benzylacetone (S)-1-amino-2-(1'-methoxy-1'-ethylpropyl)pyrrolidine hydrazone | 229639-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: benzylacetone (S)-1-amino-2-(1'-methoxy-1'-ethylpropyl)pyrrolidine hydrazone
• CAS: 229639-89-8
• 化学式: C₂₀H₃₂N₂O
• 分子量: 316.487
• InChiKey: GGDOGPYYKKSOTM-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  phenylhydroxamoyl chloride 、 benzylacetone (S)-1-amino-2-(1'-methoxy-1'-ethylpropyl)pyrrolidine hydrazone 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (2'S,5S)-(-)-4-<2-(1-ethyl-1-methoxypropyl)tetrahydro-1H-1-pyrrolyl>-5-methyl-5-phenylethyl-3-phenyl-4,5-dihydro-1,2,4-oxadiazole 、 (2'S,5R)-(-)-4-<2-(1-ethyl-1-methoxypropyl)tetrahydro-1H-1-pyrrolyl>-5-methyl-5-phenylethyl-3-phenyl-4,5-dihydro-1,2,4-oxadiazole
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of ∆2-1,2,4-Oxadiazolines by 1,3-Dipolar Cycloaddition of Nitrile Oxides with Chiral Hydrazones

  摘要：

  Diastereo- and enantioselective 1,3-dipolar cycloadditions of nitrile oxides (3) with alpha,beta-unsaturated hydrazones (2) gave spiro oxadiazolines (4) in good yields and low to excellent diastereomeric excesses (de = 5 - greater than or equal to 98%). Open chain hydrazones (6) afforded 5,5-disubstituted Delta(2)-1,2,4-oxadiazolines (7). A subsequent N-N bond cleavage to remove the chiral auxiliary was achieved with formic acid and gave the oxadiazolines (8) (ee = 0 - 91%).

  DOI：

  10.3987/com-98-s(h)100
• 作为产物：
  描述：

  苄基丙酮 、 (S)-1-氨基-2-(二乙基甲氧基甲基)吡咯烷 生成 benzylacetone (S)-1-amino-2-(1'-methoxy-1'-ethylpropyl)pyrrolidine hydrazone
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of ∆2-1,2,4-Oxadiazolines by 1,3-Dipolar Cycloaddition of Nitrile Oxides with Chiral Hydrazones

  摘要：

  Diastereo- and enantioselective 1,3-dipolar cycloadditions of nitrile oxides (3) with alpha,beta-unsaturated hydrazones (2) gave spiro oxadiazolines (4) in good yields and low to excellent diastereomeric excesses (de = 5 - greater than or equal to 98%). Open chain hydrazones (6) afforded 5,5-disubstituted Delta(2)-1,2,4-oxadiazolines (7). A subsequent N-N bond cleavage to remove the chiral auxiliary was achieved with formic acid and gave the oxadiazolines (8) (ee = 0 - 91%).

  DOI：

  10.3987/com-98-s(h)100