2-((S)-N-(ethylcarbonyl)-pyrrolidin-2-yl)-5,6-dihydro-4H-1,3-oxazine | 1393707-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-((S)-N-(ethylcarbonyl)-pyrrolidin-2-yl)-5,6-dihydro-4H-1,3-oxazine
• CAS: 1393707-78-2
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: JIHKXJCBUVEFKF-VIFPVBQESA-N

反应信息

• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到2-((S)-N-(ethylcarbonyl)-pyrrolidin-2-yl)-5,6-dihydro-4H-1,3-oxazine
  参考文献：
  名称：

  A method for stabilizing the cis prolyl peptide bond: influence of an unusual n→π∗ interaction in 1,3-oxazine and 1,3-thiazine containing peptidomimetics

  摘要：

  The cis/trans isomer ratios of the Xaa-Pyr (Pyr = pyrrolidine) 3 degrees amide bonds are significantly high (similar to 90% cis) in the novel peptidomimetics where Pyr contains 1,3-oxazine (Oxa) or 1,3-thiazine (Thi) at its 2 position. We find that an unusual n -> pi(i-1)* interaction, selectively stabilizes the cis conformer and the n X n repulsion destabilizes the trans conformer of these molecules. Both these electronic effects oppose the steric effects in the 3 degrees amide bond. The structural requirements for manifestation of these electronic effects are determined. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.031