N-ethyl-N-[(2-iodo-4-nitrophenyl)diazenyl]ethanamine | 460721-19-1

• 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: N-ethyl-N-[(2-iodo-4-nitrophenyl)diazenyl]ethanamine
• CAS: 460721-19-1
• 化学式: C₁₀H₁₃IN₄O₂
• 分子量: 348.143
• InChiKey: XQLRCSYSUOOHPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-[(2-iodo-4-nitrophenyl)diazenyl]ethanamine 、 丙炔酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到Methyl 3-[2-(diethylaminodiazenyl)-5-nitrophenyl]prop-2-ynoate
  参考文献：
  名称：

  Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems

  摘要：

  The synthesis of isoindazoles bearing alpha-ketoester and alpha-hydroxyester groups via the coarctate cyclization of ester-terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene intermediate to make the coarctate cyclization the thermodynamic pathway. Density functional theory (DFT) computations reveal ca. 8-9 kcal mol(-1) lower energy transition states for the coarctate pathway compared to the parent system.

  DOI：

  10.1021/jo9011283

文献信息

• Synthesis of 3,4-disubstituted cinnolines by the Pd-catalyzed annulation of 2-iodophenyltriazenes with an internal alkyne
  作者：Chuan Zhu、Motoki Yamane

  DOI：10.1016/j.tet.2011.04.079

  日期：2011.7

  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.