(E)-3-tributylstannyl-1,1-diethoxybut-2-ene | 848230-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-tributylstannyl-1,1-diethoxybut-2-ene
• CAS: 848230-22-8
• 化学式: C₂₀H₄₂O₂Sn
• 分子量: 433.262
• InChiKey: OFPANOLHIUFPQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-tributylstannyl-1,1-diethoxybut-2-ene 、 (三甲基硅基)甲基氯化镁 在 三氟化硼乙醚 、 copper(l) cyanide 作用下， 以 乙醚 为溶剂， 生成 (Z)-3-tributylstannyl-1-ethoxy-3-(trimethylsilylmethyl)but-1-ene 、 (E)-3-tributylstannyl-1-ethoxy-3-(trimethylsilylmethyl)but-1-ene 、 (E)-2-tributylstannyl-4-ethoxy-5-trimethylsilylpent-2-ene
  参考文献：
  名称：

  Preparation of α-substituted γ-alkoxyallylstannanes from β-tributylstannyl acrolein acetals: scope of the method and primary rationalization of the obtained results

  摘要：

  alpha-Substituted gamma-alkoxyallylstannanes were obtained from beta-tributylstannyl acrolein acetals when reacted with lower order magnesium cyanocuprates in the presence of boron trifluoride at low temperature. In the case of n-alkylcyanocuprates an anti S(N)2' substitution on a cisoid conformation appears to be the main reaction pathway. However, subtle competitions with other mechanisms may occur depending on the experimental conditions, on the reagents or on the substrates. These drawbacks constitute limitations for the use of the method especially when enantioenriched alpha-substituted gamma-alkoxyallylstannanes are desired. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.10.022

文献信息

• Preparation of α-substituted γ-alkoxyallylstannanes from β-tributylstannyl acrolein acetals: scope of the method and primary rationalization of the obtained results
  作者：Florian Fliegel、Isabelle Beaudet、Sandrine Watrelot-Bourdeau、Nicolas Cornet、Jean-Paul Quintard

  DOI：10.1016/j.jorganchem.2004.10.022

  日期：2005.1

  alpha-Substituted gamma-alkoxyallylstannanes were obtained from beta-tributylstannyl acrolein acetals when reacted with lower order magnesium cyanocuprates in the presence of boron trifluoride at low temperature. In the case of n-alkylcyanocuprates an anti S(N)2' substitution on a cisoid conformation appears to be the main reaction pathway. However, subtle competitions with other mechanisms may occur depending on the experimental conditions, on the reagents or on the substrates. These drawbacks constitute limitations for the use of the method especially when enantioenriched alpha-substituted gamma-alkoxyallylstannanes are desired. (C) 2004 Elsevier B.V. All rights reserved.