2-(1-Butoxyethoxy)prop-2-enyl methyl carbonate | 178918-51-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2-(1-Butoxyethoxy)prop-2-enyl methyl carbonate
• CAS: 178918-51-9
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: SHRHQWXIPFWVAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  降冰片烯 、 2-(1-Butoxyethoxy)prop-2-enyl methyl carbonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到3-exo-acetyltricyclo[3.2.1.0^2,4]octane
  参考文献：
  名称：

  One-Step Synthesis of Oxodimethylenemethane−Transition Metal Complexes and Palladium-Catalyzed Cycloaddition Reaction

  摘要：

  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.

  DOI：

  10.1021/jo951425k
• 作为产物：
  描述：

  2-(1-Butoxyethoxy)prop-2-enyl acetate 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 吡啶 、 水 、 苯 为溶剂， 反应 1.08h， 生成 2-(1-Butoxyethoxy)prop-2-enyl methyl carbonate
  参考文献：
  名称：

  One-Step Synthesis of Oxodimethylenemethane−Transition Metal Complexes and Palladium-Catalyzed Cycloaddition Reaction

  摘要：

  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.

  DOI：

  10.1021/jo951425k

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.