(4R,5S)-4-vinyl-5-[(S)-1-hydroxyethyl]-4,5-dihydro-2(3H)-furanone | 154914-14-4

• 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,5S)-4-vinyl-5-[(S)-1-hydroxyethyl]-4,5-dihydro-2(3H)-furanone
• 英文别名: (4R,5S)-4-ethenyl-5-[(1S)-1-hydroxyethyl]oxolan-2-one
• CAS: 154914-14-4
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: UABDLJONXGMBBB-VMHSAVOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-vinyl-5-[(S)-1-hydroxyethyl]-4,5-dihydro-2(3H)-furanone 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以89%的产率得到(4R,5S)-5-acetyl-4-vinyl-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2009.11.018
• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以0.14 g的产率得到(4S,5S)-4-vinyl-5-[(S)-1-hydroxyethyl]-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2009.11.018

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.