N-(2-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-formamide | 1026876-00-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-formamide
• 英文别名: N-[2-methyl-5-trimethylsilyl-4-(trimethylsilylmethyl)pent-3-enyl]formamide
• CAS: 1026876-00-5
• 化学式: C₁₄H₃₁NOSi₂
• 分子量: 285.577
• InChiKey: LTKHMMDJDJJSLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-formamide 在 4-二甲氨基吡啶 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 38.0h， 生成 2,2-Dimethyl-1-[(2S,3R,4S)-4-methyl-1-(toluene-4-sulfonyl)-3-(1-trimethylsilanylmethyl-vinyl)-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：

  2-(4,4-Dibromo-2-methyl-but-3-enyl)-isoindole-1,3-dione 在 bis-triphenylphosphine-palladium(II) chloride 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.0h， 生成 N-(2-Methyl-5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-formamide
  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

文献信息

• Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2<i>H</i>-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)−Acylnitrilium Ion Cyclizations
  作者：Timothy Kercher、Tom Livinghouse

  DOI：10.1021/jo961452q

  日期：1997.2.1

  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.