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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
—— 3-bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one —— C7H7BrO2
3-bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
—— (3R,5S)-5-(methoxymethyl)-3-(octadeca-17-en-9, 11-diyn-1-yl)dihydrofuran-2(3H)-one —— C24H36O3
(3R,5S)-5-(methoxymethyl)-3-(octadeca-17-en-9, 11-diyn-1-yl)dihydrofuran-2(3H)-one
—— 5,5-dibenzyl-2-methoxycarbonyl-5-pentanolide —— C21H22O4
5,5-dibenzyl-2-methoxycarbonyl-5-pentanolide
—— ethyl α,α,-3-trichloro-3,4,5,6-tetrahydro-4,4-dimethyl-6-oxo-2H-pyran-2-acetate —— C11H15Cl3O4
ethyl α,α,-3-trichloro-3,4,5,6-tetrahydro-4,4-dimethyl-6-oxo-2H-pyran-2-acetate
—— 4-nonyloxetan-2-one —— C12H22O2
4-nonyloxetan-2-one
—— 4-nonyl-3-methyloxetan-2-one —— C13H24O2
4-nonyl-3-methyloxetan-2-one
—— 5-(hydroxymethyl)-5-phenyldihydrofuran-2(3H)-one —— C11H12O3
5-(hydroxymethyl)-5-phenyldihydrofuran-2(3H)-one
—— (R)-5-oxo-2-phenyltetrahydrofuran-2-carboxylic acid —— C11H10O4
(R)-5-oxo-2-phenyltetrahydrofuran-2-carboxylic acid
—— furan-2,3,4-trione-3-oxime —— C4H3NO4
furan-2,3,4-trione-3-oxime
—— trans-9-oxa-bicyclo[6.2.0]decan-10-one —— C9H14O2
trans-9-oxa-bicyclo[6.2.0]decan-10-one
—— (4S,6R)-4,6-dimethyl-2-oxepanone —— C8H14O2
(4S,6R)-4,6-dimethyl-2-oxepanone
—— 4-hexyl-4-hydroxy-5,5-dimethyl-4,5-dihydrofuran-2(3H)-one —— C12H22O3
4-hexyl-4-hydroxy-5,5-dimethyl-4,5-dihydrofuran-2(3H)-one
—— (E)-5-methyl-3-(4-methylpent-1-en-1-yl)dihydrofuran-2(3H)-one —— C11H18O2
(E)-5-methyl-3-(4-methylpent-1-en-1-yl)dihydrofuran-2(3H)-one
—— (E)-5-(chloromethyl)-3-(4-methylpent-1-en-1-yl)dihydrofuran-2(3H)-one —— C11H17ClO2
(E)-5-(chloromethyl)-3-(4-methylpent-1-en-1-yl)dihydrofuran-2(3H)-one
—— 4,6,6-trimethyl-oxepan-2-one —— C9H16O2
4,6,6-trimethyl-oxepan-2-one
—— 3-{2-[(trimethylsilyl)oxy]propyl}dihydro-2(3H)-furanone —— C10H20O3Si
3-{2-[(trimethylsilyl)oxy]propyl}dihydro-2(3H)-furanone
—— 4-isopropyl-4-methyloxetan-2-one —— C7H12O2
4-isopropyl-4-methyloxetan-2-one
—— 5-(2-furyl)-3,3-dimethyltetrahydro-2-furanone —— C10H12O3
5-(2-furyl)-3,3-dimethyltetrahydro-2-furanone
—— 4-(2-methylphenyl)dihydropyran-2,6-dione —— C12H12O3
4-(2-methylphenyl)dihydropyran-2,6-dione
—— 4β-n-butyl-6α-tert-butyl-tetrahydro-4α,6β-dimethyl-2H-pyran-2-one —— C15H28O2
4β-n-butyl-6α-tert-butyl-tetrahydro-4α,6β-dimethyl-2H-pyran-2-one
—— (E)-3-(but-3-yn-2-ylidene)dihydrofuran-2(3H)-one —— C8H8O2
(E)-3-(but-3-yn-2-ylidene)dihydrofuran-2(3H)-one
—— (1SR,3RS,6SR,7RS)-8,9-dicyano-6-methyl-4-oxatricyclo-[4.3.1.0<sup>3,7</sup>]dec-8-en-5-one —— C12H10N2O2
(1SR,3RS,6SR,7RS)-8,9-dicyano-6-methyl-4-oxatricyclo-[4.3.1.0<sup>3,7</sup>]dec-8-en-5-one
—— (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl (E)-3-triphenylstannylpropenoate —— C27H26O4Sn
(R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl (E)-3-triphenylstannylpropenoate
—— 2-Methyl-5-cyclohexylhex-4-en-6-olide —— C13H20O2
2-Methyl-5-cyclohexylhex-4-en-6-olide
—— (S)-5-methylhexanolide —— C7H12O2
(S)-5-methylhexanolide
—— 6-Ethyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-one —— C11H18O2
6-Ethyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-one
—— 6-Ethyl-7-methylene-3-oxaspiro<5.5>undecan-2-one —— C13H20O2
6-Ethyl-7-methylene-3-oxaspiro<5.5>undecan-2-one
—— (E)-5-ethyltetrahydro-[2,3']-bifuranyliden-2'-one —— C10H14O3
(E)-5-ethyltetrahydro-[2,3']-bifuranyliden-2'-one
—— (S)-5-methyl-2-oxepanone —— C7H12O2
(S)-5-methyl-2-oxepanone
—— (S)-5-(tert-butyl)oxepan-2-one —— C10H18O2
(S)-5-(tert-butyl)oxepan-2-one
—— 5,5-bis-methylamino-dihydro-furan-2-one —— C6H12N2O2
5,5-bis-methylamino-dihydro-furan-2-one
—— 5,5-diamino-dihydro-furan-2-one —— C4H8N2O2
5,5-diamino-dihydro-furan-2-one
—— (-)-(4R,7R)-7-methyl-4-isopropenyl-2-oxooxepanone —— C10H16O2
(-)-(4R,7R)-7-methyl-4-isopropenyl-2-oxooxepanone
—— (1S,4S,5R)-6,6-diethoxy-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one —— C16H26O6
(1S,4S,5R)-6,6-diethoxy-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
—— 5-isopropyl-4-methyl-dihydrofuran-2(3H)-one —— C8H14O2
5-isopropyl-4-methyl-dihydrofuran-2(3H)-one
—— 6,6-diethoxy-5-(2-methoxyethoxymethoxy)-3-oxabicyclo[3.2.0]heptan-5-one —— C14H24O7
6,6-diethoxy-5-(2-methoxyethoxymethoxy)-3-oxabicyclo[3.2.0]heptan-5-one
—— (+)-(R)-5-ethyloxepan-2-one —— C8H14O2
(+)-(R)-5-ethyloxepan-2-one
—— 5-ethyloxepan-2-one —— C8H14O2
5-ethyloxepan-2-one
—— 6-isopropyl-1-oxa-5-aza-cycloundecan-11-one —— C12H23NO2
6-isopropyl-1-oxa-5-aza-cycloundecan-11-one
—— t-butyl-caprolactone —— C10H18O2
t-butyl-caprolactone
—— (R)-ε-decalactone —— C10H18O2
(R)-ε-decalactone
—— (S)-ε-decalactone —— C10H18O2
(S)-ε-decalactone
—— (R)-(-)-2-<(Dimethylphenylsilyl)oxy>-2-methyl-γ-butyrolactone —— C13H18O3Si
(R)-(-)-2-<(Dimethylphenylsilyl)oxy>-2-methyl-γ-butyrolactone
—— (S)-(+)-2-<(Dimethylphenylsilyl)oxy>-2-methyl-γ-butyrolactone —— C13H18O3Si
(S)-(+)-2-<(Dimethylphenylsilyl)oxy>-2-methyl-γ-butyrolactone
—— (4S)-4-(prop-2-yl)oxacycloheptan-2-one —— C9H16O2
(4S)-4-(prop-2-yl)oxacycloheptan-2-one
—— 5-hexyl-4-methyldihydrofuran-2(3H)-one —— C11H20O2
5-hexyl-4-methyldihydrofuran-2(3H)-one
—— 3-methyldihydro-3,4-dibromo-2(3H)-furanone —— C5H6Br2O2
3-methyldihydro-3,4-dibromo-2(3H)-furanone
—— (E)-3-methyl-3-(2-methylhex-2-enyl)dihydrofuran-2(3H)-one —— C12H20O2
(E)-3-methyl-3-(2-methylhex-2-enyl)dihydrofuran-2(3H)-one
—— R-(-)-α-benzyl-α-methyl-γ-butyrolactone —— C12H14O2
R-(-)-α-benzyl-α-methyl-γ-butyrolactone
—— α-methyl-α-trifluoromethyl-γ-butyrolactone —— C6H7F3O2
α-methyl-α-trifluoromethyl-γ-butyrolactone