(4R,5S)-3-ethynyl-4,5-diphenyl-1,3-oxazolidin-2-one | 1040389-76-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5S)-3-ethynyl-4,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 1040389-76-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: PRPDCNPGSRABTM-CVEARBPZSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  379.8±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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 、 (4R,5S)-3-ethynyl-4,5-diphenyl-1,3-oxazolidin-2-one 在 dirhodium tetraacetate 作用下， 以 甲苯 为溶剂， 以63%的产率得到methyl 2-methyl-5-[(4R,5S)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]furan-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：

  (4R,5S)-4,5-diphenyl-3-((triisopropylsilyl)ethynyl)oxazolidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(4R,5S)-3-ethynyl-4,5-diphenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A Highly Stereoselective Synthesis of Chiral α-Amino-β-lactams via the Kinugasa Reaction Employing Ynamides

  摘要：

  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.

  DOI：

  10.1021/ol801257j

文献信息

• 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.
• 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.