Acetic acid (4R,4aS,7R,7aR)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester | 140160-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Acetic acid (4R,4aS,7R,7aR)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester
• CAS: 140160-53-8
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: ZDOJKVXRCKNBHP-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (4R,4aS,7R,7aR)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester 在 samarium diiodide 、 乙二醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到
  参考文献：
  名称：

  A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction

  摘要：

  A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.

  DOI：

  10.1016/s0040-4039(00)92313-x

文献信息

• Dichloromethylenation of Lactones. 6. Efficient Synthesis of Dichloroolefins from Lactones and Acetates Using Triphenylphosphine and Tetrachloromethane
  作者：Mohamed Lakhrissi、Yves Chapleur

  DOI：10.1021/jo00098a039

  日期：1994.9

  Triphenylphosphine and tetrachloromethane react cleanly in refluxing tetrahydrofuran with substituted gamma and delta-lactones and some esters to afford the corresponding dichloroolefins in good yields. This new Wittig-type reaction provides an easy entry to this new class of compounds and tolerates a large variety of protecting groups. Application of this methodology to the dichloroolefination of simple lactones, sugar-derived lactones, and other biologically significant lactones is described.