N-(pent-3-yn-1-yl)cyclopropanamine | 1249055-73-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(pent-3-yn-1-yl)cyclopropanamine
• 英文别名: N-pent-3-ynylcyclopropanamine
• CAS: 1249055-73-9
• 化学式: C₈H₁₃N
• 分子量: 123.198
• InChiKey: VPRCCXLNCQMISG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(pent-3-yn-1-yl)cyclopropanamine 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 邻二氯苯 为溶剂， 160.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 methyl 4-methyl-5-oxo-2,3,5,6,7,7a-hexahydro-1H-indole-1-carboxylate
  参考文献：
  名称：

  Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones

  摘要：

  Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

  DOI：

  10.1021/ja401936c
• 作为产物：
  描述：

  3-戊炔-1-醇 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 32.0h， 生成 N-(pent-3-yn-1-yl)cyclopropanamine
  参考文献：
  名称：

  Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones

  摘要：

  Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

  DOI：

  10.1021/ja401936c

文献信息

• Rhodacyclopentanones as Linchpins for the Atom Economical Assembly of Diverse Polyheterocycles
  作者：Gang-Wei Wang、Olivia Boyd、Tom A. Young、Sophie M. Bertrand、John F. Bower

  DOI：10.1021/jacs.9b12421

  日期：2020.1.29

  We outline a conceptual blueprint that provides direct and atom economical access to a wide range of complex polyheterocycles. Our method capitalizes on the ambiphilic reactivity of rhodac-yclopentanones that arise upon exposure of cyclopropanes to Rh(I) catalysts and CO. Using this approach, a wide array of polycyclizations are achieved, including variants that involve powerful dearomatizations and medium ring formations.
• Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones
  作者：Megan H. Shaw、Ekaterina Y. Melikhova、Daniel P. Kloer、William G. Whittingham、John F. Bower

  DOI：10.1021/ja401936c

  日期：2013.4.3

  Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.