2,2-dibut-3-enyl malonaldehyde | 333427-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dibut-3-enyl malonaldehyde
• 英文别名: 2,2-Bis(but-3-enyl)propanedial
• CAS: 333427-60-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ADOQYNSWEJUJFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dibut-3-enyl malonaldehyde 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 168.0h， 以9.93 g的产率得到2,2-dibut-3-enyl malonodioxime
  参考文献：
  名称：

  Design and Synthesis of the First Spiro Bis(isoxazoline) Derivatives as Asymmetric Ligands

  摘要：

  [GRAPHICS]A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition, The optically pure SPRIX greatly accelerated the Cu(acac)(2)-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.

  DOI：

  10.1021/ol9902881
• 作为产物：
  描述：

  2,2-di-but-3-enyl-malonic acid diethyl ester 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 生成 2,2-dibut-3-enyl malonaldehyde
  参考文献：
  名称：

  Spirocycle assembly through selective tandem ring closing metathesis reactions

  摘要：

  A range of functionalised spirocyclic systems have been prepared under mild and neutral conditions by tandem selective ring closing olefin metathesis reactions. Additionally, a marked preference for 5-membered ring closure over 7-membered ring closure was observed which appears to be a result of a kinetically favoured cyclisation process. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00375-5

文献信息

• Spirocycle assembly through selective tandem ring closing metathesis reactions
  作者：Martin J. Bassindale、Peter Hamley、Andreas Leitner、Joseph P.A. Harrity

  DOI：10.1016/s0040-4039(99)00375-5

  日期：1999.4

  A range of functionalised spirocyclic systems have been prepared under mild and neutral conditions by tandem selective ring closing olefin metathesis reactions. Additionally, a marked preference for 5-membered ring closure over 7-membered ring closure was observed which appears to be a result of a kinetically favoured cyclisation process. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Design and Synthesis of the First Spiro Bis(isoxazoline) Derivatives as Asymmetric Ligands
  作者：Midori A. Arai、Takayoshi Arai、Hiroaki Sasai

  DOI：10.1021/ol9902881

  日期：1999.12.1

  [GRAPHICS]A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition, The optically pure SPRIX greatly accelerated the Cu(acac)(2)-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.