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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,5S)-5-[(1S)-1-amino-2-hydroxyethyl]-3-propan-2-yloxolan-2-one 1000146-73-5 C9H17NO3
    (3S,5S)-5-[(1S)-1-amino-2-hydroxyethyl]-3-propan-2-yloxolan-2-one
    —— tert-butyl 2-{(1R,4R,7S,8S)-7-(furan-2-yl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate 1312102-39-8 C17H19NO8
    tert-butyl 2-{(1R,4R,7S,8S)-7-(furan-2-yl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate
    —— tert-butyl 2-{(1R,4R,7S,8S)-8-nitro-3,6-dioxo-7-phenyl-2-oxabicyclo[2.2.2]octan-1-yl}acetate 1312102-15-0 C19H21NO7
    tert-butyl 2-{(1R,4R,7S,8S)-8-nitro-3,6-dioxo-7-phenyl-2-oxabicyclo[2.2.2]octan-1-yl}acetate
    —— tert-butyl 2-{(1R,4R,7S,8S)-7-(4-fluorophenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate 1312102-19-4 C19H20FNO7
    tert-butyl 2-{(1R,4R,7S,8S)-7-(4-fluorophenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate
    —— (4aR,7aS)-2-oxo-3,4,5,6,7,7a-hexahydrocyclopenta[b]pyran-4a-carbonyl azide 1026913-69-8 C9H11N3O3
    (4aR,7aS)-2-oxo-3,4,5,6,7,7a-hexahydrocyclopenta[b]pyran-4a-carbonyl azide
    —— (4aR,7aS)-2-oxo-3,4,5,6,7,7a-hexahydrocyclopenta[b]pyran-4a-carboxylic acid 880637-67-2 C9H12O4
    (4aR,7aS)-2-oxo-3,4,5,6,7,7a-hexahydrocyclopenta[b]pyran-4a-carboxylic acid
    —— 3,4-dihydroxy-1,7-dioxaspiro[4.4]nonan-8-one 197219-87-7 C7H10O5
    3,4-dihydroxy-1,7-dioxaspiro[4.4]nonan-8-one
    —— (5S*,6R*)-5-bromo-6-(4-methylphenyl)tetrahydro-2H-pyran-2-one —— C12H13BrO2
    (5S*,6R*)-5-bromo-6-(4-methylphenyl)tetrahydro-2H-pyran-2-one
    —— (Z)-α-cyclohexylmethylene-γ-valerolactone 132209-85-9 C12H18O2
    (Z)-α-cyclohexylmethylene-γ-valerolactone
    —— (E)-α-cyclohexylmethylene-γ-valerolactone 132209-84-8 C12H18O2
    (E)-α-cyclohexylmethylene-γ-valerolactone
    —— 4,4-dimethyl-cyclopentane-1,3-dicarboxylic acid-anhydride 118061-09-9 C9H12O3
    4,4-dimethyl-cyclopentane-1,3-dicarboxylic acid-anhydride
    —— 3-oxabicyclo[3.2.1]oct-6-en-2,4-dione 165105-94-2 C7H6O3
    3-oxabicyclo[3.2.1]oct-6-en-2,4-dione
    —— endo phenyl-5 oxa-4 exo tricyclo<5,2,1,02,6>decene-8 one-3 117436-85-8 C15H14O2
    endo phenyl-5 oxa-4 exo tricyclo<5,2,1,02,6>decene-8 one-3
    —— (Z)-α-(1-chloropentylidene)-β-cyclohexyl-β-lactone 627526-77-6 C14H21ClO2
    (Z)-α-(1-chloropentylidene)-β-cyclohexyl-β-lactone
    —— (5-methyl-2-oxo-tetrahydro-[3]furyl)-glyoxylic acid methyl ester 106164-18-5 C8H10O5
    (5-methyl-2-oxo-tetrahydro-[3]furyl)-glyoxylic acid methyl ester
    —— 4(S),5(S)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one 476468-28-7 C6H10O4
    4(S),5(S)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one
    —— trans-3,5-diphenyldihydrofuran-2(3H)-one —— C16H14O2
    trans-3,5-diphenyldihydrofuran-2(3H)-one
    —— (3-oxo-2-oxa-bicyclo[2.2.2]octan-4-yl)-acetic acid 70909-78-3 C9H12O4
    (3-oxo-2-oxa-bicyclo[2.2.2]octan-4-yl)-acetic acid
    —— (3S,3aR,6aS)-3-methyl-1-[(1S)-1-phenylethyl]-3,3a,6,6a-tetrahydrofuro[3,2-c][1,2]oxazol-5-one 78465-22-2 C14H17NO3
    (3S,3aR,6aS)-3-methyl-1-[(1S)-1-phenylethyl]-3,3a,6,6a-tetrahydrofuro[3,2-c][1,2]oxazol-5-one
    —— (2S,3S)-2-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolane-3-carboxylic acid 192824-01-4 C13H24O5Si
    (2S,3S)-2-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolane-3-carboxylic acid
    —— cis-3,5-diphenyldihydrofuran-2(3H)-one —— C16H14O2
    cis-3,5-diphenyldihydrofuran-2(3H)-one
    —— tert-butyl N-[(2S,3S)-2-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolan-3-yl]carbamate 192824-03-6 C17H33NO5Si
    tert-butyl N-[(2S,3S)-2-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolan-3-yl]carbamate
    —— (3RS,5RS)-3,5-diphenyl-3H-4,5-dihydro-2-furanone —— C16H14O2
    (3RS,5RS)-3,5-diphenyl-3H-4,5-dihydro-2-furanone
    —— 3-Hexyl-4-septyloxetan-2-one 872631-18-0 C16H30O2
    3-Hexyl-4-septyloxetan-2-one
    —— 3,3-Dichloro-4-chloromethyltetrahydrofuran-2-one 87223-92-5 C5H5Cl3O2
    3,3-Dichloro-4-chloromethyltetrahydrofuran-2-one
    —— (3R)-(-)-3-Hydroxymethyl-2-(5-methylhexanoyl)-4-butanolide 122922-47-8 C12H20O4
    (3R)-(-)-3-Hydroxymethyl-2-(5-methylhexanoyl)-4-butanolide
    —— (SR)-4-(hydroxymethyl)-3-methylenedihydrofuran-2(3H)-one 1207955-18-7 C6H8O3
    (SR)-4-(hydroxymethyl)-3-methylenedihydrofuran-2(3H)-one
    —— 4,5,5,4',5',5'-hexamethyl-tetrahydro-[3,3']bifuryl-2,2'-dione 35096-34-5 C14H22O4
    4,5,5,4',5',5'-hexamethyl-tetrahydro-[3,3']bifuryl-2,2'-dione
    —— (4R,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide 222547-85-5 C23H32O2Se
    (4R,5R)-5-((1E,3E)-1,3,6,6-tetramethyl-1,3-hexadienyl)-4-methyl-3-(phenylseleno)methyl-5-pentenolide
    —— (1<i>R</i>)-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-ene-8<i>anti</i>-carboxylic acid 54382-55-7 C10H12O4
    (1<i>R</i>)-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-ene-8<i>anti</i>-carboxylic acid
    —— 2,3-dideoxy-2-methyl-D-glucono-1,4-lactone 1067648-41-2 C7H12O4
    2,3-dideoxy-2-methyl-D-glucono-1,4-lactone
    —— (3R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3-methoxyoxolan-2-one 1079398-44-9 C7H12O5
    (3R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3-methoxyoxolan-2-one
    —— α-hexadecyl-β-heptadecylidene-3-propanolide 10126-68-8 C36H68O2
    α-hexadecyl-β-heptadecylidene-3-propanolide
    —— opt. inakt. 4-Ethoxy-4-hydroxy-2-methyl-buttersaeure-lacton 3494-91-5 C7H12O3
    opt. inakt. 4-Ethoxy-4-hydroxy-2-methyl-buttersaeure-lacton
    —— 5-methyl-3-(2,4,5-tribromo-3-thienyl)tetrahydrofuran-2-one 425381-63-1 C9H7Br3O2S
    5-methyl-3-(2,4,5-tribromo-3-thienyl)tetrahydrofuran-2-one
    —— 5-methyl-3-(3-thienyl)tetrahydrofuran-2-one 425381-55-1 C9H10O2S
    5-methyl-3-(3-thienyl)tetrahydrofuran-2-one
    —— (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-3-O-(chlorocarbonyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid δ-lactone 221008-00-0 C19H29ClO6
    (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-3-O-(chlorocarbonyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid δ-lactone
    —— (3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one 1040882-61-8 C6H9FO4
    (3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
    —— (3aS,6R,7R,7aS)-6-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-hydroxy-3a,7-dimethyl-3,6,7,7a-tetrahydro-2H-furo[3,2-c]pyran-4-one 221008-02-2 C15H24O6
    (3aS,6R,7R,7aS)-6-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-hydroxy-3a,7-dimethyl-3,6,7,7a-tetrahydro-2H-furo[3,2-c]pyran-4-one
    —— (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid δ-lactone 221007-86-9 C18H30O5
    (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid δ-lactone
    —— (6Z,9S)-6-ethylidene-9-hydroxymethyl-9-nonanolide 138253-42-6 C12H20O3
    (6Z,9S)-6-ethylidene-9-hydroxymethyl-9-nonanolide
    —— <3S-<3α,3aα,6β(R<sup>*</sup>),7α,7aα>>-<6-<(2,2-dimethyl-1,3-dioxolan-4-yl)methyl>hexahydro-3a,7-dimethyl-2-hydroxy-4-oxo-4H-furo<3,2-c>pyran-3-yl>carbamic acid ethyl ester 221008-03-3 C18H29NO8
    <3S-<3α,3aα,6β(R<sup>*</sup>),7α,7aα>>-<6-<(2,2-dimethyl-1,3-dioxolan-4-yl)methyl>hexahydro-3a,7-dimethyl-2-hydroxy-4-oxo-4H-furo<3,2-c>pyran-3-yl>carbamic acid ethyl ester
    —— 6(Z)-6-ethylidene-9-methyl-9-nonanolide 138253-44-8 C12H20O2
    6(Z)-6-ethylidene-9-methyl-9-nonanolide
    —— <3aS-<3aα,6β(R<sup>*</sup>),7α,7aα>>-6-<(2,2-dimethyl-1,3-dioxolan-4-yl)methyl>-3a,6,7,7a-tetrahydro-3a,7-dimethyl-4H-furo<3,2-c>pyran-4-one 221007-87-0 C15H22O5
    <3aS-<3aα,6β(R<sup>*</sup>),7α,7aα>>-6-<(2,2-dimethyl-1,3-dioxolan-4-yl)methyl>-3a,6,7,7a-tetrahydro-3a,7-dimethyl-4H-furo<3,2-c>pyran-4-one
    —— (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-3-O-(azidocarbonyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid δ-lactone 221008-07-7 C19H29N3O6
    (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-3-O-(azidocarbonyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid δ-lactone
    —— (3S,4S)-3-(dec-9-ynyl)-4-(4-(3-dimethylaminopropylsylfonyl)butyl)oxetan-2-one 1351669-41-4 C22H39NO4S
    (3S,4S)-3-(dec-9-ynyl)-4-(4-(3-dimethylaminopropylsylfonyl)butyl)oxetan-2-one
    —— tetrahydro-5-(triphenylsilyl)-2H-pyran-2-one 918422-63-6 C23H22O2Si
    tetrahydro-5-(triphenylsilyl)-2H-pyran-2-one
    —— 2,2-Dimethyl-3-methylen-4-butanolid 73461-19-5 C7H10O2
    2,2-Dimethyl-3-methylen-4-butanolid
    —— 5-epi-compactin 84173-29-5 C23H34O5
    5-epi-compactin
    —— (3S,4R,5R)-4-hydroxy-3,5-bis(hydroxymethyl)oxolan-2-one 106296-46-2 C6H10O5
    (3S,4R,5R)-4-hydroxy-3,5-bis(hydroxymethyl)oxolan-2-one