(2R,5R)-5-Hexyl-3-methyl-2,5-dihydro-furan-2-carboxylic acid methyl ester | 135397-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,5R)-5-Hexyl-3-methyl-2,5-dihydro-furan-2-carboxylic acid methyl ester
• 英文别名: (2S,5R)-5-Hexyl-3-methyl-2,5-dihydro-furan-2-carboxylic acid methyl ester
• CAS: 135397-22-7
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: HQTQXAWBHXQPBF-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-2-Hydroxy-3-methyl-undeca-3,4-dienoic acid methyl ester 在 silver nitrate 、 calcium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 生成 (2R,5R)-5-Hexyl-3-methyl-2,5-dihydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of enantioenriched .alpha.-hydroxy-.alpha.-allenylacetic acids by [2,3] Wittig rearrangement of .alpha.-(propargyloxy)acetates

  摘要：

  Optically active (R)-(propargyloxy)acetic esters 5, available in ca. 90% ee through reduction of alkynones 2 with Chirald-LiAlH4 followed by alkylation with chloroacetic acid and esterification with CH2N2, undergo highly stereoselective [2,3] rearrangement upon treatment with LDA in THF at -78-degrees-C followed by Cp2ZrCl2 to afford alpha-(S)-hydroxy-beta-(R)-allenic esters 7 with complete transfer of chirality and > 90% diastereoselectivity. Upon treatment with TESOTf in Et3N the (R)-(propargyloxy) acetic esters 5 afford the diastereomeric alpha-(R)-hydroxy-beta-(R)-allenic esters 8 stereoselectively. Both hydroxy esters 7 and 8 cyclize stereospecifically to trans- and cis-2,5-dihydrofurans 13-15 and 17-19 upon treatment with AgNO3-CaCO3, PhSeCl, or NBS.

  DOI：

  10.1021/jo00016a020