(+)-methyl (2E,6S)-6-((tert-butoxycarbonyl){[tert-butyl(dimethyl)silyl]oxy}amino)dec-2-enoate | 1304540-25-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-methyl (2E,6S)-6-((tert-butoxycarbonyl){[tert-butyl(dimethyl)silyl]oxy}amino)dec-2-enoate
• 英文别名: methyl (E,6S)-6-[[tert-butyl(dimethyl)silyl]oxy-[(2-methylpropan-2-yl)oxycarbonyl]amino]dec-2-enoate
• CAS: 1304540-25-7
• 化学式: C₂₂H₄₃NO₅Si
• 分子量: 429.673
• InChiKey: NUOSNSJDHHBQTR-UMADGWCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-methyl (2E,6S)-6-((tert-butoxycarbonyl){[tert-butyl(dimethyl)silyl]oxy}amino)dec-2-enoate 在 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以84%的产率得到(+)-tert-butyl (3S)-3-butyl-6-(2-methoxy-2-oxoethyl)-1,2-oxazinane-2-carboxylate
  参考文献：
  名称：

  Enantioselective Iridium-Catalyzed Allylic Substitutions with Hydroxamic Acid Derivatives as N-Nucleophiles

  摘要：

  Enantioselective Ir-catalyzed allylic aminations with hydroxamic acid derivatives are described. Catalysts were prepared in situ from [Ir(cod)Cl](2) or [Ir(dbcot)Cl](2), a phosphoramidite and base. In addition, pure (pi-allyl)Ir complexes containing cod or dbcot as auxiliary ligands were used. Very high degrees of regio- and enantioselectivity were achieved. The reaction products were transformed Into piperidine derivatives suited as precursors for aza-sugars.

  DOI：

  10.1021/ol200688d
• 作为产物：
  描述：

  (E)-3-碘丙烯酸甲酯 、 tert-butyl {[tert-butyl(dimethyl)silyl]oxy}[(1S)-1-butylprop-2-en-1yl]carbamate 在 9-硼双环[3.3.1]壬烷 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三苯胂 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以88%的产率得到(+)-methyl (2E,6S)-6-((tert-butoxycarbonyl){[tert-butyl(dimethyl)silyl]oxy}amino)dec-2-enoate
  参考文献：
  名称：

  Enantioselective Iridium-Catalyzed Allylic Substitutions with Hydroxamic Acid Derivatives as N-Nucleophiles

  摘要：

  Enantioselective Ir-catalyzed allylic aminations with hydroxamic acid derivatives are described. Catalysts were prepared in situ from [Ir(cod)Cl](2) or [Ir(dbcot)Cl](2), a phosphoramidite and base. In addition, pure (pi-allyl)Ir complexes containing cod or dbcot as auxiliary ligands were used. Very high degrees of regio- and enantioselectivity were achieved. The reaction products were transformed Into piperidine derivatives suited as precursors for aza-sugars.

  DOI：

  10.1021/ol200688d

文献信息

• Enantioselective Iridium-Catalyzed Allylic Substitutions with Hydroxamic Acid Derivatives as N-Nucleophiles
  作者：Martin Gärtner、Mascha Jäkel、Manuel Achatz、Christoph Sonnenschein、Olena Tverskoy、Günter Helmchen

  DOI：10.1021/ol200688d

  日期：2011.6.3

  Enantioselective Ir-catalyzed allylic aminations with hydroxamic acid derivatives are described. Catalysts were prepared in situ from [Ir(cod)Cl](2) or [Ir(dbcot)Cl](2), a phosphoramidite and base. In addition, pure (pi-allyl)Ir complexes containing cod or dbcot as auxiliary ligands were used. Very high degrees of regio- and enantioselectivity were achieved. The reaction products were transformed Into piperidine derivatives suited as precursors for aza-sugars.