[(3S,4R)-3-Methyl-4-phenyl-3-vinyl-oxetan-(2Z)-ylidene]-p-tolyl-amine | 116749-14-5

• 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: [(3S,4R)-3-Methyl-4-phenyl-3-vinyl-oxetan-(2Z)-ylidene]-p-tolyl-amine
• 英文别名: (3S,4R)-3-ethenyl-3-methyl-N-(4-methylphenyl)-4-phenyloxetan-2-imine
• CAS: 116749-14-5
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: LTEUOFIJHCQVFS-MJGOQNOKSA-N

物化性质

• 沸点：
  392.2±52.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(3S,4R)-3-Methyl-4-phenyl-3-vinyl-oxetan-(2Z)-ylidene]-p-tolyl-amine 在 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium 作用下， 反应 0.42h， 以30%的产率得到cis-4-Phenyl-3-methyl-3-vinyl-1-p-tolylazetidin-2-one
  参考文献：
  名称：

  Lanthanide- and DMSO-Induced Ring Opening of 2-Iminooxetanes: Synthesis of .beta.-Lactams and .beta.-Keto Amides

  摘要：

  2-Iminooxetanes (1), generated by lanthanide-catalyzed heterocycloaddition of aldehydes to ketene imines, are versatile synthons for beta-lactams (2) and for beta-keto amides (3). Conversion of 1 into 2 and 3 can be accomplished by either lanthanide-induced or oxidative (DMSO) ring opening, respectively.

  DOI：

  10.1021/jo00109a038
• 作为产物：
  描述：

  methylvinylketene N-p-tolylimine 、 苯甲醛 在 Yb(hfc)3(+) 作用下， 以 四氯化碳 为溶剂， 反应 48.0h， 以16%的产率得到[(3S,4S)-3-Methyl-4-phenyl-3-vinyl-oxetan-(2Z)-ylidene]-p-tolyl-amine
  参考文献：
  名称：

  2-Iminooxetane chemistry. 2. General synthesis from ketene imine-aldehyde cycloadditions

  摘要：

  DOI：

  10.1021/jo00258a019

文献信息

• 2-Iminooxetane chemistry. 3. Synthesis of .beta.-hydroxy amides
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00045a024

  日期：1992.9

  Beta-Hydroxy amides were synthesized by hydrolysis of the corresponding 2-iminooxetanes, which were prepared in a very simple step by lanthanide-catalyzed cycloaddition of aldehydes to ketene imines. The stereochemical outcome of the hydrolysis, performed under neutral (DMSO/H2O) or acidic (H2SO4/H2O) conditions, depends on the steric and electronic nature of the substituents, which play a crucial role in the ring-opening mechanism. Experiments done with O-18-labeled water showed that two alternatives are possible: one involving ring opening of the oxetane at the C4-O bond, the other involving ring opening at the C2-O bond.
• 2-Iminooxetane chemistry. 2. General synthesis from ketene imine-aldehyde cycloadditions
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00258a019

  日期：1988.11
• Lanthanide- and DMSO-Induced Ring Opening of 2-Iminooxetanes: Synthesis of .beta.-Lactams and .beta.-Keto Amides
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00109a038

  日期：1995.2

  2-Iminooxetanes (1), generated by lanthanide-catalyzed heterocycloaddition of aldehydes to ketene imines, are versatile synthons for beta-lactams (2) and for beta-keto amides (3). Conversion of 1 into 2 and 3 can be accomplished by either lanthanide-induced or oxidative (DMSO) ring opening, respectively.