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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
—— [(3S,5S)-5-methyl-2-oxooxolan-3-yl] N,N-diethylcarbamodithioate —— C10H17NO2S2
[(3S,5S)-5-methyl-2-oxooxolan-3-yl] N,N-diethylcarbamodithioate
—— [(3R,5S)-5-methyl-2-oxooxolan-3-yl] N,N-diethylcarbamodithioate —— C10H17NO2S2
[(3R,5S)-5-methyl-2-oxooxolan-3-yl] N,N-diethylcarbamodithioate
—— [(3R,5R)-5-methyl-2-oxooxolan-3-yl] N,N-diethylcarbamodithioate —— C10H17NO2S2
[(3R,5R)-5-methyl-2-oxooxolan-3-yl] N,N-diethylcarbamodithioate
—— (4R)-4-(5-amino-1,2,4-triazol-1-yl)oxolan-2-one —— C6H8N4O2
(4R)-4-(5-amino-1,2,4-triazol-1-yl)oxolan-2-one
—— (4S)-4-(5-amino-1,2,4-triazol-1-yl)oxolan-2-one —— C6H8N4O2
(4S)-4-(5-amino-1,2,4-triazol-1-yl)oxolan-2-one
—— (4R)-N-methyl-2-oxo-N-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1-oxaspiro[4.5]decane-4-carboxamide —— C21H24N2O4
(4R)-N-methyl-2-oxo-N-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1-oxaspiro[4.5]decane-4-carboxamide
—— (4S)-N-methyl-2-oxo-N-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1-oxaspiro[4.5]decane-4-carboxamide —— C21H24N2O4
(4S)-N-methyl-2-oxo-N-[(3-phenyl-1,2-oxazol-5-yl)methyl]-1-oxaspiro[4.5]decane-4-carboxamide
—— [(1R,2S,4R,5S,7S,10S,11S,14S,15S,16S,18S,19S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadecane-15,2'-oxolane]-7-yl] hydrogen sulfate —— C24H34O6S
[(1R,2S,4R,5S,7S,10S,11S,14S,15S,16S,18S,19S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadecane-15,2'-oxolane]-7-yl] hydrogen sulfate
—— [(1R,2S,4R,5S,7R,10S,11S,14S,15S,16S,18S,19S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadecane-15,2'-oxolane]-7-yl] hydrogen sulfate —— C24H34O6S
[(1R,2S,4R,5S,7R,10S,11S,14S,15S,16S,18S,19S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadecane-15,2'-oxolane]-7-yl] hydrogen sulfate
—— [(4R,8S,9R,11S)-11-methyl-2,7-dimethylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C19H20O6
[(4R,8S,9R,11S)-11-methyl-2,7-dimethylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— [(4R,8S,9S,11S)-11-methyl-2,7-dimethylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C19H20O6
[(4R,8S,9S,11S)-11-methyl-2,7-dimethylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— [(4R,8S,9S,11R)-11-methyl-2,7-dimethylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C19H20O6
[(4R,8S,9S,11R)-11-methyl-2,7-dimethylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— [(4R,7R,8S,9R,11S)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C20H24O7
[(4R,7R,8S,9R,11S)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— [(4R,7R,8S,9S,11S)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C20H24O7
[(4R,7R,8S,9S,11S)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— [(4R,7R,8S,9R,11R)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C20H24O7
[(4R,7R,8S,9R,11R)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— [(4R,7R,8S,9S,11R)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate —— C20H24O7
[(4R,7R,8S,9S,11R)-7-(methoxymethyl)-11-methyl-2-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-1(13)-en-9-yl] 2-methylprop-2-enoate
—— (2R)-5-oxo-N-(1,3-thiazol-2-ylmethyl)-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide —— C16H20N4O3S
(2R)-5-oxo-N-(1,3-thiazol-2-ylmethyl)-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide
—— (2S)-5-oxo-N-(1,3-thiazol-2-ylmethyl)-N-(2,2,2-trifluoroethyl)oxolane-2-carboxamide —— C11H11F3N2O3S
(2S)-5-oxo-N-(1,3-thiazol-2-ylmethyl)-N-(2,2,2-trifluoroethyl)oxolane-2-carboxamide
—— (2S)-5-oxo-N-(1,3-thiazol-2-ylmethyl)-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide —— C16H20N4O3S
(2S)-5-oxo-N-(1,3-thiazol-2-ylmethyl)-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide
—— (2S)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxooxolane-2-carboxamide —— C16H20ClN5O3
(2S)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2R)-N-[(2,5-dimethylpyrazol-3-yl)methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide —— C22H24N4O4
(2R)-N-[(2,5-dimethylpyrazol-3-yl)methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxooxolane-2-carboxamide —— C16H20ClN5O3
(2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-5-oxooxolane-2-carboxamide —— C14H18ClN3O5
(2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-5-oxooxolane-2-carboxamide
—— (2S)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-5-oxo-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide —— C17H22ClN5O3
(2S)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-5-oxo-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide
—— (5S)-5-(azidomethyl)-3,3-difluorooxolan-2-one —— C5H5F2N3O2
(5S)-5-(azidomethyl)-3,3-difluorooxolan-2-one
—— (2R)-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide —— C15H18N4O3S
(2R)-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide
—— (2S)-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide —— C20H19N3O4S
(2S)-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide
—— (2S)-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide —— C15H18N4O3S
(2S)-N-[(1,5-dimethylpyrazol-3-yl)methyl]-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide
—— (1S,4R)-N-methoxy-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C11H17NO4
(1S,4R)-N-methoxy-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,4S)-N-methoxy-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C11H17NO4
(1R,4S)-N-methoxy-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (1R,4S)-4,7,7-trimethyl-N-(3-methylbutyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C15H25NO3
(1R,4S)-4,7,7-trimethyl-N-(3-methylbutyl)-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (2R)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide —— C23H26N2O4
(2R)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2S)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide —— C23H26N2O4
(2S)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide —— C23H26N2O4
(2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2S)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide —— C23H26N2O4
(2S)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-5-oxooxolane-2-carboxamide
—— (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(1,3-dioxolan-2-ylmethyl)-5-oxooxolane-2-carboxamide —— C16H23NO5
(2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(1,3-dioxolan-2-ylmethyl)-5-oxooxolane-2-carboxamide
—— (2R)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-5-oxo-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide —— C19H27N3O3
(2R)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-5-oxo-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide
—— (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-5-oxo-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide —— C19H27N3O3
(2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-5-oxo-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]oxolane-2-carboxamide
—— (2S)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(1,3-dioxolan-2-ylmethyl)-5-oxooxolane-2-carboxamide —— C16H23NO5
(2S)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(1,3-dioxolan-2-ylmethyl)-5-oxooxolane-2-carboxamide
—— (2S)-5-oxo-N-(2-phenylethyl)-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide —— C17H18N2O3S
(2S)-5-oxo-N-(2-phenylethyl)-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide
—— (2R)-N-(2-methylpropyl)-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide —— C13H18N2O3S
(2R)-N-(2-methylpropyl)-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide
—— (2S)-N-(2-methylpropyl)-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide —— C13H18N2O3S
(2S)-N-(2-methylpropyl)-5-oxo-N-(1,3-thiazol-2-ylmethyl)oxolane-2-carboxamide
—— (2R)-N-(furan-2-ylmethyl)-5-oxo-N-(2-phenylethyl)oxolane-2-carboxamide —— C18H19NO4
(2R)-N-(furan-2-ylmethyl)-5-oxo-N-(2-phenylethyl)oxolane-2-carboxamide
—— (3R,5S)-3-benzyl-5-hydroxyoxolan-2-one —— C11H12O3
(3R,5S)-3-benzyl-5-hydroxyoxolan-2-one
—— (1R,5S)-1-(2-fluorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one —— C11H9FO2
(1R,5S)-1-(2-fluorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
—— (3S,5S)-3-benzyl-5-hydroxyoxolan-2-one —— C11H12O3
(3S,5S)-3-benzyl-5-hydroxyoxolan-2-one
—— (3S,5R)-3-benzyl-5-hydroxyoxolan-2-one —— C11H12O3
(3S,5R)-3-benzyl-5-hydroxyoxolan-2-one
—— (3R,5R)-3-benzyl-5-hydroxyoxolan-2-one —— C11H12O3
(3R,5R)-3-benzyl-5-hydroxyoxolan-2-one
—— (4R,6R)-4,6-dihydroxy-4-(trifluoromethyl)oxan-2-one —— C6H7F3O4
(4R,6R)-4,6-dihydroxy-4-(trifluoromethyl)oxan-2-one
—— (4S,6S)-4,6-dihydroxy-4-(trifluoromethyl)oxan-2-one —— C6H7F3O4
(4S,6S)-4,6-dihydroxy-4-(trifluoromethyl)oxan-2-one