(4S,8S,12S,16S)-4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetraone | 138235-99-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (4S,8S,12S,16S)-4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetraone
• 英文别名: (4S,8S,12S,16S)-4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetrone
• CAS: 138235-99-1
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: BFYXIWCSUSKYGL-BJDJZHNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-β-butyrolactone 在 tetrabutyl-tetra-oxa-distanna derivative 作用下， 以 邻二甲苯 为溶剂， 反应 114.0h， 以85 mg的产率得到(4S,8S,12S,16S)-4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetraone
  参考文献：
  名称：

  Cyclische Oligomere von（R）-3-Hydroxybuttersäure：Herstellung和strukturelle Aspekte †

  摘要：

  （R）-3-羟基丁酸的环状低聚物：制备和结构方面。

  DOI：

  10.1002/hlca.19930760518

文献信息

• Group 14 organometallic reagents. 11. Macrocyclic polylactones by catalyzed cyclooligomerization. Tetra[(S)-.beta.-butyrolactone]
  作者：Stefano Roelens、Antonella Dalla Cort、Luigi Mandolini

  DOI：10.1021/jo00031a027

  日期：1992.2

  The synthesis of the elusive macrotetrolide 2 of 3-hydroxybutyric acid has been approached by cyclooligomerization of enantiomerically pure (S)-beta-butyrolactone (3), promoted by the catalytic system 2,2-dibutyl-1,3,2-dioxastannolane/dibutyltin dichloride (DOS/DTC). The product has been isolated in 10% yield, demonstrating that it is not inaccessible, and its structure has been proven by X-ray crystal structure analysis. DOS/DTC afforded a thermodynamically controlled cyclooligomerization mixture, which was analyzed by means of a revised version of the Jacobson-Stockmayer theory, providing an evaluation of the effective molarity (EM) parameter for the formation of the tetrameric macrolide. The EM value was found to be five times lower than the corresponding value for tetra(beta-propiolactone), its strainless unsubstituted analogue. The observed EM allowed a quantitative measure (1.1 kcal mol-1) of the strain induced in the 16-membered macrotetrolide by the introduction of a methyl group into four homochiral stereocenters of the ring. Such relatively small strain is sufficient to depress to an appreciable extent the yield of 2 that can be expected from a thermodynamically controlled reaction. The possible origin of the observed strain is discussed.
• Cyclische Oligomere von (<i>R</i>)-3-Hydroxybuttersäure: Herstellung und strukturelle Aspekte
  作者：Diemar A. Plattner、Andreas Brunner、Max Dobler、Hans-Martin Müller、Walter Petter、Peter Zbinden、Dieter Seebach

  DOI：10.1002/hlca.19930760518

  日期：1993.8.11

  Cyclic Oligomers of (R)-3-Hydroxybutanoic Acid: Preparation and Structural Aspects

  （R）-3-羟基丁酸的环状低聚物：制备和结构方面。