N-(1-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-2-oxo-butyrimidoyl chloride | 1026386-24-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(1-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-2-oxo-butyrimidoyl chloride
• CAS: 1026386-24-2
• 化学式: C₁₇H₃₄ClNOSi₂
• 分子量: 360.087
• InChiKey: GEFXEVSHIXWNKC-ZPHPHTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(1-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-2-oxo-butyrimidoyl chloride 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 1-[(3R,5R)-5-Methyl-3-(1-trimethylsilanylmethyl-vinyl)-4,5-dihydro-3H-pyrrol-2-yl]-propan-1-one 、 1-[(3R,5S)-5-Methyl-3-(1-trimethylsilanylmethyl-vinyl)-4,5-dihydro-3H-pyrrol-2-yl]-propan-1-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2H-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)−Acylnitrilium Ion Cyclizations

  摘要：

  2-Propylidene-1,3-bis(silane)s have been shown to be highly effective terminators in heteroannulations initiated by C-acylnitrilium ions. These cyclizations proceed under exceedingly mild reaction conditions with good to excellent levels of substrate-derived stereocontrol to provide the corresponding Delta(1)-pyrrolines possessing a functionalizable allylsilane moiety. Sequential reduction/N-tosylation of these products leads to the stereoselective formation of cis-pyrrolidine derivatives.

  DOI：

  10.1021/jo961452q
• 作为产物：
  描述：

  2-(1-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-isoindole-1,3-dione 在 一水合肼 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 N-(1-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-2-oxo-butyrimidoyl chloride
  参考文献：
  名称：

  Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2H-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)−Acylnitrilium Ion Cyclizations

  摘要：

  2-Propylidene-1,3-bis(silane)s have been shown to be highly effective terminators in heteroannulations initiated by C-acylnitrilium ions. These cyclizations proceed under exceedingly mild reaction conditions with good to excellent levels of substrate-derived stereocontrol to provide the corresponding Delta(1)-pyrrolines possessing a functionalizable allylsilane moiety. Sequential reduction/N-tosylation of these products leads to the stereoselective formation of cis-pyrrolidine derivatives.

  DOI：

  10.1021/jo961452q