(5R,6S)-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxydecan-5-ol | 1613336-94-9

• 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: (5R,6S)-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxydecan-5-ol
• CAS: 1613336-94-9
• 化学式: C₁₉H₃₉NO₂
• 分子量: 313.524
• InChiKey: OHOUTFBJKZCGBJ-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 在 copper(II) choride dihydrate 、 (5S)-5-benzyl-2,2,3-trimethyl-4-oxoimidazolidin-1-ium Tetrafluoroborate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.2h， 生成 (5R,6S)-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxydecan-5-ol 、
  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

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.