(4R,5R)-bis[(allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane | 783339-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-bis[(allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4R,5R)-2,2-dimethyl-4,5-bis(prop-2-enoxymethyl)-1,3-dioxolane
• CAS: 783339-91-3
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: QPXIDXOSWWULDC-VXGBXAGGSA-N

物化性质

• 沸点：
  307.1±37.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-bis[(allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 sodium azide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 (2S,3S)-3-azido-1,4-bis(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)butan-2-ol
  参考文献：
  名称：

  Enantiopure fluorous amino-derivatives: synthesis and some applications in asymmetric organometallic catalysis

  摘要：

  The preparation of (2R,3R)-1,4-bis[(1H,1H,2H,2H,3H,3H-perfluoroundecyl)oxy]butane-2,3-diol 5 from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol is described. This fluorous diol 5 can be easily converted to the corresponding fluorous enantiopure diamine 8 and amino alcohol 12. While diamine 8 afforded fluorous diimine 9, amino alcohol 12 is the precursor of imino alcohol 13 and amino alcohol 14. Enantioselectivities of up to 31% were obtained in the reduction of acetophenone using iridium or ruthenium complexes associated with these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.008
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 以96%的产率得到(4R,5R)-bis[(allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Enantiopure fluorous amino-derivatives: synthesis and some applications in asymmetric organometallic catalysis

  摘要：

  The preparation of (2R,3R)-1,4-bis[(1H,1H,2H,2H,3H,3H-perfluoroundecyl)oxy]butane-2,3-diol 5 from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol is described. This fluorous diol 5 can be easily converted to the corresponding fluorous enantiopure diamine 8 and amino alcohol 12. While diamine 8 afforded fluorous diimine 9, amino alcohol 12 is the precursor of imino alcohol 13 and amino alcohol 14. Enantioselectivities of up to 31% were obtained in the reduction of acetophenone using iridium or ruthenium complexes associated with these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.008

文献信息

• Enantiopure fluorous amino-derivatives: synthesis and some applications in asymmetric organometallic catalysis
  作者：Jerome Bayardon、David Maillard、Gianluca Pozzi、Denis Sinou

  DOI：10.1016/j.tetasy.2004.07.008

  日期：2004.9

  The preparation of (2R,3R)-1,4-bis[(1H,1H,2H,2H,3H,3H-perfluoroundecyl)oxy]butane-2,3-diol 5 from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol is described. This fluorous diol 5 can be easily converted to the corresponding fluorous enantiopure diamine 8 and amino alcohol 12. While diamine 8 afforded fluorous diimine 9, amino alcohol 12 is the precursor of imino alcohol 13 and amino alcohol 14. Enantioselectivities of up to 31% were obtained in the reduction of acetophenone using iridium or ruthenium complexes associated with these compounds. (C) 2004 Elsevier Ltd. All rights reserved.