1-(1'-methylcyclopropyl)-2,2,3,3-tetramethylcyclopropane

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: 1-(1'-methylcyclopropyl)-2,2,3,3-tetramethylcyclopropane
• 英文别名: 1,1,2,2-Tetramethyl-3-(1-methylcyclopropyl)cyclopropane
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: WUZASFFJCMZTJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,2,3,3-四甲基环丙烷羧酸乙酯 在 氢氧化钾 、 diethylzinc 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 17.0h， 生成 1-(1'-methylcyclopropyl)-2,2,3,3-tetramethylcyclopropane
  参考文献：
  名称：

  Experimental and Theoretical Investigations of Ring-Expansion in 1-Methylcyclopropylcarbene

  摘要：

  1-Methylcyclopropylcarbene, generated by photolysis of two isomeric hydrocarbon precursors, undergoes ring-expansion readily to give 1-methylcyclobutene. Experimentally, intramolecular carbon-hydrogen insertions are not observed. Trapping studies with TME demonstrates the formation of the expected cyclopropane adduct, and via a double-reciprocal analysis, the lifetime of 1-methylcyclopropylcarbene was determined to be 12 ns in 1,1,2-trichlorotrifluoroethane. Computational studies show that the barrier to ring-expansion is significantly smaller in 1-methylcyclopropylcarbene than in cyclopropylcarbene. The origin of the increased rate of ring-expansion is due to stabilization of the positive charge that occurs at the incipient tertiary carbon that is attached to the migrating carbon center.

  DOI：

  10.1021/jo9903454