(1S,3S,5S,6S)-3-methoxy-6-octyl-2,7-dioxabicyclo[3.3.0]octan-8-one | 290347-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (1S,3S,5S,6S)-3-methoxy-6-octyl-2,7-dioxabicyclo[3.3.0]octan-8-one
• 英文别名: (2S,3aS,4S,6aS)-2-methoxy-4-octyl-3,3a,4,6a-tetrahydro-2H-furo[2,3-c]furan-6-one
• CAS: 290347-28-3
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: UBVNEZSQHJTKEQ-XUXIUFHCSA-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：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3S,5S,6S)-3-methoxy-6-octyl-2,7-dioxabicyclo[3.3.0]octan-8-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以76%的产率得到(1S,5S,6S)-6-octyl-2,7-dioxabicyclo[3.3.0]octan-3,8-dione
  参考文献：
  名称：

  The Enantioselective Formal Synthesis of (+)-Avenaciolide and (+)-Isoavenaciolide from Tri-O-acetyl-D-glucal Using a Ring Contraction Reaction as the Key Step

  摘要：

  We describe a formal synthesis of (+)-avenaciolide and (+)-isoavenaciolide starting from methyl tri-O-acetyl-D-glucal. The key steps are a ring-contraction reaction of compound 8 to give the bicycle 6, and the oxidation of the diol 9 to the bis-lactone framework.

  DOI：

  10.1002/1099-0690(200006)2000:12<2285::aid-ejoc2285>3.0.co;2-8
• 作为产物：
  描述：

  (+)-(1S,3S,5R,6R)-2,7-Dioxa-6-hydroxy-3-methoxybicyclo<3.3.0>octane 在 potassium permanganate 、 copper(II) sulfate 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 9.5h， 生成 (1S,3S,5S,6S)-3-methoxy-6-octyl-2,7-dioxabicyclo[3.3.0]octan-8-one
  参考文献：
  名称：

  The Enantioselective Formal Synthesis of (+)-Avenaciolide and (+)-Isoavenaciolide from Tri-O-acetyl-D-glucal Using a Ring Contraction Reaction as the Key Step

  摘要：

  We describe a formal synthesis of (+)-avenaciolide and (+)-isoavenaciolide starting from methyl tri-O-acetyl-D-glucal. The key steps are a ring-contraction reaction of compound 8 to give the bicycle 6, and the oxidation of the diol 9 to the bis-lactone framework.

  DOI：

  10.1002/1099-0690(200006)2000:12<2285::aid-ejoc2285>3.0.co;2-8

文献信息

• The Enantioselective Formal Synthesis of (+)-Avenaciolide and (+)-Isoavenaciolide from Tri-O-acetyl-D-glucal Using a Ring Contraction Reaction as the Key Step
  作者：Eva Alcázar、Mohamed Kassou、Isabel Matheu、Sergio Castillón

  DOI：10.1002/1099-0690(200006)2000:12<2285::aid-ejoc2285>3.0.co;2-8

  日期：2000.6

  We describe a formal synthesis of (+)-avenaciolide and (+)-isoavenaciolide starting from methyl tri-O-acetyl-D-glucal. The key steps are a ring-contraction reaction of compound 8 to give the bicycle 6, and the oxidation of the diol 9 to the bis-lactone framework.