nona-1,8-dien-5-one oxime | 171858-78-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: nona-1,8-dien-5-one oxime
• 英文别名: 1,8-Nonadien-5-one oxime；N-nona-1,8-dien-5-ylidenehydroxylamine
• CAS: 171858-78-9
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: MGTTWUFVZINHHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  nona-1,8-dien-5-one oxime 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 23.0h， 生成 trans-3,5-Dimethylhexahydropyrrolizine
  参考文献：
  名称：

  Reverse Cope elimination reactions. 2. Application to synthesis

  摘要：

  Intramolecular addition of N,N-disubstitute hydroxylamines to unactivated olefins was used to prepare an indolizine, a pyrrolo[2,1-a]isoquinoline, a 1,8-diazaspiro[4.5]decane, a cyclopenta[b]pyrrole, and an isoindoline. A pyrrolizine and a 1-azabicyclo[2.2.1] heptane were synthesized from acyclic precursors by two consecutive reverse Cope elimination reactions.

  DOI：

  10.1021/jo00123a014
• 作为产物：
  描述：

  nona-1,8-dien-5-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以97%的产率得到nona-1,8-dien-5-one oxime
  参考文献：
  名称：

  Reverse Cope elimination reactions. 2. Application to synthesis

  摘要：

  Intramolecular addition of N,N-disubstitute hydroxylamines to unactivated olefins was used to prepare an indolizine, a pyrrolo[2,1-a]isoquinoline, a 1,8-diazaspiro[4.5]decane, a cyclopenta[b]pyrrole, and an isoindoline. A pyrrolizine and a 1-azabicyclo[2.2.1] heptane were synthesized from acyclic precursors by two consecutive reverse Cope elimination reactions.

  DOI：

  10.1021/jo00123a014

文献信息

• Synthesis of Pyrrole Derivatives by Palladium-Catalyzed Cyclization of<i>γ</i>,<i>δ</i>-Unsaturated Ketone<i>O</i>-Pentafluorobenzoyloximes
  作者：Hironori Tsutsui、Mitsuru Kitamura、Koichi Narasaka

  DOI：10.1246/bcsj.75.1451

  日期：2002.7

  Various pyrrole derivatives are synthesized from γ,δ-unsaturated ketone O-pentafluorobenzoyloximes by treatment with catalytic amounts of Pd(PPh3)4 and triethylamine via alkylideneaminopalladium(II...

  通过用催化量的 Pd(PPh3)4 和三乙胺通过亚烷基氨基钯 (II...) 处理，从 γ,δ-不饱和酮 O-五氟苯甲酰肟合成各种吡咯衍生物。
• Chelating Diamide Based Rate Enhancement of Intramolecular Alkene Hydroaminations Catalyzed by a Neutral Sc(III) Complex
  作者：Joon Young Kim、Tom Livinghouse

  DOI：10.1021/ol051574h

  日期：2005.9.1

  [reaction: see text] Neutral scandium amido complexes are viable catalysts for intramolecular alkene hydroamination. Catalytic activity is strongly coupled to the electronic character of the Sc(III) ligand environment with chelating diamide coordination providing a precatalyst possessing substantially improved activity and superb distereoselectivity in the synthesis of trans-2,5-disubstituted pyrrolidines

  [反应：见正文]中性scan酰胺基络合物是分子内烯烃加氢胺化的可行催化剂。螯合二酰胺配位将催化活性与Sc（III）配体环境的电子特性紧密耦合，从而提供了一种在合成反式2,5-二取代的吡咯烷中具有显着提高的活性和极好的立体选择性的预催化剂。
• Reverse Cope elimination reactions. 2. Application to synthesis
  作者：Engelbert Ciganek

  DOI：10.1021/jo00123a014

  日期：1995.9

  Intramolecular addition of N,N-disubstitute hydroxylamines to unactivated olefins was used to prepare an indolizine, a pyrrolo[2,1-a]isoquinoline, a 1,8-diazaspiro[4.5]decane, a cyclopenta[b]pyrrole, and an isoindoline. A pyrrolizine and a 1-azabicyclo[2.2.1] heptane were synthesized from acyclic precursors by two consecutive reverse Cope elimination reactions.