(1E,6E)-2-Ethyl-7-phenyl-1-(trimethylsilyl)hepta-1,6-diene

• 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: (1E,6E)-2-Ethyl-7-phenyl-1-(trimethylsilyl)hepta-1,6-diene
• 英文别名: [(1E,6E)-2-ethyl-7-phenylhepta-1,6-dienyl]-trimethylsilane
• 化学式: C₁₈H₂₈Si
• 分子量: 272.506
• InChiKey: ZZZDNWBCLQNNJP-YDNXFKBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  碘代三甲硅烷 、 diethylzinc 、 (E)-hept-1-en-6-yn-1-ylbenzene 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 1.0h， 以79%的产率得到(1E,6E)-2-Ethyl-7-phenyl-1-(trimethylsilyl)hepta-1,6-diene
  参考文献：
  名称：

  Pd-Catalyzed Coupling Reaction of Acetylenes, Iodotrimethylsilane, and Organozinc Reagents for the Stereoselective Synthesis of Vinylsilanes

  摘要：

  The reaction of terminal acetylenes with Me(3)SiI (1) and organozinc reagents in the presence of Pd(PPh(3))(4) results in addition of the trimethylsilyl group of 1 and an alkyl group of the organozinc reagent to the acetylenes. In all cases the trimethylsilyl group adds to the terminal carbon of the acetylenes. Both aromatic and aliphatic terminal acetylenes undergo the coupling reaction with high regio- and stereoselectivities. The yield and stereoselectivity are relatively sensitive to the nature of the organozinc reagent used. The reaction of phenylacetylene (2) using Bu(2)Zn gives the corresponding coupling product in high yield with high stereoselectivity (>98%). In contrast, the use of BuZnI results in 92% stereoselectivity. The stereoselectivity for the reaction using (Me(3)-SiCH2)(2)Zn is lower than those for Me(2)Zn, Et(2)Zn, and Bu(2)Zn. For organozinc reagents, alkylzinc works well while phenyl-, ethynyl-, and allylzinc do not. The reaction using Me(3)SiCl, Me(3)SiBr, Me(3)SiSPh, Me(3)SiSePh, and Me(3)SiOTf in place of 1 does not proceed. The reaction with Me(3)SiMe(2)-SiI and Me(3)SiMe(2)SiMe(2)SiI in place of 1 gives the corresponding vinyldisilane and -trisilane, respectively.

  DOI：

  10.1021/jo00111a048

文献信息

• Pd-Catalyzed Coupling Reaction of Acetylenes, Iodotrimethylsilane, and Organozinc Reagents for the Stereoselective Synthesis of Vinylsilanes
  作者：Naoto Chatani、Nobuyoshi Amishiro、Takaya Morii、Toshiaki Yamashita、Shinji Murai

  DOI：10.1021/jo00111a048

  日期：1995.3

  The reaction of terminal acetylenes with Me(3)SiI (1) and organozinc reagents in the presence of Pd(PPh(3))(4) results in addition of the trimethylsilyl group of 1 and an alkyl group of the organozinc reagent to the acetylenes. In all cases the trimethylsilyl group adds to the terminal carbon of the acetylenes. Both aromatic and aliphatic terminal acetylenes undergo the coupling reaction with high regio- and stereoselectivities. The yield and stereoselectivity are relatively sensitive to the nature of the organozinc reagent used. The reaction of phenylacetylene (2) using Bu(2)Zn gives the corresponding coupling product in high yield with high stereoselectivity (>98%). In contrast, the use of BuZnI results in 92% stereoselectivity. The stereoselectivity for the reaction using (Me(3)-SiCH2)(2)Zn is lower than those for Me(2)Zn, Et(2)Zn, and Bu(2)Zn. For organozinc reagents, alkylzinc works well while phenyl-, ethynyl-, and allylzinc do not. The reaction using Me(3)SiCl, Me(3)SiBr, Me(3)SiSPh, Me(3)SiSePh, and Me(3)SiOTf in place of 1 does not proceed. The reaction with Me(3)SiMe(2)-SiI and Me(3)SiMe(2)SiMe(2)SiI in place of 1 gives the corresponding vinyldisilane and -trisilane, respectively.