(3aS,4S,6R,6aR)-6-hexyl-4-hydroxytetrahydrofuro[3,4-b]furan-2(3H)-one | 1132793-41-9

• 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: (3aS,4S,6R,6aR)-6-hexyl-4-hydroxytetrahydrofuro[3,4-b]furan-2(3H)-one
• 英文别名: (3aS,4S,6R,6aR)-6-hexyl-4-hydroxy-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-2-one
• CAS: 1132793-41-9
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: FVJNLHSBDMTMIV-SPFNVWMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,6aR)-6-hexyl-4-hydroxytetrahydrofuro[3,4-b]furan-2(3H)-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3aS,6R,6aR)-6-hexyltetrahydrofuro[3,4-b]furan-2,4-dione
  参考文献：
  名称：

  Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

  摘要：

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.084
• 作为产物：
  描述：

  (4R,5R)-4-vinyl-5-[(R)-1-hydroxyheptyl]-4,5-dihydro-2(3H)-furanone 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以96%的产率得到(3aS,4S,6R,6aR)-6-hexyl-4-hydroxytetrahydrofuro[3,4-b]furan-2(3H)-one
  参考文献：
  名称：

  Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

  摘要：

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.084

文献信息

• Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
  作者：Rodney A. Fernandes、Arun B. Ingle、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2009.11.018

  日期：2009.12

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.