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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
—— 3,5-bis(tert-butyl-diphenylsilyloxy)-2-deoxy-2,2-difluoro-1-oxoribose 924264-45-9 C37H42F2O4Si2
3,5-bis(tert-butyl-diphenylsilyloxy)-2-deoxy-2,2-difluoro-1-oxoribose
—— 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-2,2-difluoro-1-oxoribose 95058-78-9 C17H34F2O4Si2
3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-2,2-difluoro-1-oxoribose
—— (3R,4S,5S)-3-methyl-4-(nitromethyl)-5-undecyloxolan-2-one 1452900-14-9 C17H31NO4
(3R,4S,5S)-3-methyl-4-(nitromethyl)-5-undecyloxolan-2-one
—— 3-Oxabicyclo<3.1.0>hexan-2-one-1-carboxylic acid ethyl ester 14208-48-1 C8H10O4
3-Oxabicyclo<3.1.0>hexan-2-one-1-carboxylic acid ethyl ester
—— dihydro-3-cyano-5-octyl-2(3H)-furanone 102681-95-8 C13H21NO2
dihydro-3-cyano-5-octyl-2(3H)-furanone
—— 5,5-bis[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-3-(1-hydroxydecyl)-3,4,5-trihydrofuran-2-one 261357-16-8 C48H66O5Si2
5,5-bis[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-3-(1-hydroxydecyl)-3,4,5-trihydrofuran-2-one
—— (3S,4S,5R)-3-Ethyl-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one 167968-03-8 C7H12O4
(3S,4S,5R)-3-Ethyl-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one
—— 3,3-diethyl-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one 827017-69-6 C10H18O3
3,3-diethyl-5-(2-hydroxyethyl)dihydrofuran-2(3H)-one
—— (S)-4-isopropyl tetrahydropyran-2-one 61949-74-4 C8H14O2
(S)-4-isopropyl tetrahydropyran-2-one
—— dihydromikanolide 23758-04-5 C15H16O6
dihydromikanolide
—— 3,5,6-trideoxy-6-phenyl-D-gulono-1,4-lactone 1262043-22-0 C12H14O3
3,5,6-trideoxy-6-phenyl-D-gulono-1,4-lactone
—— (5SR,6SR)-5,6-dimethyltetrahydropyran-2-one 24405-15-0 C7H12O2
(5SR,6SR)-5,6-dimethyltetrahydropyran-2-one
—— 6-methyl-1-oxa-spiro[4.5]decan-2-one 16332-62-0 C10H16O2
6-methyl-1-oxa-spiro[4.5]decan-2-one
—— (+/-)-isopilopic acid 487-72-9 C7H10O4
(+/-)-isopilopic acid
—— (+)-isopilopic acid 1195158-00-9 C7H10O4
(+)-isopilopic acid
—— 3,5,7-trimethyloxepan-2-one —— C9H16O2
3,5,7-trimethyloxepan-2-one
—— (R,S)-5-formyldihydro-2(3H)-furanone 27620-83-3 C5H6O3
(R,S)-5-formyldihydro-2(3H)-furanone
—— Hexahydrocyclopenta[c]pyran-1(3H)-one 5732-99-0 C8H12O2
Hexahydrocyclopenta[c]pyran-1(3H)-one
—— 6-bromo-6-deoxy-D-mannono-1,4-lactone 161085-43-4 C6H9BrO5
6-bromo-6-deoxy-D-mannono-1,4-lactone
—— 6-bromo-6-deoxy-D-galactono-1,4-lactone 161085-33-2 C6H9BrO5
6-bromo-6-deoxy-D-galactono-1,4-lactone
—— γ-Methyl,γ-n-Propylbutyrolacton 3284-93-3 C8H14O2
γ-Methyl,γ-n-Propylbutyrolacton
—— dipropyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3 —— C15H22O2
dipropyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.0<sup>2.6</sup>>decene-8 one-3
—— (4R,5S,Z)-3-butylidene-4-hydroxy-5-methyldihydrofuran-2(3H)-one 1417335-38-6 C9H14O3
(4R,5S,Z)-3-butylidene-4-hydroxy-5-methyldihydrofuran-2(3H)-one
—— 6-methyl-3-phenyltetrahydro-2H-pyran-2-one 90124-77-9 C12H14O2
6-methyl-3-phenyltetrahydro-2H-pyran-2-one
—— (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-1-carbamoyl-2-phenyl-ethyl ester 192864-48-5 C19H23NO5
(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-1-carbamoyl-2-phenyl-ethyl ester
—— dihydro-3-chloropropylfuran-2(3H)-one 19446-81-2 C7H11ClO2
dihydro-3-chloropropylfuran-2(3H)-one
—— 5-(tert-butyl)dihydrofuran-2(3H)-one 21175-44-0 C8H14O2
5-(tert-butyl)dihydrofuran-2(3H)-one
—— 2-oxabicyclo[3.2.1]octan-3-one 5724-61-8 C7H10O2
2-oxabicyclo[3.2.1]octan-3-one
—— 4-nonylidene-3-octyl-oxetan-2-one 58712-53-1 C20H36O2
4-nonylidene-3-octyl-oxetan-2-one
—— γ-(5-norbornen-2-yl)methyl-γ-butyrolactone 391241-43-3 C12H16O2
γ-(5-norbornen-2-yl)methyl-γ-butyrolactone
—— O-ethyl S-1-(ethylthio)-2-(2-oxotetrahydrofuran-3-yl)ethyl carbonodithioate 1263775-95-6 C11H18O3S3
O-ethyl S-1-(ethylthio)-2-(2-oxotetrahydrofuran-3-yl)ethyl carbonodithioate
—— 7,9,9-trimethyl-1-oxaspiro-<4,5>-6-decen-2-one 144648-11-3 C12H18O2
7,9,9-trimethyl-1-oxaspiro-<4,5>-6-decen-2-one
—— (3R,4S)(-) eldanolide 85505-80-2 C10H16O2
(3R,4S)(-) eldanolide
—— (1S,5R,6S)-6-Diethoxymethyl-2-oxabicyclo-[3,3,0]octan-3-one 69691-56-1 C12H20O4
(1S,5R,6S)-6-Diethoxymethyl-2-oxabicyclo-[3,3,0]octan-3-one
—— α-cyano-γ,γ-dimethyl-γ-butyrolactone 59909-84-1 C7H9NO2
α-cyano-γ,γ-dimethyl-γ-butyrolactone
—— 3-cyano-5-methyl-4,5-dihydro-2(3H)-furanone 76263-39-3 C6H7NO2
3-cyano-5-methyl-4,5-dihydro-2(3H)-furanone
—— 3-Ethyl-2-oxaspiro[4.4]nonan-1-one 65757-11-1 C10H16O2
3-Ethyl-2-oxaspiro[4.4]nonan-1-one
—— (+/-)-5-Dimethylaminomethyl-4,5-dihydro-2(3H)-furanon-Methobromid 166942-31-0 Br*C8H16NO2
(+/-)-5-Dimethylaminomethyl-4,5-dihydro-2(3H)-furanon-Methobromid
—— 3H,6H-3a,8b-Methano-1H-indeno[4,5-c]furan-4-carboxaldehyde,5a,7,8,8a-tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo- (9CI) 2212-99-9 C15H18O4
3H,6H-3a,8b-Methano-1H-indeno[4,5-c]furan-4-carboxaldehyde,5a,7,8,8a-tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo- (9CI)
—— r-4,t-5-dibromo-c-5-methyloxolan-2-one 1424-35-7 C5H6Br2O2
r-4,t-5-dibromo-c-5-methyloxolan-2-one
—— α-cyclohexylcarbonyl-γ-butyrolactone 58688-33-8 C11H16O3
α-cyclohexylcarbonyl-γ-butyrolactone
—— 3,3-Dimethyl-2-oxaspiro[4.5]decan-1-one 258264-45-8 C11H18O2
3,3-Dimethyl-2-oxaspiro[4.5]decan-1-one
—— 4'-methylcyclohexanespiro-3'-(tetrahydrofuran)-2'-one 82918-80-7 C10H16O2
4'-methylcyclohexanespiro-3'-(tetrahydrofuran)-2'-one
—— 3-chloromethyl-2-oxaspiro[4.5]decan-1-one 205528-11-6 C10H15ClO2
3-chloromethyl-2-oxaspiro[4.5]decan-1-one
—— 2-oxaspiro<3.5>nona-1-one 2313-04-4 C8H12O2
2-oxaspiro<3.5>nona-1-one
—— 3-ethyl-4-methyl-oxetan-2-one 114592-79-9 C6H10O2
3-ethyl-4-methyl-oxetan-2-one
—— 6-cyclopentyl-6-[2-(4-hydroxyphenyl)ethyl]dihydropyran-2,4-dione 625445-17-2 C18H22O4
6-cyclopentyl-6-[2-(4-hydroxyphenyl)ethyl]dihydropyran-2,4-dione
—— 3-Isopropyloxetan-2-one 25250-54-8 C6H10O2
3-Isopropyloxetan-2-one
—— methyl (1R,5R,6R)-6-methyl-2,7-dioxo-3-oxabicyclo<3.3.0>octane-6-carboxylate 124225-08-7 C10H12O5
methyl (1R,5R,6R)-6-methyl-2,7-dioxo-3-oxabicyclo<3.3.0>octane-6-carboxylate
—— (3S)-{[(1S)-1-ethyl-3-trimethylsilylpropynyl]oxy}tetrahydrofuran-2-one 488703-65-7 C12H20O3Si
(3S)-{[(1S)-1-ethyl-3-trimethylsilylpropynyl]oxy}tetrahydrofuran-2-one