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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
—— (4R,5R)-5-methyl-4-phenyl-4,5-dihydro-2(3H)-furanone —— C11H12O2
(4R,5R)-5-methyl-4-phenyl-4,5-dihydro-2(3H)-furanone
—— 6-methoxy-3-methyl-3,3a,6,6a-tetrahydro-4H-furo[3,4-c]pyrazol-4-one —— C7H10N2O3
6-methoxy-3-methyl-3,3a,6,6a-tetrahydro-4H-furo[3,4-c]pyrazol-4-one
—— (+/-)-(3aR,5aR,8aS,8bS)-1,8,8a,8b-tetrahydrobenzofuro[5,4-b]furan-2,7(3aH,5aH)-dione —— C10H10O4
(+/-)-(3aR,5aR,8aS,8bS)-1,8,8a,8b-tetrahydrobenzofuro[5,4-b]furan-2,7(3aH,5aH)-dione
—— 2-chloro-2-methyl-3-(2-oxapropoxy)-γ-butyrolacton —— C7H11ClO4
2-chloro-2-methyl-3-(2-oxapropoxy)-γ-butyrolacton
—— (6,6-dimethyl-9-oxo)-3,5-dithia-8-oxabicyclo[5, 2, 1]decane —— C9H14O2S2
(6,6-dimethyl-9-oxo)-3,5-dithia-8-oxabicyclo[5, 2, 1]decane
—— cis-4-(1-mercapto-1-methylethyl)-2-mercaptomethyl-4-butanolide —— C8H14O2S2
cis-4-(1-mercapto-1-methylethyl)-2-mercaptomethyl-4-butanolide
—— 3-(5-bromopentyl)furan-2,4(3H,5H)-dione —— C9H13BrO3
3-(5-bromopentyl)furan-2,4(3H,5H)-dione
—— (4S)-4-amino-tetrahydrofuran-2-one —— C4H7NO2
(4S)-4-amino-tetrahydrofuran-2-one
—— 3-methylene-5-tridecyltetrahydrofuran-2-one —— C18H32O2
3-methylene-5-tridecyltetrahydrofuran-2-one
—— (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl ester —— C16H19NO5
(5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl ester
—— rubrenolide —— C17H30O4
rubrenolide
—— rubrenolide —— C17H30O4
rubrenolide
—— (+/-)-anti-2-allyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone —— C9H14O3
(+/-)-anti-2-allyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone
—— 2-<1-(N-sec-butylamino)ethylidene>butyrolactone —— C10H17NO2
2-<1-(N-sec-butylamino)ethylidene>butyrolactone
—— (+/-)-anti-2-propyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone —— C9H16O3
(+/-)-anti-2-propyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone
—— 2-<1-(N-propylamino)ethylidene>butyrolactone —— C9H15NO2
2-<1-(N-propylamino)ethylidene>butyrolactone
—— (+/-)-syn-2-propyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone —— C9H16O3
(+/-)-syn-2-propyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone
—— 2-<1-(N-isopropylamino)-2,2-diethoxyethylidene>butyrolactone —— C13H23NO4
2-<1-(N-isopropylamino)-2,2-diethoxyethylidene>butyrolactone
—— 4',5'-dihydro-3'H-[2,3']bifuranyl-2'-one —— C8H8O3
4',5'-dihydro-3'H-[2,3']bifuranyl-2'-one
—— 3-bromo-4',5'-dihydro-3'H-[2,3']bifuranyl-2'-one —— C8H7BrO3
3-bromo-4',5'-dihydro-3'H-[2,3']bifuranyl-2'-one
—— (3S,1'R)-dihydro-3-(1'-aminoethyl)-2(3H)-furanone —— C6H11NO2
(3S,1'R)-dihydro-3-(1'-aminoethyl)-2(3H)-furanone
—— (S)-3-acetyl-3-chlorodihydrofuran-2(3H)-one —— C6H7ClO3
(S)-3-acetyl-3-chlorodihydrofuran-2(3H)-one
—— (3R)-dihydro-3-((R)-1-aminoethyl)-2(3H)-furanone —— C6H11NO2
(3R)-dihydro-3-((R)-1-aminoethyl)-2(3H)-furanone
—— 2-<1-(N-isopropylamino)ethylidene>butyrolactone —— C9H15NO2
2-<1-(N-isopropylamino)ethylidene>butyrolactone
—— 2-fluoro-2-(fluoroacetyl) butyrolactone —— C6H6F2O3
2-fluoro-2-(fluoroacetyl) butyrolactone
—— α-acetyl-α-phenyl-γ-butyrolactone —— C12H12O3
α-acetyl-α-phenyl-γ-butyrolactone
—— 3-acetyl-3-fluorodihydrofuran-2(3H)-one —— C6H7FO3
3-acetyl-3-fluorodihydrofuran-2(3H)-one
—— 3-acetyl-3-(3-oxocyclopentyl)dihydrofuran-2-one —— C11H14O4
3-acetyl-3-(3-oxocyclopentyl)dihydrofuran-2-one
—— 2-(1-aminoethylidene)butyrolactone —— C6H9NO2
2-(1-aminoethylidene)butyrolactone
—— 3-((Z)-1-allylamino-ethylidene)-dihydro-furan-2-one —— C9H13NO2
3-((Z)-1-allylamino-ethylidene)-dihydro-furan-2-one
—— 3-acetyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one —— C9H10O3
3-acetyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one
—— methyl (S)-1-((S)-3-acetyl-tetrahydro-2-oxofuran-3-yl)-3-phenylpropylcarbamate —— C17H21NO5
methyl (S)-1-((S)-3-acetyl-tetrahydro-2-oxofuran-3-yl)-3-phenylpropylcarbamate
—— 3-acetyl-3-(2-nitro-1-phenylethyl)dihydrofuran-2(3H)-one —— C14H15NO5
3-acetyl-3-(2-nitro-1-phenylethyl)dihydrofuran-2(3H)-one
—— methyl 1-methylene-6-oxo-2,7-dioxaspiro[4,4]nonane-3-carboxylate —— C10H12O5
methyl 1-methylene-6-oxo-2,7-dioxaspiro[4,4]nonane-3-carboxylate
—— (±)-3-acetyl-3-(pent-4-yn-1-yl)dihydrofuran-2(3H)-one —— C11H14O3
(±)-3-acetyl-3-(pent-4-yn-1-yl)dihydrofuran-2(3H)-one
—— 2-acetyl-2-(pent-5-en-1-yl)-γ-butyrolactone —— C11H16O3
2-acetyl-2-(pent-5-en-1-yl)-γ-butyrolactone
—— 3-(3-acetyl-2-oxotetrahydrofuran-3-yl)-1-benzylpyrrolidine-2,5-dione —— C17H17NO5
3-(3-acetyl-2-oxotetrahydrofuran-3-yl)-1-benzylpyrrolidine-2,5-dione
—— 3-[1-[(trimethylsilyl)oxy]ethylidenyl]-4,5-dihydrofuran-2-one —— C9H16O3Si
3-[1-[(trimethylsilyl)oxy]ethylidenyl]-4,5-dihydrofuran-2-one
—— (Z)-1-(1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl)urea —— C7H10N2O3
(Z)-1-(1-(2-oxodihydrofuran-3(2H)-ylidene)ethyl)urea
—— (E)-2-(2-γ-butyrolactonylidene)-5-vinyltetrahydrofuran —— C10H12O3
(E)-2-(2-γ-butyrolactonylidene)-5-vinyltetrahydrofuran
—— 3-[1-(2-hydroxyethylamino)ethylidene]tetrahydrofuran-2-one —— C8H13NO3
3-[1-(2-hydroxyethylamino)ethylidene]tetrahydrofuran-2-one
—— (R)-2-(5-oxotetrahydrofuran-3-yl)acetaldehyde —— C6H8O3
(R)-2-(5-oxotetrahydrofuran-3-yl)acetaldehyde
—— 3,7,7-trimethyl-6-oxo-1,4-bis(trifluoromethanesulfonyl)-1,4,4a,6,7,7a-hexahydrofuro[2,3-b]pyrazine —— C11H12F6N2O6S2
3,7,7-trimethyl-6-oxo-1,4-bis(trifluoromethanesulfonyl)-1,4,4a,6,7,7a-hexahydrofuro[2,3-b]pyrazine
—— 4-(2-pentyl)butyrolactone —— C9H16O2
4-(2-pentyl)butyrolactone
—— (E)-2-(5-ethyl-2-oxotetrahydrofuran-3-ylidene)tetrahydrofuran —— C10H14O3
(E)-2-(5-ethyl-2-oxotetrahydrofuran-3-ylidene)tetrahydrofuran
—— dimethyl 7,7-dimethyl-6-oxo-4a,6,7,7a-tetrahydrofuro[2,3-b]pyrazine-1,4-dicarboxylate —— C12H16N2O6
dimethyl 7,7-dimethyl-6-oxo-4a,6,7,7a-tetrahydrofuro[2,3-b]pyrazine-1,4-dicarboxylate
—— dimethyl 7',7'-dimethyl-6'-oxospiro[cyclohexane-1,4'-(4a,6,7,7a-tetrahydrofuro[2,3-b]pyrazine)]-1',4'-dicarboxylate —— C15H20N2O6
dimethyl 7',7'-dimethyl-6'-oxospiro[cyclohexane-1,4'-(4a,6,7,7a-tetrahydrofuro[2,3-b]pyrazine)]-1',4'-dicarboxylate
—— 9,10,12,13-tetramethyl-14-oxatrispiro<2.1.2.0.5.2>pentadeca-9,12-diene-4,11,15-trione —— C18H20O4
9,10,12,13-tetramethyl-14-oxatrispiro<2.1.2.0.5.2>pentadeca-9,12-diene-4,11,15-trione
—— 3-(4-(dibutylamino)but-2-ynyl)-5-(propoxymethyl)dihydrofuran-2(3H)-one —— C20H35NO3
3-(4-(dibutylamino)but-2-ynyl)-5-(propoxymethyl)dihydrofuran-2(3H)-one
—— (3S*,4S*)-3-allyl-4-vinyldihydrofuran-2-one —— C9H12O2
(3S*,4S*)-3-allyl-4-vinyldihydrofuran-2-one