(R)-6-((E)-2-(tributylstannyl)vinyl)-5,6-dihydro-4-methoxypyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-6-((E)-2-(tributylstannyl)vinyl)-5,6-dihydro-4-methoxypyran-2-one
• 化学式: C₂₀H₃₆O₃Sn
• 分子量: 443.214
• InChiKey: GJVSRVGOOZKDJQ-MAJYTBHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘苯 、 (R)-6-((E)-2-(tributylstannyl)vinyl)-5,6-dihydro-4-methoxypyran-2-one 在 tris(dibenzylideneacetone)dipalladium (0) 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到醉椒素
  参考文献：
  名称：

  Versatile Asymmetric Synthesis of the Kavalactones:  First Synthesis of (+)-Kavain

  摘要：

  Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.

  DOI：

  10.1021/ol0493960

文献信息

• Versatile Asymmetric Synthesis of the Kavalactones:  First Synthesis of (+)-Kavain
  作者：Thomas E. Smith、Mabel Djang、Alan J. Velander、C. Wade Downey、Kathleen A. Carroll、Sophie van Alphen

  DOI：10.1021/ol0493960

  日期：2004.7.1

  Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.