3-isopropyl-6-imino-8,8-dimethyl-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 3-isopropyl-6-imino-8,8-dimethyl-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitrile
• 英文别名: (1S,3S,5S)-6-imino-8,8-dimethyl-3-propan-2-yl-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitrile
• 化学式: C₁₄H₁₆N₄O₂
• 分子量: 272.307
• InChiKey: UKCCEWQZKLCGFC-NURSFMCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  四氰基乙烯 、 异丁醛 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以72%的产率得到3-isopropyl-6-imino-8,8-dimethyl-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitrile
  参考文献：
  名称：

  Reaction of tetracyanoethylene with aldehydes. Synthesis of 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles

  摘要：

  It was discovered by means of dynamic NMR that the 1-(cis-1-methylprop-1-en-1-yl)-1,2-dimethyl-acenaphthylenonium ion generated under conditions of "long life" for carbocations underwent fast (Delta G(#) 35.8 kJ mol(-1) at-103 degrees C) degenerate 1,2-shift of the cis-dimethylvinyl group. Quantum-chemical calculations by DFT method predict lower rate of 1,2-shift for the trans-dimethyl vinyl group compared to cis-dimethylvinyl group and dependence on the cations conformation of the rates of these processes and of the rearrangement mechanism into the ions of phenalenyl type.

  DOI：

  10.1134/s1070428002120060