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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
—— (7S)-6-ethyl-7-methyl-3-phenyl-3a,6,7,7a-tetrahydropyrano[3,4-d][1,2]oxazol-4-one —— C15H17NO3
(7S)-6-ethyl-7-methyl-3-phenyl-3a,6,7,7a-tetrahydropyrano[3,4-d][1,2]oxazol-4-one
—— 4-Butan-2-yl-3,3-dimethyloxetan-2-one —— C9H16O2
4-Butan-2-yl-3,3-dimethyloxetan-2-one
—— 4-(1'-Butenyl)-4-methyl-γ-butyrolactone 14316-95-1 C9H14O2
4-(1'-Butenyl)-4-methyl-γ-butyrolactone
—— 5-(3-oxobutyl)dihydrofuran-2(3H)-one 89927-33-3 C8H12O3
5-(3-oxobutyl)dihydrofuran-2(3H)-one
—— 3-hydroxy-2-oxo-1-oxaspiro[4.5]decane 274913-93-8 C9H14O3
3-hydroxy-2-oxo-1-oxaspiro[4.5]decane
—— 4-(but-3-enyl)-2-propiolactone 360565-74-8 C7H10O2
4-(but-3-enyl)-2-propiolactone
—— 3,3,5-trimethyl-dihydrofuran-2(3H)-one 36763-77-6 C7H12O2
3,3,5-trimethyl-dihydrofuran-2(3H)-one
—— 6-phenyldihydro-2H-pyran-2,4(3H)-dione 92687-12-2 C11H10O3
6-phenyldihydro-2H-pyran-2,4(3H)-dione
—— (1S,5R)-1-(pyridin-3-yl)-3-oxabicyclo[3.1.0]hexan-2-one 947767-50-2 C10H9NO2
(1S,5R)-1-(pyridin-3-yl)-3-oxabicyclo[3.1.0]hexan-2-one
—— (Z)-3-(4-oxooxetan-2-yl)prop-2-enal 301849-84-3 C6H6O3
(Z)-3-(4-oxooxetan-2-yl)prop-2-enal
—— α-butyl-β-hydroxybutyrolactone 87683-10-1 C8H14O3
α-butyl-β-hydroxybutyrolactone
—— tetrahydro-2-oxo-5-phenyl-3-furancarbonitrile 33574-07-1 C11H9NO2
tetrahydro-2-oxo-5-phenyl-3-furancarbonitrile
—— (4S,5S)-4-Acetyl-5-phenyl-dihydro-furan-2-one 95891-75-1 C12H12O3
(4S,5S)-4-Acetyl-5-phenyl-dihydro-furan-2-one
—— (1R,5S)-1-(1-pyridin-2-yl-1H-imidazol-4-yl)-3-oxabicyclo[3.1.0]hexan-2-one 1334541-49-9 C13H11N3O2
(1R,5S)-1-(1-pyridin-2-yl-1H-imidazol-4-yl)-3-oxabicyclo[3.1.0]hexan-2-one
—— 1-oxaspiro[3.5]nonan-2-one 1483-09-6 C8H12O2
1-oxaspiro[3.5]nonan-2-one
—— methylketene dimer 476365-25-0 C6H8O2
methylketene dimer
—— (R)-4-(hex-4-ynyl)oxetan-2-one 1259544-62-1 C9H12O2
(R)-4-(hex-4-ynyl)oxetan-2-one
—— (R)-4-(methoxymethyl)oxetan-2-one 1259544-52-9 C5H8O3
(R)-4-(methoxymethyl)oxetan-2-one
—— 4-(hept-1-ynyl)oxetan-2-one 1257518-19-6 C10H14O2
4-(hept-1-ynyl)oxetan-2-one
—— (S)-4-Dec-9-enyl-oxetan-2-one 252873-92-0 C13H22O2
(S)-4-Dec-9-enyl-oxetan-2-one
—— 4-(cyclohexylethynyl)oxetan-2-one 1257518-22-1 C11H14O2
4-(cyclohexylethynyl)oxetan-2-one
—— (R)-4-(trimethylsilanyl-ethynyl) oxetan-2-one 310905-63-6 C8H12O2Si
(R)-4-(trimethylsilanyl-ethynyl) oxetan-2-one
—— (3S,4S)-(-)-cis-dimethyl-(γ)-butyrolactone 80009-59-2 C6H10O2
(3S,4S)-(-)-cis-dimethyl-(γ)-butyrolactone
—— (4S)-4-((2RS)-2-methoxyundecyl)oxetan-2-one 1193905-16-6 C15H28O3
(4S)-4-((2RS)-2-methoxyundecyl)oxetan-2-one
—— (4R)-4-((2RS)-2-methoxyundecyl)oxetan-2-one 1193905-12-2 C15H28O3
(4R)-4-((2RS)-2-methoxyundecyl)oxetan-2-one
—— (+/-)-5-octyn-4-olide 133399-88-9 C8H10O2
(+/-)-5-octyn-4-olide
—— (R)-5-((R)-1-hydroxyethyl)dihydrofuran-2(3H)-one 130609-14-2 C6H10O3
(R)-5-((R)-1-hydroxyethyl)dihydrofuran-2(3H)-one
—— camphoric anhydride 595-31-3 C10H14O3
camphoric anhydride
—— 5,5-Diethyl-4-phenyl-dihydro-furan-2-one 188646-70-0 C14H18O2
5,5-Diethyl-4-phenyl-dihydro-furan-2-one
—— 4,4-diethylbutyrolactone 1608-93-1 C8H14O2
4,4-diethylbutyrolactone
—— Ethyl tetrahydro-6,6-dimethyl-α,2-dioxo-2H-pyran-3-acetate 20473-94-3 C10H16O4
Ethyl tetrahydro-6,6-dimethyl-α,2-dioxo-2H-pyran-3-acetate
—— 4-(1'-chloroacetoxycyclohexan-1'-yl)butanolide 946617-06-7 C12H17ClO4
4-(1'-chloroacetoxycyclohexan-1'-yl)butanolide
—— 5-hydroxymethyl-3-methylbutyrolactone 51577-65-2 C6H10O3
5-hydroxymethyl-3-methylbutyrolactone
—— bicyclo<4.2.0>octane-7,8-dicarboxylate anhydride 6537-93-5 C10H12O3
bicyclo<4.2.0>octane-7,8-dicarboxylate anhydride
—— (4R,5S)-(5-tert-butyldimethylsilyloxymethyl)-4-(hydroxymethyl)tetrahydrofuran-2-one 164848-06-0 C12H24O4Si
(4R,5S)-(5-tert-butyldimethylsilyloxymethyl)-4-(hydroxymethyl)tetrahydrofuran-2-one
—— 5-(3-furyl)tetrahydrofuran-2-one 51593-62-5 C8H8O3
5-(3-furyl)tetrahydrofuran-2-one
—— 3,4-dimethyl-5-oxotetrahydrofuran-3-yl acetate 1004788-37-7 C8H12O4
3,4-dimethyl-5-oxotetrahydrofuran-3-yl acetate
—— 3-Hydroxy-2,3-dimethylbutanolid 80248-68-6 C6H10O3
3-Hydroxy-2,3-dimethylbutanolid
—— 4-ethyl-3-methyl-5-oxotetrahydrofuran-3-yl acetate 1004788-36-6 C9H14O4
4-ethyl-3-methyl-5-oxotetrahydrofuran-3-yl acetate
—— (4R,6S)-4-(1,1-dimethylallyl)-6-furan-3-yl-tetrahydropyran-2-one 342641-10-5 C14H18O3
(4R,6S)-4-(1,1-dimethylallyl)-6-furan-3-yl-tetrahydropyran-2-one
—— 5-(3'-furyl)-3-methylidenetetrahydrofuran-2-one 1314552-04-9 C9H8O3
5-(3'-furyl)-3-methylidenetetrahydrofuran-2-one
—— (3S,4R,6S)-3-allyl-4-(1,1-dimethylallyl)-6-furan-3-yl-tetrahydropyran-2-one 342641-11-6 C17H22O3
(3S,4R,6S)-3-allyl-4-(1,1-dimethylallyl)-6-furan-3-yl-tetrahydropyran-2-one
—— 1-methylpropyl-2-oxotetrahydrofurane 77755-97-6 C8H14O2
1-methylpropyl-2-oxotetrahydrofurane
—— (4R)-4-phenyltetrahydro-2H-pyran-2-one 71302-21-1 C11H12O2
(4R)-4-phenyltetrahydro-2H-pyran-2-one
—— (Z)-3-benzylidene-5-cyclohexyldihydrofuran-2(3H)-one 328041-66-3 C17H20O2
(Z)-3-benzylidene-5-cyclohexyldihydrofuran-2(3H)-one
—— (Z)-α-benzylidene-γ-butyrolactone 40011-26-5 C11H10O2
(Z)-α-benzylidene-γ-butyrolactone
—— dimethylaminomicheliolide 1403357-81-2 C17H27NO3
dimethylaminomicheliolide
—— (1S,5R,6S)-6-ethyl-3-oxabicyclo[3.1.0]hexan-2-one 141041-90-9 C7H10O2
(1S,5R,6S)-6-ethyl-3-oxabicyclo[3.1.0]hexan-2-one
—— 4,5,5-trimethyltetrahydrofuran-2-one 169891-56-9 C7H12O2
4,5,5-trimethyltetrahydrofuran-2-one
—— 3-methylene-4,5,5-trimethyltetrahydrofuran-2-one 49576-63-8 C8H12O2
3-methylene-4,5,5-trimethyltetrahydrofuran-2-one