(4S,8S,12S,16S,20S,24S)-4,8,12,16,20,24-hexamethyl-1,5,9,13,17,21-hexaoxacyclotetracosane-2,6,10,14,18,22-hexone | 116838-43-8

• 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,20S,24S)-4,8,12,16,20,24-hexamethyl-1,5,9,13,17,21-hexaoxacyclotetracosane-2,6,10,14,18,22-hexone
• CAS: 116838-43-8
• 化学式: C₂₄H₃₆O₁₂
• 分子量: 516.543
• InChiKey: PMHIUPBVFLRBRA-QQCJEOGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  36.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  157.8
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  (3S)-3-(2,4,6-trichlorobenzoyl)oxybutanoic acid 以13%的产率得到
  参考文献：
  名称：

  SEEBACH, DIETER;BRANDLI, URS;SCHNURRENBERGER, PETER;PRZYBYLSKI, MICHAEL, HELV. CHIM. ACTA, 71,(1988) N 1, 155-167

  摘要：

  DOI：

文献信息

• 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。
• High-Yield Synthesis of 20-, 24-, and 28-Membered Macropentolide, -hexolide, and -heptolide, Respectively, from (<i>R</i>)- or (<i>S</i>)-3-hydroxybutanoic acid under<i>Yamaguchi</i>'s macrolactonization conditions
  作者：Dieter Seebach、Urs Brändli、Peter Schnurrenberger、Michael Przybylski

  DOI：10.1002/hlca.19880710119

  日期：1988.2.3

  oligomers formed in ca. 50% yield from enantiomerically pure 3-hydroxybutanoic acid under Yamaguchi's macrolactonization conditions. The FAB mass spectra of the MH+, M Na+, and MCs+ are reported (Figs. 2, 3, 5, and 6). No cyclic tetramer is detected. The 1H-NMR spectra of the cyclic oligomers, of the monomer, and of the polymer (PHB) are very similar (Fig. 4). Directed synthesis of the open-chain dimer and

  大环戊内酯1，己内酯2和庚内酯3构成ca。形成在所述低聚物的80％约 在山口的大环内酯化条件下，对映体纯的3-羟基丁酸的收率为50％。报道了M H +，M Na +和M Cs +的FAB质谱图（图2、3、5和6）。未检测到环状四聚体。环状低聚物，单体和聚合物（PHB）的1 H-NMR谱图非常相似（图4）。3-羟基丁酸的开链二聚体和四聚体的直接合成和尝试的环化作用不会导致环状四聚体的分离。
• On the Macrolactonization of β-Hydroxy Acids. Crystal structures of the pentolide and the hexolide from (<i>R</i>)-3-hydroxybutanoic acid. Molecular modeling studies of the tetrolide
  作者：Dieter Seebach、Urs Brändli、Hans-Martin Müller、Max Dobler、Martin Egli、Michael Przybylski、Klaus Schneider

  DOI：10.1002/hlca.19890720807

  日期：1989.12.13

  from (R)- or (S)-3-hydroxybutanoic acid under Yamaguchi's macrolactonization conditions (2,4,6-trichlorobenzoyl chloride/base) was studied. While the content of hexolide 2 in the product mixture is almost invariably ca. 35%, the amounts of pentolide 1 and of the larger rings strongly depend upon the temperature employed (Fig.1). Cyclic oligomers (5,6) are also obtained from 3-hydroxypentanoic acid. Enantiomerically

  研究了先前报道的在山口的大环内酯化条件（2,4,6-三氯苯甲酰氯/碱）下由（R）-或（S）-3-羟基丁酸形成寡核苷酸的温度和浓度依赖性。虽然产物混合物中己内酯2的含量几乎总是约为1。35％的戊内酯1和较大的环的数量在很大程度上取决于所采用的温度（图1）。环状低聚物（5，6）也由3-羟基戊酸获得。对映体纯的β-丁内酯可在Shanzer's的条件下用于制备戊，己和庚内酯宏观内酯化条件（四氧杂环丁烷环癸烷“模板”）。所述pentolide的X射线晶体结构1和两个修饰（空间群c ^ 2和P 2 1的hexolide的）2进行了测定（图2-6和表1和表5）。在这些结构中，没有观察到取代基原子与环中的原子之间或环原子之间的紧密接触。己内酯C 2的修饰“只是一个大环”，而P 2 1的晶体改型包含折叠环，其骨架类似于网球的接缝。比较P 2 1修饰的折叠己内环与螺旋聚（R）-3-羟基丁酸酯（PHB）中的扭转
• 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.