methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-pyridyl)-4-pentynoate | 848132-24-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-pyridyl)-4-pentynoate
• 英文别名: methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-pyridin-3-ylpent-4-ynoate
• CAS: 848132-24-1
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: FEAGQDHYBSZFCM-ZDUSSCGKSA-N

物化性质

• 沸点：
  466.6±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-pyridyl)-4-pentynoate 在 盐酸 、 silver trifluoromethanesulfonate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 9.0h， 生成 methyl (2S)-5-(3-pyridyl)-3,4-dihydro-2H-2-pyrrolecarboxylate
  参考文献：
  名称：

  Novel Approach to 5-Substituted Proline Derivatives Using a Silver-Catalyzed Cyclization as the Key Step

  摘要：

  [GRAPHICS]A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids. It has also been shown that the obtained pyrrolines can be efficiently transformed into the corresponding saturated 5-aryl-substituted proline derivatives.

  DOI：

  10.1021/jo0484023
• 作为产物：
  描述：

  3-碘吡啶 、 (2S)-2-[[叔丁氧羰基]氨基]-4-戊炔酸酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以91%的产率得到methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-pyridyl)-4-pentynoate
  参考文献：
  名称：

  Novel Approach to 5-Substituted Proline Derivatives Using a Silver-Catalyzed Cyclization as the Key Step

  摘要：

  [GRAPHICS]A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids. It has also been shown that the obtained pyrrolines can be efficiently transformed into the corresponding saturated 5-aryl-substituted proline derivatives.

  DOI：

  10.1021/jo0484023

文献信息

• Novel Approach to 5-Substituted Proline Derivatives Using a Silver-Catalyzed Cyclization as the Key Step
  作者：Bart C. J. van Esseveldt、Paul W. H. Vervoort、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo0484023

  日期：2005.3.1

  [GRAPHICS]A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids. It has also been shown that the obtained pyrrolines can be efficiently transformed into the corresponding saturated 5-aryl-substituted proline derivatives.