1-[(7R)-7-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,3,7-tetrahydroindolizin-8-yl]ethanone | 1316335-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(7R)-7-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,3,7-tetrahydroindolizin-8-yl]ethanone
• CAS: 1316335-78-0
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: GCTFWHPLWAHZOV-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(pyrrolidin-2-ylidene)propan-2-one 、 在 piperidinium trifluoroacetate 、 三氟乙酸 、 sodium sulfate 作用下， 以 乙酸乙酯 为溶剂， 生成 、 1-[(7R)-7-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,3,7-tetrahydroindolizin-8-yl]ethanone
  参考文献：
  名称：

  Asymmetric Aza-[3 + 3] Annulation in the Synthesis of Indolizidines: An Unexpected Reversal of Regiochemistry

  摘要：

  An enantioselective and diastereoselective aza-[3 + 3] annulation of pyrrolidine-based exo-cyclic vinylogous amides and urethanes with chiral vinyl iminium salts is described. This asymmetric annulation manifold is possible because of an unexpected regiochemical reversal whereby head-to-tall annulations dominated over the predicted head-to-head. It should find prevalent synthetic applications in the enantioselective synthesis of indolizidines.

  DOI：

  10.1021/ol2017438

文献信息

• Asymmetric <i>Aza-</i>[3 + 3] Annulation in the Synthesis of Indolizidines: An Unexpected Reversal of Regiochemistry
  作者：Grant S. Buchanan、Huifang Dai、Richard P. Hsung、Aleksey I. Gerasyuto、Casi M. Scheinebeck

  DOI：10.1021/ol2017438

  日期：2011.8.19

  An enantioselective and diastereoselective aza-[3 + 3] annulation of pyrrolidine-based exo-cyclic vinylogous amides and urethanes with chiral vinyl iminium salts is described. This asymmetric annulation manifold is possible because of an unexpected regiochemical reversal whereby head-to-tall annulations dominated over the predicted head-to-head. It should find prevalent synthetic applications in the enantioselective synthesis of indolizidines.