dimethyl 5-methyl-5-phenyl-2-(o-tolyl)dihydrofuran-3,3(2H)-dicarboxylate

• 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: dimethyl 5-methyl-5-phenyl-2-(o-tolyl)dihydrofuran-3,3(2H)-dicarboxylate
• 英文别名: dimethyl (2R,5R)-5-methyl-2-(2-methylphenyl)-5-phenyloxolane-3,3-dicarboxylate
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: UKSVOKVSRNEINR-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  bis(methoxycarbonyl)(phenyliodinio)methanide 在 dirhodium tetraacetate 、 tin(II) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 dimethyl 5-methyl-5-phenyl-2-(o-tolyl)dihydrofuran-3,3(2H)-dicarboxylate
  参考文献：
  名称：

  Cyclopropane−Aldehyde Annulations at Quaternary Donor Sites: Stereoselective Access to Highly Substituted Tetrahydrofurans

  摘要：

  A diastereoselective synthesis of pentasubstituted tetrahydrofurans via a Lewis acid catalyzed (3 + 2)-annulation of quatemary donor site cyclopropanes and aldehydes is described. The reaction is catalyzed by Sn(OTf)(2), SnCl4, or Hf(OTf)(4) in yields up to 95% and diastereomeric ratios as high as 99:1.

  DOI：

  10.1021/ol200395e

文献信息

• Cyclopropane−Aldehyde Annulations at Quaternary Donor Sites: Stereoselective Access to Highly Substituted Tetrahydrofurans
  作者：Austin G. Smith、Michael C. Slade、Jeffrey S. Johnson

  DOI：10.1021/ol200395e

  日期：2011.4.15

  A diastereoselective synthesis of pentasubstituted tetrahydrofurans via a Lewis acid catalyzed (3 + 2)-annulation of quatemary donor site cyclopropanes and aldehydes is described. The reaction is catalyzed by Sn(OTf)(2), SnCl4, or Hf(OTf)(4) in yields up to 95% and diastereomeric ratios as high as 99:1.