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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
—— (6R)-6-[2-(tert-butyldiphenylsilanyloxy)-ethyl]-5,5-dimethyldihydropyran-2,4-dione 1174504-26-7 C25H32O4Si
(6R)-6-[2-(tert-butyldiphenylsilanyloxy)-ethyl]-5,5-dimethyldihydropyran-2,4-dione
—— 4-(chloromethyl)oxetane-2-one —— C4H5ClO2
4-(chloromethyl)oxetane-2-one
—— rac-4-(hydroxymethyl)-4-methyl-3,4,5-trihydrofuran-2-one 1142950-59-1 C6H10O3
rac-4-(hydroxymethyl)-4-methyl-3,4,5-trihydrofuran-2-one
—— Spongialactone A 120030-04-8 C20H26O5
Spongialactone A
—— 5-((t-butyldiphenylsiloxy)methyl)dihydrofuran-2(3H)-one 114142-19-7 C21H26O3Si
5-((t-butyldiphenylsiloxy)methyl)dihydrofuran-2(3H)-one
—— (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-hydroxy-ethyl)-cyclopenta[b]furan-2-one 879880-46-3 C15H28O4Si
(3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-hydroxy-ethyl)-cyclopenta[b]furan-2-one
—— (4R,5S)-5-(2-Hydroxy-ethyl)-4,5-dimethyl-dihydro-furan-2-one 178740-14-2 C8H14O3
(4R,5S)-5-(2-Hydroxy-ethyl)-4,5-dimethyl-dihydro-furan-2-one
—— (4R,5R)-5-(2-Hydroxy-ethyl)-4,5-dimethyl-dihydro-furan-2-one 178627-94-6 C8H14O3
(4R,5R)-5-(2-Hydroxy-ethyl)-4,5-dimethyl-dihydro-furan-2-one
—— 3-hydroxy-3-methyl-4-bromo-7-phenyl-5-heptanolide 69172-22-1 C14H17BrO3
3-hydroxy-3-methyl-4-bromo-7-phenyl-5-heptanolide
—— Naphtho(1,8-bc)pyran-2,9-dione, 3,3a,6,6a,9a,9b-hexahydro-7,9b-dimethyl-, (3aalpha,6abeta,9abeta,9balpha)- 104265-16-9 C14H16O3
Naphtho(1,8-bc)pyran-2,9-dione, 3,3a,6,6a,9a,9b-hexahydro-7,9b-dimethyl-, (3aalpha,6abeta,9abeta,9balpha)-
—— Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-4,7,9b-trimethyl-, (3aalpha,6abeta,9aalpha,9balpha)- 104265-17-0 C15H18O3
Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-4,7,9b-trimethyl-, (3aalpha,6abeta,9aalpha,9balpha)-
—— 4-n-dodecyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-74-7 C22H40O2Si
4-n-dodecyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 4-n-dodecyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-81-6 C28H52O2Si
4-n-dodecyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 4-hydroxy-4,5-dimethyl-dihydro-furan-2-one 110801-55-3 C6H10O3
4-hydroxy-4,5-dimethyl-dihydro-furan-2-one
—— 4-n-dodecyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-82-7 C28H52O2Si
4-n-dodecyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-(methoxymethyl)-, (3aalpha,6abeta,9abeta,9balpha)- 104199-23-7 C15H18O5
Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-(methoxymethyl)-, (3aalpha,6abeta,9abeta,9balpha)-
—— 4-n-dodecyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-73-6 C22H40O2Si
4-n-dodecyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-methyl-, (3aalpha,6abeta,9abeta,9balpha)- 104199-21-5 C14H16O4
Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-methyl-, (3aalpha,6abeta,9abeta,9balpha)-
—— Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-(methoymethyl)-4,7-dimethyl-, (3aalpha,6abeta,9abeta,9balpha)- 104199-05-5 C16H20O4
Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-(methoymethyl)-4,7-dimethyl-, (3aalpha,6abeta,9abeta,9balpha)-
—— Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-(methoxymethyl)-4-methyl-, (3aalpha,6abeta,9abeta,9balpha)- 104199-24-8 C16H20O5
Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-9b-(methoxymethyl)-4-methyl-, (3aalpha,6abeta,9abeta,9balpha)-
—— Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-4,9b-dimethyl-, (3aalpha,6abeta,9abeta,9balpha)- 104199-22-6 C15H18O4
Naphtho(1,8-bc)pyran-2,7-dione, 3,3a,6,6a,9a,9b-hexahydro-9-methoxy-4,9b-dimethyl-, (3aalpha,6abeta,9abeta,9balpha)-
—— methylidene mevalonolactone 886986-69-2 C7H10O3
methylidene mevalonolactone
—— 2-Benzyl-4-hydroxy-4-phenyl-buttersaeurelacton 1804-29-1 C17H16O2
2-Benzyl-4-hydroxy-4-phenyl-buttersaeurelacton
—— (4S. 5R)-4-Amino-5-ethoxy-dihydro-furan-2-one 410079-22-0 C6H11NO3
(4S. 5R)-4-Amino-5-ethoxy-dihydro-furan-2-one
—— spiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-3,1'-cyclopentane]-1-one 145967-34-6 C11H16O2
spiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-3,1'-cyclopentane]-1-one
—— (3aalpha,4alpha,4aalpha,8aalpha,9abeta)-(-)-8a-Ethenyloctahydro-4-hydroxy-3,5-bis(methyl ene)-2H-furo(3,2-g)(2)benzopyran-2,6(3H)-dione 20107-26-0 C15H16O5
(3aalpha,4alpha,4aalpha,8aalpha,9abeta)-(-)-8a-Ethenyloctahydro-4-hydroxy-3,5-bis(methyl ene)-2H-furo(3,2-g)(2)benzopyran-2,6(3H)-dione
—— 4-trimethylsilylmethyl butyrolactone 94319-37-6 C8H16O2Si
4-trimethylsilylmethyl butyrolactone
—— (S)-7-methyloctalactone 126372-24-5 C9H16O2
(S)-7-methyloctalactone
—— 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one 94667-54-6 C25H42O4Si
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one
—— (3aR,4S,5S,6aS)-4-[(t-butyldiphenylsiloxy)methyl]-5-fluorohexahydro-2H-cyclopenta[b]furan-2-one 208114-21-0 C24H29FO3Si
(3aR,4S,5S,6aS)-4-[(t-butyldiphenylsiloxy)methyl]-5-fluorohexahydro-2H-cyclopenta[b]furan-2-one
—— 2-acetyl-(2'-pentyl)-4-methylbutyrolactone 105705-08-6 C12H20O3
2-acetyl-(2'-pentyl)-4-methylbutyrolactone
—— 2-acetil-2-cloro-4-valerolattone 57160-20-0 C7H9ClO3
2-acetil-2-cloro-4-valerolattone
—— (1R,6S,7R,8S)-6-(hydroxymethyl)-6,7-dimethyl-9-oxatricyclo[6.3.1.0<sup>1,5</sup>]dodec-4-ene-3,10-dione 1395878-65-5 C14H18O4
(1R,6S,7R,8S)-6-(hydroxymethyl)-6,7-dimethyl-9-oxatricyclo[6.3.1.0<sup>1,5</sup>]dodec-4-ene-3,10-dione
—— (1R,6S,7R,8S)-6-[(methoxymethoxy)methyl]-6,7-dimethyl-9-oxatricyclo[6.3.1.0<sup>1,5</sup>]dodec-4-ene-3,10-dione 1395878-64-4 C16H22O5
(1R,6S,7R,8S)-6-[(methoxymethoxy)methyl]-6,7-dimethyl-9-oxatricyclo[6.3.1.0<sup>1,5</sup>]dodec-4-ene-3,10-dione
—— (3S,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-3-methyl-dihydro-furan-2-one 215317-62-7 C25H34O3Si
(3S,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-3-methyl-dihydro-furan-2-one
—— 2,2-dimethyl-3-<(2-hydroxy-2-methyl)-1-hydroxyprop-1-yl>-1-cyclopropanecarboxylic acid lactone 91179-56-5 C10H16O3
2,2-dimethyl-3-<(2-hydroxy-2-methyl)-1-hydroxyprop-1-yl>-1-cyclopropanecarboxylic acid lactone
—— (3R,4'S)-(-)-3-Hydroxymethyl-2-(4'-methylhexanoyl)-4-butanolide 122922-48-9 C12H20O4
(3R,4'S)-(-)-3-Hydroxymethyl-2-(4'-methylhexanoyl)-4-butanolide
—— 2,2-dimethyl-3-<(2-β-methoxyethoxymethoxy-2-methyl)-1-hydroxyprop-1-yl>-1-cyclopropanecarboxylic acid lactone 127681-69-0 C14H24O5
2,2-dimethyl-3-<(2-β-methoxyethoxymethoxy-2-methyl)-1-hydroxyprop-1-yl>-1-cyclopropanecarboxylic acid lactone
—— 2,2-dimethyl-3-(1-hydroxy-2-methyl-2-propen-1-yl)-1-cyclopropanecarboxylic acid lactone 127851-86-9 C10H14O2
2,2-dimethyl-3-(1-hydroxy-2-methyl-2-propen-1-yl)-1-cyclopropanecarboxylic acid lactone
—— (2S,3S,4'S,5'R,2'E)-2-(4',5'-epoxyhexen)oyl-2-hydroxy-3-tert-butyldimethylsilyloxymethyl-4-butanolide 797050-27-2 C17H28O6Si
(2S,3S,4'S,5'R,2'E)-2-(4',5'-epoxyhexen)oyl-2-hydroxy-3-tert-butyldimethylsilyloxymethyl-4-butanolide
—— (2R,3S,4'S,5'R,2'E)-2-(4',5'-epoxyhexen)oyl-2-hydroxy-3-tert-butyldimethylsilyloxymethyl-4-butanolide 797050-02-3 C17H28O6Si
(2R,3S,4'S,5'R,2'E)-2-(4',5'-epoxyhexen)oyl-2-hydroxy-3-tert-butyldimethylsilyloxymethyl-4-butanolide
—— (1S,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0<sup>2.6</sup>)-8-decen-3-one 115237-16-6 C10H12O3
(1S,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0<sup>2.6</sup>)-8-decen-3-one
—— (1R,2S,6S,7R,8S)-65-hydroxy-4-oxatricyclo(6.2.1.0<sup>2.7</sup>)-9-undecen-3-one 141985-62-8 C10H12O3
(1R,2S,6S,7R,8S)-65-hydroxy-4-oxatricyclo(6.2.1.0<sup>2.7</sup>)-9-undecen-3-one
—— (2R,5S,6S)-5-methoxymethyl-4-oxa-endo-tricyclo<5.2.1.0<sup>2.6</sup>>dec-8-en-3-one 111533-93-8 C11H14O3
(2R,5S,6S)-5-methoxymethyl-4-oxa-endo-tricyclo<5.2.1.0<sup>2.6</sup>>dec-8-en-3-one
—— (1R,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0<sup>2.6</sup>)-8-decen-3-one 142758-01-8 C10H12O3
(1R,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0<sup>2.6</sup>)-8-decen-3-one
—— 3-but-3-enylspirocyclohexl-1,5'-butyrolactone 142636-41-7 C13H20O2
3-but-3-enylspirocyclohexl-1,5'-butyrolactone
—— (4R,5R)-5-(bromomethyl)-4-hydroxydihydrofuran-2(3H)-one 817623-02-2 C5H7BrO3
(4R,5R)-5-(bromomethyl)-4-hydroxydihydrofuran-2(3H)-one
—— (4S,5R)-5-azidomethyl-4-hydroxydihydrofuran-2-one 1429476-58-3 C5H7N3O3
(4S,5R)-5-azidomethyl-4-hydroxydihydrofuran-2-one
—— 5α-hydroxyaplysistatin 1206799-14-5 C15H21BrO4
5α-hydroxyaplysistatin
—— 6-<(1,3-dioxolan-2-yl)methyl>-3-methyltetrahydropyran-2-one 219779-41-6 C10H16O4
6-<(1,3-dioxolan-2-yl)methyl>-3-methyltetrahydropyran-2-one