diethyl 2-((E)-6-cyano-1-(trimethylsilyl)hex-1-en-3-yl)malonate | 1021541-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-((E)-6-cyano-1-(trimethylsilyl)hex-1-en-3-yl)malonate
• 英文别名: diethyl 2-[(E)-6-cyano-1-trimethylsilylhex-1-en-3-yl]propanedioate
• CAS: 1021541-71-8
• 化学式: C₁₇H₂₉NO₄Si
• 分子量: 339.507
• InChiKey: AVXLTEBURRHHEB-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-6-iodohex-5-enenitrile 、 丙二酸二乙酯 、 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65%的产率得到diethyl 2-((E)-6-cyano-1-(trimethylsilyl)hex-1-en-3-yl)malonate
  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.