(5R,6S)-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-1-methyl-3-methylidene-carbapen-1-em

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: (5R,6S)-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-1-methyl-3-methylidene-carbapen-1-em
• 英文别名: (5S,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methyl-2-methylidene-1-azabicyclo[3.2.0]hept-3-en-7-one
• 化学式: C₁₆H₂₇NO₂Si
• 分子量: 293.481
• InChiKey: NILCWIVVPDTJDB-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[3,3-dibromo-(R)-1-methylprop-2-enyl]-2-azetidinone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 4-二甲氨基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 potassium fluoride 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (5R,6S)-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-1-methyl-3-methylidene-carbapen-1-em
  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).