4-methyl-N-(naphthalen-2-ylmethyl)-N-(propa-1,2-dien-1-yl)benzenesulfonamide | 1353455-79-4

• 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: 4-methyl-N-(naphthalen-2-ylmethyl)-N-(propa-1,2-dien-1-yl)benzenesulfonamide
• CAS: 1353455-79-4
• 化学式: C₂₁H₁₉NO₂S
• 分子量: 349.453
• InChiKey: LJHCZCMWASQXOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(2-(1-methyl-1H-indol-3-yl)ethyl)benzenesulfonamide 、 4-methyl-N-(naphthalen-2-ylmethyl)-N-(propa-1,2-dien-1-yl)benzenesulfonamide 在 C₅₆H₄₂NO₂P*Au⁽¹⁺⁾*Cl^(1-) 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以92%的产率得到4-methyl-N-((E)-3-((3aS,8aS)-8-methyl-1-tosyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-yl)prop-1-en-1-yl)-N-(naphthalen-2-ylmethyl)benzenesulfonamide
  参考文献：
  名称：

  Enantioselective gold catalyzed cascade construction of pyrroloindoline derivatives

  摘要：

  A new method was developed to enantioselectively synthesize pyrroloindolines from the reaction of allenoamides with tryptamines by using BINOL derived phosphoramidate ligated gold catalyst. Electrophilic addition of the gold-allene complex led to tryptamine's C-3-dearomatization, which, followed by C-2 cyclization, provided the desired annulation product. In addition, furoindoline product could also be prepared from the reaction of tryptol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.021

文献信息

• Silaborative Assembly of Allenamides and Alkynes: Highly Regio‐ and Stereocontrolled Access to Bi‐ or Trimetallic Skipped Dienes
  作者：Tapas R. Pradhan、Mukti Paudel、Taisiia Feoktistova、Paul Ha‐Yeon Cheong、Jin Kyoon Park

  DOI：10.1002/anie.202116154

  日期：2022.4.19

  A highly stereo- and regiocontrolled reaction between allenamides, alkynes, and a bis-metallative reagent (Me2PhSiBpin and Et3SiBpin) is reported for the first time. This new method for accessing functionalized 1,4-dienes under phosphine-free palladium catalysis has good functional group compatibility as showcased through late-stage diversification. By virtue of computational calculations and experimental

  首次报道了丙二酰胺、炔烃和双金属试剂（Me 2 PhSiBpin 和 Et 3 SiBpin）之间的高度立体和区域控制反应。这种在无膦钯催化下获得功能化 1,4-二烯的新方法具有良好的官能团兼容性，如后期多样化所示。凭借计算计算和实验证据，证实了区域和立体化学洞察力。