2S)-butan-2-yl]-4-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-5-methyloxan-2-one
    —— 4,6-dimethyl-tetrahydro-pyran-2-one 3720-20-5 C7H12O2
    4,6-dimethyl-tetrahydro-pyran-2-one
    —— hexahydro-cyclopenta[c]furan-1-one —— C7H10O2
    hexahydro-cyclopenta[c]furan-1-one
    —— (6R)-6-((4R,5R)-5-((S)-1-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydro-2H-pyran-2-one 540727-84-2 C15H26O5
    (6R)-6-((4R,5R)-5-((S)-1-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydro-2H-pyran-2-one
    —— (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide 864182-70-7 C21H32O3SeSi
    (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide
    —— 6-(4-fluorophenyl)dihydro-2H-pyran-2,4(3H)-dione 862100-38-7 C11H9FO3
    6-(4-fluorophenyl)dihydro-2H-pyran-2,4(3H)-dione
    —— 3-methyl-5-[(1Z)-3-methylbuta-1,3-dienyl]oxolan-2-one 74133-35-0 C10H14O2
    3-methyl-5-[(1Z)-3-methylbuta-1,3-dienyl]oxolan-2-one
    —— (4S)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide 864182-73-0 C15H28O3Si
    (4S)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide
    —— helicascolide B 121325-38-0 C12H20O3
    helicascolide B