(4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-phenylmethoxymethoxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone | 1019107-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-phenylmethoxymethoxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone
• CAS: 1019107-73-3
• 化学式: C₂₅H₂₉NO₅
• 分子量: 423.509
• InChiKey: OPMRSRYDQJAZTG-KPRXDRPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-phenylmethoxymethoxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone 在 ammonium chloride 、 lithium iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以69%的产率得到(4R)-4,5-dihydro-2-[(1S,2S,3E)-1-methyl-2-phenylmethoxymethoxy-3-pentenyl]-4-(phenylmethyl)oxazole
  参考文献：
  名称：

  Decarboxylative Isomerization of N-Acyl-2-oxazolidinones to 2-Oxazolines

  摘要：

  N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50 degrees C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

  DOI：

  10.1021/jo800076f
• 作为产物：
  描述：

  苄基氯甲基醚 、 (4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-hydroxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以97%的产率得到(4R)-3-[(2S,3S,4E)-2-methyl-1-oxo-3-phenylmethoxymethoxy-4-hexenyl]-4-phenylmethyl-2-oxazolidinone
  参考文献：
  名称：

  Decarboxylative Isomerization of N-Acyl-2-oxazolidinones to 2-Oxazolines

  摘要：

  N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50 degrees C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

  DOI：

  10.1021/jo800076f