N-Benzyl-N-(2-cyclohexen-1-yl)(3-(trimethylsilyl)-2-propynyl)amine | 141526-49-0

• 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: N-Benzyl-N-(2-cyclohexen-1-yl)(3-(trimethylsilyl)-2-propynyl)amine
• 英文别名: N-benzyl-N-(3-trimethylsilylprop-2-ynyl)cyclohex-2-en-1-amine
• CAS: 141526-49-0
• 化学式: C₁₉H₂₇NSi
• 分子量: 297.516
• InChiKey: AANPIJZLGUNZQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  N-Benzyl-N-(2-cyclohexen-1-yl)(3-(trimethylsilyl)-2-propynyl)amine 在 盐酸 、 正丁基锂 、 二氯二茂锆 作用下， 生成 (3aR*,7aR*)-1-Benzyl-3-((Z)-(trimethylsilyl)methylene)perhydroindole
  参考文献：
  名称：

  Novel synthesis of nitrogen heterocycles using zirconium-promoted reductive coupling. Formal total synthesis of dendrobine

  摘要：

  A novel synthesis of nitrogen heterocycles by means of a zirconium-promoted, intramolecular reductive coupling reaction of an enyne or a diene was developed, and the formal total synthesis of dendrobine from (-)-carvone was achieved by a short sequence of steps.

  DOI：

  10.1021/jo00039a001
• 作为产物：
  描述：

  N-benzyl-N-(2-cyclohexenyl)amine 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 33.67h， 生成 N-Benzyl-N-(2-cyclohexen-1-yl)(3-(trimethylsilyl)-2-propynyl)amine
  参考文献：
  名称：

  Novel Synthesis of Nitrogen Heterocycles Using Zirconium-Promoted Reductive Cyclization

  摘要：

  Perhydroindole derivatives were prepared from enynes using zirconium-promoted reductive cyclization. The zirconacycles derived from enynes 1 were treated with iodine, isonitriles, oxygen, and carbon monoxide to give various heterocycles. The carbon-zirconium bonds of the zirconacycle could be selectively cleaved by different reagents.

  DOI：

  10.1021/jo00098a023

文献信息

• Novel synthesis of nitrogen heterocycles using zirconium-promoted reductive coupling. Formal total synthesis of dendrobine
  作者：Miwako Mori、Noriaki Uesaka、Masakatsu Shibasaki

  DOI：10.1021/jo00039a001

  日期：1992.6

  A novel synthesis of nitrogen heterocycles by means of a zirconium-promoted, intramolecular reductive coupling reaction of an enyne or a diene was developed, and the formal total synthesis of dendrobine from (-)-carvone was achieved by a short sequence of steps.
• Novel Synthesis of Nitrogen Heterocycles Using Zirconium-Promoted Reductive Cyclization
  作者：Miwako Mori、Noriaki Uesaka、Fumihiko Saitoh、Masakatsu Shibasaki

  DOI：10.1021/jo00098a023

  日期：1994.9

  Perhydroindole derivatives were prepared from enynes using zirconium-promoted reductive cyclization. The zirconacycles derived from enynes 1 were treated with iodine, isonitriles, oxygen, and carbon monoxide to give various heterocycles. The carbon-zirconium bonds of the zirconacycle could be selectively cleaved by different reagents.