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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
—— 5-methyl-3-(14-methylhexadecoxy)-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one —— C24H43O6P
5-methyl-3-(14-methylhexadecoxy)-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one
—— Methyl 2-[8-(furan-3-yl)-1,3,15-trihydroxy-7,16,18-trimethyl-10-oxo-9,13-dioxahexacyclo[14.2.1.02,14.03,12.04,18.07,12]nonadecan-17-yl]acetate —— C27H34O9
Methyl 2-[8-(furan-3-yl)-1,3,15-trihydroxy-7,16,18-trimethyl-10-oxo-9,13-dioxahexacyclo[14.2.1.02,14.03,12.04,18.07,12]nonadecan-17-yl]acetate
—— 8-Hydroxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.01,3.04,8]tridec-9-en-13-one —— C15H20O3
8-Hydroxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.01,3.04,8]tridec-9-en-13-one
—— 11-Hydroxy-3,8-dimethyl-5,9,15-trioxatetracyclo[11.2.1.02,6.08,10]hexadecane-4,14-dione —— C15H20O6
11-Hydroxy-3,8-dimethyl-5,9,15-trioxatetracyclo[11.2.1.02,6.08,10]hexadecane-4,14-dione
—— 3,7,11,11,14-Pentamethyl-12-oxatetracyclo[7.6.0.01,6.010,14]pentadecane-2,13,15-trione —— C19H26O4
3,7,11,11,14-Pentamethyl-12-oxatetracyclo[7.6.0.01,6.010,14]pentadecane-2,13,15-trione
—— 5-Hydroperoxy-8-hydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one —— C15H20O5
5-Hydroperoxy-8-hydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one
—— 14-Hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.03,7]tetradecane-5,12-dione —— C15H20O5
14-Hydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.03,7]tetradecane-5,12-dione
—— 9-hydroxy-9-[2-(2-methoxy-5-oxo-2H-furan-4-yl)ethyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecane-3,5-dione —— C21H28O7
9-hydroxy-9-[2-(2-methoxy-5-oxo-2H-furan-4-yl)ethyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecane-3,5-dione
—— 11,12-Dihydroxy-3,8-dimethyl-5,9,15-trioxatetracyclo[11.2.1.02,6.08,10]hexadec-13(16)-ene-4,14-dione —— C15H18O7
11,12-Dihydroxy-3,8-dimethyl-5,9,15-trioxatetracyclo[11.2.1.02,6.08,10]hexadec-13(16)-ene-4,14-dione
—— 4-[1-(2-Ethenyl-4,4-dimethylcyclopentylidene)-2-hydroxyethyl]oxolan-2-one —— C15H22O3
4-[1-(2-Ethenyl-4,4-dimethylcyclopentylidene)-2-hydroxyethyl]oxolan-2-one
—— (9-Hydroxy-3,9-dimethyl-2-oxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-6-yl)methyl acetate —— C17H22O5
(9-Hydroxy-3,9-dimethyl-2-oxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-6-yl)methyl acetate
—— 13-(Furan-3-yl)-8-hydroxy-6,6,10-trimethyl-2,14-dioxatricyclo[9.4.0.01,3]pentadecane-7,15-dione —— C20H26O6
13-(Furan-3-yl)-8-hydroxy-6,6,10-trimethyl-2,14-dioxatricyclo[9.4.0.01,3]pentadecane-7,15-dione
—— (5-Cyano-6-oxooxan-3-yl) prop-2-enoate —— C9H9NO4
(5-Cyano-6-oxooxan-3-yl) prop-2-enoate
—— 7,8,9-Trihydroxy-3-methyl-4,11-dioxabicyclo[8.1.0]undecan-5-one —— C10H16O6
7,8,9-Trihydroxy-3-methyl-4,11-dioxabicyclo[8.1.0]undecan-5-one
—— 3,6-dimethyl-6-(3-methyl-5-oxo-2H-furan-2-yl)-3a,4,5,6a-tetrahydro-3H-cyclopenta[b]furan-2-one —— C14H18O4
3,6-dimethyl-6-(3-methyl-5-oxo-2H-furan-2-yl)-3a,4,5,6a-tetrahydro-3H-cyclopenta[b]furan-2-one
—— 7,8,11-Trihydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one —— C15H22O6
7,8,11-Trihydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one
—— 2,7,8,11-Tetrahydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one —— C15H22O7
2,7,8,11-Tetrahydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one
—— 8-Chloro-12-hydroxy-5-(4-hydroxy-3-methylpent-1-enyl)-10,13,14-trimethyl-4,11,15-trioxatetracyclo[8.7.0.02,7.012,17]heptadeca-2,5,7-triene-9,16-dione —— C23H27ClO7
8-Chloro-12-hydroxy-5-(4-hydroxy-3-methylpent-1-enyl)-10,13,14-trimethyl-4,11,15-trioxatetracyclo[8.7.0.02,7.012,17]heptadeca-2,5,7-triene-9,16-dione
—— (8-hydroxy-3,9-dimethylidene-2-oxo-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl)methyl propanoate —— C18H22O5
(8-hydroxy-3,9-dimethylidene-2-oxo-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl)methyl propanoate
—— (13-Hydroxy-3,8-dimethyl-12-methylidene-4,11-dioxo-10-oxatricyclo[7.3.1.03,7]tridec-5-en-2-yl) 2-methylbut-2-enoate —— C20H24O6
(13-Hydroxy-3,8-dimethyl-12-methylidene-4,11-dioxo-10-oxatricyclo[7.3.1.03,7]tridec-5-en-2-yl) 2-methylbut-2-enoate
—— 7-Methyl-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one —— C13H14O2
7-Methyl-4-phenyl-2-oxabicyclo[2.2.1]heptan-3-one
—— (8-hydroxy-5,8-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,9a-hexahydro-3aH-azuleno[6,5-b]furan-6-yl) acetate —— C17H22O5
(8-hydroxy-5,8-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,9a-hexahydro-3aH-azuleno[6,5-b]furan-6-yl) acetate
—— 5-Deca-1,3,6,8-tetraen-5-yl-3-hydroxyoxolan-2-one —— C14H18O3
5-Deca-1,3,6,8-tetraen-5-yl-3-hydroxyoxolan-2-one
—— 3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone —— C9H16O3
3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
—— 4-[2-(3,3-Dimethyloxiran-2-yl)ethylidene]-9-hydroxy-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydrocyclonona[c]pyran-1-one —— C20H28O4
4-[2-(3,3-Dimethyloxiran-2-yl)ethylidene]-9-hydroxy-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydrocyclonona[c]pyran-1-one
—— [2-[3-(Furan-3-yl)propyl]-2-hydroxy-7-methyl-8-oxospiro[9-oxatricyclo[5.3.3.01,6]tridecane-3,2'-oxirane]-5-yl] acetate —— C23H30O7
[2-[3-(Furan-3-yl)propyl]-2-hydroxy-7-methyl-8-oxospiro[9-oxatricyclo[5.3.3.01,6]tridecane-3,2'-oxirane]-5-yl] acetate
—— (17-Hydroxy-6-methylidene-5-oxo-4,14,16-trioxatetracyclo[8.4.3.01,13.03,7]heptadec-9-en-8-yl) 2-methylpropanoate —— C19H24O7
(17-Hydroxy-6-methylidene-5-oxo-4,14,16-trioxatetracyclo[8.4.3.01,13.03,7]heptadec-9-en-8-yl) 2-methylpropanoate
—— 9-Hydroxy-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one —— C15H20O3
9-Hydroxy-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
—— N-[2-(cyclohex-1-en-1-yl)ethyl]-2,2-dimethyl-5-oxotetrahydrofuran-3-carboxamide —— C15H23NO3
N-[2-(cyclohex-1-en-1-yl)ethyl]-2,2-dimethyl-5-oxotetrahydrofuran-3-carboxamide
—— 5'-(Furan-3-yl)-3,6,7-trimethylspiro[9-oxatricyclo[5.2.2.01,6]undecane-2,3'-oxolane]-2',8-dione —— C20H24O5
5'-(Furan-3-yl)-3,6,7-trimethylspiro[9-oxatricyclo[5.2.2.01,6]undecane-2,3'-oxolane]-2',8-dione
—— [17-Hydroxy-13-(methoxymethyl)-8,12-dimethyl-2,7,15,19-tetraoxo-14-oxa-18-azapentacyclo[10.7.0.01,16.03,11.04,8]nonadec-3(11)-en-10-yl] 2-methylbutanoate —— C26H33NO9
[17-Hydroxy-13-(methoxymethyl)-8,12-dimethyl-2,7,15,19-tetraoxo-14-oxa-18-azapentacyclo[10.7.0.01,16.03,11.04,8]nonadec-3(11)-en-10-yl] 2-methylbutanoate
—— 2,8-Dihydroxy-2,3,7,11-tetramethyl-5,12-dioxatetracyclo[6.6.0.01,11.03,7]tetradecane-4,13-dione —— C16H22O6
2,8-Dihydroxy-2,3,7,11-tetramethyl-5,12-dioxatetracyclo[6.6.0.01,11.03,7]tetradecane-4,13-dione
—— 8-[2-[Tert-butyl(diphenyl)silyl]oxyhentriacontyl]-9-oxa-1,5-dithiaspiro[5.5]undecan-10-one —— C55H92O3S2Si
8-[2-[Tert-butyl(diphenyl)silyl]oxyhentriacontyl]-9-oxa-1,5-dithiaspiro[5.5]undecan-10-one
—— 5-(furan-3-yl)-4'-hydroxy-6'-methyl-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-ene-2,2'-dione —— C19H20O6
5-(furan-3-yl)-4'-hydroxy-6'-methyl-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-ene-2,2'-dione
—— Methyl 3,12-dimethyl-13-oxo-4,14-dioxatricyclo[9.3.0.03,5]tetradec-8-ene-8-carboxylate —— C16H22O5
Methyl 3,12-dimethyl-13-oxo-4,14-dioxatricyclo[9.3.0.03,5]tetradec-8-ene-8-carboxylate
—— 2,4-dimethyl-5-oxotetrahydrofuran-3-carboxylic acid —— C7H10O4
2,4-dimethyl-5-oxotetrahydrofuran-3-carboxylic acid
—— 15-Hydroxy-15-(hydroxymethyl)-5,5,10-trimethyl-6-oxatetracyclo[12.2.1.01,11.04,10]heptadecan-7-one —— C20H32O4
15-Hydroxy-15-(hydroxymethyl)-5,5,10-trimethyl-6-oxatetracyclo[12.2.1.01,11.04,10]heptadecan-7-one
—— 4-Methyl-5-oct-2-enyloxolan-2-one —— C13H22O2
4-Methyl-5-oct-2-enyloxolan-2-one
—— 1,1'-(Piperazine-1,4-diyldicarbonyl)bis(4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one) —— C24H34N2O6
1,1'-(Piperazine-1,4-diyldicarbonyl)bis(4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one)
—— 2-hydroxy-12-(2-hydroxypropan-2-yl)-7-methylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one —— C15H20O6
2-hydroxy-12-(2-hydroxypropan-2-yl)-7-methylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
—— (3R,3aR,4aS,5R,9aS)-3,5,8-Trimethyl-3a,4,4a,5,6,7,9,9a-octahydroazuleno[6,5-b]furan-2(3H)-one —— C15H22O2
(3R,3aR,4aS,5R,9aS)-3,5,8-Trimethyl-3a,4,4a,5,6,7,9,9a-octahydroazuleno[6,5-b]furan-2(3H)-one
—— 16-Amino-6,13-dimethyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-8-one —— C21H31NO2
16-Amino-6,13-dimethyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-8-one
—— [2-(6,9-Dihydroxy-11-methyl-13-oxo-8,14-dioxatetracyclo[7.6.0.01,6.02,12]pentadecan-12-yl)-1-(furan-3-yl)ethyl] acetate —— C22H28O8
[2-(6,9-Dihydroxy-11-methyl-13-oxo-8,14-dioxatetracyclo[7.6.0.01,6.02,12]pentadecan-12-yl)-1-(furan-3-yl)ethyl] acetate
—— 9-[2-(Furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.04,12]dodec-4-en-3-one —— C20H26O3
9-[2-(Furan-3-yl)ethyl]-9,10,12-trimethyl-2-oxatricyclo[6.3.1.04,12]dodec-4-en-3-one
—— (3a<i>R</i>)-2<i>t</i>,9<i>anti</i>-dihydroxy-3<i>t</i>,8a-dimethyl-6-methylene-(7a<i>t</i>,8a<i>t</i>,8b<i>c</i>)-octahydro-3a<i>r</i>,7<i>c</i>-methano-cyclopenta[<i>b</i>]cyclopropa[<i>d</i>]oxocin-5-one 14026-80-3 C15H20O4
(3a<i>R</i>)-2<i>t</i>,9<i>anti</i>-dihydroxy-3<i>t</i>,8a-dimethyl-6-methylene-(7a<i>t</i>,8a<i>t</i>,8b<i>c</i>)-octahydro-3a<i>r</i>,7<i>c</i>-methano-cyclopenta[<i>b</i>]cyclopropa[<i>d</i>]oxocin-5-one
—— 3-[2-(3-hydroxy-5,5,8a-trimethyl-2-methylidene-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl)ethylidene]oxolan-2-one —— C20H28O4
3-[2-(3-hydroxy-5,5,8a-trimethyl-2-methylidene-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl)ethylidene]oxolan-2-one
—— Karahana lactone 28449-87-8 C10H14O2
Karahana lactone
—— 5-Ethyl-4-hydroxy-3-[(1-pent-1-enylcyclononyl)methylidene]oxolan-2-one —— C21H34O3
5-Ethyl-4-hydroxy-3-[(1-pent-1-enylcyclononyl)methylidene]oxolan-2-one
—— 2,7,8,13-Tetrahydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one —— C15H22O7
2,7,8,13-Tetrahydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one
—— (+/-)-dihydromahubanolide —— C21H38O3
(+/-)-dihydromahubanolide