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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-Methylene-5,5-dipropyl-dihydro-furan-2-one 77407-52-4 C11H18O2
—— (E)-5-Ethoxy-3-ethylidene-2-oxo-4,5-dihydrofuran 142038-42-4 C8H12O3
—— methyl 17-iodo-13,14,15,16-tetranorlabd-7-en-19,6β-olide-12-oate 291748-37-3 C17H23IO4
—— (3S,4R,5S,6S)-4-Hydroxy-3,5-dimethyl-6-(2-triisopropylsilanyloxy-ethyl)-tetrahydro-pyran-2-one 482626-43-7 C18H36O4Si
—— (2R,3S,4R)-3,4-Dihydroxy-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid ethyl ester 626201-46-5 C20H36O6
—— (3S,5S)-3-methyl-5-((Z)-pent-1-en-3-ynyl)dihydrofuran-2(3H)-one 1613221-20-7 C10H12O2
—— (S)-5-Oxo-tetrahydro-furan-2-carboxylic acid (6-azido-hexyl)-amide 192050-84-3 C11H18N4O3
—— (3S,3aS,4R,6aS)-4-hydroxy-3-vinylhexahydro-1H-cyclopenta[c]furan-1-one 669000-28-6 C9H12O3
—— (1'R,5R)-5-(1'-hydroxypent-4'-ynyl)tetrahydrofuran-2-one 861807-54-7 C9H12O3
—— 2-iodo-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one 681259-97-2 C11H17IO2
—— 5,5-Dimethyl-4-((Z)-3-oxo-but-1-enyl)-dihydro-furan-2-one 107390-78-3 C10H14O3
—— 3-[1-(tert-Butyl-dimethyl-silanyl)-meth-(Z)-ylidene]-4-methyl-oxetan-2-one 128549-44-0 C11H20O2Si
—— (+/-)-6,7-O,O'-pimeloylsynthanecine A 119741-03-6 C14H21NO4
—— 5-methoxy-cyclohexane-1,3-dicarboxylic acid anhydride 64860-09-9 C9H12O4
—— (3S,4S)-4-(2-hydroxyethyl)-3-methyloxolan-2-one 1141365-68-5 C7H12O3
—— 2-ethyl-2-butyl-glutaric acid-anhydride 86351-99-7 C11H18O3
—— 1,11-Bis-(2-oxo-oxetan-3-yl)-4,8-dithia-undecane 412934-67-9 C15H24O4S2
—— (4S,5S)-5-allyl-4-(hydroxymethyl)dihydrofuran-2(3H)-one 1622093-94-0 C8H12O3
—— 6-(tert-Butyl-dimethyl-silanyloxy)-1-oxa-spiro[4.4]nonan-2-one 76643-91-9 C14H26O3Si
—— (2ξ,5α)-2,7',8',10'-tetrahydro-4'H,6'H-17a-oxa-3',4',10',11'-tetraaza-cyclododeca[2,3]-17a-homo-androstane-17,5',9'-trione 16987-68-1 C25H36N4O4
—— (4R,5R)-4-Hydroxy-5-((Z)-oct-2-enyl)-dihydro-furan-2-one 291755-34-5 C12H20O3
—— tert-butyl (R,R)-(3-acetyl-2-oxotetrahydrofuran-3-yl)(phenyl)methylcarbamate 1263506-19-9 C18H23NO5
—— [(1S)-1-[(3S)-2-oxooxolan-3-yl]ethyl] acetate 155321-92-9 C8H12O4
—— 3-(Chloromethyl)-2-oxaspiro[4.5]deca-6,9-dien-1-one 951399-08-9 C10H11ClO2
—— 141602-78-0 C15H18O4
—— ((1<i>S</i>)-2<i>c</i>-carboxy-4<i>c</i>-isopropyl-1,2<i>t</i>-dimethyl-cyclohex-<i>r</i>-yl)-acetic acid-anhydride 93405-58-4 C14H22O3
—— (+/-)-4bβ-Methyl-1β-<2-hydroxyaethyl>-2α-<2-hydroxy-propyl>-7α-hydroxy-4aα,8aβ,10aβ-perhydrophenanthren-2β-carbonsaeurelacton v. F: 218grad 14512-58-4 C21H34O4
—— ((1R,3R,6S,7R,9R)-5-Oxo-4,8-dioxa-tricyclo[4.2.1.0<sup>3,7</sup>]non-9-yl)-acetic acid methyl ester 883-52-3 C10H12O5
—— α,α'-Dimethyl-cyclohexan-diessigsaeure-(1,1)-anhydrid 91765-09-2 C12H18O3
—— (3R,5R)-3-cyclohexyl-dihydro-5-phenylfuran-2(3H)-one 1092798-50-9 C16H20O2
—— 3,3a,4,7,8,8a-Hexahydro-cyclohepta[b]furan-2-one 4431-08-7 C9H12O2
—— (-)-(4S)-4-benzyltetrahydropyran-2-one 71301-86-5 C12H14O2
—— (R)-5-((S)-1-Methoxymethoxy-ethyl)-dihydro-furan-2-one 130258-62-7 C8H14O4
—— (1S,3S,5S)-3-Hydroxy-8,8-dimethyl-2-methylene-6-oxa-bicyclo[3.2.1]octan-7-one 564476-63-7 C10H14O3
—— 4-Hydroxy-1,3,4-trimethyl-cyclohexan-carbonsaeure-(1)-lacton 92015-71-9 C10H16O2
—— Trisnor-gamma-lactone 50340-31-3 C19H30O4
—— (4S,5S)-3-(11-Dodecen-1-yl)-4-hydroxy-5-methyldihydro-2(3H)-furanone (non-preferred name) 486990-25-4 C17H30O3
—— 6-[6-(Trifluoromethyl)pyridin-3-yl]oxan-2-one 1312780-20-3 C11H10F3NO2
—— opt.-inakt. β-Hydroxy-β-methyl-γ-phenyl-δ-valerolacton 91497-02-8 C12H14O3
—— Acetic acid (1R,4R,8R,10S)-4,10-dimethyl-6,9-dioxo-5-oxa-tricyclo[5.3.0.0<sup>4,8</sup>]dec-10-yl ester 77808-79-8 C13H16O5
—— 2-(methoxycarbonyl)-2,3-dimethyl-5-pentanolide 81165-18-6 C9H14O4
—— 7-iodo-9-phenyloxonan-2-one 412027-24-8 C14H17IO2
—— α-<1-Chlorcarbonyl-ethyl>-γ-butyrolacton 3400-96-2 C7H9ClO3
—— 3-(1-methylheptyl)butanolide 78344-52-2 C12H22O2
—— N-((S)-((S)-5-oxotetrahydrofuran-2-yl)(phenyl)methyl)thiophene-2-sulfonamide 1125509-15-0 C15H15NO4S2
—— N-(4,7-dimethyl-1-oxooctahydrocyclopenta[c]pyran-3-yl)-3-methyloxirane-2-carboxamide 2752741-78-7 C14H21NO4
—— 2-(4-Hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-2,4,4-trimethyl-2,3,4,7-tetrahydro-furo[3,4-b]pyran-5-one 104499-45-8 C14H16O6
—— (+/-)-6,7-O,O-(succinyl)synthanecine A 113298-00-3 C11H15NO4
—— 6(R)-[2-[8(S)-(2,2-dimethylbutyryloxy)-2(S)-methyl-6(S)-aminocarbonyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one 114801-44-4 C25H41NO6
—— methyl-2-C-(carboxymethylenemethyl)-2,5-dideoxy-5-C-(n-propyl)-D-lyxofuranoside-2,3-γ-lactone 133519-44-5 C12H18O4