(E)-3,3-Diethyl-1-(2-iodo-4-methylphenyl)triaz-1-ene | 460721-14-6

• 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: (E)-3,3-Diethyl-1-(2-iodo-4-methylphenyl)triaz-1-ene
• 英文别名: N-ethyl-N-[(2-iodo-4-methylphenyl)diazenyl]ethanamine
• CAS: 460721-14-6
• 化学式: C₁₁H₁₆IN₃
• 分子量: 317.173
• InChiKey: OMFFRPRDBINJRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3,3-Diethyl-1-(2-iodo-4-methylphenyl)triaz-1-ene 、 二苯基乙炔 在 三正丁胺 、 三(邻甲基苯基)磷 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以73%的产率得到6-methyl-3,4-diphenylcinnoline
  参考文献：
  名称：

  Synthesis of 3,4-disubstituted cinnolines by the Pd-catalyzed annulation of 2-iodophenyltriazenes with an internal alkyne

  摘要：

  A simple and efficient synthesis of cinnolines was achieved by a palladium-catalyzed annulation methodology. 3,4-Disubstituted cinnolines are prepared via palladium-catalyzed annulation of 2-iodophenyltriazenes with an internal alkyne in moderate to good yields. Several internal alkynes are applicable to this reaction and it is compatible with a number of functional groups. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.04.079

文献信息

• Doubly Coarctate-Stabilized Carbenes: Synthetic and Computational Studies
  作者：Brian S. Young、Rainer Herges、Michael M. Haley

  DOI：10.1021/jo3020374

  日期：2013.3.1

  Isoindazoles joined by an ethynyl linker to either a phenyltriazene or a phenyldiazene moiety were synthesized, and their subsequent reactivity was examined. Computations suggest that these molecules could rearrange at moderate temperatures via carbene intermediates that are doubly stabilized by coarctate conjugation. The experimental results corroborate the calculations, as the transient carbene can either be trapped with oxygen or undergo ring opening to afford a rearranged product Additional calculations illustrate some design principles that might lead to stable carbenes that are the global minimum on the coarctate hypersurface.