5-methyl-5-vinyloxazolidinone | 1500092-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methyl-5-vinyloxazolidinone
• 英文别名: 5-Methyl-3-((4-nitrophenyl)sulfonyl)-5-vinyloxazolidin-2-one；5-ethenyl-5-methyl-3-(4-nitrophenyl)sulfonyl-1,3-oxazolidin-2-one
• CAS: 1500092-64-7
• 化学式: C₁₂H₁₂N₂O₆S
• 分子量: 312.303
• InChiKey: OYGLPUSQKLUJEK-UHFFFAOYSA-N

物化性质

• 沸点：
  443.9±55.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methyl-5-vinyloxazolidinone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 C₅₆H₄₁F₆NP⁽¹⁺⁾*I^(1-) 、 caesium carbonate 、 三乙胺 、 十二硫醇 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition of 5-Vinyloxazolidinones with Imines Using Chiral Ammonium-Phosphine Hybrid Ligand

  摘要：

  A palladium-catalyzed asymmetric [3 + 2] annulation reaction between racemic 5-vinyloxazolidinones and N-sulfonyl imines was established. Under the influence of the palladium complex with a chiral ammonium-phosphine hybrid ligand, the cycloaddition proceeded smoothly to yield imidazolidines bearing alpha-amino quaternary stereocenters in high yields with excellent diastereo- and enantioselectivities.

  DOI：

  10.1021/cs501369z

文献信息

• Multiple Absolute Stereocontrol in Pd-Catalyzed [3+2] Cycloaddition of Oxazolidinones and Trisubstituted Alkenes Using Chiral Ammonium–Phosphine Hybrid Ligands
  作者：Naomichi Imagawa、Yuya Nagato、Kohsuke Ohmatsu、Takashi Ooi

  DOI：10.1246/bcsj.20160053

  日期：2016.6.15

  The development of a Pd-catalyzed highly enantio- and diastereoselective [3+2] cycloaddition of 5-vinyloxazolidinones and activated trisubstituted alkenes is described in detail. This protocol for ...

  详细描述了 Pd 催化的 5-乙烯基恶唑烷酮和活化的三取代烯烃的高度对映选择性和非对映选择性 [3+2] 环加成的发展。该协议用于...
• Ligand-enabled multiple absolute stereocontrol in metal-catalysed cycloaddition for construction of contiguous all-carbon quaternary stereocentres
  作者：Kohsuke Ohmatsu、Naomichi Imagawa、Takashi Ooi

  DOI：10.1038/nchem.1796

  日期：2014.1

  The development of a general catalytic method for the direct and stereoselective construction of contiguous all-carbon quaternary stereocentres remains a formidable challenge in chemical synthesis. Here, we report a highly enantio- and diastereoselective [3+2] annulation reaction of 5-vinyloxazolidinones and activated trisubstituted alkenes catalysed by a palladium complex bearing a newly devised phosphine

  开发用于直接和立体选择性构建连续全碳四元立体中心的通用催化方法仍然是化学合成中的一项艰巨挑战。在这里，我们报告了 5-乙烯基恶唑烷酮和活化的三取代烯烃的高度对映选择性和非对映选择性 [3+2] 环化反应，该反应由带有新设计的具有手性铵盐组分的膦配体的钯配合物催化，这使得单步构建成为可能三个连续的立体中心，包括相邻的全碳四元立体中心，在五元杂环框架中。这种立体选择性环加成方案依赖于手性配体的卓越能力，以严格控制与多个键形成事件相关的每个手性中心的绝对立体化学，
• Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition of 5-Vinyloxazolidinones with Imines Using Chiral Ammonium-Phosphine Hybrid Ligand
  作者：Kohsuke Ohmatsu、Shinya Kawai、Naomichi Imagawa、Takashi Ooi

  DOI：10.1021/cs501369z

  日期：2014.12.5

  A palladium-catalyzed asymmetric [3 + 2] annulation reaction between racemic 5-vinyloxazolidinones and N-sulfonyl imines was established. Under the influence of the palladium complex with a chiral ammonium-phosphine hybrid ligand, the cycloaddition proceeded smoothly to yield imidazolidines bearing alpha-amino quaternary stereocenters in high yields with excellent diastereo- and enantioselectivities.