5-Trimethylsilyl-4-(trimethylsilylmethyl)pent-3-en-1-amine | 176848-87-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 5-Trimethylsilyl-4-(trimethylsilylmethyl)pent-3-en-1-amine
• CAS: 176848-87-6
• 化学式: C₁₂H₂₉NSi₂
• 分子量: 243.54
• InChiKey: FERRPJJOVPYFJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Trimethylsilyl-4-(trimethylsilylmethyl)pent-3-en-1-amine 在 4 A molecular sieve 、 四氯化钛 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 trimethyl-[2-[(2S,3S)-2-(2-methylpropyl)pyrrolidin-3-yl]prop-2-enyl]silane
  参考文献：
  名称：

  Intramolecular 2-Propylidene-1,3-bis(silane) Imine Cyclizations. An Efficient New Procedure for the Stereocontrolled Synthesis of Pyrrolidines, Isotropanes, and Bridged Pyrrolizidines

  摘要：

  DOI：

  10.1021/ja954136m
• 作为产物：
  描述：

  2-[5-Trimethylsilyl-4-(trimethylsilylmethyl)pent-3-enyl]isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 以94%的产率得到5-Trimethylsilyl-4-(trimethylsilylmethyl)pent-3-en-1-amine
  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

• Intramolecular 2-Propylidene-1,3-bis(silane) Imine Cyclizations. An Efficient New Procedure for the Stereocontrolled Synthesis of Pyrrolidines, Isotropanes, and Bridged Pyrrolizidines
  作者：Timothy Kercher、Tom Livinghouse

  DOI：10.1021/ja954136m

  日期：1996.1.1
• 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.