(S)-3-methyl-5-pivaloyloxymethyl-2(5H)-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-3-methyl-5-pivaloyloxymethyl-2(5H)-furanone
• 英文别名: [(2S)-4-methyl-5-oxo-2H-furan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: NJJSHKHTAUYQIH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碳酸亚乙烯酯 、 (S)-3-methyl-5-pivaloyloxymethyl-2(5H)-furanone 以 丙酮 为溶剂， 反应 8.0h， 以61%的产率得到(1S,4S,5S,6S,7R)-6,7-(carbonyldioxy)-1-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of [3.3.0]‐Fused γ‐Butyrolactones of Carbohydrates

  摘要：

  A facile and stereoselective method is described for the preparation of fused 2,3-gamma-butyrolactones of lyxofuranose from the unexpected rearrangement in basic media of the photocycloadduct between homochiral 2(5H)-furanones and vinylene carbonate.

  DOI：

  10.1081/car-120026454
• 作为产物：
  描述：

  2-methyl-5-pivaloyloxymethyl-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3-one 以 苯 为溶剂， 反应 192.0h， 以71%的产率得到(S)-3-methyl-5-pivaloyloxymethyl-2(5H)-furanone
  参考文献：
  名称：

  Stereoselective Synthesis of [3.3.0]‐Fused γ‐Butyrolactones of Carbohydrates

  摘要：

  A facile and stereoselective method is described for the preparation of fused 2,3-gamma-butyrolactones of lyxofuranose from the unexpected rearrangement in basic media of the photocycloadduct between homochiral 2(5H)-furanones and vinylene carbonate.

  DOI：

  10.1081/car-120026454

文献信息

• Regio- and diastereoselectivity studies on the photocycloaddition of ketene diethyl acetal to chiral 2(5H)-furanones
  作者：Albert Rustullet、Marta Racamonde、Ramon Alibés、Pedro de March、Marta Figueredo、Josep Font

  DOI：10.1016/j.tet.2008.07.082

  日期：2008.9

  The photochemical [2+2] cycloaddition of 1,1-diethoxyethylene to chiral 2(5H)-furanones is investigated. The effect of the substituents of the lactone and the polarity of the solvents on the chemical yield, regioselectivity, and facial diastereoselectivity is evaluated. The reactions in ether proceed with excellent regioselectivity and good yields. Hydrolysis of the ketal group of the major cycloadducts

  研究了1,1-二乙氧基乙烯与手性2（5 H）-呋喃酮的光化学[2 + 2]环加成反应。评估了内酯的取代基和溶剂的极性对化学收率，区域选择性和面部非对映选择性的影响。在乙醚中的反应以优异的区域选择性和良好的收率进行。主要环加合物的缩酮基团的水解得到与γ-内酯融合的对映体纯的环丁酮。
• Stereoselective Synthesis of [3.3.0]‐Fused γ‐Butyrolactones of Carbohydrates
  作者：Ramon Alibés、José Luís Bourdelande、Anna Gregori、Josep Font、Albert Rustullet、Teodor Parella

  DOI：10.1081/car-120026454

  日期：2003.12.31

  A facile and stereoselective method is described for the preparation of fused 2,3-gamma-butyrolactones of lyxofuranose from the unexpected rearrangement in basic media of the photocycloadduct between homochiral 2(5H)-furanones and vinylene carbonate.