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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
—— (1R,2S,3S,4S,7S,11R,12R,13S,16S,20S,21S,22R)-4,13-dimethyl-6,15-dioxaoctacyclo[11.8.1.02,12.03,7.04,21.07,11.016,20.016,22]docosane-5,14-dione —— C22H26O4
(1R,2S,3S,4S,7S,11R,12R,13S,16S,20S,21S,22R)-4,13-dimethyl-6,15-dioxaoctacyclo[11.8.1.02,12.03,7.04,21.07,11.016,20.016,22]docosane-5,14-dione
—— (1R,2R,3S,4R,7S,10S,11R,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C21H24O4S
(1R,2R,3S,4R,7S,10S,11R,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1S,2R,3S,4R,7S,10R,11R,12R,13S,14S,15S,18R,21S,22S)-10,21-dimethyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C22H26O4
(1S,2R,3S,4R,7S,10R,11R,12R,13S,14S,15S,18R,21S,22S)-10,21-dimethyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2R,3S,4R,7S,10R,11S,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C21H24O4S
(1R,2R,3S,4R,7S,10R,11S,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2R,3S,4R,7S,10S,11S,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C21H24O4S
(1R,2R,3S,4R,7S,10S,11S,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1S,2R,3S,4R,7S,10S,11R,12R,13S,14S,15S,18R,21S,22S)-10,21-dimethyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C22H26O4
(1S,2R,3S,4R,7S,10S,11R,12R,13S,14S,15S,18R,21S,22S)-10,21-dimethyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2R,3S,4R,7S,10R,11R,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C21H24O4S
(1R,2R,3S,4R,7S,10R,11R,12R,13S,14S,15R,18R,21S,22S)-10-methylsulfanyl-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1S,2R,3R,4S,7S,11S,12R,13R,16S,20R,21R,22S)-4,13-dimethyl-6,15-dioxaoctacyclo[11.8.1.02,12.03,7.04,21.07,11.016,20.016,22]docosane-5,14-dione —— C22H26O4
(1S,2R,3R,4S,7S,11S,12R,13R,16S,20R,21R,22S)-4,13-dimethyl-6,15-dioxaoctacyclo[11.8.1.02,12.03,7.04,21.07,11.016,20.016,22]docosane-5,14-dione
—— (1R,2S,3R,4R,7S,10R,11R,12R,13S,14S,15S,18R,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C20H22O4
(1R,2S,3R,4R,7S,10R,11R,12R,13S,14S,15S,18R,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2S,3R,4R,7S,10R,11R,12R,13S,14R,15S,18S,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C20H22O4
(1R,2S,3R,4R,7S,10R,11R,12R,13S,14R,15S,18S,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2S,3R,4R,7S,10R,11R,12R,13S,14R,15S,18R,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C20H22O4
(1R,2S,3R,4R,7S,10R,11R,12R,13S,14R,15S,18R,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2R,3S,4R,5R,8R,11S,12S,15R,18R,19S,20R)-9,14-dioxaheptacyclo[16.2.1.12,5.03,11.04,8.012,20.015,19]docosane-10,13-dione —— C20H24O4
(1R,2R,3S,4R,5R,8R,11S,12S,15R,18R,19S,20R)-9,14-dioxaheptacyclo[16.2.1.12,5.03,11.04,8.012,20.015,19]docosane-10,13-dione
—— (1R,2S,3R,4R,7S,10R,11R,12R,13S,14S,15S,18S,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione —— C20H22O4
(1R,2S,3R,4R,7S,10R,11R,12R,13S,14S,15S,18S,21R,22S)-8,19-dioxaoctacyclo[10.10.0.02,10.03,7.04,22.011,15.013,21.014,18]docosane-9,20-dione
—— (1R,2R,3S,4S,5R,8R,11S,12S,15R,18R,19R,20S)-9,14-dioxaheptacyclo[16.2.1.12,5.03,11.04,8.012,20.015,19]docosane-10,13-dione —— C20H24O4
(1R,2R,3S,4S,5R,8R,11S,12S,15R,18R,19R,20S)-9,14-dioxaheptacyclo[16.2.1.12,5.03,11.04,8.012,20.015,19]docosane-10,13-dione
—— (1S,2R,5S,8S,9R,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one —— C11H10O2
(1S,2R,5S,8S,9R,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one
—— (1S,2R,5R,8S,9S,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one —— C11H10O2
(1S,2R,5R,8S,9S,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one
—— (1S,2R,5S,8S,9S,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one —— C11H10O2
(1S,2R,5S,8S,9S,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one
—— (1S,2R,5R,8S,9R,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one —— C11H10O2
(1S,2R,5R,8S,9R,12R)-6-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-7-one
—— (1R,2S,6S,9S,10S)-4-oxo-5-oxatetracyclo[8.2.2.02,6.02,9]tetradeca-7,13-diene-11,11,12,12-tetracarbonitrile —— C17H10N4O2
(1R,2S,6S,9S,10S)-4-oxo-5-oxatetracyclo[8.2.2.02,6.02,9]tetradeca-7,13-diene-11,11,12,12-tetracarbonitrile
—— (1R,2R,6S,9S,10S)-4-oxo-5-oxatetracyclo[8.2.2.02,6.02,9]tetradeca-7,13-diene-11,11,12,12-tetracarbonitrile —— C17H10N4O2
(1R,2R,6S,9S,10S)-4-oxo-5-oxatetracyclo[8.2.2.02,6.02,9]tetradeca-7,13-diene-11,11,12,12-tetracarbonitrile
—— (1R,2S,6R,9S,10S)-4-oxo-5-oxatetracyclo[8.2.2.02,6.02,9]tetradeca-7,13-diene-11,11,12,12-tetracarbonitrile —— C17H10N4O2
(1R,2S,6R,9S,10S)-4-oxo-5-oxatetracyclo[8.2.2.02,6.02,9]tetradeca-7,13-diene-11,11,12,12-tetracarbonitrile
—— (1S,2R,5S,8S,9R,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one —— C11H10O2
(1S,2R,5S,8S,9R,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one
—— (1R,4S,7R,8R)-5-oxatricyclo[5.3.2.04,8]dodeca-2,9,11-trien-6-one —— C11H10O2
(1R,4S,7R,8R)-5-oxatricyclo[5.3.2.04,8]dodeca-2,9,11-trien-6-one
—— (1S,2R,5R,8S,9S,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one —— C11H10O2
(1S,2R,5R,8S,9S,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one
—— (1S,2R,5R,8S,9R,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one —— C11H10O2
(1S,2R,5R,8S,9R,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one
—— (1S,2S,3R,6S,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one —— C11H10O2
(1S,2S,3R,6S,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one
—— (1S,2R,5S,8S,9S,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one —— C11H10O2
(1S,2R,5S,8S,9S,12R)-7-oxatetracyclo[6.4.0.02,12.05,9]dodeca-3,10-dien-6-one
—— (1S,2S,3R,6R,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one —— C11H10O2
(1S,2S,3R,6R,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one
—— (1R,4S,7S,8R)-5-oxatricyclo[5.3.2.04,8]dodeca-2,9,11-trien-6-one —— C11H10O2
(1R,4S,7S,8R)-5-oxatricyclo[5.3.2.04,8]dodeca-2,9,11-trien-6-one
—— (1S,2R,3R,6R,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one —— C11H10O2
(1S,2R,3R,6R,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one
—— (1S,2R,3R,6S,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one —— C11H10O2
(1S,2R,3R,6S,7R,10S)-8-oxatetracyclo[5.5.0.02,6.03,10]dodeca-4,11-dien-9-one
—— (1'S,2'S,3'S,11'S,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione —— C21H26O5
(1'S,2'S,3'S,11'S,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione
—— (1'S,2'S,3'R,11'R,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione —— C21H26O5
(1'S,2'S,3'R,11'R,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione
—— (1'S,2'S,3'S,11'R,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione —— C21H26O5
(1'S,2'S,3'S,11'R,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione
—— (1'S,2'S,3'R,11'S,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione —— C21H26O5
(1'S,2'S,3'R,11'S,13'S)-3'-methyl-13'-prop-2-enylspiro[1,3-dioxolane-2,6'-15-oxatetracyclo[11.2.1.02,11.03,8]hexadec-8-ene]-12',14'-dione
—— (7Z,10R)-7-hydroxyimino-10-methyloxecan-2-one —— C10H17NO3
(7Z,10R)-7-hydroxyimino-10-methyloxecan-2-one
—— (1R,2S,3S,7R,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one —— C12H14O2
(1R,2S,3S,7R,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one
—— (1R,2S,3R,7S,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one —— C12H14O2
(1R,2S,3R,7S,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one
—— (1R,2S,3R,7R,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one —— C12H14O2
(1R,2S,3R,7R,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one
—— (1R,2S,3S,7S,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one —— C12H14O2
(1R,2S,3S,7S,9S,10R)-5-oxatetracyclo[8.2.1.02,9.03,7]tridec-11-en-4-one
—— (4S)-4-chloro-4-[(pentafluoro-lambda6-sulfanyl)methyl]oxetan-2-one —— C4H4ClF5O2S
(4S)-4-chloro-4-[(pentafluoro-lambda6-sulfanyl)methyl]oxetan-2-one
—— (4R)-4-chloro-4-[(pentafluoro-lambda6-sulfanyl)methyl]oxetan-2-one —— C4H4ClF5O2S
(4R)-4-chloro-4-[(pentafluoro-lambda6-sulfanyl)methyl]oxetan-2-one
—— (1S,2R,6S,9S,10S)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehyde —— C15H18O4
(1S,2R,6S,9S,10S)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehyde
—— (1S,2R,6R,9S,10S)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehyde —— C15H18O4
(1S,2R,6R,9S,10S)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehyde
—— (1'S,2'R,5'R,8'R)-10'-oxospiro[1,3-dioxolane-2,4'-9-oxatricyclo[6.2.1.01,5]undecane]-2'-carboxylic acid —— C13H16O6
(1'S,2'R,5'R,8'R)-10'-oxospiro[1,3-dioxolane-2,4'-9-oxatricyclo[6.2.1.01,5]undecane]-2'-carboxylic acid
—— (1'S,2'R,5'S,8'R)-10'-oxospiro[1,3-dioxolane-2,4'-9-oxatricyclo[6.2.1.01,5]undecane]-2'-carboxylic acid —— C13H16O6
(1'S,2'R,5'S,8'R)-10'-oxospiro[1,3-dioxolane-2,4'-9-oxatricyclo[6.2.1.01,5]undecane]-2'-carboxylic acid
—— (3S,4Z,5S)-5-[(1R)-1,2-dihydroxyethyl]-3-hydroxy-4-hydroxyiminooxolan-2-one —— C6H9NO6
(3S,4Z,5S)-5-[(1R)-1,2-dihydroxyethyl]-3-hydroxy-4-hydroxyiminooxolan-2-one
—— (3S,4Z,5S)-5-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-hydroxyiminooxolan-2-one —— C6H9NO6
(3S,4Z,5S)-5-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-hydroxyiminooxolan-2-one
—— (3Z)-3-[[(2R)-oxiran-2-yl]methylidene]oxolan-2-one —— C7H8O3
(3Z)-3-[[(2R)-oxiran-2-yl]methylidene]oxolan-2-one
—— (3Z)-3-[[(2S)-oxiran-2-yl]methylidene]oxolan-2-one —— C7H8O3
(3Z)-3-[[(2S)-oxiran-2-yl]methylidene]oxolan-2-one