2-but-1-en-3-ynylfuran | 89939-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-but-1-en-3-ynylfuran
• CAS: 89939-86-6
• 化学式: C₈H₆O
• 分子量: 118.135
• InChiKey: IKVNFCOCOCBEEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-but-1-en-3-ynylfuran 在 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 三氟甲磺酸三甲基硅酯 、 zinc trifluoromethanesulfonate 、 potassium carbonate 、 silver nitrate 、 二异丙胺 、 zinc dibromide 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 7.0h， 生成 4-(furan-2-yl)-4-hydroxy-N-methyl-N'-phenyl-N-tosylbut-2-ynimidamide
  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

• Pd‐Senphos Catalyzed <i>trans</i> ‐Selective Cyanoboration of 1,3‐Enynes
  作者：Yuanzhe Zhang、Bo Li、Shih‐Yuan Liu

  DOI：10.1002/anie.202005882

  日期：2020.9.7

  The first trans‐selective cyanoboration reaction of an alkyne, specifically a 1,3‐enyne, is described. The reported palladium‐catalyzed cyanoboration of 1,3‐enynes is site‐, regio‐, and diastereoselective, and is uniquely enabled by the 1,4‐azaborine‐based Senphos ligand structure. Tetra‐substituted alkenyl nitriles are obtained providing useful boron‐dienenitrile building blocks that can be further

  描述了炔烃（特别是 1,3-烯炔）的第一个反式选择性氰基硼化反应。报道的钯催化 1,3-烯炔的氰基硼化反应具有位点选择性、区域选择性和非对映选择性，并且由基于 1,4-氮硼烷的 Senphos 配体结构独特实现。获得四取代的烯基腈，提供有用的硼二烯腈结构单元，可以进一步功能化。我们的方法的实用性已通过抗血小板聚集剂 Satigrel 的合成得到证明。
• Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes
  作者：Sagar Ashok Gawade、Deepak B. Huple、Rai-Shung Liu

  DOI：10.1021/ja412634w

  日期：2014.2.26

  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.