3,3-Dimethyl-2-oxo-N-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-butyrimidoyl chloride | 1027285-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-Dimethyl-2-oxo-N-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-butyrimidoyl chloride
• CAS: 1027285-86-4
• 化学式: C₁₈H₃₆ClNOSi₂
• 分子量: 374.114
• InChiKey: WXVFDSBRZKTFSK-JZJYNLBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  3,3-Dimethyl-2-oxo-N-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-butyrimidoyl chloride 在 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 9.0h， 生成 2,2-dimethyl-1-[3-(3-trimethylsilylprop-1-en-2-yl)pyrrolidin-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：

  N-[5-trimethylsilyl-4-(trimethylsilylmethyl)pent-3-enyl]formamide 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 3,3-Dimethyl-2-oxo-N-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-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