(E)-2-[tert-butyl(dimethyl)silyl]oxy-N-trimethylsilylpropan-1-imine | 116102-34-2

• 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: (E)-2-[tert-butyl(dimethyl)silyl]oxy-N-trimethylsilylpropan-1-imine
• CAS: 116102-34-2；139111-00-5；146405-38-1
• 化学式: C₁₂H₂₉NOSi₂
• 分子量: 259.539
• InChiKey: IHDJKGQRNZTCAN-JLHYYAGUSA-N

物化性质

• 沸点：
  254.9±42.0 °C(Predicted)
• 密度：
  0.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-[tert-butyl(dimethyl)silyl]oxy-N-trimethylsilylpropan-1-imine 在 ammonium hydroxide 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 生成 {(1S,2S)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-trimethylsilanylethynyl-pentyl}-[1-phenyl-meth-(E)-ylidene]-amine
  参考文献：
  名称：

  Comparative Study of the Diastereoselective Addition of Allenyl Zinc Reagents to α-Alkoxy (or Silyloxy) Aldehydes and Imines. A Straightforward Synthesis of Amino Alcohols from Imines

  摘要：

  The addition of allenylzine bromides to or-chiral imines proceeds with very high diastereoselectivity. This result is in contrast with the addition to the corresponding aldehydes, leading to poor diastereoselectivity. The anti/anti adducts are explained by Felkin-Ahn and Gaudemar-Yamamoto models of the transition state.

  DOI：

  10.1021/jo005509r
• 作为产物：
  描述：

  2-tert-butyldimethylsilyloxypropanal 、 lithium hexamethyldisilazane 以 四氢呋喃 为溶剂， 生成 (E)-2-[tert-butyl(dimethyl)silyl]oxy-N-trimethylsilylpropan-1-imine
  参考文献：
  名称：

  Comparative Study of the Diastereoselective Addition of Allenyl Zinc Reagents to α-Alkoxy (or Silyloxy) Aldehydes and Imines. A Straightforward Synthesis of Amino Alcohols from Imines

  摘要：

  The addition of allenylzine bromides to or-chiral imines proceeds with very high diastereoselectivity. This result is in contrast with the addition to the corresponding aldehydes, leading to poor diastereoselectivity. The anti/anti adducts are explained by Felkin-Ahn and Gaudemar-Yamamoto models of the transition state.

  DOI：

  10.1021/jo005509r

文献信息

• Reversal of diastereoselectivity in the addition of C-nucleophiles to N-trimethylsilyl imines via Grignard derived organo copper-boron trifluoride reagents.
  作者：Gianfranco Cainelli、Daria Giacomini、Mauro Panunzio、Paola Zarantonello

  DOI：10.1016/0040-4039(93)88045-k

  日期：1992.12

  The N-trimethylsilyl imines of O-protected alpha-hydroxy aldehydes react with RCuMgXI BF3 to give beta-amino alcohols with high anti diastereoselectivity.
• Comparative Study of the Diastereoselective Addition of Allenyl Zinc Reagents to α-Alkoxy (or Silyloxy) Aldehydes and Imines. A Straightforward Synthesis of Amino Alcohols from Imines
  作者：Jean-François Poisson、Jean F. Normant

  DOI：10.1021/jo005509r

  日期：2000.10.1

  The addition of allenylzine bromides to or-chiral imines proceeds with very high diastereoselectivity. This result is in contrast with the addition to the corresponding aldehydes, leading to poor diastereoselectivity. The anti/anti adducts are explained by Felkin-Ahn and Gaudemar-Yamamoto models of the transition state.