Ethyl 2-formyl(9-fluorenyliden)acetate | 139286-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Ethyl 2-formyl(9-fluorenyliden)acetate
• 英文别名: ethyl 2-fluoren-9-ylidene-3-oxopropanoate
• CAS: 139286-79-6
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: PDZMVRGCMYYRLV-UHFFFAOYSA-N

物化性质

• 沸点：
  473.5±33.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-phenyl-fluorenoneimine-N-oxide 以 四氢呋喃 为溶剂， 反应 51.0h， 生成 Ethyl 2-formyl(9-fluorenyliden)acetate
  参考文献：
  名称：

  Novel approach to the ring-opening of 4-isoxazolines: One-pot synthesis of α,β-enones

  摘要：

  Treatment of 4-isoxazoline derivatives with methyl iodide affords alpha-beta-enones in excellent yields. The novel rearrangement pathway, proceeding through an intermediate isoxazolinium salt, is interpretable on the basis of the base removal of the hydrogen atom at N-CH3 group.

  DOI：

  10.1016/s0040-4020(01)80585-8

文献信息

• New Rearrangement of 4-Isoxazoline System:  Conversion of Ketones into α,β-Unsaturated Amides
  作者：Ugo Chiacchio、Antonio Rescifina、Maria Assunta Chiacchio、Giovanni Romeo、Roberto Romeo

  DOI：10.1021/jo034135+

  日期：2003.5.1

  A new rearrangement pattern of the 4-isoxazoline system is reported. The reaction, starting from 3,3-disubstituted derivatives and leading to alpha,beta-unsaturated amides, proceeds through the quaternarization of the nitrogen atom and involves the heterolytic cleavage of C(3)-N bond, assisted by the formation of a relatively stable intermediate. The overall process represents a useful conversion of

  报道了4-异恶唑啉系统的新的重排模式。该反应从3,3-二取代的衍生物开始并导致α，β-不饱和酰胺，通过氮原子的季铵化反应进行，并涉及C（3）-N键的杂化裂解，并通过形成相对稳定的中间体。整个过程代表了将酮有效转化为α，β-不饱和酰胺的过程。
• Novel approach to the ring-opening of 4-isoxazolines: One-pot synthesis of α,β-enones
  作者：Ugo Chiachio、Angelo Liguori、Antonio Rescifina、Giovanni Romeo、Flavia Rossano、Giovanni Sindona、Nicola Uccella

  DOI：10.1016/s0040-4020(01)80585-8

  日期：1992.1

  Treatment of 4-isoxazoline derivatives with methyl iodide affords alpha-beta-enones in excellent yields. The novel rearrangement pathway, proceeding through an intermediate isoxazolinium salt, is interpretable on the basis of the base removal of the hydrogen atom at N-CH3 group.