(R)-4-benzyl-3-ethynyloxazolidin-2-one | 503590-22-5

• 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: (R)-4-benzyl-3-ethynyloxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-ethynyl-1,3-oxazolidin-2-one
• CAS: 503590-22-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: QRDZTUOKOGFHMC-LLVKDONJSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  294.7±23.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Diazo-3-oxo-butyric acid methyl ester 、 (R)-4-benzyl-3-ethynyloxazolidin-2-one 在 dirhodium tetraacetate 作用下， 以 甲苯 为溶剂， 以61%的产率得到methyl (R)-5-(4-benzyl-2-oxooxazolidin-3-yl)-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  Highly Substituted 2-Amido-furans From Rh(II)-Catalyzed Cyclopropenations of Ynamides

  摘要：

  Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-turans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-turans in N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroquinolines.

  DOI：

  10.1021/ol901860b
• 作为产物：
  描述：

  (R)-4-Benzyl-3-[(triisopropylsilanyl)-ethynyl]-oxazolidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-4-benzyl-3-ethynyloxazolidin-2-one
  参考文献：
  名称：

  Highly Substituted 2-Amido-furans From Rh(II)-Catalyzed Cyclopropenations of Ynamides

  摘要：

  Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-turans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-turans in N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroquinolines.

  DOI：

  10.1021/ol901860b

文献信息

• Penta-2,4-dien-1-ones by Formal [3+2] Cycloaddition-Rearrangement of Electron-Deficient Diethyl 2-(Dicyanomethylene)malonate with Alk­ynes
  作者：Etienne J. Donckele、Tristan A. Reekie、Nils Trapp、François Diederich

  DOI：10.1002/ejoc.201501473

  日期：2016.2

  The reactions of diethyl 2-(dicyanomethylene)malonate, an electron-deficient alkene, with donor-activated and unactivated alkynes have been investigated. Moderately electron-rich and unactivated alkynes undergo efficient formal [3+2] cycloaddition–rearrangement cascades to provide the corresponding penta-2,4-dien-1-one adducts in yields of up to 84 %. The structures of the solid dienone products were

  已经研究了 2-（二氰基亚甲基）丙二酸二乙酯（一种缺电子烯烃）与供体活化和未活化的炔烃的反应。中等富电子和未活化的炔烃经过有效的正式 [3+2] 环加成 - 重排级联反应，以高达 84% 的产率提供相应的 penta-2,4-dien-1-one 加合物。固体二烯酮产物的结构通过X射线衍射分析证实。二烯酮中的buta-1,3-diene 部分不采用平面s-trans 构象，而是采用非平面几何结构，其中两个烯键几乎彼此正交。这种转化以优异的区域选择性和广泛的炔烃进行，无需催化剂。在优化的反应条件下，
• A Highly Stereoselective Synthesis of Chiral α-Amino-β-lactams via the Kinugasa Reaction Employing Ynamides
  作者：Xuejun Zhang、Richard P. Hsung、Hongyan Li、Yu Zhang、Whitney L. Johnson、Ruth Figueroa

  DOI：10.1021/ol801257j

  日期：2008.8.21

  A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.
• A Copper-Catalyzed C−N Bond Formation Involving sp-Hybridized Carbons. A Direct Entry to Chiral Ynamides via N-Alkynylation of Amides
  作者：Michael O. Frederick、Jason A. Mulder、Michael R. Tracey、Richard P. Hsung、Jian Huang、Kimberly C. M. Kurtz、Lichun Shen、Christopher J. Douglas

  DOI：10.1021/ja021304j

  日期：2003.3.1

  A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.
• Highly Substituted 2-Amido-furans From Rh(II)-Catalyzed Cyclopropenations of Ynamides
  作者：Hongyan Li、Richard P. Hsung

  DOI：10.1021/ol901860b

  日期：2009.10.1

  Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-turans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-turans in N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroquinolines.