N,4-dimethyl-N-((3E,5E)-6-phenylhexa-3,5-dien-1-yn-1-yl)benzenesulfonamide | 1562381-55-8

• 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,4-dimethyl-N-((3E,5E)-6-phenylhexa-3,5-dien-1-yn-1-yl)benzenesulfonamide
• CAS: 1562381-55-8
• 化学式: C₂₀H₁₉NO₂S
• 分子量: 337.442
• InChiKey: WRHQUFLCSUSTMN-SWACZAGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• 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：

  N,4-dimethyl-N-((3E,5E)-6-phenylhexa-3,5-dien-1-yn-1-yl)benzenesulfonamide 在 三氟甲磺酸三甲基硅酯 、 氢溴酸 、 zinc trifluoromethanesulfonate 、 二异丙胺 、 zinc dibromide 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 6.25h， 生成 N-(4-bromo-5-phenylfuran-2-yl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w
• 作为产物：
  描述：

  6-Phenylhexin-(1)-dien-(3,5) 在 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 N,4-dimethyl-N-((3E,5E)-6-phenylhexa-3,5-dien-1-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w

文献信息

• Hetero-Tetradehydro-Diels–Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines
  作者：Nikolay V. Shcherbakov、Dmitry V. Dar’in、Vadim Yu. Kukushkin、Alexey Yu. Dubovtsev

  DOI：10.1021/acs.joc.1c00558

  日期：2021.5.21

  hetero-tetradehydro-Diels–Alder cycloaddition of enynamides and cyanamides comprises an efficient route to diversely substituted 2,6-diaminopyridines (28 examples; yields up to 99%). The reaction proceeds under very mild conditions (DCM, rt) with high functional group tolerance. The obtained 2,6-diaminopyridines represent a useful synthetic platform with an easily modulated substitution pattern for subsequent

  金（I）催化的乙酰胺和氰酰胺杂四-脱氢-狄尔斯-阿尔德环加成反应是制备不同取代的2,6-二氨基吡啶的有效途径（28个实例；产率高达99％）。反应在具有高官能团耐受性的非常温和的条件下（DCM，rt）进行。所获得的2，6-二氨基吡啶代表有用的合成平台，其具有易于调节的取代模式，用于吡啶核和N-取代基的随后官能化。