(2S,3S,5S)-2-pentyl-5-styryl-tetrahydrofuran-3-ol | 1146741-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,5S)-2-pentyl-5-styryl-tetrahydrofuran-3-ol
• 英文别名: (2S,3S,5S)-2-pentyl-5-[(E)-2-phenylethenyl]oxolan-3-ol
• CAS: 1146741-22-1
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: DFNDUYSBHHPJHJ-OAEJALACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S)-2-pentyl-5-styryl-tetrahydrofuran-3-ol 在 臭氧 、 polymer supported triphenylphosphine 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 (2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde 、 苯甲醛
  参考文献：
  名称：

  Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural

  摘要：

  A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer.

  DOI：

  10.1021/ol900324s

文献信息

• Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural
  作者：Jeffrey Mowat、Baldip Kang、Branden Fonovic、Travis Dudding、Robert Britton

  DOI：10.1021/ol900324s

  日期：2009.5.21

  A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer.