(E)-ethyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate | 1197006-43-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate
• 英文别名: (S,E)-ethyl 4-oxo-4-(2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate；ethyl (E)-4-oxo-4-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]but-2-enoate
• CAS: 1197006-43-1
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: RDEURIHPODDFJE-IDVQTMNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate 、 2-(prop-1-en-2-yl)-1-tosylaziridine 在 magnesium iodide 作用下， 以 四氯化碳 为溶剂， 反应 16.08h， 以20%的产率得到
  参考文献：
  名称：

  Concise Synthesis of (+)-allo-Kainic AcidviaMgI₂-Mediated Tandem Aziridine Ring Opening–Formal [3 + 2] Cycloaddition

  摘要：

  3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

  DOI：

  10.1021/ol4020333
• 作为产物：
  描述：

  富马酸单乙酯 、 (S)-4-苯基-2-恶唑烷酮 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到(E)-ethyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate
  参考文献：
  名称：

  Concise Synthesis of (+)-allo-Kainic AcidviaMgI₂-Mediated Tandem Aziridine Ring Opening–Formal [3 + 2] Cycloaddition

  摘要：

  3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

  DOI：

  10.1021/ol4020333

文献信息

• Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid
  作者：Mukund P. Sibi、Takahiro Soeta、Craig P. Jasperse

  DOI：10.1021/ol9018584

  日期：2009.12.3

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.
• Concise Synthesis of (+)-<i>allo</i>-Kainic Acid<i>via</i>MgI₂-Mediated Tandem Aziridine Ring Opening–Formal [3 + 2] Cycloaddition
  作者：Giada Arena、C. Chun Chen、Daniele Leonori、Varinder K. Aggarwal

  DOI：10.1021/ol4020333

  日期：2013.8.16

  3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.