2,3-Dimethylidenecyclobutane-1-carbonitrile | 153339-05-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3-Dimethylidenecyclobutane-1-carbonitrile
• CAS: 153339-05-0
• 化学式: C₇H₇N
• 分子量: 105.139
• InChiKey: IOHHTPCJBAGAFL-UHFFFAOYSA-N

物化性质

• 沸点：
  193.9±29.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2,3-Dimethylidenecyclobutane-1-carbonitrile 、 富马酸二甲酯 在 四氯化钛 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 以42%的产率得到dimethyl (3S,4S)-7-cyanobicyclo[4.2.0]oct-1(6)-ene-3,4-dicarboxylate
  参考文献：
  名称：

  Allenylmethylsilane Derivative as a Synthetic Equivalent of 1,2,3-Butatriene: Synthesis and Reactions of Di-exo-methylenecyclobutanes and -cyclobutenes

  摘要：

  2-Methoxyallenylmethylsilane 与烯烃和炔烃发生 [2+2] 环加成反应，分别生成环丁烷和环丁烯。环加成产物通过甲氧基和硅基的 1,2- 消除作用转化为二外亚甲基化合物。这些二外-亚甲基环丁烷和环丁烯与烯烃和 1,3-二烯反应，生成融合的双环和三环化合物。

  DOI：

  10.1246/cl.1998.331
• 作为产物：
  描述：

  2-Methanesulfonyl-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81%的产率得到2,3-Dimethylidenecyclobutane-1-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

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.
• Allenylmethylsilane Derivative as a Synthetic Equivalent of 1,2,3-Butatriene: Synthesis and Reactions of Di-exo-methylenecyclobutanes and -cyclobutenes
  作者：Makoto Hojo、Chikara Murakami、Shinya Nakamura、Akira Hosomi

  DOI：10.1246/cl.1998.331

  日期：1998.4

  2-Methoxyallenylmethylsilane reacts with alkenes and alkynes in a [2+2] cycloaddition mode to give cyclobutanes and cyclobutenes, respectively. Cycloadducts are converted to di-exo-methylene compounds through 1,2-elimination of the methoxy and silyl groups. These di-exo-methylenecyclobutanes and -cyclobutenes react with alkenes and 1,3-dienes to afford fused bi- and tricyclic compounds.

  2-Methoxyallenylmethylsilane 与烯烃和炔烃发生 [2+2] 环加成反应，分别生成环丁烷和环丁烯。环加成产物通过甲氧基和硅基的 1,2- 消除作用转化为二外亚甲基化合物。这些二外-亚甲基环丁烷和环丁烯与烯烃和 1,3-二烯反应，生成融合的双环和三环化合物。