N-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl]-3,3-dimethyl-2-oxo-butyrimidoyl chloride | 1027017-30-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl]-3,3-dimethyl-2-oxo-butyrimidoyl chloride
• CAS: 1027017-30-6
• 化学式: C₂₅H₅₂ClNO₂Si₃
• 分子量: 518.403
• InChiKey: GEIZFTAWTFFUSG-VYIQYICTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl]-3,3-dimethyl-2-oxo-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 1-[(2S,3S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(3-trimethylsilylprop-1-en-2-yl)pyrrolidin-2-yl]-2,2-dimethylpropan-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：

  4-[Tert-butyl(dimethyl)silyl]oxy-3-(1,3-dioxoisoindol-2-yl)butanal 在 bis-triphenylphosphine-palladium(II) chloride 一水合肼 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 16.75h， 生成 N-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl]-3,3-dimethyl-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