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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
—— 3,3,6,7-tetramethyl-1-oxo-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylic acid 107821-51-2 C14H20O4
—— (3R,5S,6S)-6-{(2R,4S,5R)-5-[(1S,4S)-4-((S)-5-Bromomethyl-2,5-dimethyl-tetrahydro-furan-2-yl)-1-ethyl-1,4-dihydroxy-butyl]-4-methyl-tetrahydro-furan-2-yl}-3,5-dimethyl-tetrahydro-pyran-2-one 73992-28-6 C25H43BrO6
—— (S)-5-(bromo(cyclohexylidene)methyl)dihydrofuran-2(3H)-one 1628563-41-6 C11H15BrO2
—— 2,2-Dimethyl-butyric acid (1S,4aS,7S,8S,8aS)-8-[2-((2R,4R)-4-benzyloxymethoxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-3-oxo-decahydro-naphthalen-1-yl ester 138660-67-0 C32H46O7
—— (S)-5-t-Butyldimethylsiloxymethyl-4,5-dihydro-5-methylfuran-2(3H)-one 136055-42-0 C12H24O3Si
—— (4S,5S,6S)-6-ethyl-5-methyl-4-prop-2-enyl-4-trimethylsilyloxyoxan-2-one 1612781-67-5 C14H26O3Si
—— 19->6α-Lacton der 6α.7β.16-Trihydroxy-18-nor-kauransaeure-(19) 100175-01-7 C19H28O4
—— (Z,3S,4S,9R,10R)-3,4,7,8,9,10-hexahydro-4,9-bis(methoxymethoxy)-3-methyl-10-pentyloxecin-2-one 1585969-10-3 C19H34O6
—— Pd(cyclobutane-1,1-dicarboxylate-O,O')(NH3)2 122681-80-5 C6H12N2O4Pd
—— diethyl (4a,8aR,E)-8a-methyl-5-(iodomethylene)-2-oxooctahydro-7H-chromene-7,7-dicarboxylate 1233027-57-0 C17H23IO6
—— 7-t-Butyldimethylsilyloxy-4,4-dimethyl-3-oxatricyclo<4.2.0.0<sup>1,5</sup>>octan-2-one 129930-66-1 C15H26O3Si
—— cis-3-Hydroxy-cis-4-aethoxy-cyclohexan-carbonsaeure-lacton 90612-24-1 C9H14O3
—— (3S,5S)-3-methyl-5-vinyldihydrofuran-2(3H)-one 504412-39-9 C7H10O2
—— (3aS,6aR)-5-(5,5-Dimethyl-[1,3]dioxan-2-ylidene)-3a-methyl-hexahydro-cyclopenta[c]furan-1-one 122968-11-0 C14H20O4
—— (E,6R)-6-[(4S,5R,6S)-6-[(1Z,3Z,5S,6S,7E,9E)-11-[(2S,3S,4S)-2-ethyl-4-hydroxy-3-methyl-6-oxooxan-4-yl]-6-hydroxy-5,7-dimethylundeca-1,3,7,9-tetraenyl]-2,2,5-trimethyl-1,3-dioxan-4-yl]-5-methylhept-4-enoic acid 1612781-77-7 C36H56O8
—— (3aS,4S,6aS)-3-Hydroxy-3-hydroxymethyl-4-octyl-furo<3,4-b>furandion-(2,6) 97439-06-0 C15H24O6
—— (3aR,7aR)-4,4-dimethyltetrahydroisobenzofuran-1,5(3H,4H)-dione 1579293-72-3 C10H14O3
—— (Z)-α-(1-chloro-3-phenylpropylidene)-β-(i-propyl)-β-lactone 627526-88-9 C15H17ClO2
—— (S,Z)-6-(hex-1-en-1-yl)tetrahydro-2H-pyran-2-one 1569091-92-4 C11H18O2
—— (3R,4S,5R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(1-hydroxy-1-methyl-ethyl)-4-methyl-dihydro-furan-2-one 155224-29-6 C16H32O4Si
—— (4R,5R)-4-methyl-5-[(2R,5S,6S)-5-methyl-6-[(2S,3S,6R)-3-methyl-6-[(2R,3R)-3-methyl-5-oxooxolan-2-yl]oxan-2-yl]oxan-2-yl]oxolan-2-one 140465-06-1 C22H34O6
—— (4R,6S)-(E)-4-hydroxy-6-<2-(1,2,3,4-tetrahydro-1-naphthylidene)ethyl>-3,4,5,6-tetrahydro-2H-pyran-2-one 137847-59-7 C17H20O3
—— 14-adamantaneacetyl andrographolide 1239575-72-4 C32H46O6
—— 5-(Hydroxymethyl)oxolan-3-one 58534-89-7 C5H8O3
—— (1S<sup>*</sup>,5S<sup>*</sup>,8S<sup>*</sup>)-1-acetonyl-8-formylmethyl-6-oxabicyclo<3.2.1>octan-7-one 81309-72-0 C12H16O4
—— 1β-hydroxy-6β-methyl-1,2,3,4,4aα,5,6,8aα-octahydronaphthalene-5β-carboxylic acid δ-lactone 78669-31-5 C12H16O2
—— 8β-Phenylethyl-4a,5,6,7-tetrahydrochroman-5,6-dicarbonsaeureanhydrid 59792-20-0 C19H20O4
—— 4-chloroacetyl-5,5-dimethyl-dihydro-furan-2-one 90003-24-0 C8H11ClO3
—— 4(R),5(S),8(S)-4-acetoxy-8-[(E),1(R),2(R),6(S)-6-(tert-butyldimethylsilyloxy)-2-hydroxy-1,3,7-trimethyl-oct-3-enyl]-5-methyl-oxocan-2-one 676251-98-2 C27H50O6Si
—— (2<i>R</i>,6'a<i>R</i>)-3',6'a,8'-<i>t</i>-trimethyl-(6'a<i>r</i>)-octahydro-spiro[furan-2,7'-(3<i>t</i>,9a<i>t</i>-methano-cyclopent[<i>b</i>]oxocin)]-5,2',10'-trione 107457-26-1 C17H22O5
—— (3S,3aR,4R,6aS)-5,6a-Dimethyl-2-oxo-4-phenyl-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-3-carboxylic acid 143468-57-9 C16H16O4
—— (+/-)-4a-hydroxy-1<i>t</i>-methyl-(4a<i>r</i>,8a<i>t</i>)-decahydro-naphthalene-1<i>c</i>,2<i>t</i>-dicarboxylic acid-1-lactone-2-methyl ester 107821-19-2 C14H20O4
—— (3aR,9aS,9bR)-9b-Chloromethyl-3a,4,6,7,8,9,9a,9b-octahydro-1H-naphtho[1,2-c]furan-3-one 77912-52-8 C13H17ClO2
—— 5-(2-Methylsulfanyl-ethyl)-dihydro-furan-2-one 6725-61-7 C7H12O2S
—— [Cr(III)(1,4,7-triazacyclononane-N,N',N''-triacetate)] 65532-07-2 C12H18CrN3O6
—— (1R,4S,7S,8R)-1-Methyl-3-oxa-tricyclo[5.2.1.0<sup>4,8</sup>]decan-2-one 85757-85-3 C10H14O2
—— (3<i>RS</i>,4<i>RS</i>)-4-chloro-3-hydroxy-3-methyl-valeric acid-lactone 118660-64-3 C6H9ClO2
—— (S)-5-((S)-2-hydroxy-6-methylhept-5-en-2-yl)-dihydrofuran-2(3H)-one 1242242-19-8 C12H20O3
—— (1R,8S,9R,10S)-9,10-diphenyl-3,6-dioxabicyclo[6.2.0]decane-2,7-dione 90455-59-7 C20H18O4
—— 3-(2-phenylacetyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 1371586-08-1 C13H14O3
—— (5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(phenylselanyl)dihydrofuran-2(3H)-one 106731-86-6 C27H30O3SeSi
—— Latifolic acid 92350-64-6 C7H10O5
—— 3-Chloromethyl-4,5-dipropyl-dihydro-furan-2-one 97191-06-5 C11H19ClO2
—— 71358-21-9 C21H38O3
—— 5-Acetyl-6-benzyl-tetrahydro-pyran-2-one 59958-96-2 C14H16O3
—— (5S)-5-<(2S)-3-<(tert-butyldiphenylsilyl)oxy>-2-hydroixypropyl>-4,5-dihydro-2(3H)-furanone 102717-33-9 C23H30O4Si
—— 4-oxa-5-(N-propylcarbamoyloxy)-tricyclo[5,2,1,02,6 ]dec-8-en-3-one 56232-44-1 C13H17NO4
—— 5-Oxatricyclo<5.2.1.0<sup>2,6</sup>>dec-8-en-3-on 64550-47-6 C9H10O2
—— 5-(1-iodoethyl)-dihydrofuran-2-one 914090-59-8 C6H9IO2
—— (R)-5-(4-Methyl-pentyl)-dihydro-furan-2-one 22908-68-5 C10H18O2