(4R,5R)-5-[(Z)-hex-1-enyl]-4-hydroxydihydrofuran-2(3H)-one | 1402044-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R)-5-[(Z)-hex-1-enyl]-4-hydroxydihydrofuran-2(3H)-one
• 英文别名: (4R,5R)-5-[(Z)-hex-1-enyl]-4-hydroxyoxolan-2-one
• CAS: 1402044-04-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: XGIGOFADLAOFDP-JJKLJZTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4R,5R)-4-hydroxy-5-[(E)-oct-1-enyl]dihydrofuran-2(3H)-one 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以83%的产率得到(3aR,5R,6R,6aS)-5-butyl-6-iodotetrahydrofuro-[3,2-b]furan-2(5H)-one
  参考文献：
  名称：

  A Protecting-Group-Free Synthesis of Hagen’s Gland Lactones

  摘要：

  A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-delta-lactone to beta-hydroxy-gamma-vinyl-gamma-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.

  DOI：

  10.1021/jo301465z

文献信息

• A Protecting-Group-Free Synthesis of Hagen’s Gland Lactones
  作者：Rodney A. Fernandes、Pullaiah Kattanguru

  DOI：10.1021/jo301465z

  日期：2012.10.19

  A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-delta-lactone to beta-hydroxy-gamma-vinyl-gamma-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.