[3,3-Dimethyl-4-vinyl-oxetan-(2Z)-ylidene]-(2,4,6-trimethyl-phenyl)-amine | 142980-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: [3,3-Dimethyl-4-vinyl-oxetan-(2Z)-ylidene]-(2,4,6-trimethyl-phenyl)-amine
• 英文别名: 4-ethenyl-3,3-dimethyl-N-(2,4,6-trimethylphenyl)oxetan-2-imine
• CAS: 142980-42-5
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: SBEVNDOLWXZSTR-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±52.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  [3,3-Dimethyl-4-vinyl-oxetan-(2Z)-ylidene]-(2,4,6-trimethyl-phenyl)-amine 在 二甲基亚砜 作用下， 反应 0.5h， 以70%的产率得到2,2-Dimethyl-3-oxo-pent-4-enoic acid (2,4,6-trimethyl-phenyl)-amide
  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

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.