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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
—— (2R,2'S)-tetrahydro-[2,2']-bifuranyl-5,5'-dione 54933-62-9 C8H10O4
(2R,2'S)-tetrahydro-[2,2']-bifuranyl-5,5'-dione
—— (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 32384-42-2 C10H14O5
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone
—— (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one 124032-36-6 C20H35NO4
(3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one
—— 3,3,8-Trimethyl-2,7-dioxaspiro[4.4]nonane-1,6-dione 90237-09-5 C10H14O4
3,3,8-Trimethyl-2,7-dioxaspiro[4.4]nonane-1,6-dione
—— acide (methyl-2 propyl)-2 γ-valerolactone-2 carboxylique 90237-08-4 C10H16O4
acide (methyl-2 propyl)-2 γ-valerolactone-2 carboxylique
—— (methyl-2 propyl)-2 γ-valerolactone 72845-84-2 C9H16O2
(methyl-2 propyl)-2 γ-valerolactone
—— cineolic anhydride 4703-74-6 C10H14O4
cineolic anhydride
—— [(1S,4R,5S)-1-methyl-3-oxo-2-oxabicyclo[2.2.2]octan-5-yl] formate 107149-12-2 C9H12O4
[(1S,4R,5S)-1-methyl-3-oxo-2-oxabicyclo[2.2.2]octan-5-yl] formate
—— 5(RS)-hydroxy-2(SR)-methyl-4-oxa-endo-tricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-3-one —— C10H12O3
5(RS)-hydroxy-2(SR)-methyl-4-oxa-endo-tricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-3-one
—— (4S)-4,6,6-trimethyl-3,4,5,6-tetrahydro-2H-pyran-2-one 134178-37-3 C8H14O2
(4S)-4,6,6-trimethyl-3,4,5,6-tetrahydro-2H-pyran-2-one
—— 3-oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid tert-butyl ester 862174-61-6 C11H16O4
3-oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid tert-butyl ester
—— (R<sup>*</sup>,S<sup>*</sup>)-3,7-dimethyl-6-octanolide —— C10H18O2
(R<sup>*</sup>,S<sup>*</sup>)-3,7-dimethyl-6-octanolide
—— (1R,4R,5S)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid 1445593-36-1 C7H8O4
(1R,4R,5S)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid
—— (1S,4R,5S)-tert-butyl 3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylate 1445590-36-2 C11H16O4
(1S,4R,5S)-tert-butyl 3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylate
—— 3α,7α-dimethoxy-13-oxa-C-homo-cholan-12-one 1351984-87-6 C27H44O6
3α,7α-dimethoxy-13-oxa-C-homo-cholan-12-one
—— 4-bromomethyl-3,3-dimethyl-oxetan-2-one 33282-40-5 C6H9BrO2
4-bromomethyl-3,3-dimethyl-oxetan-2-one
—— 3-(2-Diethylaminoethyl)-4,5-dihydro-2(3H)-furanon 88735-22-2 C10H19NO2
3-(2-Diethylaminoethyl)-4,5-dihydro-2(3H)-furanon
—— 2-acetyl-4,4-dimethylbutanolide 7391-53-9 C8H12O3
2-acetyl-4,4-dimethylbutanolide
—— 3-(2-Diethylaminoethyl)-5,5-dimethyl-4,5-dihydro-2(3H)-furanon 88735-26-6 C12H23NO2
3-(2-Diethylaminoethyl)-5,5-dimethyl-4,5-dihydro-2(3H)-furanon
—— 1,5-dioxaspiro[2.4]heptan-4-one 98011-07-5 C5H6O3
1,5-dioxaspiro[2.4]heptan-4-one
—— (3R,4R)-trans-3-methyl-4-heptyloxetan-2-one 1057557-55-7 C11H20O2
(3R,4R)-trans-3-methyl-4-heptyloxetan-2-one
—— γ-heptyl-α-methylene-γ-butyrolactone 153925-74-7 C12H20O2
γ-heptyl-α-methylene-γ-butyrolactone
—— (4RS,5RS)-4-hydroxy-5-methyldihydrofuran-2(3H)-one 38996-22-4 C5H8O3
(4RS,5RS)-4-hydroxy-5-methyldihydrofuran-2(3H)-one
—— cis-(+/-)-4-heptyl-3-methyloxetan-2-one —— C11H20O2
cis-(+/-)-4-heptyl-3-methyloxetan-2-one
—— (S)-3-((R)-1-hydroxyoctyl)-3-(methylthio)dihydrofuran-2(3H)-one 1378531-87-3 C13H24O3S
(S)-3-((R)-1-hydroxyoctyl)-3-(methylthio)dihydrofuran-2(3H)-one
—— α-methylthio-γ-butyrolactone 40587-54-0 C5H8O2S
α-methylthio-γ-butyrolactone
—— (+/-)-4-heptyloxetan-2-one 39185-88-1 C10H18O2
(+/-)-4-heptyloxetan-2-one
—— tetra-O-(tert-butyldimethylsilyl)-D-glucono-1,4-lactone 318967-97-4 C30H66O6Si4
tetra-O-(tert-butyldimethylsilyl)-D-glucono-1,4-lactone
—— (1R,2S,3S,8R,9S,12S)-8-dodecyl-3,12-dimethyl-9-[(1E)-tetradec-1-en-1-yl]-4,11-dioxatricyclo[7.3.0.0,�?�]dodec-6-ene-5,10-dione (6) 1609642-88-7 C38H64O4
(1R,2S,3S,8R,9S,12S)-8-dodecyl-3,12-dimethyl-9-[(1E)-tetradec-1-en-1-yl]-4,11-dioxatricyclo[7.3.0.0,�?�]dodec-6-ene-5,10-dione (6)
—— 4-(7-Oxooxepan-4-yl)butyl methanesulfonate 144385-71-7 C11H20O5S
4-(7-Oxooxepan-4-yl)butyl methanesulfonate
—— 5-(4-Azidobutyl)oxepan-2-one 134164-08-2 C10H17N3O2
5-(4-Azidobutyl)oxepan-2-one
—— 4-(4-hydroxybutyl)-ε-caprolactone 134163-31-8 C10H18O3
4-(4-hydroxybutyl)-ε-caprolactone
—— 5-(4-Aminobutyl)oxepan-2-one 144385-72-8 C10H19NO2
5-(4-Aminobutyl)oxepan-2-one
—— (4R<sup>*</sup>, 5S<sup>*</sup>)-dihydro-5-methyl-4-phenyl-2(3H)-furanone 92927-63-4 C11H12O2
(4R<sup>*</sup>, 5S<sup>*</sup>)-dihydro-5-methyl-4-phenyl-2(3H)-furanone
—— (S)-(+)-Dihydro-5-<(E)-1,3-butadienyl>-2(3H)-furanone 151915-16-1 C8H10O2
(S)-(+)-Dihydro-5-<(E)-1,3-butadienyl>-2(3H)-furanone
—— 3,3-divinyldihydrofuran-2(3H)-one 1106930-26-0 C8H10O2
3,3-divinyldihydrofuran-2(3H)-one
—— tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid methyl ester 100813-26-1 C7H10O4
tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid methyl ester
—— 5-oxaspiro[2.4]hept-1-en-4-one 1106930-20-4 C6H6O2
5-oxaspiro[2.4]hept-1-en-4-one
—— cis-1,2-cyclobutane dicarboxylic anhydride 4462-96-8 C6H6O3
cis-1,2-cyclobutane dicarboxylic anhydride
—— [1-<sup>13</sup>C]dehydroascorbic acid 1159923-26-8 C6H6O6
[1-<sup>13</sup>C]dehydroascorbic acid
—— (4S,5S)-5-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-4-methyloxolan-2-one 412342-76-8 C24H32O3Si
(4S,5S)-5-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-4-methyloxolan-2-one
—— 4-(but-3-en-1-yl)-tetrahydro-2H-pyran-2-one 871720-27-3 C9H14O2
4-(but-3-en-1-yl)-tetrahydro-2H-pyran-2-one
—— Methyl 4-but-3-enyl-2-oxooxane-3-carboxylate 1184870-99-2 C11H16O4
Methyl 4-but-3-enyl-2-oxooxane-3-carboxylate
—— 4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-dihydro-2(3H)furanone 103576-61-0 C24H32O3Si
4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-dihydro-2(3H)furanone
—— [4R,6S]-6-(tert-butyldimethylsilanyloxymethyl)-4-methyl-tetrahydropyran-2-one 385809-06-3 C13H26O3Si
[4R,6S]-6-(tert-butyldimethylsilanyloxymethyl)-4-methyl-tetrahydropyran-2-one
—— dihydropyran-5,6-dione 154064-57-0 C5H6O3
dihydropyran-5,6-dione
—— (3S,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one —— C6H10O6
(3S,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
—— 3-(2-methylsulfanyl-ethyl)-dihydro-furan-2(3H)-one 1082301-45-8 C7H12O2S
3-(2-methylsulfanyl-ethyl)-dihydro-furan-2(3H)-one
—— (S)-γ-valerolactone 19041-15-7 C5H8O2
(S)-γ-valerolactone
—— 1S,6S-3,7-dioxa-bicyclo<4,3,0>non-4-en-8-one 87614-57-1 C7H8O3
1S,6S-3,7-dioxa-bicyclo<4,3,0>non-4-en-8-one