methyl (2'R,3'S,4'S)-2-[4'-hydroxy-2'-octyltetrahydrofuran-5'-on-3'-yl] acetate | 290347-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl (2'R,3'S,4'S)-2-[4'-hydroxy-2'-octyltetrahydrofuran-5'-on-3'-yl] acetate
• 英文别名: methyl 2-[(2R,3R,4S)-4-hydroxy-2-octyl-5-oxooxolan-3-yl]acetate
• CAS: 290347-29-4
• 化学式: C₁₅H₂₆O₅
• 分子量: 286.368
• InChiKey: ITFVXCNVZABIOX-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2'R,3'S,4'S)-2-[4'-hydroxy-2'-octyltetrahydrofuran-5'-on-3'-yl] acetate 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到(1S,5S,6R)-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 、 三氟化硼乙醚 、 copper(II) sulfate 、 magnesium 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 81.5h， 生成 methyl (2'R,3'S,4'S)-2-[4'-hydroxy-2'-octyltetrahydrofuran-5'-on-3'-yl] acetate
  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.