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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
—— 4-ethyl-8-oxaspiro[4.5]decane-7,9-dione 219661-20-8 C11H16O3
—— Acetic acid (S)-2-acetoxy-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester 136345-73-8 C10H14O6
—— 5-(4-((tert-butyldiphenylsilyl)oxy)butyl)dihydrofuran-2(3H)-one 1396570-68-5 C24H32O3Si
—— (4aS,7S,7aS)-hexahydro-7-isopropyl-4a-methylcyclopenta<b>pyran-2(3H)-one 132072-22-1 C12H20O2
—— (3S,4R)-4-methyl-3-[(E,2R)-5-methylhex-3-en-2-yl]oxolan-2-one 115115-38-3 C12H20O2
—— ent-10β,13,15α-trihydroxy-20-norgibberella-1,16-diene-7,19-dioic acid 19,10-lactone 105593-23-5 C19H26O6
—— 6-endo-hydroxy-3-exo-nitro-5-exo-methoxymethyloxy-7-oxabicyclo<2.2.1>heptane-2-endo-carboxylic acid γ-lactone 75467-05-9 C9H11NO7
—— (3a<i>R</i>,9a<i>S</i>)-5b-methyl-3,8-dioxo-(3a<i>r</i>,5a<i>t</i>,5b<i>c</i>,8a<i>c</i>)-octahydro-pentaleno[1,2-<i>c</i>;3a,4-<i>c'</i>]difuran-1<i>t</i>-carboxylic acid methyl ester 29259-63-0 C15H18O6
—— 2-acetyl-3-(2',2'-dichlorovinyl)-4-ethyl-γ-valerolactone 70973-47-6 C11H14Cl2O3
—— (+/-)-4-Hydroxy-3,3-dimethyl-hept-5ξ-ensaeure-lacton 90611-77-1 C9H14O2
—— (4R,4aR,7aR)-4,7a-Dimethyl-7-methylene-hexahydro-cyclopenta[c]pyran-3-one 104084-96-0 C11H16O2
—— sarcocrassocolide A 1224926-67-3 C22H30O6
—— hexahydro-7a-hydroxy-3,3a,6-trimethyl-2(3H)-benzofuranone 96965-83-2 C11H18O3
—— (4arH)-1-Oxo-3,3,5,5,8at-pentamethyl-3,4,4a,5,6,7,8,8a-octahydro-1H-2-benzopyran 92370-86-0 C14H24O2
—— trans,trans-(5S)-5-<9'-(2'',3''-dihydroxycyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone 114489-16-6 C20H32O4
—— 15α-hydroxygibberellin A<sub>20</sub> 7,15-lactone 139113-43-2 C19H22O5
—— D-Glucuronolacton-hexanoylhydrazon 100977-47-7 C22H40N2O6
—— opt.inakt. 2-Methyl-2-ethoxycarbonyl-4-ethoxy-4-hydroxy-buttersaeurelacton 86266-61-7 C10H16O5
—— (3R,4R)-3-<(tert-Butyldimethylsilyl)oxy>-4-(iodomethyl)-γ-butyrolactone 159685-37-7 C11H21IO3Si
—— 3-(3-cyclopentyl-2-methyl-2-(triethylsilylperoxy)propyl)-3-methyldihydrofuran-2(3H)-one 1321200-02-5 C20H38O4Si
—— (1R,4R,5R)-1,4-dihydroxy-3-(2-phenylethyl)cyclohex-2-en-1,5-carbolactone 1259025-90-5 C15H16O4
—— 105044-64-2 C32H52O4
—— α-Formyl-γ-carbethoxy-butyrolacton 108487-86-1 C8H10O5
—— (5R)-5-formyl-5-tetradecanolide 130251-61-5 C15H26O3
—— 4-(2-oxo-propyl)-octahydro-cyclohepta[<i>b</i>]furan-2-one 59456-41-6 C12H18O3
—— Brom-methoxy-α-tetrahydroplumericin 97500-20-4 C16H21BrO7
—— 1,9-Bis-(2-oxo-oxetan-3-yl)-3,7-dithia-nonane 412934-56-6 C13H20O4S2
—— (R)-β,β-dimethyl-δ-(2-furyl)-δ-valerolactone 1429482-71-2 C11H14O3
—— 2-((3S,3aS,6R,7R,7aS)-6-Ethyl-3,6-dimethyl-2-oxo-2,3,3a,6,7,7a-hexahydro-benzofuran-7-yl)-acrylic acid methyl ester 220305-63-5 C16H22O4
—— 5-carbethoxyhexahydrophthalide 96259-70-0 C11H16O4
—— 3-Chloro-4-(γ-N-chloroacetyl-N-methylaminopropyl)-5,6-dihydro-2H-naphtho<1,2-b>pyran-2-one 91098-23-6 C19H21Cl2NO3
—— 6-methyl-3,4,4a,5-tetrahydroisochromen-1-one 1259057-14-1 C10H12O2
—— 1-iodomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one 147905-87-1 C9H13IO2
—— 2-allylglutaric anhydride 415916-55-1 C8H10O3
—— (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylsulfanylmethoxy-dihydro-furan-2-one 549505-10-4 C13H26O4SSi
—— (3S,4S,6R)-3-allyl-4-hydroxy-3-methyl-6-phenyltetrahydro-2H-pyran-2-one 1209462-48-5 C15H18O3
—— picrodendrin G 135463-00-2 C21H28O10
—— α-Methoxymethyl-γ-chlor-δ-hydroxy-γ-valerolacton 18451-83-7 C7H11ClO4
—— (S)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-8-oxa-1,4-dithia-spiro[4.5]decan-7-one 96501-89-2 C24H30O3S2Si
—— 6,6-bis-methylsulfanyl-6-deoxy-L-galactonic acid-4-lactone 118759-71-0 C8H14O5S2
—— 5-[1-Phenyl-meth-(E)-ylidene]-3-(3-phenyl-prop-2-ynyl)-dihydro-furan-2-one 77670-55-4 C20H16O2
—— Pyrethroidinin 96627-14-4 C15H20O4
—— 5-acetyl-3-phenylsulfanyl-3-prop-2-enyloxan-2-one 89665-23-6 C16H18O3S
—— Acetic acid (3R,3aS,5aS,8S,9S,9aS,9bR)-3-isocyanato-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-8-yl ester 74493-55-3 C18H25NO5
—— (5R)-2-methylene-5-tert-butyldimethylsilyloxymethyl-5-tetradecanolide 130322-96-2 C22H42O3Si
—— (1α,2β,4β,5α,6α)-5-hydroxy-3,7-dioxatricyclo<4.2.1.0<sup>2,4</sup>>nonan-8-one 83693-70-3 C7H8O4
—— (3aα,4α,4aβ,5β,7aα,8α,9aα)-3a,4,4a,5,7a,8,9,9a-octahydro-3-(hydroxymethyl)-4a,8-dimethyl-4,5-bis<(tetrahydro-2H-pyran-2-yl)oxy>azuleno<6,5-b>furan-2(3H)-one 82010-21-7 C25H38O7
—— 4-geranyl-tetrahydro-2-furanone 141406-26-0 C12H20O2
—— (+)-(1S,2S,5R,6S,7S,10R)-8-ethylenedithio-6,10-dimethyl-5-pivaloyloxymethyl-4-oxatricyclo<5.3.0.0<sup>2,6</sup>>decan-3-one 162086-77-3 C19H28O4S2
—— (3S,5S)-5-((1S)-1-(N-Boc-amino)-3-methylbutyl)-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one 105018-88-0 C18H31NO4