cis-3-(2,2,5,5-Ttetramethyl-1-aza-2,5-disilacyclopentyl)-4-(2-furyl)-2-azetidinone | 135613-81-9

• 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: cis-3-(2,2,5,5-Ttetramethyl-1-aza-2,5-disilacyclopentyl)-4-(2-furyl)-2-azetidinone
• CAS: 135613-81-9
• 化学式: C₁₃H₂₂N₂O₂Si₂
• 分子量: 294.501
• InChiKey: HEFZFTKOJMZYEA-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1-乙氧基羰基甲基)-2,2,5,5-四甲基-1-氮杂-2,5-二硅杂环戊烷 、 (furan-2-ylmethylene)(trimethylsilanyl)amine 在 lithium diisopropyl amide 作用下， 生成 cis-3-(2,2,5,5-Ttetramethyl-1-aza-2,5-disilacyclopentyl)-4-(2-furyl)-2-azetidinone 、 trans-1-Trimethylsilyl-3-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)-4-(2-furyl)-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of cis- and trans-.beta.-lactams via .alpha.-amino ester enolates and 1-aza-4-hetero-1,3-butadiene systems. Molecular structure of [cyclic] EtOC(O)C(H)(NEt2)C(H)(N(H)-tert-Bu)C(H):N(tert-Bu)ZnCl2: An unexpectedly isolated aldolate

  摘要：

  Lithium and zinc enolates of N,N-diprotected glycine esters 1 react with 1-aza-4-hetero-1,3-butadiene systems 4 selectively affording cis- and trans-3-amino-4-functionalized-2-azetidinones in excellent yields, respectively. The reactions with 1,4-diaza-1,3-butadiene systems are far more selective (de greater-than-or-equal-to 90%) than those with 1-aza-4-oxo- and 1-aza-4-thio-1,3-butadiene systems (de 0-85%). In apolar solvents some of the reactions between the zinc enolates 2 and functionalized imines 4 partly stop at the stage of the C-C coupled product, probably because the metal center migrates to a chelating position between the nitrogen and the hetero atom of the imine. Consequently, elimination of the metal alkoxide and ring closure to a 2-azetidinone product is not likely to occur anymore. This view is supported by the isolation and structural characterization of a ZnCl2 complex of a C-C coupled product, erythro-EtOC(O)C(H)(NEt2)C(H) activated (N(H)-t-Bu)C(H) = N(t-Bu)ZnCl2 (8), which furthermore demonstrates that erythro C-C bond formation leads to a trans-2-azetidinone product. In polar solvents the migration of the metal center is prevented and exclusively 2-azetidinone products are isolated.

  DOI：

  10.1021/jo00020a031