(+)-7,8-dioxabicyclo[3.2.1]oct-3-en-2-ol | 375348-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (+)-7,8-dioxabicyclo[3.2.1]oct-3-en-2-ol
• 英文别名: (1R,4R,5S)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol
• CAS: 375348-84-8
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: LPADRPJZOJHCDL-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-7,8-dioxabicyclo[3.2.1]oct-3-en-2-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(+)-levoglucosenone
  参考文献：
  名称：

  Lipase-Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer

  摘要：

  A synthesis of both enantiomers of levoglucosenone from acrolein dimer has been developed by employing lipase-mediated kinetic hydrolysis. Thus, acrolein dimer is transformed into racemic dihydrolevoglucosenone by sequential hydride reduction, oxidative acetalization, and Swern oxidation. Employing Saegusa-Larock conditions, dihydrolevoglucosenone is transformed into racemic levoglucosenone. The lipase-mediated resolution was best carried out under hydrolysis conditions with the endo-acetate generated from racemic levoglucosenone to give rise to highly enantioenriched (+)-alcohol and enantiopure (-)-acetate serving as the precursors of enantiopure levoglucosenone having the corresponding chirality.

  DOI：

  10.1002/1615-4169(200108)343:6/7<618::aid-adsc618>3.0.co;2-e
• 作为产物：
  描述：

  (+)-2-acetoxy-7,8-dioxabicyclo[3.2.1]oct-3-ene 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以86%的产率得到(+)-7,8-dioxabicyclo[3.2.1]oct-3-en-2-ol
  参考文献：
  名称：

  Lipase-Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer

  摘要：

  A synthesis of both enantiomers of levoglucosenone from acrolein dimer has been developed by employing lipase-mediated kinetic hydrolysis. Thus, acrolein dimer is transformed into racemic dihydrolevoglucosenone by sequential hydride reduction, oxidative acetalization, and Swern oxidation. Employing Saegusa-Larock conditions, dihydrolevoglucosenone is transformed into racemic levoglucosenone. The lipase-mediated resolution was best carried out under hydrolysis conditions with the endo-acetate generated from racemic levoglucosenone to give rise to highly enantioenriched (+)-alcohol and enantiopure (-)-acetate serving as the precursors of enantiopure levoglucosenone having the corresponding chirality.

  DOI：

  10.1002/1615-4169(200108)343:6/7<618::aid-adsc618>3.0.co;2-e

文献信息

• Lipase-Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer
  作者：Kohei Kadota、Takashi Kurusu、Takahiko Taniguchi、Kunio Ogasawara

  DOI：10.1002/1615-4169(200108)343:6/7<618::aid-adsc618>3.0.co;2-e

  日期：2001.8

  A synthesis of both enantiomers of levoglucosenone from acrolein dimer has been developed by employing lipase-mediated kinetic hydrolysis. Thus, acrolein dimer is transformed into racemic dihydrolevoglucosenone by sequential hydride reduction, oxidative acetalization, and Swern oxidation. Employing Saegusa-Larock conditions, dihydrolevoglucosenone is transformed into racemic levoglucosenone. The lipase-mediated resolution was best carried out under hydrolysis conditions with the endo-acetate generated from racemic levoglucosenone to give rise to highly enantioenriched (+)-alcohol and enantiopure (-)-acetate serving as the precursors of enantiopure levoglucosenone having the corresponding chirality.