pyrrolidinyldiethylsilane | 55552-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: pyrrolidinyldiethylsilane
• 英文别名: pyrrolidinodiethylsilane；Diethyl(pyrrolidin-1-yl)silane
• CAS: 55552-54-0
• 化学式: C₈H₁₉NSi
• 分子量: 157.331
• InChiKey: DAMJZHFTOXVCFX-UHFFFAOYSA-N

物化性质

• 沸点：
  66.8±8.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  pyrrolidinyldiethylsilane 在 盐酸 、 碳酸氢钠 作用下， 以 乙醚 、 甲醇 、 水 为溶剂， 反应 3.0h， 以90%的产率得到吡咯烷盐酸盐
  参考文献：
  名称：

  Iridium-Catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane

  摘要：

  Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE)(2)Cl](2) with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.

  DOI：

  10.1021/ja304547s
• 作为产物：
  描述：

  2-吡咯烷酮 在 chlorobis(cyclooctene)-iridium(I) dimer 、 二乙基硅烷 作用下， 反应 12.0h， 生成 pyrrolidinyldiethylsilane
  参考文献：
  名称：

  Iridium-Catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane

  摘要：

  Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE)(2)Cl](2) with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.

  DOI：

  10.1021/ja304547s

文献信息

• Selective catalytic synthesis of amino-silanes at part-per million catalyst loadings
  作者：Pablo Ríos、Marta Roselló-Merino、Orestes Rivada-Wheelaghan、Javier Borge、Joaquín López-Serrano、Salvador Conejero

  DOI：10.1039/c7cc08530c

  日期：——

  Platinum(ii) complex [Pt(I^tBu′)(I^tBu)][BAr^F₄] (1a) is a highly active and selective catalyst in the dehydrocoupling of amines and silanes at part-per-million catalyst loadings (up to 10 ppm, 0.001 mol%), achieving the highest TON and TOF numbers reported in the literature (up to 1 mmol scale).

  白金（II）配合物[Pt(I^tBu')(I^tBu)][BAr^F_4]（1a）是一种在亚百万催化剂负载下（最多达到10 ppm，0.001 mol％）对胺和硅烷进行脱氢偶联的高活性和选择性催化剂，在文献中报告的TOM和TOF数值最高（最多达到1 mmol尺度）。