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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
—— D-cymarono-1,4-lactone 100761-16-8 C7H12O4
D-cymarono-1,4-lactone
—— 6-oxa-spiro[2.5]octane-5,7-dione 144728-22-3 C7H8O3
6-oxa-spiro[2.5]octane-5,7-dione
—— 3-tert-butyltetrahydropyran-2-one 59726-49-7 C9H16O2
3-tert-butyltetrahydropyran-2-one
—— trans-3-(ethoxycarbonyl)-2,2,4-trimethyl-4-dodecanolide —— C18H32O4
trans-3-(ethoxycarbonyl)-2,2,4-trimethyl-4-dodecanolide
—— 3,3,4,4-tetramethyldihydrofuran-2(3H)-one 1679-54-5 C8H14O2
3,3,4,4-tetramethyldihydrofuran-2(3H)-one
—— (S)-tert-butyl 2-hydroxy-2-((R)-5-oxotetrahydrofuran-2-yl)-2-phenylacetate 1279018-21-1 C16H20O5
(S)-tert-butyl 2-hydroxy-2-((R)-5-oxotetrahydrofuran-2-yl)-2-phenylacetate
—— 3-Ethoxycarbonyl-4-hydroxy-pentansaeurelacton 98558-93-1 C8H12O4
3-Ethoxycarbonyl-4-hydroxy-pentansaeurelacton
—— 2,2-Dimethylparaconsaeure-ethylester 34566-25-1 C9H14O4
2,2-Dimethylparaconsaeure-ethylester
—— 3,5-Dimethyl-5-pentyl-dihydro-furan-2-one 77756-02-6 C11H20O2
3,5-Dimethyl-5-pentyl-dihydro-furan-2-one
—— Ethyl 2-(2,5-dimethylfuran-3-yl)-2-methyl-5-oxo-4-propan-2-ylideneoxolane-3-carboxylate 1291065-72-9 C17H22O5
Ethyl 2-(2,5-dimethylfuran-3-yl)-2-methyl-5-oxo-4-propan-2-ylideneoxolane-3-carboxylate
—— 4-oxo-6-pentyl-3,4,5,6-tetrahydro-2-pyrone 97986-89-5 C10H16O3
4-oxo-6-pentyl-3,4,5,6-tetrahydro-2-pyrone
—— 5-Hydroxy-3-phenyl-dihydro-furan-2-one 66661-73-2 C10H10O3
5-Hydroxy-3-phenyl-dihydro-furan-2-one
—— 6-ethyl-3-oxabicyclo[3.1.0]hexan-2-one 1208548-49-5 C7H10O2
6-ethyl-3-oxabicyclo[3.1.0]hexan-2-one
—— α-ethyl-α-methyl-γ-dimethyl-γ-butyrolactone 131424-14-1 C9H16O2
α-ethyl-α-methyl-γ-dimethyl-γ-butyrolactone
—— (4R,5R)-5-Carbomethoxy-4,5-dimethyl-2(E)-ethylidene-5-pentanolide 107382-61-6 C11H16O4
(4R,5R)-5-Carbomethoxy-4,5-dimethyl-2(E)-ethylidene-5-pentanolide
—— (+/-)-integerrinecic acid lactone 3055-21-8 C10H14O4
(+/-)-integerrinecic acid lactone
—— 3-nonyl-dihydro-furan-2-one 77761-58-1 C13H24O2
3-nonyl-dihydro-furan-2-one
—— (4R,5R)-4-methyl-5-(methoxycarbonyl)-5-hexanolide 105927-22-8 C9H14O4
(4R,5R)-4-methyl-5-(methoxycarbonyl)-5-hexanolide
—— tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid chloride 59894-56-3 C6H7ClO3
tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid chloride
—— 5-(1,2-dimethyl-2-propenyl)-5-methyldihydro-2(3H)-furanone 77924-64-2 C10H16O2
5-(1,2-dimethyl-2-propenyl)-5-methyldihydro-2(3H)-furanone
—— γ-cyclopentyl-γ-methyl-γ-butyrolactone 2146-24-9 C10H16O2
γ-cyclopentyl-γ-methyl-γ-butyrolactone
—— 5-(dimethoxymethyl)dihydrofuran-2(3H)-one 168689-38-1 C7H12O4
5-(dimethoxymethyl)dihydrofuran-2(3H)-one
—— (S)-tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid chloride 86363-00-0 C6H7ClO3
(S)-tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid chloride
—— (R)-5-methyl-5-(4-methyl-2-oxopent-3-enyl)dihydrofuran-2(3H)-one 1392512-72-9 C11H16O3
(R)-5-methyl-5-(4-methyl-2-oxopent-3-enyl)dihydrofuran-2(3H)-one
—— (-)-(R)-5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one 127718-14-3 C7H12O3
(-)-(R)-5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one
—— 4-propargyl-4-valerolactone 94083-23-5 C8H10O2
4-propargyl-4-valerolactone
—— ethyl (2R,3S)-3-(methoxy(methyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate 1233923-19-7 C10H15NO6
ethyl (2R,3S)-3-(methoxy(methyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate
—— (4R,6S)-6-tert-butyl-4-hydroxyoxan-2-one 132895-30-8 C9H16O3
(4R,6S)-6-tert-butyl-4-hydroxyoxan-2-one
—— (R)-[3-(1-methyl)ethyl]-dihydrofuran-2(3H)-one 80410-23-7 C7H12O2
(R)-[3-(1-methyl)ethyl]-dihydrofuran-2(3H)-one
—— (R)-5-Hexyl-dihydro-furan-2-one 107797-26-2 C10H18O2
(R)-5-Hexyl-dihydro-furan-2-one
—— meso-2,4-dimethylglutaric anhydride 7446-84-6 C7H10O3
meso-2,4-dimethylglutaric anhydride
—— 4-acetyl-3-butyl-5-methyl-dihydro-furan-2-one 197303-75-6 C11H18O3
4-acetyl-3-butyl-5-methyl-dihydro-furan-2-one
—— 3-butylidene-5-methyl-4-vinyl-dihydro-furan-2-one 850166-32-4 C11H16O2
3-butylidene-5-methyl-4-vinyl-dihydro-furan-2-one
—— 3-butyl-5-methyl-4-vinyl-dihydro-furan-2-one 850166-33-5 C11H18O2
3-butyl-5-methyl-4-vinyl-dihydro-furan-2-one
—— 2-oxaspiro<4.5>dec-7-en-3-one 133568-33-9 C9H12O2
2-oxaspiro<4.5>dec-7-en-3-one
—— 5-methyl-4-phenyldihydrofuran-2(3H)-one 23725-23-7 C11H12O2
5-methyl-4-phenyldihydrofuran-2(3H)-one
—— 4-(2-hydroxycyclopentyl)oxacyclopentan-2-one 938465-33-9 C9H14O3
4-(2-hydroxycyclopentyl)oxacyclopentan-2-one
—— rac-(1R,2S,6R,7S)-4-oxa-3-oxotricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-5-ol 56232-16-7 C9H10O3
rac-(1R,2S,6R,7S)-4-oxa-3-oxotricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-5-ol
—— 4,5-Dipentyl-dihydro-furan-2-one 79263-56-2 C14H26O2
4,5-Dipentyl-dihydro-furan-2-one
—— 9-Methyl-4-oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-3-on-5-ol 56232-17-8 C10H12O3
9-Methyl-4-oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-3-on-5-ol
—— (-)-(1S)-camphanic chloride 39637-74-6 C10H13ClO3
(-)-(1S)-camphanic chloride
—— 3-hydroxy-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran-1-one 56232-16-7 C9H10O3
3-hydroxy-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran-1-one
—— 3-[(2-Methylphenyl)methyl]oxepan-2-one 133880-78-1 C14H18O2
3-[(2-Methylphenyl)methyl]oxepan-2-one
—— 2-<i>tert</i>-butyl-4-hydroxy-acetoacetic acid-lactone 5457-00-1 C8H12O3
2-<i>tert</i>-butyl-4-hydroxy-acetoacetic acid-lactone
—— cis-3,4-dimethyl-2-propiolactone —— C5H8O2
cis-3,4-dimethyl-2-propiolactone
—— (4R,6R)-4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]tetrahydropyran-2-one 445473-82-5 C18H34O3S2Si
(4R,6R)-4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]tetrahydropyran-2-one
—— 4-allyldihydrofuran-2(3H)-one 56596-18-0 C7H10O2
4-allyldihydrofuran-2(3H)-one
—— (3S,4R)-4-[(E,2R,3S,4R,5S)-2-(tert-butyldimethylsilanyloxy)-4-methoxy-3,5-dimethylnon-7-enyl]-3-ethyloxetan-2-one 900171-45-1 C23H44O4Si
(3S,4R)-4-[(E,2R,3S,4R,5S)-2-(tert-butyldimethylsilanyloxy)-4-methoxy-3,5-dimethylnon-7-enyl]-3-ethyloxetan-2-one
—— 5-isopropyl-5-phenyl-γ-butyrolactone 134391-15-4 C13H16O2
5-isopropyl-5-phenyl-γ-butyrolactone
—— 2-isopropylglutaric anhydride 57280-77-0 C8H12O3
2-isopropylglutaric anhydride