tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate | 1237479-25-2

• 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 ((2R,3R)-1-(tert-butyldimethylsilyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate
• 英文别名: tert-butyl N-[(2R,3R)-1-[tert-butyl(dimethyl)silyl]-2-(hydroxymethyl)-4-oxoazetidin-3-yl]carbamate
• CAS: 1237479-25-2
• 化学式: C₁₅H₃₀N₂O₄Si
• 分子量: 330.5
• InChiKey: BDBDDQBKPMKTJO-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以95%的产率得到tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-formyl-4-oxoazetidin-3-yl)carbamate
  参考文献：
  名称：

  Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst

  摘要：

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.064
• 作为产物：
  描述：

  在 锂硼氢 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 4.0h， 以633 mg的产率得到tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate
  参考文献：
  名称：

  Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst

  摘要：

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.064

文献信息

• Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst
  作者：Xiangbing (Ben) Qi、Grant T. Rice、Manjinder S. Lall、Mark S. Plummer、M. Christina White

  DOI：10.1016/j.tet.2010.04.064

  日期：2010.6

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.