(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(4-hydroxybut-2-ynyl)-2-azetidinone | 457068-80-3

• 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: (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(4-hydroxybut-2-ynyl)-2-azetidinone
• 英文别名: (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(4-hydroxybut-2-ynyl)azetidin-2-one
• CAS: 457068-80-3
• 化学式: C₁₅H₂₇NO₃Si
• 分子量: 297.47
• InChiKey: RRVSIFWZKIZAFW-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(4-hydroxybut-2-ynyl)-2-azetidinone 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以94%的产率得到(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-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-(3,3-dibromoprop-2-enyl)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone 在 potassium fluoride 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.5h， 生成 (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(4-hydroxybut-2-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

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).