(3S,4S,6S,7S)-4,7-epoxydodeca-3,6-diol | 1139919-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,6S,7S)-4,7-epoxydodeca-3,6-diol
• 英文别名: (2S,3S,5S)-5-[(1S)-1-hydroxypropyl]-2-pentyloxolan-3-ol
• CAS: 1139919-38-2
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: GUVWQHDDKSOFRC-BJDJZHNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S,6S,7S)-4,7-epoxydodeca-3,6-diol 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 反应 48.0h， 生成
  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
• 作为产物：
  描述：

  (2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde 、 乙基溴化镁 在 水 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (3R,4S,6S,7S)-4,7-epoxydodeca-3,6-diol 、 (3S,4S,6S,7S)-4,7-epoxydodeca-3,6-diol
  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.