(R)-4-Benzhydryl-3-[(triisopropylsilanyl)-ethynyl]-oxazolidin-2-one | 503590-34-9

• 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: (R)-4-Benzhydryl-3-[(triisopropylsilanyl)-ethynyl]-oxazolidin-2-one
• 英文别名: (4R)-4-benzhydryl-3-[2-tri(propan-2-yl)silylethynyl]-1,3-oxazolidin-2-one
• CAS: 503590-34-9
• 化学式: C₂₇H₃₅NO₂Si
• 分子量: 433.666
• InChiKey: CONFKAZTQKHEIQ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (R)-4-Benzhydryl-3-[(triisopropylsilanyl)-ethynyl]-oxazolidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到
  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
• 作为产物：
  描述：

  (2-溴乙炔基)三异丙基硅烷 、 (R)-(+)-4-(二苯基甲基)-2-恶唑烷酮 在 potassium phosphate 、 N,N'-二甲基乙二胺 作用下， 以 xylene 为溶剂， 以72%的产率得到(R)-4-Benzhydryl-3-[(triisopropylsilanyl)-ethynyl]-oxazolidin-2-one
  参考文献：
  名称：

  A Copper-Catalyzed C−N Bond Formation Involving sp-Hybridized Carbons. A Direct Entry to Chiral Ynamides via N-Alkynylation of Amides

  摘要：

  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.

  DOI：

  10.1021/ja021304j

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.
• 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.