N,N,4-trimethyl-7-phenyl-2-tosyl-2,3-dihydro-1H-pyrrolo[3,4-c]-pyridin-6-amine | 1394159-47-7

• 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,N,4-trimethyl-7-phenyl-2-tosyl-2,3-dihydro-1H-pyrrolo[3,4-c]-pyridin-6-amine
• 英文别名: N,N,4-trimethyl-2-(4-methylphenyl)sulfonyl-7-phenyl-1,3-dihydropyrrolo[3,4-c]pyridin-6-amine
• CAS: 1394159-47-7
• 化学式: C₂₃H₂₅N₃O₂S
• 分子量: 407.536
• InChiKey: BQCHVQLAFFRIDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲基氢胺 、 N-(3-phenylprop-2-ynyl)-N-tosylbut-2-yn-1-ylamine 在 1,1'-(pyridine-2,6-diyl)bis(N-mesitylmethanimine) 、 iron(II) chloride 、 锌 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 N,N,7-trimethyl-4-phenyl-2-tosyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-amine 、 N,N,4-trimethyl-7-phenyl-2-tosyl-2,3-dihydro-1H-pyrrolo[3,4-c]-pyridin-6-amine
  参考文献：
  名称：

  Iron-Catalyzed Formation of 2-Aminopyridines from Diynes and Cyanamides

  摘要：

  Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively.

  DOI：

  10.1021/jo3012418

文献信息

• Iron-Catalyzed Formation of 2-Aminopyridines from Diynes and Cyanamides
  作者：Timothy K. Lane、Brendan R. D’Souza、Janis Louie

  DOI：10.1021/jo3012418

  日期：2012.9.7

  Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively.
• Iron-Catalyzed Cycloaddition Reaction of Diynes and Cyanamides at Room Temperature
  作者：Chunxiang Wang、Dongping Wang、Fen Xu、Bin Pan、Boshun Wan

  DOI：10.1021/jo400057t

  日期：2013.4.5

  An iron-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. Insights toward the reaction process were investigated through in situ IR spectra and control experiments. In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system.