trans-4-acetoxyoctane-5-ol | 55668-10-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-4-acetoxyoctane-5-ol
• 英文别名: (4R,5R)-5-hydroxyoctan-4-yl acetate；threo-2-Hydroxy-1-propylpentylacetat
• CAS: 55668-10-5
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: QSSYGKHCGOLUDN-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 trans-4-acetoxyoctane-5-ol 在 sodium acetate 作用下， 生成 D,L-1,2-Dipropylethylenediacetate
  参考文献：
  名称：

  Lethbridge,A. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 231 - 241

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-epoxyoctane 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 51.0h， 生成 trans-4-acetoxyoctane-5-ol
  参考文献：
  名称：

  Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols

  摘要：

  Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full potential of the employed oligopeptides. Additionally, we utilized NMR and IR-spectroscopic methods as well as computations to shed light on the factors responsible for the selectivity. The catalyst system can be readily modified to a multicatalyst by adding other catalytically active amino acids to the peptide backbone, enabling the stereoselective one-pot synthesis of complex molecules from simple starting materials.

  DOI：

  10.1021/jo401195c

文献信息

• Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
  作者：Mio Shimogaki、Morifumi Fujita、Takashi Sugimura

  DOI：10.3390/molecules200917041

  日期：——

  achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product.

  通过组装三个组分：烯烃，羧酸和甲硅烷基烯醇醚，可以实现立体选择性地形成取代的1,3-二氧戊环。该反应通过在烯烃底物与高价碘的氧化过程中通过立体定向生成1，3-二氧戊环-2-基阳离子中间体而进行。用甲硅烷基烯醇醚对阳离子中间体的立体选择性捕集完成了二氧戊环产物的形成。
• Enantiomerically enriched trans-diols from alkenes in one pot: a multicatalyst approach
  作者：Radim Hrdina、Christian E. Müller、Raffael C. Wende、Lukas Wanka、Peter R. Schreiner

  DOI：10.1039/c2cc17435a

  日期：——

  Multicatalysts consisting of non-natural oligopeptides with distinctly different catalytic moieties create molecular complexity in a multistep one-pot sequence starting from simple alkenes yielding highly enantiomerically enriched trans-diols.

  由非天然寡肽组成的多催化剂，具有明显不同的催化基团，在从简单的烯烃出发的多步一锅反应中创造了分子复杂性，最终生成具有高度对映体富集的反式二醇。