3-nitro-N-(2-methyl-1-propenyl)-2-pyridinamine | 424799-90-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-nitro-N-(2-methyl-1-propenyl)-2-pyridinamine
• 英文别名: 3-nitro-N-(2-methyl-1-propen-1-yl)-2-pyridinamine；N-(2-methylprop-1-enyl)-3-nitropyridin-2-amine
• CAS: 424799-90-6
• 化学式: C₉H₁₁N₃O₂
• 分子量: 193.205
• InChiKey: PPEHIAYDHHIWOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-N-(2-methyl-1-propenyl)-2-pyridinamine 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 一氧化碳 、 1,3-双(二苯基膦)丙烷 、 邻菲罗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、607.99 kPa 条件下， 反应 6.0h， 以34%的产率得到1,2-dihydro-2,2-dimethylpyrido[2,3-b]pyrazine
  参考文献：
  名称：

  Palladium-catalyzed synthesis of quinoxaline derivatives

  摘要：

  A palladium-catalyzed reductive N-heteroannulation of enamines derived from 2-nitrobenzenamines forming mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalin-2-ones is described. The reactions are performed using bis(dibenzylideneacetone)palladium(0), 1,3-bis(diphenylphosphino)propane, and 1,10-phenanthroline in DMF under 6 atm of carbon monoxide at 70 degrees C. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.083
• 作为产物：
  描述：

  2-氨基-3-硝基吡啶 、 异丁醛 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以43%的产率得到N-[1-(3-nitropyridin-2-ylamino)-2-methylpropyl]-3-nitropyridin-2-amine
  参考文献：
  名称：

  Palladium-catalyzed synthesis of quinoxaline derivatives

  摘要：

  A palladium-catalyzed reductive N-heteroannulation of enamines derived from 2-nitrobenzenamines forming mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalin-2-ones is described. The reactions are performed using bis(dibenzylideneacetone)palladium(0), 1,3-bis(diphenylphosphino)propane, and 1,10-phenanthroline in DMF under 6 atm of carbon monoxide at 70 degrees C. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.083

文献信息

• A Novel Palladium-Catalyzed Synthesis of 1,2-Dihydroquinoxalines and 3,4-Dihydroquinoxalinones
  作者：Björn C. G. Söderberg、Jeffery M. Wallace、Joaquín Tamariz

  DOI：10.1021/ol025640g

  日期：2002.4.1

  [GRAPHICS]Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) afford readily separated mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones. Addition of a catalytic amount of 1,10-phenanthroline to the reaction mixture substantially improved the yield of products.
• Palladium-catalyzed synthesis of quinoxaline derivatives
  作者：Jeffery M. Wallace、Björn C.G. Söderberg、Joaquín Tamariz、Novruz G. Akhmedov、Mathew T. Hurley

  DOI：10.1016/j.tet.2008.07.083

  日期：2008.10

  A palladium-catalyzed reductive N-heteroannulation of enamines derived from 2-nitrobenzenamines forming mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalin-2-ones is described. The reactions are performed using bis(dibenzylideneacetone)palladium(0), 1,3-bis(diphenylphosphino)propane, and 1,10-phenanthroline in DMF under 6 atm of carbon monoxide at 70 degrees C. (C) 2008 Elsevier Ltd. All rights reserved.