(2'S,2R,3S,4S)-{[2-(4-bromophenyl)-3,4-dihydro-4-methyl-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine | 1197007-12-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: (2'S,2R,3S,4S)-{[2-(4-bromophenyl)-3,4-dihydro-4-methyl-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine
• 英文别名: (4S)-3-[(2R,3S,4S)-5-(4-bromophenyl)-4-methyl-2-(4-nitrophenyl)-3,4-dihydro-2H-pyrrole-3-carbonyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1197007-12-7
• 化学式: C₂₇H₂₂BrN₃O₅
• 分子量: 548.393
• InChiKey: HVLRRSFGPMCZQZ-XHIRGIGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'S,2R,3S,4S)-{[2-(4-bromophenyl)-3,4-dihydro-4-methyl-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 ((2R,3S,4S)-5-(4-bromophenyl)-3,4-dihydro-4-methyl-2-(4-nitrophenyl)-2H-pyrrol-3-yl)methanol
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  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.

  DOI：

  10.1021/ol9018584
• 作为产物：
  描述：

  N-((4-bromophenyl)chloromethylene)(4-nitrophenyl)methanamine 、 (4S)-N-crotonyl-4-phenyloxazolidin-2-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到(2'S,2R,3S,4S)-{[2-(4-bromophenyl)-3,4-dihydro-4-methyl-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  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.

  DOI：

  10.1021/ol9018584

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.