1-Methyl-2,3-dimethylene-cyclobutanecarbonitrile | 153339-06-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Methyl-2,3-dimethylene-cyclobutanecarbonitrile
• 英文别名: 1-Methyl-2,3-dimethylenecyclobutanecarbonitrile；1-methyl-2,3-dimethylidenecyclobutane-1-carbonitrile
• CAS: 153339-06-1
• 化学式: C₈H₉N
• 分子量: 119.166
• InChiKey: UGVSIDDDRRCUEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-二溴-3-戊酮 、 1-Methyl-2,3-dimethylene-cyclobutanecarbonitrile 在 diiron nonacarbonyl 作用下， 以 苯 为溶剂， 反应 1.5h， 以65%的产率得到3,5,8-Trimethyl-4-oxo-bicyclo[5.2.0]non-1(7)-ene-8-carbonitrile
  参考文献：
  名称：

  New access to Di-exo-methylenecyclobutanes via [2 + 2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid

  摘要：

  Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.

  DOI：

  10.1016/s0040-4039(00)61469-7
• 作为产物：
  描述：

  2-Methanesulfonyl-1-methyl-3-methylene-2-trimethylsilanylmethyl-cyclobutanecarbonitrile 在 四氯化钛 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到1-Methyl-2,3-dimethylene-cyclobutanecarbonitrile
  参考文献：
  名称：

  New access to Di-exo-methylenecyclobutanes via [2 + 2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid

  摘要：

  Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.

  DOI：

  10.1016/s0040-4039(00)61469-7

文献信息

• New access to Di-exo-methylenecyclobutanes via [2 + 2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid
  作者：Makoto Hojo、Kyoji Tomita、Yoji Hirohara、Akira Hosomi

  DOI：10.1016/s0040-4039(00)61469-7

  日期：1993.12

  Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.