6,6-diphenyl-2,3-bis(4-tolylamino)-1,4-diazapentafulvene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,6-diphenyl-2,3-bis(4-tolylamino)-1,4-diazapentafulvene
• 英文别名: 2-benzhydryl-N-(4-methylphenyl)-5-(4-methylphenyl)iminoimidazol-4-amine
• 化学式: C₃₀H₂₆N₄
• 分子量: 442.563
• InChiKey: UAOUZXDZXRTZCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基乙酰氯 、 1,2-Bisethan-1,2-diamin 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以45%的产率得到6,6-diphenyl-2,3-bis(4-tolylamino)-1,4-diazapentafulvene
  参考文献：
  名称：

  Ketene-N,N-acetals as Key Intermediates in the Formation of Tetraazapentafulvadienes

  摘要：

  The easily accessible bis-amidines 2 react with adamantane-1-carbonyl chloride 3 to yield the 4H-imidazole 4. If the carbonic acid chloride contains an alpha -hydrogen, the reaction takes a completely different path. In this case, tetraazapen-tafulvadienes 11 are formed via a cascade reaction that contains two single electron transfer (SET) steps. Cyclic ketene-N,N-acetals 7 are postulated to be the initial intermediates, which then readily form radical cations, the presence of which could be confirmed by ESR measurements even though intramolecular trapping proved impossible due to their extreme reactivity. DFT calculations at the B3LYP/6311+G(d,p) level support these experimental findings. The crucial ketene-N,N-acetals 7 can be stabilized through steric interactions and/or the introduction of conjugated substructures, thus leading to the formation of fulvenoid structures such as 14a and 14b.

  DOI：

  10.1002/1099-0690(200112)2001:23<4551::aid-ejoc4551>3.0.co;2-9