(2S)-2-(2,2,6,6-tetramethylpiperidin-1-yl)oxyhexanal | 1613336-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S)-2-(2,2,6,6-tetramethylpiperidin-1-yl)oxyhexanal
• CAS: 1613336-93-8
• 化学式: C₁₅H₂₉NO₂
• 分子量: 255.401
• InChiKey: QTDXDFGZTSSBKX-ZDUSSCGKSA-N

物化性质

• 沸点：
  303.1±44.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-(2,2,6,6-tetramethylpiperidin-1-yl)oxyhexanal 、 异丙烯基溴化镁 以 四氢呋喃 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense

  摘要：

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.

  DOI：

  10.1021/ol501263y
• 作为产物：
  描述：

  正己醇 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 (S)-5-benzyl-2,2,3-trimethylimidazolidine-4-thione 、 三氟乙酸 、 sodium bromide 、 copper dichloride 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (2S)-2-(2,2,6,6-tetramethylpiperidin-1-yl)oxyhexanal 、
  参考文献：
  名称：

  咪唑硫酮和金属盐的协同催化醛的不对称α-氧胺化†

  摘要：

  新型高效的咪唑硫酮催化剂与金属盐的结合已成功引入醛类的不对称α-氧胺化反应中。通过一锅氧化-氧化胺化反应系统，可以得到所需的高收率和良好至优异对映选择性的产物。

  DOI：

  10.1039/c4ra08556f

文献信息

• <i>anti</i>-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from <i>Dracontium loretense</i>
  作者：Gayan A. Abeykoon、Shreyosree Chatterjee、Jason S. Chen

  DOI：10.1021/ol501263y

  日期：2014.6.20

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.
• Asymmetric α-oxyamination of aldehydes by synergistic catalysis of imidazolethiones and metal salts
  作者：Xianrui Liang、Na Li、Xinlei Chen、Weike Su

  DOI：10.1039/c4ra08556f

  日期：——

  Novel and efficient imidazolethione catalysts combined with metal salts were successfully introduced to the asymmetric α-oxyamination of aldehydes. The desired products with high yields and good to excellent enantioselectivities were obtained via a one-pot oxidation–oxyamination reaction system.

  新型高效的咪唑硫酮催化剂与金属盐的结合已成功引入醛类的不对称α-氧胺化反应中。通过一锅氧化-氧化胺化反应系统，可以得到所需的高收率和良好至优异对映选择性的产物。