N-allyl-N-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)-benzamide | 1428883-56-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-allyl-N-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)-benzamide
• 英文别名: N-[1-(2-bromophenyl)-3-phenylprop-2-ynyl]-N-prop-2-enylbenzamide
• CAS: 1428883-56-0
• 化学式: C₂₅H₂₀BrNO
• 分子量: 430.344
• InChiKey: LUWPLEHXUPAEEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)-benzamide 在 Grubbs catalyst first generation 、 乙烯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以93%的产率得到N-benzoyl-2-(2-bromophenyl)-3-(1-phenylvinyl)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d
• 作为产物：
  描述：

  苯甲酰氯 、 苯乙炔 、 Allyl-[1-(2-bromo-phenyl)-meth-(E)-ylidene]-amine 在 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以55%的产率得到N-allyl-N-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)-benzamide
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d

文献信息

• Modular strategy for the synthesis of functionalized aryl-fused azabicyclo[2.2.2]octanes via radical-mediated cascade cyclization
  作者：Helena C. Malinakova、Sandeep N. Raikar、Lucas F. McCormick

  DOI：10.1016/j.tetlet.2014.05.001

  日期：2014.7

  A two-step synthesis of rare 2-azabicyclo[2.2.2]octanes is described. N-propargyl amides obtained via Cu(I)-catalyzed three-component coupling, underwent radical-mediated cascade cyclization to afford 5,6-aryl-fused 2-azabicyclo[2.2.2]octanes with arylidene functionality on the two-carbon bridge in 43–62% yields. Phenylidene and 1-naphtylidene derivatives were obtained exclusively as Z diastereomers

  描述了稀有的2-氮杂双环[2.2.2]辛烷的两步合成。通过Cu（I）催化的三组分偶联获得的N-炔丙基酰胺进行自由基介导的级联环化反应，从而在二碳桥上得到具有亚芳基官能团的5,6-芳基稠合的2-氮杂双环[2.2.2]辛烷收率为43-62％。亚苯基和1-萘基衍生物仅作为Z非对映异构体获得，而亚芳基取代基中的富电子基团提供了以2.3∶1M的比例有利于Z非对映异构体的产物混合物。
• Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles
  作者：Sandeep N. Raikar、Helena C. Malinakova

  DOI：10.1021/jo400246d

  日期：2013.4.19

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.