methyl (2S)-2-amino-5-(4-fluorophenyl)pent-4-ynoate | 1025882-63-6

• 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-amino-5-(4-fluorophenyl)pent-4-ynoate
• CAS: 1025882-63-6
• 化学式: C₁₂H₁₂FNO₂
• 分子量: 221.231
• InChiKey: YRYGJADWGHNKAV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-amino-5-(4-fluorophenyl)pent-4-ynoate 在 silver trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 以174 mg的产率得到methyl (2S)-5-(4-fluorophenyl)-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：

  (2S)-2-[[叔丁氧羰基]氨基]-4-戊炔酸酸甲酯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 methyl (2S)-2-amino-5-(4-fluorophenyl)pent-4-ynoate
  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.