2,5-anhydro-1-deoxy-1,1-dichloro-3,4-O-isopropylidene-D-erythro-pent-1-enitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-1-deoxy-1,1-dichloro-3,4-O-isopropylidene-D-erythro-pent-1-enitol
• 英文别名: (3aS,6aS)-4-(dichloromethylidene)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole
• 化学式: C₈H₁₀Cl₂O₃
• 分子量: 225.072
• InChiKey: VNAJZSBYYGGJEN-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氯化碳 、 (3aS,6aS)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到2,5-anhydro-1-deoxy-1,1-dichloro-3,4-O-isopropylidene-D-erythro-pent-1-enitol
  参考文献：
  名称：

  Dichloromethylenation of Lactones. 6. Efficient Synthesis of Dichloroolefins from Lactones and Acetates Using Triphenylphosphine and Tetrachloromethane

  摘要：

  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.

  DOI：

  10.1021/jo00098a039

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.