trans-5-benzoyl-4-(naphthalen-1-yl)oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-5-benzoyl-4-(naphthalen-1-yl)oxazolidin-2-one
• 英文别名: anti-5-benzoyl-4-(naphthalen-1-yl)oxazolidin-2-one；(4S,5R)-5-benzoyl-4-naphthalen-1-yl-1,3-oxazolidin-2-one
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: JNTUBCSAAUAKHG-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-硝基乙烯基)萘 、 (benzoylmethylene)dimethylsulfurane 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以84%的产率得到trans-5-benzoyl-4-(naphthalen-1-yl)oxazolidin-2-one
  参考文献：
  名称：

  A New Entry to Cascade Organocatalysis: Reactions of Stable Sulfur Ylides and Nitroolefins Sequentially Catalyzed by Thiourea and DMAP

  摘要：

  A novel cascade organocatalysis that allows efficient and rapid access to diverse and structurally complex oxazolidin-2-ones from simple starting materials and catalysts has been developed. A possible mechanism of this reaction has been proposed based on D- and (13)C-labeling experiments.

  DOI：

  10.1021/ja800746q

文献信息

• Reactions of Nitroalkenes with Nitroalkanes or Sulfur Ylides Catalyzed by Amine-Thiourea Bifunctional Polymeric Organocatalysts
  作者：Patrick Toy、Jinni Lu

  DOI：10.1055/s-0031-1289900

  日期：2011.12

  Non-cross-linked and cross-linked bifunctional polystyrenes bearing both amine and thiourea groups have been synthesized and used as organocatalysts in reactions between nitroalkenes and nitroalkanes or sulfur ylides. Control experiments using monofunctional polymers with only either amine or thiourea groups attached indicated that both functional groups were essential for efficient catalysis of the reactions studied. The non-cross-linked polystyrene was soluble in typical organic solvents and was used as a homogeneous catalyst, while the cross-linked polystyrene was used as a heterogeneous catalyst.

  具有氨基和硫脲基团的双功能非交联和交联聚苯乙烯已被合成，并作为有机催化剂用于硝基烯烃与硝基烷烃或硫叶立德之间的反应。通过仅附着胺或硫脲基团的单功能聚合物的对照实验表明，两种功能基团对于所研究反应的高效催化都至关重要。非交联聚苯乙烯可溶于典型的有机溶剂，被用作均相催化剂，而交联聚苯乙烯则用作非均相催化剂。
• Enantioselective Cascade Reactions of Stable Sulfur Ylides and Nitroolefins through an Axial-to-Central Chirality Transfer Strategy
  作者：Liang-Qiu Lu、Zhi-Hui Ming、Jing An、Chao Li、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1021/jo202324f

  日期：2012.1.20

  Moreover, this strategy was also successfully applied to the asymmetric [4 + 1]/[3 + 2] cycloaddition cascade of sulfur ylides with alkene-tethered nitroolefins, and the corresponding enantioenriched fused heterocycles (up to 87:13 e.r. and >95:5 d.r.) were obtained in good to excellent yields (54–95% yields).

  通过使用手性BINOL衍生的硫化物作为可靠的立体调节剂，通过有效的轴向向中心手性转移，已经开发了稳定的硫代烷基化物和硝基烯烃的对映选择性[4 +1]环合/重排级联。它可以提供高立体选择性（高达96：4 er和> 95：5 dr）的药学和合成上重要的恶唑烷酮。此外，该策略还成功地应用于硫代烷基化物与链烯连接的硝基烯烃的不对称[4 +1] / [3 + 2]环加成级联反应，以及相应的对映体富集的稠合杂环（高达87:13 er和> 95：以良好至极高的收率（54–95％的收率）获得了5个博士）。
• A New Entry to Cascade Organocatalysis: Reactions of Stable Sulfur Ylides and Nitroolefins Sequentially Catalyzed by Thiourea and DMAP
  作者：Liang-Qiu Lu、Yi-Ju Cao、Xiao-Peng Liu、Jing An、Chang-Jiang Yao、Zhi-Hui Ming、Wen-Jing Xiao

  DOI：10.1021/ja800746q

  日期：2008.6.1

  A novel cascade organocatalysis that allows efficient and rapid access to diverse and structurally complex oxazolidin-2-ones from simple starting materials and catalysts has been developed. A possible mechanism of this reaction has been proposed based on D- and (13)C-labeling experiments.