(2S)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone | 594847-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone
• 英文别名: (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutan-1-one
• CAS: 594847-19-5
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: RAHVDDWGYQHVCC-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (5S,1'S)-5-{1',2'-dihydroxy-1',2'-O-isopropylidene-ethyl}-tetrahydrofuran-2-one
  参考文献：
  名称：

  Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4R,5R)-Muricatacin and the Pheromone (R)-Japonilure

  摘要：

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.

  DOI：

  10.1021/ol035061r
• 作为产物：
  描述：

  (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-oxaspiropentane 在 lithium perchlorate 作用下， 以 苯 为溶剂， 反应 24.0h， 以85%的产率得到(2S)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone
  参考文献：
  名称：

  Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4R,5R)-Muricatacin and the Pheromone (R)-Japonilure

  摘要：

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.

  DOI：

  10.1021/ol035061r

文献信息

• Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4<i>R</i>,5<i>R</i>)-Muricatacin and the Pheromone (<i>R</i>)-Japonilure
  作者：Angela M. Bernard、Angelo Frongia、Pier P. Piras、Francesco Secci

  DOI：10.1021/ol035061r

  日期：2003.8.1

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.