1-((E)-3-methyl-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)piperidine | 940310-15-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-((E)-3-methyl-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)piperidine
• 英文别名: trimethyl-[(E)-3-methyl-5-phenyl-3-piperidin-1-ylpent-1-enyl]silane
• CAS: 940310-15-6
• 化学式: C₂₀H₃₃NSi
• 分子量: 315.574
• InChiKey: WCCJOSAFYKDCGD-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((E)-3-methyl-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)piperidine 在 盐酸 作用下， 反应 14.0h， 以96%的产率得到1-(3-methyl-5-phenylpent-1-en-3-yl)piperidine
  参考文献：
  名称：

  Palladium-Catalyzed Carbene Insertion into Vinyl Halides and Trapping with Amines

  摘要：

  Palladium is shown to catalyze the three- component coupling of vinyl halides, trimethylsilyldiazomethane, and amines to generate allylamines. The mechanism is believed to involve formation of an R-Pd=CHSiMe3 intermediate that undergoes migration of the vinyl ligand to the empty p-orbital of the carbene ligand. The resulting eta(1)-allylpalladium species forms an eta(3)-allylpalladium intermediate that is trapped by the amine nucleophile. Under the conditions tested, cyclic secondary amines and terminal vinyl iodides give the best results.

  DOI：

  10.1021/ol070758o
• 作为产物：
  描述：

  4-苯基-1-丁炔 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 1-((E)-3-methyl-1-(trimethylsilyl)-5-phenylpent-1-en-3-yl)piperidine
  参考文献：
  名称：

  Palladium-Catalyzed Carbene Insertion into Vinyl Halides and Trapping with Amines

  摘要：

  Palladium is shown to catalyze the three- component coupling of vinyl halides, trimethylsilyldiazomethane, and amines to generate allylamines. The mechanism is believed to involve formation of an R-Pd=CHSiMe3 intermediate that undergoes migration of the vinyl ligand to the empty p-orbital of the carbene ligand. The resulting eta(1)-allylpalladium species forms an eta(3)-allylpalladium intermediate that is trapped by the amine nucleophile. Under the conditions tested, cyclic secondary amines and terminal vinyl iodides give the best results.

  DOI：

  10.1021/ol070758o

文献信息

• Palladium-Catalyzed Carbene Insertion into Vinyl Halides and Trapping with Amines
  作者：Sean K. J. Devine、David L. Van Vranken

  DOI：10.1021/ol070758o

  日期：2007.5.1

  Palladium is shown to catalyze the three- component coupling of vinyl halides, trimethylsilyldiazomethane, and amines to generate allylamines. The mechanism is believed to involve formation of an R-Pd=CHSiMe3 intermediate that undergoes migration of the vinyl ligand to the empty p-orbital of the carbene ligand. The resulting eta(1)-allylpalladium species forms an eta(3)-allylpalladium intermediate that is trapped by the amine nucleophile. Under the conditions tested, cyclic secondary amines and terminal vinyl iodides give the best results.