[3-(tert-butyldimethylsiloxy)propylamino]acetonitrile | 1236062-74-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [3-(tert-butyldimethylsiloxy)propylamino]acetonitrile
• 英文别名: 2-[3-[Tert-butyl(dimethyl)silyl]oxypropylamino]acetonitrile；2-[3-[tert-butyl(dimethyl)silyl]oxypropylamino]acetonitrile
• CAS: 1236062-74-0
• 化学式: C₁₁H₂₄N₂OSi
• 分子量: 228.41
• InChiKey: XIXROODPZCWZAE-UHFFFAOYSA-N

物化性质

• 沸点：
  301.0±22.0 °C(predicted)
• 密度：
  0.897±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  piperidin-1-yl(pyridin-3-yl)methanone 、 [3-(tert-butyldimethylsiloxy)propylamino]acetonitrile 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到2-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-1H-pyrrolo[3,4-c]pyridin-3-one
  参考文献：
  名称：

  Aminomethylation of lithiated nicotinamide: access to new pyridolactams

  摘要：

  New 2,3-dihydropyrrolopyridinones were conveniently prepared by trapping lithiated pyridine carboxamides, with highly reactive formimines. In this Letter, we report that a wide range of N-functionalised compounds can be synthesised in one step by this process, allowing the presence of ethers, acetals or ester moieties. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.109
• 作为产物：
  描述：

  3-(叔丁基二甲基甲硅烷基氧基)丙胺 、 氯乙腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以64%的产率得到[3-(tert-butyldimethylsiloxy)propylamino]acetonitrile
  参考文献：
  名称：

  Fully Substituted Carbon Centers by Diastereoselective Spirocyclization: Stereoselective Synthesis of (+)-Lepadiformine C

  摘要：

  Reductive lithiation of N-Boc alpha-amino nitriles generated alpha-amino alkyllithium reagents with unexpected selectivity. The intermediate radical prefers to align with the nitrogen lone pair, and this interaction leads to an A(1,3)-strain effect that biases the conformation of the radical. In cyclohexane rings with alpha-substituents the net effect is an inversion of configuration on reductive lithiation. In the presence of a tethered electrophile the alkyllithium cyclizes to produce a spiro compound, again with inversion of configuration. The overall result is retention of configuration in the cyclization reaction. The same overall selectivity is found with alpha-oxygen alkyllithium cyclizations, but in this case both steps proceed with retention. The difference can be explained by careful consideration of the intermediate geometries. The alpha-amino spirocyclization was utilized in a concise and stereoselective synthesis of lepadiformine C.

  DOI：

  10.1021/ja104250b

文献信息

• Fully Substituted Carbon Centers by Diastereoselective Spirocyclization: Stereoselective Synthesis of (+)-Lepadiformine C
  作者：Matthew A. Perry、Matthew D. Morin、Brian W. Slafer、Scott A. Wolckenhauer、Scott D. Rychnovsky

  DOI：10.1021/ja104250b

  日期：2010.7.21

  Reductive lithiation of N-Boc alpha-amino nitriles generated alpha-amino alkyllithium reagents with unexpected selectivity. The intermediate radical prefers to align with the nitrogen lone pair, and this interaction leads to an A(1,3)-strain effect that biases the conformation of the radical. In cyclohexane rings with alpha-substituents the net effect is an inversion of configuration on reductive lithiation. In the presence of a tethered electrophile the alkyllithium cyclizes to produce a spiro compound, again with inversion of configuration. The overall result is retention of configuration in the cyclization reaction. The same overall selectivity is found with alpha-oxygen alkyllithium cyclizations, but in this case both steps proceed with retention. The difference can be explained by careful consideration of the intermediate geometries. The alpha-amino spirocyclization was utilized in a concise and stereoselective synthesis of lepadiformine C.
• Aminomethylation of lithiated nicotinamide: access to new pyridolactams
  作者：Emilie Prieur、Rabah Azzouz、Geoffrey Deguest、Corinne Fruit、Laurent Bischoff、Francis Marsais

  DOI：10.1016/j.tetlet.2007.11.109

  日期：2008.1

  New 2,3-dihydropyrrolopyridinones were conveniently prepared by trapping lithiated pyridine carboxamides, with highly reactive formimines. In this Letter, we report that a wide range of N-functionalised compounds can be synthesised in one step by this process, allowing the presence of ethers, acetals or ester moieties. (C) 2007 Elsevier Ltd. All rights reserved.