2-((E)-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)malononitrile | 1021541-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((E)-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)malononitrile
• 英文别名: 2-[(E)-5-phenyl-1-trimethylsilylpent-1-en-3-yl]propanedinitrile
• CAS: 1021541-77-4
• 化学式: C₁₇H₂₂N₂Si
• 分子量: 282.461
• InChiKey: NOHJZEOHEXLKER-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((E)-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)malononitrile 在 溴 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 生成 2-((Z)-1-bromo-5-phenylpent-1-en-3-yl)malononitrile 、 2-((E)-1-bromo-5-phenylpent-1-en-3-yl)malononitrile
  参考文献：
  名称：

  Palladium-Catalyzed Carbene Insertion and Trapping with Carbon Nucleophiles

  摘要：

  Palladium catalysts are shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and stabilized carbon nucleophiles. The reaction is believed to proceed through a palladium-carbene intermediate LX(R)Pd=CHSiMe3 that undergoes migration of the vinyl substituent to the electrophilic carbene center to generate an eta(3)-allylpalladium intermediate. The allylpalladium intermediate is attacked by the carbon nucleophile to generate a vinylsilane product.

  DOI：

  10.1021/ol800431w
• 作为产物：
  描述：

  (Z)-(4-iodobut-3-en-1-yl)benzene 、 丙二腈 、 三甲基硅烷化重氮甲烷 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.0h， 以61%的产率得到2-((E)-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)malononitrile
  参考文献：
  名称：

  Palladium-Catalyzed Carbene Insertion and Trapping with Carbon Nucleophiles

  摘要：

  Palladium catalysts are shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and stabilized carbon nucleophiles. The reaction is believed to proceed through a palladium-carbene intermediate LX(R)Pd=CHSiMe3 that undergoes migration of the vinyl substituent to the electrophilic carbene center to generate an eta(3)-allylpalladium intermediate. The allylpalladium intermediate is attacked by the carbon nucleophile to generate a vinylsilane product.

  DOI：

  10.1021/ol800431w

文献信息

• Palladium-Catalyzed Carbene Insertion and Trapping with Carbon Nucleophiles
  作者：Sean K. J. Devine、David L. Van Vranken

  DOI：10.1021/ol800431w

  日期：2008.5.1

  Palladium catalysts are shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and stabilized carbon nucleophiles. The reaction is believed to proceed through a palladium-carbene intermediate LX(R)Pd=CHSiMe3 that undergoes migration of the vinyl substituent to the electrophilic carbene center to generate an eta(3)-allylpalladium intermediate. The allylpalladium intermediate is attacked by the carbon nucleophile to generate a vinylsilane product.