5-<3-(2H,3H-benzofurfuryl)>pentan-2-one | 138695-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-<3-(2H,3H-benzofurfuryl)>pentan-2-one
• 英文别名: 5-<3-(2H,3H-benzofurfuryl)>-2-pentanone；5-(2,3-Dihydro-1-benzofuran-3-yl)pentan-2-one
• CAS: 138695-38-2
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: SUJCFUZQWJLWIE-UHFFFAOYSA-N

物化性质

• 沸点：
  301.6±21.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-allyloxy-2-iodobenzene 、 丁烯酮 生成 5-<3-(2H,3H-benzofurfuryl)>pentan-2-one
  参考文献：
  名称：

  Conjugate addition reactions of organosamarium species via in situ transmetalation to copper(I) salts

  摘要：

  Preformed organosamarium species, available by reduction of aryl or alkyl halides with SmI2, were treated with copper(I) salts to effect in situ transmetalation and conjugate addition to enones. In a series of copper(I) salts, CuI.P(OEt)3 gave best results in combination with 2 equiv of organosamarium reagent. This new method allows the multiple formation of carbon-carbon bonds through a combination of radical and cuprate chemistry.

  DOI：

  10.1021/jo00032a027

文献信息

• Transmetalation reactions of organosamarium reagents. Chlorosilane-accelerated copper-catalyzed conjugate additions
  作者：Peter Wipf、Srikanth Venkatraman

  DOI：10.1021/jo00064a040

  日期：1993.6

  TMSCl accelerates the conjugate addition of in situ prepared organosamarium reagents to alpha,beta-unsaturated carbonyl compounds and nitriles in the presence of HMPA and catalytic amounts of Cu(I) salts. Reactions at -78-degrees-C leads to silyl enol ethers which are isolated or cleaved with TBAF to give beta-alkylated ketones in 30-90% overall yield. Catalysis is most efficient in the presence of 4 equiv of TMSCl and HMPA. HMPA is also necessary for the in situ preparation of the organosamarium species from alkyl halide and SmI2. Some functional groups (chloride,ether,alkene, amide) are tolerated in this process. In the absence of Cu(I) salts, 1,2-additions of organosamarium reagents to carbonyl groups are also dramatically accelerated by TMSCl/HMPA and occur within minutes at -78-degrees-C.