N-烯丙基-N-苄基-N-(2-环己烯-1-基)胺 | 141508-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-烯丙基-N-苄基-N-(2-环己烯-1-基)胺
• 英文名称: N-allyl-N-benzyl-N-(2-cyclohexen-1-yl)amine
• 英文别名: N-benzyl-N-prop-2-enylcyclohex-2-en-1-amine
• CAS: 141508-33-0
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: CVCWVQZPRKTVNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-烯丙基-N-苄基-N-(2-环己烯-1-基)胺 在 palladium on activated charcoal 、 二氯二茂锆 盐酸 、 溴丁基-镁 、 4-二甲氨基吡啶 、 dibutylbis(cyclopentadienyl)zirconium 、 氢气 、 potassium carbonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 44.5h， 生成 (1S*,3S*,4R*,8R*,11R*)-3-Ethyl-9-tosyl-9-azatricyclo<6.2.1.0^4,11>undecane
  参考文献：
  名称：

  Novel Synthesis of Heterocycles Using Zirconium-Catalyzed Diene Cyclization

  摘要：

  The catalytic cyclization of the diene 1 by Cp(2)ZrCl(2) in the presence of BuMgBr gives the hexahydroindole derivative 2. The stereochemistry of the zirconacycle 10 is different from that of the zirconacycle 7, which is obtained from 1 under stoichiometric conditions. Carbon-carbon bond formation results from treatment of the intermediary magnesium complex 8 with various electrophiles, such that various heterocycles were synthesized.

  DOI：

  10.1021/jo00095a032

文献信息

• The Regiochemistry of Carbenoid Insertion into Zirconacycles
  作者：George J. Gordon、Tim Luker、Mark W. Tuckett、Richard J. Whitby

  DOI：10.1016/s0040-4020(99)01094-7

  日期：2000.4

  lithium chloroallylides (allyl carbenoids) into a wide variety of unsymmetrical zirconacycles has been determined. In all but one case a single regioisomer was obtained. A combination of steric and electronic effects is needed to explain the results and imply that the carbenoid is acting predominantly as an electrophilic species. The first carbenoid insertion into a zirconacyclopentadiene is noted.

  已经确定了将氯代烯丙基锂（烯丙基类胡萝卜素）插入各种各样的不对称氧化锆环中的区域选择性。除一种情况外，在所有情况下均获得单一的区域异构体。需要结合空间和电子效应来解释结果，并暗示类胡萝卜素主要起亲电物质的作用。注意到第一次类胡萝卜素插入到氧化锆环戊二烯中。
• Syntheses and X-Ray Crystal Structures of Tricyclic Ketones Containing Trans-Fused Azabicyclo[3.3.0]octane Units
  作者：Miwako Mori、Fumihiko Saitoh、Noriaki Uesaka、Kimio Okamura、Tadamasa Date

  DOI：10.1021/jo00096a050

  日期：1994.8

  Tricyclic ketones containing the trans-fused 3-azabicyclo[3.3.0]octane framework were prepared from the reactions of dienes and Cp(2)ZrBu(2), followed by treatment with carbon monoxide. The structures were confirmed by X-ray analysis.
• 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 Quinoline Derivatives by Zirconium-Promoted Cyclization
  作者：Miwako Mori、Alice Emi Imai、Noriaki Uesaka

  DOI：10.3987/com-94-s84

  日期：——

  Zirconium-promoted cyclization of the diene (1) resulted in the perhydroquinoline derivatives (2a) and (3a) in moderate yields. The intermediary zirconacycles can be converted into the iodinated products (2c) and (3c) by treatment with iodine, and into the tricyclic ketones (12) by treatment with carbon monoxide.
• Novel Synthesis of Heterocycles Using Zirconium-Catalyzed Diene Cyclization
  作者：Noriaki Uesaka、Miwako Mori、Kimio Okamura、Tadamasa Date

  DOI：10.1021/jo00095a032

  日期：1994.8

  The catalytic cyclization of the diene 1 by Cp(2)ZrCl(2) in the presence of BuMgBr gives the hexahydroindole derivative 2. The stereochemistry of the zirconacycle 10 is different from that of the zirconacycle 7, which is obtained from 1 under stoichiometric conditions. Carbon-carbon bond formation results from treatment of the intermediary magnesium complex 8 with various electrophiles, such that various heterocycles were synthesized.