tert-butyl N-[(2S,3R)-2-cyclohexyl-4-oxoazetidin-3-yl]carbamate | 1040389-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: tert-butyl N-[(2S,3R)-2-cyclohexyl-4-oxoazetidin-3-yl]carbamate
• CAS: 1040389-94-3
• 化学式: C₁₄H₂₄N₂O₃
• 分子量: 268.356
• InChiKey: ZTHWUQRJHGUUGT-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 4.25h， 以77%的产率得到tert-butyl N-[(2S,3R)-2-cyclohexyl-4-oxoazetidin-3-yl]carbamate
  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.