2-[(2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanal | 622410-48-4

• 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: 2-[(2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanal
• CAS: 622410-48-4
• 化学式: C₂₀H₄₁NO₃Si₂
• 分子量: 399.721
• InChiKey: KYODVYXAEDTXOG-XMMHPARDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanal 在 咪唑 、 正丁基锂 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.5h， 生成 (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R,2S)-2-tert-butyldimethylsilyloxy-1-methylbut-3-ynyl]-2-azetidinone
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c
• 作为产物：
  描述：

  (3S,4R)-4-but-3-en-2-yl-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one 在 氧气 、 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以485 mg的产率得到2-[(2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanal
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c

文献信息

• Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1021/jo030123c

  日期：2003.10.1

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).