Iodo(4-methylenecyclohexyl)acetonitrile | 147151-56-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Iodo(4-methylenecyclohexyl)acetonitrile
• 英文别名: 2-Iodo-2-(4-methylidenecyclohexyl)acetonitrile
• CAS: 147151-56-2
• 化学式: C₉H₁₂IN
• 分子量: 261.105
• InChiKey: KJRCHPAATUJMOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  Iodo(4-methylenecyclohexyl)acetonitrile 在 六甲基二锡 作用下， 以 various solvent(s) 为溶剂， 以82%的产率得到1-(Iodomethyl)-7-cyanobicyclo<2.2.1>heptane
  参考文献：
  名称：

  Synthesis of bridgehead-substituted bicyclo[2.2.1]heptanes by radical cyclization

  摘要：

  A kinetic investigation shows that the rate of cyclization (k(C)) of the (4-methylenecyclohexyl)methyl radical 3 at 25-degrees-C is 4.4 x 10(2) s-1, which is considerably slower than that (2.3 x 10(5) s-1) of the parent 5-hexenyl radical. The energy of activation for the process 3 - 4 is 12.8 kcal mol-1, which is in excellent agreement with theoretical values derived from force-field calculations. Ring-closure of appropriately substituted (4-methylenecyclohexyl)methyl radical precursors allows the synthesis of bicyclo[2.2.1]heptyl systems with useful functionality at the bridgehead to be achieved readily and in high yield. An interesting example is given of the application of an iodine-atom-transfer cyclization to the synthesis of a bicyclo[2.2.1]heptane functionalized at C7 and C1.

  DOI：

  10.1021/jo00060a029
• 作为产物：
  描述：

  4-亚甲基环己烷羧酸乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 28.08h， 生成 Iodo(4-methylenecyclohexyl)acetonitrile
  参考文献：
  名称：

  Synthesis of bridgehead-substituted bicyclo[2.2.1]heptanes by radical cyclization

  摘要：

  A kinetic investigation shows that the rate of cyclization (k(C)) of the (4-methylenecyclohexyl)methyl radical 3 at 25-degrees-C is 4.4 x 10(2) s-1, which is considerably slower than that (2.3 x 10(5) s-1) of the parent 5-hexenyl radical. The energy of activation for the process 3 - 4 is 12.8 kcal mol-1, which is in excellent agreement with theoretical values derived from force-field calculations. Ring-closure of appropriately substituted (4-methylenecyclohexyl)methyl radical precursors allows the synthesis of bicyclo[2.2.1]heptyl systems with useful functionality at the bridgehead to be achieved readily and in high yield. An interesting example is given of the application of an iodine-atom-transfer cyclization to the synthesis of a bicyclo[2.2.1]heptane functionalized at C7 and C1.

  DOI：

  10.1021/jo00060a029