Ethanone, 1-tricyclo[3.2.1.02,4]oct-6-en-3-yl-, (1alpha,2beta,3beta,4beta,5alpha)- (9CI) | 57220-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethanone, 1-tricyclo[3.2.1.02,4]oct-6-en-3-yl-, (1alpha,2beta,3beta,4beta,5alpha)- (9CI)
• 英文别名: 3-Acetyltricyclo<3.2.1.0^2,4>-6-octene；3-acetyltricyclo<3.2.1.0^2,4>oct-6-ene
• CAS: 57220-76-5；120663-38-9
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: UFPFWHDXZKMONU-NPLQXLRFSA-N

物化性质

• 沸点：
  224.9±29.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Ethanone, 1-tricyclo[3.2.1.02,4]oct-6-en-3-yl-, (1alpha,2beta,3beta,4beta,5alpha)- (9CI) 在 copper diacetate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-exo-acetyltricyclo[3.2.1.0^2,4]octane
  参考文献：
  名称：

  On an (oxatrimethylenemethane)palladium(0) complex. An unusual palladium(0)-catalyzed cyclopropanation

  摘要：

  DOI：

  10.1021/ja00194a043
• 作为产物：
  描述：

  ethyl-2-oxo-propyl carbonate 、 2,5-降冰片二烯 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 111.0h， 以69%的产率得到Ethanone, 1-tricyclo[3.2.1.02,4]oct-6-en-3-yl-, (1alpha,2beta,3beta,4beta,5alpha)- (9CI)
  参考文献：
  名称：

  Palladium-catalyzed reactions of ketone .alpha.-carbonates with norbornenes. An unusual cyclopropanation

  摘要：

  In the presence of a palladium(0) catalyst, ketone alpha-carbonates react with norbornene to give a cyclopropane derivative via an oxa-pi-allylpalladium intermediate.

  DOI：

  10.1021/jo00053a004

文献信息

• One-Step Synthesis of Oxodimethylenemethane−Transition Metal Complexes and Palladium-Catalyzed Cycloaddition Reaction
  作者：Isao Ikeda、Akihiro Ohsuka、Kazuyoshi Tani、Toshikazu Hirao、Hideo Kurosawa

  DOI：10.1021/jo951425k

  日期：1996.1.1

  Some alkyl allyl carbonates and an allylammonium chloride bearing (1-(butyloxy)ethyl)oxy group at the 2-position of the allyl group were synthesized and successfully transformed to oxodimethylenemethane-palladium and -platinum complexes in one step by mixing with a transition metal-(0) and triphenylphosphine. On the basis of the confirmation of vinyl ether formation by H-1 NMR, the generation of oxodimethylenemethane complexes was rationalized to occur through abstraction of the beta-hydrogen on the acetal carbon by an alkoxide ion which was generated from the allyl carbonate upon oxidative addition of the transition metal. The palladium-catalyzed cycloaddition of the acetonylidene group to strained olefins also proceeded successfully by using these alkyl allyl carbonates.