2-methylene-8-oxabicyclo[5.1.0]octane | 678144-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2-methylene-8-oxabicyclo[5.1.0]octane
• 英文别名: 3-methyliden-1,2-epoxycycloheptane；2-Methylidene-8-oxabicyclo[5.1.0]octane
• CAS: 678144-48-4
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: CBAVRRWSIYPGIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  171.8±19.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-环庚烯-1-酮 、 Dimethylzinc 、 2-methylene-8-oxabicyclo[5.1.0]octane 在 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 、 copper(II) bis(trifluoromethanesulfonate) 、 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (E)-2-((3-hydroxycyclohept-1-enyl)methyl)-3-methylcycloheptanone 、 (E)-2-((3-hydroxycyclohept-1-enyl)methyl)-3-methylcycloheptanone
  参考文献：
  名称：

  Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes

  摘要：

  An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cls/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.

  DOI：

  10.1021/ol9027682
• 作为产物：
  描述：

  2,3-epoxycycloheptanone 、 甲基三苯基溴化膦 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 以38%的产率得到2-methylene-8-oxabicyclo[5.1.0]octane
  参考文献：
  名称：

  Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes

  摘要：

  An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cls/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.

  DOI：

  10.1021/ol9027682

文献信息

• Catalytic Regiodivergent Kinetic Resolution of Allylic Epoxides:  A New Entry to Allylic and Homoallylic Alcohols with High Optical Purity
  作者：Mauro Pineschi、Federica Del Moro、Paolo Crotti、Valeria Di Bussolo、Franco Macchia

  DOI：10.1021/jo035674h

  日期：2004.3.1

  A novel regiodivergent kinetic resolution of a series of allylic epoxides with alkylzinc reagents is described. Results demonstrate the potential of chiral copper-phosphoramidite catalysts for enantiomer differentiation of allylic epoxides, allowing a chiral catalyst-stereoregulated synthesis of cyclic allylic and homoallylic alcohols with high optical purities.
• Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes
  作者：Matthias Welker、Simon Woodward、Alexandre Alexakis

  DOI：10.1021/ol9027682

  日期：2010.2.5

  An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cls/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.