(3aR,5R,6R,6aS)-5-butyl-6-iodotetrahydrofuro-[3,2-b]furan-2(5H)-one | 1402043-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (3aR,5R,6R,6aS)-5-butyl-6-iodotetrahydrofuro-[3,2-b]furan-2(5H)-one
• 英文别名: (2R,3R,3aS,6aR)-2-butyl-3-iodo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 1402043-96-2
• 化学式: C₁₀H₁₅IO₃
• 分子量: 310.132
• InChiKey: UKVOGVQHANJZRO-ZXZZCXTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (3aR,5R,6R,6aS)-5-butyl-6-iodotetrahydrofuro-[3,2-b]furan-2(5H)-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.0h， 以94%的产率得到(3aR,5R,6aR)-5-butylperhydrofuro-[3,2-b]furan-2-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
• 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 practical and improved process for the synthesis of Hagen’s gland lactones by catalytic hydro-deiodination
  作者：Dipali A. Chaudhari、Pullaiah Kattanguru、Rodney A. Fernandes

  DOI：10.1016/j.tetasy.2014.05.004

  日期：2014.7

  Catalytic hydro-deiodination has been efficiently employed in the development of a benign process for the synthesis of Hagen's gland lactones. The process was developed with only two column chromatographic purifications and is applicable for gram scale synthesis. No protecting groups were used in the synthesis which is an added advantage. (C) 2014 Elsevier Ltd. All rights reserved.