(3aR,6S,6aR)-4-(dichloromethylidene)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole | 91200-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6S,6aR)-4-(dichloromethylidene)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole
• CAS: 91200-17-8
• 化学式: C₁₃H₁₈Cl₂O₅
• 分子量: 325.189
• InChiKey: LJRKGMXVZLZURB-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,6S,6aR)-4-(dichloromethylidene)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 苄基三乙基氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 68.5h， 生成 (3'aR)-6'c-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2',2'-dimethyl-(3'ar,6'ac)-tetrahydrospiro(cyclopropane-1,4'-furo[3,4-d][1,3]dioxolane)
  参考文献：
  名称：

  Lakhrissi, Mohamed; Chaouch, Aziz; Chapleur, Yves, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 5, p. 531 - 534

  摘要：

  DOI：
• 作为产物：
  描述：

  四氯化碳 、 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone 在 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到(3aR,6S,6aR)-4-(dichloromethylidene)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole
  参考文献：
  名称：

  由糖γ-内酯方便地合成取代的手性四氢呋喃

  摘要：

  糖γ-内酯与六甲基亚磷酸三酰胺-四氯甲烷反应可一步生成二氯烯烃。然后将它们还原为光学活性的四氢呋喃。

  DOI：

  10.1039/c39840000449

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.
• A short route to α-chloro- and α-azido-ulosonic esters
  作者：Mohammed Lakhrissi、Yves Chapleur

  DOI：10.1016/s0040-4039(98)00872-7

  日期：1998.6

  A two step route to alpha-chloro-ulosonic esters from lactones involving the reaction of dichloroolefins with m-chloroperbenzoic acid in dichloromethane is described. Subsequent substitution of chlorine by the azide ion yields the corresponding anomeric azido-esters, which may be useful intermediates for the preparation of "anomeric amino-acids" and related compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A convenient synthesis of substituted chiral tetrahydrofurans from sugar γ-lactones
  作者：Yves Chapleur

  DOI：10.1039/c39840000449

  日期：——

  Sugar γ-lactones react with hexamethylphosphorous triamide–tetrachloromethane to give dichloro-olefins in one step; these are then reduced to optically active tetrahydrofurans.

  糖γ-内酯与六甲基亚磷酸三酰胺-四氯甲烷反应可一步生成二氯烯烃。然后将它们还原为光学活性的四氢呋喃。
• Lakhrissi, Mohamed; Chaouch, Aziz; Chapleur, Yves, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 5, p. 531 - 534
  作者：Lakhrissi, Mohamed、Chaouch, Aziz、Chapleur, Yves

  DOI：——

  日期：——