2,3-dimethyl-1-(3R,3aR,6S,6aR)-[6-(hydroxy)-hexahydrofuro[3,2-b]furan-3-yl]imidazolium trifluoromethanesulfonate | 1142892-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,3-dimethyl-1-(3R,3aR,6S,6aR)-[6-(hydroxy)-hexahydrofuro[3,2-b]furan-3-yl]imidazolium trifluoromethanesulfonate
• 英文别名: 2,3-dimethyl-1-(3R,3aR,6aR)-[6-(hydroxy)-hexahydrofuro[3,2-b]furan-3-yl]imidazolium trifluoromethanesulfonate
• CAS: 1142892-84-9
• 化学式: CF₃O₃S*C₁₁H₁₇N₂O₃
• 分子量: 374.338
• InChiKey: UEIRCAYVMXCXPD-PSQZEURLSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.63
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104.7
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2,3-dimethyl-1-(3R,3aR,6S,6aR)-[6-(acetoxy)-hexahydrofuro[3,2-b]furan-3-yl]imidazolium trifluoromethanesulfonate 在 盐酸 、 乙醇 作用下， 反应 4.0h， 以90%的产率得到2,3-dimethyl-1-(3R,3aR,6S,6aR)-[6-(hydroxy)-hexahydrofuro[3,2-b]furan-3-yl]imidazolium trifluoromethanesulfonate
  参考文献：
  名称：

  Chiral ionic liquids derived from isosorbide: synthesis, properties and applications in asymmetric synthesis

  摘要：

  以异山梨醇为生物可再生底物，设计并合成了一类新型手性铵和咪唑离子液体。研究发现，这些手性离子液体可催化偶氮 Diels-Alder 反应，产生良好的产率和适度的非对映选择性。

  DOI：

  10.1039/b902956g

文献信息

• Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels–Alder reaction
  作者：Olivier Nguyen Van Buu、Audrey Aupoix、Giang Vo-Thanh

  DOI：10.1016/j.tet.2009.01.055

  日期：2009.3

  A novel family of chiral imidazolium-based ionic liquids containing a Chiral moiety and a free hydroxyl function has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels-Alder reaction to give good yields and moderate diastereoselectivities. Chiral ionic liquids are recycled while their efficiency is preserved. (C) 2009 Elsevier Ltd. All rights reserved.